In Depth https://firstround.com/ en Welcome to In Depth, a podcast from The First Round Review that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves. Hosted by Brett Berson, a partner at First Round, In Depth will cover a lot of ground and a wide range of topics, from hiring executives and becoming a better manager, to the importance of storytelling inside of your organization. But every interview will hit the level of tactical depth where the very best advice is found. We hope you’ll join us. Subscribe to “In Depth” now and learn more at firstround.com https://megaphone.imgix.net/podcasts/9426cbf8-25fe-11ec-a0b4-fb6861cc1eaf/image/f27cea2953ad25c68029f33bc99ba58b.png?ixlib=rails-4.3.1&max-w=3000&max-h=3000&fit=crop&auto=format,compress In Depth https://firstround.com/ no episodic First Round Welcome to In Depth, a podcast from The First Round Review that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves. Hosted by Brett Berson, a partner at First Round, In Depth will cover a lot of ground and a wide range of topics, from hiring executives and becoming a better manager, to the importance of storytelling inside of your organization. But every interview will hit the level of tactical depth where the very best advice is found. We hope you’ll join us. Subscribe to “In Depth” now and learn more at firstround.com Welcome to In Depth, a podcast from The First Round Review that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves. Hosted by Brett Berson, a partner at First Round, In Depth will cover a lot of ground and a wide range of topics, from hiring executives and becoming a better manager, to the importance of storytelling inside of your organization. But every interview will hit the level of tactical depth where the very best advice is found. We hope you’ll join us. Subscribe to “In Depth” now and learn more at firstround.com

]]> First Round review@firstround.com What nobody tells engineers about becoming a CEO | Jay Kreps (Co-founder and CEO, Confluent) Jay Kreps is the co-founder and CEO of Confluent, the company built around Apache Kafka — the open-source data streaming platform he originally built while at LinkedIn. In this conversation, Jay shares his full journey: how Confluent grew from a scrappy group of engineers with no go-to-market experience into a publicly traded enterprise software company. He makes the case that the difference between what a company can do, and what it must do, is one of the most underrated building levers; illustrated through his years spent pushing Confluent towards a cloud product, in the face of widespread opposition. In this episode, we discuss: Why moving from software engineer to CEO requires almost an entirely new skillset The product marketing pyramid Jay built to explain Kafka to the world How Confluent bludgeoned its way to a cloud-first business when the early product was “embarrassing” The critical difference between what a company can do and what it must do What keeps scaling companies from becoming "Chipotle” References: Amazon Web Services: https://aws.amazon.com/ Apache Kafka: https://kafka.apache.org/ Benchmark: https://www.benchmark.com/ Confluent: https://www.confluent.io/ Jun Rao: https://www.linkedin.com/in/junrao LinkedIn: https://www.linkedin.com/ McKinsey & Company: https://www.mckinsey.com/ MySpace: https://www.myspace.com/ Neha Narkhede: https://www.linkedin.com/in/nehanarkhede Oracle: https://www.oracle.com/ Red Hat: https://www.redhat.com/ Snowflake: https://www.snowflake.com/ Where to find Jay: LinkedIn: https://www.linkedin.com/in/jaykreps/ Twitter/X: https://x.com/jaykreps Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 01:18 Making the leap from engineer to CEO 03:33 The 80% rule: what a CEO actually needs to know 04:54 Scaling different business disciplines 09:31 How Confluent’s story began in LinkedIn 12:13 The growing need for scalable data tech 13:37 What the early Kafka product looked like 16:38 Kafka’s underwhelming open-source launch 18:38 The blog post that accelerated Kafka’s adoption 20:16 Why so many marketing messages fail 28:08 The decision to build Confluent 34:24 Planning to fundraise before building the product 39:19 Confluent’s early years: Tough product decisions 47:07 The underrated growth lever question for companies 55:46 Why founder optimism is an overrated trait 1:00:29 What should founders give up as they scale? 1:02:47 Why people become trapped in a failure mindset 1:08:33 The Chipotle problem: Losing excellence at scale Thu, 26 Mar 2026 11:00:00 -0000 full First Round Jay Kreps is the co-founder and CEO of Confluent, the company built around Apache Kafka — the open-source data streaming platform he originally built while at LinkedIn. In this conversation, Jay shares his full journey: how Confluent grew from a scrappy group of engineers with no go-to-market experience into a publicly traded enterprise software company. He makes the case that the difference between what a company can do, and what it must do, is one of the most underrated building levers; illustrated through his years spent pushing Confluent towards a cloud product, in the face of widespread opposition. In this episode, we discuss: Why moving from software engineer to CEO requires almost an entirely new skillset The product marketing pyramid Jay built to explain Kafka to the world How Confluent bludgeoned its way to a cloud-first business when the early product was “embarrassing” The critical difference between what a company can do and what it must do What keeps scaling companies from becoming "Chipotle” References: Amazon Web Services: https://aws.amazon.com/ Apache Kafka: https://kafka.apache.org/ Benchmark: https://www.benchmark.com/ Confluent: https://www.confluent.io/ Jun Rao: https://www.linkedin.com/in/junrao LinkedIn: https://www.linkedin.com/ McKinsey & Company: https://www.mckinsey.com/ MySpace: https://www.myspace.com/ Neha Narkhede: https://www.linkedin.com/in/nehanarkhede Oracle: https://www.oracle.com/ Red Hat: https://www.redhat.com/ Snowflake: https://www.snowflake.com/ Where to find Jay: LinkedIn: https://www.linkedin.com/in/jaykreps/ Twitter/X: https://x.com/jaykreps Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 01:18 Making the leap from engineer to CEO 03:33 The 80% rule: what a CEO actually needs to know 04:54 Scaling different business disciplines 09:31 How Confluent’s story began in LinkedIn 12:13 The growing need for scalable data tech 13:37 What the early Kafka product looked like 16:38 Kafka’s underwhelming open-source launch 18:38 The blog post that accelerated Kafka’s adoption 20:16 Why so many marketing messages fail 28:08 The decision to build Confluent 34:24 Planning to fundraise before building the product 39:19 Confluent’s early years: Tough product decisions 47:07 The underrated growth lever question for companies 55:46 Why founder optimism is an overrated trait 1:00:29 What should founders give up as they scale? 1:02:47 Why people become trapped in a failure mindset 1:08:33 The Chipotle problem: Losing excellence at scale Jay Kreps is the co-founder and CEO of Confluent, the company built around Apache Kafka — the open-source data streaming platform he originally built while at LinkedIn. In this conversation, Jay shares his full journey: how Confluent grew from a scrappy group of engineers with no go-to-market experience into a publicly traded enterprise software company. He makes the case that the difference between what a company can do, and what it must do, is one of the most underrated building levers; illustrated through his years spent pushing Confluent towards a cloud product, in the face of widespread opposition.

In this episode, we discuss:

  • Why moving from software engineer to CEO requires almost an entirely new skillset
  • The product marketing pyramid Jay built to explain Kafka to the world
  • How Confluent bludgeoned its way to a cloud-first business when the early product was “embarrassing”
  • The critical difference between what a company can do and what it must do
  • What keeps scaling companies from becoming "Chipotle”

References:

Where to find Jay:

Where to find Brett:

Where to find First Round Capital:

Timestamps:

01:18 Making the leap from engineer to CEO

03:33 The 80% rule: what a CEO actually needs to know

04:54 Scaling different business disciplines

09:31 How Confluent’s story began in LinkedIn

12:13 The growing need for scalable data tech

13:37 What the early Kafka product looked like

16:38 Kafka’s underwhelming open-source launch

18:38 The blog post that accelerated Kafka’s adoption

20:16 Why so many marketing messages fail

28:08 The decision to build Confluent

34:24 Planning to fundraise before building the product

39:19 Confluent’s early years: Tough product decisions

47:07 The underrated growth lever question for companies

55:46 Why founder optimism is an overrated trait

1:00:29 What should founders give up as they scale?

1:02:47 Why people become trapped in a failure mindset

1:08:33 The Chipotle problem: Losing excellence at scale

]]> 3990 The product wisdom every CPO should ignore | Jeremy Epling (CPO, Vanta) In the latest episode of Executive Function, Brett is joined by Jeremy Epling, CPO of security and compliance platform Vanta. Jeremy details his career journey, unpacking what it took to make the jump from tenured Microsoft executive to startup CPO. He also shares hard-won insights: how to maintain shipping velocity as headcount explodes, how to manage performance without the safety net of big-company process, and what it means to run a product org where the buck truly stops with you. In today's episode, we discuss: The mindset shift that made Jeremy's transition to startup CPO work Why it’s essential for the CPO to stay connected to details The rule to ensure teams ship fast while growing quickly Why rigid hierarchies derail quality decision-making How Jeremy uses open office hours for the entire company References: Christina Cacioppo: https://www.linkedin.com/in/ccacioppo/ Dropbox: https://www.dropbox.com GitHub: https://www.github.com Ironclad: https://www.ironcladapp.com Jensen Huang: https://www.linkedin.com/in/jenhsunhuang/ Lovable: https://lovable.dev Microsoft: https://www.microsoft.com Nat Friedman: https://www.linkedin.com/in/natfriedman/ NVIDIA: https://www.nvidia.com Span: https://www.span.app/ v0: https://v0.dev Vanta: https://www.vanta.com Where to find Jeremy: LinkedIn: https://www.linkedin.com/in/jeremy-epling-j40/ Twitter/X: https://x.com/jeremy_epling Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 00:00 Introduction 00:09 Why most big-tech executives fail at startups 05:38 Great product leaders stay in the details 09:21 The biggest mindset shift from VP to CPO 16:24 Revenue and product teams are always at odds 18:00 The key to a quality CPO and CRO relationship 23:21 Stop making your team fetch rocks 25:54 Who ultimately oversees the quality bar? 32:27 Why rigid hierarchies kill great companies 36:38 How to leave actionable, detailed feedback 38:55 Great CPOs should avoid comfort metrics 47:27 A glimpse into Jeremy’s working week 49:07 The case for weekly 1:1s 55:13 Why ICs are the unsung heroes of a company 58:25 Jeremy’s most formative career moments 1:07:55 The hardest skills Jeremy had to learn 1:09:31 Why great managers know when to push Thu, 19 Mar 2026 11:00:00 -0000 full First Round In the latest episode of Executive Function, Brett is joined by Jeremy Epling, CPO of security and compliance platform Vanta. Jeremy details his career journey, unpacking what it took to make the jump from tenured Microsoft executive to startup CPO. He also shares hard-won insights: how to maintain shipping velocity as headcount explodes, how to manage performance without the safety net of big-company process, and what it means to run a product org where the buck truly stops with you. In today's episode, we discuss: The mindset shift that made Jeremy's transition to startup CPO work Why it’s essential for the CPO to stay connected to details The rule to ensure teams ship fast while growing quickly Why rigid hierarchies derail quality decision-making How Jeremy uses open office hours for the entire company References: Christina Cacioppo: https://www.linkedin.com/in/ccacioppo/ Dropbox: https://www.dropbox.com GitHub: https://www.github.com Ironclad: https://www.ironcladapp.com Jensen Huang: https://www.linkedin.com/in/jenhsunhuang/ Lovable: https://lovable.dev Microsoft: https://www.microsoft.com Nat Friedman: https://www.linkedin.com/in/natfriedman/ NVIDIA: https://www.nvidia.com Span: https://www.span.app/ v0: https://v0.dev Vanta: https://www.vanta.com Where to find Jeremy: LinkedIn: https://www.linkedin.com/in/jeremy-epling-j40/ Twitter/X: https://x.com/jeremy_epling Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 00:00 Introduction 00:09 Why most big-tech executives fail at startups 05:38 Great product leaders stay in the details 09:21 The biggest mindset shift from VP to CPO 16:24 Revenue and product teams are always at odds 18:00 The key to a quality CPO and CRO relationship 23:21 Stop making your team fetch rocks 25:54 Who ultimately oversees the quality bar? 32:27 Why rigid hierarchies kill great companies 36:38 How to leave actionable, detailed feedback 38:55 Great CPOs should avoid comfort metrics 47:27 A glimpse into Jeremy’s working week 49:07 The case for weekly 1:1s 55:13 Why ICs are the unsung heroes of a company 58:25 Jeremy’s most formative career moments 1:07:55 The hardest skills Jeremy had to learn 1:09:31 Why great managers know when to push In the latest episode of Executive Function, Brett is joined by Jeremy Epling, CPO of security and compliance platform Vanta. Jeremy details his career journey, unpacking what it took to make the jump from tenured Microsoft executive to startup CPO. He also shares hard-won insights: how to maintain shipping velocity as headcount explodes, how to manage performance without the safety net of big-company process, and what it means to run a product org where the buck truly stops with you.

In today's episode, we discuss:

  • The mindset shift that made Jeremy's transition to startup CPO work
  • Why it’s essential for the CPO to stay connected to details
  • The rule to ensure teams ship fast while growing quickly
  • Why rigid hierarchies derail quality decision-making
  • How Jeremy uses open office hours for the entire company

References:

Where to find Jeremy:

Where to find Brett:

Where to find First Round Capital:

Timestamps:

00:00 Introduction

00:09 Why most big-tech executives fail at startups

05:38 Great product leaders stay in the details

09:21 The biggest mindset shift from VP to CPO

16:24 Revenue and product teams are always at odds

18:00 The key to a quality CPO and CRO relationship

23:21 Stop making your team fetch rocks

25:54 Who ultimately oversees the quality bar?

32:27 Why rigid hierarchies kill great companies

36:38 How to leave actionable, detailed feedback

38:55 Great CPOs should avoid comfort metrics

47:27 A glimpse into Jeremy’s working week

49:07 The case for weekly 1:1s

55:13 Why ICs are the unsung heroes of a company

58:25 Jeremy’s most formative career moments

1:07:55 The hardest skills Jeremy had to learn

1:09:31 Why great managers know when to push

]]> 4194 Building Zipline: From launch disaster to drone-delivery giant | Keller Cliffton (Co-founder, CEO) Keller Cliffton is the co-founder and CEO of Zipline, the world's largest commercial autonomous delivery system, which today serves 5,000 hospitals across multiple countries and saves an estimated 17,000 lives per year. In this episode, Keller breaks down his extreme hiring philosophy that has powered Zipline for over a decade. He also walks through Zipline’s full origin story: from a near-dead home robot startup to a scrappy bet on drone blood delivery in Rwanda, to 135 million autonomous miles flown. In today's episode, we discuss: Why Zipline hires teenagers over PhDs Why the best startup employees are "heat-seeking missiles for pain" The 5 leadership attributes Zipline has never shared publicly The brutal firing advice that shaped Keller’s leadership How Rwanda’s health minister changed Zipline’s trajectory References: Airbnb: https://www.airbnb.com Alfred Lin: https://www.linkedin.com/in/linalfred/ Amazon: https://www.amazon.com Apple: https://www.apple.com Brian Chesky: https://www.linkedin.com/in/brianchesky/ Cleveland Clinic: https://my.clevelandclinic.org Netflix: https://www.netflix.com Paul Kagame: https://www.linkedin.com/in/paulkagame/ Reflect Orbital: https://www.reflectorbital.com Sequoia Capital: https://www.sequoiacapital.com SpaceX: https://www.spacex.com Sphero: https://www.sphero.com Tesla: https://www.tesla.com University of Washington: https://www.washington.edu Walmart: https://www.walmart.com Zipline: https://www.zipline.com Where to find Keller: LinkedIn: https://www.linkedin.com/in/kellerrc/ Twitter/X: https://x.com/Keller Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 00:00 Introduction 02:11 Why Zipline doesn't hire for experience 06:04 Are founders born or made? 07:37 Why Zipline hires 17-year-olds over PhDs 17:03 The employees Zipline doesn't want 18:53 The ultimate startup hire is a "heat-seeking missile" 20:36 Why blind references are a non-negotiable 23:07 Can candidates admit when they screwed up? 30:10 Zipline's secret leadership playbook 35:16 Why you should always fire quickly 36:26 The early vision for Zipline 39:48 How Zipline almost died - twice 44:55 From toy robots to drone delivery: Zipline's pivot 51:35 How Rwanda's health minister changed everything 57:10 Why Zipline's launch was a "complete disaster" 1:04:05 Scaling from 1 hospital to 5000 1:05:17 The 10x hardware cost rule every founder should know Thu, 12 Mar 2026 16:16:00 -0000 full First Round Keller Cliffton is the co-founder and CEO of Zipline, the world's largest commercial autonomous delivery system, which today serves 5,000 hospitals across multiple countries and saves an estimated 17,000 lives per year. In this episode, Keller breaks down his extreme hiring philosophy that has powered Zipline for over a decade. He also walks through Zipline’s full origin story: from a near-dead home robot startup to a scrappy bet on drone blood delivery in Rwanda, to 135 million autonomous miles flown. In today's episode, we discuss: Why Zipline hires teenagers over PhDs Why the best startup employees are "heat-seeking missiles for pain" The 5 leadership attributes Zipline has never shared publicly The brutal firing advice that shaped Keller’s leadership How Rwanda’s health minister changed Zipline’s trajectory References: Airbnb: https://www.airbnb.com Alfred Lin: https://www.linkedin.com/in/linalfred/ Amazon: https://www.amazon.com Apple: https://www.apple.com Brian Chesky: https://www.linkedin.com/in/brianchesky/ Cleveland Clinic: https://my.clevelandclinic.org Netflix: https://www.netflix.com Paul Kagame: https://www.linkedin.com/in/paulkagame/ Reflect Orbital: https://www.reflectorbital.com Sequoia Capital: https://www.sequoiacapital.com SpaceX: https://www.spacex.com Sphero: https://www.sphero.com Tesla: https://www.tesla.com University of Washington: https://www.washington.edu Walmart: https://www.walmart.com Zipline: https://www.zipline.com Where to find Keller: LinkedIn: https://www.linkedin.com/in/kellerrc/ Twitter/X: https://x.com/Keller Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 00:00 Introduction 02:11 Why Zipline doesn't hire for experience 06:04 Are founders born or made? 07:37 Why Zipline hires 17-year-olds over PhDs 17:03 The employees Zipline doesn't want 18:53 The ultimate startup hire is a "heat-seeking missile" 20:36 Why blind references are a non-negotiable 23:07 Can candidates admit when they screwed up? 30:10 Zipline's secret leadership playbook 35:16 Why you should always fire quickly 36:26 The early vision for Zipline 39:48 How Zipline almost died - twice 44:55 From toy robots to drone delivery: Zipline's pivot 51:35 How Rwanda's health minister changed everything 57:10 Why Zipline's launch was a "complete disaster" 1:04:05 Scaling from 1 hospital to 5000 1:05:17 The 10x hardware cost rule every founder should know Keller Cliffton is the co-founder and CEO of Zipline, the world's largest commercial autonomous delivery system, which today serves 5,000 hospitals across multiple countries and saves an estimated 17,000 lives per year. In this episode, Keller breaks down his extreme hiring philosophy that has powered Zipline for over a decade. He also walks through Zipline’s full origin story: from a near-dead home robot startup to a scrappy bet on drone blood delivery in Rwanda, to 135 million autonomous miles flown.

In today's episode, we discuss:

  • Why Zipline hires teenagers over PhDs
  • Why the best startup employees are "heat-seeking missiles for pain"
  • The 5 leadership attributes Zipline has never shared publicly
  • The brutal firing advice that shaped Keller’s leadership
  • How Rwanda’s health minister changed Zipline’s trajectory

References:

Where to find Keller:

Where to find Brett:

Where to find First Round Capital:

Timestamps:

00:00 Introduction

02:11 Why Zipline doesn't hire for experience

06:04 Are founders born or made?

07:37 Why Zipline hires 17-year-olds over PhDs

17:03 The employees Zipline doesn't want

18:53 The ultimate startup hire is a "heat-seeking missile"

20:36 Why blind references are a non-negotiable

23:07 Can candidates admit when they screwed up?

30:10 Zipline's secret leadership playbook

35:16 Why you should always fire quickly

36:26 The early vision for Zipline

39:48 How Zipline almost died - twice

44:55 From toy robots to drone delivery: Zipline's pivot

51:35 How Rwanda's health minister changed everything

57:10 Why Zipline's launch was a "complete disaster"

1:04:05 Scaling from 1 hospital to 5000

1:05:17 The 10x hardware cost rule every founder should know

]]> 4250 Snowflake’s first sales hire on scaling from $0 to $3.5B | Chris Degnan (Former CRO, Snowflake) Chris Degnan was the first sales hire at Snowflake and spent 11 years scaling the company from zero to $3.5 billion in revenue as its CRO, working alongside four different CEOs and learning from each one. In this episode, Chris breaks down what it actually takes to scale an enterprise sales organization, why MEDDIC is the methodology every founder should know, and what working under Frank Slootman taught him about firing fast, taking feedback and finding the fakers in your team. In today's episode, we discuss: What the CRO job looks like at $10M vs. $1B+ Why sales leaders must know how to sell the product themselves The MEDDIC methodology and why it's a founder's best insurance policy How to find the fakers, manage-uppers and passengers in your org What Frank Slootman got right — and wrong — about scaling Snowflake Why most AI companies will face a go-to-market reckoning References: Amazon: https://www.amazon.com/ Bob Muglia: https://www.linkedin.com/in/bob-muglia-714ba592/ Carl Eschenbach: https://www.linkedin.com/in/carl-eschenbach-980543/ Christian Kleinerman: https://www.linkedin.com/in/christian-kleinerman-a973102/ Denise Persson: https://www.linkedin.com/in/denisepersson/ Dell: https://www.dell.com/ Frank Slootman: https://www.linkedin.com/in/frankslootman/ John McMahon: https://www.linkedin.com/in/johnmcmahon1/ Michael Scarpelli: https://www.linkedin.com/in/michael-scarpelli-1b289b9/ Microsoft: https://www.microsoft.com/ Oracle: https://www.oracle.com/ Salesforce: https://www.salesforce.com/ Snowflake: https://www.snowflake.com/ Sridhar Ramaswamy: https://www.linkedin.com/in/sridhar-ramaswamy/ Stanford Graduate School of Business: https://www.gsb.stanford.edu/ Where to find Chris: LinkedIn: https://www.linkedin.com/in/chris-degnan/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 00:00 What is the job of a CRO? 01:12 What excellence looks like at different revenue stages 02:59 Sales leaders need to know how to sell the product 04:52 The hardest skill leaders have to learn 08:17 You need to stay open to feedback - at all levels 14:01 Sales, segmentation, and international expansion 16:17 Why MEDDIC is the foundation for every sales org 20:32 The metrics that actually matter 22:56 A week in the life of a CRO at scale 28:32 Navigating compensation at a GTM organization 31:45 What technical CEOs get wrong about GTM 36:01 The role of hunger in great sales leaders 40:35 What makes an exceptional IC sales rep 46:41 Dysfunctional vs. high-performing executive teams 48:01 Chris' most impactful decisions at Snowflake 49:53 "When there's doubt, there's no doubt" 54:49 Learning from world-class leaders Thu, 26 Feb 2026 12:00:00 -0000 full First Round Chris Degnan was the first sales hire at Snowflake and spent 11 years scaling the company from zero to $3.5 billion in revenue as its CRO, working alongside four different CEOs and learning from each one. In this episode, Chris breaks down what it actually takes to scale an enterprise sales organization, why MEDDIC is the methodology every founder should know, and what working under Frank Slootman taught him about firing fast, taking feedback and finding the fakers in your team. In today's episode, we discuss: What the CRO job looks like at $10M vs. $1B+ Why sales leaders must know how to sell the product themselves The MEDDIC methodology and why it's a founder's best insurance policy How to find the fakers, manage-uppers and passengers in your org What Frank Slootman got right — and wrong — about scaling Snowflake Why most AI companies will face a go-to-market reckoning References: Amazon: https://www.amazon.com/ Bob Muglia: https://www.linkedin.com/in/bob-muglia-714ba592/ Carl Eschenbach: https://www.linkedin.com/in/carl-eschenbach-980543/ Christian Kleinerman: https://www.linkedin.com/in/christian-kleinerman-a973102/ Denise Persson: https://www.linkedin.com/in/denisepersson/ Dell: https://www.dell.com/ Frank Slootman: https://www.linkedin.com/in/frankslootman/ John McMahon: https://www.linkedin.com/in/johnmcmahon1/ Michael Scarpelli: https://www.linkedin.com/in/michael-scarpelli-1b289b9/ Microsoft: https://www.microsoft.com/ Oracle: https://www.oracle.com/ Salesforce: https://www.salesforce.com/ Snowflake: https://www.snowflake.com/ Sridhar Ramaswamy: https://www.linkedin.com/in/sridhar-ramaswamy/ Stanford Graduate School of Business: https://www.gsb.stanford.edu/ Where to find Chris: LinkedIn: https://www.linkedin.com/in/chris-degnan/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 00:00 What is the job of a CRO? 01:12 What excellence looks like at different revenue stages 02:59 Sales leaders need to know how to sell the product 04:52 The hardest skill leaders have to learn 08:17 You need to stay open to feedback - at all levels 14:01 Sales, segmentation, and international expansion 16:17 Why MEDDIC is the foundation for every sales org 20:32 The metrics that actually matter 22:56 A week in the life of a CRO at scale 28:32 Navigating compensation at a GTM organization 31:45 What technical CEOs get wrong about GTM 36:01 The role of hunger in great sales leaders 40:35 What makes an exceptional IC sales rep 46:41 Dysfunctional vs. high-performing executive teams 48:01 Chris' most impactful decisions at Snowflake 49:53 "When there's doubt, there's no doubt" 54:49 Learning from world-class leaders Chris Degnan was the first sales hire at Snowflake and spent 11 years scaling the company from zero to $3.5 billion in revenue as its CRO, working alongside four different CEOs and learning from each one. In this episode, Chris breaks down what it actually takes to scale an enterprise sales organization, why MEDDIC is the methodology every founder should know, and what working under Frank Slootman taught him about firing fast, taking feedback and finding the fakers in your team.

In today's episode, we discuss:

  • What the CRO job looks like at $10M vs. $1B+
  • Why sales leaders must know how to sell the product themselves
  • The MEDDIC methodology and why it's a founder's best insurance policy
  • How to find the fakers, manage-uppers and passengers in your org
  • What Frank Slootman got right — and wrong — about scaling Snowflake
  • Why most AI companies will face a go-to-market reckoning

References:

Where to find Chris:

Where to find Brett:

Where to find First Round Capital:

Timestamps:

00:00 What is the job of a CRO?

01:12 What excellence looks like at different revenue stages

02:59 Sales leaders need to know how to sell the product

04:52 The hardest skill leaders have to learn

08:17 You need to stay open to feedback - at all levels

14:01 Sales, segmentation, and international expansion

16:17 Why MEDDIC is the foundation for every sales org

20:32 The metrics that actually matter

22:56 A week in the life of a CRO at scale

28:32 Navigating compensation at a GTM organization

31:45 What technical CEOs get wrong about GTM

36:01 The role of hunger in great sales leaders

40:35 What makes an exceptional IC sales rep

46:41 Dysfunctional vs. high-performing executive teams

48:01 Chris' most impactful decisions at Snowflake

49:53 "When there's doubt, there's no doubt"

54:49 Learning from world-class leaders

]]> 3597 Why 90% of CROs will fall behind in the next 2 years | Stevie Case (CRO, Vanta) Stevie Case is the CRO of Vanta, the trust management platform serving everyone from founders to Fortune 100 CISOs. A former pro-video gamer who stumbled into sales through a mentor's bet, Stevie has built one of the most unconventional paths to the C-suite in tech. In this episode, she unpacks why early revenue hires fail, what separates a true CRO from a VP of Sales, and why she believes fewer than 10% of current CROs will thrive by 2028. In today's episode, we discuss: Why early revenue hires fail What a top 1% CRO actually does The scaling mistake Stevie made by copying Twilio's playbook at Vanta Why Vanta remains 100% sales-led at every segment AI vs. humans in go-to-market References: Cursor: https://cursor.sh/ Gong: https://www.gong.io/ Salesforce: https://www.salesforce.com/ Twilio: https://www.twilio.com/ Vanta: https://www.vanta.com/ Where to find Stevie: LinkedIn: https://www.linkedin.com/in/steviecase/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 00:00 Why early revenue hires fail 02:23 Who to hire at $5M in revenue 04:16 Coin-operated sellers vs. long-term builders 05:57 What excellence looks like in the CRO role 07:44 Metrics, confidence, and velocity 12:04 Should CROs lead sales? 14:39 From shy seller to revenue leader 16:36 Learning to scale at Twilio 17:44 "There is no CRO playbook" 19:58 Stevie's scaling mistake at Vanta 22:16 Why Vanta stays 100% sales-led 23:16 The value of planning 24-26 months ahead 29:54 When trusting intuition was the wrong call 30:49 Do humans still have a place in the future of GTM? 33:33 Stevie's leadership non-negotiables 36:36 The myth of hiring for industry expertise 40:00 What stays centralized in a 600-person company 47:09 The hidden leverage of a customer's first 30 days 53:42 Why the CRO role will face enormous changes by 2028 58:42 What leaders must do now to stay relevant 01:02:30 Unpacking the CEO-CRO dynamic Thu, 19 Feb 2026 12:00:00 -0000 full First Round Stevie Case is the CRO of Vanta, the trust management platform serving everyone from founders to Fortune 100 CISOs. A former pro-video gamer who stumbled into sales through a mentor's bet, Stevie has built one of the most unconventional paths to the C-suite in tech. In this episode, she unpacks why early revenue hires fail, what separates a true CRO from a VP of Sales, and why she believes fewer than 10% of current CROs will thrive by 2028. In today's episode, we discuss: Why early revenue hires fail What a top 1% CRO actually does The scaling mistake Stevie made by copying Twilio's playbook at Vanta Why Vanta remains 100% sales-led at every segment AI vs. humans in go-to-market References: Cursor: https://cursor.sh/ Gong: https://www.gong.io/ Salesforce: https://www.salesforce.com/ Twilio: https://www.twilio.com/ Vanta: https://www.vanta.com/ Where to find Stevie: LinkedIn: https://www.linkedin.com/in/steviecase/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 00:00 Why early revenue hires fail 02:23 Who to hire at $5M in revenue 04:16 Coin-operated sellers vs. long-term builders 05:57 What excellence looks like in the CRO role 07:44 Metrics, confidence, and velocity 12:04 Should CROs lead sales? 14:39 From shy seller to revenue leader 16:36 Learning to scale at Twilio 17:44 "There is no CRO playbook" 19:58 Stevie's scaling mistake at Vanta 22:16 Why Vanta stays 100% sales-led 23:16 The value of planning 24-26 months ahead 29:54 When trusting intuition was the wrong call 30:49 Do humans still have a place in the future of GTM? 33:33 Stevie's leadership non-negotiables 36:36 The myth of hiring for industry expertise 40:00 What stays centralized in a 600-person company 47:09 The hidden leverage of a customer's first 30 days 53:42 Why the CRO role will face enormous changes by 2028 58:42 What leaders must do now to stay relevant 01:02:30 Unpacking the CEO-CRO dynamic Stevie Case is the CRO of Vanta, the trust management platform serving everyone from founders to Fortune 100 CISOs. A former pro-video gamer who stumbled into sales through a mentor's bet, Stevie has built one of the most unconventional paths to the C-suite in tech. In this episode, she unpacks why early revenue hires fail, what separates a true CRO from a VP of Sales, and why she believes fewer than 10% of current CROs will thrive by 2028.

In today's episode, we discuss:

  • Why early revenue hires fail
  • What a top 1% CRO actually does
  • The scaling mistake Stevie made by copying Twilio's playbook at Vanta
  • Why Vanta remains 100% sales-led at every segment
  • AI vs. humans in go-to-market

References:

Where to find Stevie:

Where to find Brett:

Where to find First Round Capital:

Timestamps:

00:00 Why early revenue hires fail

02:23 Who to hire at $5M in revenue

04:16 Coin-operated sellers vs. long-term builders

05:57 What excellence looks like in the CRO role

07:44 Metrics, confidence, and velocity

12:04 Should CROs lead sales?

14:39 From shy seller to revenue leader

16:36 Learning to scale at Twilio

17:44 "There is no CRO playbook"

19:58 Stevie's scaling mistake at Vanta

22:16 Why Vanta stays 100% sales-led

23:16 The value of planning 24-26 months ahead

29:54 When trusting intuition was the wrong call

30:49 Do humans still have a place in the future of GTM?

33:33 Stevie's leadership non-negotiables

36:36 The myth of hiring for industry expertise

40:00 What stays centralized in a 600-person company

47:09 The hidden leverage of a customer's first 30 days

53:42 Why the CRO role will face enormous changes by 2028

58:42 What leaders must do now to stay relevant

01:02:30 Unpacking the CEO-CRO dynamic

]]> 4275 Figma is not the source of truth | Ryan Lucas (VP of Design, Rippling) In the second Executive Function episode, Brett sits down with Ryan Lucas, VP of Design at Rippling. Before Rippling, Ryan led design at Retool and co-founded multiple startups, bringing a rare founder's perspective to design leadership. A trained industrial designer, Ryan traces the roots of modern software design back 2,000 years to make the case that products must be useful, usable, and desirable - and above all, used. In today's episode, we discuss: Why design leaders who stop designing stop leading The four pillars every design manager must master How to delegate when you're a perfectionist Why leaders need strong opinions How to scale good judgment What Rippling's operating system teaches about speed and commitments References: Airbnb: https://www.airbnb.com/ Amazon: https://www.amazon.com/ Apple: https://www.apple.com/ Asana: https://www.asana.com/ Brian Chesky: https://www.linkedin.com/in/brianchesky/ CrossFit: https://www.crossfit.com/ Figma: https://www.figma.com/ Honeywell: https://www.honeywell.com/ Liz Sanders: https://www.linkedin.com/in/sandersliz/ Nest: https://store.google.com/category/google_nest Notion: https://www.notion.so/ Parker Conrad: https://www.linkedin.com/in/parkerconrad/ Patrick Collison: https://www.linkedin.com/in/patrickcollison/ Retool: https://retool.com/ Rippling: https://www.rippling.com/ Stripe: https://www.stripe.com/ Where to find Ryan: LinkedIn: https://www.linkedin.com/in/ryanwlucas/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 00:00 Intro 00:08 What design actually does at a software company 01:40 The roots of design: from industrial design to software 03:29 Useful, usable, desirable — and used 04:49 How design relates to engineering, product, and marketing 08:15 Measuring success as a design leader 12:40 The gap between director and VP-level design leadership 14:23 Why great design leaders jump up and down in altitude 19:26 The four pillars every design manager must master 21:34 Over-indexing on quality and the perfectionist trap 25:11 When lowering the quality bar actually cost the business 27:53 How to build judgment through pattern matching 31:25 How Ryan's design team differs from the rest 34:31 Why Figma is not the source of truth 36:32 How Ryan spends his week: recruiting, crits, and staff meetings 38:39 The "Do/Try/Consider" framework 42:12 The most important decisions of the past year 44:05 Should one-on-ones exist? 46:45 How to scale judgment 50:49 What to look for when hiring your first design leader 54:54 Advice for young designers who want to lead 58:24 Demanding yet supportive: A balanced management style 01:02:43 What Rippling's operating system teaches about execution Thu, 12 Feb 2026 12:00:00 -0000 full First Round In the second Executive Function episode, Brett sits down with Ryan Lucas, VP of Design at Rippling. Before Rippling, Ryan led design at Retool and co-founded multiple startups, bringing a rare founder's perspective to design leadership. A trained industrial designer, Ryan traces the roots of modern software design back 2,000 years to make the case that products must be useful, usable, and desirable - and above all, used. In today's episode, we discuss: Why design leaders who stop designing stop leading The four pillars every design manager must master How to delegate when you're a perfectionist Why leaders need strong opinions How to scale good judgment What Rippling's operating system teaches about speed and commitments References: Airbnb: https://www.airbnb.com/ Amazon: https://www.amazon.com/ Apple: https://www.apple.com/ Asana: https://www.asana.com/ Brian Chesky: https://www.linkedin.com/in/brianchesky/ CrossFit: https://www.crossfit.com/ Figma: https://www.figma.com/ Honeywell: https://www.honeywell.com/ Liz Sanders: https://www.linkedin.com/in/sandersliz/ Nest: https://store.google.com/category/google_nest Notion: https://www.notion.so/ Parker Conrad: https://www.linkedin.com/in/parkerconrad/ Patrick Collison: https://www.linkedin.com/in/patrickcollison/ Retool: https://retool.com/ Rippling: https://www.rippling.com/ Stripe: https://www.stripe.com/ Where to find Ryan: LinkedIn: https://www.linkedin.com/in/ryanwlucas/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: 00:00 Intro 00:08 What design actually does at a software company 01:40 The roots of design: from industrial design to software 03:29 Useful, usable, desirable — and used 04:49 How design relates to engineering, product, and marketing 08:15 Measuring success as a design leader 12:40 The gap between director and VP-level design leadership 14:23 Why great design leaders jump up and down in altitude 19:26 The four pillars every design manager must master 21:34 Over-indexing on quality and the perfectionist trap 25:11 When lowering the quality bar actually cost the business 27:53 How to build judgment through pattern matching 31:25 How Ryan's design team differs from the rest 34:31 Why Figma is not the source of truth 36:32 How Ryan spends his week: recruiting, crits, and staff meetings 38:39 The "Do/Try/Consider" framework 42:12 The most important decisions of the past year 44:05 Should one-on-ones exist? 46:45 How to scale judgment 50:49 What to look for when hiring your first design leader 54:54 Advice for young designers who want to lead 58:24 Demanding yet supportive: A balanced management style 01:02:43 What Rippling's operating system teaches about execution In the second Executive Function episode, Brett sits down with Ryan Lucas, VP of Design at Rippling. Before Rippling, Ryan led design at Retool and co-founded multiple startups, bringing a rare founder's perspective to design leadership. A trained industrial designer, Ryan traces the roots of modern software design back 2,000 years to make the case that products must be useful, usable, and desirable - and above all, used.

In today's episode, we discuss:

  • Why design leaders who stop designing stop leading
  • The four pillars every design manager must master
  • How to delegate when you're a perfectionist
  • Why leaders need strong opinions
  • How to scale good judgment
  • What Rippling's operating system teaches about speed and commitments

References:

Where to find Ryan:

Where to find Brett:

Where to find First Round Capital:

Timestamps:

00:00 Intro

00:08 What design actually does at a software company

01:40 The roots of design: from industrial design to software

03:29 Useful, usable, desirable — and used

04:49 How design relates to engineering, product, and marketing

08:15 Measuring success as a design leader

12:40 The gap between director and VP-level design leadership

14:23 Why great design leaders jump up and down in altitude

19:26 The four pillars every design manager must master

21:34 Over-indexing on quality and the perfectionist trap

25:11 When lowering the quality bar actually cost the business

27:53 How to build judgment through pattern matching

31:25 How Ryan's design team differs from the rest

34:31 Why Figma is not the source of truth

36:32 How Ryan spends his week: recruiting, crits, and staff meetings

38:39 The "Do/Try/Consider" framework

42:12 The most important decisions of the past year

44:05 Should one-on-ones exist?

46:45 How to scale judgment

50:49 What to look for when hiring your first design leader

54:54 Advice for young designers who want to lead

58:24 Demanding yet supportive: A balanced management style

01:02:43 What Rippling's operating system teaches about execution

]]> 3974 Executive Function: Building systems that can make decisions without you | Jeanne DeWitt Grosser (COO, Vercel) In the first Executive Function episode, Brett sits down with Jeanne De Witt Grosser, Chief Operating Officer at Vercel. Before Vercel, Jeanne spent nearly a decade at Stripe, where she built and scaled global revenue teams and led product partnerships. In this conversation, she unpacks what separates good executives from extraordinary ones, shares her rigorous executive hiring process, and reveals the brutally honest performance review feedback she'll never forget. In today's episode, we discuss: What it takes to operate at 30,000 feet and ground level simultaneously The leap from frontline manager to manager of managers Inside Jeanne's executive interview process The inherent value of driver trees for metrics Why context is everything References: Akamai: https://www.akamai.com Claire Johnson: https://www.linkedin.com/in/claire-hughes-johnson-7058/ Culture Amp: https://www.cultureamp.com Guillermo Rauch: https://www.linkedin.com/in/rauchg John Collison: https://www.linkedin.com/in/johnbcollison/ Next.js: https://nextjs.org Nike: https://www.nike.com OpenAI: https://www.openai.com Patrick Collison: https://www.linkedin.com/in/patrickcollison Stanford Graduate School of Business: https://www.gsb.stanford.edu Stripe: https://www.stripe.com Vercel: https://www.vercel.com Where to find Jeanne: LinkedIn: https://www.linkedin.com/in/jeannedewitt Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: (01:17) What separates good executives from extraordinary ones (02:48) How leadership changes as companies scale (04:15) What an executive is actually accountable for (06:11) The leap most rising leaders never make (07:52) When to dive deep vs. when to step back (10:09) Teaching people to think like you do (11:56) Creating a shared language across the business (13:52) What a COO job description actually looks like (17:20) The upside of owning the full customer experience (19:10) Why marketing rolls up under a COO (21:06) Being demanding and supportive at the same time (22:33) Inside the executive interview process (27:35) The workshop prompts that reveal everything (30:11) The common thread in failed executive hires (36:36) Metrics: the driver tree philosophy (43:04 What a collaborative exec team looks like (57:08) How Stripe got 30 people to operate as one team (1:03:50) Working yourself out of a job (1:10:32) The review feedback you can't unhear Thu, 05 Feb 2026 14:47:00 -0000 full First Round In the first Executive Function episode, Brett sits down with Jeanne De Witt Grosser, Chief Operating Officer at Vercel. Before Vercel, Jeanne spent nearly a decade at Stripe, where she built and scaled global revenue teams and led product partnerships. In this conversation, she unpacks what separates good executives from extraordinary ones, shares her rigorous executive hiring process, and reveals the brutally honest performance review feedback she'll never forget. In today's episode, we discuss: What it takes to operate at 30,000 feet and ground level simultaneously The leap from frontline manager to manager of managers Inside Jeanne's executive interview process The inherent value of driver trees for metrics Why context is everything References: Akamai: https://www.akamai.com Claire Johnson: https://www.linkedin.com/in/claire-hughes-johnson-7058/ Culture Amp: https://www.cultureamp.com Guillermo Rauch: https://www.linkedin.com/in/rauchg John Collison: https://www.linkedin.com/in/johnbcollison/ Next.js: https://nextjs.org Nike: https://www.nike.com OpenAI: https://www.openai.com Patrick Collison: https://www.linkedin.com/in/patrickcollison Stanford Graduate School of Business: https://www.gsb.stanford.edu Stripe: https://www.stripe.com Vercel: https://www.vercel.com Where to find Jeanne: LinkedIn: https://www.linkedin.com/in/jeannedewitt Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: (01:17) What separates good executives from extraordinary ones (02:48) How leadership changes as companies scale (04:15) What an executive is actually accountable for (06:11) The leap most rising leaders never make (07:52) When to dive deep vs. when to step back (10:09) Teaching people to think like you do (11:56) Creating a shared language across the business (13:52) What a COO job description actually looks like (17:20) The upside of owning the full customer experience (19:10) Why marketing rolls up under a COO (21:06) Being demanding and supportive at the same time (22:33) Inside the executive interview process (27:35) The workshop prompts that reveal everything (30:11) The common thread in failed executive hires (36:36) Metrics: the driver tree philosophy (43:04 What a collaborative exec team looks like (57:08) How Stripe got 30 people to operate as one team (1:03:50) Working yourself out of a job (1:10:32) The review feedback you can't unhear In the first Executive Function episode, Brett sits down with Jeanne De Witt Grosser, Chief Operating Officer at Vercel. Before Vercel, Jeanne spent nearly a decade at Stripe, where she built and scaled global revenue teams and led product partnerships. In this conversation, she unpacks what separates good executives from extraordinary ones, shares her rigorous executive hiring process, and reveals the brutally honest performance review feedback she'll never forget.

In today's episode, we discuss:

  • What it takes to operate at 30,000 feet and ground level simultaneously
  • The leap from frontline manager to manager of managers
  • Inside Jeanne's executive interview process
  • The inherent value of driver trees for metrics
  • Why context is everything


References:


Where to find Jeanne:


Where to find Brett:


Where to find First Round Capital:


Timestamps:

(01:17) What separates good executives from extraordinary ones

(02:48) How leadership changes as companies scale

(04:15) What an executive is actually accountable for

(06:11) The leap most rising leaders never make

(07:52) When to dive deep vs. when to step back

(10:09) Teaching people to think like you do

(11:56) Creating a shared language across the business

(13:52) What a COO job description actually looks like

(17:20) The upside of owning the full customer experience

(19:10) Why marketing rolls up under a COO

(21:06) Being demanding and supportive at the same time

(22:33) Inside the executive interview process

(27:35) The workshop prompts that reveal everything

(30:11) The common thread in failed executive hires

(36:36) Metrics: the driver tree philosophy

(43:04 What a collaborative exec team looks like

(57:08) How Stripe got 30 people to operate as one team

(1:03:50) Working yourself out of a job

(1:10:32) The review feedback you can't unhear

]]> 4551 Building Meter for decades, not an exit | Anil Varanasi (Co-founder and CEO) Anil Varanasi is the co-founder and CEO of Meter, which provides full-stack networking infrastructure as a service for businesses. Since founding Meter with his brother Sunil in 2015, Anil has been playing a distinctly long game in one of the most entrenched markets in technology, betting on vertical integration, business model innovation, and a multi-decade time horizon. In this conversation, he unpacks Meter’s origin story, from four-plus years of heads-down R&D, and shares how his unconventional approach to planning, management, and pace keeps him excited to run the company for decades. In today’s episode, we discuss: Why Anil thinks in 25-year horizons How operating in a monopolistic market shaped Meter’s approach Why Meter scrapped a year of OS work during the R&D phase How Meter is rethinking networking’s business model Surviving COVID, Apple’s M1 transition, and “a thousand bad days” Anil’s contrarian views on planning, OKRs, and management How founders can build companies they’ll want to run for decades Where to find Anil: LinkedIn: https://www.linkedin.com/in/anilcv/ Twitter/X: https://x.com/acv Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: ADT: ⁠https://www.adt.com⁠ Alex Honnold: ⁠https://www.alexhonnold.com⁠ Alex Tabarrok: ⁠https://x.com/ATabarrok⁠ ⁠alarm.com⁠: ⁠https://www.alarm.com⁠ Andreessen Horowitz (a16z): ⁠https://a16z.com⁠ Apple: ⁠https://www.apple.com⁠ Bloomberg: ⁠https://www.bloomberg.com⁠ Bryan Caplan: ⁠http://www.bcaplan.com/⁠ Cisco: ⁠https://www.cisco.com⁠ Coca-Cola: ⁠https://www.coca-colacompany.com⁠ George Mason University (GMU): ⁠https://www.gmu.edu⁠ Intel: ⁠https://www.intel.com⁠ Julia Galef: ⁠https://x.com/juliagalef⁠ Martin Casado: ⁠https://www.linkedin.com/in/martincasado/⁠ Meraki: ⁠https://meraki.cisco.com⁠ Meter: ⁠https://www.meter.com⁠ Michela Giorcelli: ⁠https://x.com/M_Giorcelli⁠ Nicholas Bloom: ⁠https://www.linkedin.com/in/nick-bloom-stanford/⁠ Raffaella Sadun: ⁠https://www.linkedin.com/in/raffaella-sadun-3a182225/⁠ Sanjit Biswas: ⁠https://www.linkedin.com/in/sanjitbiswas/⁠ Sunil Varanasi: ⁠https://www.linkedin.com/in/sunil-varanasi-662a01253/⁠ Tyler Cowen: ⁠https://www.linkedin.com/in/tyler-cowen-166718/⁠ Twitch: ⁠https://www.twitch.tv⁠ Timestamps: (01:27) Meter’s unusual timeframes (04:06) “We don’t do OKRs” (06:32) How to plan without planning (08:31) Track your unhappy customers (11:43) How Meter’s journey began (15:02) Dissecting the 2010s SaaS boom (17:06) The networking industry trap (21:44) Meter’s first roadblock (22:07) Why Shenzhen accelerated Meter’s progress (26:29) The process to get a sales-ready product (31:02) Why you should own the full stack (32:45) The surprising thing you should innovate (35:03) Avoiding the one-trick pony trap (37:39) The secret to finding an excellent market (43:48) How COVID’s constraints propelled growth (48:25) Why founders need to know their customers (49:34) Why Meter didn’t sell via traditional channels (51:44) You need “seller-market fit” (54:51) The danger of meta-work (56:25) Decoupling management from authority (1:02:17) When the person is the problem (1:05:05) The inherent value of going slowly (1:09:41) Running a company for as long as possible Wed, 10 Dec 2025 12:00:00 -0000 full First Round Anil Varanasi is the co-founder and CEO of Meter, which provides full-stack networking infrastructure as a service for businesses. Since founding Meter with his brother Sunil in 2015, Anil has been playing a distinctly long game in one of the most entrenched markets in technology, betting on vertical integration, business model innovation, and a multi-decade time horizon. In this conversation, he unpacks Meter’s origin story, from four-plus years of heads-down R&D, and shares how his unconventional approach to planning, management, and pace keeps him excited to run the company for decades. In today’s episode, we discuss: Why Anil thinks in 25-year horizons How operating in a monopolistic market shaped Meter’s approach Why Meter scrapped a year of OS work during the R&D phase How Meter is rethinking networking’s business model Surviving COVID, Apple’s M1 transition, and “a thousand bad days” Anil’s contrarian views on planning, OKRs, and management How founders can build companies they’ll want to run for decades Where to find Anil: LinkedIn: https://www.linkedin.com/in/anilcv/ Twitter/X: https://x.com/acv Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: ADT: ⁠https://www.adt.com⁠ Alex Honnold: ⁠https://www.alexhonnold.com⁠ Alex Tabarrok: ⁠https://x.com/ATabarrok⁠ ⁠alarm.com⁠: ⁠https://www.alarm.com⁠ Andreessen Horowitz (a16z): ⁠https://a16z.com⁠ Apple: ⁠https://www.apple.com⁠ Bloomberg: ⁠https://www.bloomberg.com⁠ Bryan Caplan: ⁠http://www.bcaplan.com/⁠ Cisco: ⁠https://www.cisco.com⁠ Coca-Cola: ⁠https://www.coca-colacompany.com⁠ George Mason University (GMU): ⁠https://www.gmu.edu⁠ Intel: ⁠https://www.intel.com⁠ Julia Galef: ⁠https://x.com/juliagalef⁠ Martin Casado: ⁠https://www.linkedin.com/in/martincasado/⁠ Meraki: ⁠https://meraki.cisco.com⁠ Meter: ⁠https://www.meter.com⁠ Michela Giorcelli: ⁠https://x.com/M_Giorcelli⁠ Nicholas Bloom: ⁠https://www.linkedin.com/in/nick-bloom-stanford/⁠ Raffaella Sadun: ⁠https://www.linkedin.com/in/raffaella-sadun-3a182225/⁠ Sanjit Biswas: ⁠https://www.linkedin.com/in/sanjitbiswas/⁠ Sunil Varanasi: ⁠https://www.linkedin.com/in/sunil-varanasi-662a01253/⁠ Tyler Cowen: ⁠https://www.linkedin.com/in/tyler-cowen-166718/⁠ Twitch: ⁠https://www.twitch.tv⁠ Timestamps: (01:27) Meter’s unusual timeframes (04:06) “We don’t do OKRs” (06:32) How to plan without planning (08:31) Track your unhappy customers (11:43) How Meter’s journey began (15:02) Dissecting the 2010s SaaS boom (17:06) The networking industry trap (21:44) Meter’s first roadblock (22:07) Why Shenzhen accelerated Meter’s progress (26:29) The process to get a sales-ready product (31:02) Why you should own the full stack (32:45) The surprising thing you should innovate (35:03) Avoiding the one-trick pony trap (37:39) The secret to finding an excellent market (43:48) How COVID’s constraints propelled growth (48:25) Why founders need to know their customers (49:34) Why Meter didn’t sell via traditional channels (51:44) You need “seller-market fit” (54:51) The danger of meta-work (56:25) Decoupling management from authority (1:02:17) When the person is the problem (1:05:05) The inherent value of going slowly (1:09:41) Running a company for as long as possible Anil Varanasi is the co-founder and CEO of Meter, which provides full-stack networking infrastructure as a service for businesses. Since founding Meter with his brother Sunil in 2015, Anil has been playing a distinctly long game in one of the most entrenched markets in technology, betting on vertical integration, business model innovation, and a multi-decade time horizon. In this conversation, he unpacks Meter’s origin story, from four-plus years of heads-down R&D, and shares how his unconventional approach to planning, management, and pace keeps him excited to run the company for decades.

In today’s episode, we discuss:

  • Why Anil thinks in 25-year horizons
  • How operating in a monopolistic market shaped Meter’s approach
  • Why Meter scrapped a year of OS work during the R&D phase
  • How Meter is rethinking networking’s business model
  • Surviving COVID, Apple’s M1 transition, and “a thousand bad days”
  • Anil’s contrarian views on planning, OKRs, and management
  • How founders can build companies they’ll want to run for decades


Where to find Anil:


Where to find Brett:


Where to find First Round Capital:


References:


Timestamps:

(01:27) Meter’s unusual timeframes

(04:06) “We don’t do OKRs”

(06:32) How to plan without planning

(08:31) Track your unhappy customers

(11:43) How Meter’s journey began

(15:02) Dissecting the 2010s SaaS boom

(17:06) The networking industry trap

(21:44) Meter’s first roadblock

(22:07) Why Shenzhen accelerated Meter’s progress

(26:29) The process to get a sales-ready product

(31:02) Why you should own the full stack

(32:45) The surprising thing you should innovate

(35:03) Avoiding the one-trick pony trap

(37:39) The secret to finding an excellent market

(43:48) How COVID’s constraints propelled growth

(48:25) Why founders need to know their customers

(49:34) Why Meter didn’t sell via traditional channels

(51:44) You need “seller-market fit”

(54:51) The danger of meta-work

(56:25) Decoupling management from authority

(1:02:17) When the person is the problem

(1:05:05) The inherent value of going slowly

(1:09:41) Running a company for as long as possible

]]> 4493 How Harness runs 16 “startups within a startup” at scale | Jyoti Bansal (Co-founder and CEO) Jyoti Bansal is the co-founder and CEO of Harness, the software delivery platform used by thousands of engineering teams, and previously founded AppDynamics, which he led from inception to a multibillion-dollar acquisition by Cisco. In this episode, Jyoti unpacks what it really takes to move from mid-market to enterprise, why he thinks in terms of “product-market-sales fit,” and how he structures Harness as a collection of “startups within a startup” to launch multiple “best-of-breed” products. In today’s episode, we discuss: Why companies get stuck in the mid-market and struggle to move up into enterprise Why Jyoti deliberately lost Netflix as their customer The difference between product-market-sales fit, and product-market-fit How to build a scalable, capacity-driven go-to-market machine (instead of chasing deals) Diagnosing whether you have a product problem or a distribution problem How to hire and evaluate your first head of sales and top sales leaders Why Jyoti sold AppDynamics three days before IPO The “binary differentiator” rule for launching new products into crowded markets Why Harness runs 16 product lines under one roof Where to find Jyoti: LinkedIn: https://www.linkedin.com/in/jyotibansal/ Twitter/X: https://x.com/jyotibansalsf Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: Amazon: https://www.amazon.com/ AppDynamics: https://www.appdynamics.com/ Barclays: https://home.barclays/ BIG Labs: https://www.biglabs.com/ Carlos Delatorre: https://www.linkedin.com/in/cadelatorre/ Charles Schwab: https://www.schwab.com/ Cisco: https://www.cisco.com/ Citi: https://www.citi.com/ Cloudability: https://www.apptio.com/products/cloudability/ Datadog: https://www.datadoghq.com/ Dynatrace: https://www.dynatrace.com/ Harness: https://www.harness.io/ Jeff Bezos: https://x.com/JeffBezos Microsoft: https://www.microsoft.com/ Nasdaq: https://www.nasdaq.com/ Netflix: https://www.netflix.com/ New Relic: https://newrelic.com/ Salesforce: https://www.salesforce.com/ Splunk: https://www.splunk.com/ Traceable: https://www.traceable.ai/ Unusual Ventures: https://www.unusual.vc/ VMware: https://www.vmware.com/ Timestamps: (01:48) Why do companies get stuck in the mid-market? (05:09) Designing a product for enterprise and mid-market (07:19) Why Jyoti lost Netflix as a customer - on purpose (10:18) Becoming a scalable GTM organization (12:32) The real signs of product-market fit (14:04) Have you delivered the value? (15:46) How to hire your first sales team (19:59) The four signs of excellent sales leaders (23:16) How to interview a sales leader (27:51) Where Jyoti developed his commercial taste (29:37) Why early founders need to learn sales (32:02) How AppDynamics began (36:36) Why Jyoti sold three days pre-IPO (41:55) What does a healthy board look like? (44:23) How Jyoti perceives competition (46:18) Why you need a binary differentiator (49:53) How to launch multiple products (52:00) “We need to be best of breed” (57:38) Why PMs are like mini-entrepreneurs (1:00:20) The startup within a startup (1:02:45) A culture of continuous improvement Wed, 19 Nov 2025 12:00:00 -0000 full First Round Jyoti Bansal is the co-founder and CEO of Harness, the software delivery platform used by thousands of engineering teams, and previously founded AppDynamics, which he led from inception to a multibillion-dollar acquisition by Cisco. In this episode, Jyoti unpacks what it really takes to move from mid-market to enterprise, why he thinks in terms of “product-market-sales fit,” and how he structures Harness as a collection of “startups within a startup” to launch multiple “best-of-breed” products. In today’s episode, we discuss: Why companies get stuck in the mid-market and struggle to move up into enterprise Why Jyoti deliberately lost Netflix as their customer The difference between product-market-sales fit, and product-market-fit How to build a scalable, capacity-driven go-to-market machine (instead of chasing deals) Diagnosing whether you have a product problem or a distribution problem How to hire and evaluate your first head of sales and top sales leaders Why Jyoti sold AppDynamics three days before IPO The “binary differentiator” rule for launching new products into crowded markets Why Harness runs 16 product lines under one roof Where to find Jyoti: LinkedIn: https://www.linkedin.com/in/jyotibansal/ Twitter/X: https://x.com/jyotibansalsf Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: Amazon: https://www.amazon.com/ AppDynamics: https://www.appdynamics.com/ Barclays: https://home.barclays/ BIG Labs: https://www.biglabs.com/ Carlos Delatorre: https://www.linkedin.com/in/cadelatorre/ Charles Schwab: https://www.schwab.com/ Cisco: https://www.cisco.com/ Citi: https://www.citi.com/ Cloudability: https://www.apptio.com/products/cloudability/ Datadog: https://www.datadoghq.com/ Dynatrace: https://www.dynatrace.com/ Harness: https://www.harness.io/ Jeff Bezos: https://x.com/JeffBezos Microsoft: https://www.microsoft.com/ Nasdaq: https://www.nasdaq.com/ Netflix: https://www.netflix.com/ New Relic: https://newrelic.com/ Salesforce: https://www.salesforce.com/ Splunk: https://www.splunk.com/ Traceable: https://www.traceable.ai/ Unusual Ventures: https://www.unusual.vc/ VMware: https://www.vmware.com/ Timestamps: (01:48) Why do companies get stuck in the mid-market? (05:09) Designing a product for enterprise and mid-market (07:19) Why Jyoti lost Netflix as a customer - on purpose (10:18) Becoming a scalable GTM organization (12:32) The real signs of product-market fit (14:04) Have you delivered the value? (15:46) How to hire your first sales team (19:59) The four signs of excellent sales leaders (23:16) How to interview a sales leader (27:51) Where Jyoti developed his commercial taste (29:37) Why early founders need to learn sales (32:02) How AppDynamics began (36:36) Why Jyoti sold three days pre-IPO (41:55) What does a healthy board look like? (44:23) How Jyoti perceives competition (46:18) Why you need a binary differentiator (49:53) How to launch multiple products (52:00) “We need to be best of breed” (57:38) Why PMs are like mini-entrepreneurs (1:00:20) The startup within a startup (1:02:45) A culture of continuous improvement Jyoti Bansal is the co-founder and CEO of Harness, the software delivery platform used by thousands of engineering teams, and previously founded AppDynamics, which he led from inception to a multibillion-dollar acquisition by Cisco. In this episode, Jyoti unpacks what it really takes to move from mid-market to enterprise, why he thinks in terms of “product-market-sales fit,” and how he structures Harness as a collection of “startups within a startup” to launch multiple “best-of-breed” products.

In today’s episode, we discuss:

  • Why companies get stuck in the mid-market and struggle to move up into enterprise
  • Why Jyoti deliberately lost Netflix as their customer
  • The difference between product-market-sales fit, and product-market-fit
  • How to build a scalable, capacity-driven go-to-market machine (instead of chasing deals)
  • Diagnosing whether you have a product problem or a distribution problem
  • How to hire and evaluate your first head of sales and top sales leaders
  • Why Jyoti sold AppDynamics three days before IPO
  • The “binary differentiator” rule for launching new products into crowded markets
  • Why Harness runs 16 product lines under one roof


Where to find Jyoti:


Where to find Brett:


Where to find First Round Capital:


References:


Timestamps:

(01:48) Why do companies get stuck in the mid-market?

(05:09) Designing a product for enterprise and mid-market

(07:19) Why Jyoti lost Netflix as a customer - on purpose

(10:18) Becoming a scalable GTM organization

(12:32) The real signs of product-market fit

(14:04) Have you delivered the value?

(15:46) How to hire your first sales team

(19:59) The four signs of excellent sales leaders

(23:16) How to interview a sales leader

(27:51) Where Jyoti developed his commercial taste

(29:37) Why early founders need to learn sales

(32:02) How AppDynamics began

(36:36) Why Jyoti sold three days pre-IPO

(41:55) What does a healthy board look like?

(44:23) How Jyoti perceives competition

(46:18) Why you need a binary differentiator

(49:53) How to launch multiple products

(52:00) “We need to be best of breed”

(57:38) Why PMs are like mini-entrepreneurs

(1:00:20) The startup within a startup

(1:02:45) A culture of continuous improvement

]]> 3917 How to build a company you’ll run forever | Zack Kanter (Founder and CEO of Stedi) Zack Kanter is the founder and CEO of Stedi, an API-first healthcare clearinghouse. After bootstrapping a wildly profitable auto-parts business, he sold it to tackle "the most complicated problem" he'd ever encountered: business-to-business transaction exchange. He spent years building EDI infrastructure, threw away the entire codebase eight times, and found extraordinary traction in healthcare. Stedi recently raised a $70M Series B co-led by Stripe and Addition. In this conversation, Brett and Zack discuss why venture capital means "going pro," why execution is never actually a moat, and how "eating glass" became Stedi's competitive advantage. In today’s episode, we discuss: How 16-year-old Zack turned $2,500 into a wholesale empire Why bootstrapping means being "constrained by capital" and how VC removes that ceiling Why Zack rebuilt their EDI product eight times before launch The snake swallowing a deer: what extreme product-market fit really looks like What software companies can learn from discount retail and Toyota Why Stedi’s new hires are told "everything’s your fault now" And much more Where to find Zack: LinkedIn: https://www.linkedin.com/in/zkanter Twitter/X: https://x.com/zackkanter Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: Aetna: https://www.aetna.com/ Amazon: https://www.amazon.com/ AWS: https://aws.amazon.com/ Blue Cross Blue Shield: https://www.bcbs.com/ Change Healthcare: https://www.changehealthcare.com/ Cigna: https://www.cigna.com/ Clay: https://www.clay.com/ Costco: https://www.costco.com/ Ford Motor Company: https://www.ford.com/ GM: https://www.gm.com/ HIPAA overview (HHS): https://www.hhs.gov/hipaa/index.html Jeff Bezos: https://x.com/JeffBezos Kanban / TPS (Toyota): https://global.toyota/en/company/vision-and-philosophy/production-system Microsoft Teams: https://www.microsoft.com/microsoft-teams NetSuite: https://www.netsuite.com/ O’Reilly Auto Parts: https://www.oreillyauto.com/ Peter Thiel: https://x.com/peterthiel Porter’s five forces: https://www.isc.hbs.edu/strategy/pages/the-five-forces.aspx "Reality has a surprising amount of detail": https://johnsalvatier.org/blog/2017/reality-has-a-surprising-amount-of-detail Slack: https://slack.com/ Stedi: https://www.stedi.com/ Summit Racing: https://www.summitracing.com/ Target: https://www.target.com/ Walmart: https://www.walmart.com/ Zapier: https://zapier.com/ Timestamps: (01:24) Zack’s first business (08:54) Why the first customer is tricky (10:12) The downside of bootstrapping (11:42) Why venture capital is like “going pro” (14:20) The confusion between ownership vs. control (16:08) Building a company you don’t want to leave (20:46) Do things better than other people (24:49) Stedi’s early years (31:43) Physical vs. digital product-market fit (34:41) How Stedi scaled decision-making (40:08) Stedi’s journey to product-market fit (45:22) Finding founder-approach fit (50:42) “All software is a cascade of miracles” (52:52) The surprising lessons from discount retail (57:50) How the Toyota production system influences software (1:01:31) What it means to be a high-agency person (1:03:09) The core trait Zack looks for when hiring (1:02:57) Maintaining conviction in unconventional practice (1:14:19) When should you start to hire managers? (1:17:42) “Reality has a surprising amount of detail” Thu, 06 Nov 2025 12:00:00 -0000 full First Round Zack Kanter is the founder and CEO of Stedi, an API-first healthcare clearinghouse. After bootstrapping a wildly profitable auto-parts business, he sold it to tackle "the most complicated problem" he'd ever encountered: business-to-business transaction exchange. He spent years building EDI infrastructure, threw away the entire codebase eight times, and found extraordinary traction in healthcare. Stedi recently raised a $70M Series B co-led by Stripe and Addition. In this conversation, Brett and Zack discuss why venture capital means "going pro," why execution is never actually a moat, and how "eating glass" became Stedi's competitive advantage. In today’s episode, we discuss: How 16-year-old Zack turned $2,500 into a wholesale empire Why bootstrapping means being "constrained by capital" and how VC removes that ceiling Why Zack rebuilt their EDI product eight times before launch The snake swallowing a deer: what extreme product-market fit really looks like What software companies can learn from discount retail and Toyota Why Stedi’s new hires are told "everything’s your fault now" And much more Where to find Zack: LinkedIn: https://www.linkedin.com/in/zkanter Twitter/X: https://x.com/zackkanter Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: Aetna: https://www.aetna.com/ Amazon: https://www.amazon.com/ AWS: https://aws.amazon.com/ Blue Cross Blue Shield: https://www.bcbs.com/ Change Healthcare: https://www.changehealthcare.com/ Cigna: https://www.cigna.com/ Clay: https://www.clay.com/ Costco: https://www.costco.com/ Ford Motor Company: https://www.ford.com/ GM: https://www.gm.com/ HIPAA overview (HHS): https://www.hhs.gov/hipaa/index.html Jeff Bezos: https://x.com/JeffBezos Kanban / TPS (Toyota): https://global.toyota/en/company/vision-and-philosophy/production-system Microsoft Teams: https://www.microsoft.com/microsoft-teams NetSuite: https://www.netsuite.com/ O’Reilly Auto Parts: https://www.oreillyauto.com/ Peter Thiel: https://x.com/peterthiel Porter’s five forces: https://www.isc.hbs.edu/strategy/pages/the-five-forces.aspx "Reality has a surprising amount of detail": https://johnsalvatier.org/blog/2017/reality-has-a-surprising-amount-of-detail Slack: https://slack.com/ Stedi: https://www.stedi.com/ Summit Racing: https://www.summitracing.com/ Target: https://www.target.com/ Walmart: https://www.walmart.com/ Zapier: https://zapier.com/ Timestamps: (01:24) Zack’s first business (08:54) Why the first customer is tricky (10:12) The downside of bootstrapping (11:42) Why venture capital is like “going pro” (14:20) The confusion between ownership vs. control (16:08) Building a company you don’t want to leave (20:46) Do things better than other people (24:49) Stedi’s early years (31:43) Physical vs. digital product-market fit (34:41) How Stedi scaled decision-making (40:08) Stedi’s journey to product-market fit (45:22) Finding founder-approach fit (50:42) “All software is a cascade of miracles” (52:52) The surprising lessons from discount retail (57:50) How the Toyota production system influences software (1:01:31) What it means to be a high-agency person (1:03:09) The core trait Zack looks for when hiring (1:02:57) Maintaining conviction in unconventional practice (1:14:19) When should you start to hire managers? (1:17:42) “Reality has a surprising amount of detail” Zack Kanter is the founder and CEO of Stedi, an API-first healthcare clearinghouse. After bootstrapping a wildly profitable auto-parts business, he sold it to tackle "the most complicated problem" he'd ever encountered: business-to-business transaction exchange. He spent years building EDI infrastructure, threw away the entire codebase eight times, and found extraordinary traction in healthcare. Stedi recently raised a $70M Series B co-led by Stripe and Addition. In this conversation, Brett and Zack discuss why venture capital means "going pro," why execution is never actually a moat, and how "eating glass" became Stedi's competitive advantage.


In today’s episode, we discuss:

  • How 16-year-old Zack turned $2,500 into a wholesale empire
  • Why bootstrapping means being "constrained by capital" and how VC removes that ceiling
  • Why Zack rebuilt their EDI product eight times before launch
  • The snake swallowing a deer: what extreme product-market fit really looks like
  • What software companies can learn from discount retail and Toyota
  • Why Stedi’s new hires are told "everything’s your fault now"
  • And much more


Where to find Zack:

  • LinkedIn: https://www.linkedin.com/in/zkanter
  • Twitter/X: https://x.com/zackkanter


Where to find Brett:

  • LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
  • Twitter/X: https://twitter.com/brettberson


Where to find First Round Capital:

  • Website: https://firstround.com/
  • First Round Review: https://review.firstround.com/
  • Twitter/X: https://twitter.com/firstround
  • YouTube: https://www.youtube.com/@FirstRoundCapital
  • This podcast on all platforms: https://review.firstround.com/podcast


References:

  • Aetna: https://www.aetna.com/
  • Amazon: https://www.amazon.com/
  • AWS: https://aws.amazon.com/
  • Blue Cross Blue Shield: https://www.bcbs.com/
  • Change Healthcare: https://www.changehealthcare.com/
  • Cigna: https://www.cigna.com/
  • Clay: https://www.clay.com/
  • Costco: https://www.costco.com/
  • Ford Motor Company: https://www.ford.com/
  • GM: https://www.gm.com/
  • HIPAA overview (HHS): https://www.hhs.gov/hipaa/index.html
  • Jeff Bezos: https://x.com/JeffBezos
  • Kanban / TPS (Toyota): https://global.toyota/en/company/vision-and-philosophy/production-system
  • Microsoft Teams: https://www.microsoft.com/microsoft-teams
  • NetSuite: https://www.netsuite.com/
  • O’Reilly Auto Parts: https://www.oreillyauto.com/
  • Peter Thiel: https://x.com/peterthiel
  • Porter’s five forces: https://www.isc.hbs.edu/strategy/pages/the-five-forces.aspx
  • "Reality has a surprising amount of detail": https://johnsalvatier.org/blog/2017/reality-has-a-surprising-amount-of-detail
  • Slack: https://slack.com/
  • Stedi: https://www.stedi.com/
  • Summit Racing: https://www.summitracing.com/
  • Target: https://www.target.com/
  • Walmart: https://www.walmart.com/
  • Zapier: https://zapier.com/


Timestamps:

(01:24) Zack’s first business

(08:54) Why the first customer is tricky

(10:12) The downside of bootstrapping

(11:42) Why venture capital is like “going pro”

(14:20) The confusion between ownership vs. control

(16:08) Building a company you don’t want to leave

(20:46) Do things better than other people

(24:49) Stedi’s early years

(31:43) Physical vs. digital product-market fit

(34:41) How Stedi scaled decision-making

(40:08) Stedi’s journey to product-market fit

(45:22) Finding founder-approach fit

(50:42) “All software is a cascade of miracles”

(52:52) The surprising lessons from discount retail

(57:50) How the Toyota production system influences software

(1:01:31) What it means to be a high-agency person

(1:03:09) The core trait Zack looks for when hiring

(1:02:57) Maintaining conviction in unconventional practice

(1:14:19) When should you start to hire managers?

(1:17:42) “Reality has a surprising amount of detail”

]]> 5049 Go hard early: How lessons from Verkada shaped Serval's AI agents for IT teams | Jake Stauch (Founder and CEO) Jake is the founder and CEO of Serval, an AI-driven IT automation and service management platform that just raised $47M in Series A funding this week. Before founding Serval, Jake spent over five years at Verkada, where he led multiple products from 0-1 and helped scale the company across hardware and software. His years at Verkada taught him that winning in enterprise means delivering consumer-quality experiences to business buyers — a lesson that shapes how Serval turns complex IT automation into something that feels magical. In this episode, Jake and Brett dive into the lessons from Verkada that inspired Serval's founding, what it takes to disrupt entrenched enterprise categories, and practical tips for getting deeply embedded with customers and hiring high-quality candidates. In today’s episode, we discuss: Why building “in existing categories” can be more powerful than creating new ones The lessons from Verkada that shaped Serval's platform strategy The customer interview question that unlocked the IT buyer’s hidden pain points How Serval's automation builder uses AI to generate code-based workflows Redefining engineering and PM roles with forward-deployed engineers Keeping the hiring bar high in an AI-native startup Why there’s a “land grab” moment right now in enterprise AI And much more... Where to find Jake: LinkedIn: https://www.linkedin.com/in/jakestauch/ Twitter/X: https://x.com/jakeserval Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: Alex McLeod: https://www.linkedin.com/in/alexmcleodio/ Clay: https://www.clay.com Cloudflare: https://www.cloudflare.com Cursor: https://cursor.sh Filip Kaliszan: https://www.linkedin.com/in/kaliszan/ Hans Robertson: https://www.linkedin.com/in/hansrobertson Linear: https://linear.app Okta: https://www.okta.com Rippling: https://www.rippling.com Serval: https://www.serval.com/ ServiceNow: https://www.servicenow.com Verkada: https://www.verkada.com Workday: https://www.workday.com Timestamps: (02:25) Lessons from holding different product roles (07:29) Turning “hard mode” into a moat (10:49) The early days of Serval (12:59) Scratching the founder itch (14:57) Unconventional interview techniques (17:47) Solving core interview challenges (21:10) Planning the early product roadmap (23:03) The surprising power of patience (26:12) Serval’s impressive technical advantage (27:35) Disrupting legacy incumbents (31:13) Building for mid-market and enterprise (33:35) Serval’s enduring roadmap (36:08) How to sell to an existing market (39:16) The evolving role software plays (43:55) Building for AI that didn’t exist yet (49:49) Serval’s forward-deployed engineers (58:31) The hybrid PM-GM (1:00:27) “You can over-prioritize” (1:02:48) The unexpected value of panic buttons (1:04:50) What Serval looks for in new talent (1:07:01) The ultimate hiring litmus test (1:13:59) Building out Serval’s go-to-market function (1:16:31) The evolving IT market in 2025 Thu, 23 Oct 2025 11:00:00 -0000 full First Round Jake is the founder and CEO of Serval, an AI-driven IT automation and service management platform that just raised $47M in Series A funding this week. Before founding Serval, Jake spent over five years at Verkada, where he led multiple products from 0-1 and helped scale the company across hardware and software. His years at Verkada taught him that winning in enterprise means delivering consumer-quality experiences to business buyers — a lesson that shapes how Serval turns complex IT automation into something that feels magical. In this episode, Jake and Brett dive into the lessons from Verkada that inspired Serval's founding, what it takes to disrupt entrenched enterprise categories, and practical tips for getting deeply embedded with customers and hiring high-quality candidates. In today’s episode, we discuss: Why building “in existing categories” can be more powerful than creating new ones The lessons from Verkada that shaped Serval's platform strategy The customer interview question that unlocked the IT buyer’s hidden pain points How Serval's automation builder uses AI to generate code-based workflows Redefining engineering and PM roles with forward-deployed engineers Keeping the hiring bar high in an AI-native startup Why there’s a “land grab” moment right now in enterprise AI And much more... Where to find Jake: LinkedIn: https://www.linkedin.com/in/jakestauch/ Twitter/X: https://x.com/jakeserval Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: Alex McLeod: https://www.linkedin.com/in/alexmcleodio/ Clay: https://www.clay.com Cloudflare: https://www.cloudflare.com Cursor: https://cursor.sh Filip Kaliszan: https://www.linkedin.com/in/kaliszan/ Hans Robertson: https://www.linkedin.com/in/hansrobertson Linear: https://linear.app Okta: https://www.okta.com Rippling: https://www.rippling.com Serval: https://www.serval.com/ ServiceNow: https://www.servicenow.com Verkada: https://www.verkada.com Workday: https://www.workday.com Timestamps: (02:25) Lessons from holding different product roles (07:29) Turning “hard mode” into a moat (10:49) The early days of Serval (12:59) Scratching the founder itch (14:57) Unconventional interview techniques (17:47) Solving core interview challenges (21:10) Planning the early product roadmap (23:03) The surprising power of patience (26:12) Serval’s impressive technical advantage (27:35) Disrupting legacy incumbents (31:13) Building for mid-market and enterprise (33:35) Serval’s enduring roadmap (36:08) How to sell to an existing market (39:16) The evolving role software plays (43:55) Building for AI that didn’t exist yet (49:49) Serval’s forward-deployed engineers (58:31) The hybrid PM-GM (1:00:27) “You can over-prioritize” (1:02:48) The unexpected value of panic buttons (1:04:50) What Serval looks for in new talent (1:07:01) The ultimate hiring litmus test (1:13:59) Building out Serval’s go-to-market function (1:16:31) The evolving IT market in 2025 Jake is the founder and CEO of Serval, an AI-driven IT automation and service management platform that just raised $47M in Series A funding this week. Before founding Serval, Jake spent over five years at Verkada, where he led multiple products from 0-1 and helped scale the company across hardware and software. His years at Verkada taught him that winning in enterprise means delivering consumer-quality experiences to business buyers — a lesson that shapes how Serval turns complex IT automation into something that feels magical.

In this episode, Jake and Brett dive into the lessons from Verkada that inspired Serval's founding, what it takes to disrupt entrenched enterprise categories, and practical tips for getting deeply embedded with customers and hiring high-quality candidates.


In today’s episode, we discuss:

  • Why building “in existing categories” can be more powerful than creating new ones
  • The lessons from Verkada that shaped Serval's platform strategy
  • The customer interview question that unlocked the IT buyer’s hidden pain points
  • How Serval's automation builder uses AI to generate code-based workflows
  • Redefining engineering and PM roles with forward-deployed engineers
  • Keeping the hiring bar high in an AI-native startup
  • Why there’s a “land grab” moment right now in enterprise AI
  • And much more...

Where to find Jake:


Where to find Brett:


Where to find First Round Capital:


References:


Timestamps:

(02:25) Lessons from holding different product roles

(07:29) Turning “hard mode” into a moat

(10:49) The early days of Serval

(12:59) Scratching the founder itch

(14:57) Unconventional interview techniques

(17:47) Solving core interview challenges

(21:10) Planning the early product roadmap

(23:03) The surprising power of patience

(26:12) Serval’s impressive technical advantage

(27:35) Disrupting legacy incumbents

(31:13) Building for mid-market and enterprise

(33:35) Serval’s enduring roadmap

(36:08) How to sell to an existing market

(39:16) The evolving role software plays

(43:55) Building for AI that didn’t exist yet

(49:49) Serval’s forward-deployed engineers

(58:31) The hybrid PM-GM

(1:00:27) “You can over-prioritize”

(1:02:48) The unexpected value of panic buttons

(1:04:50) What Serval looks for in new talent

(1:07:01) The ultimate hiring litmus test

(1:13:59) Building out Serval’s go-to-market function

(1:16:31) The evolving IT market in 2025

]]> 4981 The pivot that paid off: How fal found explosive growth in generative media | Gorkem Yurtseven (Co-founder and CTO) Gorkem Yurtseven is the co-founder and CTO of fal, the generative media platform powering the next wave of image, video, and audio applications. In less than two years, fal has scaled from $2M to over $100M in ARR, serving over 2 million developers and more than 300 enterprises, including Adobe, Canva, and Shopify. In this conversation, Gorkem shares the inside story of fal's pivot into explosive growth, the technical and cultural philosophies driving its success, and his predictions for the future of AI-generated media. In today's episode, we discuss: How fal pivoted from data infrastructure to generative inference fal’s explosive year and how they scaled Why "generative media" is a greenfield new market fal's unique hiring philosophy and lean <50-person team Building a brand that resonates with developers What the world looks like in 2027 when AI-generated video becomes mainstream And much more… Where to find Gorkem: LinkedIn X / Twitter Where to find Todd: LinkedIn X / Twitter Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: Adobe: https://www.adobe.com/ Amazon: https://www.amazon.com/ Anthropic: https://www.anthropic.com/ Base10: https://base10.vc/ Black Forest Labs: https://blackforestlabs.ai/ Burkay Gur: https://www.linkedin.com/in/burkaygur/ Canva: https://www.canva.com/ Clay: https://www.clay.com/ Coinbase: https://www.coinbase.com/ Cursor: https://www.cursor.com/ DALL-E: https://openai.com/dall-e-2 Databricks: https://www.databricks.com/ Dylan Patel: https://www.linkedin.com/in/dylanpatelsa/ fal: https://fal.ai/ Google DeepMind: https://deepmind.google/ LLaMA: https://ai.meta.com/llama/ OpenAI: https://openai.com/ Oracle: https://www.oracle.com/ Perplexity: https://www.perplexity.ai/ Shopify: https://www.shopify.com/ Snowflake: https://www.snowflake.com/ Sora: https://openai.com/sora Stable Diffusion XL (SDXL): https://stability.ai/stable-diffusion Stability AI: https://stability.ai/ Together AI: https://www.together.ai/ All images and videos generated using models run on fal.ai Timestamps: (01:43) The generative media industry (02:29) From $2M to $100M ARR: fal's explosive year (04:06) How Gorkem met co-founder Burkay Gur (05:38) The hardest decision that saved the company (09:52) Spotting the opportunity in generative media (13:28) Turning Todd into George Clooney (15:29) The early adopters of the first fal product (17:54) The transition from toy to tool (19:27) Why 2025 is the year of AI-generated video (21:44) Staying nimble as a 45-person company (24:42) Predicting AI-generated film in 2027 (27:24) Why generative media is a greenfield market (30:33) fal’s greatest optimization wins (34:42) Why fal has 500 Slack channels (36:02) Competing in a fast-moving, fragmented market (42:06) How to build a world-class team (47:24) Learning sales as a technical founder (50:55) How fal built a brand without a marketer (53:21) The story behind "GPU Rich / GPU Poor" (54:22) Inside fal’s rule-breaking playbook (56:09) The hardest part of scaling fal Wed, 22 Oct 2025 14:29:00 -0000 full First Round Gorkem Yurtseven is the co-founder and CTO of fal, the generative media platform powering the next wave of image, video, and audio applications. In less than two years, fal has scaled from $2M to over $100M in ARR, serving over 2 million developers and more than 300 enterprises, including Adobe, Canva, and Shopify. In this conversation, Gorkem shares the inside story of fal's pivot into explosive growth, the technical and cultural philosophies driving its success, and his predictions for the future of AI-generated media. In today's episode, we discuss: How fal pivoted from data infrastructure to generative inference fal’s explosive year and how they scaled Why "generative media" is a greenfield new market fal's unique hiring philosophy and lean <50-person team Building a brand that resonates with developers What the world looks like in 2027 when AI-generated video becomes mainstream And much more… Where to find Gorkem: LinkedIn X / Twitter Where to find Todd: LinkedIn X / Twitter Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: Adobe: https://www.adobe.com/ Amazon: https://www.amazon.com/ Anthropic: https://www.anthropic.com/ Base10: https://base10.vc/ Black Forest Labs: https://blackforestlabs.ai/ Burkay Gur: https://www.linkedin.com/in/burkaygur/ Canva: https://www.canva.com/ Clay: https://www.clay.com/ Coinbase: https://www.coinbase.com/ Cursor: https://www.cursor.com/ DALL-E: https://openai.com/dall-e-2 Databricks: https://www.databricks.com/ Dylan Patel: https://www.linkedin.com/in/dylanpatelsa/ fal: https://fal.ai/ Google DeepMind: https://deepmind.google/ LLaMA: https://ai.meta.com/llama/ OpenAI: https://openai.com/ Oracle: https://www.oracle.com/ Perplexity: https://www.perplexity.ai/ Shopify: https://www.shopify.com/ Snowflake: https://www.snowflake.com/ Sora: https://openai.com/sora Stable Diffusion XL (SDXL): https://stability.ai/stable-diffusion Stability AI: https://stability.ai/ Together AI: https://www.together.ai/ All images and videos generated using models run on fal.ai Timestamps: (01:43) The generative media industry (02:29) From $2M to $100M ARR: fal's explosive year (04:06) How Gorkem met co-founder Burkay Gur (05:38) The hardest decision that saved the company (09:52) Spotting the opportunity in generative media (13:28) Turning Todd into George Clooney (15:29) The early adopters of the first fal product (17:54) The transition from toy to tool (19:27) Why 2025 is the year of AI-generated video (21:44) Staying nimble as a 45-person company (24:42) Predicting AI-generated film in 2027 (27:24) Why generative media is a greenfield market (30:33) fal’s greatest optimization wins (34:42) Why fal has 500 Slack channels (36:02) Competing in a fast-moving, fragmented market (42:06) How to build a world-class team (47:24) Learning sales as a technical founder (50:55) How fal built a brand without a marketer (53:21) The story behind "GPU Rich / GPU Poor" (54:22) Inside fal’s rule-breaking playbook (56:09) The hardest part of scaling fal Gorkem Yurtseven is the co-founder and CTO of fal, the generative media platform powering the next wave of image, video, and audio applications. In less than two years, fal has scaled from $2M to over $100M in ARR, serving over 2 million developers and more than 300 enterprises, including Adobe, Canva, and Shopify. In this conversation, Gorkem shares the inside story of fal's pivot into explosive growth, the technical and cultural philosophies driving its success, and his predictions for the future of AI-generated media.

In today's episode, we discuss:

  • How fal pivoted from data infrastructure to generative inference
  • fal’s explosive year and how they scaled
  • Why "generative media" is a greenfield new market
  • fal's unique hiring philosophy and lean <50-person team
  • Building a brand that resonates with developers
  • What the world looks like in 2027 when AI-generated video becomes mainstream
  • And much more…


Where to find Gorkem:


Where to find Todd:


Where to find First Round Capital:


References:

  • Adobe: https://www.adobe.com/
  • Amazon: https://www.amazon.com/
  • Anthropic: https://www.anthropic.com/
  • Base10: https://base10.vc/
  • Black Forest Labs: https://blackforestlabs.ai/
  • Burkay Gur: https://www.linkedin.com/in/burkaygur/
  • Canva: https://www.canva.com/
  • Clay: https://www.clay.com/
  • Coinbase: https://www.coinbase.com/
  • Cursor: https://www.cursor.com/
  • DALL-E: https://openai.com/dall-e-2
  • Databricks: https://www.databricks.com/
  • Dylan Patel: https://www.linkedin.com/in/dylanpatelsa/
  • fal: https://fal.ai/
  • Google DeepMind: https://deepmind.google/
  • LLaMA: https://ai.meta.com/llama/
  • OpenAI: https://openai.com/
  • Oracle: https://www.oracle.com/
  • Perplexity: https://www.perplexity.ai/
  • Shopify: https://www.shopify.com/
  • Snowflake: https://www.snowflake.com/
  • Sora: https://openai.com/sora
  • Stable Diffusion XL (SDXL): https://stability.ai/stable-diffusion
  • Stability AI: https://stability.ai/
  • Together AI: https://www.together.ai/

All images and videos generated using models run on fal.ai


Timestamps:

(01:43) The generative media industry

(02:29) From $2M to $100M ARR: fal's explosive year

(04:06) How Gorkem met co-founder Burkay Gur

(05:38) The hardest decision that saved the company

(09:52) Spotting the opportunity in generative media

(13:28) Turning Todd into George Clooney

(15:29) The early adopters of the first fal product

(17:54) The transition from toy to tool

(19:27) Why 2025 is the year of AI-generated video

(21:44) Staying nimble as a 45-person company

(24:42) Predicting AI-generated film in 2027

(27:24) Why generative media is a greenfield market

(30:33) fal’s greatest optimization wins

(34:42) Why fal has 500 Slack channels

(36:02) Competing in a fast-moving, fragmented market

(42:06) How to build a world-class team

(47:24) Learning sales as a technical founder

(50:55) How fal built a brand without a marketer

(53:21) The story behind "GPU Rich / GPU Poor"

(54:22) Inside fal’s rule-breaking playbook

(56:09) The hardest part of scaling fal

]]> 3558 From dorm room to life-saving AI | Prepared’s story | Michael Chime (Co-founder & CEO of Prepared) Michael is the co-founder and CEO of Prepared, the AI assistant for 911 calls that helps dispatchers capture information faster, translate emergency calls in real time, and deliver lifesaving context to first responders. Founded out of Yale in 2019, Prepared grew from a school safety app into a critical platform for emergency communications, disrupting a notoriously tough market. This mission-driven journey just reached a major milestone: Prepared was acquired by Axon, the global public safety technology company. In this conversation, Michael joins Meka to share the inside story of building in a tough market, the counterintuitive strategies used to crack government procurement, and why their mission is a competitive moat. In today’s episode, we discuss: Why school shootings were the catalyst for building safety software Navigating the most challenging customer base: government and public safety agencies Why Prepared gave away its first product for free — for years Lessons from evolving a wedge product into an AI-driven suite How Michael balanced conviction with customer feedback Building long-term investor relationships Staying true to the mission through headwinds and tailwinds And much more… Where to find Michael: LinkedIn: https://www.linkedin.com/in/michaelchime/ Where to find Meka: LinkedIn: https://www.linkedin.com/in/mekaasonye/ Twitter/X: https://x.com/bigmekastyle Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: Axon: https://www.axon.com/ Dylan Gleicher: https://www.linkedin.com/in/dylan-gleicher/ March for Our Lives: https://marchforourlives.org/ Neal Soni: https://www.linkedin.com/in/neal-soni/ OpenAI: https://openai.com/ Peter Thiel Fellowship: https://thielfellowship.org/ Prepared: https://www.prepared911.com/ Sam Altman: https://x.com/sama Slack: https://slack.com/ Uber Eats: https://www.ubereats.com/ Yale University: https://www.yale.edu/ Timestamps: (3:03) Staying mission-oriented under pressure (3:54) Negotiating an acquisition from a hospital bed (06:25) How Sandy Hook shaped the Prepared story (09:15) From school safety app to 911 platform (10:02) Why are 911 systems so outdated? (13:02) Prepared’s first product iteration (16:04) Why attempt to tackle the govtech market? (18:36) Mission as fuel: staying resilient through endless rejections (20:03) Should young people drop out of college? (23:10) How Michael nurtured a learner’s mindset (25:23) Forging unwavering founder conviction (31:41) Landing Prepared’s first user (32:39) “I want to be terrible at sales” (34:35) Expanding to a premium product line (36:55) Leveraging AI to expand the product surface area (41:49) How much should you listen to customers? (45:35) Building in headwinds vs. tailwinds (47:18) Navigating partnerships and competition (54:52) Michael’s unconventional approach to fundraising (1:02:54) Has Prepared found product-market fit? (1:04:00) Reflecting on the founder journey Wed, 01 Oct 2025 16:24:00 -0000 full First Round Michael is the co-founder and CEO of Prepared, the AI assistant for 911 calls that helps dispatchers capture information faster, translate emergency calls in real time, and deliver lifesaving context to first responders. Founded out of Yale in 2019, Prepared grew from a school safety app into a critical platform for emergency communications, disrupting a notoriously tough market. This mission-driven journey just reached a major milestone: Prepared was acquired by Axon, the global public safety technology company. In this conversation, Michael joins Meka to share the inside story of building in a tough market, the counterintuitive strategies used to crack government procurement, and why their mission is a competitive moat. In today’s episode, we discuss: Why school shootings were the catalyst for building safety software Navigating the most challenging customer base: government and public safety agencies Why Prepared gave away its first product for free — for years Lessons from evolving a wedge product into an AI-driven suite How Michael balanced conviction with customer feedback Building long-term investor relationships Staying true to the mission through headwinds and tailwinds And much more… Where to find Michael: LinkedIn: https://www.linkedin.com/in/michaelchime/ Where to find Meka: LinkedIn: https://www.linkedin.com/in/mekaasonye/ Twitter/X: https://x.com/bigmekastyle Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast References: Axon: https://www.axon.com/ Dylan Gleicher: https://www.linkedin.com/in/dylan-gleicher/ March for Our Lives: https://marchforourlives.org/ Neal Soni: https://www.linkedin.com/in/neal-soni/ OpenAI: https://openai.com/ Peter Thiel Fellowship: https://thielfellowship.org/ Prepared: https://www.prepared911.com/ Sam Altman: https://x.com/sama Slack: https://slack.com/ Uber Eats: https://www.ubereats.com/ Yale University: https://www.yale.edu/ Timestamps: (3:03) Staying mission-oriented under pressure (3:54) Negotiating an acquisition from a hospital bed (06:25) How Sandy Hook shaped the Prepared story (09:15) From school safety app to 911 platform (10:02) Why are 911 systems so outdated? (13:02) Prepared’s first product iteration (16:04) Why attempt to tackle the govtech market? (18:36) Mission as fuel: staying resilient through endless rejections (20:03) Should young people drop out of college? (23:10) How Michael nurtured a learner’s mindset (25:23) Forging unwavering founder conviction (31:41) Landing Prepared’s first user (32:39) “I want to be terrible at sales” (34:35) Expanding to a premium product line (36:55) Leveraging AI to expand the product surface area (41:49) How much should you listen to customers? (45:35) Building in headwinds vs. tailwinds (47:18) Navigating partnerships and competition (54:52) Michael’s unconventional approach to fundraising (1:02:54) Has Prepared found product-market fit? (1:04:00) Reflecting on the founder journey Michael is the co-founder and CEO of Prepared, the AI assistant for 911 calls that helps dispatchers capture information faster, translate emergency calls in real time, and deliver lifesaving context to first responders. Founded out of Yale in 2019, Prepared grew from a school safety app into a critical platform for emergency communications, disrupting a notoriously tough market. This mission-driven journey just reached a major milestone: Prepared was acquired by Axon, the global public safety technology company. In this conversation, Michael joins Meka to share the inside story of building in a tough market, the counterintuitive strategies used to crack government procurement, and why their mission is a competitive moat. In today’s episode, we discuss:

  • Why school shootings were the catalyst for building safety software
  • Navigating the most challenging customer base: government and public safety agencies
  • Why Prepared gave away its first product for free — for years
  • Lessons from evolving a wedge product into an AI-driven suite
  • How Michael balanced conviction with customer feedback
  • Building long-term investor relationships
  • Staying true to the mission through headwinds and tailwinds
  • And much more…


Where to find Michael:

  • LinkedIn: https://www.linkedin.com/in/michaelchime/


Where to find Meka:

  • LinkedIn: https://www.linkedin.com/in/mekaasonye/
  • Twitter/X: https://x.com/bigmekastyle


Where to find First Round Capital:

  • Website: https://firstround.com/
  • First Round Review: https://review.firstround.com/
  • Twitter/X: https://twitter.com/firstround
  • YouTube: https://www.youtube.com/@FirstRoundCapital
  • This podcast on all platforms: https://review.firstround.com/podcast


References:

  • Axon: https://www.axon.com/
  • Dylan Gleicher: https://www.linkedin.com/in/dylan-gleicher/
  • March for Our Lives: https://marchforourlives.org/
  • Neal Soni: https://www.linkedin.com/in/neal-soni/
  • OpenAI: https://openai.com/
  • Peter Thiel Fellowship: https://thielfellowship.org/
  • Prepared: https://www.prepared911.com/
  • Sam Altman: https://x.com/sama
  • Slack: https://slack.com/
  • Uber Eats: https://www.ubereats.com/
  • Yale University: https://www.yale.edu/

Timestamps:

(3:03) Staying mission-oriented under pressure (3:54) Negotiating an acquisition from a hospital bed (06:25) How Sandy Hook shaped the Prepared story (09:15) From school safety app to 911 platform (10:02) Why are 911 systems so outdated? (13:02) Prepared’s first product iteration (16:04) Why attempt to tackle the govtech market? (18:36) Mission as fuel: staying resilient through endless rejections (20:03) Should young people drop out of college? (23:10) How Michael nurtured a learner’s mindset (25:23) Forging unwavering founder conviction (31:41) Landing Prepared’s first user (32:39) “I want to be terrible at sales” (34:35) Expanding to a premium product line (36:55) Leveraging AI to expand the product surface area (41:49) How much should you listen to customers? (45:35) Building in headwinds vs. tailwinds (47:18) Navigating partnerships and competition (54:52) Michael’s unconventional approach to fundraising (1:02:54) Has Prepared found product-market fit? (1:04:00) Reflecting on the founder journey

]]> 4147 Saying yes to everything: How customer obsession built Samsara | Kiren Sekar (CPO) Kiren Sekar is the CPO of Samsara, a company that brings real-time visibility, analytics, and AI to physical operations. Before Samsara, Kiren was an early leader at Meraki, which was acquired by Cisco for $1.2B. In this episode, he walks us through Samsara’s origin story: from hardware hacking in a basement to scaling a cross-industry IoT platform. He shares how early customer feedback loops led to the company’s first product, why starting with the mid-market was a deliberate choice, and how Samsara kept a startup mindset even as it scaled. In this episode, we discuss: Lessons from Meraki’s acquisition by Cisco How Kiren hires for intrinsic motivation Why Samsara was built for operations industries The early hardware prototype and the Cowgirl Creamery insight Building broad vs. niche from day one The shift from founder-selling to a scalable sales motion Organizing product teams around revenue vs. experience How Samsara uses LLMs and AI today What Kiren learned from longtime co-founder Sanjit Biswas Where to find Kiren: LinkedIn: https://www.linkedin.com/in/kirensekar/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson References: Cisco: https://www.cisco.com/ Clay: https://www.clay.com/ Cowgirl Creamery: https://cowgirlcreamery.com/ IBM: https://www.ibm.com/ Meraki: https://meraki.cisco.com/ Microsoft: https://www.microsoft.com/ Salesforce: https://www.salesforce.com/ Samsara: https://www.samsara.com/ Sanjit Biswas: https://www.linkedin.com/in/sanjitbiswas/ Uber: https://www.uber.com/ Timestamps: (01:27) Meraki’s growth and acquisition by Cisco (03:25) The "evaporating" exit strategy from Meraki (04:42) Identifying the IoT market gaps (07:38) The early keys to success at Samsara (09:39) What does quality mean to Kiren? (10:54) Building a customer-centric roadmap (17:34) Early customer research and the failed fridge monitoring idea (20:57) How a cheese producer helped create Samsara’s first prototype (28:06) Balancing depth and breadth in customer profiles (33:45) Developing customer trust to build feedback loops (40:27) How “ease of use” became a growth secret (44:23) Pricing strategies and market positioning (51:51) How Meraki influenced Samsara’s GTM strategy (57:19) Helping customers navigate change management (1:00:48) How Samsara’s team evolved during rapid growth (1:04:03) What AI means for an IoT giant Thu, 11 Sep 2025 11:00:00 -0000 full First Round Kiren Sekar is the CPO of Samsara, a company that brings real-time visibility, analytics, and AI to physical operations. Before Samsara, Kiren was an early leader at Meraki, which was acquired by Cisco for $1.2B. In this episode, he walks us through Samsara’s origin story: from hardware hacking in a basement to scaling a cross-industry IoT platform. He shares how early customer feedback loops led to the company’s first product, why starting with the mid-market was a deliberate choice, and how Samsara kept a startup mindset even as it scaled. In this episode, we discuss: Lessons from Meraki’s acquisition by Cisco How Kiren hires for intrinsic motivation Why Samsara was built for operations industries The early hardware prototype and the Cowgirl Creamery insight Building broad vs. niche from day one The shift from founder-selling to a scalable sales motion Organizing product teams around revenue vs. experience How Samsara uses LLMs and AI today What Kiren learned from longtime co-founder Sanjit Biswas Where to find Kiren: LinkedIn: https://www.linkedin.com/in/kirensekar/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson References: Cisco: https://www.cisco.com/ Clay: https://www.clay.com/ Cowgirl Creamery: https://cowgirlcreamery.com/ IBM: https://www.ibm.com/ Meraki: https://meraki.cisco.com/ Microsoft: https://www.microsoft.com/ Salesforce: https://www.salesforce.com/ Samsara: https://www.samsara.com/ Sanjit Biswas: https://www.linkedin.com/in/sanjitbiswas/ Uber: https://www.uber.com/ Timestamps: (01:27) Meraki’s growth and acquisition by Cisco (03:25) The "evaporating" exit strategy from Meraki (04:42) Identifying the IoT market gaps (07:38) The early keys to success at Samsara (09:39) What does quality mean to Kiren? (10:54) Building a customer-centric roadmap (17:34) Early customer research and the failed fridge monitoring idea (20:57) How a cheese producer helped create Samsara’s first prototype (28:06) Balancing depth and breadth in customer profiles (33:45) Developing customer trust to build feedback loops (40:27) How “ease of use” became a growth secret (44:23) Pricing strategies and market positioning (51:51) How Meraki influenced Samsara’s GTM strategy (57:19) Helping customers navigate change management (1:00:48) How Samsara’s team evolved during rapid growth (1:04:03) What AI means for an IoT giant Kiren Sekar is the CPO of Samsara, a company that brings real-time visibility, analytics, and AI to physical operations. Before Samsara, Kiren was an early leader at Meraki, which was acquired by Cisco for $1.2B.

In this episode, he walks us through Samsara’s origin story: from hardware hacking in a basement to scaling a cross-industry IoT platform. He shares how early customer feedback loops led to the company’s first product, why starting with the mid-market was a deliberate choice, and how Samsara kept a startup mindset even as it scaled.

In this episode, we discuss:

  • Lessons from Meraki’s acquisition by Cisco
  • How Kiren hires for intrinsic motivation
  • Why Samsara was built for operations industries
  • The early hardware prototype and the Cowgirl Creamery insight
  • Building broad vs. niche from day one
  • The shift from founder-selling to a scalable sales motion
  • Organizing product teams around revenue vs. experience
  • How Samsara uses LLMs and AI today
  • What Kiren learned from longtime co-founder Sanjit Biswas


Where to find Kiren:


Where to find Brett:


References:


Timestamps:

(01:27) Meraki’s growth and acquisition by Cisco

(03:25) The "evaporating" exit strategy from Meraki

(04:42) Identifying the IoT market gaps

(07:38) The early keys to success at Samsara

(09:39) What does quality mean to Kiren?

(10:54) Building a customer-centric roadmap

(17:34) Early customer research and the failed fridge monitoring idea

(20:57) How a cheese producer helped create Samsara’s first prototype

(28:06) Balancing depth and breadth in customer profiles

(33:45) Developing customer trust to build feedback loops

(40:27) How “ease of use” became a growth secret

(44:23) Pricing strategies and market positioning

(51:51) How Meraki influenced Samsara’s GTM strategy

(57:19) Helping customers navigate change management

(1:00:48) How Samsara’s team evolved during rapid growth

(1:04:03) What AI means for an IoT giant

]]> 4137 Starting an education giant in a “bad market” | ClassDojo’s story | Sam Chaudhary (Co-founder and CEO) Sam Chaudhary is the co-founder and CEO of ClassDojo, a multi-product education platform used in 95% of U.S. schools and over 180 countries globally to connect teachers, students, and families. In this episode, Sam shares the full arc of building ClassDojo, from early skepticism about education and a failed group-making tool, to creating a communication platform loved by millions. In this episode, we discuss: Why ClassDojo was built for consumers (teachers, students and parents) instead of schools How ClassDojo grew entirely by word-of-mouth Sam’s unusual approach to building multiple new businesses The founder mindset required to build an industry leader Why relentless resourcefulness is an underrated skill And much more… References: Accel: https://www.accel.com/ Airbnb: https://www.airbnb.com/ Bill Gates: https://www.linkedin.com/in/williamhgates/ Brendan Kereiakes: https://www.linkedin.com/in/product/ ClassDojo: https://www.classdojo.com/ Dominick Bellizzi: https://www.linkedin.com/in/dominickbellizzi/ Geoff Ralston: https://www.linkedin.com/in/geoffralston/ Gonzalo Aguilar Málaga: https://www.linkedin.com/in/gonzalodecheck/ Hamilton Helmer: https://www.linkedin.com/in/hamilton-helmer-42983/ Imagine K12: https://www.imaginek12.com// Khan Academy: https://www.khanacademy.org/ Liam Don: https://www.linkedin.com/in/liamdon/ McKinsey: https://www.mckinsey.com/ Paul Graham: https://x.com/paulg Plaid: https://plaid.com/ Reid Hoffman: https://www.linkedin.com/in/reidhoffman/ Roblox: https://www.roblox.com/ Sal Khan: https://www.linkedin.com/in/khanacademy/ Superhuman: https://superhuman.com/ Tim Brady: https://www.linkedin.com/in/tim-brady-7a632510/ Y Combinator: https://www.ycombinator.com/ Where to find Sam: LinkedIn: https://www.linkedin.com/in/samchaudhary/ Twitter/X: https://x.com/samchaudhary Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Timestamps: (01:36) Why education is a “bad market” (02:52) Why enterprise education is broken (03:35) Building for families, not schools (06:53) Early challenges and insights (09:45) Sam’s unusual background (11:42) Meeting co-founder Liam at a hackathon (13:22) Getting into Imagine K12 with a group-making tool (19:47) The conversation with Reid Hoffman that changed everything (21:52) Building a network to reach more families (23:30) Scaling by building a community (33:18) Designing for delight and word-of-mouth growth (40:09) Launching the first monetization feature after 7 years (41:35) How to pick markets and when to go broad (46:04) The explosive expansion into the tutoring industry (55:11) Creating safe online spaces for kids (58:01) Harnessing AI in education (59:52) Lessons from ClassDojo’s playbook Wed, 03 Sep 2025 16:37:00 -0000 full First Round Sam Chaudhary is the co-founder and CEO of ClassDojo, a multi-product education platform used in 95% of U.S. schools and over 180 countries globally to connect teachers, students, and families. In this episode, Sam shares the full arc of building ClassDojo, from early skepticism about education and a failed group-making tool, to creating a communication platform loved by millions. In this episode, we discuss: Why ClassDojo was built for consumers (teachers, students and parents) instead of schools How ClassDojo grew entirely by word-of-mouth Sam’s unusual approach to building multiple new businesses The founder mindset required to build an industry leader Why relentless resourcefulness is an underrated skill And much more… References: Accel: https://www.accel.com/ Airbnb: https://www.airbnb.com/ Bill Gates: https://www.linkedin.com/in/williamhgates/ Brendan Kereiakes: https://www.linkedin.com/in/product/ ClassDojo: https://www.classdojo.com/ Dominick Bellizzi: https://www.linkedin.com/in/dominickbellizzi/ Geoff Ralston: https://www.linkedin.com/in/geoffralston/ Gonzalo Aguilar Málaga: https://www.linkedin.com/in/gonzalodecheck/ Hamilton Helmer: https://www.linkedin.com/in/hamilton-helmer-42983/ Imagine K12: https://www.imaginek12.com// Khan Academy: https://www.khanacademy.org/ Liam Don: https://www.linkedin.com/in/liamdon/ McKinsey: https://www.mckinsey.com/ Paul Graham: https://x.com/paulg Plaid: https://plaid.com/ Reid Hoffman: https://www.linkedin.com/in/reidhoffman/ Roblox: https://www.roblox.com/ Sal Khan: https://www.linkedin.com/in/khanacademy/ Superhuman: https://superhuman.com/ Tim Brady: https://www.linkedin.com/in/tim-brady-7a632510/ Y Combinator: https://www.ycombinator.com/ Where to find Sam: LinkedIn: https://www.linkedin.com/in/samchaudhary/ Twitter/X: https://x.com/samchaudhary Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Timestamps: (01:36) Why education is a “bad market” (02:52) Why enterprise education is broken (03:35) Building for families, not schools (06:53) Early challenges and insights (09:45) Sam’s unusual background (11:42) Meeting co-founder Liam at a hackathon (13:22) Getting into Imagine K12 with a group-making tool (19:47) The conversation with Reid Hoffman that changed everything (21:52) Building a network to reach more families (23:30) Scaling by building a community (33:18) Designing for delight and word-of-mouth growth (40:09) Launching the first monetization feature after 7 years (41:35) How to pick markets and when to go broad (46:04) The explosive expansion into the tutoring industry (55:11) Creating safe online spaces for kids (58:01) Harnessing AI in education (59:52) Lessons from ClassDojo’s playbook Sam Chaudhary is the co-founder and CEO of ClassDojo, a multi-product education platform used in 95% of U.S. schools and over 180 countries globally to connect teachers, students, and families. In this episode, Sam shares the full arc of building ClassDojo, from early skepticism about education and a failed group-making tool, to creating a communication platform loved by millions.

In this episode, we discuss:

  • Why ClassDojo was built for consumers (teachers, students and parents) instead of schools
  • How ClassDojo grew entirely by word-of-mouth
  • Sam’s unusual approach to building multiple new businesses
  • The founder mindset required to build an industry leader
  • Why relentless resourcefulness is an underrated skill
  • And much more…


References:


Where to find Sam:


Where to find Brett:


Timestamps:

(01:36) Why education is a “bad market”

(02:52) Why enterprise education is broken

(03:35) Building for families, not schools

(06:53) Early challenges and insights

(09:45) Sam’s unusual background

(11:42) Meeting co-founder Liam at a hackathon

(13:22) Getting into Imagine K12 with a group-making tool

(19:47) The conversation with Reid Hoffman that changed everything

(21:52) Building a network to reach more families

(23:30) Scaling by building a community

(33:18) Designing for delight and word-of-mouth growth

(40:09) Launching the first monetization feature after 7 years

(41:35) How to pick markets and when to go broad

(46:04) The explosive expansion into the tutoring industry

(55:11) Creating safe online spaces for kids

(58:01) Harnessing AI in education

(59:52) Lessons from ClassDojo’s playbook

]]> 4349 From Chrome extension to $5B platform | Postman’s journey | Abhinav Asthana (Co-founder & CEO) Abhinav Asthana is the co-founder and CEO of Postman, the world's leading API collaboration platform used by millions of developers and thousands of companies. What began as a personal itch, a simple Chrome extension Abhinav built to make his own API work easier, became a global phenomenon within weeks. In this episode, we discuss: Making the leap from India to Silicon Valley The moment Abhinav realized Postman could win His principles behind building for developers and non-developers alike The early monetization experiments that led to their SaaS model The value of progressive complexity in product design How community building became a powerful growth lever And much more… References: Abhijit Kane: https://www.linkedin.com/in/abhijitkane/ Adobe: https://www.adobe.com/ Ankit Sobti: https://www.linkedin.com/in/ankit-sobti/ Figma: https://www.figma.com/ Kong Inc.: https://konghq.com/ National University of Singapore: https://nus.edu.sg/ Postman: https://www.postman.com/ Ram Gupta: : https://www.linkedin.com/in/ram-gupta-39b9711/ Slack: https://slack.com/ Stripe: https://stripe.com/ Stewart Butterfield: https://www.linkedin.com/in/butterfield/ Yahoo: http://yahoo.com/ Where to find Abhinav: LinkedIn: https://www.linkedin.com/in/abhinavasthana/ Twitter/X: https://x.com/a85 Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: (01:18) Why early computer access changed everything (03:39) The first taste of the entrepreneurial bug (09:58) Building BITS360 in college (11:14) Curating entrepreneurial taste (15:49) The ventures that didn’t make it (20:53) The problems that preceded Postman (29:56) How Postman’s team was formed (34:01) Why clear roles prevent chaos (34:50) Scrappy startup life in the early days (36:26) Postman’s path to monetization (39:59) Building a truly collaborative platform (43:00) Navigating market and customer needs (46:02) Cracking the go-to-market code (49:39) Bridging the developer-enterprise divide (54:43) The open-source dilemma Thu, 28 Aug 2025 11:00:00 -0000 full First Round Abhinav Asthana is the co-founder and CEO of Postman, the world's leading API collaboration platform used by millions of developers and thousands of companies. What began as a personal itch, a simple Chrome extension Abhinav built to make his own API work easier, became a global phenomenon within weeks. In this episode, we discuss: Making the leap from India to Silicon Valley The moment Abhinav realized Postman could win His principles behind building for developers and non-developers alike The early monetization experiments that led to their SaaS model The value of progressive complexity in product design How community building became a powerful growth lever And much more… References: Abhijit Kane: https://www.linkedin.com/in/abhijitkane/ Adobe: https://www.adobe.com/ Ankit Sobti: https://www.linkedin.com/in/ankit-sobti/ Figma: https://www.figma.com/ Kong Inc.: https://konghq.com/ National University of Singapore: https://nus.edu.sg/ Postman: https://www.postman.com/ Ram Gupta: : https://www.linkedin.com/in/ram-gupta-39b9711/ Slack: https://slack.com/ Stripe: https://stripe.com/ Stewart Butterfield: https://www.linkedin.com/in/butterfield/ Yahoo: http://yahoo.com/ Where to find Abhinav: LinkedIn: https://www.linkedin.com/in/abhinavasthana/ Twitter/X: https://x.com/a85 Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: (01:18) Why early computer access changed everything (03:39) The first taste of the entrepreneurial bug (09:58) Building BITS360 in college (11:14) Curating entrepreneurial taste (15:49) The ventures that didn’t make it (20:53) The problems that preceded Postman (29:56) How Postman’s team was formed (34:01) Why clear roles prevent chaos (34:50) Scrappy startup life in the early days (36:26) Postman’s path to monetization (39:59) Building a truly collaborative platform (43:00) Navigating market and customer needs (46:02) Cracking the go-to-market code (49:39) Bridging the developer-enterprise divide (54:43) The open-source dilemma Abhinav Asthana is the co-founder and CEO of Postman, the world's leading API collaboration platform used by millions of developers and thousands of companies. What began as a personal itch, a simple Chrome extension Abhinav built to make his own API work easier, became a global phenomenon within weeks.


In this episode, we discuss:

  • Making the leap from India to Silicon Valley
  • The moment Abhinav realized Postman could win
  • His principles behind building for developers and non-developers alike
  • The early monetization experiments that led to their SaaS model
  • The value of progressive complexity in product design
  • How community building became a powerful growth lever
  • And much more…


References:

  • Abhijit Kane: https://www.linkedin.com/in/abhijitkane/
  • Adobe: https://www.adobe.com/
  • Ankit Sobti: https://www.linkedin.com/in/ankit-sobti/
  • Figma: https://www.figma.com/
  • Kong Inc.: https://konghq.com/
  • National University of Singapore: https://nus.edu.sg/
  • Postman: https://www.postman.com/
  • Ram Gupta: : https://www.linkedin.com/in/ram-gupta-39b9711/
  • Slack: https://slack.com/
  • Stripe: https://stripe.com/
  • Stewart Butterfield: https://www.linkedin.com/in/butterfield/
  • Yahoo: http://yahoo.com/


Where to find Abhinav:

  • LinkedIn: https://www.linkedin.com/in/abhinavasthana/
  • Twitter/X: https://x.com/a85


Where to find Brett:

  • LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
  • Twitter/X: https://twitter.com/brettberson


Where to find First Round Capital:

  • Website: https://firstround.com/
  • First Round Review: https://review.firstround.com/
  • Twitter/X: https://twitter.com/firstround
  • YouTube: https://www.youtube.com/@FirstRoundCapital
  • This podcast on all platforms: https://review.firstround.com/podcast


Timestamps:

(01:18) Why early computer access changed everything

(03:39) The first taste of the entrepreneurial bug

(09:58) Building BITS360 in college

(11:14) Curating entrepreneurial taste

(15:49) The ventures that didn’t make it

(20:53) The problems that preceded Postman

(29:56) How Postman’s team was formed

(34:01) Why clear roles prevent chaos

(34:50) Scrappy startup life in the early days

(36:26) Postman’s path to monetization

(39:59) Building a truly collaborative platform

(43:00) Navigating market and customer needs

(46:02) Cracking the go-to-market code

(49:39) Bridging the developer-enterprise divide

(54:43) The open-source dilemma

]]> 3980 How Canva leveraged unconventional growth levers to grow to $42B | Cameron Adams (Co-founder & CPO) Cameron Adams is the co-founder and Chief Product Officer at Canva, the design platform valued at $42B as of July 2025, used by over 230 million people every month. Before starting Canva, Cameron was a designer and engineer at Google and co-founded Fluent, an email startup. In this episode, Cameron walks through Canva’s earliest days — from the remarkably fast courtship with co-founders Melanie Perkins and Cliff Obrecht, to the counterintuitive product decisions that helped Canva instantly resonate with users who thought they would never design anything. In this episode, we cover: How Canva turned social media managers into early evangelists Balancing a huge vision with scrappy execution Hard lessons from their near-silent launch day The two growth levers that changed everything And much more… References: Adobe: https://www.adobe.com/home Atlassian: https://www.atlassian.com/ Campaign Monitor: https://www.campaignmonitor.com/ Canva: https://www.canva.com/ Cliff Obrecht: https://www.linkedin.com/in/cliff-obrecht-79ba9920/ Dave Greiner: https://www.linkedin.com/in/davegreiner/ Lars Rasmussen: https://www.linkedin.com/in/larserasmussen/ Melanie Perkins: https://www.linkedin.com/in/melanieperkins/ Mike Cannon-Brookes: https://www.linkedin.com/in/mcannonbrookes/ New York Stock Exchange: https://www.nyse.com/ Pinterest: https://pinterest.com/ Scott Farquhar: https://www.linkedin.com/in/scottfarquhar/ Where to find Cameron: LinkedIn: https://www.linkedin.com/in/themaninblue/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ X/Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: (01:24) The birth of Canva (04:32) Meeting Canva’s co-founders (11:22) Building the first iteration of Canva (15:26) The discovery that changed prototyping (20:48) Why onboarding was the unlock for retention (27:36) The anticlimactic launch day (32:43) How word-of-mouth spurred early retention (36:33) Targeting different user personas (41:02) Building a community on social media (43:38) Two impactful growth levers (47:14) Why Canva should have gone mobile sooner (48:12) What underpins Canva’s dominance today (53:37) Rebuilding for enterprise (58:38) Lessons from Canva’s tough times Wed, 20 Aug 2025 15:10:00 -0000 full First Round Cameron Adams is the co-founder and Chief Product Officer at Canva, the design platform valued at $42B as of July 2025, used by over 230 million people every month. Before starting Canva, Cameron was a designer and engineer at Google and co-founded Fluent, an email startup. In this episode, Cameron walks through Canva’s earliest days — from the remarkably fast courtship with co-founders Melanie Perkins and Cliff Obrecht, to the counterintuitive product decisions that helped Canva instantly resonate with users who thought they would never design anything. In this episode, we cover: How Canva turned social media managers into early evangelists Balancing a huge vision with scrappy execution Hard lessons from their near-silent launch day The two growth levers that changed everything And much more… References: Adobe: https://www.adobe.com/home Atlassian: https://www.atlassian.com/ Campaign Monitor: https://www.campaignmonitor.com/ Canva: https://www.canva.com/ Cliff Obrecht: https://www.linkedin.com/in/cliff-obrecht-79ba9920/ Dave Greiner: https://www.linkedin.com/in/davegreiner/ Lars Rasmussen: https://www.linkedin.com/in/larserasmussen/ Melanie Perkins: https://www.linkedin.com/in/melanieperkins/ Mike Cannon-Brookes: https://www.linkedin.com/in/mcannonbrookes/ New York Stock Exchange: https://www.nyse.com/ Pinterest: https://pinterest.com/ Scott Farquhar: https://www.linkedin.com/in/scottfarquhar/ Where to find Cameron: LinkedIn: https://www.linkedin.com/in/themaninblue/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ X/Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: (01:24) The birth of Canva (04:32) Meeting Canva’s co-founders (11:22) Building the first iteration of Canva (15:26) The discovery that changed prototyping (20:48) Why onboarding was the unlock for retention (27:36) The anticlimactic launch day (32:43) How word-of-mouth spurred early retention (36:33) Targeting different user personas (41:02) Building a community on social media (43:38) Two impactful growth levers (47:14) Why Canva should have gone mobile sooner (48:12) What underpins Canva’s dominance today (53:37) Rebuilding for enterprise (58:38) Lessons from Canva’s tough times Cameron Adams is the co-founder and Chief Product Officer at Canva, the design platform valued at $42B as of July 2025, used by over 230 million people every month.

Before starting Canva, Cameron was a designer and engineer at Google and co-founded Fluent, an email startup. In this episode, Cameron walks through Canva’s earliest days — from the remarkably fast courtship with co-founders Melanie Perkins and Cliff Obrecht, to the counterintuitive product decisions that helped Canva instantly resonate with users who thought they would never design anything.


In this episode, we cover:

  • How Canva turned social media managers into early evangelists
  • Balancing a huge vision with scrappy execution
  • Hard lessons from their near-silent launch day
  • The two growth levers that changed everything
  • And much more…

References:

Where to find Cameron:

Where to find Brett:

Where to find First Round Capital:

Timestamps:

(01:24) The birth of Canva

(04:32) Meeting Canva’s co-founders

(11:22) Building the first iteration of Canva

(15:26) The discovery that changed prototyping

(20:48) Why onboarding was the unlock for retention

(27:36) The anticlimactic launch day

(32:43) How word-of-mouth spurred early retention

(36:33) Targeting different user personas

(41:02) Building a community on social media

(43:38) Two impactful growth levers

(47:14) Why Canva should have gone mobile sooner

(48:12) What underpins Canva’s dominance today

(53:37) Rebuilding for enterprise

(58:38) Lessons from Canva’s tough times

]]> 3866 Twitter's former CEO on rebuilding the web for AI | Parag Agrawal (Co-founder and CEO of Parallel) Parag Agrawal is the co-founder and CEO of Parallel, a startup building search infrastructure for the web’s second user: AIs. Before launching Parallel, Parag spent over a decade at Twitter, where he served as CTO and later CEO during a period of intense transformation, as well as public scrutiny. In this episode, Parag shares what he learned from his time at Twitter, why the web must evolve to serve AI at massive scale, how Parallel is tackling “deep research” challenges by prioritizing accuracy over speed, and the design choices that make their APIs uniquely agent-friendly. We also discuss: Why Parallel designs for AI as the primary customer Lessons from 11 years at Twitter and applying them to a startup Potential business models to keep the web open for AI Hiring philosophy: balancing high potential and experienced talent The evolving role of engineers in an AI-assisted world Why “agents” are finally becoming useful in production And much more… References: Bloomberg launch coverage: https://www.bloomberg.com/news/articles/2025-08-14/twitter-ex-ceo-parag-agrawal-is-moving-past-his-elon-musk-drama Clay: https://www.clay.com/ Index Ventures: https://www.indexventures.com/ Josh Kopelman: https://www.linkedin.com/in/jkopelman/ KLA: https://www.kla.com/ OpenAI: https://openai.com/ Parallel: https://parallel.ai/ Patrick Collison: https://www.linkedin.com/in/patrickcollison/ Stripe: https://stripe.com/ Where to find Parag: LinkedIn: https://www.linkedin.com/in/paragagr/ X/Twitter: https://x.com/paraga Where to find Todd: LinkedIn: https://www.linkedin.com/in/toddj0/ X/Twitter: https://x.com/tjack Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ X/Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: (1:26) Founding Parallel with an AI-first mission (3:23) From Twitter CTO/CEO to startup founder (6:20) What the AI era spells for companies (7:58) The CEO to founder pipeline (11:18) Reflections on Twitter’s transformation (17:48) How Parallel was born (22:31) Early use cases for Parallel (31:42) How has Parallel’s ICP changed? (34:37) AI’s impact on competitor dynamics (36:06) When should founders launch? (37:43) Parag’s fundraising framework (40:14) Building a high-impact engineering team (44:49) Counterproductive uses of AI (47:35) How will the software engineer role evolve? (49:10) How are Parallel’s customers using AI? (53:27) Defining agents in 2025 (55:02) Parallel’s long-term vision (1:03:43) Parag’s growth as a founder Thu, 14 Aug 2025 14:15:00 -0000 full First Round Parag Agrawal is the co-founder and CEO of Parallel, a startup building search infrastructure for the web’s second user: AIs. Before launching Parallel, Parag spent over a decade at Twitter, where he served as CTO and later CEO during a period of intense transformation, as well as public scrutiny. In this episode, Parag shares what he learned from his time at Twitter, why the web must evolve to serve AI at massive scale, how Parallel is tackling “deep research” challenges by prioritizing accuracy over speed, and the design choices that make their APIs uniquely agent-friendly. We also discuss: Why Parallel designs for AI as the primary customer Lessons from 11 years at Twitter and applying them to a startup Potential business models to keep the web open for AI Hiring philosophy: balancing high potential and experienced talent The evolving role of engineers in an AI-assisted world Why “agents” are finally becoming useful in production And much more… References: Bloomberg launch coverage: https://www.bloomberg.com/news/articles/2025-08-14/twitter-ex-ceo-parag-agrawal-is-moving-past-his-elon-musk-drama Clay: https://www.clay.com/ Index Ventures: https://www.indexventures.com/ Josh Kopelman: https://www.linkedin.com/in/jkopelman/ KLA: https://www.kla.com/ OpenAI: https://openai.com/ Parallel: https://parallel.ai/ Patrick Collison: https://www.linkedin.com/in/patrickcollison/ Stripe: https://stripe.com/ Where to find Parag: LinkedIn: https://www.linkedin.com/in/paragagr/ X/Twitter: https://x.com/paraga Where to find Todd: LinkedIn: https://www.linkedin.com/in/toddj0/ X/Twitter: https://x.com/tjack Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ X/Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: (1:26) Founding Parallel with an AI-first mission (3:23) From Twitter CTO/CEO to startup founder (6:20) What the AI era spells for companies (7:58) The CEO to founder pipeline (11:18) Reflections on Twitter’s transformation (17:48) How Parallel was born (22:31) Early use cases for Parallel (31:42) How has Parallel’s ICP changed? (34:37) AI’s impact on competitor dynamics (36:06) When should founders launch? (37:43) Parag’s fundraising framework (40:14) Building a high-impact engineering team (44:49) Counterproductive uses of AI (47:35) How will the software engineer role evolve? (49:10) How are Parallel’s customers using AI? (53:27) Defining agents in 2025 (55:02) Parallel’s long-term vision (1:03:43) Parag’s growth as a founder Parag Agrawal is the co-founder and CEO of Parallel, a startup building search infrastructure for the web’s second user: AIs. Before launching Parallel, Parag spent over a decade at Twitter, where he served as CTO and later CEO during a period of intense transformation, as well as public scrutiny.


In this episode, Parag shares what he learned from his time at Twitter, why the web must evolve to serve AI at massive scale, how Parallel is tackling “deep research” challenges by prioritizing accuracy over speed, and the design choices that make their APIs uniquely agent-friendly.


We also discuss:

  • Why Parallel designs for AI as the primary customer
  • Lessons from 11 years at Twitter and applying them to a startup
  • Potential business models to keep the web open for AI
  • Hiring philosophy: balancing high potential and experienced talent
  • The evolving role of engineers in an AI-assisted world
  • Why “agents” are finally becoming useful in production
  • And much more…

References:

Where to find Parag:

Where to find Todd:

Where to find First Round Capital:

Timestamps:

(1:26) Founding Parallel with an AI-first mission

(3:23) From Twitter CTO/CEO to startup founder

(6:20) What the AI era spells for companies

(7:58) The CEO to founder pipeline

(11:18) Reflections on Twitter’s transformation

(17:48) How Parallel was born

(22:31) Early use cases for Parallel

(31:42) How has Parallel’s ICP changed?

(34:37) AI’s impact on competitor dynamics

(36:06) When should founders launch?

(37:43) Parag’s fundraising framework

(40:14) Building a high-impact engineering team

(44:49) Counterproductive uses of AI

(47:35) How will the software engineer role evolve?

(49:10) How are Parallel’s customers using AI?

(53:27) Defining agents in 2025

(55:02) Parallel’s long-term vision

(1:03:43) Parag’s growth as a founder

]]> 3935 Ignoring Silicon Valley advice to build a $3B fintech unicorn | Immad Akhund (Co-founder and CEO of Mercury) Immad Akhund is the CEO and co-founder of Mercury, a digital banking platform that’s become the go-to financial infrastructure for startups. Before Mercury, Immad spent nearly two decades founding companies, learning the hard way what separates a good idea from a great business. In this episode, Immad shares the hard-earned lessons from launching Mercury as his third startup. He unpacks how he recognized this was the right idea to pursue, what strong product-market fit feels like, and why trying to "iterate" your way to success often leads founders astray. In this episode, we discuss: Mercury’s unusual culture playbook – and why it works How to hire with intention The trap of weak product-market fit Shipping under intense pressure during the SVB crisis And much more… References: Airbnb: https://www.airbnb.com/ Andreessen Horowitz: https://a16z.com/ Apple: https://www.apple.com/ Block: https://block.xyz/ Brex: https://www.brex.com/ Chime: https://www.chime.com/ Gusto: https://gusto.com/ Mercury: https://mercury.com/ Paul Graham: https://x.com/paulg Plaid: https://plaid.com/ Stripe: https://stripe.com/ SVB (Silicon Valley Bank): https://www.svb.com/ True Link Financial: https://www.truelinkfinancial.com/ Varo: https://www.varomoney.com/ Y Combinator: https://www.ycombinator.com/ Where to find Immad: LinkedIn: https://www.linkedin.com/in/iakhund/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: (1:07) Hard-won lessons from serial entrepreneurship (2:02) You shouldn’t copy-paste advice (6:57) Why personality trumps culture playbooks (8:48) How do you hire for cultural fit? (12:38) The values that shaped Mercury’s DNA (14:08) The drivers underpinning Mercury’s success (15:50) The significance of product-market fit (20:41) Don’t fall into the weak product-market fit trap (25:49) How to evaluate startup ideas that scale (30:14) Mercury’s unlikely origin story (33:51) Breaking into the fintech space (37:31) Mindset shift: From “This is hard” to long-term gains (39:43) Building Mercury’s MVP (44:25) Overcoming early obstacles to reach launch (47:36) Navigating Mercury’s rapid growth phase (51:18) Competition isn’t the reason you’re failing (55:58) Crisis management during the SVB collapse Wed, 06 Aug 2025 13:56:00 -0000 full First Round Immad Akhund is the CEO and co-founder of Mercury, a digital banking platform that’s become the go-to financial infrastructure for startups. Before Mercury, Immad spent nearly two decades founding companies, learning the hard way what separates a good idea from a great business. In this episode, Immad shares the hard-earned lessons from launching Mercury as his third startup. He unpacks how he recognized this was the right idea to pursue, what strong product-market fit feels like, and why trying to "iterate" your way to success often leads founders astray. In this episode, we discuss: Mercury’s unusual culture playbook – and why it works How to hire with intention The trap of weak product-market fit Shipping under intense pressure during the SVB crisis And much more… References: Airbnb: https://www.airbnb.com/ Andreessen Horowitz: https://a16z.com/ Apple: https://www.apple.com/ Block: https://block.xyz/ Brex: https://www.brex.com/ Chime: https://www.chime.com/ Gusto: https://gusto.com/ Mercury: https://mercury.com/ Paul Graham: https://x.com/paulg Plaid: https://plaid.com/ Stripe: https://stripe.com/ SVB (Silicon Valley Bank): https://www.svb.com/ True Link Financial: https://www.truelinkfinancial.com/ Varo: https://www.varomoney.com/ Y Combinator: https://www.ycombinator.com/ Where to find Immad: LinkedIn: https://www.linkedin.com/in/iakhund/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: (1:07) Hard-won lessons from serial entrepreneurship (2:02) You shouldn’t copy-paste advice (6:57) Why personality trumps culture playbooks (8:48) How do you hire for cultural fit? (12:38) The values that shaped Mercury’s DNA (14:08) The drivers underpinning Mercury’s success (15:50) The significance of product-market fit (20:41) Don’t fall into the weak product-market fit trap (25:49) How to evaluate startup ideas that scale (30:14) Mercury’s unlikely origin story (33:51) Breaking into the fintech space (37:31) Mindset shift: From “This is hard” to long-term gains (39:43) Building Mercury’s MVP (44:25) Overcoming early obstacles to reach launch (47:36) Navigating Mercury’s rapid growth phase (51:18) Competition isn’t the reason you’re failing (55:58) Crisis management during the SVB collapse Immad Akhund is the CEO and co-founder of Mercury, a digital banking platform that’s become the go-to financial infrastructure for startups. Before Mercury, Immad spent nearly two decades founding companies, learning the hard way what separates a good idea from a great business.


In this episode, Immad shares the hard-earned lessons from launching Mercury as his third startup. He unpacks how he recognized this was the right idea to pursue, what strong product-market fit feels like, and why trying to "iterate" your way to success often leads founders astray.


In this episode, we discuss:

  • Mercury’s unusual culture playbook – and why it works
  • How to hire with intention
  • The trap of weak product-market fit
  • Shipping under intense pressure during the SVB crisis
  • And much more…


References:


Where to find Immad:


Where to find Brett:


Where to find First Round Capital:


Timestamps:

  • (1:07) Hard-won lessons from serial entrepreneurship
  • (2:02) You shouldn’t copy-paste advice
  • (6:57) Why personality trumps culture playbooks
  • (8:48) How do you hire for cultural fit?
  • (12:38) The values that shaped Mercury’s DNA
  • (14:08) The drivers underpinning Mercury’s success
  • (15:50) The significance of product-market fit
  • (20:41) Don’t fall into the weak product-market fit trap
  • (25:49) How to evaluate startup ideas that scale
  • (30:14) Mercury’s unlikely origin story
  • (33:51) Breaking into the fintech space
  • (37:31) Mindset shift: From “This is hard” to long-term gains
  • (39:43) Building Mercury’s MVP
  • (44:25) Overcoming early obstacles to reach launch
  • (47:36) Navigating Mercury’s rapid growth phase
  • (51:18) Competition isn’t the reason you’re failing
  • (55:58) Crisis management during the SVB collapse
]]> 3712 Inside the ex-YC partner’s $15B self driving car company | Qasar Younis Qasar Younis is the co-founder and CEO of Applied Intuition, a leading vehicle intelligence platform that helps companies develop and deploy autonomous systems at scale. In June 2025, the company raised $600M at a $15B valuation. Before Applied Intuition, Qasar was the COO and a group partner at Y Combinator, and earlier founded TalkBin, which was acquired by Google. He’s also held engineering roles at General Motors and Bosch. In today’s episode, we discuss: • The two founder traits Silicon Valley undervalues • How to get 1–3 extra months of work done every year • Lessons from YC on pattern matching and founder feedback • The battle-tested startup formula Qasar used at Applied • Why co-founder fit is make-or-break • Applied’s playbook: vertical SaaS, product-led GTM, and leveraging VC networks • Why Applied went multi-product in the early days • Contrarian takes on startup culture, compensation, and cost control • Why domain expertise is making a comeback • And much more… Referenced: • Applied Intuition: https://www.appliedintuition.com • Ansys: https://www.ansys.com • Bilal Zuberi: https://www.linkedin.com/in/bzuberi • Bosch: https://www.bosch.com • Elad Gil: https://www.linkedin.com/in/eladgil • General Motors: https://www.gm.com • “Google’s Acquisition of TalkBin”: https://techcrunch.com/2011/04/25/google-acquires-talkbin-a-feedback-platform-for-businesses-thats-only-five-months-old/ • “High Output Management”: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 • Kyle Vogt: https://x.com/kvogt • Marc Andreessen: https://x.com/pmarca • “Only the Paranoid Survive”: https://www.amazon.com/Only-Paranoid-Survive-Strategic-Inflection/dp/0385483821 • Paul Graham: https://x.com/paulg • Peter Ludwig: https://www.linkedin.com/in/peterwludwig • Sam Altman: https://x.com/sama • TalkBin: https://www.crunchbase.com/organization/talkbin • “The History of the Standard Oil Company”: https://www.amazon.com/History-Standard-Oil-Company-Volumes/dp/1519455860 • Waymo: https://waymo.com • Y Combinator: https://www.ycombinator.com • Zoox: https://zoox.com Where to find Qasar: • LinkedIn: https://www.linkedin.com/in/qasar/ Where to find Brett: • LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ • Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: • Website: https://firstround.com/ • First Round Review: https://review.firstround.com/ • Twitter/X: https://twitter.com/firstround • YouTube: https://www.youtube.com/@FirstRoundCapital • This podcast on all platforms: https://review.firstround.com/podcast Timestamps: (01:26) Two founder traits Silicon Valley undervalues (04:23) Gain 1-3 extra months of productivity yearly (05:52) Why founders should read outside the startup canon (07:27) Lessons from YC (13:44) Why it's harder to start than to quit (15:52) The moment you become a real founder (20:24) How great founders master luck (21:46) Qasar’s battle-tested startup formula (25:37) The founding insight for Applied (31:42) How Applied expanded beyond automotive (38:05) Why Applied went multi-product early (45:45) What no one says about startup secondaries (49:02) Why being cheap is a startup superpower (51:04) The myth of "competition doesn’t matter" (53:50) Early scrappiness: The Sunnyvale house setup (54:50) Why domain knowledge is making a comeback (58:32) The mentors who shaped Qasar Fri, 01 Aug 2025 16:19:00 -0000 full First Round Qasar Younis is the co-founder and CEO of Applied Intuition, a leading vehicle intelligence platform that helps companies develop and deploy autonomous systems at scale. In June 2025, the company raised $600M at a $15B valuation. Before Applied Intuition, Qasar was the COO and a group partner at Y Combinator, and earlier founded TalkBin, which was acquired by Google. He’s also held engineering roles at General Motors and Bosch. In today’s episode, we discuss: • The two founder traits Silicon Valley undervalues • How to get 1–3 extra months of work done every year • Lessons from YC on pattern matching and founder feedback • The battle-tested startup formula Qasar used at Applied • Why co-founder fit is make-or-break • Applied’s playbook: vertical SaaS, product-led GTM, and leveraging VC networks • Why Applied went multi-product in the early days • Contrarian takes on startup culture, compensation, and cost control • Why domain expertise is making a comeback • And much more… Referenced: • Applied Intuition: https://www.appliedintuition.com • Ansys: https://www.ansys.com • Bilal Zuberi: https://www.linkedin.com/in/bzuberi • Bosch: https://www.bosch.com • Elad Gil: https://www.linkedin.com/in/eladgil • General Motors: https://www.gm.com • “Google’s Acquisition of TalkBin”: https://techcrunch.com/2011/04/25/google-acquires-talkbin-a-feedback-platform-for-businesses-thats-only-five-months-old/ • “High Output Management”: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 • Kyle Vogt: https://x.com/kvogt • Marc Andreessen: https://x.com/pmarca • “Only the Paranoid Survive”: https://www.amazon.com/Only-Paranoid-Survive-Strategic-Inflection/dp/0385483821 • Paul Graham: https://x.com/paulg • Peter Ludwig: https://www.linkedin.com/in/peterwludwig • Sam Altman: https://x.com/sama • TalkBin: https://www.crunchbase.com/organization/talkbin • “The History of the Standard Oil Company”: https://www.amazon.com/History-Standard-Oil-Company-Volumes/dp/1519455860 • Waymo: https://waymo.com • Y Combinator: https://www.ycombinator.com • Zoox: https://zoox.com Where to find Qasar: • LinkedIn: https://www.linkedin.com/in/qasar/ Where to find Brett: • LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ • Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: • Website: https://firstround.com/ • First Round Review: https://review.firstround.com/ • Twitter/X: https://twitter.com/firstround • YouTube: https://www.youtube.com/@FirstRoundCapital • This podcast on all platforms: https://review.firstround.com/podcast Timestamps: (01:26) Two founder traits Silicon Valley undervalues (04:23) Gain 1-3 extra months of productivity yearly (05:52) Why founders should read outside the startup canon (07:27) Lessons from YC (13:44) Why it's harder to start than to quit (15:52) The moment you become a real founder (20:24) How great founders master luck (21:46) Qasar’s battle-tested startup formula (25:37) The founding insight for Applied (31:42) How Applied expanded beyond automotive (38:05) Why Applied went multi-product early (45:45) What no one says about startup secondaries (49:02) Why being cheap is a startup superpower (51:04) The myth of "competition doesn’t matter" (53:50) Early scrappiness: The Sunnyvale house setup (54:50) Why domain knowledge is making a comeback (58:32) The mentors who shaped Qasar Qasar Younis is the co-founder and CEO of Applied Intuition, a leading vehicle intelligence platform that helps companies develop and deploy autonomous systems at scale. In June 2025, the company raised $600M at a $15B valuation. Before Applied Intuition, Qasar was the COO and a group partner at Y Combinator, and earlier founded TalkBin, which was acquired by Google. He’s also held engineering roles at General Motors and Bosch. In today’s episode, we discuss: • The two founder traits Silicon Valley undervalues • How to get 1–3 extra months of work done every year • Lessons from YC on pattern matching and founder feedback • The battle-tested startup formula Qasar used at Applied • Why co-founder fit is make-or-break • Applied’s playbook: vertical SaaS, product-led GTM, and leveraging VC networks • Why Applied went multi-product in the early days • Contrarian takes on startup culture, compensation, and cost control • Why domain expertise is making a comeback • And much more… Referenced: • Applied Intuition: https://www.appliedintuition.com • Ansys: https://www.ansys.com • Bilal Zuberi: https://www.linkedin.com/in/bzuberi • Bosch: https://www.bosch.com • Elad Gil: https://www.linkedin.com/in/eladgil • General Motors: https://www.gm.com • “Google’s Acquisition of TalkBin”: https://techcrunch.com/2011/04/25/google-acquires-talkbin-a-feedback-platform-for-businesses-thats-only-five-months-old/ • “High Output Management”: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 • Kyle Vogt: https://x.com/kvogt • Marc Andreessen: https://x.com/pmarca • “Only the Paranoid Survive”: https://www.amazon.com/Only-Paranoid-Survive-Strategic-Inflection/dp/0385483821 • Paul Graham: https://x.com/paulg • Peter Ludwig: https://www.linkedin.com/in/peterwludwig • Sam Altman: https://x.com/sama • TalkBin: https://www.crunchbase.com/organization/talkbin • “The History of the Standard Oil Company”: https://www.amazon.com/History-Standard-Oil-Company-Volumes/dp/1519455860 • Waymo: https://waymo.com • Y Combinator: https://www.ycombinator.com • Zoox: https://zoox.com Where to find Qasar: • LinkedIn: https://www.linkedin.com/in/qasar/ Where to find Brett: • LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ • Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: • Website: https://firstround.com/ • First Round Review: https://review.firstround.com/ • Twitter/X: https://twitter.com/firstround • YouTube: https://www.youtube.com/@FirstRoundCapital • This podcast on all platforms: https://review.firstround.com/podcast Timestamps: (01:26) Two founder traits Silicon Valley undervalues (04:23) Gain 1-3 extra months of productivity yearly (05:52) Why founders should read outside the startup canon (07:27) Lessons from YC (13:44) Why it's harder to start than to quit (15:52) The moment you become a real founder (20:24) How great founders master luck (21:46) Qasar’s battle-tested startup formula (25:37) The founding insight for Applied (31:42) How Applied expanded beyond automotive (38:05) Why Applied went multi-product early (45:45) What no one says about startup secondaries (49:02) Why being cheap is a startup superpower (51:04) The myth of "competition doesn’t matter" (53:50) Early scrappiness: The Sunnyvale house setup (54:50) Why domain knowledge is making a comeback (58:32) The mentors who shaped Qasar

]]> 3625 What Braintrust got right about product-market fit | Ankur Goyal (Founder and CEO) Ankur Goyal is the founder and CEO of Braintrust, an end-to-end platform for building AI apps. Before that, he founded Impira, a data management platform that was acquired by Figma, where he went on to lead the AI team. Ankur kickstarted his career when he dropped out of college to join the founding team at SingleStore (formerly MemSQL), a formative experience that shaped his views on building for high-bar users. In today’s episode, we discuss: • Ankur’s early lessons on quality from MemSQL • How frustration with evals at Figma led to Braintrust • Why they delayed go-to-market (on purpose) • How to find product-market fit in a new market • Why building great software comes from a place of “paranoia” • And much more… Referenced: • Airtable: https://www.airtable.com/ • Adam Prout: https://www.linkedin.com/in/adam-prout-0b347630/ • Braintrust: https://braintrust.dev • Brian Helmig: https://www.linkedin.com/in/bryanhelmig/ • Coda: https://coda.io/ • Databricks: https://www.databricks.com/ • David Kossnick: https://www.linkedin.com/in/davidkossnick/ • Figma: https://www.figma.com/ • Goldman Sachs: https://www.goldmansachs.com/ • Kris Rasmussen: https://www.linkedin.com/in/kristopherrasmussen/ • Manu Goyal: https://www.linkedin.com/in/mngyl/ • MemSQL: https://www.singlestore.com/ (now SingleStore) • Nikita Shamgunov: https://www.linkedin.com/in/nikitashamgunov/ • OpenAI: https://openai.com/ • Snowflake: https://www.snowflake.com/ • Zapier: https://zapier.com/ Where to find Ankur: • LinkedIn: https://www.linkedin.com/in/ankrgyl/ • Twitter/X: https://x.com/ankrgyl Where to find Brett: • LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ • Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: • Website: https://firstround.com/ • First Round Review: https://review.firstround.com/ • Twitter/X: https://twitter.com/firstround • YouTube: https://www.youtube.com/@FirstRoundCapital • This podcast on all platforms: https://review.firstround.com/podcast Timestamps (02:02) Dropping out of college to join MemSQL (02:24) Key lessons from MemSQL (05:54) How to build quality software (08:51) The trick to recruiting well (12:03) Founding Impira and selling to Figma (19:45) How Braintrust was born (25:33) Why good founders are paranoid (28:08) How to recognize a real market opportunity (33:37) The biggest mistake at Impira (35:15) Inside Braintrust’s first six months (40:57) How AI is reshaping Braintrust’s future (42:32) The evolution of their prompt playground (46:53) Fighting to stay mission-driven (52:45) Make big bets, with extreme clarity (57:00) The cultural choices that shaped Braintrust (58:49) Hiring mistakes they won’t repeat (1:03:07) What PMF really looks like Thu, 24 Jul 2025 19:57:00 -0000 full First Round Ankur Goyal is the founder and CEO of Braintrust, an end-to-end platform for building AI apps. Before that, he founded Impira, a data management platform that was acquired by Figma, where he went on to lead the AI team. Ankur kickstarted his career when he dropped out of college to join the founding team at SingleStore (formerly MemSQL), a formative experience that shaped his views on building for high-bar users. In today’s episode, we discuss: • Ankur’s early lessons on quality from MemSQL • How frustration with evals at Figma led to Braintrust • Why they delayed go-to-market (on purpose) • How to find product-market fit in a new market • Why building great software comes from a place of “paranoia” • And much more… Referenced: • Airtable: https://www.airtable.com/ • Adam Prout: https://www.linkedin.com/in/adam-prout-0b347630/ • Braintrust: https://braintrust.dev • Brian Helmig: https://www.linkedin.com/in/bryanhelmig/ • Coda: https://coda.io/ • Databricks: https://www.databricks.com/ • David Kossnick: https://www.linkedin.com/in/davidkossnick/ • Figma: https://www.figma.com/ • Goldman Sachs: https://www.goldmansachs.com/ • Kris Rasmussen: https://www.linkedin.com/in/kristopherrasmussen/ • Manu Goyal: https://www.linkedin.com/in/mngyl/ • MemSQL: https://www.singlestore.com/ (now SingleStore) • Nikita Shamgunov: https://www.linkedin.com/in/nikitashamgunov/ • OpenAI: https://openai.com/ • Snowflake: https://www.snowflake.com/ • Zapier: https://zapier.com/ Where to find Ankur: • LinkedIn: https://www.linkedin.com/in/ankrgyl/ • Twitter/X: https://x.com/ankrgyl Where to find Brett: • LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ • Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: • Website: https://firstround.com/ • First Round Review: https://review.firstround.com/ • Twitter/X: https://twitter.com/firstround • YouTube: https://www.youtube.com/@FirstRoundCapital • This podcast on all platforms: https://review.firstround.com/podcast Timestamps (02:02) Dropping out of college to join MemSQL (02:24) Key lessons from MemSQL (05:54) How to build quality software (08:51) The trick to recruiting well (12:03) Founding Impira and selling to Figma (19:45) How Braintrust was born (25:33) Why good founders are paranoid (28:08) How to recognize a real market opportunity (33:37) The biggest mistake at Impira (35:15) Inside Braintrust’s first six months (40:57) How AI is reshaping Braintrust’s future (42:32) The evolution of their prompt playground (46:53) Fighting to stay mission-driven (52:45) Make big bets, with extreme clarity (57:00) The cultural choices that shaped Braintrust (58:49) Hiring mistakes they won’t repeat (1:03:07) What PMF really looks like Ankur Goyal is the founder and CEO of Braintrust, an end-to-end platform for building AI apps. Before that, he founded Impira, a data management platform that was acquired by Figma, where he went on to lead the AI team. Ankur kickstarted his career when he dropped out of college to join the founding team at SingleStore (formerly MemSQL), a formative experience that shaped his views on building for high-bar users.


In today’s episode, we discuss:

• Ankur’s early lessons on quality from MemSQL

• How frustration with evals at Figma led to Braintrust

• Why they delayed go-to-market (on purpose)

• How to find product-market fit in a new market

• Why building great software comes from a place of “paranoia”

• And much more…


Referenced:

• Airtable: https://www.airtable.com/

• Adam Prout: https://www.linkedin.com/in/adam-prout-0b347630/

• Braintrust: https://braintrust.dev

• Brian Helmig: https://www.linkedin.com/in/bryanhelmig/

• Coda: https://coda.io/

• Databricks: https://www.databricks.com/

• David Kossnick: https://www.linkedin.com/in/davidkossnick/

• Figma: https://www.figma.com/

• Goldman Sachs: https://www.goldmansachs.com/

• Kris Rasmussen: https://www.linkedin.com/in/kristopherrasmussen/

• Manu Goyal: https://www.linkedin.com/in/mngyl/

• MemSQL: https://www.singlestore.com/ (now SingleStore)

• Nikita Shamgunov: https://www.linkedin.com/in/nikitashamgunov/

• OpenAI: https://openai.com/

• Snowflake: https://www.snowflake.com/

• Zapier: https://zapier.com/


Where to find Ankur:

• LinkedIn: https://www.linkedin.com/in/ankrgyl/

• Twitter/X: https://x.com/ankrgyl


Where to find Brett:

• LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/

• Twitter/X: https://twitter.com/brettberson


Where to find First Round Capital:

• Website: https://firstround.com/

• First Round Review: https://review.firstround.com/

• Twitter/X: https://twitter.com/firstround

• YouTube: https://www.youtube.com/@FirstRoundCapital

• This podcast on all platforms: https://review.firstround.com/podcast


Timestamps

(02:02) Dropping out of college to join MemSQL

(02:24) Key lessons from MemSQL

(05:54) How to build quality software

(08:51) The trick to recruiting well

(12:03) Founding Impira and selling to Figma

(19:45) How Braintrust was born

(25:33) Why good founders are paranoid

(28:08) How to recognize a real market opportunity

(33:37) The biggest mistake at Impira

(35:15) Inside Braintrust’s first six months

(40:57) How AI is reshaping Braintrust’s future

(42:32) The evolution of their prompt playground

(46:53) Fighting to stay mission-driven

(52:45) Make big bets, with extreme clarity

(57:00) The cultural choices that shaped Braintrust

(58:49) Hiring mistakes they won’t repeat

(1:03:07) What PMF really looks like

]]> 4204 How Gusto built a $9.5 billion company by identifying a burning problem Tomer London is the co-founder and Chief Product Officer at Gusto, the payroll and people platform used by over 400,000 businesses. He grew up helping run his dad’s clothing store in Israel — an experience that sparked his mission to build better tools for small business owners. After moving to the US for a PhD at Stanford, he met his co-founders and started Gusto. In today’s episode, we discuss: Reinventing payroll without any prior experience Why you should hire for humility, not just talent Gusto’s scrappy customer research: cold calling from a walk-in closet Why founders should embrace customer rejection Why “emotional urgency” matters more than polite feedback The weekly co-founder ritual that built trust How Gusto expanded from payroll to a multi-product platform Building products customers actually love And so much more Referenced: ADP Eddie Kim Gusto Intuit Josh Reeves Paychex Steve Jobs’ “Secrets to Life” clip Steve Jobs’ Stanford Commencement Speech Wells Fargo Y Combinator Where to find Tomer: LinkedIn Twitter/X Where to find Brett: LinkedIn Twitter/X Where to find First Round Capital: Website First Round Review Twitter/X YouTube This podcast on all platforms Timestamps: (00:00) How a childhood around SMBs shaped Tomer’s founder mindset (03:24) The three things that led to the creation of Gusto (07:17) Hiring for humility, not just talent (09:28) The tug-of-war test for product-market fit (11:58) Why founders should actively seek rejection (15:34) Gusto’s scrappy customer research: cold calling from a walk-in closet (17:45) Betting on SMBs – and ignoring investor advice (20:44) “It’s not an MVP, it’s something that wows people” (24:09) Serving SMBs vs. startups (28:36) How to find the right co-founders (31:09) The weekly co-founder ritual that built trust (35:02) Reinventing payroll without any prior experience (38:49) Gusto’s “start small” GTM playbook (42:16) The big opportunity Gusto wishes they tackled sooner (43:58) How switching costs became Gusto’s moat (47:25) The two lucky breaks that gave Gusto an edge (51:56) What Tomer learned about customers from his dad’s clothing store Tue, 01 Jul 2025 05:00:00 -0000 full First Round Tomer London is the co-founder and Chief Product Officer at Gusto, the payroll and people platform used by over 400,000 businesses. He grew up helping run his dad’s clothing store in Israel — an experience that sparked his mission to build better tools for small business owners. After moving to the US for a PhD at Stanford, he met his co-founders and started Gusto. In today’s episode, we discuss: Reinventing payroll without any prior experience Why you should hire for humility, not just talent Gusto’s scrappy customer research: cold calling from a walk-in closet Why founders should embrace customer rejection Why “emotional urgency” matters more than polite feedback The weekly co-founder ritual that built trust How Gusto expanded from payroll to a multi-product platform Building products customers actually love And so much more Referenced: ADP Eddie Kim Gusto Intuit Josh Reeves Paychex Steve Jobs’ “Secrets to Life” clip Steve Jobs’ Stanford Commencement Speech Wells Fargo Y Combinator Where to find Tomer: LinkedIn Twitter/X Where to find Brett: LinkedIn Twitter/X Where to find First Round Capital: Website First Round Review Twitter/X YouTube This podcast on all platforms Timestamps: (00:00) How a childhood around SMBs shaped Tomer’s founder mindset (03:24) The three things that led to the creation of Gusto (07:17) Hiring for humility, not just talent (09:28) The tug-of-war test for product-market fit (11:58) Why founders should actively seek rejection (15:34) Gusto’s scrappy customer research: cold calling from a walk-in closet (17:45) Betting on SMBs – and ignoring investor advice (20:44) “It’s not an MVP, it’s something that wows people” (24:09) Serving SMBs vs. startups (28:36) How to find the right co-founders (31:09) The weekly co-founder ritual that built trust (35:02) Reinventing payroll without any prior experience (38:49) Gusto’s “start small” GTM playbook (42:16) The big opportunity Gusto wishes they tackled sooner (43:58) How switching costs became Gusto’s moat (47:25) The two lucky breaks that gave Gusto an edge (51:56) What Tomer learned about customers from his dad’s clothing store Tomer London is the co-founder and Chief Product Officer at Gusto, the payroll and people platform used by over 400,000 businesses. He grew up helping run his dad’s clothing store in Israel — an experience that sparked his mission to build better tools for small business owners. After moving to the US for a PhD at Stanford, he met his co-founders and started Gusto.


In today’s episode, we discuss:

  • Reinventing payroll without any prior experience
  • Why you should hire for humility, not just talent
  • Gusto’s scrappy customer research: cold calling from a walk-in closet
  • Why founders should embrace customer rejection
  • Why “emotional urgency” matters more than polite feedback
  • The weekly co-founder ritual that built trust
  • How Gusto expanded from payroll to a multi-product platform
  • Building products customers actually love
  • And so much more

Referenced:


Where to find Tomer:


Where to find Brett:


Where to find First Round Capital:


Timestamps:

(00:00) How a childhood around SMBs shaped Tomer’s founder mindset

(03:24) The three things that led to the creation of Gusto

(07:17) Hiring for humility, not just talent

(09:28) The tug-of-war test for product-market fit

(11:58) Why founders should actively seek rejection

(15:34) Gusto’s scrappy customer research: cold calling from a walk-in closet

(17:45) Betting on SMBs – and ignoring investor advice

(20:44) “It’s not an MVP, it’s something that wows people”

(24:09) Serving SMBs vs. startups

(28:36) How to find the right co-founders

(31:09) The weekly co-founder ritual that built trust

(35:02) Reinventing payroll without any prior experience

(38:49) Gusto’s “start small” GTM playbook

(42:16) The big opportunity Gusto wishes they tackled sooner

(43:58) How switching costs became Gusto’s moat

(47:25) The two lucky breaks that gave Gusto an edge

(51:56) What Tomer learned about customers from his dad’s clothing store

]]> 3301 How rejecting conventional wisdom grew Sentry to a $3 billion company | David Cramer (Co-founder and CPO) David Cramer is the co-founder of Sentry, the leading open-source error monitoring tool used by over 90,000 companies. A self-taught engineer, he went from 9th grade high school dropout and Burger King manager to building one of the most widely adopted developer tools in the world — by working hard and rejecting conventional wisdom. As of 2022, Sentry is valued at over $3 billion. David now serves as Chief Product Officer, after previously holding roles as CEO and CTO. In this episode, we discuss: How David went from managing a Burger King to landing his first job as a software engineer How an code snippet grew into a ubiquitous monitoring platform Why open source is an underrated distribution hack How a ruthless competitive streak and obsession with excellence fueled Sentry’s rise And so much more… Referenced: Aaron Levie Beats by Dre Cursor Dan Levine Datadog Disqus Dropbox Heroku Max Levchin Okta Omar Johnson Oracle Sentry Satya Nadella Stripe Uber VS Code WindSurf Y Combinator Yandex Where to find David: LinkedIn Twitter/X Where to find Brett: LinkedIn Twitter/X Where to find First Round Capital: Website First Round Review Twitter/X YouTube Timestamps: (4:01) Learning to code through gaming (6:31) Dropping out of high school (9:47) Building infrastructure at Disqus (10:20) “Software is not that hard” (12:45) Early interest in open source (15:45) The birth of Sentry (23:37) Two common founder mistakes (27:13) David’s unwavering focus (28:17) Sentry’s journey to venture backing (36:43) Finding conviction in decisions (41:11) How Sentry found PMF (46:34) More confidence, less ego (48:08) Is sales valuable? (51:31) David’s personal philosophy (1:01:17) Money is not the hardest problem (1:06:27) Marketing won’t fix a bad product (1:10:34) What makes Sentry’s market unique (1:16:24) “You’re gonna mess up” (1:22:08) Why brand will always matter (1:30:51) Eliminating all competition Thu, 19 Jun 2025 15:32:00 -0000 full First Round David Cramer is the co-founder of Sentry, the leading open-source error monitoring tool used by over 90,000 companies. A self-taught engineer, he went from 9th grade high school dropout and Burger King manager to building one of the most widely adopted developer tools in the world — by working hard and rejecting conventional wisdom. As of 2022, Sentry is valued at over $3 billion. David now serves as Chief Product Officer, after previously holding roles as CEO and CTO. In this episode, we discuss: How David went from managing a Burger King to landing his first job as a software engineer How an code snippet grew into a ubiquitous monitoring platform Why open source is an underrated distribution hack How a ruthless competitive streak and obsession with excellence fueled Sentry’s rise And so much more… Referenced: Aaron Levie Beats by Dre Cursor Dan Levine Datadog Disqus Dropbox Heroku Max Levchin Okta Omar Johnson Oracle Sentry Satya Nadella Stripe Uber VS Code WindSurf Y Combinator Yandex Where to find David: LinkedIn Twitter/X Where to find Brett: LinkedIn Twitter/X Where to find First Round Capital: Website First Round Review Twitter/X YouTube Timestamps: (4:01) Learning to code through gaming (6:31) Dropping out of high school (9:47) Building infrastructure at Disqus (10:20) “Software is not that hard” (12:45) Early interest in open source (15:45) The birth of Sentry (23:37) Two common founder mistakes (27:13) David’s unwavering focus (28:17) Sentry’s journey to venture backing (36:43) Finding conviction in decisions (41:11) How Sentry found PMF (46:34) More confidence, less ego (48:08) Is sales valuable? (51:31) David’s personal philosophy (1:01:17) Money is not the hardest problem (1:06:27) Marketing won’t fix a bad product (1:10:34) What makes Sentry’s market unique (1:16:24) “You’re gonna mess up” (1:22:08) Why brand will always matter (1:30:51) Eliminating all competition David Cramer is the co-founder of Sentry, the leading open-source error monitoring tool used by over 90,000 companies. A self-taught engineer, he went from 9th grade high school dropout and Burger King manager to building one of the most widely adopted developer tools in the world — by working hard and rejecting conventional wisdom. As of 2022, Sentry is valued at over $3 billion. David now serves as Chief Product Officer, after previously holding roles as CEO and CTO.


In this episode, we discuss:

  • How David went from managing a Burger King to landing his first job as a software engineer
  • How an code snippet grew into a ubiquitous monitoring platform
  • Why open source is an underrated distribution hack
  • How a ruthless competitive streak and obsession with excellence fueled Sentry’s rise
  • And so much more…


Referenced:


Where to find David:


Where to find Brett:

Where to find First Round Capital:


Timestamps:

(4:01) Learning to code through gaming

(6:31) Dropping out of high school

(9:47) Building infrastructure at Disqus

(10:20) “Software is not that hard”

(12:45) Early interest in open source

(15:45) The birth of Sentry

(23:37) Two common founder mistakes

(27:13) David’s unwavering focus

(28:17) Sentry’s journey to venture backing

(36:43) Finding conviction in decisions

(41:11) How Sentry found PMF

(46:34) More confidence, less ego

(48:08) Is sales valuable?

(51:31) David’s personal philosophy

(1:01:17) Money is not the hardest problem

(1:06:27) Marketing won’t fix a bad product

(1:10:34) What makes Sentry’s market unique

(1:16:24) “You’re gonna mess up”

(1:22:08) Why brand will always matter

(1:30:51) Eliminating all competition

]]> 6084 Inside Linear: Why craft and focus still win in product building | Karri Saarinen (Co-founder and CEO) Karri Saarinen is the co-founder and CEO of Linear, the project management tool built for high-performance software teams. Since its founding in 2019, Linear has achieved a valuation of $1.25B as of 10th June 2025 and now counts companies like OpenAI, Ramp and Vercel as customers. Before founding Linear, Karri led design at Airbnb and Coinbase, and previously co-founded Kippt, a bookmarking tool acquired by Coinbase. In today’s episode, we discuss Karri’s childhood love for computers that shaped his career The lessons he learned from a failed first startup Linear’s founding principles The early validation strategies used to shape the product Why Karri believes in small teams And much more… Referenced Airbnb Brian Armstrong Brian Chesky Coinbase Jori Lallo Linear Tuomas Artman Y Combinator Where to find Karri LinkedIn Twitter/X Where to find Brett LinkedIn Twitter/X Where to find First Round Capital Website First Round Review Twitter/X YouTube Timestamps (1:37) Childhood roots in computers and design (6:54) Founding Kippt and lessons from a failed bookmarking startup (13:14) Lessons from a serial entrepreneur (19:32) Why teams shouldn’t grow too quickly (25: 03) Linear’s early beginnings (36:55) The unexpected power of intuition (42:41) Linear’s unusual approach to user growth (47:29) What shaped Linear’s early product roadmap (52:02) Startups shouldn’t try to boil the ocean (57:30) The power of extreme focus (59:18) Design “something for someone” (1:04:29) Flexibility vs. simplicity (1:17:27) Lead your team with strong principles (1:24:45) Design founders vs. engineering founders Tue, 10 Jun 2025 16:57:00 -0000 full First Round Karri Saarinen is the co-founder and CEO of Linear, the project management tool built for high-performance software teams. Since its founding in 2019, Linear has achieved a valuation of $1.25B as of 10th June 2025 and now counts companies like OpenAI, Ramp and Vercel as customers. Before founding Linear, Karri led design at Airbnb and Coinbase, and previously co-founded Kippt, a bookmarking tool acquired by Coinbase. In today’s episode, we discuss Karri’s childhood love for computers that shaped his career The lessons he learned from a failed first startup Linear’s founding principles The early validation strategies used to shape the product Why Karri believes in small teams And much more… Referenced Airbnb Brian Armstrong Brian Chesky Coinbase Jori Lallo Linear Tuomas Artman Y Combinator Where to find Karri LinkedIn Twitter/X Where to find Brett LinkedIn Twitter/X Where to find First Round Capital Website First Round Review Twitter/X YouTube Timestamps (1:37) Childhood roots in computers and design (6:54) Founding Kippt and lessons from a failed bookmarking startup (13:14) Lessons from a serial entrepreneur (19:32) Why teams shouldn’t grow too quickly (25: 03) Linear’s early beginnings (36:55) The unexpected power of intuition (42:41) Linear’s unusual approach to user growth (47:29) What shaped Linear’s early product roadmap (52:02) Startups shouldn’t try to boil the ocean (57:30) The power of extreme focus (59:18) Design “something for someone” (1:04:29) Flexibility vs. simplicity (1:17:27) Lead your team with strong principles (1:24:45) Design founders vs. engineering founders Karri Saarinen is the co-founder and CEO of Linear, the project management tool built for high-performance software teams. Since its founding in 2019, Linear has achieved a valuation of $1.25B as of 10th June 2025 and now counts companies like OpenAI, Ramp and Vercel as customers. Before founding Linear, Karri led design at Airbnb and Coinbase, and previously co-founded Kippt, a bookmarking tool acquired by Coinbase.


In today’s episode, we discuss

  • Karri’s childhood love for computers that shaped his career
  • The lessons he learned from a failed first startup
  • Linear’s founding principles
  • The early validation strategies used to shape the product
  • Why Karri believes in small teams
  • And much more…


Referenced


Where to find Karri

Where to find Brett


Where to find First Round Capital

Timestamps

(1:37) Childhood roots in computers and design

(6:54) Founding Kippt and lessons from a failed bookmarking startup

(13:14) Lessons from a serial entrepreneur

(19:32) Why teams shouldn’t grow too quickly

(25: 03) Linear’s early beginnings

(36:55) The unexpected power of intuition

(42:41) Linear’s unusual approach to user growth

(47:29) What shaped Linear’s early product roadmap

(52:02) Startups shouldn’t try to boil the ocean

(57:30) The power of extreme focus

(59:18) Design “something for someone”

(1:04:29) Flexibility vs. simplicity

(1:17:27) Lead your team with strong principles

(1:24:45) Design founders vs. engineering founders

]]> 5584 How Wes Kao coaches founders to influence, lead, and get what they want | Wes Kao (Executive coach, co-founder of Maven) Wes Kao is an executive coach, advisor, and instructor, best known for her newsletter on high-impact communication, and for co-founding course platform Maven and the AltMBA with Seth Godin. Across her career, Wes has helped leaders communicate with clarity and conviction, whether it’s rallying a team, pitching investors, or influencing stakeholders. In this episode, Wes and Brett unpack how founders can be more persuasive, why playing to your strengths is critical, and how everyone can raise their own standards. --- In today’s episode, we discuss: Wes’ “personality-message fit” framework Why charisma is misunderstood How anyone can improve their communication What being told you need to “be more strategic” actually means and much more… --- Referenced: AltMBA: https://altmba.com/ Maven: https://maven.com/ Seth Godin: https://www.sethgodin.com/ Udemy: https://www.udemy.com/ --- Where to find Wes: LinkedIn: https://www.linkedin.com/in/weskao --- Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson --- Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast --- Timestamps: (1:54) Charisma is misunderstood (4:44) What underpins authenticity? (13:53) Clarity in communication (16:02) Start with your ideal outcome (22:05) The role of power dynamics (26:39) Should you work on weaknesses? (29:02) Effective self-reflection (32:13) Role-strength fit (37:39) What do you resent? (39:17) “Be more strategic” (45:20) Stack ranking (51:45) How AltMBA started (60:04) Defining your craft Thu, 22 May 2025 11:00:00 -0000 full First Round Wes Kao is an executive coach, advisor, and instructor, best known for her newsletter on high-impact communication, and for co-founding course platform Maven and the AltMBA with Seth Godin. Across her career, Wes has helped leaders communicate with clarity and conviction, whether it’s rallying a team, pitching investors, or influencing stakeholders. In this episode, Wes and Brett unpack how founders can be more persuasive, why playing to your strengths is critical, and how everyone can raise their own standards. --- In today’s episode, we discuss: Wes’ “personality-message fit” framework Why charisma is misunderstood How anyone can improve their communication What being told you need to “be more strategic” actually means and much more… --- Referenced: AltMBA: https://altmba.com/ Maven: https://maven.com/ Seth Godin: https://www.sethgodin.com/ Udemy: https://www.udemy.com/ --- Where to find Wes: LinkedIn: https://www.linkedin.com/in/weskao --- Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson --- Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast --- Timestamps: (1:54) Charisma is misunderstood (4:44) What underpins authenticity? (13:53) Clarity in communication (16:02) Start with your ideal outcome (22:05) The role of power dynamics (26:39) Should you work on weaknesses? (29:02) Effective self-reflection (32:13) Role-strength fit (37:39) What do you resent? (39:17) “Be more strategic” (45:20) Stack ranking (51:45) How AltMBA started (60:04) Defining your craft Wes Kao is an executive coach, advisor, and instructor, best known for her newsletter on high-impact communication, and for co-founding course platform Maven and the AltMBA with Seth Godin. Across her career, Wes has helped leaders communicate with clarity and conviction, whether it’s rallying a team, pitching investors, or influencing stakeholders.

In this episode, Wes and Brett unpack how founders can be more persuasive, why playing to your strengths is critical, and how everyone can raise their own standards.

---

In today’s episode, we discuss:

  • Wes’ “personality-message fit” framework
  • Why charisma is misunderstood
  • How anyone can improve their communication
  • What being told you need to “be more strategic” actually means
  • and much more…

---

Referenced:

---

Where to find Wes:

---

Where to find Brett:

---

Where to find First Round Capital:

---

Timestamps:

(1:54) Charisma is misunderstood

(4:44) What underpins authenticity?

(13:53) Clarity in communication

(16:02) Start with your ideal outcome

(22:05) The role of power dynamics

(26:39) Should you work on weaknesses?

(29:02) Effective self-reflection

(32:13) Role-strength fit

(37:39) What do you resent?

(39:17) “Be more strategic”

(45:20) Stack ranking

(51:45) How AltMBA started

(60:04) Defining your craft

]]> 4774 From reluctant founder to $2B valuation: The story of Persona | Rick Song (Co-founder and CEO) Rick Song is the co-founder and CEO of Persona, the identity verification platform used by some of the world’s largest companies. Before starting Persona, Rick worked on identity fraud and risk products at Square, which laid the groundwork for what would become Persona’s highly technical, horizontal platform. Since founding the company, Rick has scaled Persona into a category-defining leader, recently raising a $200M Series D at a $2B valuation. In today’s episode, we discuss: How Rick’s skepticism shaped Persona’s early strategy What it takes to scale a true platform company Successful execution in hypercompetitive markets What Rick’s learned from his co-founder, Charles Yeh and much more… Referenced: Accenture: accenture.com Anthropic: anthropic.com Braze: braze.com Bridgewater Associates: bridgewater.com Charles Yeh: linkedin.com/in/charlesyeh/ Christie Kim: linkedin.com/in/christiekimck/ Clay: clay.com Kareem Amin: linkedin.com/in/kareemamin/ MIT: mit.edu Newfront: newfront.com Palantir: palantir.com/ Persona: withpersona.com Rippling: rippling.com Scale AI: scale.com Snowflake: snowflake.com Square: squareup.com Y Combinator: ycombinator.com Zachary Van Zant: linkedin.com/in/zacharyv/ Where to find Rick: LinkedIn: https://www.linkedin.com/in/rick-song-25198b24/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: (0:05) Life before Persona (2:11) The push from Charles (3:09) Early reluctance and low expectations (9:50) Winning the first $50 customer (13:08)“Invalidating” Persona (16:43) How Persona found their edge (19:35) Transitioning from MVP to platform (24:18) Turning down a $5K deal on principle (26:47) Generalizing bespoke solutions (28:28) Finding product-market fit (33:51) Founder-led sales and consultative approach (39:30) Building a culture of reactivity (45:47) Landing the first enterprise customers (51:34) Silicon Valley’s obsession with frameworks (58:17) Developing first principles thinking (1:00:24) Stay competitor-informed Thu, 08 May 2025 17:12:00 -0000 full First Round Rick Song is the co-founder and CEO of Persona, the identity verification platform used by some of the world’s largest companies. Before starting Persona, Rick worked on identity fraud and risk products at Square, which laid the groundwork for what would become Persona’s highly technical, horizontal platform. Since founding the company, Rick has scaled Persona into a category-defining leader, recently raising a $200M Series D at a $2B valuation. In today’s episode, we discuss: How Rick’s skepticism shaped Persona’s early strategy What it takes to scale a true platform company Successful execution in hypercompetitive markets What Rick’s learned from his co-founder, Charles Yeh and much more… Referenced: Accenture: accenture.com Anthropic: anthropic.com Braze: braze.com Bridgewater Associates: bridgewater.com Charles Yeh: linkedin.com/in/charlesyeh/ Christie Kim: linkedin.com/in/christiekimck/ Clay: clay.com Kareem Amin: linkedin.com/in/kareemamin/ MIT: mit.edu Newfront: newfront.com Palantir: palantir.com/ Persona: withpersona.com Rippling: rippling.com Scale AI: scale.com Snowflake: snowflake.com Square: squareup.com Y Combinator: ycombinator.com Zachary Van Zant: linkedin.com/in/zacharyv/ Where to find Rick: LinkedIn: https://www.linkedin.com/in/rick-song-25198b24/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: (0:05) Life before Persona (2:11) The push from Charles (3:09) Early reluctance and low expectations (9:50) Winning the first $50 customer (13:08)“Invalidating” Persona (16:43) How Persona found their edge (19:35) Transitioning from MVP to platform (24:18) Turning down a $5K deal on principle (26:47) Generalizing bespoke solutions (28:28) Finding product-market fit (33:51) Founder-led sales and consultative approach (39:30) Building a culture of reactivity (45:47) Landing the first enterprise customers (51:34) Silicon Valley’s obsession with frameworks (58:17) Developing first principles thinking (1:00:24) Stay competitor-informed Rick Song is the co-founder and CEO of Persona, the identity verification platform used by some of the world’s largest companies. Before starting Persona, Rick worked on identity fraud and risk products at Square, which laid the groundwork for what would become Persona’s highly technical, horizontal platform. Since founding the company, Rick has scaled Persona into a category-defining leader, recently raising a $200M Series D at a $2B valuation.


In today’s episode, we discuss:

  • How Rick’s skepticism shaped Persona’s early strategy
  • What it takes to scale a true platform company
  • Successful execution in hypercompetitive markets
  • What Rick’s learned from his co-founder, Charles Yeh
  • and much more…


Referenced:


Where to find Rick:


Where to find Brett:


Where to find First Round Capital:


Timestamps:

(0:05) Life before Persona

(2:11) The push from Charles

(3:09) Early reluctance and low expectations

(9:50) Winning the first $50 customer

(13:08)“Invalidating” Persona

(16:43) How Persona found their edge

(19:35) Transitioning from MVP to platform

(24:18) Turning down a $5K deal on principle

(26:47) Generalizing bespoke solutions

(28:28) Finding product-market fit

(33:51) Founder-led sales and consultative approach

(39:30) Building a culture of reactivity

(45:47) Landing the first enterprise customers

(51:34) Silicon Valley’s obsession with frameworks

(58:17) Developing first principles thinking

(1:00:24) Stay competitor-informed

]]> 4499 How a weekend hack became a multimillion-dollar AI startup | Adit Abraham (Co-founder & CEO at Reducto) Adit Abraham is the co-founder and CEO of Reducto, which helps leading AI teams extract and structure data from complex documents and spreadsheets in their pipeline. Within 6 months of launching, Reducto went from 0→7 figures in ARR. Reducto has grown to process tens of millions of pages monthly for companies ranging from startups to Fortune 10 enterprises. They just announced a $24M Series A. Before Reducto, Adit was a Product Manager at Google, working on Ads and Search, and conducted machine learning research at MIT's Media Lab. --- In today’s episode, we discuss: How listening to customers revealed an opportunity to pivot The weekend project that became Reducto's breakthrough Landing a Fortune 10 customer A technical founder's guide to sales Key insights from Reducto's fundraising journey Advice for founders: “You’re going to fail” Much more --- Referenced: Anthropic: https://www.anthropic.com/ Chetan Puttagunta: https://www.linkedin.com/in/chetanputtagunta/ Diana Hu: https://www.linkedin.com/in/sdianahu/ Liz Wessel: https://www.linkedin.com/in/elizabethwessel/ Raunak Chowdhuri: https://www.linkedin.com/in/sauhaarda/ Reducto: https://reducto.ai/ Scale AI: https://scale.com/ Stripe: https://stripe.com/ Textract: https://aws.amazon.com/textract/ Y Combinator: https://www.ycombinator.com/ --- Where to find Adit: LinkedIn: https://www.linkedin.com/in/aditabraham/ --- Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson --- Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast --- Timestamps: (00:00) Hackathons, YC, and an unexpected pivot (05:23) The weekend project that became Reducto's breakthrough (09:11) How customer signal led to PDF processing (14:46) Landing a Fortune 10 customer (22:42) Building “transferable features” (25:58) How caring beats sales skills in startup growth (30:28) The strategy behind Reducto's horizontal expansion (36:18) Hire slow, go-to-market fast (41:45) A technical founder's guide to sales (43:45) “You’re going to fail” (46:27) Why startups win (48:30) Key insights from Reducto's fundraising journey (51:43) Less structure, more impact (55:00) How frustrations shaped Reducto’s culture (57:35) The question you should always ask in meetings Tue, 29 Apr 2025 16:00:00 -0000 full First Round Adit Abraham is the co-founder and CEO of Reducto, which helps leading AI teams extract and structure data from complex documents and spreadsheets in their pipeline. Within 6 months of launching, Reducto went from 0→7 figures in ARR. Reducto has grown to process tens of millions of pages monthly for companies ranging from startups to Fortune 10 enterprises. They just announced a $24M Series A. Before Reducto, Adit was a Product Manager at Google, working on Ads and Search, and conducted machine learning research at MIT's Media Lab. --- In today’s episode, we discuss: How listening to customers revealed an opportunity to pivot The weekend project that became Reducto's breakthrough Landing a Fortune 10 customer A technical founder's guide to sales Key insights from Reducto's fundraising journey Advice for founders: “You’re going to fail” Much more --- Referenced: Anthropic: https://www.anthropic.com/ Chetan Puttagunta: https://www.linkedin.com/in/chetanputtagunta/ Diana Hu: https://www.linkedin.com/in/sdianahu/ Liz Wessel: https://www.linkedin.com/in/elizabethwessel/ Raunak Chowdhuri: https://www.linkedin.com/in/sauhaarda/ Reducto: https://reducto.ai/ Scale AI: https://scale.com/ Stripe: https://stripe.com/ Textract: https://aws.amazon.com/textract/ Y Combinator: https://www.ycombinator.com/ --- Where to find Adit: LinkedIn: https://www.linkedin.com/in/aditabraham/ --- Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson --- Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast --- Timestamps: (00:00) Hackathons, YC, and an unexpected pivot (05:23) The weekend project that became Reducto's breakthrough (09:11) How customer signal led to PDF processing (14:46) Landing a Fortune 10 customer (22:42) Building “transferable features” (25:58) How caring beats sales skills in startup growth (30:28) The strategy behind Reducto's horizontal expansion (36:18) Hire slow, go-to-market fast (41:45) A technical founder's guide to sales (43:45) “You’re going to fail” (46:27) Why startups win (48:30) Key insights from Reducto's fundraising journey (51:43) Less structure, more impact (55:00) How frustrations shaped Reducto’s culture (57:35) The question you should always ask in meetings Adit Abraham is the co-founder and CEO of Reducto, which helps leading AI teams extract and structure data from complex documents and spreadsheets in their pipeline. Within 6 months of launching, Reducto went from 0→7 figures in ARR. Reducto has grown to process tens of millions of pages monthly for companies ranging from startups to Fortune 10 enterprises. They just announced a $24M Series A. Before Reducto, Adit was a Product Manager at Google, working on Ads and Search, and conducted machine learning research at MIT's Media Lab.

---

In today’s episode, we discuss:

  • How listening to customers revealed an opportunity to pivot
  • The weekend project that became Reducto's breakthrough
  • Landing a Fortune 10 customer
  • A technical founder's guide to sales
  • Key insights from Reducto's fundraising journey
  • Advice for founders: “You’re going to fail”
  • Much more

---

Referenced:

---

Where to find Adit:

---

Where to find Brett:

---

Where to find First Round Capital:

---

Timestamps:

(00:00) Hackathons, YC, and an unexpected pivot

(05:23) The weekend project that became Reducto's breakthrough

(09:11) How customer signal led to PDF processing

(14:46) Landing a Fortune 10 customer

(22:42) Building “transferable features”

(25:58) How caring beats sales skills in startup growth

(30:28) The strategy behind Reducto's horizontal expansion

(36:18) Hire slow, go-to-market fast

(41:45) A technical founder's guide to sales

(43:45) “You’re going to fail”

(46:27) Why startups win

(48:30) Key insights from Reducto's fundraising journey

(51:43) Less structure, more impact

(55:00) How frustrations shaped Reducto’s culture

(57:35) The question you should always ask in meetings

]]> 3602 1Password’s growth story | How they went from bootstrapped to $6B company | Jeff Shiner (CEO) Jeff Shiner is the CEO of 1Password, the access management company used by over 100,000 businesses and millions of individuals worldwide. He joined 1Password as CEO in 2012, when the team was just under 20 people. Under Jeff’s leadership, 1Password expanded into B2B, launched a SaaS platform, and scaled from a small family-run operation into a global company. In 2019, Jeff led 1Password through its first-ever funding round – a $200M Series A from Accel – to build out its go-to-market team and accelerate product development. Before joining 1Password, Jeff held senior roles at IBM and led teams through multiple acquisitions and integrations. --- In today’s episode, we discuss: Why bootstrapping isn’t always what it’s cracked up to be The switch from a consumer product to B2B Launching before billing — and why that worked When being “too secure” nearly killed the product Becoming CEO… without telling anyone Much more --- Referenced: 1Password: https://1password.com Accel: https://www.accel.com Arun Mathew: https://www.linkedin.com/in/arun-mathew-b7186412/ David Teare: https://www.linkedin.com/in/daveteare/ Floodgate: https://floodgate.com LastPass: https://www.lastpass.com Mike Maples: https://www.linkedin.com/in/maples/ Natalia Karimov: https://1password.com/company/meet-the-team/natalia-karimov Roustem Karimov: https://www.linkedin.com/in/roustem/?originalSubdomain=ca Sara Teare: https://1password.com/company/meet-the-team/sara-teare Shopify: https://www.shopify.com Tobi Lütke: https://www.linkedin.com/in/tobiaslutke/ --- Where to find Jeff: LinkedIn: https://www.linkedin.com/in/jshiner --- Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson --- Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast --- Timestamps: 0:03 – How Jeff got involved with 1Password 2:01 – How 1Password was initially set up 10:41 – The secret CEO 13:44 – What Jeff’s first six months encompassed 16:13 – The lightbulb moment that caused a pivot 17:50 – 1Password’s unusual company journey 22:08 – Creating an aligned product roadmap 29:19 – Retaining a customer-centric focus at scale 30:40 – Why 1Password’s first B2B product failed 39:43 – How Jeff thinks about competitors 46:44 – Building different go-to-market functions 52:45 – Staying bootstrapped for 15 years 57:17 – Jeff’s one regret 1:02:00 – 1Password’s most pivotal moments Thu, 24 Apr 2025 11:00:00 -0000 full First Round Jeff Shiner is the CEO of 1Password, the access management company used by over 100,000 businesses and millions of individuals worldwide. He joined 1Password as CEO in 2012, when the team was just under 20 people. Under Jeff’s leadership, 1Password expanded into B2B, launched a SaaS platform, and scaled from a small family-run operation into a global company. In 2019, Jeff led 1Password through its first-ever funding round – a $200M Series A from Accel – to build out its go-to-market team and accelerate product development. Before joining 1Password, Jeff held senior roles at IBM and led teams through multiple acquisitions and integrations. --- In today’s episode, we discuss: Why bootstrapping isn’t always what it’s cracked up to be The switch from a consumer product to B2B Launching before billing — and why that worked When being “too secure” nearly killed the product Becoming CEO… without telling anyone Much more --- Referenced: 1Password: https://1password.com Accel: https://www.accel.com Arun Mathew: https://www.linkedin.com/in/arun-mathew-b7186412/ David Teare: https://www.linkedin.com/in/daveteare/ Floodgate: https://floodgate.com LastPass: https://www.lastpass.com Mike Maples: https://www.linkedin.com/in/maples/ Natalia Karimov: https://1password.com/company/meet-the-team/natalia-karimov Roustem Karimov: https://www.linkedin.com/in/roustem/?originalSubdomain=ca Sara Teare: https://1password.com/company/meet-the-team/sara-teare Shopify: https://www.shopify.com Tobi Lütke: https://www.linkedin.com/in/tobiaslutke/ --- Where to find Jeff: LinkedIn: https://www.linkedin.com/in/jshiner --- Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson --- Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast --- Timestamps: 0:03 – How Jeff got involved with 1Password 2:01 – How 1Password was initially set up 10:41 – The secret CEO 13:44 – What Jeff’s first six months encompassed 16:13 – The lightbulb moment that caused a pivot 17:50 – 1Password’s unusual company journey 22:08 – Creating an aligned product roadmap 29:19 – Retaining a customer-centric focus at scale 30:40 – Why 1Password’s first B2B product failed 39:43 – How Jeff thinks about competitors 46:44 – Building different go-to-market functions 52:45 – Staying bootstrapped for 15 years 57:17 – Jeff’s one regret 1:02:00 – 1Password’s most pivotal moments Jeff Shiner is the CEO of 1Password, the access management company used by over 100,000 businesses and millions of individuals worldwide. He joined 1Password as CEO in 2012, when the team was just under 20 people. Under Jeff’s leadership, 1Password expanded into B2B, launched a SaaS platform, and scaled from a small family-run operation into a global company. In 2019, Jeff led 1Password through its first-ever funding round – a $200M Series A from Accel – to build out its go-to-market team and accelerate product development. Before joining 1Password, Jeff held senior roles at IBM and led teams through multiple acquisitions and integrations.


---


In today’s episode, we discuss:

  • Why bootstrapping isn’t always what it’s cracked up to be
  • The switch from a consumer product to B2B
  • Launching before billing — and why that worked
  • When being “too secure” nearly killed the product
  • Becoming CEO… without telling anyone
  • Much more


---


Referenced:

  • 1Password: https://1password.com
  • Accel: https://www.accel.com
  • Arun Mathew: https://www.linkedin.com/in/arun-mathew-b7186412/
  • David Teare: https://www.linkedin.com/in/daveteare/
  • Floodgate: https://floodgate.com
  • LastPass: https://www.lastpass.com
  • Mike Maples: https://www.linkedin.com/in/maples/
  • Natalia Karimov: https://1password.com/company/meet-the-team/natalia-karimov
  • Roustem Karimov: https://www.linkedin.com/in/roustem/?originalSubdomain=ca
  • Sara Teare: https://1password.com/company/meet-the-team/sara-teare
  • Shopify: https://www.shopify.com
  • Tobi Lütke: https://www.linkedin.com/in/tobiaslutke/


---


Where to find Jeff:

  • LinkedIn: https://www.linkedin.com/in/jshiner


---


Where to find Brett:

  • LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
  • Twitter/X: https://twitter.com/brettberson


---


Where to find First Round Capital:

  • Website: https://firstround.com/
  • First Round Review: https://review.firstround.com/
  • Twitter/X: https://twitter.com/firstround
  • YouTube: https://www.youtube.com/@FirstRoundCapital
  • This podcast on all platforms: https://review.firstround.com/podcast


---


Timestamps:

0:03 – How Jeff got involved with 1Password

2:01 – How 1Password was initially set up

10:41 – The secret CEO

13:44 – What Jeff’s first six months encompassed

16:13 – The lightbulb moment that caused a pivot

17:50 – 1Password’s unusual company journey

22:08 – Creating an aligned product roadmap

29:19 – Retaining a customer-centric focus at scale

30:40 – Why 1Password’s first B2B product failed

39:43 – How Jeff thinks about competitors

46:44 – Building different go-to-market functions

52:45 – Staying bootstrapped for 15 years

57:17 – Jeff’s one regret

1:02:00 – 1Password’s most pivotal moments

]]> 4088 no Scrappy tactics and a huge post-COVID pivot | Owner’s unconventional journey to product-market fit | Adam Guild (Co-founder and CEO of Owner) Adam Guild is the co-founder and CEO at Owner, an online food ordering system for independent restaurants. Within a year, Owner went from being about to run out of money to having hundreds of customers. Last year, they raised a $33M Series B. Adam’s entrepreneurial journey began as a teenager when he built a successful Minecraft server, which led him to drop out of high school to become a founder. His passion for helping small businesses was sparked by his mom’s struggles running a dog grooming shop, which led him to launch the early iteration of Owner. -- In today’s episode, we discuss: How working with a small business kickstarted Owner Adam’s unusual outbound strategy Why the pandemic accelerated Owner’s success How Owner’s pivot led to “hyperbolic” product-market fit The two qualities Adam looks for in new hires -- Referenced: Alex Bard: https://www.linkedin.com/in/alexbard/ Dean Bloembergen: https://www.linkedin.com/in/deanbloembergen/ Guisados: https://www.guisados.la/ HubSpot: https://www.hubspot.com/ Jack Altman: https://www.linkedin.com/in/jackealtman/ Kimbal Musk: https://www.linkedin.com/in/kimbalmusk/ Modern Restaurant Management: https://modernrestaurantmanagement.com/ Naval Ravikant: https://www.linkedin.com/in/navalr/ Neil Patel: https://www.linkedin.com/in/neilkpatel/ Peter Thiel: https://www.linkedin.com/in/peterthiel/ P.F. Chang's: https://www.pfchangs.com/ Sean Rad: https://www.linkedin.com/in/seanrad/ Thiel Fellowship: https://thielfellowship.org/ Tim Ferriss: https://www.linkedin.com/in/timferriss/ Y Combinator: https://www.ycombinator.com/ -- Where to find Adam: LinkedIn: https://www.linkedin.com/in/adamharrisonguild/ -- Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast -- Timestamps: (00:00) Intro (01:29) Adam’s first business (04:15) The transition from Minecraft to Owner (05:58) The dark side of the gaming industry (14:20 Adam’s scrappy strategy to landing his first customers (16:52) The COVID pivot (21:31) The quest to find product-market fit (30:53) What actually worked to get new customers (36:03) Inside Owner’s explosive growth (46:41) How Owner secured its crucial first round of funding (53:34) The bet on going multi-product (64:28) What Adam wishes he knew at 17 (76:22) Sales-led vs. product-led growth Thu, 27 Mar 2025 14:06:00 -0000 full First Round Adam Guild is the co-founder and CEO at Owner, an online food ordering system for independent restaurants. Within a year, Owner went from being about to run out of money to having hundreds of customers. Last year, they raised a $33M Series B. Adam’s entrepreneurial journey began as a teenager when he built a successful Minecraft server, which led him to drop out of high school to become a founder. His passion for helping small businesses was sparked by his mom’s struggles running a dog grooming shop, which led him to launch the early iteration of Owner. -- In today’s episode, we discuss: How working with a small business kickstarted Owner Adam’s unusual outbound strategy Why the pandemic accelerated Owner’s success How Owner’s pivot led to “hyperbolic” product-market fit The two qualities Adam looks for in new hires -- Referenced: Alex Bard: https://www.linkedin.com/in/alexbard/ Dean Bloembergen: https://www.linkedin.com/in/deanbloembergen/ Guisados: https://www.guisados.la/ HubSpot: https://www.hubspot.com/ Jack Altman: https://www.linkedin.com/in/jackealtman/ Kimbal Musk: https://www.linkedin.com/in/kimbalmusk/ Modern Restaurant Management: https://modernrestaurantmanagement.com/ Naval Ravikant: https://www.linkedin.com/in/navalr/ Neil Patel: https://www.linkedin.com/in/neilkpatel/ Peter Thiel: https://www.linkedin.com/in/peterthiel/ P.F. Chang's: https://www.pfchangs.com/ Sean Rad: https://www.linkedin.com/in/seanrad/ Thiel Fellowship: https://thielfellowship.org/ Tim Ferriss: https://www.linkedin.com/in/timferriss/ Y Combinator: https://www.ycombinator.com/ -- Where to find Adam: LinkedIn: https://www.linkedin.com/in/adamharrisonguild/ -- Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast -- Timestamps: (00:00) Intro (01:29) Adam’s first business (04:15) The transition from Minecraft to Owner (05:58) The dark side of the gaming industry (14:20 Adam’s scrappy strategy to landing his first customers (16:52) The COVID pivot (21:31) The quest to find product-market fit (30:53) What actually worked to get new customers (36:03) Inside Owner’s explosive growth (46:41) How Owner secured its crucial first round of funding (53:34) The bet on going multi-product (64:28) What Adam wishes he knew at 17 (76:22) Sales-led vs. product-led growth Adam Guild is the co-founder and CEO at Owner, an online food ordering system for independent restaurants. Within a year, Owner went from being about to run out of money to having hundreds of customers. Last year, they raised a $33M Series B.

Adam’s entrepreneurial journey began as a teenager when he built a successful Minecraft server, which led him to drop out of high school to become a founder. His passion for helping small businesses was sparked by his mom’s struggles running a dog grooming shop, which led him to launch the early iteration of Owner.

--

In today’s episode, we discuss:

  • How working with a small business kickstarted Owner
  • Adam’s unusual outbound strategy
  • Why the pandemic accelerated Owner’s success
  • How Owner’s pivot led to “hyperbolic” product-market fit
  • The two qualities Adam looks for in new hires

--

Referenced:

--

Where to find Adam:

--

Where to find Brett:


Where to find First Round Capital:

--

Timestamps:

(00:00) Intro

(01:29) Adam’s first business

(04:15) The transition from Minecraft to Owner

(05:58) The dark side of the gaming industry

(14:20 Adam’s scrappy strategy to landing his first customers

(16:52) The COVID pivot

(21:31) The quest to find product-market fit

(30:53) What actually worked to get new customers

(36:03) Inside Owner’s explosive growth

(46:41) How Owner secured its crucial first round of funding

(53:34) The bet on going multi-product

(64:28) What Adam wishes he knew at 17

(76:22) Sales-led vs. product-led growth

]]> 5009 What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Head of Global Product at Stripe) Eeke de Milliano is the Head of Global Product at Stripe, helping drive innovation and success in the company's product line. Before this role, she was Head of Product at Retool and co-founded Constellate. Eeke previously spent 6 years as Product Lead at Stripe, working with the company during their hyper-growth era. – In today’s episode, we discuss: Eeke’s wealth of experience as an executive leader The challenges companies face when hiring new executives Common hiring red flags and pitfalls Practical advice for measuring success Why learning your strengths is an underrated piece of the process – Referenced: ASML: https://www.asml.com/en Claire Hughes Johnson: https://www.linkedin.com/in/claire-hughes-johnson-7058/ Constellate: https://constellate.team/ John Collison: https://www.linkedin.com/in/johnbcollison/ Mike Maples Jr.: https://www.linkedin.com/in/maples/ Patrick Collison: https://www.linkedin.com/in/patrickcollison/ Retool: https://retool.com/ Stripe: https://stripe.com/ Will Gaybrik: https://www.linkedin.com/in/william-gaybrick-5730347/ – Where to find Eeke: LinkedIn: https://www.linkedin.com/in/eeke-de-milliano-3b05a629/ – Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Should you ‘buy or build’ a leader (03:45) Why do executive hires fail so often? (09:35) Why the stakes are so high for leadership hires (12:26) The hardest document Eeke ever wrote (14:06) Two red flags in a new hire (17:27) An example of an outstanding leader (21:40) What creates dysfunctional exec relationships (22:38) The three steps towards hiring successful leaders (30:30) What you should know about outside hires (33:12) Eeke’s advice for easing leadership transitions (42:06) How to notice success patterns (47:21) Why high-functioning executive teams are like parents (52:02) The most surprising lesson from Eeke’s first stint at Stripe (55:11) The leadership data Eeke wishes we had Thu, 06 Mar 2025 12:00:00 -0000 What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Head of Global Product at Stripe) full First Round Eeke de Milliano is the Head of Global Product at Stripe, helping drive innovation and success in the company's product line. Before this role, she was Head of Product at Retool and co-founded Constellate. Eeke previously spent 6 years as Product Lead at Stripe, working with the company during their hyper-growth era. Eeke de Milliano is the Head of Global Product at Stripe, helping drive innovation and success in the company's product line. Before this role, she was Head of Product at Retool and co-founded Constellate. Eeke previously spent 6 years as Product Lead at Stripe, working with the company during their hyper-growth era. – In today’s episode, we discuss: Eeke’s wealth of experience as an executive leader The challenges companies face when hiring new executives Common hiring red flags and pitfalls Practical advice for measuring success Why learning your strengths is an underrated piece of the process – Referenced: ASML: https://www.asml.com/en Claire Hughes Johnson: https://www.linkedin.com/in/claire-hughes-johnson-7058/ Constellate: https://constellate.team/ John Collison: https://www.linkedin.com/in/johnbcollison/ Mike Maples Jr.: https://www.linkedin.com/in/maples/ Patrick Collison: https://www.linkedin.com/in/patrickcollison/ Retool: https://retool.com/ Stripe: https://stripe.com/ Will Gaybrik: https://www.linkedin.com/in/william-gaybrick-5730347/ – Where to find Eeke: LinkedIn: https://www.linkedin.com/in/eeke-de-milliano-3b05a629/ – Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Should you ‘buy or build’ a leader (03:45) Why do executive hires fail so often? (09:35) Why the stakes are so high for leadership hires (12:26) The hardest document Eeke ever wrote (14:06) Two red flags in a new hire (17:27) An example of an outstanding leader (21:40) What creates dysfunctional exec relationships (22:38) The three steps towards hiring successful leaders (30:30) What you should know about outside hires (33:12) Eeke’s advice for easing leadership transitions (42:06) How to notice success patterns (47:21) Why high-functioning executive teams are like parents (52:02) The most surprising lesson from Eeke’s first stint at Stripe (55:11) The leadership data Eeke wishes we had Eeke de Milliano is the Head of Global Product at Stripe, helping drive innovation and success in the company's product line. Before this role, she was Head of Product at Retool and co-founded Constellate. Eeke previously spent 6 years as Product Lead at Stripe, working with the company during their hyper-growth era.

–

In today’s episode, we discuss:

  • Eeke’s wealth of experience as an executive leader
  • The challenges companies face when hiring new executives
  • Common hiring red flags and pitfalls
  • Practical advice for measuring success
  • Why learning your strengths is an underrated piece of the process

–

Referenced:

–

Where to find Eeke:

–

Where to find Brett:

–

Where to find First Round Capital:

–

Timestamps:

(00:00) Should you ‘buy or build’ a leader

(03:45) Why do executive hires fail so often?

(09:35) Why the stakes are so high for leadership hires

(12:26) The hardest document Eeke ever wrote

(14:06) Two red flags in a new hire

(17:27) An example of an outstanding leader

(21:40) What creates dysfunctional exec relationships

(22:38) The three steps towards hiring successful leaders

(30:30) What you should know about outside hires

(33:12) Eeke’s advice for easing leadership transitions

(42:06) How to notice success patterns

(47:21) Why high-functioning executive teams are like parents

(52:02) The most surprising lesson from Eeke’s first stint at Stripe

(55:11) The leadership data Eeke wishes we had

]]> 3599 Inside Guideline's mission to modernize 401(k)s | Building from first principles, finding strategic edges, and rewiring retirement | Kevin Busque (Co-founder and CEO) Kevin Busque is the co-founder and CEO of Guideline, a 401(k) management company revolutionizing the retirement space for small and medium-sized businesses. Prior to Guideline, Kevin co-founded Taskrabbit, where he encountered firsthand the complexity and low participation rates of traditional 401(k) plans—largely due to confusing fee structures. After launching Guideline to address those problems head-on, the company has seen remarkable growth, hitting $120 million in ARR by June 2024. In this conversation, Kevin shares pivotal moments that shaped Guideline’s trajectory, including a strategic partnership with Gusto. He also explains how his “Do the hard thing first” mindset helped the team build an industry-leading platform and disrupt an entrenched market. – Referenced: ADP: https://www.adp.com/ Aydin Senkut: https://www.linkedin.com/in/aydins/ CalSavers: https://www.calsavers.com/ DoorDash: https://www.doordash.com/ Fidelity: https://www.fidelity.com/ Guideline: https://www.guideline.com/ Gusto: https://gusto.com/ Intuit: https://www.intuit.com/ Jeremy Caballero: https://www.linkedin.com/in/jeremycaballero/ John Zimmer: https://www.linkedin.com/in/johnzimmer11/ Josh Reeves: https://www.linkedin.com/in/joshuareeves/ Mike Nelson: https://www.linkedin.com/in/mnelsonio/ Leah Solivan: https://www.linkedin.com/in/leahsolivan/ Paychex: https://www.paychex.com/ Plaid: https://plaid.com/ Taskrabbit: https://www.taskrabbit.com/ Tomer London: https://www.linkedin.com/in/tomerlondon/ – Where to find Kevin: LinkedIn: https://www.linkedin.com/in/kevinbusque/ – Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Teaser: “I don’t believe in stealth mode” (02:51) Inspiration behind Guideline (07:56) Lessons from a year’s research before Guideline (10:44) Identifying market pull for Guideline (14:28) What Kevin learnt before shipping their first product (19:10) How Guideline set their fees up (27:51) The surprising range of Guideline’s early customers (31:48) Kevin’s insights from the Gusto integration (39:48) Guideline’s first year (44:44) Working with Plaid as Guideline’s first customer (53:28) Guideline’s auto-enrollment feature (57:53) Lucky 8: Kevin’s unexpected pricing strategy (62:04) Franchise opportunities (64:49) Kevin’s reflections on Taskrabbit (71:36) Will Guideline ever go multi-product? (72:37) Kevin’s take on product-market fit (73:30) Guideline’s compounding advantage (78:51) The challenges faced by introverted leaders Thu, 20 Feb 2025 12:00:00 -0000 Inside Guideline's mission to modernize 401(k)s | Building from first principles, finding strategic edges, and rewiring retirement | Kevin Busque (Co-founder and CEO) full First Round Kevin Busque is the co-founder and CEO of Guideline, a 401(k) management company revolutionizing the retirement space for small and medium-sized businesses. Prior to Guideline, Kevin co-founded Taskrabbit, where he encountered firsthand the complexity and low participation rates of traditional 401(k) plans—largely due to confusing fee structures. Kevin Busque is the co-founder and CEO of Guideline, a 401(k) management company revolutionizing the retirement space for small and medium-sized businesses. Prior to Guideline, Kevin co-founded Taskrabbit, where he encountered firsthand the complexity and low participation rates of traditional 401(k) plans—largely due to confusing fee structures. After launching Guideline to address those problems head-on, the company has seen remarkable growth, hitting $120 million in ARR by June 2024. In this conversation, Kevin shares pivotal moments that shaped Guideline’s trajectory, including a strategic partnership with Gusto. He also explains how his “Do the hard thing first” mindset helped the team build an industry-leading platform and disrupt an entrenched market. – Referenced: ADP: https://www.adp.com/ Aydin Senkut: https://www.linkedin.com/in/aydins/ CalSavers: https://www.calsavers.com/ DoorDash: https://www.doordash.com/ Fidelity: https://www.fidelity.com/ Guideline: https://www.guideline.com/ Gusto: https://gusto.com/ Intuit: https://www.intuit.com/ Jeremy Caballero: https://www.linkedin.com/in/jeremycaballero/ John Zimmer: https://www.linkedin.com/in/johnzimmer11/ Josh Reeves: https://www.linkedin.com/in/joshuareeves/ Mike Nelson: https://www.linkedin.com/in/mnelsonio/ Leah Solivan: https://www.linkedin.com/in/leahsolivan/ Paychex: https://www.paychex.com/ Plaid: https://plaid.com/ Taskrabbit: https://www.taskrabbit.com/ Tomer London: https://www.linkedin.com/in/tomerlondon/ – Where to find Kevin: LinkedIn: https://www.linkedin.com/in/kevinbusque/ – Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Teaser: “I don’t believe in stealth mode” (02:51) Inspiration behind Guideline (07:56) Lessons from a year’s research before Guideline (10:44) Identifying market pull for Guideline (14:28) What Kevin learnt before shipping their first product (19:10) How Guideline set their fees up (27:51) The surprising range of Guideline’s early customers (31:48) Kevin’s insights from the Gusto integration (39:48) Guideline’s first year (44:44) Working with Plaid as Guideline’s first customer (53:28) Guideline’s auto-enrollment feature (57:53) Lucky 8: Kevin’s unexpected pricing strategy (62:04) Franchise opportunities (64:49) Kevin’s reflections on Taskrabbit (71:36) Will Guideline ever go multi-product? (72:37) Kevin’s take on product-market fit (73:30) Guideline’s compounding advantage (78:51) The challenges faced by introverted leaders Kevin Busque is the co-founder and CEO of Guideline, a 401(k) management company revolutionizing the retirement space for small and medium-sized businesses. Prior to Guideline, Kevin co-founded Taskrabbit, where he encountered firsthand the complexity and low participation rates of traditional 401(k) plans—largely due to confusing fee structures.

After launching Guideline to address those problems head-on, the company has seen remarkable growth, hitting $120 million in ARR by June 2024. In this conversation, Kevin shares pivotal moments that shaped Guideline’s trajectory, including a strategic partnership with Gusto. He also explains how his “Do the hard thing first” mindset helped the team build an industry-leading platform and disrupt an entrenched market.

–

Referenced:

–

Where to find Kevin:

–

Where to find Brett:

–

Where to find First Round Capital:

–

Timestamps:

(00:00) Teaser: “I don’t believe in stealth mode”

(02:51) Inspiration behind Guideline

(07:56) Lessons from a year’s research before Guideline

(10:44) Identifying market pull for Guideline

(14:28) What Kevin learnt before shipping their first product

(19:10) How Guideline set their fees up

(27:51) The surprising range of Guideline’s early customers

(31:48) Kevin’s insights from the Gusto integration

(39:48) Guideline’s first year

(44:44) Working with Plaid as Guideline’s first customer

(53:28) Guideline’s auto-enrollment feature

(57:53) Lucky 8: Kevin’s unexpected pricing strategy

(62:04) Franchise opportunities

(64:49) Kevin’s reflections on Taskrabbit

(71:36) Will Guideline ever go multi-product?

(72:37) Kevin’s take on product-market fit

(73:30) Guideline’s compounding advantage

(78:51) The challenges faced by introverted leaders

]]> 5089 Inside Braze’s blitz to $500M in CARR | Building broad, going global, and outfoxing the competition | Bill Magnuson (Co-founder & CEO) and Kevin Wang (CPO) Bill Magnuson is the co-founder and CEO at Braze, along with Kevin Wang, who joined as employee #8 and serves as the CPO. The two MIT graduates have built Braze into a publicly listed customer engagement platform with a $4.4B market cap. In 2023, Braze surpassed $500M in CARR, and serves over 2,200 customers worldwide. Before Braze, Bill spent time at Bridgewater Associates. Kevin’s academic background is in brain & cognitive sciences, and prior to joining Braze he worked at Accenture and Brewgene. – In today’s episode, we discuss: The Braze founders’ early insights into the mobile revolution How a TechCrunch Hackathon sparked Braze's creation The journey from 1,000 beta signups to 2,200+ paying customers Breaking traditional lean startup rules Navigating early fundraising challenges Finding product market fit by “fishing in every pond” Approaching competition strategically like a boxer Much more – Referenced: Accenture: https://www.accenture.com/ Appboy: https://www.braze.com/resources/articles/appboy-social-network-for-mobile-apps Bipul Sinha: https://www.linkedin.com/in/bipulsinha/ Braze: https://www.braze.com/ Bridgewater Associates: https://www.bridgewater.com/ Jon Hyman: https://www.linkedin.com/in/jon-hyman/ Mark Ghermezian: https://x.com/markgher MIT: https://www.mit.edu/ Rubrik: https://www.rubrik.com/ WeWork: https://www.wework.com/ – Where to find Bill: LinkedIn: https://www.linkedin.com/in/billmagnuson/ Twitter/X: https://x.com/billmag – Where to find Kevin: LinkedIn: https://www.linkedin.com/in/kevin-wang-96131916/ – Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Teaser: Finding “terminal value” product market fit (00:24) Introduction (02:34) Bill's insights into the mobile revolution (04:43) Lessons from Bridgewater Associates (09:12) First principles thinking in action at Braze (14:14) Meeting co-founders at an NYC Hackathon (24:35) Braze’s scrappy scaling (33:37) Early product development (39:37) From 1,000 beta signups to 2,200+ paying customers (43:51) Braze’s fundraising struggles (47:01) Breaking the rules of a lean startup (53:02) Riding the mobile wave to success (60:02) Building a global customer base (64:04) The never-ending quest for PMF (70:29) 3 things every founder needs to know (73:56) Navigating competition like a boxer (79:03) When scale helps or hurts (80:32) 1 thing they’ve learned from each other Thu, 06 Feb 2025 12:00:00 -0000 Inside Braze’s blitz to $500M in CARR | Building broad, going global, and outfoxing the competition | Bill Magnuson (Co-founder & CEO) and Kevin Wang (CPO) full First Round Bill Magnuson is the co-founder and CEO at Braze, along with Kevin Wang, who joined as employee #8 and serves as the CPO. The two MIT graduates have built Braze into a publicly listed customer engagement platform with a $4.4B market cap. In 2023, Braze surpassed $500M in CARR, and serves over 2,200 customers worldwide. Before Braze, Bill spent time at Bridgewater Associates. Kevin’s academic background is in brain & cognitive sciences, and prior to joining Braze he worked at Accenture and Brewgene. Bill Magnuson is the co-founder and CEO at Braze, along with Kevin Wang, who joined as employee #8 and serves as the CPO. The two MIT graduates have built Braze into a publicly listed customer engagement platform with a $4.4B market cap. In 2023, Braze surpassed $500M in CARR, and serves over 2,200 customers worldwide. Before Braze, Bill spent time at Bridgewater Associates. Kevin’s academic background is in brain & cognitive sciences, and prior to joining Braze he worked at Accenture and Brewgene. – In today’s episode, we discuss: The Braze founders’ early insights into the mobile revolution How a TechCrunch Hackathon sparked Braze's creation The journey from 1,000 beta signups to 2,200+ paying customers Breaking traditional lean startup rules Navigating early fundraising challenges Finding product market fit by “fishing in every pond” Approaching competition strategically like a boxer Much more – Referenced: Accenture: https://www.accenture.com/ Appboy: https://www.braze.com/resources/articles/appboy-social-network-for-mobile-apps Bipul Sinha: https://www.linkedin.com/in/bipulsinha/ Braze: https://www.braze.com/ Bridgewater Associates: https://www.bridgewater.com/ Jon Hyman: https://www.linkedin.com/in/jon-hyman/ Mark Ghermezian: https://x.com/markgher MIT: https://www.mit.edu/ Rubrik: https://www.rubrik.com/ WeWork: https://www.wework.com/ – Where to find Bill: LinkedIn: https://www.linkedin.com/in/billmagnuson/ Twitter/X: https://x.com/billmag – Where to find Kevin: LinkedIn: https://www.linkedin.com/in/kevin-wang-96131916/ – Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Teaser: Finding “terminal value” product market fit (00:24) Introduction (02:34) Bill's insights into the mobile revolution (04:43) Lessons from Bridgewater Associates (09:12) First principles thinking in action at Braze (14:14) Meeting co-founders at an NYC Hackathon (24:35) Braze’s scrappy scaling (33:37) Early product development (39:37) From 1,000 beta signups to 2,200+ paying customers (43:51) Braze’s fundraising struggles (47:01) Breaking the rules of a lean startup (53:02) Riding the mobile wave to success (60:02) Building a global customer base (64:04) The never-ending quest for PMF (70:29) 3 things every founder needs to know (73:56) Navigating competition like a boxer (79:03) When scale helps or hurts (80:32) 1 thing they’ve learned from each other Bill Magnuson is the co-founder and CEO at Braze, along with Kevin Wang, who joined as employee #8 and serves as the CPO. The two MIT graduates have built Braze into a publicly listed customer engagement platform with a $4.4B market cap. In 2023, Braze surpassed $500M in CARR, and serves over 2,200 customers worldwide. Before Braze, Bill spent time at Bridgewater Associates. Kevin’s academic background is in brain & cognitive sciences, and prior to joining Braze he worked at Accenture and Brewgene.

–

In today’s episode, we discuss:

  • The Braze founders’ early insights into the mobile revolution
  • How a TechCrunch Hackathon sparked Braze's creation
  • The journey from 1,000 beta signups to 2,200+ paying customers
  • Breaking traditional lean startup rules
  • Navigating early fundraising challenges
  • Finding product market fit by “fishing in every pond”
  • Approaching competition strategically like a boxer
  • Much more

–

Referenced:

–

Where to find Bill:

–

Where to find Kevin:

–

Where to find Brett:

–

Where to find First Round Capital:

–

Timestamps:

(00:00) Teaser: Finding “terminal value” product market fit

(00:24) Introduction

(02:34) Bill's insights into the mobile revolution

(04:43) Lessons from Bridgewater Associates

(09:12) First principles thinking in action at Braze

(14:14) Meeting co-founders at an NYC Hackathon

(24:35) Braze’s scrappy scaling

(33:37) Early product development

(39:37) From 1,000 beta signups to 2,200+ paying customers

(43:51) Braze’s fundraising struggles

(47:01) Breaking the rules of a lean startup

(53:02) Riding the mobile wave to success

(60:02) Building a global customer base

(64:04) The never-ending quest for PMF

(70:29) 3 things every founder needs to know

(73:56) Navigating competition like a boxer

(79:03) When scale helps or hurts

(80:32) 1 thing they’ve learned from each other

]]> 4987 Inside Clay's unconventional path to $1.25B: Rethinking GTM, pricing, and enterprise sales | Varun Anand (Co-founder and Head of Operations) Varun Anand is the co-founder and Head of Operations at Clay, a GTM development environment that combines data and AI to help over 5000 companies power everything from CRM enrichment to highly targeted outreach campaigns. Clay recently announced their Series B expansion, raising $40M at a $1.25B valuation. Before Clay, Varun was the Director of Operations at Newfront and the Head of Expansion at Candid. Varun also spent four years working on Hillary Clinton’s presidential campaign. – In today’s episode, we discuss: Clay’s unconventional GTM machine 3 changes that unlocked Clay's upmarket motion Layering enterprise customers on top of PLG Scrappy sales tactics: WhatsApp groups, Reddit threads, and reverse demos Thinking long-term about brand and content Building an elite team of people who are “technical enough” Clay’s contrarian take on compensation Much more – Referenced: Anthropic: https://www.anthropic.com/ Clay: https://www.clay.com/ Clay’s Series B expansion: https://www.clay.com/blog/series-b-expansion Eric Nowoslawski: https://www.linkedin.com/in/outboundphd/ Figma: https://www.figma.com/ Jesse Ouellette: https://www.linkedin.com/in/jesseoue/ Kareem Amin: https://www.linkedin.com/in/kareemamin/ Nick Merrill: https://www.linkedin.com/in/nick-merrill-64562310/ Notion: https://www.notion.com/ Oyster: https://www.oysterhr.com/ Pave: https://www.pave.com/ Rippling: https://www.rippling.com/ Snowflake: https://www.snowflake.com/ Verkada: https://www.verkada.com/ Webflow: https://webflow.com/ Yash Tekriwal: https://www.linkedin.com/in/yashtekriwal/ – Where to find Varun: LinkedIn: https://www.linkedin.com/in/vaanand/ Twitter/X: https://x.com/vxanand – Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Teaser + Introduction (03:13) Turning traditional GTM on its head (05:37) How Clay hustled for its first customers: Reddit threads & WhatsApp groups (08:53) Unpacking Clay's credit-based pricing (14:29) Building Clay's self-serve engine (16:54) Why Clay rejected the usage-based model (19:04) Clay’s big bet on content (23:59) How "reverse demos" win enterprise deals (27:49) 3 changes that unlocked Clay's upmarket motion (36:59) How to build trust with enterprise buyers (38:49) Applying the land and expand model (40:40) Hiring people who are “technical enough” (46:33) Inside Clay’s hands-on interviewing process (48:15) Why Clay invested in brand from day-one (50:21) Clay’s contrarian take on compensation (58:35) The person who shaped Varun’s career Thu, 23 Jan 2025 12:00:00 -0000 Inside Clay's unconventional path to $1.25B: Rethinking GTM, pricing, and enterprise sales | Varun Anand (Co-founder and Head of Operations) full First Round Varun Anand is the co-founder and Head of Operations at Clay, a lead-generation software that combines data and AI to help over 5000 companies reach their best-fit customers. Clay recently announced their Series B expansion, raising $40M at a $1.2B valuation. Before Clay, Varun was the Director of Operations at Newfront and the Head of Expansion at Candid. Varun also spent four years working on Hillary Clinton’s Presidential Campaign. Varun Anand is the co-founder and Head of Operations at Clay, a GTM development environment that combines data and AI to help over 5000 companies power everything from CRM enrichment to highly targeted outreach campaigns. Clay recently announced their Series B expansion, raising $40M at a $1.25B valuation. Before Clay, Varun was the Director of Operations at Newfront and the Head of Expansion at Candid. Varun also spent four years working on Hillary Clinton’s presidential campaign. – In today’s episode, we discuss: Clay’s unconventional GTM machine 3 changes that unlocked Clay's upmarket motion Layering enterprise customers on top of PLG Scrappy sales tactics: WhatsApp groups, Reddit threads, and reverse demos Thinking long-term about brand and content Building an elite team of people who are “technical enough” Clay’s contrarian take on compensation Much more – Referenced: Anthropic: https://www.anthropic.com/ Clay: https://www.clay.com/ Clay’s Series B expansion: https://www.clay.com/blog/series-b-expansion Eric Nowoslawski: https://www.linkedin.com/in/outboundphd/ Figma: https://www.figma.com/ Jesse Ouellette: https://www.linkedin.com/in/jesseoue/ Kareem Amin: https://www.linkedin.com/in/kareemamin/ Nick Merrill: https://www.linkedin.com/in/nick-merrill-64562310/ Notion: https://www.notion.com/ Oyster: https://www.oysterhr.com/ Pave: https://www.pave.com/ Rippling: https://www.rippling.com/ Snowflake: https://www.snowflake.com/ Verkada: https://www.verkada.com/ Webflow: https://webflow.com/ Yash Tekriwal: https://www.linkedin.com/in/yashtekriwal/ – Where to find Varun: LinkedIn: https://www.linkedin.com/in/vaanand/ Twitter/X: https://x.com/vxanand – Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Teaser + Introduction (03:13) Turning traditional GTM on its head (05:37) How Clay hustled for its first customers: Reddit threads & WhatsApp groups (08:53) Unpacking Clay's credit-based pricing (14:29) Building Clay's self-serve engine (16:54) Why Clay rejected the usage-based model (19:04) Clay’s big bet on content (23:59) How "reverse demos" win enterprise deals (27:49) 3 changes that unlocked Clay's upmarket motion (36:59) How to build trust with enterprise buyers (38:49) Applying the land and expand model (40:40) Hiring people who are “technical enough” (46:33) Inside Clay’s hands-on interviewing process (48:15) Why Clay invested in brand from day-one (50:21) Clay’s contrarian take on compensation (58:35) The person who shaped Varun’s career Varun Anand is the co-founder and Head of Operations at Clay, a GTM development environment that combines data and AI to help over 5000 companies power everything from CRM enrichment to highly targeted outreach campaigns. Clay recently announced their Series B expansion, raising $40M at a $1.25B valuation. Before Clay, Varun was the Director of Operations at Newfront and the Head of Expansion at Candid. Varun also spent four years working on Hillary Clinton’s presidential campaign.

–

In today’s episode, we discuss:

  • Clay’s unconventional GTM machine
  • 3 changes that unlocked Clay's upmarket motion
  • Layering enterprise customers on top of PLG
  • Scrappy sales tactics: WhatsApp groups, Reddit threads, and reverse demos
  • Thinking long-term about brand and content
  • Building an elite team of people who are “technical enough”
  • Clay’s contrarian take on compensation
  • Much more

–

Referenced:

–

Where to find Varun:

–

Where to find Brett:

–

Where to find First Round Capital:

–

Timestamps:

(00:00) Teaser + Introduction

(03:13) Turning traditional GTM on its head

(05:37) How Clay hustled for its first customers: Reddit threads & WhatsApp groups

(08:53) Unpacking Clay's credit-based pricing

(14:29) Building Clay's self-serve engine

(16:54) Why Clay rejected the usage-based model

(19:04) Clay’s big bet on content

(23:59) How "reverse demos" win enterprise deals

(27:49) 3 changes that unlocked Clay's upmarket motion

(36:59) How to build trust with enterprise buyers

(38:49) Applying the land and expand model

(40:40) Hiring people who are “technical enough”

(46:33) Inside Clay’s hands-on interviewing process

(48:15) Why Clay invested in brand from day-one

(50:21) Clay’s contrarian take on compensation

(58:35) The person who shaped Varun’s career

]]> 3751 Building a 4 billion dollar data platform: Inside dbt Labs’ unconventional path | Tristan Handy (Co-founder and CEO, ex-RJMetrics, Squarespace) Tristan Handy is the Founder and CEO at dbt Labs, a cloud-based data management platform that has raised over $400M to date, and was last valued at $4.2B in 2022. Dbt Labs has grown from just three companies using its free tool in 2016 to an ecosystem of 30,000+ enterprise users. Before founding dbt Labs, Tristan was the VP of Marketing at RJMetrics and the Director of Operations at Squarespace. – In today’s episode, we discuss: Dbt’s explosive growth The strategic pivot from consulting to a software company Unexpected strategies for building a tech category from scratch The critical moment: Why and when dbt Labs sought venture funding How to drive commercial adoption after open-sourcing Two things every founder CEO should do Much more – Referenced: Amazon Redshift: https://aws.amazon.com/redshift/ Bob Moore: https://www.linkedin.com/in/robertjmoore/ Crossbeam: https://www.crossbeam.com/ dbt Labs: https://www.getdbt.com/ Drew Banin: https://www.linkedin.com/in/drewbanin/ Jerry Colonna: https://www.reboot.io/team/jerry-colonna/ RJMetrics: https://en.wikipedia.org/wiki/RJMetrics SeatGeek: https://seatgeek.com/ Steve Ritter: https://www.linkedin.com/in/steve-ritter-69495210/ Squarespace: https://www.squarespace.com/ – Where to find Tristan: LinkedIn: https://www.linkedin.com/in/tristanhandy/ Twitter/X: https://x.com/jthandy – Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Introduction (02:56) The critical oversight in data analysis (05:41) Becoming an “accidental founder” (07:04) Inside the unique decision to start a consultancy (08:17) The game-changing principle behind dbt Labs’ rapid growth (11:20) Finding dbt Labs’ first customers (15:52) Consulting's hidden scalability (17:25) How dbt Labs created a new category (21:03) The anti-demo strategy (23:59) Community hacking: the Slack group that changed everything (26:00) The open source philosophy (27:39) When growth went exponential (28:49) How consulting engagements shaped the roadmap (30:02) Fundraising only when “things started to break” (32:40) Consultancy superpowers: the hidden advantages (34:04) Pivoting from consulting to software (40:00) Key monetization strategies (48:56) Why “begrudging” CEOs can be successful (51:02) Advice for finding PMF: “It’s not a playbook” (51:59) Lowering your standards is a hack (53:30) Navigating emotional overwhelm (54:25) Every CEO needs a coach Thu, 19 Dec 2024 12:00:00 -0000 Building a 4 billion dollar data platform: Inside dbt Labs’ unconventional path | Tristan Handy (Founder and CEO, ex-RJMetrics, Squarespace) full First Round Tristan Handy is the Founder and CEO at dbt Labs, a cloud-based data management platform that has raised over $400M to date, and was last valued at $4.2B in 2022. Dbt Labs has grown from just three companies using its free tool in 2016 to an ecosystem of 30,000+ enterprise users. Before founding dbt Labs, Tristan was the VP of Marketing at RJMetrics and the Director of Operations at Squarespace. – In today’s episode, we discuss: Dbt’s explosive growth The strategic pivot from consulting to a software company Unexpected strategies for building a tech category from scratch The critical moment: Why and when dbt Labs sought venture funding How to drive commercial adoption after open-sourcing Two things every founder CEO should do Much more – Referenced: Amazon Redshift: https://aws.amazon.com/redshift/ Bob Moore: https://www.linkedin.com/in/robertjmoore/ Crossbeam: https://www.crossbeam.com/ dbt Labs: https://www.getdbt.com/ Drew Banin: https://www.linkedin.com/in/drewbanin/ Jerry Colonna: https://www.reboot.io/team/jerry-colonna/ RJMetrics: https://en.wikipedia.org/wiki/RJMetrics SeatGeek: https://seatgeek.com/ Steve Ritter: https://www.linkedin.com/in/steve-ritter-69495210/ Squarespace: https://www.squarespace.com/ – Where to find Tristan: LinkedIn: https://www.linkedin.com/in/tristanhandy/ Twitter/X: https://x.com/jthandy – Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Introduction (02:56) The critical oversight in data analysis (05:41) Becoming an “accidental founder” (07:04) Inside the unique decision to start a consultancy (08:17) The game-changing principle behind dbt Labs’ rapid growth (11:20) Finding dbt Labs’ first customers (15:52) Consulting's hidden scalability (17:25) How dbt Labs created a new category (21:03) The anti-demo strategy (23:59) Community hacking: the Slack group that changed everything (26:00) The open source philosophy (27:39) When growth went exponential (28:49) How consulting engagements shaped the roadmap (30:02) Fundraising only when “things started to break” (32:40) Consultancy superpowers: the hidden advantages (34:04) Pivoting from consulting to software (40:00) Key monetization strategies (48:56) Why “begrudging” CEOs can be successful (51:02) Advice for finding PMF: “It’s not a playbook” (51:59) Lowering your standards is a hack (53:30) Navigating emotional overwhelm (54:25) Every CEO needs a coach Tristan Handy is the Founder and CEO at dbt Labs, a cloud-based data management platform that has raised over $400M to date, and was last valued at $4.2B in 2022. Dbt Labs has grown from just three companies using its free tool in 2016 to an ecosystem of 30,000+ enterprise users. Before founding dbt Labs, Tristan was the VP of Marketing at RJMetrics and the Director of Operations at Squarespace.

–

In today’s episode, we discuss:

  • Dbt’s explosive growth
  • The strategic pivot from consulting to a software company
  • Unexpected strategies for building a tech category from scratch
  • The critical moment: Why and when dbt Labs sought venture funding
  • How to drive commercial adoption after open-sourcing
  • Two things every founder CEO should do
  • Much more

–

Referenced:

–

Where to find Tristan:

–

Where to find Brett:

–

Where to find First Round Capital:

–

Timestamps:

(00:00) Introduction

(02:56) The critical oversight in data analysis

(05:41) Becoming an “accidental founder”

(07:04) Inside the unique decision to start a consultancy

(08:17) The game-changing principle behind dbt Labs’ rapid growth

(11:20) Finding dbt Labs’ first customers

(15:52) Consulting's hidden scalability

(17:25) How dbt Labs created a new category

(21:03) The anti-demo strategy

(23:59) Community hacking: the Slack group that changed everything

(26:00) The open source philosophy

(27:39) When growth went exponential

(28:49) How consulting engagements shaped the roadmap

(30:02) Fundraising only when “things started to break”

(32:40) Consultancy superpowers: the hidden advantages

(34:04) Pivoting from consulting to software

(40:00) Key monetization strategies

(48:56) Why “begrudging” CEOs can be successful

(51:02) Advice for finding PMF: “It’s not a playbook”

(51:59) Lowering your standards is a hack

(53:30) Navigating emotional overwhelm

(54:25) Every CEO needs a coach

]]> 3321 How Figma taps into taste, simplicity, and storytelling | Yuhki Yamashita (CPO at Figma, ex-Uber, Google, Microsoft) Yuhki Yamashita is the Chief Product Officer at Figma, leading the product and design teams. Previously, he was a product and design leader at Uber, where he orchestrated the redesign of the rider and driver apps. Yuhki was also a product manager at Google (YouTube iOS app) and Microsoft (Hotmail). Additionally, he has taught introductory computer science at Harvard University. In today’s episode, we discuss: How Figma approaches new products, prioritization, and storytelling Product culture at Uber, Microsoft, Google The difference between “good” and “extraordinary” PMs Tactical advice for storytelling The “un-learning” required in new jobs and industries – Referenced: Figjam: https://www.figma.com/figjam/ Figma: https://www.figma.com/ Figma Dev Mode: https://www.figma.com/dev-mode/ Figma Slides: https://www.figma.com/slides/ – Where to find Yuhki: LinkedIn: https://www.linkedin.com/in/yuhki/ Twitter/X: https://x.com/yuhkiyam – Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – (00:00) Introduction (02:50) Figma's early days (09:11) Product culture across companies (13:42) Knowing when to change things (17:40) How business goals impact product expansion (21:00) Advice for going multi-product (24:30) The skills of a “0 to 1” PM (27:36) Identifying entrepreneurial talent (29:06) Why aren't there more designer founders? (35:22) How Figma launches new products (41:19) “0 to 1” versus “1 to 10” talent (46:01) The role of storytelling at Figma (49:22) How Figma prioritizes product (55:11) Advice for product storytelling (59:02) “Good” vs “extraordinary” product managers (61:21) Why product simplicity matters (63:52) The importance of taste in product and design (67:56) The biggest influence on Yuhki’s product thinking Thu, 05 Dec 2024 12:00:00 -0000 How Figma taps into taste, simplicity, and storytelling | Yuhki Yamashita (CPO at Figma, ex-Uber, Google, Microsoft) full First Round Yuhki Yamashita is the Chief Product Officer at Figma, leading the product and design teams. Previously, he was a product and design leader at Uber, where he orchestrated the redesign of the rider and driver apps. Yuhki was also a product manager at Google (YouTube iOS app) and Microsoft (Hotmail). Additionally, he has taught introductory computer science at Harvard University. Yuhki Yamashita is the Chief Product Officer at Figma, leading the product and design teams. Previously, he was a product and design leader at Uber, where he orchestrated the redesign of the rider and driver apps. Yuhki was also a product manager at Google (YouTube iOS app) and Microsoft (Hotmail). Additionally, he has taught introductory computer science at Harvard University. In today’s episode, we discuss: How Figma approaches new products, prioritization, and storytelling Product culture at Uber, Microsoft, Google The difference between “good” and “extraordinary” PMs Tactical advice for storytelling The “un-learning” required in new jobs and industries – Referenced: Figjam: https://www.figma.com/figjam/ Figma: https://www.figma.com/ Figma Dev Mode: https://www.figma.com/dev-mode/ Figma Slides: https://www.figma.com/slides/ – Where to find Yuhki: LinkedIn: https://www.linkedin.com/in/yuhki/ Twitter/X: https://x.com/yuhkiyam – Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – (00:00) Introduction (02:50) Figma's early days (09:11) Product culture across companies (13:42) Knowing when to change things (17:40) How business goals impact product expansion (21:00) Advice for going multi-product (24:30) The skills of a “0 to 1” PM (27:36) Identifying entrepreneurial talent (29:06) Why aren't there more designer founders? (35:22) How Figma launches new products (41:19) “0 to 1” versus “1 to 10” talent (46:01) The role of storytelling at Figma (49:22) How Figma prioritizes product (55:11) Advice for product storytelling (59:02) “Good” vs “extraordinary” product managers (61:21) Why product simplicity matters (63:52) The importance of taste in product and design (67:56) The biggest influence on Yuhki’s product thinking Yuhki Yamashita is the Chief Product Officer at Figma, leading the product and design teams. Previously, he was a product and design leader at Uber, where he orchestrated the redesign of the rider and driver apps. Yuhki was also a product manager at Google (YouTube iOS app) and Microsoft (Hotmail). Additionally, he has taught introductory computer science at Harvard University.

In today’s episode, we discuss:

  • How Figma approaches new products, prioritization, and storytelling
  • Product culture at Uber, Microsoft, Google
  • The difference between “good” and “extraordinary” PMs
  • Tactical advice for storytelling
  • The “un-learning” required in new jobs and industries

–

Referenced:

–

Where to find Yuhki:

–

Where to find Brett:

–

Where to find First Round Capital:

–

(00:00) Introduction

(02:50) Figma's early days

(09:11) Product culture across companies

(13:42) Knowing when to change things

(17:40) How business goals impact product expansion

(21:00) Advice for going multi-product

(24:30) The skills of a “0 to 1” PM

(27:36) Identifying entrepreneurial talent

(29:06) Why aren't there more designer founders?

(35:22) How Figma launches new products

(41:19) “0 to 1” versus “1 to 10” talent

(46:01) The role of storytelling at Figma

(49:22) How Figma prioritizes product

(55:11) Advice for product storytelling

(59:02) “Good” vs “extraordinary” product managers

(61:21) Why product simplicity matters

(63:52) The importance of taste in product and design

(67:56) The biggest influence on Yuhki’s product thinking

]]> 4192 How to find customers in the Dept of Defense: From prototype to the Pentagon | Steve Blank (Hacking for Defense) Steve Blank is an Adjunct Professor at Stanford University, where he co-created the "Hacking for Defense" curriculum for the Department of Defense. As a consultant to top defense and intelligence organizations, Steve brings cutting-edge strategies to the national security sector. Before entering academia, Steve built eight different startups. He helped launch the Lean Startup movement with his May 2013 Harvard Business Review cover story. Steve also authored the acclaimed business books "The Four Steps to the Epiphany" and "The Startup Owner's Manual.” This episode’s is guest host is Meka Asonye, a Partner at First Round Capital. Before joining First Round as an investor, Meka led go-to-market teams at both Stripe and Mixpanel. – In today’s episode we discuss: Commercial versus military market strategies Finding mission solution fit The hidden challenges most startups miss Building relationships in National Security The new generation of “defense founders” Much more – Referenced: Alexander Osterwalder: https://www.linkedin.com/in/osterwalder/ Department of Defense: https://www.defense.gov/ Eric Ries: https://www.linkedin.com/in/eries/ Hacking for Defense: https://hackingfordefense-prod.stanford.edu/ How Saboteurs Threaten Innovation: https://steveblank.com/2024/07/30/why-large-organizations-struggle-with-disruption-and-what-to-do-about-it/ How to find your customer in the Dept of Defense: https://steveblank.com/2024/09/17/the-directory-of-dod-program-executive-offices-and-officers-peos/ Mission Model Canvas: https://steveblank.com/2019/09/ Pete Newell: https://www.linkedin.com/in/petenewell/ Special Operations Command: https://www.socom.mil/ The Frozen Middle: https://steveblank.com/2024/07/30/why-large-organizations-struggle-with-disruption-and-what-to-do-about-it/ The Hacking for Defense Manual: https://stanfordh4d.substack.com/p/the-hacking-for-defense-manual-a The Hacking for Defense Course: https://www.h4d.us/ The lean launchpad at Stanford: https://steveblank.com/2011/05/10/the-lean-launchpad-at-stanford-–-the-final-presentations/ The Secret History of Silicon Valley: https://steveblank.com/secret-history/ – Where to find Steve: LinkedIn: https://www.linkedin.com/in/steveblank/ Twitter/X: https://twitter.com/sgblank Website: https://steveblank.com/ – Where to find Meka: LinkedIn: https://www.linkedin.com/in/mekaasonye/ Twitter/X: https://x.com/bigmekastyle – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Introduction (02:27) Validating ideas for defense products (03:57) Guide to military sales and procurement (07:15) Rethinking GTM strategies (10:13) Building a network in national security (15:07) The dual-use debate (18:35) Behind the rising number of “defense founders” (22:30) “Mission solution fit” (24:35) Breaking new ground in military tech (26:09) Essential resources for any defense founder (28:59) What’s missing from Silicon Valley Thu, 14 Nov 2024 12:00:00 -0000 full First Round Steve Blank is an Adjunct Professor at Stanford University, where he co-created the "Hacking for Defense" curriculum for the Department of Defense. Steve Blank is an Adjunct Professor at Stanford University, where he co-created the "Hacking for Defense" curriculum for the Department of Defense. As a consultant to top defense and intelligence organizations, Steve brings cutting-edge strategies to the national security sector. Before entering academia, Steve built eight different startups. He helped launch the Lean Startup movement with his May 2013 Harvard Business Review cover story. Steve also authored the acclaimed business books "The Four Steps to the Epiphany" and "The Startup Owner's Manual.” This episode’s is guest host is Meka Asonye, a Partner at First Round Capital. Before joining First Round as an investor, Meka led go-to-market teams at both Stripe and Mixpanel. – In today’s episode we discuss: Commercial versus military market strategies Finding mission solution fit The hidden challenges most startups miss Building relationships in National Security The new generation of “defense founders” Much more – Referenced: Alexander Osterwalder: https://www.linkedin.com/in/osterwalder/ Department of Defense: https://www.defense.gov/ Eric Ries: https://www.linkedin.com/in/eries/ Hacking for Defense: https://hackingfordefense-prod.stanford.edu/ How Saboteurs Threaten Innovation: https://steveblank.com/2024/07/30/why-large-organizations-struggle-with-disruption-and-what-to-do-about-it/ How to find your customer in the Dept of Defense: https://steveblank.com/2024/09/17/the-directory-of-dod-program-executive-offices-and-officers-peos/ Mission Model Canvas: https://steveblank.com/2019/09/ Pete Newell: https://www.linkedin.com/in/petenewell/ Special Operations Command: https://www.socom.mil/ The Frozen Middle: https://steveblank.com/2024/07/30/why-large-organizations-struggle-with-disruption-and-what-to-do-about-it/ The Hacking for Defense Manual: https://stanfordh4d.substack.com/p/the-hacking-for-defense-manual-a The Hacking for Defense Course: https://www.h4d.us/ The lean launchpad at Stanford: https://steveblank.com/2011/05/10/the-lean-launchpad-at-stanford-–-the-final-presentations/ The Secret History of Silicon Valley: https://steveblank.com/secret-history/ – Where to find Steve: LinkedIn: https://www.linkedin.com/in/steveblank/ Twitter/X: https://twitter.com/sgblank Website: https://steveblank.com/ – Where to find Meka: LinkedIn: https://www.linkedin.com/in/mekaasonye/ Twitter/X: https://x.com/bigmekastyle – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Introduction (02:27) Validating ideas for defense products (03:57) Guide to military sales and procurement (07:15) Rethinking GTM strategies (10:13) Building a network in national security (15:07) The dual-use debate (18:35) Behind the rising number of “defense founders” (22:30) “Mission solution fit” (24:35) Breaking new ground in military tech (26:09) Essential resources for any defense founder (28:59) What’s missing from Silicon Valley Steve Blank is an Adjunct Professor at Stanford University, where he co-created the "Hacking for Defense" curriculum for the Department of Defense. As a consultant to top defense and intelligence organizations, Steve brings cutting-edge strategies to the national security sector. Before entering academia, Steve built eight different startups. He helped launch the Lean Startup movement with his May 2013 Harvard Business Review cover story. Steve also authored the acclaimed business books "The Four Steps to the Epiphany" and "The Startup Owner's Manual.”

This episode’s is guest host is Meka Asonye, a Partner at First Round Capital. Before joining First Round as an investor, Meka led go-to-market teams at both Stripe and Mixpanel.

–

In today’s episode we discuss:

  • Commercial versus military market strategies
  • Finding mission solution fit
  • The hidden challenges most startups miss
  • Building relationships in National Security
  • The new generation of “defense founders”
  • Much more

–

Referenced:

–

Where to find Steve:

–

Where to find Meka:

–

Where to find First Round Capital:

–

Timestamps:

(00:00) Introduction

(02:27) Validating ideas for defense products

(03:57) Guide to military sales and procurement

(07:15) Rethinking GTM strategies

(10:13) Building a network in national security

(15:07) The dual-use debate

(18:35) Behind the rising number of “defense founders”

(22:30) “Mission solution fit”

(24:35) Breaking new ground in military tech

(26:09) Essential resources for any defense founder

(28:59) What’s missing from Silicon Valley

]]> 2048 Shifting Career Altitudes: Insights from a CPO’s Journey Leading in Nearly Every Function | Anneka Gupta (Rubrik, ex-LiveRamp) Anneka Gupta is the Chief Product Officer at Rubrik, a cloud management and data security company with a US$6B market cap. Before Rubrik, Anneka spent 11 years leading various teams at LiveRamp, including product, go-to-market, and operations. In today’s episode, we discuss: How LiveRamp went from $30M to $200M ARR in 3 years Anneka’s jack-of-all-trades career Why specialist hires can backfire When leaders should get in the weeds One area every PM can improve in Rubrik’s approach to building product Much more – Referenced: Acxiom: https://www.acxiom.com/ Acxiom’s acquisition of LiveRamp: https://tinyurl.com/2shm83de Amazon: https://www.amazon.com/ Auren Hoffman: https://www.linkedin.com/in/auren/ Dentsu: https://www.dentsu.com/ Dentsu’s acquisition of Merkle: https://tinyurl.com/yvxe6fws James Arra: https://www.linkedin.com/in/james-arra-a43a06/ LiveRamp: https://liveramp.com/ Merkle: https://www.merkle.com/ Rubrik: https://www.rubrik.com/ Slack: https://www.slack.com/ Travis May: https://www.linkedin.com/in/stmay/ – Where to find Anneka Gupta: LinkedIn: https://www.linkedin.com/in/annekagupta/ Twitter/X: https://x.com/annekagupta – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Introduction (02:11) Inside LiveRamp’s unique growth journey (12:18) Anneka’s first PM role (14:20) Leading LiveRamp’s marketing function (16:17) Why the best product doesn’t win (21:06) Crafting products for different personas (24:53) Transitioning Acxiom’s customers to LiveRamp (33:54) Why Acxiom chose to buy not build (36:40) Anneka's leap to GM and product leader (38:22) How 17 diverse roles shaped Anneka’s CPO approach (40:54) The hidden career growth hack (43:15) Where domain experience is overrated (50:33) Mastering the art of altitude shifting (53:54) PMs should undergo the same training as sales reps (59:37) Strategies for selling to new personas (62:40) Lessons from Anneka’s mistake at LiveRamp (67:56) Who had an outsized impact on Anneka Thu, 10 Oct 2024 11:00:00 -0000 Shifting Career Altitudes: Insights from a CPO’s Journey Leading in Nearly Every Function | Anneka Gupta (Rubrik, ex-LiveRamp) full First Round Anneka Gupta is the Chief Product Officer at Rubrik, a cloud management and data security company with a US$6B market cap. Before Rubrik, Anneka spent 11 years leading various teams at LiveRamp, including product, go-to-market, and operations. Anneka Gupta is the Chief Product Officer at Rubrik, a cloud management and data security company with a US$6B market cap. Before Rubrik, Anneka spent 11 years leading various teams at LiveRamp, including product, go-to-market, and operations. In today’s episode, we discuss: How LiveRamp went from $30M to $200M ARR in 3 years Anneka’s jack-of-all-trades career Why specialist hires can backfire When leaders should get in the weeds One area every PM can improve in Rubrik’s approach to building product Much more – Referenced: Acxiom: https://www.acxiom.com/ Acxiom’s acquisition of LiveRamp: https://tinyurl.com/2shm83de Amazon: https://www.amazon.com/ Auren Hoffman: https://www.linkedin.com/in/auren/ Dentsu: https://www.dentsu.com/ Dentsu’s acquisition of Merkle: https://tinyurl.com/yvxe6fws James Arra: https://www.linkedin.com/in/james-arra-a43a06/ LiveRamp: https://liveramp.com/ Merkle: https://www.merkle.com/ Rubrik: https://www.rubrik.com/ Slack: https://www.slack.com/ Travis May: https://www.linkedin.com/in/stmay/ – Where to find Anneka Gupta: LinkedIn: https://www.linkedin.com/in/annekagupta/ Twitter/X: https://x.com/annekagupta – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Introduction (02:11) Inside LiveRamp’s unique growth journey (12:18) Anneka’s first PM role (14:20) Leading LiveRamp’s marketing function (16:17) Why the best product doesn’t win (21:06) Crafting products for different personas (24:53) Transitioning Acxiom’s customers to LiveRamp (33:54) Why Acxiom chose to buy not build (36:40) Anneka's leap to GM and product leader (38:22) How 17 diverse roles shaped Anneka’s CPO approach (40:54) The hidden career growth hack (43:15) Where domain experience is overrated (50:33) Mastering the art of altitude shifting (53:54) PMs should undergo the same training as sales reps (59:37) Strategies for selling to new personas (62:40) Lessons from Anneka’s mistake at LiveRamp (67:56) Who had an outsized impact on Anneka Anneka Gupta is the Chief Product Officer at Rubrik, a cloud management and data security company with a US$6B market cap. Before Rubrik, Anneka spent 11 years leading various teams at LiveRamp, including product, go-to-market, and operations.

In today’s episode, we discuss:

  • How LiveRamp went from $30M to $200M ARR in 3 years
  • Anneka’s jack-of-all-trades career
  • Why specialist hires can backfire
  • When leaders should get in the weeds
  • One area every PM can improve in
  • Rubrik’s approach to building product
  • Much more

–

Referenced:

–

Where to find Anneka Gupta:

–

Where to find Brett Berson:

–

Where to find First Round Capital:

–

Timestamps:

(00:00) Introduction

(02:11) Inside LiveRamp’s unique growth journey

(12:18) Anneka’s first PM role

(14:20) Leading LiveRamp’s marketing function

(16:17) Why the best product doesn’t win

(21:06) Crafting products for different personas

(24:53) Transitioning Acxiom’s customers to LiveRamp

(33:54) Why Acxiom chose to buy not build

(36:40) Anneka's leap to GM and product leader

(38:22) How 17 diverse roles shaped Anneka’s CPO approach

(40:54) The hidden career growth hack

(43:15) Where domain experience is overrated

(50:33) Mastering the art of altitude shifting

(53:54) PMs should undergo the same training as sales reps

(59:37) Strategies for selling to new personas

(62:40) Lessons from Anneka’s mistake at LiveRamp

(67:56) Who had an outsized impact on Anneka

]]> 4193 How to find and pull startup growth levers | Matt Lerner (Founder and CEO at SYSTM, Author of Growth Levers) Matt Lerner is the Founder and CEO at SYSTM, a startup coaching consultancy that helps high-potential companies grow their business. Matt also authored the book “Growth Levers”, which shares his framework that's helped over 200 seed-stage startups grow as much as 100x. Previously, Matt was on the early growth team at PayPal, a partner at 500 Startups, and a guest lecturer at Stanford Business School. - In today’s episode, we discuss: Understanding the key drivers of startup success Applying the Growth Lever framework Several case studies Customer-centric growth tactics Adapting growth levers for different business models - Referenced: Airbnb: https://www.airbnb.com/ Bold Commerce: https://boldcommerce.com/ Calm: https://www.calm.com/ Caribou: https://www.usecaribou.com/ eBay: https://www.ebay.com/ FATMAP: https://fatmap.com/ Growth Levers and How to Find Them: https://www.systm.co/growth-levers-matt-lerner-book PayPal: https://www.paypal.com/ Peter Karpas: https://www.linkedin.com/in/peterkarpas/ Popsa: https://popsa.com/ Shopify: https://www.shopify.com/ Sonic Jobs: https://www.sonicjobs.com/ SYSTM: https://www.systm.co/ - Where to find Matt Lerner: LinkedIn: https://www.linkedin.com/in/matthewlerner/ Twitter/X: https://x.com/matthlerner - Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson - Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast - Timestamps: (00:00) Intro (03:11) The hidden truth about startup success (05:10) Popsa's journey: A case study in growth (07:31) Breaking down the growth lever framework (11:30) Understanding the customer's journey (14:14) The art of customer interviews (18:07) Unlocking growth through customer insights (24:23) The triple threat: Founder failure modes (27:32) The power of founder-led growth strategies (32:42) Unlocking growth bottlenecks (36:40) Timing and implementation of growth strategies (39:43) Founder red flags (41:32) Crafting effective growth experiments (43:14) Why customer mindset is the ultimate growth driver (46:19) The power law of business (48:59) Why startups don’t need paid marketing (50:47) Growth levers for sales-driven companies (53:43) Matt's own application of growth principles (55:39) Growth levers in B2B sales (57:05) Finding customer "locksmith moments" (64:08) The mentor who shaped Matt's thinking Thu, 26 Sep 2024 11:00:00 -0000 How to find and pull startup growth levers | Matt Lerner (Founder and CEO at SYSTM, Author of Growth Levers) full 135 First Round Matt Lerner is the Founder and CEO at SYSTM and the author of "Growth Levers" Matt Lerner is the Founder and CEO at SYSTM, a startup coaching consultancy that helps high-potential companies grow their business. Matt also authored the book “Growth Levers”, which shares his framework that's helped over 200 seed-stage startups grow as much as 100x. Previously, Matt was on the early growth team at PayPal, a partner at 500 Startups, and a guest lecturer at Stanford Business School. - In today’s episode, we discuss: Understanding the key drivers of startup success Applying the Growth Lever framework Several case studies Customer-centric growth tactics Adapting growth levers for different business models - Referenced: Airbnb: https://www.airbnb.com/ Bold Commerce: https://boldcommerce.com/ Calm: https://www.calm.com/ Caribou: https://www.usecaribou.com/ eBay: https://www.ebay.com/ FATMAP: https://fatmap.com/ Growth Levers and How to Find Them: https://www.systm.co/growth-levers-matt-lerner-book PayPal: https://www.paypal.com/ Peter Karpas: https://www.linkedin.com/in/peterkarpas/ Popsa: https://popsa.com/ Shopify: https://www.shopify.com/ Sonic Jobs: https://www.sonicjobs.com/ SYSTM: https://www.systm.co/ - Where to find Matt Lerner: LinkedIn: https://www.linkedin.com/in/matthewlerner/ Twitter/X: https://x.com/matthlerner - Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson - Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast - Timestamps: (00:00) Intro (03:11) The hidden truth about startup success (05:10) Popsa's journey: A case study in growth (07:31) Breaking down the growth lever framework (11:30) Understanding the customer's journey (14:14) The art of customer interviews (18:07) Unlocking growth through customer insights (24:23) The triple threat: Founder failure modes (27:32) The power of founder-led growth strategies (32:42) Unlocking growth bottlenecks (36:40) Timing and implementation of growth strategies (39:43) Founder red flags (41:32) Crafting effective growth experiments (43:14) Why customer mindset is the ultimate growth driver (46:19) The power law of business (48:59) Why startups don’t need paid marketing (50:47) Growth levers for sales-driven companies (53:43) Matt's own application of growth principles (55:39) Growth levers in B2B sales (57:05) Finding customer "locksmith moments" (64:08) The mentor who shaped Matt's thinking Matt Lerner is the Founder and CEO at SYSTM, a startup coaching consultancy that helps high-potential companies grow their business. Matt also authored the book “Growth Levers”, which shares his framework that's helped over 200 seed-stage startups grow as much as 100x. Previously, Matt was on the early growth team at PayPal, a partner at 500 Startups, and a guest lecturer at Stanford Business School.

-

In today’s episode, we discuss:

  • Understanding the key drivers of startup success
  • Applying the Growth Lever framework
  • Several case studies
  • Customer-centric growth tactics
  • Adapting growth levers for different business models

-

Referenced:

-

Where to find Matt Lerner:

-

Where to find Brett Berson:

-

Where to find First Round Capital:

-

Timestamps:

(00:00) Intro

(03:11) The hidden truth about startup success

(05:10) Popsa's journey: A case study in growth

(07:31) Breaking down the growth lever framework

(11:30) Understanding the customer's journey

(14:14) The art of customer interviews

(18:07) Unlocking growth through customer insights

(24:23) The triple threat: Founder failure modes

(27:32) The power of founder-led growth strategies

(32:42) Unlocking growth bottlenecks

(36:40) Timing and implementation of growth strategies

(39:43) Founder red flags

(41:32) Crafting effective growth experiments

(43:14) Why customer mindset is the ultimate growth driver

(46:19) The power law of business

(48:59) Why startups don’t need paid marketing

(50:47) Growth levers for sales-driven companies

(53:43) Matt's own application of growth principles

(55:39) Growth levers in B2B sales

(57:05) Finding customer "locksmith moments"

(64:08) The mentor who shaped Matt's thinking

]]> 3957 How to find — and keep — product-market fit | Bob Moore (Co-founder and CEO at Crossbeam, ex-RJMetrics and Stitch Data) Bob Moore is the co-founder and CEO at Crossbeam, a “LinkedIn for data” platform that helps companies find overlapping opportunities with their partners. Crossbeam has raised US$117M to date and recently acquired Reveal in 2024. Bob previously cofounded RJMetrics (now part of Adobe Commerce Cloud) and Stitch Data (acquired by Talend). He is also the author of Ecosystem-Led Growth. In today’s episode, we discuss: The unique way he evaluated and validated startup ideas Lessons learned from falling in and out of product-market fit How to recognize and act on market shifts that impact your business Specific tactics for distribution and building with conviction vs. consensus Creating scalable and durable startups Unlocking network effects in software Getting mergers right – Referenced: Adobe’s acquisition of Magento: https://techcrunch.com/2018/05/21/adobe-to-acquire-magento-for-1-6-b/ Amazon Redshift: https://aws.amazon.com/redshift/ Chris Merrick: https://www.linkedin.com/in/merrickchristopher/ Crossbeam: https://www.crossbeam.com/ Crossbeam/Reveal merger: https://www.crossbeam.com/crossbeam-and-reveal-merger-announcement/ Ecosystem-Led Growth: https://www.robertjmoore.com/book Jake Stein: https://www.linkedin.com/in/jakestein/ Nick Mehta: https://www.linkedin.com/in/nickmehta/ Reveal: https://reveal.co/ Rick Nucci: https://www.linkedin.com/in/ricknucci/ RJMetrics: https://en.wikipedia.org/wiki/RJMetrics Simon Bouchez: https://www.linkedin.com/in/simonbouchez/ Stitch Data: https://www.stitchdata.com/ Talend’s acquisition of Stitch Data: https://www.businessinsider.com/talend-acquires-stitch-2018-11 The 4 Levels of PMF: https://pmf.firstround.com/levels – Where to find Bob Moore: LinkedIn: https://www.linkedin.com/in/robertjmoore/ Twitter/X: https://x.com/robertjmoore – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Intro (02:44) Tactics for finding founder-market fit (06:17) Speaking to founders about startup ideas (11:16) Why founders loved Crossbeam (19:34) How RJMetrics found market fit then lost it (29:46) Lessons from RJMetrics’ exit (38:06) The importance of intellectual honesty (39:33) Building with conviction versus consensus (42:41) Lessons from a three-time founder (50:26) Building and distributing Crossbeam (57:58) The “joint jam” sales tactic (60:35) Unlocking network effects in a software business (63:27) Why Crossbeam merged with its competitor (72:51) Who had an outsized impact on Bob Thu, 19 Sep 2024 11:00:00 -0000 full First Round Bob Moore is the co-founder and CEO at Crossbeam, a “LinkedIn for data” platform that helps companies find overlapping opportunities with their partners. Crossbeam has raised US$117M to date and recently acquired Reveal in 2024. Bob previously cofounded RJMetrics (now part of Adobe Commerce Cloud) and Stitch Data (acquired by Talend). He is also the author of Ecosystem-Led Growth. In today’s episode, we discuss: The unique way he evaluated and validated startup ideas Lessons learned from falling in and out of product-market fit How to recognize and act on market shifts that impact your business Specific tactics for distribution and building with conviction vs. consensus Creating scalable and durable startups Unlocking network effects in software Getting mergers right – Referenced: Adobe’s acquisition of Magento: https://techcrunch.com/2018/05/21/adobe-to-acquire-magento-for-1-6-b/ Amazon Redshift: https://aws.amazon.com/redshift/ Chris Merrick: https://www.linkedin.com/in/merrickchristopher/ Crossbeam: https://www.crossbeam.com/ Crossbeam/Reveal merger: https://www.crossbeam.com/crossbeam-and-reveal-merger-announcement/ Ecosystem-Led Growth: https://www.robertjmoore.com/book Jake Stein: https://www.linkedin.com/in/jakestein/ Nick Mehta: https://www.linkedin.com/in/nickmehta/ Reveal: https://reveal.co/ Rick Nucci: https://www.linkedin.com/in/ricknucci/ RJMetrics: https://en.wikipedia.org/wiki/RJMetrics Simon Bouchez: https://www.linkedin.com/in/simonbouchez/ Stitch Data: https://www.stitchdata.com/ Talend’s acquisition of Stitch Data: https://www.businessinsider.com/talend-acquires-stitch-2018-11 The 4 Levels of PMF: https://pmf.firstround.com/levels – Where to find Bob Moore: LinkedIn: https://www.linkedin.com/in/robertjmoore/ Twitter/X: https://x.com/robertjmoore – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Intro (02:44) Tactics for finding founder-market fit (06:17) Speaking to founders about startup ideas (11:16) Why founders loved Crossbeam (19:34) How RJMetrics found market fit then lost it (29:46) Lessons from RJMetrics’ exit (38:06) The importance of intellectual honesty (39:33) Building with conviction versus consensus (42:41) Lessons from a three-time founder (50:26) Building and distributing Crossbeam (57:58) The “joint jam” sales tactic (60:35) Unlocking network effects in a software business (63:27) Why Crossbeam merged with its competitor (72:51) Who had an outsized impact on Bob Bob Moore is the co-founder and CEO at Crossbeam, a “LinkedIn for data” platform that helps companies find overlapping opportunities with their partners. Crossbeam has raised US$117M to date and recently acquired Reveal in 2024. Bob previously cofounded RJMetrics (now part of Adobe Commerce Cloud) and Stitch Data (acquired by Talend). He is also the author of Ecosystem-Led Growth.

In today’s episode, we discuss:

  • The unique way he evaluated and validated startup ideas
  • Lessons learned from falling in and out of product-market fit
  • How to recognize and act on market shifts that impact your business
  • Specific tactics for distribution and building with conviction vs. consensus
  • Creating scalable and durable startups
  • Unlocking network effects in software
  • Getting mergers right

–

Referenced:

–

Where to find Bob Moore:

–

Where to find Brett Berson:

–

Where to find First Round Capital:

–

Timestamps:

(00:00) Intro

(02:44) Tactics for finding founder-market fit

(06:17) Speaking to founders about startup ideas

(11:16) Why founders loved Crossbeam

(19:34) How RJMetrics found market fit then lost it

(29:46) Lessons from RJMetrics’ exit

(38:06) The importance of intellectual honesty

(39:33) Building with conviction versus consensus

(42:41) Lessons from a three-time founder

(50:26) Building and distributing Crossbeam

(57:58) The “joint jam” sales tactic

(60:35) Unlocking network effects in a software business

(63:27) Why Crossbeam merged with its competitor

(72:51) Who had an outsized impact on Bob

]]> 4712 Rebooting Intercom: Eoghan McCabe on Defying Silicon Valley Orthodoxy | Co-founder & CEO Eoghan McCabe is the CEO and cofounder at Intercom, an AI customer service platform. Intercom has raised over $240M, and was last valued at $1.3B in 2018. After spending 9 years building the company, Eoghan left Intercom in 2020, but he’s since returned, reshaping Intercom and pioneering its pivot to an AI-first service. This episode highlights his unabashed takes on leaning into your intuition as a founder, and his perspectives on the critical junctures in company building. – In today’s episode, we also discuss: Eoghan's reflections since leaving Intercom The value of intuition and first-principles thinking The changes Eoghan made upon returning to Intercom How Eoghan increased Intercom's productivity by 41% Tactical advice on hiring top talent Why you can't make small improvements in big categories Crafting a culture of ruthless honesty and transparency Why software branding is in crisis – Referenced: 37signals: https://37signals.com Basecamp: https://basecamp.com Brian Halligan (HubSpot): https://www.linkedin.com/in/brianhalligan David Heinemeier Hansson (37signals, Basecamp): https://www.linkedin.com/in/david-heinemeier-hansson-374b18221 Intercom: https://www.intercom.com Jason Fried (37signals, Basecamp): https://www.linkedin.com/in/jason-fried Salesforce: https://www.salesforce.com Marc Benioff (Salesforce): https://www.linkedin.com/in/marcbenioff Zendesk: https://www.zendesk.com – Where to find Eoghan: LinkedIn: https://www.linkedin.com/in/eoghanmccabe/ Twitter/X: https://x.com/eoghan – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps 0:00:00 - Founder intuition vs. standard practice 0:25:00 - Silicon Valley knowledge loops 0:28:13 - Building an executive team 0:36:38 - Eoghan’s return to Intercom 0:42:02 - Transparent and honest leadership 0:46:42 - Changing Intercom’s strategy 0:54:22 - AI and category disruption 1:03:17 - How Intercom thinks about brand 1:10:40 - Eoghan’s inspirations Thu, 05 Sep 2024 11:00:00 -0000 Rebooting Intercom: Eoghan McCabe on Defying Silicon Valley Orthodoxy full First Round Eoghan McCabe is the CEO and cofounder at Intercom, an AI customer service platform. Intercom has raised over $240M, and was last valued at $1.3B in 2023. Eoghan McCabe is the CEO and cofounder at Intercom, an AI customer service platform. Intercom has raised over $240M, and was last valued at $1.3B in 2018. After spending 9 years building the company, Eoghan left Intercom in 2020, but he’s since returned, reshaping Intercom and pioneering its pivot to an AI-first service. This episode highlights his unabashed takes on leaning into your intuition as a founder, and his perspectives on the critical junctures in company building. – In today’s episode, we also discuss: Eoghan's reflections since leaving Intercom The value of intuition and first-principles thinking The changes Eoghan made upon returning to Intercom How Eoghan increased Intercom's productivity by 41% Tactical advice on hiring top talent Why you can't make small improvements in big categories Crafting a culture of ruthless honesty and transparency Why software branding is in crisis – Referenced: 37signals: https://37signals.com Basecamp: https://basecamp.com Brian Halligan (HubSpot): https://www.linkedin.com/in/brianhalligan David Heinemeier Hansson (37signals, Basecamp): https://www.linkedin.com/in/david-heinemeier-hansson-374b18221 Intercom: https://www.intercom.com Jason Fried (37signals, Basecamp): https://www.linkedin.com/in/jason-fried Salesforce: https://www.salesforce.com Marc Benioff (Salesforce): https://www.linkedin.com/in/marcbenioff Zendesk: https://www.zendesk.com – Where to find Eoghan: LinkedIn: https://www.linkedin.com/in/eoghanmccabe/ Twitter/X: https://x.com/eoghan – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps 0:00:00 - Founder intuition vs. standard practice 0:25:00 - Silicon Valley knowledge loops 0:28:13 - Building an executive team 0:36:38 - Eoghan’s return to Intercom 0:42:02 - Transparent and honest leadership 0:46:42 - Changing Intercom’s strategy 0:54:22 - AI and category disruption 1:03:17 - How Intercom thinks about brand 1:10:40 - Eoghan’s inspirations Eoghan McCabe is the CEO and cofounder at Intercom, an AI customer service platform. Intercom has raised over $240M, and was last valued at $1.3B in 2018. After spending 9 years building the company, Eoghan left Intercom in 2020, but he’s since returned, reshaping Intercom and pioneering its pivot to an AI-first service. This episode highlights his unabashed takes on leaning into your intuition as a founder, and his perspectives on the critical junctures in company building.

–

In today’s episode, we also discuss:

  • Eoghan's reflections since leaving Intercom
  • The value of intuition and first-principles thinking
  • The changes Eoghan made upon returning to Intercom
  • How Eoghan increased Intercom's productivity by 41%
  • Tactical advice on hiring top talent
  • Why you can't make small improvements in big categories
  • Crafting a culture of ruthless honesty and transparency
  • Why software branding is in crisis

–

Referenced:

–

Where to find Eoghan:

–

Where to find Brett Berson:

–

Where to find First Round Capital:

–

Timestamps

0:00:00 - Founder intuition vs. standard practice

0:25:00 - Silicon Valley knowledge loops

0:28:13 - Building an executive team

0:36:38 - Eoghan’s return to Intercom

0:42:02 - Transparent and honest leadership

0:46:42 - Changing Intercom’s strategy

0:54:22 - AI and category disruption

1:03:17 - How Intercom thinks about brand

1:10:40 - Eoghan’s inspirations

]]> 4520 Inside marketing at Stripe, OpenAI and Retool | Krithika Muthukumar (VP of Marketing at OpenAI, ex-Stripe, Retool, Dropbox, Google) Krithika Muthukumar is a marketing veteran. She is currently the VP of Marketing at OpenAI where she was the first marketing hire. Before that, she was Head of Marketing at Retool. Her longest tenure was at Stripe where she was hired as the first marketer and scaled with the company over nine years, from a 60-person team to 7500+. She began her career in Product Marketing at Google and Dropbox. – In today’s episode, we discuss: Marketing lessons from OpenAI, Stripe, and Retool The 3 pillars of Stripe’s approach to brand How to manage resource allocation as a marketer Adapting marketing strategy to different business models Advice for early marketing hires – Referenced: Coca-Cola AI-generated wish card campaign: https://theprint.in/ani-press-releases/coca-cola-ignites-diwali-celebrations-with-unique-personalized-ai-generated-wish-cards/1840093/ Cristina Cordova: https://www.linkedin.com/in/cristinajcordova/ Gong: https://www.gong.io/ Greg Brockman: https://www.linkedin.com/in/thegdb/ Kenzo Fong: https://www.linkedin.com/in/kenzofong/ Retool: https://retool.com/ Stripe’s “Capture the Flag” campaign: https://techcrunch.com/2012/08/22/stripes-capture-the-flag-2-0-a-hands-on-contest-for-app-developers-to-test-their-security-know-how/ Stripe Press: https://press.stripe.com/ Stripe Sigma: https://stripe.com/us/sigma Tanya Khakbaz: https://www.linkedin.com/in/tanya-khakbaz-a725732/ – Where to find Krithika Muthukumar: LinkedIn: https://www.linkedin.com/in/krithix/ Twitter/X: https://x.com/krithix – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Timestamps: (00:00) Intro (02:43) Getting involved in Stripe (05:37) Evaluating success in product marketing (06:35) The 3 pillars of Stripe's approach to brand (12:10) Managing resource allocation as Stripe grew (17:22) How Stripe scaled taste (21:30) Were Stripe reviews micromanaging? (24:16) Marketing under founders with strong marketing skills (26:44) Advice for early marketing hires (31:52) Marketing at Retool vs Stripe (33:59) Marketing to mid-market vs SMB vs enterprise (37:02) Marketing programs that had an outsized impact (39:59) Marketing horizontal vs vertical products (43:20) Lessons from OpenAI (52:22) Inside OpenAI’s recent website relaunch (55:57) How OpenAI’s marketers use OpenAI tooling (59:53) When to start hiring marketers (61:34) How to screen early marketing hires (66:39) The biggest influences on Krithika's career (67:52) Outro Thu, 01 Aug 2024 11:00:00 -0000 Inside marketing at Stripe, OpenAI and Retool | Krithika Muthukumar (VP of Marketing at OpenAI, ex-Stripe, Retool, Dropbox, Google) full First Round Krithika Muthukumar is a marketing veteran. She is currently the VP of Marketing at OpenAI where she was the first marketing hire. Before that, she was Head of Marketing at Retool. Her longest tenure was at Stripe where she was hired as the first marketer and scaled with the company over nine years, from a 60-person team to 7500+. She began her career in Product Marketing at Google and Dropbox. Krithika Muthukumar is a marketing veteran. She is currently the VP of Marketing at OpenAI where she was the first marketing hire. Before that, she was Head of Marketing at Retool. Her longest tenure was at Stripe where she was hired as the first marketer and scaled with the company over nine years, from a 60-person team to 7500+. She began her career in Product Marketing at Google and Dropbox. – In today’s episode, we discuss: Marketing lessons from OpenAI, Stripe, and Retool The 3 pillars of Stripe’s approach to brand How to manage resource allocation as a marketer Adapting marketing strategy to different business models Advice for early marketing hires – Referenced: Coca-Cola AI-generated wish card campaign: https://theprint.in/ani-press-releases/coca-cola-ignites-diwali-celebrations-with-unique-personalized-ai-generated-wish-cards/1840093/ Cristina Cordova: https://www.linkedin.com/in/cristinajcordova/ Gong: https://www.gong.io/ Greg Brockman: https://www.linkedin.com/in/thegdb/ Kenzo Fong: https://www.linkedin.com/in/kenzofong/ Retool: https://retool.com/ Stripe’s “Capture the Flag” campaign: https://techcrunch.com/2012/08/22/stripes-capture-the-flag-2-0-a-hands-on-contest-for-app-developers-to-test-their-security-know-how/ Stripe Press: https://press.stripe.com/ Stripe Sigma: https://stripe.com/us/sigma Tanya Khakbaz: https://www.linkedin.com/in/tanya-khakbaz-a725732/ – Where to find Krithika Muthukumar: LinkedIn: https://www.linkedin.com/in/krithix/ Twitter/X: https://x.com/krithix – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Timestamps: (00:00) Intro (02:43) Getting involved in Stripe (05:37) Evaluating success in product marketing (06:35) The 3 pillars of Stripe's approach to brand (12:10) Managing resource allocation as Stripe grew (17:22) How Stripe scaled taste (21:30) Were Stripe reviews micromanaging? (24:16) Marketing under founders with strong marketing skills (26:44) Advice for early marketing hires (31:52) Marketing at Retool vs Stripe (33:59) Marketing to mid-market vs SMB vs enterprise (37:02) Marketing programs that had an outsized impact (39:59) Marketing horizontal vs vertical products (43:20) Lessons from OpenAI (52:22) Inside OpenAI’s recent website relaunch (55:57) How OpenAI’s marketers use OpenAI tooling (59:53) When to start hiring marketers (61:34) How to screen early marketing hires (66:39) The biggest influences on Krithika's career (67:52) Outro Krithika Muthukumar is a marketing veteran. She is currently the VP of Marketing at OpenAI where she was the first marketing hire. Before that, she was Head of Marketing at Retool. Her longest tenure was at Stripe where she was hired as the first marketer and scaled with the company over nine years, from a 60-person team to 7500+. She began her career in Product Marketing at Google and Dropbox.

–

In today’s episode, we discuss:

  • Marketing lessons from OpenAI, Stripe, and Retool
  • The 3 pillars of Stripe’s approach to brand
  • How to manage resource allocation as a marketer
  • Adapting marketing strategy to different business models
  • Advice for early marketing hires

–

Referenced:

–

Where to find Krithika Muthukumar:

–

Where to find Brett Berson:

–

Timestamps:

(00:00) Intro

(02:43) Getting involved in Stripe

(05:37) Evaluating success in product marketing

(06:35) The 3 pillars of Stripe's approach to brand

(12:10) Managing resource allocation as Stripe grew

(17:22) How Stripe scaled taste

(21:30) Were Stripe reviews micromanaging?

(24:16) Marketing under founders with strong marketing skills

(26:44) Advice for early marketing hires

(31:52) Marketing at Retool vs Stripe

(33:59) Marketing to mid-market vs SMB vs enterprise

(37:02) Marketing programs that had an outsized impact

(39:59) Marketing horizontal vs vertical products

(43:20) Lessons from OpenAI

(52:22) Inside OpenAI’s recent website relaunch

(55:57) How OpenAI’s marketers use OpenAI tooling

(59:53) When to start hiring marketers

(61:34) How to screen early marketing hires

(66:39) The biggest influences on Krithika's career

(67:52) Outro

]]> 4084 Developing technical taste: A guide for next-gen engineers | Sam Schillace (Deputy CTO at Microsoft, creator of Google Docs) Sam Schillace is the CVP and Deputy CTO at Microsoft. Before Microsoft, Sam held prominent engineering roles at Google and Box. He has also founded six startups, including Writely, which was acquired by Google and became Google Docs. – In today’s episode, we discuss: Sam’s advice for future engineers What’s next for AI How to develop technical taste The importance of asking “what if” questions Lessons on market timing Scaling a software company in 2024 – Referenced: Amazon: https://amazon.com Box: https://www.box.com/ Elon Musk: https://twitter.com/elonmusk Google Docs: https://docs.google.com Itzhak Perlman: https://itzhakperlman.com/ Microsoft: https://www.microsoft.com Netflix: https://www.netflix.com Tesla: https://www.tesla.com/ The Innovator’s Dilemma: https://www.amazon.com.au/Innovators-Dilemma-Clayton-M-Christensen/dp/0062060244 TurboTax: https://turbotax.intuit.com/ Uber: https://www.uber.com/ Walmart: https://www.walmart.com/ Workday: https://www.workday.com/ Writely: https://techcrunch.com/2005/08/31/writely-process-words-with-your-browser/ – Where to find Sam Schillace: LinkedIn: https://www.linkedin.com/in/schillace/ Newsletter: https://sundaylettersfromsam.substack.com/ Twitter/X: https://twitter.com/sschillace – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Introduction (02:54) Lessons on market timing (07:30) Developing technical taste (09:51) Asking “what if” questions (14:03) Building Google Docs (19:32) The decline of Google apps (20:57) The Innovator’s Dilemma facing Microsoft (22:53) The differences between Google and Microsoft (24:42) How to build a winning product (27:46) Becoming an optimist (29:12) Why engineering teams aren’t smaller (32:00) Sam’s prediction about AI (34:11) Capturing the value of AI (37:43) How you should think about AI (45:33) Advice for future engineers (48:18) What makes a great engineer (49:45) One thing the best engineers do (51:37) Microsoft’s new leverage (56:01) Scaling software in 2024 (59:50) The future of AI across several sectors (64:28) What Sam and a violinist have in common Thu, 06 Jun 2024 11:00:00 -0000 Developing technical taste: A guide for next-gen engineers | Sam Schillace (Deputy CTO at Microsoft, creator of Google Docs) full First Round Sam Schillace is the CVP and Deputy CTO at Microsoft. Before Microsoft, Sam held prominent engineering roles at Google and Box. He has also founded six startups, including Writely, which was acquired by Google and became Google Docs. Sam Schillace is the CVP and Deputy CTO at Microsoft. Before Microsoft, Sam held prominent engineering roles at Google and Box. He has also founded six startups, including Writely, which was acquired by Google and became Google Docs. – In today’s episode, we discuss: Sam’s advice for future engineers What’s next for AI How to develop technical taste The importance of asking “what if” questions Lessons on market timing Scaling a software company in 2024 – Referenced: Amazon: https://amazon.com Box: https://www.box.com/ Elon Musk: https://twitter.com/elonmusk Google Docs: https://docs.google.com Itzhak Perlman: https://itzhakperlman.com/ Microsoft: https://www.microsoft.com Netflix: https://www.netflix.com Tesla: https://www.tesla.com/ The Innovator’s Dilemma: https://www.amazon.com.au/Innovators-Dilemma-Clayton-M-Christensen/dp/0062060244 TurboTax: https://turbotax.intuit.com/ Uber: https://www.uber.com/ Walmart: https://www.walmart.com/ Workday: https://www.workday.com/ Writely: https://techcrunch.com/2005/08/31/writely-process-words-with-your-browser/ – Where to find Sam Schillace: LinkedIn: https://www.linkedin.com/in/schillace/ Newsletter: https://sundaylettersfromsam.substack.com/ Twitter/X: https://twitter.com/sschillace – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Introduction (02:54) Lessons on market timing (07:30) Developing technical taste (09:51) Asking “what if” questions (14:03) Building Google Docs (19:32) The decline of Google apps (20:57) The Innovator’s Dilemma facing Microsoft (22:53) The differences between Google and Microsoft (24:42) How to build a winning product (27:46) Becoming an optimist (29:12) Why engineering teams aren’t smaller (32:00) Sam’s prediction about AI (34:11) Capturing the value of AI (37:43) How you should think about AI (45:33) Advice for future engineers (48:18) What makes a great engineer (49:45) One thing the best engineers do (51:37) Microsoft’s new leverage (56:01) Scaling software in 2024 (59:50) The future of AI across several sectors (64:28) What Sam and a violinist have in common Sam Schillace is the CVP and Deputy CTO at Microsoft. Before Microsoft, Sam held prominent engineering roles at Google and Box. He has also founded six startups, including Writely, which was acquired by Google and became Google Docs.

–

In today’s episode, we discuss:

  • Sam’s advice for future engineers
  • What’s next for AI
  • How to develop technical taste
  • The importance of asking “what if” questions
  • Lessons on market timing
  • Scaling a software company in 2024

–

Referenced:

–

Where to find Sam Schillace:

–

Where to find Brett Berson:

–

Where to find First Round Capital:

–

Timestamps:

(00:00) Introduction

(02:54) Lessons on market timing

(07:30) Developing technical taste

(09:51) Asking “what if” questions

(14:03) Building Google Docs

(19:32) The decline of Google apps

(20:57) The Innovator’s Dilemma facing Microsoft

(22:53) The differences between Google and Microsoft

(24:42) How to build a winning product

(27:46) Becoming an optimist

(29:12) Why engineering teams aren’t smaller

(32:00) Sam’s prediction about AI

(34:11) Capturing the value of AI

(37:43) How you should think about AI

(45:33) Advice for future engineers

(48:18) What makes a great engineer

(49:45) One thing the best engineers do

(51:37) Microsoft’s new leverage

(56:01) Scaling software in 2024

(59:50) The future of AI across several sectors

(64:28) What Sam and a violinist have in common

]]> 3926 How to build and scale winning marketplaces | Casey Winters (Eventbrite, Pinterest, Grubhub) Casey Winters is a legendary advisor on scaling, product and growth. He’s worked with companies like Airbnb, Faire, Canva, Whatnot, Thumbtack, Tinder, and Reddit. Until recently, Casey was the Chief Product Officer at Eventbrite, and has also led growth and product teams at Pinterest and Grubhub. – In today’s episode, we discuss: What every marketplace founder should think about Why marketplaces are different Finding product market fit Key ingredients to scaling a marketplace Strategies for acquiring demand and supply – Referenced: Airbnb: https://airbnb.com/ Bill Gurley: https://www.linkedin.com/in/billgurley/ Blue Apron: https://www.blueapron.com/ Booking.com: https://www.booking.com/ DoorDash: https://www.doordash.com/ eBay: https://ebay.com/ Eventbrite: https://www.eventbrite.com/ Expedia: https://www.expedia.com/ Faire: https://www.faire.com/ Fermat Commerce: https://www.fermatcommerce.com/ Grubhub: https://www.grubhub.com/ Lyft: https://www.lyft.com/ Pinterest: https://www.pinterest.com/ Postmates: https://postmates.com/ Shopify: https://www.shopify.com/ Simon Rothman: https://www.linkedin.com/in/simonrothman/ Square: https://squareup.com/ Tony Xu: https://www.linkedin.com/in/xutony/ Turo: https://turo.com/ Uber: https://www.uber.com/ Zillow: https://www.zillow.com/ – Where to find Casey Winters LinkedIn: https://www.linkedin.com/in/caseywinters/ Twitter/X: https://twitter.com/onecaseman Website: https://caseyaccidental.com/ – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Introduction (02:30) Ingredients for a successful marketplace (05:34) Creating scalable growth loops (08:42) Emerging marketplaces in 2024 (10:56) 2 ways to acquire supply and demand (15:39) What’s unique about building a marketplace (18:27) When to focus on the demand side (23:10) Who to hire (26:22) Finding sticky customers (26:27) What Grubhub should’ve done (30:19) Uber versus Lyft (34:23) One thing all marketplace founders should know (34:45) Finding product market fit (40:45) Single versus multi-category marketplaces (43:02) When to expand (44:22) The best low-frequency marketplace (46:00) The product is supply, not software (50:48) No value in car-sharing (56:11) Improving supply and demand over time (61:04) The “setup, aha, and habit” framework (66:27) Avoid these marketplace mistakes (71:16) 2 people who influenced Casey’s thinking Thu, 30 May 2024 11:00:00 -0000 full First Round Casey Winters is a legendary advisor on scaling, product and growth. He’s worked with companies like Airbnb, Faire, Canva, Whatnot, Thumbtack, Tinder, and Reddit. Until recently, Casey was the Chief Product Officer at Eventbrite, and has also led growth and product teams at Pinterest and Grubhub. Casey Winters is a legendary advisor on scaling, product and growth. He’s worked with companies like Airbnb, Faire, Canva, Whatnot, Thumbtack, Tinder, and Reddit. Until recently, Casey was the Chief Product Officer at Eventbrite, and has also led growth and product teams at Pinterest and Grubhub. – In today’s episode, we discuss: What every marketplace founder should think about Why marketplaces are different Finding product market fit Key ingredients to scaling a marketplace Strategies for acquiring demand and supply – Referenced: Airbnb: https://airbnb.com/ Bill Gurley: https://www.linkedin.com/in/billgurley/ Blue Apron: https://www.blueapron.com/ Booking.com: https://www.booking.com/ DoorDash: https://www.doordash.com/ eBay: https://ebay.com/ Eventbrite: https://www.eventbrite.com/ Expedia: https://www.expedia.com/ Faire: https://www.faire.com/ Fermat Commerce: https://www.fermatcommerce.com/ Grubhub: https://www.grubhub.com/ Lyft: https://www.lyft.com/ Pinterest: https://www.pinterest.com/ Postmates: https://postmates.com/ Shopify: https://www.shopify.com/ Simon Rothman: https://www.linkedin.com/in/simonrothman/ Square: https://squareup.com/ Tony Xu: https://www.linkedin.com/in/xutony/ Turo: https://turo.com/ Uber: https://www.uber.com/ Zillow: https://www.zillow.com/ – Where to find Casey Winters LinkedIn: https://www.linkedin.com/in/caseywinters/ Twitter/X: https://twitter.com/onecaseman Website: https://caseyaccidental.com/ – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Introduction (02:30) Ingredients for a successful marketplace (05:34) Creating scalable growth loops (08:42) Emerging marketplaces in 2024 (10:56) 2 ways to acquire supply and demand (15:39) What’s unique about building a marketplace (18:27) When to focus on the demand side (23:10) Who to hire (26:22) Finding sticky customers (26:27) What Grubhub should’ve done (30:19) Uber versus Lyft (34:23) One thing all marketplace founders should know (34:45) Finding product market fit (40:45) Single versus multi-category marketplaces (43:02) When to expand (44:22) The best low-frequency marketplace (46:00) The product is supply, not software (50:48) No value in car-sharing (56:11) Improving supply and demand over time (61:04) The “setup, aha, and habit” framework (66:27) Avoid these marketplace mistakes (71:16) 2 people who influenced Casey’s thinking Casey Winters is a legendary advisor on scaling, product and growth. He’s worked with companies like Airbnb, Faire, Canva, Whatnot, Thumbtack, Tinder, and Reddit. Until recently, Casey was the Chief Product Officer at Eventbrite, and has also led growth and product teams at Pinterest and Grubhub.

–

In today’s episode, we discuss:

  • What every marketplace founder should think about
  • Why marketplaces are different
  • Finding product market fit
  • Key ingredients to scaling a marketplace
  • Strategies for acquiring demand and supply

–

Referenced:

–

Where to find Casey Winters

–

Where to find Brett Berson:

–

Where to find First Round Capital:

–

Timestamps:

(00:00) Introduction

(02:30) Ingredients for a successful marketplace

(05:34) Creating scalable growth loops

(08:42) Emerging marketplaces in 2024

(10:56) 2 ways to acquire supply and demand

(15:39) What’s unique about building a marketplace

(18:27) When to focus on the demand side

(23:10) Who to hire

(26:22) Finding sticky customers

(26:27) What Grubhub should’ve done

(30:19) Uber versus Lyft

(34:23) One thing all marketplace founders should know

(34:45) Finding product market fit

(40:45) Single versus multi-category marketplaces

(43:02) When to expand

(44:22) The best low-frequency marketplace

(46:00) The product is supply, not software

(50:48) No value in car-sharing

(56:11) Improving supply and demand over time

(61:04) The “setup, aha, and habit” framework

(66:27) Avoid these marketplace mistakes

(71:16) 2 people who influenced Casey’s thinking

]]> 4409 Lessons from Sentry on scaling DevTools and finding product market fit (again) | Milin Desai (Sentry, VMware, Riverbed) Milin Desai is the CEO at Sentry, an application monitoring tool for developers. Sentry has recently passed two key milestones: 100K customers and over $100M in ARR. Before Sentry, Milin was a GM at VMware and scaled their cloud networking into a billion-dollar business. Prior to stepping into leadership roles, Milin was a PM at Riverbed and a software engineer at Veritas. — In today’s episode, we discuss: The key ingredients of Sentry’s success Sentry’s developer-centric approach Lessons on pricing, packaging, and product from VMware Being an external CEO at a startup Forging successful relationships with founders — Referenced: Building for the Fortune 500,000: https://blog.sentry.io/building-for-the-fortune-500-000/ Carl Eschenbach: https://www.linkedin.com/in/carl-eschenbach-980543/ Chris Jennings: https://www.linkedin.com/in/chriskjennings/ David Cramer: https://www.linkedin.com/in/dmcramer/ FRC’s product market fit framework: https://pmf.firstround.com/ Martin Casado: https://www.linkedin.com/in/martincasado/ Pat Gelsinger: https://www.linkedin.com/in/patgelsinger/ Raghu Raghuram: https://www.linkedin.com/in/raghuraghuram/ Riverbed: https://www.riverbed.com/ Sentry: https://sentry.io/ Todd Bazakas: https://www.linkedin.com/in/todd-bazakas-b5a2533/ Veritas: https://www.veritas.com/ VMware: https://www.vmware.com/ — Where to find Milin Desai: LinkedIn: https://www.linkedin.com/in/milin-desai-464757/ Twitter/X: https://twitter.com/virtualmilin — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (03:03) Joining Sentry as an external CEO (06:27) The CEO/founder relationship (09:37) Lessons from VMware (13:04) What PMs did differently at VMware (18:04) Becoming the need, not the want (20:53) Scaling Sentry (23:07) Building for the “Fortune 500,000” (27:02) Open versus closed source product (30:43) The key ingredients to Sentry’s success (36:21) How Milin updated his playbook at Sentry (38:49) Focus on packaging, not pricing (40:29) “Build for the many, not the few” (41:53) Sentry’s B2D model (45:10) The second product mindset (51:03) Contrarian take on building for enterprise (52:50) Several people who influenced Milin Thu, 16 May 2024 11:00:00 -0000 Lessons from Sentry on scaling DevTools and finding product market fit (again) | Milin Desai (Sentry, VMware, Riverbed) full First Round Milin Desai is the CEO at Sentry, an application monitoring tool for developers. Sentry has recently passed two key milestones: 100K customers and over $100M in ARR. Before Sentry, Milin was a GM at VMware and scaled their cloud networking into a billion-dollar business. Prior to stepping into leadership roles, Milin was a PM at Riverbed and a software engineer at Veritas. Milin Desai is the CEO at Sentry, an application monitoring tool for developers. Sentry has recently passed two key milestones: 100K customers and over $100M in ARR. Before Sentry, Milin was a GM at VMware and scaled their cloud networking into a billion-dollar business. Prior to stepping into leadership roles, Milin was a PM at Riverbed and a software engineer at Veritas. — In today’s episode, we discuss: The key ingredients of Sentry’s success Sentry’s developer-centric approach Lessons on pricing, packaging, and product from VMware Being an external CEO at a startup Forging successful relationships with founders — Referenced: Building for the Fortune 500,000: https://blog.sentry.io/building-for-the-fortune-500-000/ Carl Eschenbach: https://www.linkedin.com/in/carl-eschenbach-980543/ Chris Jennings: https://www.linkedin.com/in/chriskjennings/ David Cramer: https://www.linkedin.com/in/dmcramer/ FRC’s product market fit framework: https://pmf.firstround.com/ Martin Casado: https://www.linkedin.com/in/martincasado/ Pat Gelsinger: https://www.linkedin.com/in/patgelsinger/ Raghu Raghuram: https://www.linkedin.com/in/raghuraghuram/ Riverbed: https://www.riverbed.com/ Sentry: https://sentry.io/ Todd Bazakas: https://www.linkedin.com/in/todd-bazakas-b5a2533/ Veritas: https://www.veritas.com/ VMware: https://www.vmware.com/ — Where to find Milin Desai: LinkedIn: https://www.linkedin.com/in/milin-desai-464757/ Twitter/X: https://twitter.com/virtualmilin — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (03:03) Joining Sentry as an external CEO (06:27) The CEO/founder relationship (09:37) Lessons from VMware (13:04) What PMs did differently at VMware (18:04) Becoming the need, not the want (20:53) Scaling Sentry (23:07) Building for the “Fortune 500,000” (27:02) Open versus closed source product (30:43) The key ingredients to Sentry’s success (36:21) How Milin updated his playbook at Sentry (38:49) Focus on packaging, not pricing (40:29) “Build for the many, not the few” (41:53) Sentry’s B2D model (45:10) The second product mindset (51:03) Contrarian take on building for enterprise (52:50) Several people who influenced Milin Milin Desai is the CEO at Sentry, an application monitoring tool for developers. Sentry has recently passed two key milestones: 100K customers and over $100M in ARR. Before Sentry, Milin was a GM at VMware and scaled their cloud networking into a billion-dollar business. Prior to stepping into leadership roles, Milin was a PM at Riverbed and a software engineer at Veritas.

—

In today’s episode, we discuss:

  • The key ingredients of Sentry’s success
  • Sentry’s developer-centric approach
  • Lessons on pricing, packaging, and product from VMware
  • Being an external CEO at a startup
  • Forging successful relationships with founders

—

Referenced:

—

Where to find Milin Desai:

—

Where to find Brett Berson:

—

Where to find First Round Capital:

—

Timestamps:

(00:00) Introduction

(03:03) Joining Sentry as an external CEO

(06:27) The CEO/founder relationship

(09:37) Lessons from VMware

(13:04) What PMs did differently at VMware

(18:04) Becoming the need, not the want

(20:53) Scaling Sentry

(23:07) Building for the “Fortune 500,000”

(27:02) Open versus closed source product

(30:43) The key ingredients to Sentry’s success

(36:21) How Milin updated his playbook at Sentry

(38:49) Focus on packaging, not pricing

(40:29) “Build for the many, not the few”

(41:53) Sentry’s B2D model

(45:10) The second product mindset

(51:03) Contrarian take on building for enterprise

(52:50) Several people who influenced Milin

]]> 3481 How to be effective up and down the org chart | Matt MacInnis (Rippling, Inkling, Apple) Matt MacInnis is the COO at Rippling, an all-in-one HR, IT, and finance platform for businesses, which last raised $500M at a $11.25B valuation. Before Rippling, Matt was the co-founder and CEO at Inkling, a mobile learning platform that was acquired in 2018. He also held several management roles at Apple. — In today’s episode, we discuss: Lessons on culture, org-design, and product from Rippling Characteristics of great CEOs How to a better executive leader Leading with kindness and impatience How to fight entropy — Referenced: Andy Roddick: https://www.atptour.com/en/players/andy-roddick/r485/overview Apple: https://www.apple.com Bain & Company: https://www.bain.com/ Bill Campbell: https://en.wikipedia.org/wiki/Bill_Campbell_(business_executive) Conscious Business: https://www.amazon.com.au/Conscious-Business-Build-Value-Through/dp/1622032020 Google: https://www.google.com Inkling: https://www.inkling.com/ McCaw Cellular: https://en.wikipedia.org/wiki/McCaw_Cellular_Communications McKinsey: https://www.mckinsey.com/ Microsoft: https://www.microsoft.com Oracle: https://www.oracle.com Parker Conrad: https://www.linkedin.com/in/parkerconrad/ Peter Currie: https://en.wikipedia.org/wiki/Peter_Currie_(businessman) Rippling: https://www.rippling.com The Effective Executive: https://www.amazon.com.au/Effective-Executive-Peter-Ferdinand-Drucker/dp/0060833459 — Where to find Matt MacInnis: LinkedIn: https://www.linkedin.com/in/macinnis/ Twitter/X: https://twitter.com/stanine — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:14) Great CEOs don’t worry about their weaknesses (06:31) The third-time founder mindset (08:09) Why every great CEO is impatient (11:54) How executives fight entropy (19:11) Experience ≠ wisdom (21:26) Managing workplace politics (24:02) Why all businesses should dogfood (26:20) Overseeing employee expenses (27:43) The best CEOs don’t need coaching (29:55) The hidden cost of advice (40:40) Why execs are “tortured but happy” (44:16) Clear versus first principles thinking (51:09) Finding first principles thinkers (53:13) Why people overcomplicate culture (55:53) Don’t make this mistake when interviewing (59:26) The importance of anti-patterns (61:27) Important business values (63:28) How Matt thinks about output (66:33) Rippling’s key leadership principle (71:02) Why kindness matters (72:03) Freeing yourself from self-doubt Thu, 25 Apr 2024 11:00:00 -0000 How to be effective up and down the org chart | Matt MacInnis (Rippling, Inkling, Apple) full First Round Matt MacInnis is the COO at Rippling, an all-in-one HR, IT, and finance platform for businesses, which last raised $500M at a $11.25B valuation. Before Rippling, Matt was the co-founder and CEO at Inkling, a mobile learning platform that was acquired in 2018. He also held several management roles at Apple. Matt MacInnis is the COO at Rippling, an all-in-one HR, IT, and finance platform for businesses, which last raised $500M at a $11.25B valuation. Before Rippling, Matt was the co-founder and CEO at Inkling, a mobile learning platform that was acquired in 2018. He also held several management roles at Apple. — In today’s episode, we discuss: Lessons on culture, org-design, and product from Rippling Characteristics of great CEOs How to a better executive leader Leading with kindness and impatience How to fight entropy — Referenced: Andy Roddick: https://www.atptour.com/en/players/andy-roddick/r485/overview Apple: https://www.apple.com Bain & Company: https://www.bain.com/ Bill Campbell: https://en.wikipedia.org/wiki/Bill_Campbell_(business_executive) Conscious Business: https://www.amazon.com.au/Conscious-Business-Build-Value-Through/dp/1622032020 Google: https://www.google.com Inkling: https://www.inkling.com/ McCaw Cellular: https://en.wikipedia.org/wiki/McCaw_Cellular_Communications McKinsey: https://www.mckinsey.com/ Microsoft: https://www.microsoft.com Oracle: https://www.oracle.com Parker Conrad: https://www.linkedin.com/in/parkerconrad/ Peter Currie: https://en.wikipedia.org/wiki/Peter_Currie_(businessman) Rippling: https://www.rippling.com The Effective Executive: https://www.amazon.com.au/Effective-Executive-Peter-Ferdinand-Drucker/dp/0060833459 — Where to find Matt MacInnis: LinkedIn: https://www.linkedin.com/in/macinnis/ Twitter/X: https://twitter.com/stanine — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:14) Great CEOs don’t worry about their weaknesses (06:31) The third-time founder mindset (08:09) Why every great CEO is impatient (11:54) How executives fight entropy (19:11) Experience ≠ wisdom (21:26) Managing workplace politics (24:02) Why all businesses should dogfood (26:20) Overseeing employee expenses (27:43) The best CEOs don’t need coaching (29:55) The hidden cost of advice (40:40) Why execs are “tortured but happy” (44:16) Clear versus first principles thinking (51:09) Finding first principles thinkers (53:13) Why people overcomplicate culture (55:53) Don’t make this mistake when interviewing (59:26) The importance of anti-patterns (61:27) Important business values (63:28) How Matt thinks about output (66:33) Rippling’s key leadership principle (71:02) Why kindness matters (72:03) Freeing yourself from self-doubt Matt MacInnis is the COO at Rippling, an all-in-one HR, IT, and finance platform for businesses, which last raised $500M at a $11.25B valuation. Before Rippling, Matt was the co-founder and CEO at Inkling, a mobile learning platform that was acquired in 2018. He also held several management roles at Apple.

—

In today’s episode, we discuss:

  • Lessons on culture, org-design, and product from Rippling
  • Characteristics of great CEOs
  • How to a better executive leader
  • Leading with kindness and impatience
  • How to fight entropy

—

Referenced:

—

Where to find Matt MacInnis:

—

Where to find Brett Berson:

—

Where to find First Round Capital:

—

Timestamps:

(00:00) Introduction

(02:14) Great CEOs don’t worry about their weaknesses

(06:31) The third-time founder mindset

(08:09) Why every great CEO is impatient

(11:54) How executives fight entropy

(19:11) Experience ≠ wisdom

(21:26) Managing workplace politics

(24:02) Why all businesses should dogfood

(26:20) Overseeing employee expenses

(27:43) The best CEOs don’t need coaching

(29:55) The hidden cost of advice

(40:40) Why execs are “tortured but happy”

(44:16) Clear versus first principles thinking

(51:09) Finding first principles thinkers

(53:13) Why people overcomplicate culture

(55:53) Don’t make this mistake when interviewing

(59:26) The importance of anti-patterns

(61:27) Important business values

(63:28) How Matt thinks about output

(66:33) Rippling’s key leadership principle

(71:02) Why kindness matters

(72:03) Freeing yourself from self-doubt

]]> 4540 Timeless lessons on running software companies that endure | Alyssa Henry (Square, Amazon, Microsoft) Alyssa Henry is the former CEO of Square, a financial services company providing products and services used by over 4 million merchants. Formerly at Amazon, Alyssa led the development and growth of Simple Storage Service (S3) at AWS. Alyssa now serves as an Independent Director at Intel and Confluent. —  In today’s episode, we discuss: Lessons from Amazon, Microsoft, and Square “Minimum Remarkable Products” versus Minimum Viable Products Navigating different work cultures in big tech Insider reactions to the disruptive launch of AWS “Pioneer” versus “fast-follower” companies —  Referenced: Amazon: https://www.amazon.com Amazon Web Services: https://aws.amazon.com Bill Gates: https://www.linkedin.com/in/williamhgates Block, Inc: https://block.xyz Cash App: https://cash.app Fast Company - Back To Square One: https://www.fastcompany.com/3033412/back-to-square-one Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1 Jack Dorsey: https://twitter.com/Jack James Hamilton: https://www.linkedin.com/in/jameshamilton4 Jeff Bezos: https://twitter.com/jeffbezos Microsoft: https://www.microsoft.com Oracle Corporation: https://www.oracle.com Sarah Friar: https://www.linkedin.com/in/sarah-friar Square: https://squareup.com Tom Szkutak: https://www.linkedin.com/in/tom-szkutak-4b59817 WSJ - Mobile-Payments Startup Square Discusses Possible Sale: https://www.wsj.com/articles/SB10001424052702303825604579513882989476424 —  Where to find Alyssa Henry: LinkedIn: https://linkedin.com/in/alyssa-henry-0905692 Twitter/X: https://twitter.com/alyssahhenry —  Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson —  Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast —  Timestamps: (00:00) Introduction (02:20) Lessons from Microsoft and Amazon (08:29) Noticeable consistencies in the human condition (10:50) Differences in culture at Amazon, Microsoft and Square (13:27) Why “customers come first,” even above employees and community (14:01) Why fast-followers can be less customer-focused (15:50) The challenge of commercializing research projects (18:58) Joining Square and “building a picture” of the org (24:55) Knowing what to replicate from past companies (27:45) Questioning norms in new companies (28:41) The importance of effective communication systems (31:31) How to operationalize company values (33:38) Why shared beliefs are crucial for good company culture (37:05) Building Minimal Remarkable Products at Square (38:13) How to scale an aesthetic (42:46) Org design lessons from Square (50:06) How to align different teams behind business priorities (52:57) Lessons learned from fierce competition (57:39) The “fast follower” vs “pioneer” playbook (61:05) The original thinking behind AWS (66:08) The unlikely origin of Amazon CloudFront and other products (73:47) How Jeff Bezos influenced Alyssa Thu, 18 Apr 2024 11:00:00 -0000 Timeless lessons on running software companies that endure | Alyssa Henry (Square, Amazon, Microsoft) full First Round Alyssa Henry is the former CEO of Square, a financial services company providing products and services used by over 4 million merchants. Formerly at Amazon, Alyssa led the development and growth of Simple Storage Service (S3) at AWS. Alyssa now serves as an Independent Director at Intel and Confluent. Alyssa Henry is the former CEO of Square, a financial services company providing products and services used by over 4 million merchants. Formerly at Amazon, Alyssa led the development and growth of Simple Storage Service (S3) at AWS. Alyssa now serves as an Independent Director at Intel and Confluent. —  In today’s episode, we discuss: Lessons from Amazon, Microsoft, and Square “Minimum Remarkable Products” versus Minimum Viable Products Navigating different work cultures in big tech Insider reactions to the disruptive launch of AWS “Pioneer” versus “fast-follower” companies —  Referenced: Amazon: https://www.amazon.com Amazon Web Services: https://aws.amazon.com Bill Gates: https://www.linkedin.com/in/williamhgates Block, Inc: https://block.xyz Cash App: https://cash.app Fast Company - Back To Square One: https://www.fastcompany.com/3033412/back-to-square-one Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1 Jack Dorsey: https://twitter.com/Jack James Hamilton: https://www.linkedin.com/in/jameshamilton4 Jeff Bezos: https://twitter.com/jeffbezos Microsoft: https://www.microsoft.com Oracle Corporation: https://www.oracle.com Sarah Friar: https://www.linkedin.com/in/sarah-friar Square: https://squareup.com Tom Szkutak: https://www.linkedin.com/in/tom-szkutak-4b59817 WSJ - Mobile-Payments Startup Square Discusses Possible Sale: https://www.wsj.com/articles/SB10001424052702303825604579513882989476424 —  Where to find Alyssa Henry: LinkedIn: https://linkedin.com/in/alyssa-henry-0905692 Twitter/X: https://twitter.com/alyssahhenry —  Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson —  Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast —  Timestamps: (00:00) Introduction (02:20) Lessons from Microsoft and Amazon (08:29) Noticeable consistencies in the human condition (10:50) Differences in culture at Amazon, Microsoft and Square (13:27) Why “customers come first,” even above employees and community (14:01) Why fast-followers can be less customer-focused (15:50) The challenge of commercializing research projects (18:58) Joining Square and “building a picture” of the org (24:55) Knowing what to replicate from past companies (27:45) Questioning norms in new companies (28:41) The importance of effective communication systems (31:31) How to operationalize company values (33:38) Why shared beliefs are crucial for good company culture (37:05) Building Minimal Remarkable Products at Square (38:13) How to scale an aesthetic (42:46) Org design lessons from Square (50:06) How to align different teams behind business priorities (52:57) Lessons learned from fierce competition (57:39) The “fast follower” vs “pioneer” playbook (61:05) The original thinking behind AWS (66:08) The unlikely origin of Amazon CloudFront and other products (73:47) How Jeff Bezos influenced Alyssa Alyssa Henry is the former CEO of Square, a financial services company providing products and services used by over 4 million merchants. Formerly at Amazon, Alyssa led the development and growth of Simple Storage Service (S3) at AWS. Alyssa now serves as an Independent Director at Intel and Confluent.

— 

In today’s episode, we discuss:

  • Lessons from Amazon, Microsoft, and Square
  • “Minimum Remarkable Products” versus Minimum Viable Products
  • Navigating different work cultures in big tech
  • Insider reactions to the disruptive launch of AWS
  • “Pioneer” versus “fast-follower” companies

— 

Referenced:

— 

Where to find Alyssa Henry:

— 

Where to find Brett Berson:

— 

Where to find First Round Capital:

— 

Timestamps:

(00:00) Introduction

(02:20) Lessons from Microsoft and Amazon

(08:29) Noticeable consistencies in the human condition

(10:50) Differences in culture at Amazon, Microsoft and Square

(13:27) Why “customers come first,” even above employees and community

(14:01) Why fast-followers can be less customer-focused

(15:50) The challenge of commercializing research projects

(18:58) Joining Square and “building a picture” of the org

(24:55) Knowing what to replicate from past companies

(27:45) Questioning norms in new companies

(28:41) The importance of effective communication systems

(31:31) How to operationalize company values

(33:38) Why shared beliefs are crucial for good company culture

(37:05) Building Minimal Remarkable Products at Square

(38:13) How to scale an aesthetic

(42:46) Org design lessons from Square

(50:06) How to align different teams behind business priorities

(52:57) Lessons learned from fierce competition

(57:39) The “fast follower” vs “pioneer” playbook

(61:05) The original thinking behind AWS

(66:08) The unlikely origin of Amazon CloudFront and other products

(73:47) How Jeff Bezos influenced Alyssa

]]> 4615 Building products that delight customers | Adam Nash (Daffy, Wealthfront, LinkedIn, eBay, Apple) Adam Nash is the co-founder and CEO at Daffy, a platform that makes it easier to donate to charities and non-profits. Before Daffy, Adam was the President and CEO at Wealthfront, where he scaled the company’s assets under management from $100M to over $4B. Adam has also held leadership and technical roles at Dropbox, LinkedIn, eBay, and Apple. — In today’s episode, we discuss: Why founders should build platforms, not apps The importance of “delighting” customers How Daffy is disrupting donor-advised-funds Lessons on strategy from LinkedIn How to think about leadership transitions — Referenced: Andy Rachleff: https://www.linkedin.com/in/rachleff/ Bill Gates: https://www.linkedin.com/in/williamhgates/ Daffy: https://www.daffy.org/ Daffy’s 2023 Year in Review: https://www.daffy.org/resources/year-in-review-2023 eBay: https://www.ebay.com/ Jeff Weiner: https://www.linkedin.com/in/jeffweiner08/ Reid Hoffman: https://www.linkedin.com/in/reidhoffman/ Robinhood: https://robinhood.com/ Ryan Roslansky: https://www.linkedin.com/in/ryanroslansky/ The Innovator’s Dilemma: https://www.amazon.com/Innovators-Dilemma-Clayton-M-Christensen/dp/0062060244 Tim Cook: https://www.apple.com/leadership/tim-cook/ Wealthfront: https://www.wealthfront.com/ — Where to find Adam Nash: LinkedIn: https://www.linkedin.com/in/adamnash/ Twitter/X: https://twitter.com/adamnash — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:08) Why the last 10 years have been less disruptive (06:15) Why we think about luck wrong (08:39) How eBay survived the dot com bubble (14:37) The value of building platforms, not apps (22:18) What made LinkedIn successful (27:31) Good company strategy = good product strategy (30:58) Setting LinkedIn’s strategy in 2009 (36:41) Why KaChing didn’t work (40:56) Pivoting to Wealthfront (43:23) Universal lesson on customer acquisition (45:11) Treating growth like a product problem (49:01) Advice on successful leadership transitions (54:20) How to delegate moral authority (60:24) The problem with metrics and customer requests (66:41) Apple’s approach to “delighting” customers (69:16) The 70/20/10 rule you’ve never heard about (70:29) How Daffy ships “delight features” Thu, 04 Apr 2024 11:00:00 -0000 Building products that delight customers | Adam Nash (Daffy, Wealthfront, LinkedIn, eBay, Apple) full First Round Adam Nash is the co-founder and CEO at Daffy, a platform that makes it easier to donate to charities and non-profits. Before Daffy, Adam was the President and CEO at Wealthfront, where he scaled the company’s assets under management from $100M to over $4B. Adam has also held leadership and technical roles at Dropbox, LinkedIn, eBay, and Apple. Adam Nash is the co-founder and CEO at Daffy, a platform that makes it easier to donate to charities and non-profits. Before Daffy, Adam was the President and CEO at Wealthfront, where he scaled the company’s assets under management from $100M to over $4B. Adam has also held leadership and technical roles at Dropbox, LinkedIn, eBay, and Apple. — In today’s episode, we discuss: Why founders should build platforms, not apps The importance of “delighting” customers How Daffy is disrupting donor-advised-funds Lessons on strategy from LinkedIn How to think about leadership transitions — Referenced: Andy Rachleff: https://www.linkedin.com/in/rachleff/ Bill Gates: https://www.linkedin.com/in/williamhgates/ Daffy: https://www.daffy.org/ Daffy’s 2023 Year in Review: https://www.daffy.org/resources/year-in-review-2023 eBay: https://www.ebay.com/ Jeff Weiner: https://www.linkedin.com/in/jeffweiner08/ Reid Hoffman: https://www.linkedin.com/in/reidhoffman/ Robinhood: https://robinhood.com/ Ryan Roslansky: https://www.linkedin.com/in/ryanroslansky/ The Innovator’s Dilemma: https://www.amazon.com/Innovators-Dilemma-Clayton-M-Christensen/dp/0062060244 Tim Cook: https://www.apple.com/leadership/tim-cook/ Wealthfront: https://www.wealthfront.com/ — Where to find Adam Nash: LinkedIn: https://www.linkedin.com/in/adamnash/ Twitter/X: https://twitter.com/adamnash — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:08) Why the last 10 years have been less disruptive (06:15) Why we think about luck wrong (08:39) How eBay survived the dot com bubble (14:37) The value of building platforms, not apps (22:18) What made LinkedIn successful (27:31) Good company strategy = good product strategy (30:58) Setting LinkedIn’s strategy in 2009 (36:41) Why KaChing didn’t work (40:56) Pivoting to Wealthfront (43:23) Universal lesson on customer acquisition (45:11) Treating growth like a product problem (49:01) Advice on successful leadership transitions (54:20) How to delegate moral authority (60:24) The problem with metrics and customer requests (66:41) Apple’s approach to “delighting” customers (69:16) The 70/20/10 rule you’ve never heard about (70:29) How Daffy ships “delight features” Adam Nash is the co-founder and CEO at Daffy, a platform that makes it easier to donate to charities and non-profits. Before Daffy, Adam was the President and CEO at Wealthfront, where he scaled the company’s assets under management from $100M to over $4B. Adam has also held leadership and technical roles at Dropbox, LinkedIn, eBay, and Apple.

—

In today’s episode, we discuss:

  • Why founders should build platforms, not apps
  • The importance of “delighting” customers
  • How Daffy is disrupting donor-advised-funds
  • Lessons on strategy from LinkedIn
  • How to think about leadership transitions

—

Referenced:

—

Where to find Adam Nash:

—

Where to find Brett Berson:

—

Where to find First Round Capital:

—

Timestamps:

(00:00) Introduction

(02:08) Why the last 10 years have been less disruptive

(06:15) Why we think about luck wrong

(08:39) How eBay survived the dot com bubble

(14:37) The value of building platforms, not apps

(22:18) What made LinkedIn successful

(27:31) Good company strategy = good product strategy

(30:58) Setting LinkedIn’s strategy in 2009

(36:41) Why KaChing didn’t work

(40:56) Pivoting to Wealthfront

(43:23) Universal lesson on customer acquisition

(45:11) Treating growth like a product problem

(49:01) Advice on successful leadership transitions

(54:20) How to delegate moral authority

(60:24) The problem with metrics and customer requests

(66:41) Apple’s approach to “delighting” customers

(69:16) The 70/20/10 rule you’ve never heard about

(70:29) How Daffy ships “delight features”

]]> 4579 A masterclass in founder conviction | Eilon Reshef (Co-founder and CPO at Gong) Eilon Reshef is the co-founder and CPO at Gong, an AI-powered platform that tracks, records, and analyzes sales calls to drive revenue growth. In 2021, Gong raised $250M at a $7.25B valuation. Gong was one of the fastest SaaS companies to hit $100m ARR, and now has over 4000 customers. Before Gong, Eilon sold his previous e-commerce startup, Webcollage. — In today’s episode, we discuss: Why Eilon was so bullish on recording sales calls How Gong knew they had product market fit The importance of design partners Expanding into multi-product offerings Lessons from riding the AI wave since 2015 The future of AI in B2B sales efficiency — Referenced: Act-On Software: https://act-on.com/ Amit Bendov: https://www.linkedin.com/in/amitbendov/ BlueJeans: https://www.bluejeans.com/ Crossing the Chasm: https://www.amazon.com/Crossing-Chasm-3rd-Geoffrey-Moore/dp/0062292986 Gong: https://www.gong.io/ Mistral: https://mistral.ai/ OpenAI: https://openai.com/ Salesforce: https://salesforce.com/ Webcollage: https://www.crunchbase.com/organization/webcollage Webex: https://www.webex.com/ Zoom: https://zoom.us/ — Where to find Eilon Reshef: LinkedIn: https://www.linkedin.com/in/eilonreshef/ — Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:32) Eilon’s unwavering conviction in Gong (09:34) Initial reactions to Gong’s demo (13:48) Keeping the beta lean (15:33) Gong’s monetization strategy (16:38) Early signs of product market fit (18:14) The importance of design partners to Gong’s growth (21:52) Why VCs were afraid to invest (23:43) Reaching 100 customers (26:10) Eilon’s unique product roadmap framework (28:22) Going from $2M to $9M ARR in one year (29:02) The journey to multi-product (30:52) How Gong measures success (34:07) Lessons from building AI products for sales (37:45) Predicting the future of B2B sales (38:48) The concept of “raving fans” (39:31) Why it’s “easier” for second-time founders (42:00) Eilon’s favorite books (42:45) Gong in 2024 Thu, 28 Mar 2024 11:00:00 -0000 A masterclass in founder conviction | Eilon Reshef (Co-founder and CPO at Gong) full First Round Eilon Reshef is the co-founder and CPO at Gong, an AI-powered platform that tracks, records, and analyzes sales calls to drive revenue growth. In 2021, Gong raised $250M at a $7.25B valuation. Gong was one of the fastest SaaS companies to hit $100m ARR, and now has over 4000 customers. Before Gong, Eilon sold his previous e-commerce startup, Webcollage. Eilon Reshef is the co-founder and CPO at Gong, an AI-powered platform that tracks, records, and analyzes sales calls to drive revenue growth. In 2021, Gong raised $250M at a $7.25B valuation. Gong was one of the fastest SaaS companies to hit $100m ARR, and now has over 4000 customers. Before Gong, Eilon sold his previous e-commerce startup, Webcollage. — In today’s episode, we discuss: Why Eilon was so bullish on recording sales calls How Gong knew they had product market fit The importance of design partners Expanding into multi-product offerings Lessons from riding the AI wave since 2015 The future of AI in B2B sales efficiency — Referenced: Act-On Software: https://act-on.com/ Amit Bendov: https://www.linkedin.com/in/amitbendov/ BlueJeans: https://www.bluejeans.com/ Crossing the Chasm: https://www.amazon.com/Crossing-Chasm-3rd-Geoffrey-Moore/dp/0062292986 Gong: https://www.gong.io/ Mistral: https://mistral.ai/ OpenAI: https://openai.com/ Salesforce: https://salesforce.com/ Webcollage: https://www.crunchbase.com/organization/webcollage Webex: https://www.webex.com/ Zoom: https://zoom.us/ — Where to find Eilon Reshef: LinkedIn: https://www.linkedin.com/in/eilonreshef/ — Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:32) Eilon’s unwavering conviction in Gong (09:34) Initial reactions to Gong’s demo (13:48) Keeping the beta lean (15:33) Gong’s monetization strategy (16:38) Early signs of product market fit (18:14) The importance of design partners to Gong’s growth (21:52) Why VCs were afraid to invest (23:43) Reaching 100 customers (26:10) Eilon’s unique product roadmap framework (28:22) Going from $2M to $9M ARR in one year (29:02) The journey to multi-product (30:52) How Gong measures success (34:07) Lessons from building AI products for sales (37:45) Predicting the future of B2B sales (38:48) The concept of “raving fans” (39:31) Why it’s “easier” for second-time founders (42:00) Eilon’s favorite books (42:45) Gong in 2024 Eilon Reshef is the co-founder and CPO at Gong, an AI-powered platform that tracks, records, and analyzes sales calls to drive revenue growth. In 2021, Gong raised $250M at a $7.25B valuation. Gong was one of the fastest SaaS companies to hit $100m ARR, and now has over 4000 customers. Before Gong, Eilon sold his previous e-commerce startup, Webcollage.

—

In today’s episode, we discuss:

  • Why Eilon was so bullish on recording sales calls
  • How Gong knew they had product market fit
  • The importance of design partners
  • Expanding into multi-product offerings
  • Lessons from riding the AI wave since 2015
  • The future of AI in B2B sales efficiency

—

Referenced:

—

Where to find Eilon Reshef:

—

Where to find Todd Jackson:

—

Where to find First Round Capital:

—

Timestamps:

(00:00) Introduction

(02:32) Eilon’s unwavering conviction in Gong

(09:34) Initial reactions to Gong’s demo

(13:48) Keeping the beta lean

(15:33) Gong’s monetization strategy

(16:38) Early signs of product market fit

(18:14) The importance of design partners to Gong’s growth

(21:52) Why VCs were afraid to invest

(23:43) Reaching 100 customers

(26:10) Eilon’s unique product roadmap framework

(28:22) Going from $2M to $9M ARR in one year

(29:02) The journey to multi-product

(30:52) How Gong measures success

(34:07) Lessons from building AI products for sales

(37:45) Predicting the future of B2B sales

(38:48) The concept of “raving fans”

(39:31) Why it’s “easier” for second-time founders

(42:00) Eilon’s favorite books

(42:45) Gong in 2024

]]> 2629 Essential lessons for building and scaling DevTools | Dennis Pilarinos (Unblocked, Apple, Amazon, Buddybuild, Microsoft) Dennis Pilarinos is the founder and CEO at Unblocked, a developer tool that lets you talk to your codebase. In 2018, Dennis’ first company, Buddybuild, was acquired by Apple, and he was subsequently appointed Director of Development Technologies. Before that, Dennis was a Senior Director at AWS and a Director at Microsoft. — In today’s episode, we discuss: Lessons on culture and product from Amazon, Apple, and Microsoft Building and scaling DevTools Finding product market fit and monetizing it Why AI is complicating product market fit How Dennis prioritizes mental health as a founder The common mistake people make when hiring — Referenced: Apple’s acquisition of Buddybuild: https://www.cnbc.com/2018/01/02/apple-agrees-to-buy-buddybuild.html AWS: https://aws.amazon.com Bitbucket: https://bitbucket.org Confluence: https://www.atlassian.com/software/confluence GitHub: https://github.com GitLab: https://gitlab.com Looker: https://looker.com Microsoft Azure: https://azure.microsoft.com Stewart Butterfield: https://www.linkedin.com/in/butterfield/ Stripe: https://stripe.com Twilio: https://twilio.com Unblocked: https://getunblocked.com/ — Where to find Dennis Pilarinos: LinkedIn: https://www.linkedin.com/in/dennispi Twitter/X: https://twitter.com/dennispilarinos — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:18) Why building for developers is different (07:28) Buddybuild’s origin story (10:40) Early signs of product market fit (12:22) Managing mental health as a second-time founder (21:09) Building and scaling Unblocked (29:52) Dennis’ cautious take on AI (34:20) Being customer-obsessed (35:25) Unblocked’s decision-making process (38:31) Don’t over-index on competency when hiring (43:36) Why great product is everything (45:41) Monetizing product market fit (48:21) The power of positioning (51:48) Why Dennis doesn’t do demos (54:45) How to deal with customer feedback (57:29) Stewart Butterfield’s impact on Dennis Thu, 21 Mar 2024 11:00:00 -0000 Essential lessons for building and scaling DevTools | Dennis Pilarinos (Unblocked, Apple, Amazon, Buddybuild, Microsoft) full First Round Dennis Pilarinos is the founder and CEO at Unblocked, a developer tool that lets you talk to your codebase. In 2018, Dennis’ first company, Buddybuild, was acquired by Apple, and he was subsequently appointed Director of Development Technologies. Before that, Dennis was a Senior Director at AWS and a Director at Microsoft. Dennis Pilarinos is the founder and CEO at Unblocked, a developer tool that lets you talk to your codebase. In 2018, Dennis’ first company, Buddybuild, was acquired by Apple, and he was subsequently appointed Director of Development Technologies. Before that, Dennis was a Senior Director at AWS and a Director at Microsoft. — In today’s episode, we discuss: Lessons on culture and product from Amazon, Apple, and Microsoft Building and scaling DevTools Finding product market fit and monetizing it Why AI is complicating product market fit How Dennis prioritizes mental health as a founder The common mistake people make when hiring — Referenced: Apple’s acquisition of Buddybuild: https://www.cnbc.com/2018/01/02/apple-agrees-to-buy-buddybuild.html AWS: https://aws.amazon.com Bitbucket: https://bitbucket.org Confluence: https://www.atlassian.com/software/confluence GitHub: https://github.com GitLab: https://gitlab.com Looker: https://looker.com Microsoft Azure: https://azure.microsoft.com Stewart Butterfield: https://www.linkedin.com/in/butterfield/ Stripe: https://stripe.com Twilio: https://twilio.com Unblocked: https://getunblocked.com/ — Where to find Dennis Pilarinos: LinkedIn: https://www.linkedin.com/in/dennispi Twitter/X: https://twitter.com/dennispilarinos — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:18) Why building for developers is different (07:28) Buddybuild’s origin story (10:40) Early signs of product market fit (12:22) Managing mental health as a second-time founder (21:09) Building and scaling Unblocked (29:52) Dennis’ cautious take on AI (34:20) Being customer-obsessed (35:25) Unblocked’s decision-making process (38:31) Don’t over-index on competency when hiring (43:36) Why great product is everything (45:41) Monetizing product market fit (48:21) The power of positioning (51:48) Why Dennis doesn’t do demos (54:45) How to deal with customer feedback (57:29) Stewart Butterfield’s impact on Dennis Dennis Pilarinos is the founder and CEO at Unblocked, a developer tool that lets you talk to your codebase. In 2018, Dennis’ first company, Buddybuild, was acquired by Apple, and he was subsequently appointed Director of Development Technologies. Before that, Dennis was a Senior Director at AWS and a Director at Microsoft.

—

In today’s episode, we discuss:

  • Lessons on culture and product from Amazon, Apple, and Microsoft
  • Building and scaling DevTools
  • Finding product market fit and monetizing it
  • Why AI is complicating product market fit
  • How Dennis prioritizes mental health as a founder
  • The common mistake people make when hiring

—

Referenced:

—

Where to find Dennis Pilarinos:

—

Where to find Brett Berson:

—

Where to find First Round Capital:

—

Timestamps:

(00:00) Introduction

(02:18) Why building for developers is different

(07:28) Buddybuild’s origin story

(10:40) Early signs of product market fit

(12:22) Managing mental health as a second-time founder

(21:09) Building and scaling Unblocked

(29:52) Dennis’ cautious take on AI

(34:20) Being customer-obsessed

(35:25) Unblocked’s decision-making process

(38:31) Don’t over-index on competency when hiring

(43:36) Why great product is everything

(45:41) Monetizing product market fit

(48:21) The power of positioning

(51:48) Why Dennis doesn’t do demos

(54:45) How to deal with customer feedback

(57:29) Stewart Butterfield’s impact on Dennis

]]> 3530 Scaling and selling AI products for enterprise | May Habib (Co-founder and CEO of Writer) May Habib is the co-founder and CEO of Writer, a full-stack generative AI platform built for enterprises. The model is trained on a customer’s own data to create content that is consistent with their brand style and voice. Writer recently raised $100M at a valuation of around $500M. Prior to Writer, May co-founded Qordoba, an AI writing assistant. —  In today’s episode, we discuss: Advice for AI founders in 2024 Why it’s difficult to scale AI products for enterprise The secret to finding champions Signs of a healthy co-founder relationship The future of agentic AI —  Referenced: Accenture: https://www.accenture.com ChatGPT: https://chat.openai.com/ Dropbox: https://www.dropbox.com Goldman Sachs: https://www.goldmansachs.com/ Grammarly: https://www.grammarly.com Jill Kramer: https://www.linkedin.com/in/jill-kramer-64230840/ L’Oreal: https://www.loreal.com/ Northwestern Mutual: https://www.northwesternmutual.com/ Palmyra: https://writer.com/blog/palmyra/ Retrieved Augmented Generation: https://blogs.nvidia.com/blog/what-is-retrieval-augmented-generation/ United Healthcare: https://www.uhc.com/ Vanguard: https://global.vanguard.com/ Waseem Alshikh: https://www.linkedin.com/in/waseemalshikh/ Writer: https://writer.com/ —  Where to find May Habib: LinkedIn: https://www.linkedin.com/in/may-habib/ Twitter/X: https://twitter.com/may_habib —  Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack —  Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast —  Timestamps: (00:00) Introduction (02:34) Writer’s origin story (06:30) Building a full-stack generative AI platform for enterprise (11:56) The #1 challenge building Writer (15:41) Writer’s approach to finding champion customers (20:29) How Writer is winning the enterprise space (27:11) Signs Writer found product-market-fit (29:26) Scaling LLMs for specific use cases (31:53) Writer’s goals for 2024 (33:57) Advice for 0 to 1 founders (35:53) Creating a culture of “connect, challenge, and own” Thu, 29 Feb 2024 12:00:00 -0000 Scaling and selling AI products for enterprise | May Habib (Co-founder and CEO of Writer) full First Round May Habib is the co-founder and CEO of Writer, a full-stack generative AI platform built for enterprises. The model is trained on a customer’s own data to create content that is consistent with their brand style and voice. Writer recently raised $100M at a valuation of around $500M. Prior to Writer, May co-founded Qordoba, an AI writing assistant. May Habib is the co-founder and CEO of Writer, a full-stack generative AI platform built for enterprises. The model is trained on a customer’s own data to create content that is consistent with their brand style and voice. Writer recently raised $100M at a valuation of around $500M. Prior to Writer, May co-founded Qordoba, an AI writing assistant. —  In today’s episode, we discuss: Advice for AI founders in 2024 Why it’s difficult to scale AI products for enterprise The secret to finding champions Signs of a healthy co-founder relationship The future of agentic AI —  Referenced: Accenture: https://www.accenture.com ChatGPT: https://chat.openai.com/ Dropbox: https://www.dropbox.com Goldman Sachs: https://www.goldmansachs.com/ Grammarly: https://www.grammarly.com Jill Kramer: https://www.linkedin.com/in/jill-kramer-64230840/ L’Oreal: https://www.loreal.com/ Northwestern Mutual: https://www.northwesternmutual.com/ Palmyra: https://writer.com/blog/palmyra/ Retrieved Augmented Generation: https://blogs.nvidia.com/blog/what-is-retrieval-augmented-generation/ United Healthcare: https://www.uhc.com/ Vanguard: https://global.vanguard.com/ Waseem Alshikh: https://www.linkedin.com/in/waseemalshikh/ Writer: https://writer.com/ —  Where to find May Habib: LinkedIn: https://www.linkedin.com/in/may-habib/ Twitter/X: https://twitter.com/may_habib —  Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack —  Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast —  Timestamps: (00:00) Introduction (02:34) Writer’s origin story (06:30) Building a full-stack generative AI platform for enterprise (11:56) The #1 challenge building Writer (15:41) Writer’s approach to finding champion customers (20:29) How Writer is winning the enterprise space (27:11) Signs Writer found product-market-fit (29:26) Scaling LLMs for specific use cases (31:53) Writer’s goals for 2024 (33:57) Advice for 0 to 1 founders (35:53) Creating a culture of “connect, challenge, and own” May Habib is the co-founder and CEO of Writer, a full-stack generative AI platform built for enterprises. The model is trained on a customer’s own data to create content that is consistent with their brand style and voice. Writer recently raised $100M at a valuation of around $500M. Prior to Writer, May co-founded Qordoba, an AI writing assistant.

— 

In today’s episode, we discuss:

  • Advice for AI founders in 2024
  • Why it’s difficult to scale AI products for enterprise
  • The secret to finding champions
  • Signs of a healthy co-founder relationship
  • The future of agentic AI

— 

Referenced:

— 

Where to find May Habib:

— 

Where to find Todd Jackson:

— 

Where to find First Round Capital:

— 

Timestamps:

(00:00) Introduction

(02:34) Writer’s origin story

(06:30) Building a full-stack generative AI platform for enterprise

(11:56) The #1 challenge building Writer

(15:41) Writer’s approach to finding champion customers

(20:29) How Writer is winning the enterprise space

(27:11) Signs Writer found product-market-fit

(29:26) Scaling LLMs for specific use cases

(31:53) Writer’s goals for 2024

(33:57) Advice for 0 to 1 founders

(35:53) Creating a culture of “connect, challenge, and own”

]]> 2421 The secret lever Replit pulled to scale ahead of its competition | Amjad Masad (Co-founder and CEO) Amjad Masad is the co-founder and CEO of Replit, an online platform designed for collaborative coding in multiple programming languages. Replit boasts over 30m users, has secured $200M in venture funding, and was recently valued at $1.2B. Before Replit, Amjad was a Software Engineer at Facebook, and a Founding Engineer at Codecademy. — In today’s episode, we discuss: How AI is reshaping the software landscape Bridging the gap between ideas and software Why YC almost rejected Replit four times Replit’s fundraising difficulties, and how Paul Graham helped The secret lever Replit pulled to scale ahead of its competition Replit’s impressive distribution engine — Referenced: 7 Powers: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319/ Codecademy: https://www.codecademy.com/ Hacker News: https://news.ycombinator.com/ I Am a Strange Loop: https://www.amazon.com/Am-Strange-Loop-Douglas-Hofstadter/dp/0465030793 Mythical Man-Month: https://www.amazon.com/Mythical-Man-Month-Software-Engineering-Anniversary/dp/0201835959 On the Naturalness of Software: https://people.inf.ethz.ch/suz/publications/natural.pdf OpenAI: https://openai.com/ Paul Graham: https://twitter.com/paulg Python: https://www.python.org/ Read Write Own: https://www.amazon.com/Read-Write-Own-Building-Internet/dp/0593731387/ Replit: https://replit.com/ Roy Bahat: https://www.linkedin.com/in/roybahat/ Sam Altman: https://twitter.com/sama The Innovator’s Dilemma: https://www.amazon.com/Innovators-Dilemma-Technologies-Management-Innovation/dp/1633691780/ The Little Schemer: https://www.amazon.com/Little-Schemer-Daniel-P-Friedman/dp/0262560992/ Y Combinator: https://www.ycombinator.com/ — Where to find Amjad Masad: LinkedIn: https://www.linkedin.com/in/amjadmasad Twitter/X: https://twitter.com/amasad — Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:31) Replit’s origin story (08:24) Starting Facebook’s JavaScript infrastructure team (10:36) Amjad’s unique path to entrepreneurship (16:04) How Replit got its early users (17:00) Replit’s fundraising difficulties (17:54) Why YC almost rejected Replit four times (20:23) Building Replit’s distribution engine (22:08) Drivers of Replit’s growth (27:41) What Silicon Valley gets wrong (30:09) Replit’s monetization strategy (32:29) Integrating AI into the platform (36:18) The impact of AI on software engineering (39:40) Defining the new “software creator” role (41:43) How to keep up with developments in AI (46:24) Replit’s goals for 2024 (48:11) Advice for founders: defy conventional wisdom (51:12) Amjad’s 4 favorite books Thu, 15 Feb 2024 12:00:00 -0000 The secret lever Replit pulled to scale ahead of its competition | Amjad Masad (Co-founder and CEO) full First Round Amjad Masad is the co-founder and CEO of Replit, an online platform designed for collaborative coding in multiple programming languages. Replit boasts over 30m users, has secured $200M in venture funding, and was recently valued at $1.2B. Before Replit, Amjad was a Software Engineer at Facebook, and a Founding Engineer at Codecademy. Amjad Masad is the co-founder and CEO of Replit, an online platform designed for collaborative coding in multiple programming languages. Replit boasts over 30m users, has secured $200M in venture funding, and was recently valued at $1.2B. Before Replit, Amjad was a Software Engineer at Facebook, and a Founding Engineer at Codecademy. — In today’s episode, we discuss: How AI is reshaping the software landscape Bridging the gap between ideas and software Why YC almost rejected Replit four times Replit’s fundraising difficulties, and how Paul Graham helped The secret lever Replit pulled to scale ahead of its competition Replit’s impressive distribution engine — Referenced: 7 Powers: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319/ Codecademy: https://www.codecademy.com/ Hacker News: https://news.ycombinator.com/ I Am a Strange Loop: https://www.amazon.com/Am-Strange-Loop-Douglas-Hofstadter/dp/0465030793 Mythical Man-Month: https://www.amazon.com/Mythical-Man-Month-Software-Engineering-Anniversary/dp/0201835959 On the Naturalness of Software: https://people.inf.ethz.ch/suz/publications/natural.pdf OpenAI: https://openai.com/ Paul Graham: https://twitter.com/paulg Python: https://www.python.org/ Read Write Own: https://www.amazon.com/Read-Write-Own-Building-Internet/dp/0593731387/ Replit: https://replit.com/ Roy Bahat: https://www.linkedin.com/in/roybahat/ Sam Altman: https://twitter.com/sama The Innovator’s Dilemma: https://www.amazon.com/Innovators-Dilemma-Technologies-Management-Innovation/dp/1633691780/ The Little Schemer: https://www.amazon.com/Little-Schemer-Daniel-P-Friedman/dp/0262560992/ Y Combinator: https://www.ycombinator.com/ — Where to find Amjad Masad: LinkedIn: https://www.linkedin.com/in/amjadmasad Twitter/X: https://twitter.com/amasad — Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:31) Replit’s origin story (08:24) Starting Facebook’s JavaScript infrastructure team (10:36) Amjad’s unique path to entrepreneurship (16:04) How Replit got its early users (17:00) Replit’s fundraising difficulties (17:54) Why YC almost rejected Replit four times (20:23) Building Replit’s distribution engine (22:08) Drivers of Replit’s growth (27:41) What Silicon Valley gets wrong (30:09) Replit’s monetization strategy (32:29) Integrating AI into the platform (36:18) The impact of AI on software engineering (39:40) Defining the new “software creator” role (41:43) How to keep up with developments in AI (46:24) Replit’s goals for 2024 (48:11) Advice for founders: defy conventional wisdom (51:12) Amjad’s 4 favorite books Amjad Masad is the co-founder and CEO of Replit, an online platform designed for collaborative coding in multiple programming languages. Replit boasts over 30m users, has secured $200M in venture funding, and was recently valued at $1.2B. Before Replit, Amjad was a Software Engineer at Facebook, and a Founding Engineer at Codecademy.

—

In today’s episode, we discuss:

  • How AI is reshaping the software landscape
  • Bridging the gap between ideas and software
  • Why YC almost rejected Replit four times
  • Replit’s fundraising difficulties, and how Paul Graham helped
  • The secret lever Replit pulled to scale ahead of its competition
  • Replit’s impressive distribution engine

—

Referenced:

—

Where to find Amjad Masad:

—

Where to find Todd Jackson:

—

Where to find First Round Capital:

—

Timestamps:

(00:00) Introduction

(02:31) Replit’s origin story

(08:24) Starting Facebook’s JavaScript infrastructure team

(10:36) Amjad’s unique path to entrepreneurship

(16:04) How Replit got its early users

(17:00) Replit’s fundraising difficulties

(17:54) Why YC almost rejected Replit four times

(20:23) Building Replit’s distribution engine

(22:08) Drivers of Replit’s growth

(27:41) What Silicon Valley gets wrong

(30:09) Replit’s monetization strategy

(32:29) Integrating AI into the platform

(36:18) The impact of AI on software engineering

(39:40) Defining the new “software creator” role

(41:43) How to keep up with developments in AI

(46:24) Replit’s goals for 2024

(48:11) Advice for founders: defy conventional wisdom

(51:12) Amjad’s 4 favorite books

]]> 3226 Lessons from Gusto & Square on finding your product wedge | Michael Cieri Michael Cieri is the Chief Product Officer at Gusto, an HR and payroll platform used by more than 300,000 businesses. With a decade of experience, he has led successful SMB product development and scaled high-performing orgs. Before Gusto, Michael was also the Head of Product at Square, where he led a team of 15+ PMs responsible for $600m in annual revenue. Michael was also the VP of Product Management at Opendoor. — In today’s episode, we discuss: Key product strategies used by Square and Gusto The pros and cons of building for SMBs How to build horizontal after creating a wedge The catch with building vertical SaaS How product teams can move faster Developing product sense and intuition — Referenced: Alyssa Henry: https://www.linkedin.com/in/alyssa-henry-0905692/ Copilot: https://copilot.microsoft.com/ Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1/ Gusto: https://gusto.com/ High Output Management: https://amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 Marty Cagan: https://www.linkedin.com/in/cagan/ Opendoor: https://www.opendoor.com/ Silicon Valley Product Group: https://www.svpg.com/ Square: https://squareup.com/ The Three Horizons Model: https://www.mckinsey.com/enduring-ideas-the-three-horizons-of-growth Toast: https://pos.toasttab.com/ — Where to find Michael Cieri: LinkedIn: https://www.linkedin.com/in/michaelcieri/ — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:41) Why SMBs require unique software solutions (05:58) The level of specificity required when building for SMBs (08:47) Finding Square’s form-fitting solution (11:48) Building vertical versus horizontal SaaS (14:34) Inside Square and Gusto’s decision making framework (16:15) How to build horizontally from a wedge product (23:00) Using the Three Horizons Model (25:29) How to craft a compelling vision for products (28:51) How to assess Horizon 3 bets (32:08) How to give employees the freedom to try things (34:24) Creating a risk-taking culture (37:27) Essential advice for new PMs (40:27) Common thread with bad product pitches (42:29) Applying the Horizon framework at Gusto (44:46) Developing good product sense (47:43) 5 signs of great product sense (49:03) Why product sense is like athletic ability (51:43) How to ship faster without increasing headcount (56:10) People who had an outsized impact on Michael Thu, 08 Feb 2024 12:00:00 -0000 Lessons from Gusto & Square on Finding Your Product Wedge | Michael Cieri full First Round Michael Cieri is the Chief Product Officer at Gusto, an HR and payroll platform used by more than 300,000 businesses. With a decade of experience, he has led successful SMB product development and scaled high-performing orgs. Before Gusto, Michael was also the Head of Product at Square, where he led a team of 15+ PMs responsible for $600m in annual revenue. Michael was also the VP of Product Management at Opendoor. Michael Cieri is the Chief Product Officer at Gusto, an HR and payroll platform used by more than 300,000 businesses. With a decade of experience, he has led successful SMB product development and scaled high-performing orgs. Before Gusto, Michael was also the Head of Product at Square, where he led a team of 15+ PMs responsible for $600m in annual revenue. Michael was also the VP of Product Management at Opendoor. — In today’s episode, we discuss: Key product strategies used by Square and Gusto The pros and cons of building for SMBs How to build horizontal after creating a wedge The catch with building vertical SaaS How product teams can move faster Developing product sense and intuition — Referenced: Alyssa Henry: https://www.linkedin.com/in/alyssa-henry-0905692/ Copilot: https://copilot.microsoft.com/ Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1/ Gusto: https://gusto.com/ High Output Management: https://amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 Marty Cagan: https://www.linkedin.com/in/cagan/ Opendoor: https://www.opendoor.com/ Silicon Valley Product Group: https://www.svpg.com/ Square: https://squareup.com/ The Three Horizons Model: https://www.mckinsey.com/enduring-ideas-the-three-horizons-of-growth Toast: https://pos.toasttab.com/ — Where to find Michael Cieri: LinkedIn: https://www.linkedin.com/in/michaelcieri/ — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:41) Why SMBs require unique software solutions (05:58) The level of specificity required when building for SMBs (08:47) Finding Square’s form-fitting solution (11:48) Building vertical versus horizontal SaaS (14:34) Inside Square and Gusto’s decision making framework (16:15) How to build horizontally from a wedge product (23:00) Using the Three Horizons Model (25:29) How to craft a compelling vision for products (28:51) How to assess Horizon 3 bets (32:08) How to give employees the freedom to try things (34:24) Creating a risk-taking culture (37:27) Essential advice for new PMs (40:27) Common thread with bad product pitches (42:29) Applying the Horizon framework at Gusto (44:46) Developing good product sense (47:43) 5 signs of great product sense (49:03) Why product sense is like athletic ability (51:43) How to ship faster without increasing headcount (56:10) People who had an outsized impact on Michael Michael Cieri is the Chief Product Officer at Gusto, an HR and payroll platform used by more than 300,000 businesses. With a decade of experience, he has led successful SMB product development and scaled high-performing orgs. Before Gusto, Michael was also the Head of Product at Square, where he led a team of 15+ PMs responsible for $600m in annual revenue. Michael was also the VP of Product Management at Opendoor.

—

In today’s episode, we discuss:

  • Key product strategies used by Square and Gusto
  • The pros and cons of building for SMBs
  • How to build horizontal after creating a wedge
  • The catch with building vertical SaaS
  • How product teams can move faster
  • Developing product sense and intuition

—

Referenced:

—

Where to find Michael Cieri:

—

Where to find Brett Berson:

—

Where to find First Round Capital:

—

Timestamps:

(00:00) Introduction

(02:41) Why SMBs require unique software solutions

(05:58) The level of specificity required when building for SMBs

(08:47) Finding Square’s form-fitting solution

(11:48) Building vertical versus horizontal SaaS

(14:34) Inside Square and Gusto’s decision making framework

(16:15) How to build horizontally from a wedge product

(23:00) Using the Three Horizons Model

(25:29) How to craft a compelling vision for products

(28:51) How to assess Horizon 3 bets

(32:08) How to give employees the freedom to try things

(34:24) Creating a risk-taking culture

(37:27) Essential advice for new PMs

(40:27) Common thread with bad product pitches

(42:29) Applying the Horizon framework at Gusto

(44:46) Developing good product sense

(47:43) 5 signs of great product sense

(49:03) Why product sense is like athletic ability

(51:43) How to ship faster without increasing headcount

(56:10) People who had an outsized impact on Michael

]]> 3548 A customer success masterclass | How to design, build, and scale a CS org | Stephanie Berner (LinkedIn) Stephanie Berner is a Customer Success Executive at LinkedIn. Since 2018, Stephanie has spearheaded all post-sales functions at LinkedIn Sales Solutions through its period of rapid growth. With a background in building and scaling customer success teams at Box, Medallia, and Opower, Stephanie has extensive experience in delivering exceptional customer experiences across various company stages. — In this episode, we discuss: Common customer success mistakes Creating a world-class customer success org Tactics for hiring exceptional talent How to structure compensation packages Where customer success fits into the wider org Key early-stage customer success metrics and rituals Successful strategies from Box, Medallia, and LinkedIn — Referenced: Aaron Levie: https://www.linkedin.com/in/boxaaron/ Box: https://www.box.com/ David Love: https://www.linkedin.com/in/david-s-love/ Gainsight: https://www.gainsight.com/ Jon Herstein: https://www.linkedin.com/in/jonherstein/ Jonathan Lister: https://www.linkedin.com/in/jonathanlister/ Ken Fine: https://www.linkedin.com/in/kmfine/ Medallia: https://www.medallia.com/ Nick Mehta: https://www.linkedin.com/in/nickmehta/ Opower: https://www.oracle.com/utilities/opower-energy-efficiency/ — Where to find Stephanie Berner: LinkedIn: https://www.linkedin.com/in/stephanieberner/ — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:21) Formalizing customer success at a startup (05:01) Hiring ICs before CSMs (06:22) Tactics for hiring standout talent (11:39) 3 questions to ask candidates (15:38) Fail-case patterns among customer success hires (17:49) Considering candidates with non-traditional backgrounds (21:21) Indexing toward a bias for action (24:17) What v1 of customer success looks like (26:03) Key early-stage customer success metrics (28:21) Whether customer success or sales should own renewals (30:40) Where customer success fits into the org (32:14) Why customer success doesn’t report to an executive (33:48) Distinguishing a product problem from a customer success one (35:18) Simple way to deal with customer churn (39:21) Tactics to get customers to give honest feedback (40:58) What happens when customer success and product teams collaborate (44:14) Rituals for zero-to-one customer success (48:23) How to structure an early customer success team (52:01) Structuring compensation packages (54:35) Aligning customer success with the business model (60:14) The role of customer success in B2B software (62:17) Common customer success mistakes (67:44) People who had an outsized impact on Stephanie Thu, 01 Feb 2024 12:00:00 -0000 A customer success masterclass | How to design, build, and scale a CS org | Stephanie Berner (LinkedIn) full First Round Stephanie Berner is a Customer Success Executive at LinkedIn. Since 2018, Stephanie has spearheaded all post-sales functions at LinkedIn Sales Solutions through its period of rapid growth. With a background in building and scaling customer success teams at Box, Medallia, and Opower, Stephanie has extensive experience in delivering exceptional customer experiences across various company stages. Stephanie Berner is a Customer Success Executive at LinkedIn. Since 2018, Stephanie has spearheaded all post-sales functions at LinkedIn Sales Solutions through its period of rapid growth. With a background in building and scaling customer success teams at Box, Medallia, and Opower, Stephanie has extensive experience in delivering exceptional customer experiences across various company stages. — In this episode, we discuss: Common customer success mistakes Creating a world-class customer success org Tactics for hiring exceptional talent How to structure compensation packages Where customer success fits into the wider org Key early-stage customer success metrics and rituals Successful strategies from Box, Medallia, and LinkedIn — Referenced: Aaron Levie: https://www.linkedin.com/in/boxaaron/ Box: https://www.box.com/ David Love: https://www.linkedin.com/in/david-s-love/ Gainsight: https://www.gainsight.com/ Jon Herstein: https://www.linkedin.com/in/jonherstein/ Jonathan Lister: https://www.linkedin.com/in/jonathanlister/ Ken Fine: https://www.linkedin.com/in/kmfine/ Medallia: https://www.medallia.com/ Nick Mehta: https://www.linkedin.com/in/nickmehta/ Opower: https://www.oracle.com/utilities/opower-energy-efficiency/ — Where to find Stephanie Berner: LinkedIn: https://www.linkedin.com/in/stephanieberner/ — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:21) Formalizing customer success at a startup (05:01) Hiring ICs before CSMs (06:22) Tactics for hiring standout talent (11:39) 3 questions to ask candidates (15:38) Fail-case patterns among customer success hires (17:49) Considering candidates with non-traditional backgrounds (21:21) Indexing toward a bias for action (24:17) What v1 of customer success looks like (26:03) Key early-stage customer success metrics (28:21) Whether customer success or sales should own renewals (30:40) Where customer success fits into the org (32:14) Why customer success doesn’t report to an executive (33:48) Distinguishing a product problem from a customer success one (35:18) Simple way to deal with customer churn (39:21) Tactics to get customers to give honest feedback (40:58) What happens when customer success and product teams collaborate (44:14) Rituals for zero-to-one customer success (48:23) How to structure an early customer success team (52:01) Structuring compensation packages (54:35) Aligning customer success with the business model (60:14) The role of customer success in B2B software (62:17) Common customer success mistakes (67:44) People who had an outsized impact on Stephanie Stephanie Berner is a Customer Success Executive at LinkedIn. Since 2018, Stephanie has spearheaded all post-sales functions at LinkedIn Sales Solutions through its period of rapid growth. With a background in building and scaling customer success teams at Box, Medallia, and Opower, Stephanie has extensive experience in delivering exceptional customer experiences across various company stages.

—

In this episode, we discuss:

  • Common customer success mistakes
  • Creating a world-class customer success org
  • Tactics for hiring exceptional talent
  • How to structure compensation packages
  • Where customer success fits into the wider org
  • Key early-stage customer success metrics and rituals
  • Successful strategies from Box, Medallia, and LinkedIn

—

Referenced:

—

Where to find Stephanie Berner:

—

Where to find Brett Berson:

—

Where to find First Round Capital:

—

Timestamps:

(00:00) Introduction

(02:21) Formalizing customer success at a startup

(05:01) Hiring ICs before CSMs

(06:22) Tactics for hiring standout talent

(11:39) 3 questions to ask candidates

(15:38) Fail-case patterns among customer success hires

(17:49) Considering candidates with non-traditional backgrounds

(21:21) Indexing toward a bias for action

(24:17) What v1 of customer success looks like

(26:03) Key early-stage customer success metrics

(28:21) Whether customer success or sales should own renewals

(30:40) Where customer success fits into the org

(32:14) Why customer success doesn’t report to an executive

(33:48) Distinguishing a product problem from a customer success one

(35:18) Simple way to deal with customer churn

(39:21) Tactics to get customers to give honest feedback

(40:58) What happens when customer success and product teams collaborate

(44:14) Rituals for zero-to-one customer success

(48:23) How to structure an early customer success team

(52:01) Structuring compensation packages

(54:35) Aligning customer success with the business model

(60:14) The role of customer success in B2B software

(62:17) Common customer success mistakes

(67:44) People who had an outsized impact on Stephanie

]]> 4267 The human side of world-class engineering leadership | Michael Lopp (Apple, Palantir, Slack) Michael Lopp is an experienced engineering leader known for building products at iconic companies like Apple, Borland, Netscape, Palantir, and Slack. Since 2002, Lopp — as he’s more commonly known — has written about engineering, management, and leadership on his popular blog ‘Rands in Repose’. He is also the renowned author of three books: Being Geek, Managing Humans, and The Art of Leadership. — In today’s episode, we discuss: Lopp’s “utopia” — where engineers have time to create and invent What makes an excellent engineering leader The flexibility required for managerial roles in different contexts Navigating internal dynamics between design, engineering, and product How to build and grow effective engineering orgs The importance of understanding individual motivations Key lessons from over 30 years in the industry — Referenced: AOL: https://aol.com Apple: https://www.apple.com Borland: https://en.wikipedia.org/wiki/Borland Netscape: https://en.wikipedia.org/wiki/Netscape Palantir: https://www.palantir.com/ Phillipe Kahn: https://www.linkedin.com/in/philippekahn/ Pinterest: https://www.pinterest.com/ Slack: https://slack.com Stewart Butterfield: https://www.linkedin.com/in/butterfield/ Tom Paquin: https://www.linkedin.com/in/tom-paquin-240b4b2/ — Where to find Michael Lopp: Blog: https://randsinrepose.com/ LinkedIn: https://www.linkedin.com/in/michaellopp/ Twitter/X: https://twitter.com/rands — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:20) Beginning career at Borland (05:41) The difficulty with shipping software at scale (07:52) Why it’s harder to ship today than ever before (09:42) What makes a startup operationally sound (11:23) Why engineers should have concrete time to invent (19:42) How PMs can improve engineering culture (21:35) An engineer’s perspective on good product management (23:36) The role of product compared to design and engineering (26:38) How micromanagement kills creativity (29:35) Fostering a debate culture in an org (31:26) Declarative versus prescriptive leadership (36:09) 3 ideas on leadership from Lopp’s upcoming book (38:29) Understanding employee motivation (42:28) Advice on discovering what motivates people (46:06) Why teams should reorg every 6 months (48:32) One thing all successful leaders do (52:22) Why sound judgment is crucial for decision-making (53:45) Crystallized lessons from working at software giants (56:19) Why Lopp is afraid of becoming irrelevant (57:58) The number one leadership lesson from Lopp’s career (59:32) What Lopp has changed his mind on over time (61:12) People who had an outsized impact on Lopp Thu, 25 Jan 2024 12:00:00 -0000 The human side of world-class engineering leadership | Michael Lopp (Apple, Palantir, Slack) full First Round Michael Lopp is an experienced engineering leader known for building products at iconic companies like Apple, Borland, Netscape, Palantir, and Slack. Since 2002, Lopp — as he’s more commonly known — has written about engineering, management, and leadership on his popular blog ‘Rands in Repose’. He is also the renowned author of three books: Being Geek, Managing Humans, and The Art of Leadership. Michael Lopp is an experienced engineering leader known for building products at iconic companies like Apple, Borland, Netscape, Palantir, and Slack. Since 2002, Lopp — as he’s more commonly known — has written about engineering, management, and leadership on his popular blog ‘Rands in Repose’. He is also the renowned author of three books: Being Geek, Managing Humans, and The Art of Leadership. — In today’s episode, we discuss: Lopp’s “utopia” — where engineers have time to create and invent What makes an excellent engineering leader The flexibility required for managerial roles in different contexts Navigating internal dynamics between design, engineering, and product How to build and grow effective engineering orgs The importance of understanding individual motivations Key lessons from over 30 years in the industry — Referenced: AOL: https://aol.com Apple: https://www.apple.com Borland: https://en.wikipedia.org/wiki/Borland Netscape: https://en.wikipedia.org/wiki/Netscape Palantir: https://www.palantir.com/ Phillipe Kahn: https://www.linkedin.com/in/philippekahn/ Pinterest: https://www.pinterest.com/ Slack: https://slack.com Stewart Butterfield: https://www.linkedin.com/in/butterfield/ Tom Paquin: https://www.linkedin.com/in/tom-paquin-240b4b2/ — Where to find Michael Lopp: Blog: https://randsinrepose.com/ LinkedIn: https://www.linkedin.com/in/michaellopp/ Twitter/X: https://twitter.com/rands — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:20) Beginning career at Borland (05:41) The difficulty with shipping software at scale (07:52) Why it’s harder to ship today than ever before (09:42) What makes a startup operationally sound (11:23) Why engineers should have concrete time to invent (19:42) How PMs can improve engineering culture (21:35) An engineer’s perspective on good product management (23:36) The role of product compared to design and engineering (26:38) How micromanagement kills creativity (29:35) Fostering a debate culture in an org (31:26) Declarative versus prescriptive leadership (36:09) 3 ideas on leadership from Lopp’s upcoming book (38:29) Understanding employee motivation (42:28) Advice on discovering what motivates people (46:06) Why teams should reorg every 6 months (48:32) One thing all successful leaders do (52:22) Why sound judgment is crucial for decision-making (53:45) Crystallized lessons from working at software giants (56:19) Why Lopp is afraid of becoming irrelevant (57:58) The number one leadership lesson from Lopp’s career (59:32) What Lopp has changed his mind on over time (61:12) People who had an outsized impact on Lopp Michael Lopp is an experienced engineering leader known for building products at iconic companies like Apple, Borland, Netscape, Palantir, and Slack. Since 2002, Lopp — as he’s more commonly known — has written about engineering, management, and leadership on his popular blog ‘Rands in Repose’. He is also the renowned author of three books: Being Geek, Managing Humans, and The Art of Leadership.

—

In today’s episode, we discuss:

  • Lopp’s “utopia” — where engineers have time to create and invent
  • What makes an excellent engineering leader
  • The flexibility required for managerial roles in different contexts
  • Navigating internal dynamics between design, engineering, and product
  • How to build and grow effective engineering orgs
  • The importance of understanding individual motivations
  • Key lessons from over 30 years in the industry

—

Referenced:

—

Where to find Michael Lopp:

—

Where to find Brett Berson:

—

Where to find First Round Capital:

—

Timestamps:

(00:00) Introduction

(02:20) Beginning career at Borland

(05:41) The difficulty with shipping software at scale

(07:52) Why it’s harder to ship today than ever before

(09:42) What makes a startup operationally sound

(11:23) Why engineers should have concrete time to invent

(19:42) How PMs can improve engineering culture

(21:35) An engineer’s perspective on good product management

(23:36) The role of product compared to design and engineering

(26:38) How micromanagement kills creativity

(29:35) Fostering a debate culture in an org

(31:26) Declarative versus prescriptive leadership

(36:09) 3 ideas on leadership from Lopp’s upcoming book

(38:29) Understanding employee motivation

(42:28) Advice on discovering what motivates people

(46:06) Why teams should reorg every 6 months

(48:32) One thing all successful leaders do

(52:22) Why sound judgment is crucial for decision-making

(53:45) Crystallized lessons from working at software giants

(56:19) Why Lopp is afraid of becoming irrelevant

(57:58) The number one leadership lesson from Lopp’s career

(59:32) What Lopp has changed his mind on over time

(61:12) People who had an outsized impact on Lopp

]]> 3886 Clay’s path to product-market-fit: Building vertical, creating power users, and understanding founder psychology | Kareem Amin (Co-founder and CEO) Kareem Amin is the co-founder of Clay, a lead-generation software that uses AI to scrape 50+ databases and help companies scale their outbound campaigns. Before Clay, Kareem was the VP of Product at The Wall Street Journal. Kareem also co-founded Frame (useframe.com) which was acquired by Sailthru in 2012. — In today’s episode, we discuss: Creating a community of power users How to stay ruthlessly focused and make decisions faster Clay’s principles for finding product-market-fit Why a company is the reflection of its founder’s personality Aligning your own psychology with the business The mindset change from a first to second-time founder — Referenced: Airtable: https://www.airtable.com/ Clay: https://www.clay.com/ Figma: https://www.figma.com/ Internal Family Systems: https://ifs-institute.com/ NetSuite: https://www.netsuite.com/ Notion: https://www.notion.com Sailthru: https://www.sailthru.com/ — Where to find Kareem Amin: LinkedIn: https://www.linkedin.com/in/kareemamin/ Twitter/X: https://twitter.com/kareemamin — Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:36) Clay’s origin story (05:54) Building for a specific customer (10:42) Knowing when to build for a broader customer-base (12:46) The life spiral framework (15:52) How founders can make better decisions (18:57) Kareem’s principles for product-market-fit (25:36) Clay’s customer journey (30:04) Interesting tactic to find power users (34:00) How to know you have product-market-fit (37:11) The impact of founder psychology on the business (39:41) Mastering commitment to sprints (40:47) How Kareem’s own personality affected his company (43:31) Actionable advice to understand founder psychology (46:25) Why focus is misunderstood (47:09) The mindset shift from a first to second-time founder (50:28) What’s next for Clay (52:14) The best piece of advice Kareem has actioned Thu, 18 Jan 2024 12:00:00 -0000 Clay’s path to product-market-fit: Building vertical, creating power users, and understanding founder psychology | Kareem Amin (Co-founder and CEO) full First Round Kareem Amin is the co-founder of Clay, a lead-generation software that uses AI to scrape 50+ databases and help companies scale their outbound campaigns. Before Clay, Kareem was the VP of Product at The Wall Street Journal. Kareem also co-founded Frame (useframe.com) which was acquired by Sailthru in 2012. Kareem Amin is the co-founder of Clay, a lead-generation software that uses AI to scrape 50+ databases and help companies scale their outbound campaigns. Before Clay, Kareem was the VP of Product at The Wall Street Journal. Kareem also co-founded Frame (useframe.com) which was acquired by Sailthru in 2012. — In today’s episode, we discuss: Creating a community of power users How to stay ruthlessly focused and make decisions faster Clay’s principles for finding product-market-fit Why a company is the reflection of its founder’s personality Aligning your own psychology with the business The mindset change from a first to second-time founder — Referenced: Airtable: https://www.airtable.com/ Clay: https://www.clay.com/ Figma: https://www.figma.com/ Internal Family Systems: https://ifs-institute.com/ NetSuite: https://www.netsuite.com/ Notion: https://www.notion.com Sailthru: https://www.sailthru.com/ — Where to find Kareem Amin: LinkedIn: https://www.linkedin.com/in/kareemamin/ Twitter/X: https://twitter.com/kareemamin — Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:36) Clay’s origin story (05:54) Building for a specific customer (10:42) Knowing when to build for a broader customer-base (12:46) The life spiral framework (15:52) How founders can make better decisions (18:57) Kareem’s principles for product-market-fit (25:36) Clay’s customer journey (30:04) Interesting tactic to find power users (34:00) How to know you have product-market-fit (37:11) The impact of founder psychology on the business (39:41) Mastering commitment to sprints (40:47) How Kareem’s own personality affected his company (43:31) Actionable advice to understand founder psychology (46:25) Why focus is misunderstood (47:09) The mindset shift from a first to second-time founder (50:28) What’s next for Clay (52:14) The best piece of advice Kareem has actioned Kareem Amin is the co-founder of Clay, a lead-generation software that uses AI to scrape 50+ databases and help companies scale their outbound campaigns. Before Clay, Kareem was the VP of Product at The Wall Street Journal. Kareem also co-founded Frame (useframe.com) which was acquired by Sailthru in 2012.

—

In today’s episode, we discuss:

  • Creating a community of power users
  • How to stay ruthlessly focused and make decisions faster
  • Clay’s principles for finding product-market-fit
  • Why a company is the reflection of its founder’s personality
  • Aligning your own psychology with the business
  • The mindset change from a first to second-time founder

—

Referenced:

—

Where to find Kareem Amin:

—

Where to find Todd Jackson:

—

Where to find First Round Capital:

—

Timestamps:

(00:00) Introduction

(02:36) Clay’s origin story

(05:54) Building for a specific customer

(10:42) Knowing when to build for a broader customer-base

(12:46) The life spiral framework

(15:52) How founders can make better decisions

(18:57) Kareem’s principles for product-market-fit

(25:36) Clay’s customer journey

(30:04) Interesting tactic to find power users

(34:00) How to know you have product-market-fit

(37:11) The impact of founder psychology on the business

(39:41) Mastering commitment to sprints

(40:47) How Kareem’s own personality affected his company

(43:31) Actionable advice to understand founder psychology

(46:25) Why focus is misunderstood

(47:09) The mindset shift from a first to second-time founder

(50:28) What’s next for Clay

(52:14) The best piece of advice Kareem has actioned

]]> 3256 Inside Figma’s early days: How to build a world-class sales org | Kyle Parrish (VP of Sales) Kyle Parrish, Figma’s first sales hire, built the company’s zero-to-one sales engine from scratch. Figma now has more than 3 million monthly users. Prior to Figma, Kyle spent 5 years at Dropbox in various sales roles. At Dropbox, Kyle successfully launched and scaled the Austin office to 100+ people, and then led the enterprise sales function in San Francisco and New York. — In today’s episode, we discuss: The right time to build a sales function Hiring and scaling a successful sales org Building a unique sales culture Career advice for ambitious salespeople Figma’s early sales motion How to integrate your first sales hire Navigating the founder/Head of Sales relationship — Referenced: Amanda Kleha: https://www.linkedin.com/in/amanda-kleha-015599/ Asana: https://asana.com/ Atlassian: https://www.atlassian.com/ Claire Butler: https://www.linkedin.com/in/clairetbutler/ Dropbox: https://www.dropbox.com/ Dylan Field: https://www.linkedin.com/in/dylanfield/ FigJam: https://www.figma.com/figjam/ Figma: https://www.figma.com/ Kevin Egan: https://www.linkedin.com/in/kevin-egan-59719/ Oliver Jay: https://www.linkedin.com/in/oliverjayleadership/ Praveer Melwani: https://www.linkedin.com/in/praveer-melwani/ Salesforce: https://www.salesforce.com/ Slack: https://www.slack.com/ — Where to find Kyle Parrish: LinkedIn: https://www.linkedin.com/in/kparrish8/ Twitter/X: https://twitter.com/KyleHParrish — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:10) What founders need to figure out before hiring salespeople (03:48) Who to hire as your first salesperson (05:34) Transitioning away from founder-led sales (07:07) Tactics for hiring great salespeople (12:50) The ideal experience sales candidates should have (13:49) Common traits of successful salespeople (18:45) What it was like being Figma’s first sales hire (19:59) Interesting tactic to integrate the first sales hire (21:16) How Figma executed its early sales motion (32:27) Why Figma changed its customer narrative (34:03) Building outbound sales strategy at Figma (36:17) Segmented pricing and no discounts (41:55) Kyle’s transition from Dropbox to Figma (47:25) Creating a world-class sales culture (51:46) How Figma does sales differently (54:02) Building the initial sales team around a passion for the product (57:12) Figma’s unique hiring process for salespeople (60:40) Advice for founders hiring their first salesperson (63:18) The secret to Dylan Field’s success (64:33) How to scale yourself as an early hire (66:25) Oliver Jay’s impact on Kyle Thu, 11 Jan 2024 12:00:00 -0000 Inside Figma’s early days: How to build a world-class sales org | Kyle Parrish (VP of Sales) full First Round Kyle Parrish, Figma’s first sales hire, built the company’s zero-to-one sales engine from scratch. Figma now has more than 3 million monthly users. Prior to Figma, Kyle spent 5 years at Dropbox in various sales roles. At Dropbox, Kyle successfully launched and scaled the Austin office to 100+ people, and then led the enterprise sales function in San Francisco and New York. Kyle Parrish, Figma’s first sales hire, built the company’s zero-to-one sales engine from scratch. Figma now has more than 3 million monthly users. Prior to Figma, Kyle spent 5 years at Dropbox in various sales roles. At Dropbox, Kyle successfully launched and scaled the Austin office to 100+ people, and then led the enterprise sales function in San Francisco and New York. — In today’s episode, we discuss: The right time to build a sales function Hiring and scaling a successful sales org Building a unique sales culture Career advice for ambitious salespeople Figma’s early sales motion How to integrate your first sales hire Navigating the founder/Head of Sales relationship — Referenced: Amanda Kleha: https://www.linkedin.com/in/amanda-kleha-015599/ Asana: https://asana.com/ Atlassian: https://www.atlassian.com/ Claire Butler: https://www.linkedin.com/in/clairetbutler/ Dropbox: https://www.dropbox.com/ Dylan Field: https://www.linkedin.com/in/dylanfield/ FigJam: https://www.figma.com/figjam/ Figma: https://www.figma.com/ Kevin Egan: https://www.linkedin.com/in/kevin-egan-59719/ Oliver Jay: https://www.linkedin.com/in/oliverjayleadership/ Praveer Melwani: https://www.linkedin.com/in/praveer-melwani/ Salesforce: https://www.salesforce.com/ Slack: https://www.slack.com/ — Where to find Kyle Parrish: LinkedIn: https://www.linkedin.com/in/kparrish8/ Twitter/X: https://twitter.com/KyleHParrish — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:10) What founders need to figure out before hiring salespeople (03:48) Who to hire as your first salesperson (05:34) Transitioning away from founder-led sales (07:07) Tactics for hiring great salespeople (12:50) The ideal experience sales candidates should have (13:49) Common traits of successful salespeople (18:45) What it was like being Figma’s first sales hire (19:59) Interesting tactic to integrate the first sales hire (21:16) How Figma executed its early sales motion (32:27) Why Figma changed its customer narrative (34:03) Building outbound sales strategy at Figma (36:17) Segmented pricing and no discounts (41:55) Kyle’s transition from Dropbox to Figma (47:25) Creating a world-class sales culture (51:46) How Figma does sales differently (54:02) Building the initial sales team around a passion for the product (57:12) Figma’s unique hiring process for salespeople (60:40) Advice for founders hiring their first salesperson (63:18) The secret to Dylan Field’s success (64:33) How to scale yourself as an early hire (66:25) Oliver Jay’s impact on Kyle Kyle Parrish, Figma’s first sales hire, built the company’s zero-to-one sales engine from scratch. Figma now has more than 3 million monthly users. Prior to Figma, Kyle spent 5 years at Dropbox in various sales roles. At Dropbox, Kyle successfully launched and scaled the Austin office to 100+ people, and then led the enterprise sales function in San Francisco and New York.

—

In today’s episode, we discuss:

  • The right time to build a sales function
  • Hiring and scaling a successful sales org
  • Building a unique sales culture
  • Career advice for ambitious salespeople
  • Figma’s early sales motion
  • How to integrate your first sales hire
  • Navigating the founder/Head of Sales relationship

—

Referenced:

—

Where to find Kyle Parrish:

—

Where to find Brett Berson:

—

Where to find First Round Capital:

—

Timestamps:

(00:00) Introduction

(02:10) What founders need to figure out before hiring salespeople

(03:48) Who to hire as your first salesperson

(05:34) Transitioning away from founder-led sales

(07:07) Tactics for hiring great salespeople

(12:50) The ideal experience sales candidates should have

(13:49) Common traits of successful salespeople

(18:45) What it was like being Figma’s first sales hire

(19:59) Interesting tactic to integrate the first sales hire

(21:16) How Figma executed its early sales motion

(32:27) Why Figma changed its customer narrative

(34:03) Building outbound sales strategy at Figma

(36:17) Segmented pricing and no discounts

(41:55) Kyle’s transition from Dropbox to Figma

(47:25) Creating a world-class sales culture

(51:46) How Figma does sales differently

(54:02) Building the initial sales team around a passion for the product

(57:12) Figma’s unique hiring process for salespeople

(60:40) Advice for founders hiring their first salesperson

(63:18) The secret to Dylan Field’s success

(64:33) How to scale yourself as an early hire

(66:25) Oliver Jay’s impact on Kyle

]]> 4078 The new PLG playbook | Arming the next generation of product-led companies | Oliver Jay (Asana, Dropbox) Oliver Jay is a sales and expansion specialist. Oliver was Chief Revenue Officer at Asana and led the company’s global expansion. He grew the team from 20 to 450 people and increased international income to 40% of Asana’s total revenue. Prior to this, Oliver built the first business sales team at Dropbox, and led the company’s expansion into the Asia-Pacific region while tripling ARR. Oliver is now an advisor and leadership coach focused on assisting founders and executives in scaling their businesses. — In today’s episode, we discuss: Common mistakes PLG companies make The “PLG trap” and how to avoid it The playbook for transitioning into enterprise How and when to build an enterprise sales team How PLG companies can break $10 billion market cap Why it’s difficult to emulate Atlassian, Slack or Salesforce — Referenced: Airtable: https://www.airtable.com/ Asana: https://asana.com/ Atlassian: https://www.atlassian.com/ Bitbucket: https://bitbucket.org/product/ Confluent: https://www.confluent.io/ Daniel Shapero: https://www.linkedin.com/in/dshapero/ Datadog: https://www.datadoghq.com/ Dennis Woodside: https://www.linkedin.com/in/dennis-woodside-341302/ Dropbox: https://www.dropbox.com/ Dustin Moskovitz: https://www.linkedin.com/in/dmoskov/ Jay Simons: https://www.linkedin.com/in/jaysimons/ Jira: https://www.atlassian.com/software/jira Justin Rosenstein: https://www.linkedin.com/in/justinrosenstein/ Kim Scott: https://www.linkedin.com/in/kimm4/ Salesforce: https://www.salesforce.com/ Slack: https://slack.com/ The PLG Trap: https://www.linkedin.com/pulse/plg-trap-oliver-jay/ The seed, land, and expand framework: https://www.endgame.io/blog/seed-land-expand-framework Zendesk: https://www.zendesk.com/ — Where to find Oliver Jay: LinkedIn: https://www.linkedin.com/in/oliverjayleadership/ Website: https://www.oliverjayleadership.com/ — Where to find Brett Berson: Twitter/X: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094 — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:23) Differences between PLG and enterprise companies (05:56) Avoiding the “PLG trap” (07:39) Transitioning to enterprise feels like building two companies (10:57) Thinking about user value versus company value (13:58) The relationship between OKRs and executive champions (14:59) Dropbox had almost no company value (15:33) The strategy PLG companies should avoid (18:30) Why Dropbox is worth $10b, not $50b (19:41) The story of Asana’s expansion (21:16) Asana’s unique customer success team (23:27) How product strategy relates to finding champions (25:03) How Asana structured its GTM org (27:11) What Oliver would have done differently with Asana’s GTM (29:45) Getting executive-level buy-in (31:49) Asana’s concept of “selling clarity” (33:18) An inside look at Asana’s transition into enterprise (37:59) The champion tree framework (40:43) Structuring Asana’s early enterprise sales team (44:27) The impact of company size on GTM (47:20) Common sales mistake (48:29) The seed, land, and expand framework (51:43) Oliver’s advice to founders (54:13) Why building horizontally may be a mistake (55:32) Common challenges faced by PLG companies (58:30) How PLG companies can break the $10b market cap (60:17) Why emulating Atlassian’s playbook is difficult (63:21) People who had an outsized impact on Oliver Thu, 04 Jan 2024 12:00:00 -0000 The new PLG playbook | Arming the next generation of product-led companies | Oliver Jay (Asana, Dropbox) full First Round Oliver Jay is a sales and expansion specialist. Oliver was Chief Revenue Officer at Asana and led the company’s global expansion. He grew the team from 20 to 450 people and increased international income to 40% of Asana’s total revenue. Prior to this, Oliver built the first business sales team at Dropbox, and led the company’s expansion into the Asia-Pacific region while tripling ARR. Oliver is now an advisor and leadership coach focused on assisting founders and executives in scaling their businesses. Oliver Jay is a sales and expansion specialist. Oliver was Chief Revenue Officer at Asana and led the company’s global expansion. He grew the team from 20 to 450 people and increased international income to 40% of Asana’s total revenue. Prior to this, Oliver built the first business sales team at Dropbox, and led the company’s expansion into the Asia-Pacific region while tripling ARR. Oliver is now an advisor and leadership coach focused on assisting founders and executives in scaling their businesses. — In today’s episode, we discuss: Common mistakes PLG companies make The “PLG trap” and how to avoid it The playbook for transitioning into enterprise How and when to build an enterprise sales team How PLG companies can break $10 billion market cap Why it’s difficult to emulate Atlassian, Slack or Salesforce — Referenced: Airtable: https://www.airtable.com/ Asana: https://asana.com/ Atlassian: https://www.atlassian.com/ Bitbucket: https://bitbucket.org/product/ Confluent: https://www.confluent.io/ Daniel Shapero: https://www.linkedin.com/in/dshapero/ Datadog: https://www.datadoghq.com/ Dennis Woodside: https://www.linkedin.com/in/dennis-woodside-341302/ Dropbox: https://www.dropbox.com/ Dustin Moskovitz: https://www.linkedin.com/in/dmoskov/ Jay Simons: https://www.linkedin.com/in/jaysimons/ Jira: https://www.atlassian.com/software/jira Justin Rosenstein: https://www.linkedin.com/in/justinrosenstein/ Kim Scott: https://www.linkedin.com/in/kimm4/ Salesforce: https://www.salesforce.com/ Slack: https://slack.com/ The PLG Trap: https://www.linkedin.com/pulse/plg-trap-oliver-jay/ The seed, land, and expand framework: https://www.endgame.io/blog/seed-land-expand-framework Zendesk: https://www.zendesk.com/ — Where to find Oliver Jay: LinkedIn: https://www.linkedin.com/in/oliverjayleadership/ Website: https://www.oliverjayleadership.com/ — Where to find Brett Berson: Twitter/X: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094 — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:23) Differences between PLG and enterprise companies (05:56) Avoiding the “PLG trap” (07:39) Transitioning to enterprise feels like building two companies (10:57) Thinking about user value versus company value (13:58) The relationship between OKRs and executive champions (14:59) Dropbox had almost no company value (15:33) The strategy PLG companies should avoid (18:30) Why Dropbox is worth $10b, not $50b (19:41) The story of Asana’s expansion (21:16) Asana’s unique customer success team (23:27) How product strategy relates to finding champions (25:03) How Asana structured its GTM org (27:11) What Oliver would have done differently with Asana’s GTM (29:45) Getting executive-level buy-in (31:49) Asana’s concept of “selling clarity” (33:18) An inside look at Asana’s transition into enterprise (37:59) The champion tree framework (40:43) Structuring Asana’s early enterprise sales team (44:27) The impact of company size on GTM (47:20) Common sales mistake (48:29) The seed, land, and expand framework (51:43) Oliver’s advice to founders (54:13) Why building horizontally may be a mistake (55:32) Common challenges faced by PLG companies (58:30) How PLG companies can break the $10b market cap (60:17) Why emulating Atlassian’s playbook is difficult (63:21) People who had an outsized impact on Oliver Oliver Jay is a sales and expansion specialist. Oliver was Chief Revenue Officer at Asana and led the company’s global expansion. He grew the team from 20 to 450 people and increased international income to 40% of Asana’s total revenue. Prior to this, Oliver built the first business sales team at Dropbox, and led the company’s expansion into the Asia-Pacific region while tripling ARR. Oliver is now an advisor and leadership coach focused on assisting founders and executives in scaling their businesses.

—

In today’s episode, we discuss:

  • Common mistakes PLG companies make
  • The “PLG trap” and how to avoid it
  • The playbook for transitioning into enterprise
  • How and when to build an enterprise sales team
  • How PLG companies can break $10 billion market cap
  • Why it’s difficult to emulate Atlassian, Slack or Salesforce

—

Referenced:

—

Where to find Oliver Jay:

—

Where to find Brett Berson:

—

Where to find First Round Capital:

—

Timestamps:

(00:00) Introduction

(02:23) Differences between PLG and enterprise companies

(05:56) Avoiding the “PLG trap”

(07:39) Transitioning to enterprise feels like building two companies

(10:57) Thinking about user value versus company value

(13:58) The relationship between OKRs and executive champions

(14:59) Dropbox had almost no company value

(15:33) The strategy PLG companies should avoid

(18:30) Why Dropbox is worth $10b, not $50b

(19:41) The story of Asana’s expansion

(21:16) Asana’s unique customer success team

(23:27) How product strategy relates to finding champions

(25:03) How Asana structured its GTM org

(27:11) What Oliver would have done differently with Asana’s GTM

(29:45) Getting executive-level buy-in

(31:49) Asana’s concept of “selling clarity”

(33:18) An inside look at Asana’s transition into enterprise

(37:59) The champion tree framework

(40:43) Structuring Asana’s early enterprise sales team

(44:27) The impact of company size on GTM

(47:20) Common sales mistake

(48:29) The seed, land, and expand framework

(51:43) Oliver’s advice to founders

(54:13) Why building horizontally may be a mistake

(55:32) Common challenges faced by PLG companies

(58:30) How PLG companies can break the $10b market cap

(60:17) Why emulating Atlassian’s playbook is difficult

(63:21) People who had an outsized impact on Oliver

]]> 3918 Mastering modern entrepreneurship | Building lean, starting young, and studying customers | Steve Blank (Author of The Four Steps to the Epiphany) Steve Blank, an Adjunct Professor at Stanford University, is widely regarded as the father of modern entrepreneurship. Prior to academia, Steve’s career spanned eight different startups. Credited with launching the Lean Startup movement with his May 2013 Harvard Business Review cover story, Steve has changed how startups are built, and how entrepreneurship is taught. Steve is also the renowned author of The Four Steps to the Epiphany and The Startup Owner’s Manual. — In today’s episode, we discuss: Why there aren’t more successful startups How to improve entrepreneurship in the USA Misunderstood aspects of the Lean Startup methodology Common traits shared by outlier founders Why successful entrepreneurs are irrational (and need to be) How founders can transition to CEOs Why some second-time founders fail Building in existing versus new markets The Four Steps to the Epiphany in 2023 — Referenced: Alexander Osterwalder: https://www.linkedin.com/in/osterwalder Allen Michels: https://en.wikipedia.org/wiki/Allen_Michels Ben Wegbreit, Co-founder of E.piphany: https://www.linkedin.com/in/ben-wegbreit-22192/ Convergent Technologies: https://en.wikipedia.org/wiki/Convergent_Technologies Eric Ries: https://www.linkedin.com/in/eries/ Gordon Bell: https://www.linkedin.com/in/gordon-bell-3035b43/ JB Straubel: https://www.linkedin.com/in/jb-straubel-b694981/ Kathy Eisenhardt: https://www.linkedin.com/in/kathleen-eisenhardt-5642247/ Roger Siboni, former CEO of E.piphany: https://theorg.com/org/coupa-software/org-chart/roger-siboni Satya Nadella: https://www.linkedin.com/in/satyanadella/ Steve Ballmer: https://www.linkedin.com/in/steve-ballmer-7087a8157/ The lean launchpad at Stanford: https://steveblank.com/2011/05/10/the-lean-launchpad-at-stanford-–-the-final-presentations/ The semiconductor industry - explained: https://steveblank.com/2022/01/25/the-semiconductor-ecosystem/ The three pillars of world class corporate innovation: https://steveblank.com/2022/11/11/the-three-pillars-of-world-class-corporate-innovation/ Tina Seelig: https://www.linkedin.com/in/tinaseelig/ Tom Mueller, Ex-SpaceX Propulsion CTO: https://www.linkedin.com/in/thomas-mueller-2094513b/ Why corporate entrepreneurs are extraordinary: https://steveblank.com/2015/08/25/why-corporate-entrepreneurs-are-extraordinary-the-rebel-alliance/ Why entrepreneurs start companies rather than join them: https://steveblank.com/2018/04/11/why-entrepreneurs-start-companies-rather-than-join-them/ — Where to find Steve: LinkedIn: https://www.linkedin.com/in/steveblank/ Twitter/X: https://twitter.com/sgblank Website: https://steveblank.com/ — Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:20) Why there aren’t more successful startups (06:07) Outlier founders have similar childhoods (10:34) How to be a successful founder CEO (12:00) Why entrepreneurship should be taught in schools (16:39) The importance of curiosity (19:57) The role of instincts in entrepreneurship (22:31) Having profound beliefs in a vision (24:17) Building in existing versus new markets (29:09) What second-time founders can get wrong (33:49) Why founders need to be irrational (39:28) Common traits shared by outlier founders (45:05) Evaluating what makes a startup successful (49:44) Steve’s assessment of Satya Nadella at Microsoft (52:26) What it takes to build an incredible company (60:45) The Four Steps to the Epiphany in 2023 (64:36) The origins of The Four Steps to the Epiphany Thu, 21 Dec 2023 12:00:00 -0000 Mastering modern entrepreneurship | Building lean, starting young, and studying customers | Steve Blank (Author of The Four Steps to the Epiphany) full First Round Steve Blank, an Adjunct Professor at Stanford University, is widely regarded as the father of modern entrepreneurship. Prior to academia, Steve’s career spanned eight different startups. Credited with launching the Lean Startup movement with his May 2013 Harvard Business Review cover story, Steve has changed how startups are built, and how entrepreneurship is taught. Steve is also the renowned author of The Four Steps to the Epiphany and The Startup Owner’s Manual. Steve Blank, an Adjunct Professor at Stanford University, is widely regarded as the father of modern entrepreneurship. Prior to academia, Steve’s career spanned eight different startups. Credited with launching the Lean Startup movement with his May 2013 Harvard Business Review cover story, Steve has changed how startups are built, and how entrepreneurship is taught. Steve is also the renowned author of The Four Steps to the Epiphany and The Startup Owner’s Manual. — In today’s episode, we discuss: Why there aren’t more successful startups How to improve entrepreneurship in the USA Misunderstood aspects of the Lean Startup methodology Common traits shared by outlier founders Why successful entrepreneurs are irrational (and need to be) How founders can transition to CEOs Why some second-time founders fail Building in existing versus new markets The Four Steps to the Epiphany in 2023 — Referenced: Alexander Osterwalder: https://www.linkedin.com/in/osterwalder Allen Michels: https://en.wikipedia.org/wiki/Allen_Michels Ben Wegbreit, Co-founder of E.piphany: https://www.linkedin.com/in/ben-wegbreit-22192/ Convergent Technologies: https://en.wikipedia.org/wiki/Convergent_Technologies Eric Ries: https://www.linkedin.com/in/eries/ Gordon Bell: https://www.linkedin.com/in/gordon-bell-3035b43/ JB Straubel: https://www.linkedin.com/in/jb-straubel-b694981/ Kathy Eisenhardt: https://www.linkedin.com/in/kathleen-eisenhardt-5642247/ Roger Siboni, former CEO of E.piphany: https://theorg.com/org/coupa-software/org-chart/roger-siboni Satya Nadella: https://www.linkedin.com/in/satyanadella/ Steve Ballmer: https://www.linkedin.com/in/steve-ballmer-7087a8157/ The lean launchpad at Stanford: https://steveblank.com/2011/05/10/the-lean-launchpad-at-stanford-–-the-final-presentations/ The semiconductor industry - explained: https://steveblank.com/2022/01/25/the-semiconductor-ecosystem/ The three pillars of world class corporate innovation: https://steveblank.com/2022/11/11/the-three-pillars-of-world-class-corporate-innovation/ Tina Seelig: https://www.linkedin.com/in/tinaseelig/ Tom Mueller, Ex-SpaceX Propulsion CTO: https://www.linkedin.com/in/thomas-mueller-2094513b/ Why corporate entrepreneurs are extraordinary: https://steveblank.com/2015/08/25/why-corporate-entrepreneurs-are-extraordinary-the-rebel-alliance/ Why entrepreneurs start companies rather than join them: https://steveblank.com/2018/04/11/why-entrepreneurs-start-companies-rather-than-join-them/ — Where to find Steve: LinkedIn: https://www.linkedin.com/in/steveblank/ Twitter/X: https://twitter.com/sgblank Website: https://steveblank.com/ — Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:20) Why there aren’t more successful startups (06:07) Outlier founders have similar childhoods (10:34) How to be a successful founder CEO (12:00) Why entrepreneurship should be taught in schools (16:39) The importance of curiosity (19:57) The role of instincts in entrepreneurship (22:31) Having profound beliefs in a vision (24:17) Building in existing versus new markets (29:09) What second-time founders can get wrong (33:49) Why founders need to be irrational (39:28) Common traits shared by outlier founders (45:05) Evaluating what makes a startup successful (49:44) Steve’s assessment of Satya Nadella at Microsoft (52:26) What it takes to build an incredible company (60:45) The Four Steps to the Epiphany in 2023 (64:36) The origins of The Four Steps to the Epiphany Steve Blank, an Adjunct Professor at Stanford University, is widely regarded as the father of modern entrepreneurship. Prior to academia, Steve’s career spanned eight different startups. Credited with launching the Lean Startup movement with his May 2013 Harvard Business Review cover story, Steve has changed how startups are built, and how entrepreneurship is taught. Steve is also the renowned author of The Four Steps to the Epiphany and The Startup Owner’s Manual.

—

In today’s episode, we discuss:

  • Why there aren’t more successful startups
  • How to improve entrepreneurship in the USA
  • Misunderstood aspects of the Lean Startup methodology
  • Common traits shared by outlier founders
  • Why successful entrepreneurs are irrational (and need to be)
  • How founders can transition to CEOs
  • Why some second-time founders fail
  • Building in existing versus new markets
  • The Four Steps to the Epiphany in 2023

—

Referenced:

—

Where to find Steve:

—

Where to find Brett:

—

Where to find First Round Capital:

—

Timestamps:

(00:00) Introduction

(02:20) Why there aren’t more successful startups

(06:07) Outlier founders have similar childhoods

(10:34) How to be a successful founder CEO

(12:00) Why entrepreneurship should be taught in schools

(16:39) The importance of curiosity

(19:57) The role of instincts in entrepreneurship

(22:31) Having profound beliefs in a vision

(24:17) Building in existing versus new markets

(29:09) What second-time founders can get wrong

(33:49) Why founders need to be irrational

(39:28) Common traits shared by outlier founders

(45:05) Evaluating what makes a startup successful

(49:44) Steve’s assessment of Satya Nadella at Microsoft

(52:26) What it takes to build an incredible company

(60:45) The Four Steps to the Epiphany in 2023

(64:36) The origins of The Four Steps to the Epiphany

]]> 4183 Winning with open and closed source products | Neha Narkhede (Co-founder at Confluent and Oscilar) Neha Narkhede is a co-founder at Confluent, a data streaming software that raised at a $9.1b valuation in 2021. Neha later co-founded Oscilar, a no-code platform that helps companies detect and manage fraud. Before building these two companies, Neha was a Principal Software Engineer at LinkedIn where she co-created Apache Kafka. Neha is ranked #50 on Forbes’ list of “America’s Richest Self-Made Women 2023” with an estimated net worth of $520m. — In today’s episode we discuss: The origins of Confluent, Kafka, and Oscilar How to become a successful second-time founder Advice for monetizing open source product Neha’s unique GTM strategies How Confluent ran two businesses within one company Neha’s path to founder market fit — Referenced: Apache Kafka: https://kafka.apache.org/ Confluent: https://www.confluent.io/ Confluent Cloud: https://www.confluent.io/confluent-cloud/ Jay Kreps, co-founder at Confluent: https://www.linkedin.com/in/jaykreps/ Jun Rao, co-founder at Confluent: https://www.linkedin.com/in/junrao/ MongoDB: https://www.mongodb.com/ Oscilar: https://oscilar.com/ — Where to find Neha: LinkedIn: https://www.linkedin.com/in/nehanarkhede/ Twitter/X: https://twitter.com/nehanarkhede Website: https://www.nehanarkhede.com/ — Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:14)The origin story of Kafka (05:24) Co-creating Kafka at LinkedIn (07:31) Why open sourcing Kafka was a masterstroke (11:04) The unique nature of Confluent's Zero to One phase (16:35) Building for a specific customer early on (18:42) Inside Confluent’s successful launch (20:12) Establishing Confluent as an enterprise company (22:00) The role of developer evangelism in Confluent’s success (23:49) Using developer evangelism in category creation (26:41) Navigating early co-founder dynamics (30:06) Leveraging complementary founder skills (31:56) Advice for future founders (32:45) Building Confluent with monetization in mind (34:38) Monetizing open source products (36:05) GTM for subscription Saas versus consumption SaaS (39:48) The importance of founder-led GTM sales (40:58) Neha’s order of operations for GTM sales (42:33) When to build out outbound sales (45:28) Adding SaaS to a software business (49:48) Choosing what to license and what to open source (53:32) How Confluent’s co-founders decided on SaaS offering (57:58) Neha’s journey as a second-time founder (59:48) Building Oscilar differently to Confluent (64:15) Going from speculation to product realization (70:00) Solving problems people are willing to pay for (72:07) Neha’s “proactive research sprint” tactic (73:48) How Neha has applied this tactic Thu, 07 Dec 2023 12:00:00 -0000 Winning with open and closed source products | Neha Narkhede (Co-founder at Confluent and Oscilar) full First Round Neha Narkhede is a co-founder at Confluent, a data streaming software that raised at a $9.1b valuation in 2021. Neha later co-founded Oscilar, a no-code platform that helps companies detect and manage fraud. Before building these two companies, Neha was a Principal Software Engineer at LinkedIn where she co-created Apache Kafka. Neha is ranked #50 on Forbes’ list of “America’s Richest Self-Made Women 2023” with an estimated net worth of $520m. Neha Narkhede is a co-founder at Confluent, a data streaming software that raised at a $9.1b valuation in 2021. Neha later co-founded Oscilar, a no-code platform that helps companies detect and manage fraud. Before building these two companies, Neha was a Principal Software Engineer at LinkedIn where she co-created Apache Kafka. Neha is ranked #50 on Forbes’ list of “America’s Richest Self-Made Women 2023” with an estimated net worth of $520m. — In today’s episode we discuss: The origins of Confluent, Kafka, and Oscilar How to become a successful second-time founder Advice for monetizing open source product Neha’s unique GTM strategies How Confluent ran two businesses within one company Neha’s path to founder market fit — Referenced: Apache Kafka: https://kafka.apache.org/ Confluent: https://www.confluent.io/ Confluent Cloud: https://www.confluent.io/confluent-cloud/ Jay Kreps, co-founder at Confluent: https://www.linkedin.com/in/jaykreps/ Jun Rao, co-founder at Confluent: https://www.linkedin.com/in/junrao/ MongoDB: https://www.mongodb.com/ Oscilar: https://oscilar.com/ — Where to find Neha: LinkedIn: https://www.linkedin.com/in/nehanarkhede/ Twitter/X: https://twitter.com/nehanarkhede Website: https://www.nehanarkhede.com/ — Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:14)The origin story of Kafka (05:24) Co-creating Kafka at LinkedIn (07:31) Why open sourcing Kafka was a masterstroke (11:04) The unique nature of Confluent's Zero to One phase (16:35) Building for a specific customer early on (18:42) Inside Confluent’s successful launch (20:12) Establishing Confluent as an enterprise company (22:00) The role of developer evangelism in Confluent’s success (23:49) Using developer evangelism in category creation (26:41) Navigating early co-founder dynamics (30:06) Leveraging complementary founder skills (31:56) Advice for future founders (32:45) Building Confluent with monetization in mind (34:38) Monetizing open source products (36:05) GTM for subscription Saas versus consumption SaaS (39:48) The importance of founder-led GTM sales (40:58) Neha’s order of operations for GTM sales (42:33) When to build out outbound sales (45:28) Adding SaaS to a software business (49:48) Choosing what to license and what to open source (53:32) How Confluent’s co-founders decided on SaaS offering (57:58) Neha’s journey as a second-time founder (59:48) Building Oscilar differently to Confluent (64:15) Going from speculation to product realization (70:00) Solving problems people are willing to pay for (72:07) Neha’s “proactive research sprint” tactic (73:48) How Neha has applied this tactic Neha Narkhede is a co-founder at Confluent, a data streaming software that raised at a $9.1b valuation in 2021. Neha later co-founded Oscilar, a no-code platform that helps companies detect and manage fraud. Before building these two companies, Neha was a Principal Software Engineer at LinkedIn where she co-created Apache Kafka. Neha is ranked #50 on Forbes’ list of “America’s Richest Self-Made Women 2023” with an estimated net worth of $520m.

—

In today’s episode we discuss:

  • The origins of Confluent, Kafka, and Oscilar
  • How to become a successful second-time founder
  • Advice for monetizing open source product
  • Neha’s unique GTM strategies
  • How Confluent ran two businesses within one company
  • Neha’s path to founder market fit

—

Referenced:

—

Where to find Neha:

—

Where to find Brett:

—

Where to find First Round Capital:

—

Timestamps:

(00:00) Introduction

(02:14)The origin story of Kafka

(05:24) Co-creating Kafka at LinkedIn

(07:31) Why open sourcing Kafka was a masterstroke

(11:04) The unique nature of Confluent's Zero to One phase

(16:35) Building for a specific customer early on

(18:42) Inside Confluent’s successful launch

(20:12) Establishing Confluent as an enterprise company

(22:00) The role of developer evangelism in Confluent’s success

(23:49) Using developer evangelism in category creation

(26:41) Navigating early co-founder dynamics

(30:06) Leveraging complementary founder skills

(31:56) Advice for future founders

(32:45) Building Confluent with monetization in mind

(34:38) Monetizing open source products

(36:05) GTM for subscription Saas versus consumption SaaS

(39:48) The importance of founder-led GTM sales

(40:58) Neha’s order of operations for GTM sales

(42:33) When to build out outbound sales

(45:28) Adding SaaS to a software business

(49:48) Choosing what to license and what to open source

(53:32) How Confluent’s co-founders decided on SaaS offering

(57:58) Neha’s journey as a second-time founder

(59:48) Building Oscilar differently to Confluent

(64:15) Going from speculation to product realization

(70:00) Solving problems people are willing to pay for

(72:07) Neha’s “proactive research sprint” tactic

(73:48) How Neha has applied this tactic

]]> 4460 The Bard blueprint | Creating value, shipping fast, and advancing AI ethically | Jack Krawczyk (Google) Jack Krawczyk is a Senior Director of Product at Google, building Bard. Bard is Google’s collaborative, conversational, and experimental AI tool that’s bridging the gap between humans and bots, while addressing ethical considerations around AI. After joining the project in 2020, Jack helped ship Bard in less than four years. Bard sources information directly from the web, and now enables users to inquire about and summarize YouTube videos. — In today’s episode, we discuss: Key lessons from Bard’s development process Ethics in AI How Bard shipped fast What separates Bard from competitors The future of LLM, Generative AI, and AGI Advice for aspiring AI developers — Referenced: Bard: https://bard.google.com/ ChatGPT: https://chat.openai.com/ Duet AI: https://cloud.google.com/duet-ai Free courses on machine learning by Andrew Ng: https://www.andrewng.org/courses/ Google Assistant: https://assistant.google.com/ Introducing Google Assistant to Bard: https://blog.google/products/assistant/google-assistant-bard-generative-ai/ Large Language Model (LLM): https://en.wikipedia.org/wiki/Large_language_model Meena: https://blog.research.google/2020/01/towards-conversational-agent-that-can.html Sissie Hsiao (GM at Bard): https://www.linkedin.com/in/sissie-hsiao-b24243/ Steve Stoute: https://www.linkedin.com/in/stevestoute/ UnitedMasters: https://unitedmasters.com/ — Where to find Jack Krawczyk: Twitter/X: https://twitter.com/JackK LinkedIn: https://www.linkedin.com/in/jack--k — Where to find Brett Berson: Twitter/X: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:17) Bard’s origin story (03:54) Deciding on the application of Bard (05:59) The ethical considerations around building Bard (10:19) Why Bard launched to the public so early (13:30) Risk-taking at big companies versus smaller ones (16:20) Bard’s early user research (21:21) Bard versus ChatGPT (25:01) The cultural and product principles behind Bard (30:56) Insight into Bard’s impressive development speed (35:17) Deciding when to ship Bard (41:41) Why Bard is different from other products Jack has built (46:30) Evaluating Bard’s original spec (48:02) Insight into Bard's product roadmap (56:00) The toughest challenges Bard has faced (57:50) What’s special about team-building at Bard (62:54) Addressing Bard’s negative press (67:49) Advice for aspiring LLM companies (69:15) Advice for non-LLM companies (71:05) The biggest barriers to advancing AI (75:45) How product people can use or build with AI (77:24) How AI is changing product leadership (79:20) People who had an outsized impact on Jack Thu, 30 Nov 2023 12:00:00 -0000 The Bard blueprint | Creating value, shipping fast, and advancing AI ethically | Jack Krawczyk (Google) full First Round Jack Krawczyk is a Senior Director of Product at Google, building Bard. Bard is Google’s collaborative, conversational, and experimental AI tool that’s bridging the gap between humans and bots, while addressing ethical considerations around AI. After joining the project in 2020, Jack helped ship Bard in less than four years. Bard sources information directly from the web, and now enables users to inquire about and summarize YouTube videos. Jack Krawczyk is a Senior Director of Product at Google, building Bard. Bard is Google’s collaborative, conversational, and experimental AI tool that’s bridging the gap between humans and bots, while addressing ethical considerations around AI. After joining the project in 2020, Jack helped ship Bard in less than four years. Bard sources information directly from the web, and now enables users to inquire about and summarize YouTube videos. — In today’s episode, we discuss: Key lessons from Bard’s development process Ethics in AI How Bard shipped fast What separates Bard from competitors The future of LLM, Generative AI, and AGI Advice for aspiring AI developers — Referenced: Bard: https://bard.google.com/ ChatGPT: https://chat.openai.com/ Duet AI: https://cloud.google.com/duet-ai Free courses on machine learning by Andrew Ng: https://www.andrewng.org/courses/ Google Assistant: https://assistant.google.com/ Introducing Google Assistant to Bard: https://blog.google/products/assistant/google-assistant-bard-generative-ai/ Large Language Model (LLM): https://en.wikipedia.org/wiki/Large_language_model Meena: https://blog.research.google/2020/01/towards-conversational-agent-that-can.html Sissie Hsiao (GM at Bard): https://www.linkedin.com/in/sissie-hsiao-b24243/ Steve Stoute: https://www.linkedin.com/in/stevestoute/ UnitedMasters: https://unitedmasters.com/ — Where to find Jack Krawczyk: Twitter/X: https://twitter.com/JackK LinkedIn: https://www.linkedin.com/in/jack--k — Where to find Brett Berson: Twitter/X: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:17) Bard’s origin story (03:54) Deciding on the application of Bard (05:59) The ethical considerations around building Bard (10:19) Why Bard launched to the public so early (13:30) Risk-taking at big companies versus smaller ones (16:20) Bard’s early user research (21:21) Bard versus ChatGPT (25:01) The cultural and product principles behind Bard (30:56) Insight into Bard’s impressive development speed (35:17) Deciding when to ship Bard (41:41) Why Bard is different from other products Jack has built (46:30) Evaluating Bard’s original spec (48:02) Insight into Bard's product roadmap (56:00) The toughest challenges Bard has faced (57:50) What’s special about team-building at Bard (62:54) Addressing Bard’s negative press (67:49) Advice for aspiring LLM companies (69:15) Advice for non-LLM companies (71:05) The biggest barriers to advancing AI (75:45) How product people can use or build with AI (77:24) How AI is changing product leadership (79:20) People who had an outsized impact on Jack Jack Krawczyk is a Senior Director of Product at Google, building Bard. Bard is Google’s collaborative, conversational, and experimental AI tool that’s bridging the gap between humans and bots, while addressing ethical considerations around AI. After joining the project in 2020, Jack helped ship Bard in less than four years. Bard sources information directly from the web, and now enables users to inquire about and summarize YouTube videos.

—

In today’s episode, we discuss:

  • Key lessons from Bard’s development process
  • Ethics in AI
  • How Bard shipped fast
  • What separates Bard from competitors
  • The future of LLM, Generative AI, and AGI
  • Advice for aspiring AI developers

—

Referenced:

—

Where to find Jack Krawczyk:

—

Where to find Brett Berson:

—

Where to find First Round Capital:

—

Timestamps:

(00:00) Introduction

(02:17) Bard’s origin story

(03:54) Deciding on the application of Bard

(05:59) The ethical considerations around building Bard

(10:19) Why Bard launched to the public so early

(13:30) Risk-taking at big companies versus smaller ones

(16:20) Bard’s early user research

(21:21) Bard versus ChatGPT

(25:01) The cultural and product principles behind Bard

(30:56) Insight into Bard’s impressive development speed

(35:17) Deciding when to ship Bard

(41:41) Why Bard is different from other products Jack has built

(46:30) Evaluating Bard’s original spec

(48:02) Insight into Bard's product roadmap

(56:00) The toughest challenges Bard has faced

(57:50) What’s special about team-building at Bard

(62:54) Addressing Bard’s negative press

(67:49) Advice for aspiring LLM companies

(69:15) Advice for non-LLM companies

(71:05) The biggest barriers to advancing AI

(75:45) How product people can use or build with AI

(77:24) How AI is changing product leadership

(79:20) People who had an outsized impact on Jack

]]> 5027 A masterclass in engineering leadership from Carta, Stripe, Uber, and Calm | Will Larson (CTO at Carta) Will Larson is the CTO at Carta, an ownership and equity management platform that raised at a $7.4b valuation in 2021. Prior to joining Carta, Will was CTO at Calm, founded Stripe's Foundation Engineering org, and led Uber’s Platform Engineering people and strategy. Will also writes extensively about engineering leadership, and has authored two books in this area: Staff Engineer, and An Elegant Puzzle. — In today’s episode we discuss: How to form an engineering strategy Common engineering management mistakes, and how to avoid them Advice for explaining, measuring, and optimizing engineering velocity Will’s nuanced approach to organizational policies Why it’s sometimes counterproductive to tell someone not to micromanage — Referenced: Accelerate (book): https://www.amazon.com/Accelerate-Software-Performing-Technology-Organizations/dp/1942788339 Calm: https://www.calm.com/ Carta: https://www.carta.com/ DORA: https://dora.dev/ Good Strategy, Bad Strategy (book): https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239 JavaScript: https://www.javascript.com/ KAFKA: https://kafka.apache.org/ Minto Pyramid (framework): https://untools.co/minto-pyramid Ruby on Rails: https://rubyonrails.org/ SPACE (framework): https://queue.acm.org/detail.cfm Stripe: https://www.stripe.com/ — Where to find Brett Berson: Twitter/X: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ — Where to find Will Larson: Twitter/X: https://twitter.com/lethain LinkedIn: https://www.linkedin.com/in/will-larson-a44b543/ Personal website/blog: https://lethain.com/ An Elegant Puzzle (book): https://www.amazon.com/Elegant-Puzzle-Systems-Engineering-Management/dp/1732265186 Staff Engineer (book): https://staffeng.com/book — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (03:03) The nuances of taking lessons from old companies (14:28) The value of writing down engineering principles (17:03) How to structure a strategy document (18:48) The 2 parts of any engineering strategy (21:08) Advice for turning strategy into action (23:44) Carta's unique "navigator" model (24:50) The Hidden Variable Problem (29:59) Explaining, measuring, and optimizing velocity (35:28) Useful metrics for engineering orgs (39:08) The balance between micromanagement and understanding details (43:03) Management anti-patterns (45:49) How to execute policies whilst managing their exceptions (47:56) What an excellent engineering executive looks like (53:53) How Will has evolved as an engineering executive (56:56) How to communicate with executives (63:18) Things that derail meetings (66:10) How to approach presentation feedback (67:30) A bad sign when working with direct reports (69:13) Advice for growing as an early-career engineer (71:11) Will's model for developing engineering teams (74:33) Sources of inspiration for Will's views on engineering management Thu, 16 Nov 2023 12:00:00 -0000 A masterclass in engineering leadership from Carta, Stripe, Uber, and Calm | Will Larson (CTO at Carta) full First Round Will Larson is the CTO at Carta, an ownership and equity management platform that raised at a $7.4b valuation in 2021. Prior to joining Carta, Will was CTO at Calm, founded Stripe's Foundation Engineering org, and led Uber’s Platform Engineering people and strategy. Will also writes extensively about engineering leadership, and has authored two books in this area: Staff Engineer, and An Elegant Puzzle. Will Larson is the CTO at Carta, an ownership and equity management platform that raised at a $7.4b valuation in 2021. Prior to joining Carta, Will was CTO at Calm, founded Stripe's Foundation Engineering org, and led Uber’s Platform Engineering people and strategy. Will also writes extensively about engineering leadership, and has authored two books in this area: Staff Engineer, and An Elegant Puzzle. — In today’s episode we discuss: How to form an engineering strategy Common engineering management mistakes, and how to avoid them Advice for explaining, measuring, and optimizing engineering velocity Will’s nuanced approach to organizational policies Why it’s sometimes counterproductive to tell someone not to micromanage — Referenced: Accelerate (book): https://www.amazon.com/Accelerate-Software-Performing-Technology-Organizations/dp/1942788339 Calm: https://www.calm.com/ Carta: https://www.carta.com/ DORA: https://dora.dev/ Good Strategy, Bad Strategy (book): https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239 JavaScript: https://www.javascript.com/ KAFKA: https://kafka.apache.org/ Minto Pyramid (framework): https://untools.co/minto-pyramid Ruby on Rails: https://rubyonrails.org/ SPACE (framework): https://queue.acm.org/detail.cfm Stripe: https://www.stripe.com/ — Where to find Brett Berson: Twitter/X: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ — Where to find Will Larson: Twitter/X: https://twitter.com/lethain LinkedIn: https://www.linkedin.com/in/will-larson-a44b543/ Personal website/blog: https://lethain.com/ An Elegant Puzzle (book): https://www.amazon.com/Elegant-Puzzle-Systems-Engineering-Management/dp/1732265186 Staff Engineer (book): https://staffeng.com/book — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (03:03) The nuances of taking lessons from old companies (14:28) The value of writing down engineering principles (17:03) How to structure a strategy document (18:48) The 2 parts of any engineering strategy (21:08) Advice for turning strategy into action (23:44) Carta's unique "navigator" model (24:50) The Hidden Variable Problem (29:59) Explaining, measuring, and optimizing velocity (35:28) Useful metrics for engineering orgs (39:08) The balance between micromanagement and understanding details (43:03) Management anti-patterns (45:49) How to execute policies whilst managing their exceptions (47:56) What an excellent engineering executive looks like (53:53) How Will has evolved as an engineering executive (56:56) How to communicate with executives (63:18) Things that derail meetings (66:10) How to approach presentation feedback (67:30) A bad sign when working with direct reports (69:13) Advice for growing as an early-career engineer (71:11) Will's model for developing engineering teams (74:33) Sources of inspiration for Will's views on engineering management Will Larson is the CTO at Carta, an ownership and equity management platform that raised at a $7.4b valuation in 2021. Prior to joining Carta, Will was CTO at Calm, founded Stripe's Foundation Engineering org, and led Uber’s Platform Engineering people and strategy. Will also writes extensively about engineering leadership, and has authored two books in this area: Staff Engineer, and An Elegant Puzzle.

—

In today’s episode we discuss:

  • How to form an engineering strategy
  • Common engineering management mistakes, and how to avoid them
  • Advice for explaining, measuring, and optimizing engineering velocity
  • Will’s nuanced approach to organizational policies
  • Why it’s sometimes counterproductive to tell someone not to micromanage

—

Referenced:

—

Where to find Brett Berson:

—

Where to find Will Larson:

—

Where to find First Round Capital:

—

Timestamps:

(00:00) Introduction

(03:03) The nuances of taking lessons from old companies

(14:28) The value of writing down engineering principles

(17:03) How to structure a strategy document

(18:48) The 2 parts of any engineering strategy

(21:08) Advice for turning strategy into action

(23:44) Carta's unique "navigator" model

(24:50) The Hidden Variable Problem

(29:59) Explaining, measuring, and optimizing velocity

(35:28) Useful metrics for engineering orgs

(39:08) The balance between micromanagement and understanding details

(43:03) Management anti-patterns

(45:49) How to execute policies whilst managing their exceptions

(47:56) What an excellent engineering executive looks like

(53:53) How Will has evolved as an engineering executive

(56:56) How to communicate with executives

(63:18) Things that derail meetings

(66:10) How to approach presentation feedback

(67:30) A bad sign when working with direct reports

(69:13) Advice for growing as an early-career engineer

(71:11) Will's model for developing engineering teams

(74:33) Sources of inspiration for Will's views on engineering management

]]> 4734 How goal-setting and planning is different for AI products | Anastasis Germanidis (Co-Founder & CTO at Runway) Anastasis Germanidis is the Co-Founder & CTO at Runway, an applied AI research company shaping the next era of art, entertainment, and human creativity. Runway has raised $237m and was one of Time Magazine’s “100 most influential companies” in 2023. Runway has been a persistent viral sensation in recent years, and is behind many of the most famous AI demos online. — In today’s episode we discuss: The origins of Runway The limitations of being “customer-driven” when building in AI How Runway balances research development with product development How goal-setting and planning is different for AI products Advice for early-stage AI founders — Referenced: Containerization: https://aws.amazon.com/what-is/containerization/ Docker: https://www.docker.com/ Green screen tool by Runway: https://runwayml.com/green-screen/ Hugging Face: https://huggingface.co/ Hugging Face Spaces: https://huggingface.co/spaces Hugging Face Model Hub: https://huggingface.co/docs/hub/models-the-hub Replicate: https://replicate.com/ Runway Gen-1: https://research.runwayml.com/gen1 Runway Gen-2: https://research.runwayml.com/gen2 Runway’s 30 AI Magic Tools: https://runwayml.com/ai-magic-tools/ — Where to find Anastasis Germanidis: Twitter/X: https://twitter.com/agermanidis LinkedIn: https://www.linkedin.com/in/agermanidis Personal website: https://agermanidis.com/ Personal blog: https://blog.agermanidis.com/ — Where to find Todd Jackson: Twitter/X: https://twitter.com/tjack LinkedIn: https://www.linkedin.com/in/toddj0 — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (03:23) The unique story of how Runway's co-founders met (08:27) The origins of Runway (09:28) Forming the initial product (13:55) Turning Runway into a company (14:41)Approach to initial market segments (18:53) Early-adopters (21:20) The limitations of being “customer-driven” (25:54) Forming a vocal community (27:08) Fostering community (29:05) The progression of Runway's tech and use-cases (33:08) How they picked users for early release (34:00) Expanding past the first 100 users of Gen-2 (35:33) Runway’s approach to safety and content moderation (36:44) Balancing product development and research development (43:51) Runway's org structure (45:08) Goal-setting amidst constant change in AI (46:50) Why Runway doesn't plan very far ahead (50:26) Advice to early-stage AI founders (53:11) Will AI replace video editors? (55:04) When Runway had the most momentum (56:49) Anastasis' #1 piece of advice Thu, 09 Nov 2023 12:00:00 -0000 How goal-setting and planning is different for AI products | Anastasis Germanidis (Co-Founder & CTO at Runway) full First Round Anastasis Germanidis is the Co-Founder & CTO at Runway, an applied AI research company shaping the next era of art, entertainment, and human creativity. Runway has raised $237m and was one of Time Magazine’s “100 most influential companies” in 2023. Runway has been a persistent viral sensation in recent years, and is behind many of the most famous AI demos online. Anastasis Germanidis is the Co-Founder & CTO at Runway, an applied AI research company shaping the next era of art, entertainment, and human creativity. Runway has raised $237m and was one of Time Magazine’s “100 most influential companies” in 2023. Runway has been a persistent viral sensation in recent years, and is behind many of the most famous AI demos online. — In today’s episode we discuss: The origins of Runway The limitations of being “customer-driven” when building in AI How Runway balances research development with product development How goal-setting and planning is different for AI products Advice for early-stage AI founders — Referenced: Containerization: https://aws.amazon.com/what-is/containerization/ Docker: https://www.docker.com/ Green screen tool by Runway: https://runwayml.com/green-screen/ Hugging Face: https://huggingface.co/ Hugging Face Spaces: https://huggingface.co/spaces Hugging Face Model Hub: https://huggingface.co/docs/hub/models-the-hub Replicate: https://replicate.com/ Runway Gen-1: https://research.runwayml.com/gen1 Runway Gen-2: https://research.runwayml.com/gen2 Runway’s 30 AI Magic Tools: https://runwayml.com/ai-magic-tools/ — Where to find Anastasis Germanidis: Twitter/X: https://twitter.com/agermanidis LinkedIn: https://www.linkedin.com/in/agermanidis Personal website: https://agermanidis.com/ Personal blog: https://blog.agermanidis.com/ — Where to find Todd Jackson: Twitter/X: https://twitter.com/tjack LinkedIn: https://www.linkedin.com/in/toddj0 — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (03:23) The unique story of how Runway's co-founders met (08:27) The origins of Runway (09:28) Forming the initial product (13:55) Turning Runway into a company (14:41)Approach to initial market segments (18:53) Early-adopters (21:20) The limitations of being “customer-driven” (25:54) Forming a vocal community (27:08) Fostering community (29:05) The progression of Runway's tech and use-cases (33:08) How they picked users for early release (34:00) Expanding past the first 100 users of Gen-2 (35:33) Runway’s approach to safety and content moderation (36:44) Balancing product development and research development (43:51) Runway's org structure (45:08) Goal-setting amidst constant change in AI (46:50) Why Runway doesn't plan very far ahead (50:26) Advice to early-stage AI founders (53:11) Will AI replace video editors? (55:04) When Runway had the most momentum (56:49) Anastasis' #1 piece of advice Anastasis Germanidis is the Co-Founder & CTO at Runway, an applied AI research company shaping the next era of art, entertainment, and human creativity. Runway has raised $237m and was one of Time Magazine’s “100 most influential companies” in 2023. Runway has been a persistent viral sensation in recent years, and is behind many of the most famous AI demos online.

—

In today’s episode we discuss:

  • The origins of Runway
  • The limitations of being “customer-driven” when building in AI
  • How Runway balances research development with product development
  • How goal-setting and planning is different for AI products
  • Advice for early-stage AI founders

—

Referenced:

—

Where to find Anastasis Germanidis:

—

Where to find Todd Jackson:

—

Where to find First Round Capital:

—

Timestamps:

(00:00) Introduction

(03:23) The unique story of how Runway's co-founders met

(08:27) The origins of Runway

(09:28) Forming the initial product

(13:55) Turning Runway into a company

(14:41)Approach to initial market segments

(18:53) Early-adopters

(21:20) The limitations of being “customer-driven”

(25:54) Forming a vocal community

(27:08) Fostering community

(29:05) The progression of Runway's tech and use-cases

(33:08) How they picked users for early release

(34:00) Expanding past the first 100 users of Gen-2

(35:33) Runway’s approach to safety and content moderation

(36:44) Balancing product development and research development

(43:51) Runway's org structure

(45:08) Goal-setting amidst constant change in AI

(46:50) Why Runway doesn't plan very far ahead

(50:26) Advice to early-stage AI founders

(53:11) Will AI replace video editors?

(55:04) When Runway had the most momentum

(56:49) Anastasis' #1 piece of advice

]]> 3556 How Vercel found extreme product-market fit by focusing on simplification | Guillermo Rauch (Vercel's CEO) Guillermo Rauch is the CEO of Vercel, a frontend-as-a-service product that was valued at $2.5b in 2021. Vercel serves customers like Uber, Notion and Zapier, and their React framework - Next.js - is used by over 500,000 developers and designers worldwide. Guillermo started his first company at age 11 in Buenos Aires and moved to San Francisco at age 18. In 2013, he sold his company Cloudup to Automattic (the company behind WordPress), and in 2015 he founded Vercel. — In today’s episode we discuss: Guillermo’s fascinating path into tech Learnings from building Cloudup and selling the company to Automattic (the company behind WordPress) Vercel’s origin story and path to product market fit How to make an open source business successful Vercel’s unique philosophy on developer experience Insights and predictions on the future of AI — Referenced: Algolia: https://www.algolia.com/ Apache Zookeeper: https://zookeeper.apache.org/ Apache Kafka: https://kafka.apache.org/ AWS: https://www.aws.training/ C++: https://www.techtarget.com/searchdatamanagement/definition/C Clerk: https://clerk-tech.com/ Cloudup: https://cloudup.com/ Commerce Cloud: https://www.salesforce.com/products/commerce/ Contentful: https://www.contentful.com/ Debian: https://www.debian.org/ Fintool: https://www.fintool.com/ Figma: https://www.figma.com/ GitLab: https://about.gitlab.com/ IRC: https://en.wikipedia.org/wiki/Internet_Relay_Chat KDE: https://kde.org/ Linux: https://en.wikipedia.org/wiki/Linux Mozilla: https://www.mozilla.org MooTools (UI library): https://mootools.net/ Next.js: https://nextjs.org/ React Native: https://reactnative.dev/ Red Hat: https://www.redhat.com/ Redpanda: https://redpanda.com/ Resend: https://resend.com/ Rust: https://www.rust-lang.org/ Salesforce: https://www.salesforce.com Servo: https://servo.org/ Shopify: https://www.shopify.com/ Socket.io: https://socket.io/ Symphony: https://symphony.com/ Trilio: https://trilio.io/ Twilio: https://www.twilio.com Vercel: https://vercel.com/ V0.dev: https://v0.dev/ — Where to find Guillermo: Twitter/x: https://twitter.com/rauchg LinkedIn: https://www.linkedin.com/in/rauchg/ Personal website: https://rauchg.com/ — Where to find Todd Jackson: Twitter: https://twitter.com/tjack LinkedIn: https://www.linkedin.com/in/toddj0 — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (02:35) Becoming an “internet celebrity” at age 11 (08:30) Guillermo's first company: Cloudup (11:09) Biggest learnings from Cloudup and WordPress (15:06) The insights behind starting Vercel (17:11) Sources of validation for Vercel (20:29) How Vercel formed its V1 product (23:25) Navigating the early reactions from competitors and users (25:58) The paradox of developers and how it impacted Next.js (31:20) Advice on finding product market fit (34:48) The forces behind a trend towards "Front-end Cloud” (38:35) Why people now pay so much attention to the front-end (40:06) How to make an open source business successful (44:54) Insights on product positioning and category creation (48:52) Vercel's journey through becoming multi-product (51:44) Guillermo's take on the future of AI (53:43) Heuristics for building better product experiences (55:49) AI insights from Vercel’s customers (57:37) How AI might change engineering in the next 10-20 years (62:43) Guillermo's favorite advice (65:45) Guillermo's advice to himself of 10 years ago Thu, 02 Nov 2023 08:00:00 -0000 How Vercel found extreme product-market fit by focusing on simplification | Guillermo Rauch (Vercel's CEO) full First Round Guillermo Rauch is the CEO of Vercel, a frontend-as-a-service product that was valued at $2.5b in 2021. Vercel serves customers like Uber, Notion and Zapier, and their React framework - Next.js - is used by over 500,000 developers and designers worldwide. Guillermo started his first company at age 11 in Buenos Aires and moved to San Francisco at age 18. In 2013, he sold his company Cloudup to Automattic (the company behind WordPress), and in 2015 he founded Vercel. Guillermo Rauch is the CEO of Vercel, a frontend-as-a-service product that was valued at $2.5b in 2021. Vercel serves customers like Uber, Notion and Zapier, and their React framework - Next.js - is used by over 500,000 developers and designers worldwide. Guillermo started his first company at age 11 in Buenos Aires and moved to San Francisco at age 18. In 2013, he sold his company Cloudup to Automattic (the company behind WordPress), and in 2015 he founded Vercel. — In today’s episode we discuss: Guillermo’s fascinating path into tech Learnings from building Cloudup and selling the company to Automattic (the company behind WordPress) Vercel’s origin story and path to product market fit How to make an open source business successful Vercel’s unique philosophy on developer experience Insights and predictions on the future of AI — Referenced: Algolia: https://www.algolia.com/ Apache Zookeeper: https://zookeeper.apache.org/ Apache Kafka: https://kafka.apache.org/ AWS: https://www.aws.training/ C++: https://www.techtarget.com/searchdatamanagement/definition/C Clerk: https://clerk-tech.com/ Cloudup: https://cloudup.com/ Commerce Cloud: https://www.salesforce.com/products/commerce/ Contentful: https://www.contentful.com/ Debian: https://www.debian.org/ Fintool: https://www.fintool.com/ Figma: https://www.figma.com/ GitLab: https://about.gitlab.com/ IRC: https://en.wikipedia.org/wiki/Internet_Relay_Chat KDE: https://kde.org/ Linux: https://en.wikipedia.org/wiki/Linux Mozilla: https://www.mozilla.org MooTools (UI library): https://mootools.net/ Next.js: https://nextjs.org/ React Native: https://reactnative.dev/ Red Hat: https://www.redhat.com/ Redpanda: https://redpanda.com/ Resend: https://resend.com/ Rust: https://www.rust-lang.org/ Salesforce: https://www.salesforce.com Servo: https://servo.org/ Shopify: https://www.shopify.com/ Socket.io: https://socket.io/ Symphony: https://symphony.com/ Trilio: https://trilio.io/ Twilio: https://www.twilio.com Vercel: https://vercel.com/ V0.dev: https://v0.dev/ — Where to find Guillermo: Twitter/x: https://twitter.com/rauchg LinkedIn: https://www.linkedin.com/in/rauchg/ Personal website: https://rauchg.com/ — Where to find Todd Jackson: Twitter: https://twitter.com/tjack LinkedIn: https://www.linkedin.com/in/toddj0 — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (02:35) Becoming an “internet celebrity” at age 11 (08:30) Guillermo's first company: Cloudup (11:09) Biggest learnings from Cloudup and WordPress (15:06) The insights behind starting Vercel (17:11) Sources of validation for Vercel (20:29) How Vercel formed its V1 product (23:25) Navigating the early reactions from competitors and users (25:58) The paradox of developers and how it impacted Next.js (31:20) Advice on finding product market fit (34:48) The forces behind a trend towards "Front-end Cloud” (38:35) Why people now pay so much attention to the front-end (40:06) How to make an open source business successful (44:54) Insights on product positioning and category creation (48:52) Vercel's journey through becoming multi-product (51:44) Guillermo's take on the future of AI (53:43) Heuristics for building better product experiences (55:49) AI insights from Vercel’s customers (57:37) How AI might change engineering in the next 10-20 years (62:43) Guillermo's favorite advice (65:45) Guillermo's advice to himself of 10 years ago Guillermo Rauch is the CEO of Vercel, a frontend-as-a-service product that was valued at $2.5b in 2021. Vercel serves customers like Uber, Notion and Zapier, and their React framework - Next.js - is used by over 500,000 developers and designers worldwide. Guillermo started his first company at age 11 in Buenos Aires and moved to San Francisco at age 18. In 2013, he sold his company Cloudup to Automattic (the company behind WordPress), and in 2015 he founded Vercel.

—

In today’s episode we discuss:

  • Guillermo’s fascinating path into tech
  • Learnings from building Cloudup and selling the company to Automattic (the company behind WordPress)
  • Vercel’s origin story and path to product market fit
  • How to make an open source business successful
  • Vercel’s unique philosophy on developer experience
  • Insights and predictions on the future of AI

—

Referenced:

  • Algolia: https://www.algolia.com/
  • Apache Zookeeper: https://zookeeper.apache.org/
  • Apache Kafka: https://kafka.apache.org/
  • AWS: https://www.aws.training/
  • C++: https://www.techtarget.com/searchdatamanagement/definition/C
  • Clerk: https://clerk-tech.com/
  • Cloudup: https://cloudup.com/
  • Commerce Cloud: https://www.salesforce.com/products/commerce/
  • Contentful: https://www.contentful.com/
  • Debian: https://www.debian.org/
  • Fintool: https://www.fintool.com/
  • Figma: https://www.figma.com/
  • GitLab: https://about.gitlab.com/
  • IRC: https://en.wikipedia.org/wiki/Internet_Relay_Chat
  • KDE: https://kde.org/
  • Linux: https://en.wikipedia.org/wiki/Linux
  • Mozilla: https://www.mozilla.org
  • MooTools (UI library): https://mootools.net/
  • Next.js: https://nextjs.org/
  • React Native: https://reactnative.dev/
  • Red Hat: https://www.redhat.com/
  • Redpanda: https://redpanda.com/
  • Resend: https://resend.com/
  • Rust: https://www.rust-lang.org/
  • Salesforce: https://www.salesforce.com
  • Servo: https://servo.org/
  • Shopify: https://www.shopify.com/
  • Socket.io: https://socket.io/
  • Symphony: https://symphony.com/
  • Trilio: https://trilio.io/
  • Twilio: https://www.twilio.com
  • Vercel: https://vercel.com/
  • V0.dev: https://v0.dev/

—

Where to find Guillermo:

  • Twitter/x: https://twitter.com/rauchg
  • LinkedIn: https://www.linkedin.com/in/rauchg/
  • Personal website: https://rauchg.com/

—

Where to find Todd Jackson:

  • Twitter: https://twitter.com/tjack
  • LinkedIn: https://www.linkedin.com/in/toddj0

—

Where to find First Round Capital:

  • Website: https://firstround.com/
  • First Round Review: https://review.firstround.com/
  • Twitter: https://twitter.com/firstround
  • Youtube: https://www.youtube.com/@FirstRoundCapital
  • This podcast on all platforms: https://review.firstround.com/podcast

—

Timestamps:

(02:35) Becoming an “internet celebrity” at age 11

(08:30) Guillermo's first company: Cloudup

(11:09) Biggest learnings from Cloudup and WordPress

(15:06) The insights behind starting Vercel

(17:11) Sources of validation for Vercel

(20:29) How Vercel formed its V1 product

(23:25) Navigating the early reactions from competitors and users

(25:58) The paradox of developers and how it impacted Next.js

(31:20) Advice on finding product market fit

(34:48) The forces behind a trend towards "Front-end Cloud”

(38:35) Why people now pay so much attention to the front-end

(40:06) How to make an open source business successful

(44:54) Insights on product positioning and category creation

(48:52) Vercel's journey through becoming multi-product

(51:44) Guillermo's take on the future of AI

(53:43) Heuristics for building better product experiences

(55:49) AI insights from Vercel’s customers

(57:37) How AI might change engineering in the next 10-20 years

(62:43) Guillermo's favorite advice

(65:45) Guillermo's advice to himself of 10 years ago

]]> 4021 The business of growing and monetizing an open source product | Ashley Kramer (GitLab CMO/CSO) Ashley Kramer is the CMO and CSO at GitLab, a publicly listed DevSecOps platform. Ashley took a unique path into her CMO role. She started out in software engineering before becoming a product leader, and eventually, a marketer. Most recently, Ashley was the CPO and CMO at Sisense, a data analytics company last valued at over $1b. — In today’s episode we discuss: How GitLab layered a commercial model on top of open source roots GitLab’s main marketing metrics Examples, benefits, and downsides of a transparent company culture How GitLab serves enterprise customers, and a passionate developer community Unique marketing lessons from working in an open core company An example of a recent marketing campaign — Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ — Where to find Ashley Kramer: Twitter/x: https://twitter.com/ashleyekramer LinkedIn: https://www.linkedin.com/in/ashleyekramer/ — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Referenced: CISO: https://www.cisco.com/c/en/us/products/security/what-is-ciso.html DevSecOps: https://about.gitlab.com/topics/devsecops/ E-Group: https://about.gitlab.com/company/team/e-group/ GitLab: https://gitlab.com GitLab legal team’s SAFE framework: https://about.gitlab.com/handbook/legal/safe-framework/ GitLab’s open core business model: https://handbook.gitlab.com/handbook/company/stewardship/ GitLab’s open source employee handbook: https://handbook.gitlab.com/handbook/people-group/ GitLab’s open source marketing handbook: https://about.gitlab.com/handbook/marketing/ GitLab’s open source remote handbook: https://handbook.gitlab.com/handbook/company/culture/all-remote/guide/ Sid Sijbrandij, CEO of GitLab: https://www.linkedin.com/in/sijbrandij/ Tableau: https://www.tableau.com/ — Timestamps: (00:00) Intro (02:34) Marketing in closed vs open source companies (07:40) The role of marketing at GitLab (09:23) The tensions of being a commercial, open source company (12:36) Advice for nurturing community and dealing with disagreements (15:02) GitLab's main marketing metrics (20:26) The thinking behind GitLab’s org structure, in and around marketing (28:19) Selling to enterprise as an open core company (29:53) The difference between open core and open source (30:39) Serving many different customer segments (35:10) GitLab's planning process (39:22) An example of GitLab’s marketing in practice (42:12) How marketing collaborates with product (45:55) Marketing lessons from working in an open core company (49:46) Examples of GitLab's focus on transparency (52:22) Why GitLab is transparent about their marketing (54:59) 2 examples of GitLab's uniquely transparent culture (58:35) The downsides of being a transparent company (60:13) GitLab's meeting structure and cadence (62:04) Benefits of having an engineering and product background as CMO (71:09) People who made an outsized impact on Ashley's career Thu, 26 Oct 2023 08:00:00 -0000 The business of growing and monetizing an open source product | Ashley Kramer (GitLab CMO/CSO) full First Round Ashley Kramer is the CMO and CSO at GitLab, a publicly listed DevSecOps platform. Ashley took a unique path into her CMO role. She started out in software engineering before becoming a product leader, and eventually, a marketer. Most recently, Ashley was the CPO and CMO at Sisense, a data analytics company last valued at over $1b. Ashley Kramer is the CMO and CSO at GitLab, a publicly listed DevSecOps platform. Ashley took a unique path into her CMO role. She started out in software engineering before becoming a product leader, and eventually, a marketer. Most recently, Ashley was the CPO and CMO at Sisense, a data analytics company last valued at over $1b. — In today’s episode we discuss: How GitLab layered a commercial model on top of open source roots GitLab’s main marketing metrics Examples, benefits, and downsides of a transparent company culture How GitLab serves enterprise customers, and a passionate developer community Unique marketing lessons from working in an open core company An example of a recent marketing campaign — Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ — Where to find Ashley Kramer: Twitter/x: https://twitter.com/ashleyekramer LinkedIn: https://www.linkedin.com/in/ashleyekramer/ — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Referenced: CISO: https://www.cisco.com/c/en/us/products/security/what-is-ciso.html DevSecOps: https://about.gitlab.com/topics/devsecops/ E-Group: https://about.gitlab.com/company/team/e-group/ GitLab: https://gitlab.com GitLab legal team’s SAFE framework: https://about.gitlab.com/handbook/legal/safe-framework/ GitLab’s open core business model: https://handbook.gitlab.com/handbook/company/stewardship/ GitLab’s open source employee handbook: https://handbook.gitlab.com/handbook/people-group/ GitLab’s open source marketing handbook: https://about.gitlab.com/handbook/marketing/ GitLab’s open source remote handbook: https://handbook.gitlab.com/handbook/company/culture/all-remote/guide/ Sid Sijbrandij, CEO of GitLab: https://www.linkedin.com/in/sijbrandij/ Tableau: https://www.tableau.com/ — Timestamps: (00:00) Intro (02:34) Marketing in closed vs open source companies (07:40) The role of marketing at GitLab (09:23) The tensions of being a commercial, open source company (12:36) Advice for nurturing community and dealing with disagreements (15:02) GitLab's main marketing metrics (20:26) The thinking behind GitLab’s org structure, in and around marketing (28:19) Selling to enterprise as an open core company (29:53) The difference between open core and open source (30:39) Serving many different customer segments (35:10) GitLab's planning process (39:22) An example of GitLab’s marketing in practice (42:12) How marketing collaborates with product (45:55) Marketing lessons from working in an open core company (49:46) Examples of GitLab's focus on transparency (52:22) Why GitLab is transparent about their marketing (54:59) 2 examples of GitLab's uniquely transparent culture (58:35) The downsides of being a transparent company (60:13) GitLab's meeting structure and cadence (62:04) Benefits of having an engineering and product background as CMO (71:09) People who made an outsized impact on Ashley's career Ashley Kramer is the CMO and CSO at GitLab, a publicly listed DevSecOps platform. Ashley took a unique path into her CMO role. She started out in software engineering before becoming a product leader, and eventually, a marketer. Most recently, Ashley was the CPO and CMO at Sisense, a data analytics company last valued at over $1b.

—

In today’s episode we discuss:

  • How GitLab layered a commercial model on top of open source roots
  • GitLab’s main marketing metrics
  • Examples, benefits, and downsides of a transparent company culture
  • How GitLab serves enterprise customers, and a passionate developer community
  • Unique marketing lessons from working in an open core company
  • An example of a recent marketing campaign

—

Where to find Brett Berson:

  • Twitter: https://twitter.com/brettberson
  • LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/

—

Where to find Ashley Kramer:

  • Twitter/x: https://twitter.com/ashleyekramer
  • LinkedIn: https://www.linkedin.com/in/ashleyekramer/

—

Where to find First Round Capital:

  • Website: https://firstround.com/
  • First Round Review: https://review.firstround.com/
  • Twitter: https://twitter.com/firstround
  • Youtube: https://www.youtube.com/@FirstRoundCapital
  • This podcast on all platforms: https://review.firstround.com/podcast

—

Referenced:

  • CISO: https://www.cisco.com/c/en/us/products/security/what-is-ciso.html
  • DevSecOps: https://about.gitlab.com/topics/devsecops/
  • E-Group: https://about.gitlab.com/company/team/e-group/
  • GitLab: https://gitlab.com
  • GitLab legal team’s SAFE framework: https://about.gitlab.com/handbook/legal/safe-framework/
  • GitLab’s open core business model: https://handbook.gitlab.com/handbook/company/stewardship/
  • GitLab’s open source employee handbook: https://handbook.gitlab.com/handbook/people-group/
  • GitLab’s open source marketing handbook: https://about.gitlab.com/handbook/marketing/
  • GitLab’s open source remote handbook: https://handbook.gitlab.com/handbook/company/culture/all-remote/guide/
  • Sid Sijbrandij, CEO of GitLab: https://www.linkedin.com/in/sijbrandij/
  • Tableau: https://www.tableau.com/

—

Timestamps:

(00:00) Intro

(02:34) Marketing in closed vs open source companies

(07:40) The role of marketing at GitLab

(09:23) The tensions of being a commercial, open source company

(12:36) Advice for nurturing community and dealing with disagreements

(15:02) GitLab's main marketing metrics

(20:26) The thinking behind GitLab’s org structure, in and around marketing

(28:19) Selling to enterprise as an open core company

(29:53) The difference between open core and open source

(30:39) Serving many different customer segments

(35:10) GitLab's planning process

(39:22) An example of GitLab’s marketing in practice

(42:12) How marketing collaborates with product

(45:55) Marketing lessons from working in an open core company

(49:46) Examples of GitLab's focus on transparency

(52:22) Why GitLab is transparent about their marketing

(54:59) 2 examples of GitLab's uniquely transparent culture

(58:35) The downsides of being a transparent company

(60:13) GitLab's meeting structure and cadence

(62:04) Benefits of having an engineering and product background as CMO

(71:09) People who made an outsized impact on Ashley's career

]]> 4447 How to leverage intuition, customer support, and raw effort | Colin Zima (Omni & Looker) Colin Zima is the co-founder and CEO of Omni, a business intelligence tool that has raised over $26.9m. Prior to starting Omni, Colin was Chief Analytics Officer and VP of Product at Looker, which was acquired by Google for $2.6b. Colin was an early employee at Looker, and stood up its high-touch customer support arm, which turned into a cornerstone competitive advantage for the company. — In today’s episode we discuss: Lessons from Looker When, why and how to invest in white-glove customer support Tactics for scaling high-touch customer support Colin’s intuition-based approach to product How Looker hit their goals for 24 quarters in a row The founding story of Omni Colin’s hot takes on picking startups, hiring PMs, and more — Referenced: BigQuery: https://cloud.google.com/bigquery Hotel Tonight: https://www.hoteltonight.com/ Omni: https://omni.co/ Tableau: https://www.tableau.com/ — Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ — Where to find Colin Zima: Twitter: https://twitter.com/drinkzima?lang=en LinkedIn: https://www.linkedin.com/in/colinzima/ — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:30) Colin's unique entry into Looker (04:35) How Colin talks to users (08:20) How Colin's scope at Looker expanded (10:53) Why and how to provide white-glove customer support (20:25) Which companies should invest heavily in customer support? (22:49) Hiring for and hiring from customer support (27:40) The #1 thing for making customer support effective at scale (29:32) The culture of customer support at Omni (32:57) Insights on product strategy (41:33) The role of intuition vs data in product decisions (44:25) The merits and downsides of an intuition-driven approach to product (48:36) Insights from hitting every goal for 24 quarters straight (55:07) The founding story of Omni (58:10) How Colin maintains intellectual honesty as a founder (60:02) How Colin thinks about what to copy vs not copy from Looker (63:25) How to pick which startup to join (66:07) The most underrated trait in early stage startup employees (68:11) Colin's take on founder-market-fit (69:42] Unpopular opinion on how to hire good PMs (72:28) The people who made an outsized impact on Colin's career Thu, 12 Oct 2023 08:00:00 -0000 How to leverage intuition, customer support, and raw effort | Colin Zima (Omni & Looker) full First Round Colin Zima is the co-founder and CEO of Omni, a business intelligence tool that has raised over $26.9m. Prior to starting Omni, Colin was Chief Analytics Officer and VP of Product at Looker, which was acquired by Google for $2.6b. Colin was an early employee at Looker, and stood up its high-touch customer support arm, which turned into a cornerstone competitive advantage for the company. Colin Zima is the co-founder and CEO of Omni, a business intelligence tool that has raised over $26.9m. Prior to starting Omni, Colin was Chief Analytics Officer and VP of Product at Looker, which was acquired by Google for $2.6b. Colin was an early employee at Looker, and stood up its high-touch customer support arm, which turned into a cornerstone competitive advantage for the company. — In today’s episode we discuss: Lessons from Looker When, why and how to invest in white-glove customer support Tactics for scaling high-touch customer support Colin’s intuition-based approach to product How Looker hit their goals for 24 quarters in a row The founding story of Omni Colin’s hot takes on picking startups, hiring PMs, and more — Referenced: BigQuery: https://cloud.google.com/bigquery Hotel Tonight: https://www.hoteltonight.com/ Omni: https://omni.co/ Tableau: https://www.tableau.com/ — Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ — Where to find Colin Zima: Twitter: https://twitter.com/drinkzima?lang=en LinkedIn: https://www.linkedin.com/in/colinzima/ — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:30) Colin's unique entry into Looker (04:35) How Colin talks to users (08:20) How Colin's scope at Looker expanded (10:53) Why and how to provide white-glove customer support (20:25) Which companies should invest heavily in customer support? (22:49) Hiring for and hiring from customer support (27:40) The #1 thing for making customer support effective at scale (29:32) The culture of customer support at Omni (32:57) Insights on product strategy (41:33) The role of intuition vs data in product decisions (44:25) The merits and downsides of an intuition-driven approach to product (48:36) Insights from hitting every goal for 24 quarters straight (55:07) The founding story of Omni (58:10) How Colin maintains intellectual honesty as a founder (60:02) How Colin thinks about what to copy vs not copy from Looker (63:25) How to pick which startup to join (66:07) The most underrated trait in early stage startup employees (68:11) Colin's take on founder-market-fit (69:42] Unpopular opinion on how to hire good PMs (72:28) The people who made an outsized impact on Colin's career Colin Zima is the co-founder and CEO of Omni, a business intelligence tool that has raised over $26.9m. Prior to starting Omni, Colin was Chief Analytics Officer and VP of Product at Looker, which was acquired by Google for $2.6b. Colin was an early employee at Looker, and stood up its high-touch customer support arm, which turned into a cornerstone competitive advantage for the company.

—

In today’s episode we discuss:

  • Lessons from Looker
  • When, why and how to invest in white-glove customer support
  • Tactics for scaling high-touch customer support
  • Colin’s intuition-based approach to product
  • How Looker hit their goals for 24 quarters in a row
  • The founding story of Omni
  • Colin’s hot takes on picking startups, hiring PMs, and more

—

Referenced:

—

Where to find Brett Berson:

—

Where to find Colin Zima:

—

Where to find First Round Capital:

—

Timestamps:

(00:00) Introduction

(02:30) Colin's unique entry into Looker

(04:35) How Colin talks to users

(08:20) How Colin's scope at Looker expanded

(10:53) Why and how to provide white-glove customer support

(20:25) Which companies should invest heavily in customer support?

(22:49) Hiring for and hiring from customer support

(27:40) The #1 thing for making customer support effective at scale

(29:32) The culture of customer support at Omni

(32:57) Insights on product strategy

(41:33) The role of intuition vs data in product decisions

(44:25) The merits and downsides of an intuition-driven approach to product

(48:36) Insights from hitting every goal for 24 quarters straight

(55:07) The founding story of Omni

(58:10) How Colin maintains intellectual honesty as a founder

(60:02) How Colin thinks about what to copy vs not copy from Looker

(63:25) How to pick which startup to join

(66:07) The most underrated trait in early stage startup employees

(68:11) Colin's take on founder-market-fit

(69:42] Unpopular opinion on how to hire good PMs

(72:28) The people who made an outsized impact on Colin's career

]]> 4458 Building Zapier from first principles | Contrarian takes on growth, hiring, fundraising | Wade Foster (Co-founder & CEO) Wade Foster is the Co-founder & CEO at Zapier, a platform for building workflow automations without a developer. Zapier was started during 2011 in Columbia, Missouri, and by 2021, it was valued at $5b, having only raised $1.3m. Prior to founding Zapier, Wade had just two professional jobs, and had never managed or hired anyone. He worked as a PM on a web app used by 20k students, and as an Email Marketing Manager at Veterans United - a role that had a significant influence on Zapier’s eventual success. In today’s episode, we discuss: The stories and thinking behind Zapier’s most unorthodox decisions How Wade thinks about product market fit How Zapier built their powerful distribution engine The fascinating story of Veterans United, and its impact on Zapier How Wade thinks about fundraising Why Wade lives by “don’t hire ‘til it hurts” Key lessons on people management Referenced: Basecamp: https://basecamp.com/ Bingo Card Creator: https://www.bingocardcreator.com Bryan Helmig, Co-founder of Zapier: https://www.linkedin.com/in/bryanhelmig John Wooden quote: https://www.thewoodeneffect.com/be-quick-but-dont-hurry/ Mailchimp: https://mailchimp.com/ Mike Knoop, Co-founder of Zapier: https://www.linkedin.com/in/mikeknoop Patrick Mckenzie, creator of Bingo Card Creator: https://www.linkedin.com/in/patrickmckenzie/ PayPal: https://www.paypal.com/ Salesforce: https://www.salesforce.com/ SMBs: https://www.techtarget.com/whatis/definition/SMB-small-and-medium-sized-business-or-small-and-midsized-business Stripe: https://stripe.com/ Thinking in Bets by Annie Duke: https://www.amazon.com.au/Thinking-Bets-Annie-Duke/dp/0735216355 Tony Xu, CEO of DoorDash: https://www.linkedin.com/in/xutony/ Twilio: https://www.twilio.com/ Veterans United Home Loans: https://www.veteransunited.com/ Zapier: https://zapier.com/ Where to find Brett Berson Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Where to find Wade Foster Twitter: https://twitter.com/wadefoster LinkedIn: https://www.linkedin.com/in/wadefoster Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps (05:46) The fascinating story of Veterans United (06:55) Lessons from Veterans United (08:35) The most important things Zapier got right (10:13) How Zapier built their powerful distribution engine (16:56) Why Zapier didn't move to focusing on enterprise (19:06) How Wade thinks about product market fit (24:26) The role of skill vs luck in Zapier's success (26:23) What was hard about building Zapier (30:03) Key lessons on people management (32:35) Rule of thumb: "don't hire ‘til it hurts” (36:42) Zapier's #1 hiring mistake (42:50) How to test for scrappiness in the hiring process (44:31) Do hiring playbooks transfer between companies? (50:01) The 12 year evolution of Zapier's product (53:20) How Zapier makes product decisions (55:40) How Zapier thought about competition (60:11) How to foster intellectual honesty in yourself and your org (65:35) The people who most impacted Wade's worldviews Thu, 05 Oct 2023 08:00:00 -0000 Building Zapier from first principles | Contrarian takes on growth, hiring, fundraising | Wade Foster (Co-founder & CEO) full First Round Wade Foster is the Co-founder & CEO at Zapier, a platform for building workflow automations without a developer. Zapier was started during 2011 in Columbia, Missouri, and by 2021, it was valued at $5b, having only raised $1.3m. Prior to founding Zapier, Wade had just two professional jobs, and had never managed or hired anyone. He worked as a PM on a web app used by 20k students, and as an Email Marketing Manager at Veterans United - a role that had a significant influence on Zapier’s eventual success. Wade Foster is the Co-founder & CEO at Zapier, a platform for building workflow automations without a developer. Zapier was started during 2011 in Columbia, Missouri, and by 2021, it was valued at $5b, having only raised $1.3m. Prior to founding Zapier, Wade had just two professional jobs, and had never managed or hired anyone. He worked as a PM on a web app used by 20k students, and as an Email Marketing Manager at Veterans United - a role that had a significant influence on Zapier’s eventual success. In today’s episode, we discuss: The stories and thinking behind Zapier’s most unorthodox decisions How Wade thinks about product market fit How Zapier built their powerful distribution engine The fascinating story of Veterans United, and its impact on Zapier How Wade thinks about fundraising Why Wade lives by “don’t hire ‘til it hurts” Key lessons on people management Referenced: Basecamp: https://basecamp.com/ Bingo Card Creator: https://www.bingocardcreator.com Bryan Helmig, Co-founder of Zapier: https://www.linkedin.com/in/bryanhelmig John Wooden quote: https://www.thewoodeneffect.com/be-quick-but-dont-hurry/ Mailchimp: https://mailchimp.com/ Mike Knoop, Co-founder of Zapier: https://www.linkedin.com/in/mikeknoop Patrick Mckenzie, creator of Bingo Card Creator: https://www.linkedin.com/in/patrickmckenzie/ PayPal: https://www.paypal.com/ Salesforce: https://www.salesforce.com/ SMBs: https://www.techtarget.com/whatis/definition/SMB-small-and-medium-sized-business-or-small-and-midsized-business Stripe: https://stripe.com/ Thinking in Bets by Annie Duke: https://www.amazon.com.au/Thinking-Bets-Annie-Duke/dp/0735216355 Tony Xu, CEO of DoorDash: https://www.linkedin.com/in/xutony/ Twilio: https://www.twilio.com/ Veterans United Home Loans: https://www.veteransunited.com/ Zapier: https://zapier.com/ Where to find Brett Berson Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Where to find Wade Foster Twitter: https://twitter.com/wadefoster LinkedIn: https://www.linkedin.com/in/wadefoster Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps (05:46) The fascinating story of Veterans United (06:55) Lessons from Veterans United (08:35) The most important things Zapier got right (10:13) How Zapier built their powerful distribution engine (16:56) Why Zapier didn't move to focusing on enterprise (19:06) How Wade thinks about product market fit (24:26) The role of skill vs luck in Zapier's success (26:23) What was hard about building Zapier (30:03) Key lessons on people management (32:35) Rule of thumb: "don't hire ‘til it hurts” (36:42) Zapier's #1 hiring mistake (42:50) How to test for scrappiness in the hiring process (44:31) Do hiring playbooks transfer between companies? (50:01) The 12 year evolution of Zapier's product (53:20) How Zapier makes product decisions (55:40) How Zapier thought about competition (60:11) How to foster intellectual honesty in yourself and your org (65:35) The people who most impacted Wade's worldviews Wade Foster is the Co-founder & CEO at Zapier, a platform for building workflow automations without a developer. Zapier was started during 2011 in Columbia, Missouri, and by 2021, it was valued at $5b, having only raised $1.3m. Prior to founding Zapier, Wade had just two professional jobs, and had never managed or hired anyone. He worked as a PM on a web app used by 20k students, and as an Email Marketing Manager at Veterans United - a role that had a significant influence on Zapier’s eventual success.


In today’s episode, we discuss:

  • The stories and thinking behind Zapier’s most unorthodox decisions
  • How Wade thinks about product market fit
  • How Zapier built their powerful distribution engine
  • The fascinating story of Veterans United, and its impact on Zapier
  • How Wade thinks about fundraising
  • Why Wade lives by “don’t hire ‘til it hurts”
  • Key lessons on people management


Referenced:


Where to find Brett Berson


Where to find Wade Foster


Where to find First Round Capital:


Timestamps

(05:46) The fascinating story of Veterans United

(06:55) Lessons from Veterans United

(08:35) The most important things Zapier got right

(10:13) How Zapier built their powerful distribution engine

(16:56) Why Zapier didn't move to focusing on enterprise

(19:06) How Wade thinks about product market fit

(24:26) The role of skill vs luck in Zapier's success

(26:23) What was hard about building Zapier

(30:03) Key lessons on people management

(32:35) Rule of thumb: "don't hire ‘til it hurts”

(36:42) Zapier's #1 hiring mistake

(42:50) How to test for scrappiness in the hiring process

(44:31) Do hiring playbooks transfer between companies?

(50:01) The 12 year evolution of Zapier's product

(53:20) How Zapier makes product decisions

(55:40) How Zapier thought about competition

(60:11) How to foster intellectual honesty in yourself and your org

(65:35) The people who most impacted Wade's worldviews

]]> 4037 How young outsiders changed the shipping industry by finding product-market fit again and again | Laura Behrens Wu (Shippo) Laura Behrens Wu is the Founder & CEO at Shippo, a company that has raised $100m+ and was last valued at $1b in 2021. Shippo provides an API and dashboard that makes shipping easy for e-commerce businesses, marketplaces, and platforms. Prior to starting Shippo, Laura graduated from Harvard University, and was heavily influenced by a short internship at LendUp, which exposed her to Silicon Valley and startup culture.  In today’s episode we discuss: Shippo’s pivot-stricken origin story Finding product-market-fit, again and again and again Laura’s unique take on founder-market-fit Advice on talking to users The 3 Horizons Framework for prioritizing resources across a core business and longer-term bets The email Laura sends every Sunday because of Frank Slootman’s advice Referenced: Amp It Up by Frank Slootman: https://www.amazon.com/Amp-Unlocking-Hypergrowth-Expectations-Intensity/dp/1119836115 Expedia: https://www.expedia.com/ FedEx: https://www.fedex.com/ Frank Slootman: https://www.linkedin.com/in/frankslootman/ Jerry Colonna: https://www.linkedin.com/in/jerry-colonna-reboot/ Josh Koppelman: https://www.linkedin.com/in/jkoppelman/ Khalid Halim: https://review.firstround.com/the-science-of-speaking-is-the-art-of-being-heard LendUp: https://www.lendup.com/ Shippo: https://goshippo.com/ Shopify: https://www.shopify.com/ SMBs: https://www.fool.com/the-ascent/small-business/articles/smb-business/ Stripe: https://stripe.com/ UPS: https://www.ups.com/us/en/global.page 70/20/10 rule from Google: https://www.itonics-innovation.com/blog/702010-rule-of-innovation Where to find Todd Jackson: Twitter: https://twitter.com/tjack LinkedIn: https://www.linkedin.com/in/toddj0 Where to find Laura Behrens Wu: Twitter: https://twitter.com/LauraBehrensWu LinkedIn https://www.linkedin.com/in/laurabehrenswu Personal website: https://laurabehrenswu.com/ Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps (02:36) The Shippo origin story (06:57) Why they pivoted into Shippo (11:01) How they got their first customers (13:27) The role of timing in Shippo's early success (14:40) The value of being an outsider (17:49) When founder-market-fit is and isn't necessary (19:07) The path to product-market-fit (22:06) What kept the Shippo team persisting (24:41) Advice on talking to users (29:28) Shippo's fundraising journey (34:26) Finding product-market-fit again and again (37:54) The 3 Horizons Framework (45:04) Shippo's culture and early team (49:17) Hiring people you can learn from (50:40) Laura's most impactful hires (52:12) Frank Slootman's "Sunday Email” (55:43) Laura's #1 piece of advice for founders (57:34) The most memorable influences on Laura's career Thu, 28 Sep 2023 08:00:00 -0000 How young outsiders changed the shipping industry by finding product-market fit again and again | Laura Behrens Wu (Shippo) full First Round Laura Behrens Wu is the Founder & CEO at Shippo, a company that has raised $100m+ and was last valued at $1b in 2021. Shippo provides an API and dashboard that makes shipping easy for e-commerce businesses, marketplaces, and platforms. Prior to starting Shippo, Laura graduated from Harvard University, and was heavily influenced by a short internship at LendUp, which exposed her to Silicon Valley and startup culture. Laura Behrens Wu is the Founder & CEO at Shippo, a company that has raised $100m+ and was last valued at $1b in 2021. Shippo provides an API and dashboard that makes shipping easy for e-commerce businesses, marketplaces, and platforms. Prior to starting Shippo, Laura graduated from Harvard University, and was heavily influenced by a short internship at LendUp, which exposed her to Silicon Valley and startup culture.  In today’s episode we discuss: Shippo’s pivot-stricken origin story Finding product-market-fit, again and again and again Laura’s unique take on founder-market-fit Advice on talking to users The 3 Horizons Framework for prioritizing resources across a core business and longer-term bets The email Laura sends every Sunday because of Frank Slootman’s advice Referenced: Amp It Up by Frank Slootman: https://www.amazon.com/Amp-Unlocking-Hypergrowth-Expectations-Intensity/dp/1119836115 Expedia: https://www.expedia.com/ FedEx: https://www.fedex.com/ Frank Slootman: https://www.linkedin.com/in/frankslootman/ Jerry Colonna: https://www.linkedin.com/in/jerry-colonna-reboot/ Josh Koppelman: https://www.linkedin.com/in/jkoppelman/ Khalid Halim: https://review.firstround.com/the-science-of-speaking-is-the-art-of-being-heard LendUp: https://www.lendup.com/ Shippo: https://goshippo.com/ Shopify: https://www.shopify.com/ SMBs: https://www.fool.com/the-ascent/small-business/articles/smb-business/ Stripe: https://stripe.com/ UPS: https://www.ups.com/us/en/global.page 70/20/10 rule from Google: https://www.itonics-innovation.com/blog/702010-rule-of-innovation Where to find Todd Jackson: Twitter: https://twitter.com/tjack LinkedIn: https://www.linkedin.com/in/toddj0 Where to find Laura Behrens Wu: Twitter: https://twitter.com/LauraBehrensWu LinkedIn https://www.linkedin.com/in/laurabehrenswu Personal website: https://laurabehrenswu.com/ Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps (02:36) The Shippo origin story (06:57) Why they pivoted into Shippo (11:01) How they got their first customers (13:27) The role of timing in Shippo's early success (14:40) The value of being an outsider (17:49) When founder-market-fit is and isn't necessary (19:07) The path to product-market-fit (22:06) What kept the Shippo team persisting (24:41) Advice on talking to users (29:28) Shippo's fundraising journey (34:26) Finding product-market-fit again and again (37:54) The 3 Horizons Framework (45:04) Shippo's culture and early team (49:17) Hiring people you can learn from (50:40) Laura's most impactful hires (52:12) Frank Slootman's "Sunday Email” (55:43) Laura's #1 piece of advice for founders (57:34) The most memorable influences on Laura's career Laura Behrens Wu is the Founder & CEO at Shippo, a company that has raised $100m+ and was last valued at $1b in 2021. Shippo provides an API and dashboard that makes shipping easy for e-commerce businesses, marketplaces, and platforms. Prior to starting Shippo, Laura graduated from Harvard University, and was heavily influenced by a short internship at LendUp, which exposed her to Silicon Valley and startup culture. 


In today’s episode we discuss:

  • Shippo’s pivot-stricken origin story
  • Finding product-market-fit, again and again and again
  • Laura’s unique take on founder-market-fit
  • Advice on talking to users
  • The 3 Horizons Framework for prioritizing resources across a core business and longer-term bets
  • The email Laura sends every Sunday because of Frank Slootman’s advice


Referenced:


Where to find Todd Jackson:


Where to find Laura Behrens Wu:


Where to find First Round Capital:


Timestamps

(02:36) The Shippo origin story

(06:57) Why they pivoted into Shippo

(11:01) How they got their first customers

(13:27) The role of timing in Shippo's early success

(14:40) The value of being an outsider

(17:49) When founder-market-fit is and isn't necessary

(19:07) The path to product-market-fit

(22:06) What kept the Shippo team persisting

(24:41) Advice on talking to users

(29:28) Shippo's fundraising journey

(34:26) Finding product-market-fit again and again

(37:54) The 3 Horizons Framework

(45:04) Shippo's culture and early team

(49:17) Hiring people you can learn from

(50:40) Laura's most impactful hires

(52:12) Frank Slootman's "Sunday Email”

(55:43) Laura's #1 piece of advice for founders

(57:34) The most memorable influences on Laura's career

]]> 3631 AI Hot Takes and Unusual Twitter Fundraising Strategies with Dan Siroker (Rewind AI) Dan Siroker is the co-founder and CEO at Rewind AI, a personalized AI powered by everything you’ve seen, said, or heard. Dan launched Rewind to an emphatic response on Twitter, and used a public pitch video to fundraise at a $350m valuation. Prior to starting Rewind, Dan co-founded Optimizely, which reached $120m ARR before being acquired by Episerver, a content management company. Dan was also the Director of Analytics for Obama’s first presidential campaign. In today’s episode, we discuss: Rewind’s journey to Product Market Fit Lessons from Optimizely and being a second time founder Dan’s one-of-a-kind Twitter fundraising strategy Dan’s hot takes on the future of AI Where to build in AI, and what makes a “wrapper” thin versus thick Referenced: Apple’s Silicon: https://www.macrumors.com/guide/apple-silicon/ ChatGPT: https://chat.openai.com/ Dan publicly sharing his own 360 performance reviews: https://twitter.com/dsiroker/status/1689763756459675650 Dan’s public Twitter fundraise: https://twitter.com/dsiroker/status/1646895452317700097 Dan’s Rewind demo tweet: https://twitter.com/dsiroker/status/1638799931891920897 Google Glass: https://en.wikipedia.org/wiki/Google_Glass Google Wave: https://en.wikipedia.org/wiki/Google_Wave Maslow's Hierarchy of Needs: https://www.simplypsychology.org/maslow.html Optimizely: https://www.optimizely.com/ Paul Graham: https://twitter.com/paulg Rahul Vohra’s framework for measuring and optimizing Product Market Fit: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit Rewind AI: https://www.rewind.ai/ Scribe (which morphed into Rewind): https://www.scribe.ai/about The Mom Test book: https://www.momtestbook.com/ Where to find Dan Siroker: Twitter: https://twitter.com/dsiroker LinkedIn: https://www.linkedin.com/in/dsiroker Personal website: https://siroker.com/ Blog: https://medium.com/@dsiroker Where to find Todd Jackson: Twitter: https://twitter.com/tjack LinkedIn: https://www.linkedin.com/in/toddj0 Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps (02:25) Rewind's origin story (04:04) How Rewind works (07:24) Managing scope when building Rewind (13:47) How Dan thought about early user feedback (17:08) Rewind's cultural mantra for shipping and validating fast (18:35) Product positioning as a category creator (20:39) Lessons from being a 2nd time founder (26:11) Cultural values at Optimizely and Rewind (28:22) How Dan defines and operationalizes Product Market Fit (32:06) Audience segmentation (34:32) Measuring Product Market Fit (36:23) Dan's take on the current AI hype (38:11) What makes a "wrapper" thin vs thick? (39:50) Where founders should and shouldn't build within the AI ecosystem (43:22) Trends in consumer expectations around data privacy (46:59) What AI might look like 10 years from now (51:09) Dan's one-of-a-kind public Twitter fundraise (59:40) What's next for Rewind? (61:26) The influence of Paul Graham (62:47) Dan's #1 piece of advice (64:23) Dan's #1 book recommendation Thu, 14 Sep 2023 08:00:00 -0000 AI Hot Takes and Unusual Twitter Fundraising Strategies with Dan Siroker (Rewind AI) full First Round Dan Siroker is the co-founder and CEO at Rewind AI, a personalized AI powered by everything you’ve seen, said, or heard. Dan launched Rewind to an emphatic response on Twitter, and used a public pitch video to fundraise at a $350m valuation. Prior to starting Rewind, Dan co-founded Optimizely, which reached $120m ARR before being acquired by Episerver, a content management company. Dan was also the Director of Analytics for Obama’s first presidential campaign. Dan Siroker is the co-founder and CEO at Rewind AI, a personalized AI powered by everything you’ve seen, said, or heard. Dan launched Rewind to an emphatic response on Twitter, and used a public pitch video to fundraise at a $350m valuation. Prior to starting Rewind, Dan co-founded Optimizely, which reached $120m ARR before being acquired by Episerver, a content management company. Dan was also the Director of Analytics for Obama’s first presidential campaign. In today’s episode, we discuss: Rewind’s journey to Product Market Fit Lessons from Optimizely and being a second time founder Dan’s one-of-a-kind Twitter fundraising strategy Dan’s hot takes on the future of AI Where to build in AI, and what makes a “wrapper” thin versus thick Referenced: Apple’s Silicon: https://www.macrumors.com/guide/apple-silicon/ ChatGPT: https://chat.openai.com/ Dan publicly sharing his own 360 performance reviews: https://twitter.com/dsiroker/status/1689763756459675650 Dan’s public Twitter fundraise: https://twitter.com/dsiroker/status/1646895452317700097 Dan’s Rewind demo tweet: https://twitter.com/dsiroker/status/1638799931891920897 Google Glass: https://en.wikipedia.org/wiki/Google_Glass Google Wave: https://en.wikipedia.org/wiki/Google_Wave Maslow's Hierarchy of Needs: https://www.simplypsychology.org/maslow.html Optimizely: https://www.optimizely.com/ Paul Graham: https://twitter.com/paulg Rahul Vohra’s framework for measuring and optimizing Product Market Fit: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit Rewind AI: https://www.rewind.ai/ Scribe (which morphed into Rewind): https://www.scribe.ai/about The Mom Test book: https://www.momtestbook.com/ Where to find Dan Siroker: Twitter: https://twitter.com/dsiroker LinkedIn: https://www.linkedin.com/in/dsiroker Personal website: https://siroker.com/ Blog: https://medium.com/@dsiroker Where to find Todd Jackson: Twitter: https://twitter.com/tjack LinkedIn: https://www.linkedin.com/in/toddj0 Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps (02:25) Rewind's origin story (04:04) How Rewind works (07:24) Managing scope when building Rewind (13:47) How Dan thought about early user feedback (17:08) Rewind's cultural mantra for shipping and validating fast (18:35) Product positioning as a category creator (20:39) Lessons from being a 2nd time founder (26:11) Cultural values at Optimizely and Rewind (28:22) How Dan defines and operationalizes Product Market Fit (32:06) Audience segmentation (34:32) Measuring Product Market Fit (36:23) Dan's take on the current AI hype (38:11) What makes a "wrapper" thin vs thick? (39:50) Where founders should and shouldn't build within the AI ecosystem (43:22) Trends in consumer expectations around data privacy (46:59) What AI might look like 10 years from now (51:09) Dan's one-of-a-kind public Twitter fundraise (59:40) What's next for Rewind? (61:26) The influence of Paul Graham (62:47) Dan's #1 piece of advice (64:23) Dan's #1 book recommendation Dan Siroker is the co-founder and CEO at Rewind AI, a personalized AI powered by everything you’ve seen, said, or heard. Dan launched Rewind to an emphatic response on Twitter, and used a public pitch video to fundraise at a $350m valuation. Prior to starting Rewind, Dan co-founded Optimizely, which reached $120m ARR before being acquired by Episerver, a content management company. Dan was also the Director of Analytics for Obama’s first presidential campaign.


In today’s episode, we discuss:

  • Rewind’s journey to Product Market Fit
  • Lessons from Optimizely and being a second time founder
  • Dan’s one-of-a-kind Twitter fundraising strategy
  • Dan’s hot takes on the future of AI
  • Where to build in AI, and what makes a “wrapper” thin versus thick


Referenced:

  • Apple’s Silicon: https://www.macrumors.com/guide/apple-silicon/
  • ChatGPT: https://chat.openai.com/
  • Dan publicly sharing his own 360 performance reviews: https://twitter.com/dsiroker/status/1689763756459675650
  • Dan’s public Twitter fundraise: https://twitter.com/dsiroker/status/1646895452317700097
  • Dan’s Rewind demo tweet: https://twitter.com/dsiroker/status/1638799931891920897
  • Google Glass: https://en.wikipedia.org/wiki/Google_Glass
  • Google Wave: https://en.wikipedia.org/wiki/Google_Wave
  • Maslow's Hierarchy of Needs: https://www.simplypsychology.org/maslow.html
  • Optimizely: https://www.optimizely.com/
  • Paul Graham: https://twitter.com/paulg
  • Rahul Vohra’s framework for measuring and optimizing Product Market Fit: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit
  • Rewind AI: https://www.rewind.ai/
  • Scribe (which morphed into Rewind): https://www.scribe.ai/about
  • The Mom Test book: https://www.momtestbook.com/


Where to find Dan Siroker:

  • Twitter: https://twitter.com/dsiroker
  • LinkedIn: https://www.linkedin.com/in/dsiroker
  • Personal website: https://siroker.com/
  • Blog: https://medium.com/@dsiroker


Where to find Todd Jackson:

  • Twitter: https://twitter.com/tjack
  • LinkedIn: https://www.linkedin.com/in/toddj0


Where to find First Round Capital:

  • Website: https://firstround.com/
  • First Round Review: https://review.firstround.com/
  • Twitter: https://twitter.com/firstround
  • Youtube: https://www.youtube.com/@FirstRoundCapital
  • This podcast on all platforms: https://review.firstround.com/podcast


Timestamps

(02:25) Rewind's origin story

(04:04) How Rewind works

(07:24) Managing scope when building Rewind

(13:47) How Dan thought about early user feedback

(17:08) Rewind's cultural mantra for shipping and validating fast

(18:35) Product positioning as a category creator

(20:39) Lessons from being a 2nd time founder

(26:11) Cultural values at Optimizely and Rewind

(28:22) How Dan defines and operationalizes Product Market Fit

(32:06) Audience segmentation

(34:32) Measuring Product Market Fit

(36:23) Dan's take on the current AI hype

(38:11) What makes a "wrapper" thin vs thick?

(39:50) Where founders should and shouldn't build within the AI ecosystem

(43:22) Trends in consumer expectations around data privacy

(46:59) What AI might look like 10 years from now

(51:09) Dan's one-of-a-kind public Twitter fundraise

(59:40) What's next for Rewind?

(61:26) The influence of Paul Graham

(62:47) Dan's #1 piece of advice

(64:23) Dan's #1 book recommendation

]]> 3973 A guide to building product in a post-LLM world | Ryan Glasgow and Kevin Mandich from Sprig Sprig is an AI-powered user insights platform that has raised over $88m. Today’s discussion features two key individuals in Sprig’s journey so far: Ryan Glasgow, Sprig’s CEO and founder; and Kevin Mandich, Sprig’s Head of Machine Learning. Before Sprig, Ryan was an early PM at GraphScience, Vurb, and Weeby (all of which were acquired), and Kevin was an ML Engineer at Incubit, and a Post-Doctoral Researcher at UC San Diego. In today’s episode, we discuss: Key lessons from the Sprig founding story Product development in the pre vs. post-LLM world How to overcome AI skepticism How to evaluate new models and how to know when to switch Why you need an ML engineer Sprig’s “AI Squad” team structure How Sprig upskills all team members on AI Referenced: Auto-GPT: https://github.com/Significant-Gravitas/Auto-GPT Chat GPT: https://chat.openai.com Google’s BERT model: https://en.wikipedia.org/wiki/BERT_(language_model) Jira: https://www.atlassian.com/software/jira Jobs to Be Done Framework: https://hbr.org/2016/09/know-your-customers-jobs-to-be-done Langchain: https://www.langchain.com/ Sprig: https://sprig.com/ Where to find Ryan Glasgow: Twitter: https://twitter.com/ryanglasgow LinkedIn: https://www.linkedin.com/in/ryanglasgow/ Where to find Kevin Mandich: Twitter: https://twitter.com/kevinmandich LinkedIn: https://www.linkedin.com/in/kevinmandich/ Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps (02:50) Intro (04:57) What attracted Kevin to Sprig (05:53) Kevin's background before Sprig (07:56) How Ryan gained conviction about Kevin (09:55) Key technical challenges and how they solved them (18:46) How to overcome AI skepticism (21:47) The early difficulties of building an ML-enabled product (25:06) Evaluating new models and knowing when to switch (35:09) Using Chat GPT (37:23) Product development in the pre vs. post-LLM world (39:53) The impact of AI hype on Sprig's product development (45:36) Balancing AI automation with user-psychology (48:47) Do recent LLMs reduce Sprig's competitive advantage? (51:00) The importance of "selling the vision" to customers (54:40) How Sprig structures teams (57:25) How Sprig upskills all team members on AI (60:25) 3 key tips for companies trying to navigate AI (66:05) Major limitations with LLMs right now (70:27) The future of AI and the future of Sprig Thu, 07 Sep 2023 08:00:00 -0000 A guide to building product in a post-LLM world | Ryan Glasgow and Kevin Mandich from Sprig full First Round Sprig is an AI-powered user insights platform that has raised over $88m. Today’s discussion features two key individuals in Sprig’s journey so far: Ryan Glasgow, Sprig’s CEO and founder; and Kevin Mandich, Sprig’s Head of Machine Learning. Before Sprig, Ryan was an early PM at GraphScience, Vurb, and Weeby (all of which were acquired), and Kevin was an ML Engineer at Incubit, and a Post-Doctoral Researcher at UC San Diego. Sprig is an AI-powered user insights platform that has raised over $88m. Today’s discussion features two key individuals in Sprig’s journey so far: Ryan Glasgow, Sprig’s CEO and founder; and Kevin Mandich, Sprig’s Head of Machine Learning. Before Sprig, Ryan was an early PM at GraphScience, Vurb, and Weeby (all of which were acquired), and Kevin was an ML Engineer at Incubit, and a Post-Doctoral Researcher at UC San Diego. In today’s episode, we discuss: Key lessons from the Sprig founding story Product development in the pre vs. post-LLM world How to overcome AI skepticism How to evaluate new models and how to know when to switch Why you need an ML engineer Sprig’s “AI Squad” team structure How Sprig upskills all team members on AI Referenced: Auto-GPT: https://github.com/Significant-Gravitas/Auto-GPT Chat GPT: https://chat.openai.com Google’s BERT model: https://en.wikipedia.org/wiki/BERT_(language_model) Jira: https://www.atlassian.com/software/jira Jobs to Be Done Framework: https://hbr.org/2016/09/know-your-customers-jobs-to-be-done Langchain: https://www.langchain.com/ Sprig: https://sprig.com/ Where to find Ryan Glasgow: Twitter: https://twitter.com/ryanglasgow LinkedIn: https://www.linkedin.com/in/ryanglasgow/ Where to find Kevin Mandich: Twitter: https://twitter.com/kevinmandich LinkedIn: https://www.linkedin.com/in/kevinmandich/ Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps (02:50) Intro (04:57) What attracted Kevin to Sprig (05:53) Kevin's background before Sprig (07:56) How Ryan gained conviction about Kevin (09:55) Key technical challenges and how they solved them (18:46) How to overcome AI skepticism (21:47) The early difficulties of building an ML-enabled product (25:06) Evaluating new models and knowing when to switch (35:09) Using Chat GPT (37:23) Product development in the pre vs. post-LLM world (39:53) The impact of AI hype on Sprig's product development (45:36) Balancing AI automation with user-psychology (48:47) Do recent LLMs reduce Sprig's competitive advantage? (51:00) The importance of "selling the vision" to customers (54:40) How Sprig structures teams (57:25) How Sprig upskills all team members on AI (60:25) 3 key tips for companies trying to navigate AI (66:05) Major limitations with LLMs right now (70:27) The future of AI and the future of Sprig Sprig is an AI-powered user insights platform that has raised over $88m. Today’s discussion features two key individuals in Sprig’s journey so far: Ryan Glasgow, Sprig’s CEO and founder; and Kevin Mandich, Sprig’s Head of Machine Learning. Before Sprig, Ryan was an early PM at GraphScience, Vurb, and Weeby (all of which were acquired), and Kevin was an ML Engineer at Incubit, and a Post-Doctoral Researcher at UC San Diego.


In today’s episode, we discuss:

  • Key lessons from the Sprig founding story
  • Product development in the pre vs. post-LLM world
  • How to overcome AI skepticism
  • How to evaluate new models and how to know when to switch
  • Why you need an ML engineer
  • Sprig’s “AI Squad” team structure
  • How Sprig upskills all team members on AI


Referenced:

  • Auto-GPT: https://github.com/Significant-Gravitas/Auto-GPT
  • Chat GPT: https://chat.openai.com
  • Google’s BERT model: https://en.wikipedia.org/wiki/BERT_(language_model)
  • Jira: https://www.atlassian.com/software/jira
  • Jobs to Be Done Framework: https://hbr.org/2016/09/know-your-customers-jobs-to-be-done
  • Langchain: https://www.langchain.com/
  • Sprig: https://sprig.com/


Where to find Ryan Glasgow:

  • Twitter: https://twitter.com/ryanglasgow
  • LinkedIn: https://www.linkedin.com/in/ryanglasgow/


Where to find Kevin Mandich:

  • Twitter: https://twitter.com/kevinmandich
  • LinkedIn: https://www.linkedin.com/in/kevinmandich/


Where to find Brett Berson:

  • Twitter: https://twitter.com/brettberson
  • LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/


Where to find First Round Capital:

  • Website: https://firstround.com/
  • First Round Review: https://review.firstround.com/
  • Twitter: https://twitter.com/firstround
  • Youtube: https://www.youtube.com/@FirstRoundCapital
  • This podcast on all platforms: https://review.firstround.com/podcast


Timestamps

(02:50) Intro

(04:57) What attracted Kevin to Sprig

(05:53) Kevin's background before Sprig

(07:56) How Ryan gained conviction about Kevin

(09:55) Key technical challenges and how they solved them

(18:46) How to overcome AI skepticism

(21:47) The early difficulties of building an ML-enabled product

(25:06) Evaluating new models and knowing when to switch

(35:09) Using Chat GPT

(37:23) Product development in the pre vs. post-LLM world

(39:53) The impact of AI hype on Sprig's product development

(45:36) Balancing AI automation with user-psychology

(48:47) Do recent LLMs reduce Sprig's competitive advantage?

(51:00) The importance of "selling the vision" to customers

(54:40) How Sprig structures teams

(57:25) How Sprig upskills all team members on AI

(60:25) 3 key tips for companies trying to navigate AI

(66:05) Major limitations with LLMs right now

(70:27) The future of AI and the future of Sprig

]]> 4605 An org-design masterclass from a Square GM | Saumil Mehta Saumil Mehta is the GM of Square’s flagship point-of-sale business, as well as CRM, Square Staff, and Square Online. Before Square, Saumil was the Founder and CEO of LocBox, which raised over $5.1M, and helped offline/local businesses run multi-channel marketing campaigns, all from one universal dashboard. Saumil has now been a leader at Square for 8+ years, and has overseen many complex re-orgs. These experiences have shaped Saumil into an all-round org-design expert. In today’s episode we discuss: The principles of effective org design Signs your company needs a re-org Square’s GM-led org design, and the reasoning behind it Lessons on incentive-design, pricing, planning, and decision-making at scale The step-by-step process behind a recent re-org at Square 5 lessons from Alyssa Henry, CEO at Square Referenced: Alyssa Henry, CEO at Square: https://www.linkedin.com/in/alyssa-henry-0905692 Saumil’s 6 key principles for effective re-orgs: https://medium.com/@saumil/avoid-the-reorg-from-hell-with-six-key-principles-f8c9cbdfb0bd Saumil’s blog post about “Building Better Products with Escalation”: https://medium.com/swlh/well-that-escalated-quickly-building-better-products-with-escalation-feb259d733c9 Square: https://squareup.com/gb/en Where to find Saumil Mehta: Twitter: https://twitter.com/saumil Linkedin: https://www.linkedin.com/in/saumilmehta1/ Blog: https://medium.com/@saumil Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps [00:02:22] Intro [00:04:20] The principles of effective org design [00:04:32] #1 Align on goals [00:06:14] #2 Separate design considerations from human considerations [00:08:03] #3 Define clear reasons each team exists [00:09:21] #4 Design for durability [00:09:49] #5 Be very intentional with comms [00:10:14] Some stories behind the principles [00:13:55] How to know when you need a re-org [00:16:14] Managing inevitable tradeoffs in org design [00:20:45] Square's "GM-led" structure [00:23:05] Why Square centralized GTM [00:25:39] Managing pricing and packaging across a complex org [00:29:28] Examples of Square's written principles [00:31:19] How Square determines what each GM owns [00:38:35] Collaboration across GMs and products [00:40:32] Key lessons on planning and decision-making at scale [00:43:15] Designing incentives across a massive org [00:49:03] Two reasons GM structures go wrong [00:52:03] 6 Step re-org walkthrough [00:52:37] Step 1: Triggering the re-org [00:53:59] Step 2: Sketching a proposed org design [00:56:17] Step 3: Checking against key criteria [00:59:22] Step 4: Finalizing approach with leadership [01:00:04] Step 5: Planning comms [01:01:58] Step 6: Executing comms [01:04:20] Signals a re-org worked vs failed [01:07:13] 5 lessons from Alyssa Henry, CEO at Square Thu, 31 Aug 2023 08:00:00 -0000 Org-design masterclass from a Square GM | Saumil Mehta full 103 First Round Saumil Mehta is the GM of Square’s flagship point-of-sale business, as well as CRM, Square Staff, and Square Online. Before Square, Saumil was the Founder and CEO of LocBox, which raised over $5.1M, and helped offline/local businesses run multi-channel marketing campaigns, all from one universal dashboard. Saumil has now been a leader at Square for 8+ years, and has overseen many complex re-orgs. These experiences have shaped Saumil into an all-round org-design expert. Saumil Mehta is the GM of Square’s flagship point-of-sale business, as well as CRM, Square Staff, and Square Online. Before Square, Saumil was the Founder and CEO of LocBox, which raised over $5.1M, and helped offline/local businesses run multi-channel marketing campaigns, all from one universal dashboard. Saumil has now been a leader at Square for 8+ years, and has overseen many complex re-orgs. These experiences have shaped Saumil into an all-round org-design expert. In today’s episode we discuss: The principles of effective org design Signs your company needs a re-org Square’s GM-led org design, and the reasoning behind it Lessons on incentive-design, pricing, planning, and decision-making at scale The step-by-step process behind a recent re-org at Square 5 lessons from Alyssa Henry, CEO at Square Referenced: Alyssa Henry, CEO at Square: https://www.linkedin.com/in/alyssa-henry-0905692 Saumil’s 6 key principles for effective re-orgs: https://medium.com/@saumil/avoid-the-reorg-from-hell-with-six-key-principles-f8c9cbdfb0bd Saumil’s blog post about “Building Better Products with Escalation”: https://medium.com/swlh/well-that-escalated-quickly-building-better-products-with-escalation-feb259d733c9 Square: https://squareup.com/gb/en Where to find Saumil Mehta: Twitter: https://twitter.com/saumil Linkedin: https://www.linkedin.com/in/saumilmehta1/ Blog: https://medium.com/@saumil Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps [00:02:22] Intro [00:04:20] The principles of effective org design [00:04:32] #1 Align on goals [00:06:14] #2 Separate design considerations from human considerations [00:08:03] #3 Define clear reasons each team exists [00:09:21] #4 Design for durability [00:09:49] #5 Be very intentional with comms [00:10:14] Some stories behind the principles [00:13:55] How to know when you need a re-org [00:16:14] Managing inevitable tradeoffs in org design [00:20:45] Square's "GM-led" structure [00:23:05] Why Square centralized GTM [00:25:39] Managing pricing and packaging across a complex org [00:29:28] Examples of Square's written principles [00:31:19] How Square determines what each GM owns [00:38:35] Collaboration across GMs and products [00:40:32] Key lessons on planning and decision-making at scale [00:43:15] Designing incentives across a massive org [00:49:03] Two reasons GM structures go wrong [00:52:03] 6 Step re-org walkthrough [00:52:37] Step 1: Triggering the re-org [00:53:59] Step 2: Sketching a proposed org design [00:56:17] Step 3: Checking against key criteria [00:59:22] Step 4: Finalizing approach with leadership [01:00:04] Step 5: Planning comms [01:01:58] Step 6: Executing comms [01:04:20] Signals a re-org worked vs failed [01:07:13] 5 lessons from Alyssa Henry, CEO at Square Saumil Mehta is the GM of Square’s flagship point-of-sale business, as well as CRM, Square Staff, and Square Online. Before Square, Saumil was the Founder and CEO of LocBox, which raised over $5.1M, and helped offline/local businesses run multi-channel marketing campaigns, all from one universal dashboard. Saumil has now been a leader at Square for 8+ years, and has overseen many complex re-orgs. These experiences have shaped Saumil into an all-round org-design expert.

In today’s episode we discuss:

  • The principles of effective org design
  • Signs your company needs a re-org
  • Square’s GM-led org design, and the reasoning behind it
  • Lessons on incentive-design, pricing, planning, and decision-making at scale
  • The step-by-step process behind a recent re-org at Square
  • 5 lessons from Alyssa Henry, CEO at Square


Referenced:

Alyssa Henry, CEO at Square: https://www.linkedin.com/in/alyssa-henry-0905692

Saumil’s 6 key principles for effective re-orgs: https://medium.com/@saumil/avoid-the-reorg-from-hell-with-six-key-principles-f8c9cbdfb0bd

Saumil’s blog post about “Building Better Products with Escalation”: https://medium.com/swlh/well-that-escalated-quickly-building-better-products-with-escalation-feb259d733c9

Square: https://squareup.com/gb/en


Where to find Saumil Mehta:

Twitter: https://twitter.com/saumil

Linkedin: https://www.linkedin.com/in/saumilmehta1/

Blog: https://medium.com/@saumil


Where to find Brett Berson:

Twitter: https://twitter.com/brettberson

LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/


Where to find First Round Capital:

Website: https://firstround.com/

First Round Review: https://review.firstround.com/

Twitter: https://twitter.com/firstround

Youtube: https://www.youtube.com/@FirstRoundCapital

This podcast on all platforms: https://review.firstround.com/podcast


Timestamps

[00:02:22] Intro

[00:04:20] The principles of effective org design

[00:04:32] #1 Align on goals

[00:06:14] #2 Separate design considerations from human considerations

[00:08:03] #3 Define clear reasons each team exists

[00:09:21] #4 Design for durability

[00:09:49] #5 Be very intentional with comms

[00:10:14] Some stories behind the principles

[00:13:55] How to know when you need a re-org

[00:16:14] Managing inevitable tradeoffs in org design

[00:20:45] Square's "GM-led" structure

[00:23:05] Why Square centralized GTM

[00:25:39] Managing pricing and packaging across a complex org

[00:29:28] Examples of Square's written principles

[00:31:19] How Square determines what each GM owns

[00:38:35] Collaboration across GMs and products

[00:40:32] Key lessons on planning and decision-making at scale

[00:43:15] Designing incentives across a massive org

[00:49:03] Two reasons GM structures go wrong

[00:52:03] 6 Step re-org walkthrough

[00:52:37] Step 1: Triggering the re-org

[00:53:59] Step 2: Sketching a proposed org design

[00:56:17] Step 3: Checking against key criteria

[00:59:22] Step 4: Finalizing approach with leadership

[01:00:04] Step 5: Planning comms

[01:01:58] Step 6: Executing comms

[01:04:20] Signals a re-org worked vs failed

[01:07:13] 5 lessons from Alyssa Henry, CEO at Square

]]> 4480 How to supercharge your engineering org | Kellan Elliott-McCrea (Adobe, Dropbox) Kellan Elliott-McCrea is a Head of Engineering at Adobe, overseeing Frame.io, a newly acquired video review and collaboration platform. He is known for his experience and expertise as an engineering leader. He was previously a VPE at Dropbox, and CTO at Etsy where he built and led a team of 300 people, from tech and platform reboot through to IPO. Kellan also built and scaled teams at Flickr, and has a coaching and advising practice for companies looking to supercharge their engineering teams.  In today's episode, we discuss: How software engineering has changed in the last 10-15 years The future of software engineering, and the impact of AI The importance of alignment and tactics for achieving it How to think about and enable engineering productivity Lessons on culture from Adobe, Dropbox, and Flickr Concrete tips for being a better manager Rituals for building business literacy throughout an org Referenced: Adobe: https://www.adobe.com Dropbox: https://www.dropbox.com/ Flickr: https://www.flickr.com/ Frame: https://www.frame.io/ How Complex Systems Fail, by Richard I. Cook, MD: https://how.complexsystems.fail/ How Etsy Grew their Number of Female Engineers by Almost 500% in One Year https://review.firstround.com/How-Etsy-Grew-their-Number-of-Female-Engineers-by-500-in-One-Year Where to find Kellan Elliott-McCrea: Twitter: https://www.twitter.com/kellan LinkedIn: https://www.linkedin.com/in/kellanem Website: https://kellanem.com/ Personal blog: https://laughingmeme.org/ Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Timestamps: [00:02:58] Engineering orgs now vs 15 years ago [00:05:57] Why engineering teams are bigger despite better tools [00:10:45] How to think about engineering productivity [00:15:50] Questioning common compensation models [00:19:39] Slow teams are misaligned teams [00:23:56] How to achieve alignment in engineering teams [00:29:12] How to co-ordinate better across teams [00:35:23] Why so few companies successfully go multi-product [00:38:02] Which elements of successful orgs replicate? [00:41:53] How to approach a new org system at a new company [00:45:48] The value of information sharing and coaching [00:48:55] Best practices for communicating with and across teams [00:51:05] How to approach disagreements [00:54:27] What high-quality engineering management looks like [00:58:37] How to increase organizational capacity [00:63:20] Tactics and rituals for enabling effective teams [00:66:05] How to build business literacy [00:68:30] Kellan's biggest inspirations Thu, 17 Aug 2023 08:00:00 -0000 How to supercharge your engineering org | Kellan Elliott-McCrea (Adobe, Dropbox) full 102 First Round Kellan Elliott-McCrea is a Head of Engineering at Adobe. He discusses how software engineering has changed in the last 10-15 years, the importance of alignment and tactics for achieving it, how to think about and enable engineering productivity, and lessons on culture from Adobe, Dropbox and Flickr. Kellan Elliott-McCrea is a Head of Engineering at Adobe, overseeing Frame.io, a newly acquired video review and collaboration platform. He is known for his experience and expertise as an engineering leader. He was previously a VPE at Dropbox, and CTO at Etsy where he built and led a team of 300 people, from tech and platform reboot through to IPO. Kellan also built and scaled teams at Flickr, and has a coaching and advising practice for companies looking to supercharge their engineering teams.  In today's episode, we discuss: How software engineering has changed in the last 10-15 years The future of software engineering, and the impact of AI The importance of alignment and tactics for achieving it How to think about and enable engineering productivity Lessons on culture from Adobe, Dropbox, and Flickr Concrete tips for being a better manager Rituals for building business literacy throughout an org Referenced: Adobe: https://www.adobe.com Dropbox: https://www.dropbox.com/ Flickr: https://www.flickr.com/ Frame: https://www.frame.io/ How Complex Systems Fail, by Richard I. Cook, MD: https://how.complexsystems.fail/ How Etsy Grew their Number of Female Engineers by Almost 500% in One Year https://review.firstround.com/How-Etsy-Grew-their-Number-of-Female-Engineers-by-500-in-One-Year Where to find Kellan Elliott-McCrea: Twitter: https://www.twitter.com/kellan LinkedIn: https://www.linkedin.com/in/kellanem Website: https://kellanem.com/ Personal blog: https://laughingmeme.org/ Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Timestamps: [00:02:58] Engineering orgs now vs 15 years ago [00:05:57] Why engineering teams are bigger despite better tools [00:10:45] How to think about engineering productivity [00:15:50] Questioning common compensation models [00:19:39] Slow teams are misaligned teams [00:23:56] How to achieve alignment in engineering teams [00:29:12] How to co-ordinate better across teams [00:35:23] Why so few companies successfully go multi-product [00:38:02] Which elements of successful orgs replicate? [00:41:53] How to approach a new org system at a new company [00:45:48] The value of information sharing and coaching [00:48:55] Best practices for communicating with and across teams [00:51:05] How to approach disagreements [00:54:27] What high-quality engineering management looks like [00:58:37] How to increase organizational capacity [00:63:20] Tactics and rituals for enabling effective teams [00:66:05] How to build business literacy [00:68:30] Kellan's biggest inspirations Kellan Elliott-McCrea is a Head of Engineering at Adobe, overseeing Frame.io, a newly acquired video review and collaboration platform. He is known for his experience and expertise as an engineering leader. He was previously a VPE at Dropbox, and CTO at Etsy where he built and led a team of 300 people, from tech and platform reboot through to IPO. Kellan also built and scaled teams at Flickr, and has a coaching and advising practice for companies looking to supercharge their engineering teams. 


In today's episode, we discuss:

  • How software engineering has changed in the last 10-15 years
  • The future of software engineering, and the impact of AI
  • The importance of alignment and tactics for achieving it
  • How to think about and enable engineering productivity
  • Lessons on culture from Adobe, Dropbox, and Flickr
  • Concrete tips for being a better manager
  • Rituals for building business literacy throughout an org


Referenced:

Adobe: https://www.adobe.com

Dropbox: https://www.dropbox.com/

Flickr: https://www.flickr.com/

Frame: https://www.frame.io/

How Complex Systems Fail, by Richard I. Cook, MD: https://how.complexsystems.fail/

How Etsy Grew their Number of Female Engineers by Almost 500% in One Year https://review.firstround.com/How-Etsy-Grew-their-Number-of-Female-Engineers-by-500-in-One-Year


Where to find Kellan Elliott-McCrea:

Twitter: https://www.twitter.com/kellan

LinkedIn: https://www.linkedin.com/in/kellanem

Website: https://kellanem.com/

Personal blog: https://laughingmeme.org/

Where to find Brett Berson:

Twitter: https://twitter.com/brettberson

LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/


Timestamps:

[00:02:58] Engineering orgs now vs 15 years ago

[00:05:57] Why engineering teams are bigger despite better tools

[00:10:45] How to think about engineering productivity

[00:15:50] Questioning common compensation models

[00:19:39] Slow teams are misaligned teams

[00:23:56] How to achieve alignment in engineering teams

[00:29:12] How to co-ordinate better across teams

[00:35:23] Why so few companies successfully go multi-product

[00:38:02] Which elements of successful orgs replicate?

[00:41:53] How to approach a new org system at a new company

[00:45:48] The value of information sharing and coaching

[00:48:55] Best practices for communicating with and across teams

[00:51:05] How to approach disagreements

[00:54:27] What high-quality engineering management looks like

[00:58:37] How to increase organizational capacity

[00:63:20] Tactics and rituals for enabling effective teams

[00:66:05] How to build business literacy

[00:68:30] Kellan's biggest inspirations

]]> 4407 The zero to one B2B marketing playbook | Alex Kracov (Lattice, Dock) Alex Kracov is the CEO and Co-Founder at Dock, and the former VP of Marketing at Lattice. Alex joined Lattice as the first marketer and third employee, and he helped to grow the business from seed to 1850+ customers. Prior to Lattice, Alex was a consultant at Blue State Digital — the team that elected President Obama and orchestrated projects at Google. Since leaving Lattice in 2021, Alex co-founded Dock, a B2B platform that has streamlined the customer buying experience for clients like Loom, Origin, and Instabug.  In today's episode, we discuss: The 2023 SaaS marketing playbook How to start your early-stage B2B marketing How to prioritize resources across multiple marketing bets How to think about attribution Lattice’s unorthodox million-dollar marketing campaign How to hire for early marketing roles What makes a standout marketer Advice for building your first website Referenced: Dock: https://www.dock.us/ Lattice: https://lattice.com/ Jack Altman: https://www.linkedin.com/in/jackealtman J Zac Stein: https://www.linkedin.com/in/jzacstein Where to find Alex Kracov: Twitter: https://twitter.com/kracov/ LinkedIn: https://www.linkedin.com/in/alexkracov Website: https://www.kracov.co/ Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Timestamps: [00:00:00] Intro [00:02:45] The challenges and opportunities in early-stage B2B marketing [00:05:13] How to think about short-term versus long-term marketing goals [00:07:31] Allocating resources across marketing bets [00:09:13] Signs your marketing is working [00:11:20] The most underutilized marketing strategy [00:13:03] Creating your company’s first website [00:14:22] How Lattice formed its brand messaging and positioning [00:18:22] Dock’s innovative approach to marketing software [00:20:14] The first thing people should see on your website [00:23:10] Lattice’s most successful early-stage marketing tactics [00:28:05] Determining which marketing strategies are still relevant [00:30:25] Lattice’s unorthodox million-dollar marketing campaign [00:33:26] Why Alex had an outsized impact at Lattice [00:37:05] Lessons from his first marketing hires [00:39:41] When to scale your marketing team [00:40:55] Building an effective early-stage marketing team [00:42:30] A tough conversation with the CEO & Co-founder of Lattice [00:44:46] Achieving early-stage marketing alignment [00:46:20] Transitioning from employee to entrepreneur [00:49:19] Getting the most out of conferences [00:50:47] Selecting marketing channels in the early stages [00:52:44] Hiring marketers for experience versus potential [00:56:34] The 2023 SaaS marketing stack [00:58:19] Advice for Zero to One marketing [00:60:46] What successful B2B marketing looks like Thu, 10 Aug 2023 08:00:00 -0000 The zero to one B2B marketing playbook | Alex Kracov (Lattice, Dock) full First Round The Zero to One B2B marketing playbook | Alex Kracov (Lattice, Dock) Alex Kracov is the CEO and Co-Founder at Dock, and the former VP of Marketing at Lattice. Alex joined Lattice as the first marketer and third employee, and he helped to grow the business from seed to 1850+ customers. Prior to Lattice, Alex was a consultant at Blue State Digital — the team that elected President Obama and orchestrated projects at Google. Since leaving Lattice in 2021, Alex co-founded Dock, a B2B platform that has streamlined the customer buying experience for clients like Loom, Origin, and Instabug.  In today's episode, we discuss: The 2023 SaaS marketing playbook How to start your early-stage B2B marketing How to prioritize resources across multiple marketing bets How to think about attribution Lattice’s unorthodox million-dollar marketing campaign How to hire for early marketing roles What makes a standout marketer Advice for building your first website Referenced: Dock: https://www.dock.us/ Lattice: https://lattice.com/ Jack Altman: https://www.linkedin.com/in/jackealtman J Zac Stein: https://www.linkedin.com/in/jzacstein Where to find Alex Kracov: Twitter: https://twitter.com/kracov/ LinkedIn: https://www.linkedin.com/in/alexkracov Website: https://www.kracov.co/ Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Timestamps: [00:00:00] Intro [00:02:45] The challenges and opportunities in early-stage B2B marketing [00:05:13] How to think about short-term versus long-term marketing goals [00:07:31] Allocating resources across marketing bets [00:09:13] Signs your marketing is working [00:11:20] The most underutilized marketing strategy [00:13:03] Creating your company’s first website [00:14:22] How Lattice formed its brand messaging and positioning [00:18:22] Dock’s innovative approach to marketing software [00:20:14] The first thing people should see on your website [00:23:10] Lattice’s most successful early-stage marketing tactics [00:28:05] Determining which marketing strategies are still relevant [00:30:25] Lattice’s unorthodox million-dollar marketing campaign [00:33:26] Why Alex had an outsized impact at Lattice [00:37:05] Lessons from his first marketing hires [00:39:41] When to scale your marketing team [00:40:55] Building an effective early-stage marketing team [00:42:30] A tough conversation with the CEO & Co-founder of Lattice [00:44:46] Achieving early-stage marketing alignment [00:46:20] Transitioning from employee to entrepreneur [00:49:19] Getting the most out of conferences [00:50:47] Selecting marketing channels in the early stages [00:52:44] Hiring marketers for experience versus potential [00:56:34] The 2023 SaaS marketing stack [00:58:19] Advice for Zero to One marketing [00:60:46] What successful B2B marketing looks like Alex Kracov is the CEO and Co-Founder at Dock, and the former VP of Marketing at Lattice. Alex joined Lattice as the first marketer and third employee, and he helped to grow the business from seed to 1850+ customers. Prior to Lattice, Alex was a consultant at Blue State Digital — the team that elected President Obama and orchestrated projects at Google. Since leaving Lattice in 2021, Alex co-founded Dock, a B2B platform that has streamlined the customer buying experience for clients like Loom, Origin, and Instabug. 


In today's episode, we discuss:

  • The 2023 SaaS marketing playbook
  • How to start your early-stage B2B marketing
  • How to prioritize resources across multiple marketing bets
  • How to think about attribution
  • Lattice’s unorthodox million-dollar marketing campaign
  • How to hire for early marketing roles
  • What makes a standout marketer
  • Advice for building your first website


Referenced:


Where to find Alex Kracov:

Twitter: https://twitter.com/kracov/

LinkedIn: https://www.linkedin.com/in/alexkracov

Website: https://www.kracov.co/


Where to find Brett Berson:

Twitter: https://twitter.com/brettberson

LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/


Timestamps:

[00:00:00] Intro

[00:02:45] The challenges and opportunities in early-stage B2B marketing

[00:05:13] How to think about short-term versus long-term marketing goals

[00:07:31] Allocating resources across marketing bets

[00:09:13] Signs your marketing is working

[00:11:20] The most underutilized marketing strategy

[00:13:03] Creating your company’s first website

[00:14:22] How Lattice formed its brand messaging and positioning

[00:18:22] Dock’s innovative approach to marketing software

[00:20:14] The first thing people should see on your website

[00:23:10] Lattice’s most successful early-stage marketing tactics

[00:28:05] Determining which marketing strategies are still relevant

[00:30:25] Lattice’s unorthodox million-dollar marketing campaign

[00:33:26] Why Alex had an outsized impact at Lattice

[00:37:05] Lessons from his first marketing hires

[00:39:41] When to scale your marketing team

[00:40:55] Building an effective early-stage marketing team

[00:42:30] A tough conversation with the CEO & Co-founder of Lattice

[00:44:46] Achieving early-stage marketing alignment

[00:46:20] Transitioning from employee to entrepreneur

[00:49:19] Getting the most out of conferences

[00:50:47] Selecting marketing channels in the early stages

[00:52:44] Hiring marketers for experience versus potential

[00:56:34] The 2023 SaaS marketing stack

[00:58:19] Advice for Zero to One marketing

[00:60:46] What successful B2B marketing looks like

]]> 3829 Lessons from Loom on product strategy, organizational leadership, and cross-functional performance | Anique Drumright (COO at Loom) Anique Drumright is the COO at Loom, a video communication tool for streamlining workflows. Loom has raised over $200M, and was last valued at $1.5B. Anique has a proven track record across product development, executive leadership, and building high-performing organizations. Before joining Loom, Anique was the VP of Product at TripActions, where she scaled the team over 8x globally, and she has also held multiple roles at Uber. In today's episode, we discuss: Best-practice product management How to achieve alignment at scale The importance of cross-functional performance Anique's unique approach to finding top organizational talent How to hire for roles outside your area of expertise Common fail cases with internal and external recruitment Tactics for effective interviews Referenced: Loom: https://www.loom.com/ Navan (formerly TripActions): https://navan.com/ Teach for America: https://www.teachforamerica.org/ Uber: https://www.uber.com/ Where to find Anique Drumright: Twitter: https://twitter.com/aniqued LinkedIn: https://www.linkedin.com/in/anique-drumright-53978a1a Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Timestamps: [00:03:00] The similarities and differences between PM and executive leadership roles [00:06:53] How Loom uses storytelling when launching a product [00:10:01] Managing cross-functional scope and performance [00:13:41] Goal-setting with functional leads [00:16:59] The importance and difficulty of organizational alignment [00:20:40] How Uber achieved alignment at scale [00:24:06] Rituals for staying aligned [00:25:23] Loom's winning one-on-one format [00:27:49] When and how to help functional leads [00:29:13] Hiring for roles outside your area of expertise [00:32:55] Go-to interview questions for prospective leaders [00:33:55] Changing the hiring process for roles outside your area of expertise [00:36:09] Common patterns of failed external hires [00:37:40] Common patterns of failed internal hires [00:39:05] Avoiding over-promotion in your organization [00:40:51] What inspires people in a company [00:45:40] Tactics for getting honest answers in interviews [00:47:12] Asking the right questions during reference checks [00:51:29] A month in the life of a COO [00:52:52] The importance of employee energy levels [00:54:53] Loom's leadership dynamics and why it works [00:57:30] People who had an outsized impact on Anique's career Thu, 03 Aug 2023 08:00:00 -0000 Lessons from Loom on product strategy, organizational leadership, and cross-functional performance | Anique Drumright (COO at Loom) full First Round Anique Drumright is Chief Operating Officer at Loom. She shares insights and strategies on how Loom approaches product design and strategy, how to recruit and build a high-performing cross-functional org, and how to structure effective internal meetings. Anique Drumright is the COO at Loom, a video communication tool for streamlining workflows. Loom has raised over $200M, and was last valued at $1.5B. Anique has a proven track record across product development, executive leadership, and building high-performing organizations. Before joining Loom, Anique was the VP of Product at TripActions, where she scaled the team over 8x globally, and she has also held multiple roles at Uber. In today's episode, we discuss: Best-practice product management How to achieve alignment at scale The importance of cross-functional performance Anique's unique approach to finding top organizational talent How to hire for roles outside your area of expertise Common fail cases with internal and external recruitment Tactics for effective interviews Referenced: Loom: https://www.loom.com/ Navan (formerly TripActions): https://navan.com/ Teach for America: https://www.teachforamerica.org/ Uber: https://www.uber.com/ Where to find Anique Drumright: Twitter: https://twitter.com/aniqued LinkedIn: https://www.linkedin.com/in/anique-drumright-53978a1a Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Timestamps: [00:03:00] The similarities and differences between PM and executive leadership roles [00:06:53] How Loom uses storytelling when launching a product [00:10:01] Managing cross-functional scope and performance [00:13:41] Goal-setting with functional leads [00:16:59] The importance and difficulty of organizational alignment [00:20:40] How Uber achieved alignment at scale [00:24:06] Rituals for staying aligned [00:25:23] Loom's winning one-on-one format [00:27:49] When and how to help functional leads [00:29:13] Hiring for roles outside your area of expertise [00:32:55] Go-to interview questions for prospective leaders [00:33:55] Changing the hiring process for roles outside your area of expertise [00:36:09] Common patterns of failed external hires [00:37:40] Common patterns of failed internal hires [00:39:05] Avoiding over-promotion in your organization [00:40:51] What inspires people in a company [00:45:40] Tactics for getting honest answers in interviews [00:47:12] Asking the right questions during reference checks [00:51:29] A month in the life of a COO [00:52:52] The importance of employee energy levels [00:54:53] Loom's leadership dynamics and why it works [00:57:30] People who had an outsized impact on Anique's career Anique Drumright is the COO at Loom, a video communication tool for streamlining workflows. Loom has raised over $200M, and was last valued at $1.5B. Anique has a proven track record across product development, executive leadership, and building high-performing organizations. Before joining Loom, Anique was the VP of Product at TripActions, where she scaled the team over 8x globally, and she has also held multiple roles at Uber.


In today's episode, we discuss:

  • Best-practice product management
  • How to achieve alignment at scale
  • The importance of cross-functional performance
  • Anique's unique approach to finding top organizational talent
  • How to hire for roles outside your area of expertise
  • Common fail cases with internal and external recruitment
  • Tactics for effective interviews


Referenced:


Where to find Anique Drumright:

Twitter: https://twitter.com/aniqued

LinkedIn: https://www.linkedin.com/in/anique-drumright-53978a1a


Where to find Brett Berson:

Twitter: https://twitter.com/brettberson

LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/


Timestamps:

[00:03:00] The similarities and differences between PM and executive leadership roles

[00:06:53] How Loom uses storytelling when launching a product

[00:10:01] Managing cross-functional scope and performance

[00:13:41] Goal-setting with functional leads

[00:16:59] The importance and difficulty of organizational alignment

[00:20:40] How Uber achieved alignment at scale

[00:24:06] Rituals for staying aligned

[00:25:23] Loom's winning one-on-one format

[00:27:49] When and how to help functional leads

[00:29:13] Hiring for roles outside your area of expertise

[00:32:55] Go-to interview questions for prospective leaders

[00:33:55] Changing the hiring process for roles outside your area of expertise

[00:36:09] Common patterns of failed external hires

[00:37:40] Common patterns of failed internal hires

[00:39:05] Avoiding over-promotion in your organization

[00:40:51] What inspires people in a company

[00:45:40] Tactics for getting honest answers in interviews

[00:47:12] Asking the right questions during reference checks

[00:51:29] A month in the life of a COO

[00:52:52] The importance of employee energy levels

[00:54:53] Loom's leadership dynamics and why it works

[00:57:30] People who had an outsized impact on Anique's career

]]> 3690 Lessons from Slack on decision making, product-led growth, and taking big swings — Noah Desai Weiss Noah Desai Weiss is the Chief Product Officer of Slack, and has an accomplished track record inside and outside of the company. He started Slack’s Search, Learning, and Intelligence division, led the Self-Service (SMB) Business, and led the Expansion and Virtual HQ product areas (responsible for Huddles, Clips, and more). Before joining Slack, Noah was the SVP of Product Management at Foursquare (raised over $390m), and was a Product Manager at Google. In today's episode, we discuss: When to use intuition vs data to drive decisions The most underrated traits in a remote work environment How Slack runs product reviews The importance of a team’s “vibe” Managing pace vs accuracy in decision-making Balancing "big swings" with incremental improvements Advice on product-led vs sales-led growth Curious to learn more about Slack? You can try Slack Pro and get 50% off using this link. Referenced: Creative Selection - Inside Apple's Design Process During the Golden Age of Steve Jobs: https://www.amazon.com/Creative-Selection-Inside-Apples-Process/dp/1250194466 Salesforce acquires Slack: https://slack.com/blog/news/salesforce-completes-acquisition-of-slack Thinking in Bets - Making Smarter Decisions When You Don't Have All the Facts: https://www.amazon.com/Thinking-Bets-Making-Smarter-Decisions-ebook/dp/B074DG9LQF Where to find Noah Weiss: Twitter: https://twitter.com/noah_weiss LinkedIn: https://www.linkedin.com/in/noahw/ Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Timestamps: [2:46] Not all decisions should be data-driven [3:46] When to use data vs intuition to drive decisions [9:15] Taste and judgment are learnable [11:47] How Slack scales intuition across their product org [14:58] Challenges of intuition-led product building [16:43] Matching people to data vs intuition-driven work [19:19] underrated qualities for remote workers [21:34] What's special about Slack's approach to product? [23:33] Which products should focus on end-users versus executives [26:38] What Slack learns from Salesforce [31:44] Pricing lessons from Salesforce and Marc Andreessen [34:10] How Slack runs product reviews [37:02] What creates good vibes in a product team [40:17] Managing pace vs accuracy in decision-making [46:29] Rituals for good decision-making [50:20] Balancing "big swings" with incremental improvements [55:30] Slack's biggest philosophy change [60:05] Slack's humility and why it matters [61:43] Advice for thinking about product-led vs sales-led growth [01:08:14] How to build product with a product-focussed founder [01:12:46] People who made an outsized impact on Noah's career Thu, 13 Jul 2023 08:00:00 -0000 Lessons from Slack on decision making, product-led growth, and taking big swings — Noah Desai Weiss full First Round Noah Desai Weiss is Chief Product Officer at Slack. He shares frameworks and strategies on how Slack’s product org approaches decision making, what PLG for a horizontal SaaS product looks like, and when it pays off to take big bets. Noah Desai Weiss is the Chief Product Officer of Slack, and has an accomplished track record inside and outside of the company. He started Slack’s Search, Learning, and Intelligence division, led the Self-Service (SMB) Business, and led the Expansion and Virtual HQ product areas (responsible for Huddles, Clips, and more). Before joining Slack, Noah was the SVP of Product Management at Foursquare (raised over $390m), and was a Product Manager at Google. In today's episode, we discuss: When to use intuition vs data to drive decisions The most underrated traits in a remote work environment How Slack runs product reviews The importance of a team’s “vibe” Managing pace vs accuracy in decision-making Balancing "big swings" with incremental improvements Advice on product-led vs sales-led growth Curious to learn more about Slack? You can try Slack Pro and get 50% off using this link. Referenced: Creative Selection - Inside Apple's Design Process During the Golden Age of Steve Jobs: https://www.amazon.com/Creative-Selection-Inside-Apples-Process/dp/1250194466 Salesforce acquires Slack: https://slack.com/blog/news/salesforce-completes-acquisition-of-slack Thinking in Bets - Making Smarter Decisions When You Don't Have All the Facts: https://www.amazon.com/Thinking-Bets-Making-Smarter-Decisions-ebook/dp/B074DG9LQF Where to find Noah Weiss: Twitter: https://twitter.com/noah_weiss LinkedIn: https://www.linkedin.com/in/noahw/ Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Timestamps: [2:46] Not all decisions should be data-driven [3:46] When to use data vs intuition to drive decisions [9:15] Taste and judgment are learnable [11:47] How Slack scales intuition across their product org [14:58] Challenges of intuition-led product building [16:43] Matching people to data vs intuition-driven work [19:19] underrated qualities for remote workers [21:34] What's special about Slack's approach to product? [23:33] Which products should focus on end-users versus executives [26:38] What Slack learns from Salesforce [31:44] Pricing lessons from Salesforce and Marc Andreessen [34:10] How Slack runs product reviews [37:02] What creates good vibes in a product team [40:17] Managing pace vs accuracy in decision-making [46:29] Rituals for good decision-making [50:20] Balancing "big swings" with incremental improvements [55:30] Slack's biggest philosophy change [60:05] Slack's humility and why it matters [61:43] Advice for thinking about product-led vs sales-led growth [01:08:14] How to build product with a product-focussed founder [01:12:46] People who made an outsized impact on Noah's career Noah Desai Weiss is the Chief Product Officer of Slack, and has an accomplished track record inside and outside of the company. He started Slack’s Search, Learning, and Intelligence division, led the Self-Service (SMB) Business, and led the Expansion and Virtual HQ product areas (responsible for Huddles, Clips, and more). Before joining Slack, Noah was the SVP of Product Management at Foursquare (raised over $390m), and was a Product Manager at Google.


In today's episode, we discuss:

  • When to use intuition vs data to drive decisions
  • The most underrated traits in a remote work environment
  • How Slack runs product reviews
  • The importance of a team’s “vibe”
  • Managing pace vs accuracy in decision-making
  • Balancing "big swings" with incremental improvements
  • Advice on product-led vs sales-led growth


Curious to learn more about Slack? You can try Slack Pro and get 50% off using this link.


Referenced:

Creative Selection - Inside Apple's Design Process During the Golden Age of Steve Jobs: https://www.amazon.com/Creative-Selection-Inside-Apples-Process/dp/1250194466

Salesforce acquires Slack: https://slack.com/blog/news/salesforce-completes-acquisition-of-slack

Thinking in Bets - Making Smarter Decisions When You Don't Have All the Facts: https://www.amazon.com/Thinking-Bets-Making-Smarter-Decisions-ebook/dp/B074DG9LQF


Where to find Noah Weiss:

Twitter: https://twitter.com/noah_weiss

LinkedIn: https://www.linkedin.com/in/noahw/

Where to find Brett Berson:

Twitter: https://twitter.com/brettberson

LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/


Timestamps:

[2:46] Not all decisions should be data-driven

[3:46] When to use data vs intuition to drive decisions

[9:15] Taste and judgment are learnable

[11:47] How Slack scales intuition across their product org

[14:58] Challenges of intuition-led product building

[16:43] Matching people to data vs intuition-driven work

[19:19] underrated qualities for remote workers

[21:34] What's special about Slack's approach to product?

[23:33] Which products should focus on end-users versus executives

[26:38] What Slack learns from Salesforce

[31:44] Pricing lessons from Salesforce and Marc Andreessen

[34:10] How Slack runs product reviews

[37:02] What creates good vibes in a product team

[40:17] Managing pace vs accuracy in decision-making

[46:29] Rituals for good decision-making

[50:20] Balancing "big swings" with incremental improvements

[55:30] Slack's biggest philosophy change

[60:05] Slack's humility and why it matters

[61:43] Advice for thinking about product-led vs sales-led growth

[01:08:14] How to build product with a product-focussed founder

[01:12:46] People who made an outsized impact on Noah's career

]]> 4654 Lessons in leadership | Scaling an org, developing yourself, and tactical management advice | Jack Altman (Lattice) Jack Altman is the co-founder and CEO of Lattice, a people success platform for building engaged, high-performing teams. Lattice has raised over $330M, and was last valued at $3B. He is an expert in building company culture, and wrote a book on the topic, titled: “People Strategy”. In today's episode, we discuss: The importance of self-awareness and how to develop it The value of difficult conversations and advice for having them Common mistakes when scaling a company How to approach firing decisions and the associated internal optics How to think about low-performing but “well-liked” employees How to get drastically more out of your team members Adapting to the challenging new economic environment Referenced: Jack’s book: https://www.amazon.com/People-Strategy-Culture-Competitive-Advantage/dp/1119717043 Jack’s company, Lattice: https://lattice.com/ First Round Capital's Newsletter: https://review.firstround.com/newsletter Where to find Jack Altman: LinkedIn: https://www.linkedin.com/in/jackealtman Twitter: https://twitter.com/jaltma Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ In this episode, we cover: (2:40) Founders must continually grow with their company (7:23) How to identify hiring errors vs management errors (9:46) Managing the tension of delegation vs control (11:51) How to cultivate self-awareness (14:59) The one thing founders should never give up (17:22) How to build a product org (19:06) Hot take on micro-management (21:05) The importance of context setting as CEO (22:09) What founder transparency actually means (23:43) Examples of “context setting” as a leader (26:09) The value of uncomfortable conversations (27:16) How to have uncomfortable conversations (28:30) Founders must own their most difficult decisions (31:48) Optimizing speed vs accuracy in decision-making (33:50) The hidden biases in group discussions (35:05) When Jack experimented with removing himself from all meetings (37:48) The most unusual element of Jack’s leadership approach (38:34) 4 pieces of advice for CEOs (41:20) How to talk to customers (42:59) The many sources of learning for CEOs (46:45) Instructive framework for maximizing employee performance (49:56) When long-time employees don’t scale with the company (55:07) How to think about low-performing but “well-liked” employees (58:19) Identifying team members that “aren’t a fit” (59:57) Should you tell people why someone was let go? (62:42) Managing in the challenging new economic environment (68:18) Aligning an employee’s career goals with company goals (74:27) You're probably underestimating your team's potential Thu, 06 Jul 2023 08:00:00 -0000 Lessons in leadership | Scaling an org, developing yourself, and tactical management advice | Jack Altman (Lattice) full First Round Jack Altman is the co-founder and CEO of Lattice, a people success platform for building engaged, high-performing teams. Lattice has raised over $330M, and was last valued at $3B. He is an expert in building company culture, and wrote a book on the topic, titled: “People Strategy”. Jack Altman is the co-founder and CEO of Lattice, a people success platform for building engaged, high-performing teams. Lattice has raised over $330M, and was last valued at $3B. He is an expert in building company culture, and wrote a book on the topic, titled: “People Strategy”. In today's episode, we discuss: The importance of self-awareness and how to develop it The value of difficult conversations and advice for having them Common mistakes when scaling a company How to approach firing decisions and the associated internal optics How to think about low-performing but “well-liked” employees How to get drastically more out of your team members Adapting to the challenging new economic environment Referenced: Jack’s book: https://www.amazon.com/People-Strategy-Culture-Competitive-Advantage/dp/1119717043 Jack’s company, Lattice: https://lattice.com/ First Round Capital's Newsletter: https://review.firstround.com/newsletter Where to find Jack Altman: LinkedIn: https://www.linkedin.com/in/jackealtman Twitter: https://twitter.com/jaltma Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ In this episode, we cover: (2:40) Founders must continually grow with their company (7:23) How to identify hiring errors vs management errors (9:46) Managing the tension of delegation vs control (11:51) How to cultivate self-awareness (14:59) The one thing founders should never give up (17:22) How to build a product org (19:06) Hot take on micro-management (21:05) The importance of context setting as CEO (22:09) What founder transparency actually means (23:43) Examples of “context setting” as a leader (26:09) The value of uncomfortable conversations (27:16) How to have uncomfortable conversations (28:30) Founders must own their most difficult decisions (31:48) Optimizing speed vs accuracy in decision-making (33:50) The hidden biases in group discussions (35:05) When Jack experimented with removing himself from all meetings (37:48) The most unusual element of Jack’s leadership approach (38:34) 4 pieces of advice for CEOs (41:20) How to talk to customers (42:59) The many sources of learning for CEOs (46:45) Instructive framework for maximizing employee performance (49:56) When long-time employees don’t scale with the company (55:07) How to think about low-performing but “well-liked” employees (58:19) Identifying team members that “aren’t a fit” (59:57) Should you tell people why someone was let go? (62:42) Managing in the challenging new economic environment (68:18) Aligning an employee’s career goals with company goals (74:27) You're probably underestimating your team's potential Jack Altman is the co-founder and CEO of Lattice, a people success platform for building engaged, high-performing teams. Lattice has raised over $330M, and was last valued at $3B. He is an expert in building company culture, and wrote a book on the topic, titled: “People Strategy”.


In today's episode, we discuss:

  • The importance of self-awareness and how to develop it
  • The value of difficult conversations and advice for having them
  • Common mistakes when scaling a company
  • How to approach firing decisions and the associated internal optics
  • How to think about low-performing but “well-liked” employees
  • How to get drastically more out of your team members
  • Adapting to the challenging new economic environment


Referenced:

Jack’s book: https://www.amazon.com/People-Strategy-Culture-Competitive-Advantage/dp/1119717043

Jack’s company, Lattice: https://lattice.com/

First Round Capital's Newsletter: https://review.firstround.com/newsletter


Where to find Jack Altman:

LinkedIn: https://www.linkedin.com/in/jackealtman

Twitter: https://twitter.com/jaltma


Where to find Brett Berson:

Twitter: https://twitter.com/brettberson

LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/


In this episode, we cover:

(2:40) Founders must continually grow with their company

(7:23) How to identify hiring errors vs management errors

(9:46) Managing the tension of delegation vs control

(11:51) How to cultivate self-awareness

(14:59) The one thing founders should never give up

(17:22) How to build a product org

(19:06) Hot take on micro-management

(21:05) The importance of context setting as CEO

(22:09) What founder transparency actually means

(23:43) Examples of “context setting” as a leader

(26:09) The value of uncomfortable conversations

(27:16) How to have uncomfortable conversations

(28:30) Founders must own their most difficult decisions

(31:48) Optimizing speed vs accuracy in decision-making

(33:50) The hidden biases in group discussions

(35:05) When Jack experimented with removing himself from all meetings

(37:48) The most unusual element of Jack’s leadership approach

(38:34) 4 pieces of advice for CEOs

(41:20) How to talk to customers

(42:59) The many sources of learning for CEOs

(46:45) Instructive framework for maximizing employee performance

(49:56) When long-time employees don’t scale with the company

(55:07) How to think about low-performing but “well-liked” employees

(58:19) Identifying team members that “aren’t a fit”

(59:57) Should you tell people why someone was let go?

(62:42) Managing in the challenging new economic environment

(68:18) Aligning an employee’s career goals with company goals

(74:27) You're probably underestimating your team's potential

]]> 4703 Lessons from Stripe on adding new products - Assessing ideas, structuring teams, and tactics for product reviews | Tara Seshan (Watershed, Stripe) Tara Seshan is the Head of Product at Watershed, a climate platform that companies use to measure, report, and reduce their carbon emissions. Before joining Watershed, Tara was Head of Product at Stripe throughout the launch of Stripe Billing and Stripe Treasury. As a Thiel Fellow and experienced multi-product builder, Tara brings a wealth of experience with 0-1 SaaS products. In today's episode, we discuss: The different types of multi-product strategies. Stories from Stripe’s multi-product success. How to allocate resources across new and existing products. How to structure teams for launching new products. The best personas for building new products and the hiring tactics for finding those people. Common challenges when going from single to multi-product. How to assess and prioritize new product ideas. How to measure success when launching new products. The 12 questions Tara asks for better product reviews. Tactics for collecting and interpreting user feedback. Referenced: First Round Capital's Newsletter: https://review.firstround.com/newsletter The 'Wins Above Replacement' metaphor: https://en.as.com/mlb/wins-above-replacement-war-baseball-statistic-explained-n/ Zero to One by Peter Thiel & Blake Masters: https://www.amazon.com.au/Zero-One-Notes-Startups-Future/dp/0804139296 Companies Referenced: Atlassian: https://www.atlassian.com/ Cash App: https://cash.app/ Figma: https://www.figma.com/ First Round Capital: https://firstround.com/ Lattice: https://lattice.com/ Notion: https://www.notion.so/ Paypal: https://www.paypal.com/ Stripe: https://stripe.com/ Watershed: https://watershed.com/ People Referenced: Jack Dorsey: https://twitter.com/jack Patrick Collison: https://twitter.com/patrickc Shreyas Doshi: https://twitter.com/shreyas Where to find Tara Seshan: LinkedIn: https://www.linkedin.com/in/tarstarr/ Twitter: https://twitter.com/tarstarr Where to find Brett Berson: Twitter: https://twitter.com/brettberson?lang=en LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ In this episode, we cover: (0:00) Intro (3:55) How Stripe navigated the path from single to multi-product (6:00) How to allocate resources across a primary product and secondary bets (7:46) How to launch products using small teams (12:25) What makes a great early-stage product thinker (13:08) Key indicators for spotting early-stage product talent (16:33) A common fail-case when hiring for potential over experience (18:32) 5 interview questions to unearth hidden talent among product candidates (20:35) What Stripe got wrong when it first launched Billing (26:00) How Stripe adapted to new buyer profiles (28:50) Why new product teams should be treated like a startup within a company (30:35) The importance of “definite optimism” (31:44) How Watershed prioritizes new products in an early market (33:53) The methodical versus analytical approach to picking new products (40:08) Setting goals and evaluating new product bets (41:55) How Tara runs new-product reviews (42:10) “The Enterprise Rent-A-Car Story” and why it matters (43:56) The 12 questions Tara asks in product reviews (46:17) How to use product review questions pre-meeting (46:34) The rationale behind Tara’s 12 questions (48:13) How Tara re-focusses the questions when building products for net-new-customers (49:43) How to collect and leverage user feedback when building new products (51:58) Why product development must start with problem validation (53:52) Two people who had an outsized impact on how Tara thinks about product (54:50) Outro Thu, 22 Jun 2023 08:00:00 -0000 Lessons from Stripe on adding new products - Assessing ideas, structuring teams, and tactics for product reviews | Tara Seshan (Watershed, Stripe) full 97 First Round Tara Seshan is the Head of Product at Watershed, a climate platform that companies use to measure, report, and reduce their carbon emissions. Before joining Watershed, Tara was Head of Product at Stripe throughout the launch of Stripe Billing and Stripe Treasury. As a Thiel Fellow and experienced multi-product builder, Tara brings a wealth of experience with 0-1 SaaS products. Tara Seshan is the Head of Product at Watershed, a climate platform that companies use to measure, report, and reduce their carbon emissions. Before joining Watershed, Tara was Head of Product at Stripe throughout the launch of Stripe Billing and Stripe Treasury. As a Thiel Fellow and experienced multi-product builder, Tara brings a wealth of experience with 0-1 SaaS products. In today's episode, we discuss: The different types of multi-product strategies. Stories from Stripe’s multi-product success. How to allocate resources across new and existing products. How to structure teams for launching new products. The best personas for building new products and the hiring tactics for finding those people. Common challenges when going from single to multi-product. How to assess and prioritize new product ideas. How to measure success when launching new products. The 12 questions Tara asks for better product reviews. Tactics for collecting and interpreting user feedback. Referenced: First Round Capital's Newsletter: https://review.firstround.com/newsletter The 'Wins Above Replacement' metaphor: https://en.as.com/mlb/wins-above-replacement-war-baseball-statistic-explained-n/ Zero to One by Peter Thiel & Blake Masters: https://www.amazon.com.au/Zero-One-Notes-Startups-Future/dp/0804139296 Companies Referenced: Atlassian: https://www.atlassian.com/ Cash App: https://cash.app/ Figma: https://www.figma.com/ First Round Capital: https://firstround.com/ Lattice: https://lattice.com/ Notion: https://www.notion.so/ Paypal: https://www.paypal.com/ Stripe: https://stripe.com/ Watershed: https://watershed.com/ People Referenced: Jack Dorsey: https://twitter.com/jack Patrick Collison: https://twitter.com/patrickc Shreyas Doshi: https://twitter.com/shreyas Where to find Tara Seshan: LinkedIn: https://www.linkedin.com/in/tarstarr/ Twitter: https://twitter.com/tarstarr Where to find Brett Berson: Twitter: https://twitter.com/brettberson?lang=en LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ In this episode, we cover: (0:00) Intro (3:55) How Stripe navigated the path from single to multi-product (6:00) How to allocate resources across a primary product and secondary bets (7:46) How to launch products using small teams (12:25) What makes a great early-stage product thinker (13:08) Key indicators for spotting early-stage product talent (16:33) A common fail-case when hiring for potential over experience (18:32) 5 interview questions to unearth hidden talent among product candidates (20:35) What Stripe got wrong when it first launched Billing (26:00) How Stripe adapted to new buyer profiles (28:50) Why new product teams should be treated like a startup within a company (30:35) The importance of “definite optimism” (31:44) How Watershed prioritizes new products in an early market (33:53) The methodical versus analytical approach to picking new products (40:08) Setting goals and evaluating new product bets (41:55) How Tara runs new-product reviews (42:10) “The Enterprise Rent-A-Car Story” and why it matters (43:56) The 12 questions Tara asks in product reviews (46:17) How to use product review questions pre-meeting (46:34) The rationale behind Tara’s 12 questions (48:13) How Tara re-focusses the questions when building products for net-new-customers (49:43) How to collect and leverage user feedback when building new products (51:58) Why product development must start with problem validation (53:52) Two people who had an outsized impact on how Tara thinks about product (54:50) Outro Tara Seshan is the Head of Product at Watershed, a climate platform that companies use to measure, report, and reduce their carbon emissions. Before joining Watershed, Tara was Head of Product at Stripe throughout the launch of Stripe Billing and Stripe Treasury. As a Thiel Fellow and experienced multi-product builder, Tara brings a wealth of experience with 0-1 SaaS products.


In today's episode, we discuss:

  • The different types of multi-product strategies.
  • Stories from Stripe’s multi-product success.
  • How to allocate resources across new and existing products.
  • How to structure teams for launching new products.
  • The best personas for building new products and the hiring tactics for finding those people.
  • Common challenges when going from single to multi-product.
  • How to assess and prioritize new product ideas.
  • How to measure success when launching new products.
  • The 12 questions Tara asks for better product reviews.
  • Tactics for collecting and interpreting user feedback.



Referenced:



Companies Referenced:



People Referenced:



Where to find Tara Seshan:

LinkedIn: https://www.linkedin.com/in/tarstarr/

Twitter: https://twitter.com/tarstarr



Where to find Brett Berson:

Twitter: https://twitter.com/brettberson?lang=en

LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/



In this episode, we cover:

(0:00) Intro

(3:55) How Stripe navigated the path from single to multi-product

(6:00) How to allocate resources across a primary product and secondary bets

(7:46) How to launch products using small teams

(12:25) What makes a great early-stage product thinker

(13:08) Key indicators for spotting early-stage product talent

(16:33) A common fail-case when hiring for potential over experience

(18:32) 5 interview questions to unearth hidden talent among product candidates

(20:35) What Stripe got wrong when it first launched Billing

(26:00) How Stripe adapted to new buyer profiles

(28:50) Why new product teams should be treated like a startup within a company

(30:35) The importance of “definite optimism”

(31:44) How Watershed prioritizes new products in an early market

(33:53) The methodical versus analytical approach to picking new products

(40:08) Setting goals and evaluating new product bets

(41:55) How Tara runs new-product reviews

(42:10) “The Enterprise Rent-A-Car Story” and why it matters

(43:56) The 12 questions Tara asks in product reviews

(46:17) How to use product review questions pre-meeting

(46:34) The rationale behind Tara’s 12 questions

(48:13) How Tara re-focusses the questions when building products for net-new-customers

(49:43) How to collect and leverage user feedback when building new products

(51:58) Why product development must start with problem validation

(53:52) Two people who had an outsized impact on how Tara thinks about product

(54:50) Outro

]]> 3337 no How to design a high-impact growth org for a PLG startup — Webflow & Dropbox’s Melissa Tan Our guest today is Melissa Tan, GM of Self-Service and Head of Growth at Webflow and formerly Head of Growth and Monetization for Dropbox Business. In today’s conversation, she unpacks the nuances between the two PLG businesses and how growth strategy changes for a more complex product like Webflow, including:  Designing and structuring a growth org The right way to tackle goal-setting How Webflow’s pricing and packaging has evolved How to calibrate pricing feedback You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.   Thu, 08 Jun 2023 08:00:00 -0000 full 91 First Round Melissa Tan is the GM of Self-Service and Head of Growth at Webflow and formerly the Head of Growth and Monetization for Dropbox Business. She unpacks the nuances between the two PLG businesses, including the growth strategy, approach to pricing and packaging, and goal setting techniques. Our guest today is Melissa Tan, GM of Self-Service and Head of Growth at Webflow and formerly Head of Growth and Monetization for Dropbox Business. In today’s conversation, she unpacks the nuances between the two PLG businesses and how growth strategy changes for a more complex product like Webflow, including:  Designing and structuring a growth org The right way to tackle goal-setting How Webflow’s pricing and packaging has evolved How to calibrate pricing feedback You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.   Our guest today is Melissa Tan, GM of Self-Service and Head of Growth at Webflow and formerly Head of Growth and Monetization for Dropbox Business.


In today’s conversation, she unpacks the nuances between the two PLG businesses and how growth strategy changes for a more complex product like Webflow, including: 


  • Designing and structuring a growth org
  • The right way to tackle goal-setting
  • How Webflow’s pricing and packaging has evolved
  • How to calibrate pricing feedback


You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  

]]> 3580 Why is the transition from IC Engineer to Manager so tricky (and how to get it right)? — Marcel Weekes, VP of Product Engineering at Figma Our guest today is Marcel Weekes, VP of Product Engineering at Figma and former VP of Engineering at Slack. In today’s conversation, he unpacks why most startups get it wrong when they uplevel someone from IC engineer to eng manager and unfurls what stellar engineering management looks like at high-growth companies, including: Setting appropriate expectations and goals  Turbocharging the team’s effectiveness  Delivering high-impact feedback Going from a peer to a manager What leaders risk when they drag their heels on managing out low-performers You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.   Thu, 25 May 2023 08:00:00 -0000 full 95 First Round Marcel Weekes is the VP of Product Engineering at Figma, and was formerly VP of Engineering at Slack. He unpacks why most startups get it wrong when they uplevel someone from IC engineer to eng manager and unfurls what stellar engineering management looks like at high-growth companies. Our guest today is Marcel Weekes, VP of Product Engineering at Figma and former VP of Engineering at Slack. In today’s conversation, he unpacks why most startups get it wrong when they uplevel someone from IC engineer to eng manager and unfurls what stellar engineering management looks like at high-growth companies, including: Setting appropriate expectations and goals  Turbocharging the team’s effectiveness  Delivering high-impact feedback Going from a peer to a manager What leaders risk when they drag their heels on managing out low-performers You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.   Our guest today is Marcel Weekes, VP of Product Engineering at Figma and former VP of Engineering at Slack.


In today’s conversation, he unpacks why most startups get it wrong when they uplevel someone from IC engineer to eng manager and unfurls what stellar engineering management looks like at high-growth companies, including:


  • Setting appropriate expectations and goals 
  • Turbocharging the team’s effectiveness 
  • Delivering high-impact feedback
  • Going from a peer to a manager
  • What leaders risk when they drag their heels on managing out low-performers


You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  

]]> 3606 How to pull off the ‘zoom-in pivot,’ and other lessons in early-stage building with Luminai’s Kesava Kirupa Dinakaran Todd Jackson is back on the mic to guest host another product-focused episode. This time, he chats with Kesava Kirupa Dinakaran, co-founder and CEO of Luminai, a B2B software tool that helps automate any manual process down to just one click.  Dinakaran’s personal and professional story is one that you do not want to miss. A former Rubik’s Cube champion and back-to-back Hackathon winner, Dinakaran’s foray into the world of building software products is anything but conventional. The founders stumbled on the idea for its automated “one-click” product started on accident, at a corporate hackathon.  But it’s exactly this unique worldview and introspective strategies that make Dinakaran’s advice on the path to finding product-market fit for Luminai so fascinating. Formerly called Digital Brain, Luminai is a Series A startup that’s raised nearly $20 million since its launch out of Y Combinator in 2020.  In this episode, we explore the psychology behind the sales process, why sales leaders should consider pitching straight to the CEO and Dinakaran’s decision to scrap hundreds of lines of written code to focus on building out their most beloved customer feature.  On the surface, Luminai may seem like just another B2B SaaS startup, but with nearly half the team comprising of former founders (seven of which are ex-YC founders), Luminai is a true example of how the co-founders can really make their mark on shaping their company on the path to product-market fit.   Thu, 18 May 2023 08:00:00 -0000 full 94 First Round Kesava Kirupa Dinakaran is the co-founder and CEO of Luminai, an early-stage software startup that automates workflows by taking any multi-click process and making it one click. Formerly a world-renowned Rubik’s Cube champion and a back-to-back corporate Hackathon winner, Dinakaran shares nuggets of wisdom from his personal journey to tech and Luminai’s path to finding product-market fit for other founders. Todd Jackson is back on the mic to guest host another product-focused episode. This time, he chats with Kesava Kirupa Dinakaran, co-founder and CEO of Luminai, a B2B software tool that helps automate any manual process down to just one click.  Dinakaran’s personal and professional story is one that you do not want to miss. A former Rubik’s Cube champion and back-to-back Hackathon winner, Dinakaran’s foray into the world of building software products is anything but conventional. The founders stumbled on the idea for its automated “one-click” product started on accident, at a corporate hackathon.  But it’s exactly this unique worldview and introspective strategies that make Dinakaran’s advice on the path to finding product-market fit for Luminai so fascinating. Formerly called Digital Brain, Luminai is a Series A startup that’s raised nearly $20 million since its launch out of Y Combinator in 2020.  In this episode, we explore the psychology behind the sales process, why sales leaders should consider pitching straight to the CEO and Dinakaran’s decision to scrap hundreds of lines of written code to focus on building out their most beloved customer feature.  On the surface, Luminai may seem like just another B2B SaaS startup, but with nearly half the team comprising of former founders (seven of which are ex-YC founders), Luminai is a true example of how the co-founders can really make their mark on shaping their company on the path to product-market fit.   Todd Jackson is back on the mic to guest host another product-focused episode. This time, he chats with Kesava Kirupa Dinakaran, co-founder and CEO of Luminai, a B2B software tool that helps automate any manual process down to just one click. 


Dinakaran’s personal and professional story is one that you do not want to miss. A former Rubik’s Cube champion and back-to-back Hackathon winner, Dinakaran’s foray into the world of building software products is anything but conventional. The founders stumbled on the idea for its automated “one-click” product started on accident, at a corporate hackathon. 


But it’s exactly this unique worldview and introspective strategies that make Dinakaran’s advice on the path to finding product-market fit for Luminai so fascinating. Formerly called Digital Brain, Luminai is a Series A startup that’s raised nearly $20 million since its launch out of Y Combinator in 2020. 


In this episode, we explore the psychology behind the sales process, why sales leaders should consider pitching straight to the CEO and Dinakaran’s decision to scrap hundreds of lines of written code to focus on building out their most beloved customer feature. 



On the surface, Luminai may seem like just another B2B SaaS startup, but with nearly half the team comprising of former founders (seven of which are ex-YC founders), Luminai is a true example of how the co-founders can really make their mark on shaping their company on the path to product-market fit.  

]]> 3517 The go-to-market guide for open-source companies — Douglas Hanna, COO Grafana Labs Our guest today is Douglas Hanna, Chief Operating Officer at Grafana Labs.  Grafana Labs is an observability stack built around Grafana, a leading open-source technology for dashboards and visualization. Douglas is a seasoned revenue leader, previously leading operations and GTM strategy at Zendesk. At Grafana Labs, Douglas has been instrumental in scaling GTM at the open-source company — building up both team headcount and its revenue model.  In our conversation today, Douglas dives deep into the process of bringing products to market at an open-source company. We explore the different facets of building and scaling a revenue model at an open-source company. Douglas opens up the GTM playbook at Grafana Labs sharing:  When to commercialize a feature vs. switch to a hosted version of a product Tried and tested frameworks for pricing and packaging  How Grafana Labs thinks about what to put behind a paywall  How the GTM team was built over time.,  You can follow Douglas on Twitter at @douglashanna. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Thu, 11 May 2023 08:00:00 -0000 full 93 First Round Douglas Hanna, Chief Operating Officer at Grafana Labs, explores the nuances of building and scaling revenue at an open-source company. Our guest today is Douglas Hanna, Chief Operating Officer at Grafana Labs.  Grafana Labs is an observability stack built around Grafana, a leading open-source technology for dashboards and visualization. Douglas is a seasoned revenue leader, previously leading operations and GTM strategy at Zendesk. At Grafana Labs, Douglas has been instrumental in scaling GTM at the open-source company — building up both team headcount and its revenue model.  In our conversation today, Douglas dives deep into the process of bringing products to market at an open-source company. We explore the different facets of building and scaling a revenue model at an open-source company. Douglas opens up the GTM playbook at Grafana Labs sharing:  When to commercialize a feature vs. switch to a hosted version of a product Tried and tested frameworks for pricing and packaging  How Grafana Labs thinks about what to put behind a paywall  How the GTM team was built over time.,  You can follow Douglas on Twitter at @douglashanna. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Our guest today is Douglas Hanna, Chief Operating Officer at Grafana Labs. 


Grafana Labs is an observability stack built around Grafana, a leading open-source technology for dashboards and visualization. Douglas is a seasoned revenue leader, previously leading operations and GTM strategy at Zendesk. At Grafana Labs, Douglas has been instrumental in scaling GTM at the open-source company — building up both team headcount and its revenue model. 


In our conversation today, Douglas dives deep into the process of bringing products to market at an open-source company.


We explore the different facets of building and scaling a revenue model at an open-source company. Douglas opens up the GTM playbook at Grafana Labs sharing: 

  • When to commercialize a feature vs. switch to a hosted version of a product
  • Tried and tested frameworks for pricing and packaging 
  • How Grafana Labs thinks about what to put behind a paywall 
  • How the GTM team was built over time., 

You can follow Douglas on Twitter at @douglashanna. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

]]> 3914 What this 3-time founding team did differently to find product-market fit faster — Jessica McKellar, CTO of Pilot Today’s conversation is with Jessica McKellar, co-founder and CTO of Pilot, which is the largest accounting firm for startups. She’s been working on Pilot for the last 6 years with her two co-founders, Waseem Daher and Jeff Arnold. But what makes this founding trio super unique is that they’ve stuck together in not just one, but three different startups.  As repeat founders, the Pilot team has learned a ton from their first two ventures, K Splice and Zulip, and both netted some positive outcomes. But as Jessica will share today, there were mistakes the team made along the way that prevented both products from becoming an outsized success.  So she unpacks what they did differently with Pilot — particularly when it came to picking an acute problem and a huge market to tackle. Jessica also shares the tedious process for building the early version of the product, which included looking over Waseem and Jeff’s shoulders as they manually did the bookkeeping for early customers, while she wrote code alongside them.  Even going back to the earliest days, Pilot had some really strong product-market fit signals, with customers agreeing to pull out their credit card and pay for the product right away when it was just an idea on paper and eventually pulling the Pilot team into expanding their product suite. Make no mistake about it — being a founder is incredibly difficult — but choosing the right problem to tackle can drastically smooth the path ahead of you.  Thu, 04 May 2023 08:00:00 -0000 full 92 First Round Jessica McKellar is the co-founder and CTO of Pilot, the largest accounting firm for startups. She’s also a three-time founder, all working with the same group of co-founders. McKellar shares the most valuable lessons the founding team has learned about smoothing your path to product-market fit by choosing the right market. Today’s conversation is with Jessica McKellar, co-founder and CTO of Pilot, which is the largest accounting firm for startups. She’s been working on Pilot for the last 6 years with her two co-founders, Waseem Daher and Jeff Arnold. But what makes this founding trio super unique is that they’ve stuck together in not just one, but three different startups.  As repeat founders, the Pilot team has learned a ton from their first two ventures, K Splice and Zulip, and both netted some positive outcomes. But as Jessica will share today, there were mistakes the team made along the way that prevented both products from becoming an outsized success.  So she unpacks what they did differently with Pilot — particularly when it came to picking an acute problem and a huge market to tackle. Jessica also shares the tedious process for building the early version of the product, which included looking over Waseem and Jeff’s shoulders as they manually did the bookkeeping for early customers, while she wrote code alongside them.  Even going back to the earliest days, Pilot had some really strong product-market fit signals, with customers agreeing to pull out their credit card and pay for the product right away when it was just an idea on paper and eventually pulling the Pilot team into expanding their product suite. Make no mistake about it — being a founder is incredibly difficult — but choosing the right problem to tackle can drastically smooth the path ahead of you.  Today’s conversation is with Jessica McKellar, co-founder and CTO of Pilot, which is the largest accounting firm for startups. She’s been working on Pilot for the last 6 years with her two co-founders, Waseem Daher and Jeff Arnold. But what makes this founding trio super unique is that they’ve stuck together in not just one, but three different startups. 


As repeat founders, the Pilot team has learned a ton from their first two ventures, K Splice and Zulip, and both netted some positive outcomes. But as Jessica will share today, there were mistakes the team made along the way that prevented both products from becoming an outsized success. 


So she unpacks what they did differently with Pilot — particularly when it came to picking an acute problem and a huge market to tackle. Jessica also shares the tedious process for building the early version of the product, which included looking over Waseem and Jeff’s shoulders as they manually did the bookkeeping for early customers, while she wrote code alongside them. 


Even going back to the earliest days, Pilot had some really strong product-market fit signals, with customers agreeing to pull out their credit card and pay for the product right away when it was just an idea on paper and eventually pulling the Pilot team into expanding their product suite. Make no mistake about it — being a founder is incredibly difficult — but choosing the right problem to tackle can drastically smooth the path ahead of you. 

]]> 3343 How to measure product-market fit with the REV model — Artem Kroupenev Our guest today is Artem Kroupenev, VP of Strategy at Augury.  Augury is a leader in a category they helped to define known as “machine health.” The company sells products that combine hardware, AI, and SaaS within industrial manufacturing.  Artem joined the team at the very beginning of its journey and helped shape strategies for how the team measured product-market fit, go-to-market, and eventually, a strategy for designing a brand new market category they could compete in.  In our conversation today, we dive deep into measurable product-market fit and category-creation strategies. Artem shares particular wisdom on: Augury’s storyboard-based approach to product vision  How to sell to a limited pool of customers  The REV (revenue, engagement and value) model from measuring product-market fit  When founders should start exploring creating a new category to operate in You can follow Artem on Twitter at @artemkroupenev You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Thu, 27 Apr 2023 08:00:00 -0000 full 91 First Round Artem Kroupenev, VP of Strategy at Augury, shares by-the-book frameworks for how his company measures product-market fit in the complex field of industrial equipment. Our guest today is Artem Kroupenev, VP of Strategy at Augury.  Augury is a leader in a category they helped to define known as “machine health.” The company sells products that combine hardware, AI, and SaaS within industrial manufacturing.  Artem joined the team at the very beginning of its journey and helped shape strategies for how the team measured product-market fit, go-to-market, and eventually, a strategy for designing a brand new market category they could compete in.  In our conversation today, we dive deep into measurable product-market fit and category-creation strategies. Artem shares particular wisdom on: Augury’s storyboard-based approach to product vision  How to sell to a limited pool of customers  The REV (revenue, engagement and value) model from measuring product-market fit  When founders should start exploring creating a new category to operate in You can follow Artem on Twitter at @artemkroupenev You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Our guest today is Artem Kroupenev, VP of Strategy at Augury. 

Augury is a leader in a category they helped to define known as “machine health.” The company sells products that combine hardware, AI, and SaaS within industrial manufacturing. 

Artem joined the team at the very beginning of its journey and helped shape strategies for how the team measured product-market fit, go-to-market, and eventually, a strategy for designing a brand new market category they could compete in. 

In our conversation today, we dive deep into measurable product-market fit and category-creation strategies. Artem shares particular wisdom on:

  • Augury’s storyboard-based approach to product vision 
  • How to sell to a limited pool of customers 
  • The REV (revenue, engagement and value) model from measuring product-market fit 
  • When founders should start exploring creating a new category to operate in


You can follow Artem on Twitter at @artemkroupenev You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

]]> 3314 The early user research playbook for founders — Jeanette Mellinger’s expert advice for validating your idea with high-quality interviews Our guest today is Jeanette Mellinger, Head of UX Research at BetterUp and our User Research Expert in Residence at First Round. In today’s conversation, Jeanette unspools her tested playbook for high-quality customer interviews, with particular advice for founders in the very early days of validating an idea, including:  The three-step framework for a thorough user-research process The biggest mistakes she’s noticed after working with dozens of early-stage companies  Specific advice for structuring an interview flow and crafting better questions that unlock essential insights You can follow Jeanette on Twitter at @jnetmell  You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Thu, 20 Apr 2023 08:00:00 -0000 full 88 First Round User research expert Jeanette Mellinger shares her three-step process to high-quality user research, with tailored advice for founders in the early days of validating a startup idea. Our guest today is Jeanette Mellinger, Head of UX Research at BetterUp and our User Research Expert in Residence at First Round. In today’s conversation, Jeanette unspools her tested playbook for high-quality customer interviews, with particular advice for founders in the very early days of validating an idea, including:  The three-step framework for a thorough user-research process The biggest mistakes she’s noticed after working with dozens of early-stage companies  Specific advice for structuring an interview flow and crafting better questions that unlock essential insights You can follow Jeanette on Twitter at @jnetmell  You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Our guest today is Jeanette Mellinger, Head of UX Research at BetterUp and our User Research Expert in Residence at First Round.


In today’s conversation, Jeanette unspools her tested playbook for high-quality customer interviews, with particular advice for founders in the very early days of validating an idea, including: 

  • The three-step framework for a thorough user-research process
  • The biggest mistakes she’s noticed after working with dozens of early-stage companies 
  • Specific advice for structuring an interview flow and crafting better questions that unlock essential insights

You can follow Jeanette on Twitter at @jnetmell 


You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

]]> 4285 Claire Hughes Johnson on being a “learning organism” during Stripe’s growth, and more scaling advice for leaders Our guest today is Claire Hughes Johnson, former COO of Stripe and author of the new book, “Scaling People: Tactics for Management and Company Building.”  Claire joined Stripe as its COO back in 2014 and, over the course of her nearly seven years in the company’s executive suite, she oversaw rapid growth as Stripe scaled from under 200 employees to over 7,000. Prior to Stripe, she spent 10 years at Google leading various high-impact business teams.  In today’s conversation, In today’s conversation, Claire takes us behind the scenes at some of the most pivotal moments in her life that turned her into the type of leader she is today, including: The inside story of her lengthy, no-stone-unturned process of interviewing with the Collison brothers for the COO seat.  How she applied some of those same lessons for hiring exceptional talent, including the right way to do reference checks and her own theories on why it’s so hard to get executive hiring right.    How her parents instilled her deep curiosity and fierce independence at a very young age.  Why she believes all high-performers are “learning organisms.”  You can follow Claire on Twitter at @chughesjohnson. Check out her new book, “Scaling People,” as well as the book she recommended from Fred Kofman titled “Conscious Business.” You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Thu, 13 Apr 2023 08:00:00 -0000 full 89 First Round Claire Hughes Johnson spent seven years as the COO of Stripe, overseeing rapid growth as the company scaled from under 200 employees to over 7,000. She takes us behind the scenes at some of the most pivotal moments in her own life and career that catapulted her into the deeply curious leader she is today. Our guest today is Claire Hughes Johnson, former COO of Stripe and author of the new book, “Scaling People: Tactics for Management and Company Building.”  Claire joined Stripe as its COO back in 2014 and, over the course of her nearly seven years in the company’s executive suite, she oversaw rapid growth as Stripe scaled from under 200 employees to over 7,000. Prior to Stripe, she spent 10 years at Google leading various high-impact business teams.  In today’s conversation, In today’s conversation, Claire takes us behind the scenes at some of the most pivotal moments in her life that turned her into the type of leader she is today, including: The inside story of her lengthy, no-stone-unturned process of interviewing with the Collison brothers for the COO seat.  How she applied some of those same lessons for hiring exceptional talent, including the right way to do reference checks and her own theories on why it’s so hard to get executive hiring right.    How her parents instilled her deep curiosity and fierce independence at a very young age.  Why she believes all high-performers are “learning organisms.”  You can follow Claire on Twitter at @chughesjohnson. Check out her new book, “Scaling People,” as well as the book she recommended from Fred Kofman titled “Conscious Business.” You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Our guest today is Claire Hughes Johnson, former COO of Stripe and author of the new book, “Scaling People: Tactics for Management and Company Building.” 


Claire joined Stripe as its COO back in 2014 and, over the course of her nearly seven years in the company’s executive suite, she oversaw rapid growth as Stripe scaled from under 200 employees to over 7,000. Prior to Stripe, she spent 10 years at Google leading various high-impact business teams. 


In today’s conversation, In today’s conversation, Claire takes us behind the scenes at some of the most pivotal moments in her life that turned her into the type of leader she is today, including:

  • The inside story of her lengthy, no-stone-unturned process of interviewing with the Collison brothers for the COO seat. 
  • How she applied some of those same lessons for hiring exceptional talent, including the right way to do reference checks and her own theories on why it’s so hard to get executive hiring right.   
  • How her parents instilled her deep curiosity and fierce independence at a very young age. 
  • Why she believes all high-performers are “learning organisms.” 

You can follow Claire on Twitter at @chughesjohnson. Check out her new book, “Scaling People,” as well as the book she recommended from Fred Kofman titled “Conscious Business.”


You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

]]> 4545 Notion’s Head of Marketing on building a growth marketing engine at a PLG company — Rachel Hepworth Our guest today is Rachel Hepworth, Head of Marketing at Notion.  Rachel currently runs growth marketing at Notion, and sees her job as bringing process and control to all of Notion’s different marketing channels. Before joining Notion, Rachel launched the first growth marketing team at Slack, laying down the tracks for a well-oiled go-to-market strategy that could be measured easily.  Much like Slack, Notion has made a name for itself largely through customer love and a powerful word-of-mouth recommendation engine. As a metrics-focused marketer, Rachel opens up her playbook on how she lassos that kind of word-of-mouth growth and the analytical approach she has toward acquiring and retaining customers.  In our conversation today, we focus on the nuts and bolts of what growth marketing looks like inside an organization that’s driven by product-led growth. Rachel shares tactical advice on: Why high-speed feedback cycles are so important  Early indicators of which sign-ups are most likely to convert to paid customers Her process for adjusting which top-of-funnel metrics to track over time  How marketing, product and sales all work together at Notion to own a different part of the customer funnel You can follow Rachel on Twitter at @rachelhepworth. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Thu, 06 Apr 2023 08:00:00 -0000 full 86 First Round Rachel Hepworth, Head of Marketing at Notion and formerly Slack’s first growth marketing hire, shares her high-level frameworks for bringing marketing process and analytical structure to PLG companies. Our guest today is Rachel Hepworth, Head of Marketing at Notion.  Rachel currently runs growth marketing at Notion, and sees her job as bringing process and control to all of Notion’s different marketing channels. Before joining Notion, Rachel launched the first growth marketing team at Slack, laying down the tracks for a well-oiled go-to-market strategy that could be measured easily.  Much like Slack, Notion has made a name for itself largely through customer love and a powerful word-of-mouth recommendation engine. As a metrics-focused marketer, Rachel opens up her playbook on how she lassos that kind of word-of-mouth growth and the analytical approach she has toward acquiring and retaining customers.  In our conversation today, we focus on the nuts and bolts of what growth marketing looks like inside an organization that’s driven by product-led growth. Rachel shares tactical advice on: Why high-speed feedback cycles are so important  Early indicators of which sign-ups are most likely to convert to paid customers Her process for adjusting which top-of-funnel metrics to track over time  How marketing, product and sales all work together at Notion to own a different part of the customer funnel You can follow Rachel on Twitter at @rachelhepworth. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Our guest today is Rachel Hepworth, Head of Marketing at Notion. 

Rachel currently runs growth marketing at Notion, and sees her job as bringing process and control to all of Notion’s different marketing channels. Before joining Notion, Rachel launched the first growth marketing team at Slack, laying down the tracks for a well-oiled go-to-market strategy that could be measured easily. 

Much like Slack, Notion has made a name for itself largely through customer love and a powerful word-of-mouth recommendation engine. As a metrics-focused marketer, Rachel opens up her playbook on how she lassos that kind of word-of-mouth growth and the analytical approach she has toward acquiring and retaining customers. 

In our conversation today, we focus on the nuts and bolts of what growth marketing looks like inside an organization that’s driven by product-led growth. Rachel shares tactical advice on:

  • Why high-speed feedback cycles are so important 
  • Early indicators of which sign-ups are most likely to convert to paid customers
  • Her process for adjusting which top-of-funnel metrics to track over time 
  • How marketing, product and sales all work together at Notion to own a different part of the customer funnel


You can follow Rachel on Twitter at @rachelhepworth. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

]]> 3212 What makes someone a truly remarkable talent evaluator — Nadia Singer, Figma’s Chief People Officer Our guest today is Nadia Singer, Chief People Officer at Figma.  Nadia joined Figma in 2020 and has seen explosive growth in her own career alongside the collaborative design platform’s. Before Figma, Singer was a talent expert who has hired hundreds of talented folks at places like Quora, Facebook and Google.  In our conversation today, we dive deep into what makes someone a terrific talent evaluator. Nadia opens up her own recruiter playbook and shares: Her personal recruiting trick, which is to study how a candidate reaches an answer, rather than what they say Tactics interviewers can use to avoid pattern matching and other biases The biggest mistakes she made in her early days as a recruiter  Ways that Figma tweaked its approach to culture so it could scale alongside the company  You can follow Nadia on Twitter at @nadsinger. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Thu, 30 Mar 2023 08:00:00 -0000 full 87 First Round Nadia Singer, Chief People Officer at Figma, shares why she believes anyone can become a skilled talent evaluator, her best interview questions and how Figma leverages transparency across the org. Our guest today is Nadia Singer, Chief People Officer at Figma.  Nadia joined Figma in 2020 and has seen explosive growth in her own career alongside the collaborative design platform’s. Before Figma, Singer was a talent expert who has hired hundreds of talented folks at places like Quora, Facebook and Google.  In our conversation today, we dive deep into what makes someone a terrific talent evaluator. Nadia opens up her own recruiter playbook and shares: Her personal recruiting trick, which is to study how a candidate reaches an answer, rather than what they say Tactics interviewers can use to avoid pattern matching and other biases The biggest mistakes she made in her early days as a recruiter  Ways that Figma tweaked its approach to culture so it could scale alongside the company  You can follow Nadia on Twitter at @nadsinger. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Our guest today is Nadia Singer, Chief People Officer at Figma. 

Nadia joined Figma in 2020 and has seen explosive growth in her own career alongside the collaborative design platform’s. Before Figma, Singer was a talent expert who has hired hundreds of talented folks at places like Quora, Facebook and Google. 

In our conversation today, we dive deep into what makes someone a terrific talent evaluator. Nadia opens up her own recruiter playbook and shares:

  • Her personal recruiting trick, which is to study how a candidate reaches an answer, rather than what they say
  • Tactics interviewers can use to avoid pattern matching and other biases
  • The biggest mistakes she made in her early days as a recruiter 
  • Ways that Figma tweaked its approach to culture so it could scale alongside the company 

You can follow Nadia on Twitter at @nadsinger. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

]]> 2967 How Vanta’s founder bet big on startup security and found product-market fit — Christina Cacioppo Todd Jackson is back on the mic to guest host another product-focused episode this week with Christina Cacioppo, the co-founder and CEO of Vanta.  Vanta is the leading automated security and compliance platform, with thousands of businesses relying on the product to get compliant (and to stay that way).   After toying with some initial ideas, like a voice assistant for biologists, Christina started building Vanta to solve a problem that didn’t really exist at the time. The company started out in 2018 by trying to get SOC-2 security compliance for startups — but at the time, startups didn’t even really need to have SOC-2s.  But Christina and her team saw the writing on the wall and that security was going to shoot up on the priority list for even the earliest-stage companies, and kept building even when plenty of smart people told them it was a bad idea. It’s a gamble that paid off. After going through Y Combinator, the team nabbed some truly incredible early customers, including Segment, Front and Lattice. Christina tells us exactly how she went from zero selling experience to pulling off big-time deals.  She also pulls back the curtain on some of Vanta’s more unconventional moves, like waiting until they acquired hundreds of customers to build a proper website and instead relying almost exclusively on word-of-mouth to grow the business. Christina also shares her thinking behind the fundraising strategy, in which Vanta operated at cash flow break-even for years before going out to raise its Series A.  Thu, 23 Mar 2023 08:00:00 -0000 full 86 First Round Christina Cacioppo is the co-founder and CEO of Vanta. She pulls back the curtain on some of the security company’s more unconventional moves on the path to product-market fit, like waiting until they acquired hundreds of customers before building a website and operating at cash flow break-even for years before raising its Series A. Todd Jackson is back on the mic to guest host another product-focused episode this week with Christina Cacioppo, the co-founder and CEO of Vanta.  Vanta is the leading automated security and compliance platform, with thousands of businesses relying on the product to get compliant (and to stay that way).   After toying with some initial ideas, like a voice assistant for biologists, Christina started building Vanta to solve a problem that didn’t really exist at the time. The company started out in 2018 by trying to get SOC-2 security compliance for startups — but at the time, startups didn’t even really need to have SOC-2s.  But Christina and her team saw the writing on the wall and that security was going to shoot up on the priority list for even the earliest-stage companies, and kept building even when plenty of smart people told them it was a bad idea. It’s a gamble that paid off. After going through Y Combinator, the team nabbed some truly incredible early customers, including Segment, Front and Lattice. Christina tells us exactly how she went from zero selling experience to pulling off big-time deals.  She also pulls back the curtain on some of Vanta’s more unconventional moves, like waiting until they acquired hundreds of customers to build a proper website and instead relying almost exclusively on word-of-mouth to grow the business. Christina also shares her thinking behind the fundraising strategy, in which Vanta operated at cash flow break-even for years before going out to raise its Series A.  Todd Jackson is back on the mic to guest host another product-focused episode this week with Christina Cacioppo, the co-founder and CEO of Vanta. 


Vanta is the leading automated security and compliance platform, with thousands of businesses relying on the product to get compliant (and to stay that way).  


After toying with some initial ideas, like a voice assistant for biologists, Christina started building Vanta to solve a problem that didn’t really exist at the time. The company started out in 2018 by trying to get SOC-2 security compliance for startups — but at the time, startups didn’t even really need to have SOC-2s. 


But Christina and her team saw the writing on the wall and that security was going to shoot up on the priority list for even the earliest-stage companies, and kept building even when plenty of smart people told them it was a bad idea.


It’s a gamble that paid off. After going through Y Combinator, the team nabbed some truly incredible early customers, including Segment, Front and Lattice. Christina tells us exactly how she went from zero selling experience to pulling off big-time deals. 


She also pulls back the curtain on some of Vanta’s more unconventional moves, like waiting until they acquired hundreds of customers to build a proper website and instead relying almost exclusively on word-of-mouth to grow the business. Christina also shares her thinking behind the fundraising strategy, in which Vanta operated at cash flow break-even for years before going out to raise its Series A. 

]]> 2841 Lessons from Notion on building a thriving decentralized community — Ben Lang Our guest today is Ben Lang, Head of Community at Notion.  Since joining the company in 2019, Ben has had his hand in several high-impact projects at Notion that has grown its tight-knit community of passionate Notion evangelists into millions of users today.  But before he was doing this as a full-time job, Ben was already spreading his love for Notion in his free time as a voracious product user. After discovering the tool on Product Hunt, he became obsessed. He got on the company’s radar after launching his own Notion template gallery on Product Hunt and joined as one of the first 15 employees.  In our conversation today, we focus on the nuts and bolts of building a global community that drives user growth. Ben shares tactical advice on: Tackling community organically from the bottom-up, and why you shouldn’t go top-down What companies are best suited to a centralized vs. decentralized community approach  Partnering with YouTubers and other creators  His advice to founders on finding your own first community hire You can follow Ben on Twitter at @benln. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Thu, 16 Mar 2023 08:00:00 -0000 full 85 First Round Ben Lang, Head of Community at Notion, shares his playbook for how to tap into your product evangelists and build a powerful community that grows from dozens to millions. Our guest today is Ben Lang, Head of Community at Notion.  Since joining the company in 2019, Ben has had his hand in several high-impact projects at Notion that has grown its tight-knit community of passionate Notion evangelists into millions of users today.  But before he was doing this as a full-time job, Ben was already spreading his love for Notion in his free time as a voracious product user. After discovering the tool on Product Hunt, he became obsessed. He got on the company’s radar after launching his own Notion template gallery on Product Hunt and joined as one of the first 15 employees.  In our conversation today, we focus on the nuts and bolts of building a global community that drives user growth. Ben shares tactical advice on: Tackling community organically from the bottom-up, and why you shouldn’t go top-down What companies are best suited to a centralized vs. decentralized community approach  Partnering with YouTubers and other creators  His advice to founders on finding your own first community hire You can follow Ben on Twitter at @benln. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Our guest today is Ben Lang, Head of Community at Notion. 


Since joining the company in 2019, Ben has had his hand in several high-impact projects at Notion that has grown its tight-knit community of passionate Notion evangelists into millions of users today. 


But before he was doing this as a full-time job, Ben was already spreading his love for Notion in his free time as a voracious product user. After discovering the tool on Product Hunt, he became obsessed. He got on the company’s radar after launching his own Notion template gallery on Product Hunt and joined as one of the first 15 employees. 

In our conversation today, we focus on the nuts and bolts of building a global community that drives user growth. Ben shares tactical advice on:

  • Tackling community organically from the bottom-up, and why you shouldn’t go top-down
  • What companies are best suited to a centralized vs. decentralized community approach 
  • Partnering with YouTubers and other creators 
  • His advice to founders on finding your own first community hire

You can follow Ben on Twitter at @benln. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

]]> 2667 From a narrow ICP to a wide-open market – Lessons from Webflow’s Bryant Chou on using customer empathy to get product-market fit Todd Jackson is back on the mic to guest host another product-focused episode this week. He chats with Bryant Chou, co-founder and founding CTO of Webflow, a no-code visual web design platform built with freelance designers and developers in mind.  Today, Webflow is valued at over $4 billion and has millions of users all over the world. More than 200,000 freelancers, agencies, small businesses and enterprises use Webflow to help design and power their websites at businesses large and small.  But Webflow didn’t always market to such a wide customer base. In our conversation today, Bryant rewinds the clock to Webflow’s early days — when it was just a co-founder team of three building a better tool to design a website.  We explore why the Webflow co-founding team had such a strong conviction that designers were their ICP, and why they took much longer to launch than other folks in their Y Combinator cohort. Bryant also explains how Webflow wrangled their viral launch on Hacker News into a sustainable revenue and shares his root cause analysis framework for collecting customer feedback.  On the surface, Webflow’s path to product-market fit seems incredibly smooth. But as Bryant tells it, there were plenty of bumps in the road — and he’s got tons of advice for early-stage founders that are finding their footing.  Thu, 09 Mar 2023 09:00:00 -0000 full 84 First Round Bryant Chou is the co-founder of Webflow. He goes back to the early days of ideating on and building Webflow, walking us through how the co-founders formed their hypothesis around Webflow’s ICP, its viral launch on Hacker News, keeping a startup afloat with dwindling capital and the lessons in customer empathy that stick with him. Todd Jackson is back on the mic to guest host another product-focused episode this week. He chats with Bryant Chou, co-founder and founding CTO of Webflow, a no-code visual web design platform built with freelance designers and developers in mind.  Today, Webflow is valued at over $4 billion and has millions of users all over the world. More than 200,000 freelancers, agencies, small businesses and enterprises use Webflow to help design and power their websites at businesses large and small.  But Webflow didn’t always market to such a wide customer base. In our conversation today, Bryant rewinds the clock to Webflow’s early days — when it was just a co-founder team of three building a better tool to design a website.  We explore why the Webflow co-founding team had such a strong conviction that designers were their ICP, and why they took much longer to launch than other folks in their Y Combinator cohort. Bryant also explains how Webflow wrangled their viral launch on Hacker News into a sustainable revenue and shares his root cause analysis framework for collecting customer feedback.  On the surface, Webflow’s path to product-market fit seems incredibly smooth. But as Bryant tells it, there were plenty of bumps in the road — and he’s got tons of advice for early-stage founders that are finding their footing.  Todd Jackson is back on the mic to guest host another product-focused episode this week. He chats with Bryant Chou, co-founder and founding CTO of Webflow, a no-code visual web design platform built with freelance designers and developers in mind. 


Today, Webflow is valued at over $4 billion and has millions of users all over the world. More than 200,000 freelancers, agencies, small businesses and enterprises use Webflow to help design and power their websites at businesses large and small. 


But Webflow didn’t always market to such a wide customer base. In our conversation today, Bryant rewinds the clock to Webflow’s early days — when it was just a co-founder team of three building a better tool to design a website. 


We explore why the Webflow co-founding team had such a strong conviction that designers were their ICP, and why they took much longer to launch than other folks in their Y Combinator cohort. Bryant also explains how Webflow wrangled their viral launch on Hacker News into a sustainable revenue and shares his root cause analysis framework for collecting customer feedback. 


On the surface, Webflow’s path to product-market fit seems incredibly smooth. But as Bryant tells it, there were plenty of bumps in the road — and he’s got tons of advice for early-stage founders that are finding their footing. 

]]> 3386 How to lead with transparency amidst adversity — Don Faul, CEO of CrossFit and former Google, Facebook & Pinterest exec Our guest today is Don Faul, CEO of CrossFit. Don has a fascinating background where he’s been able to find success in environments as different as a combat zone and a corporate board room. After spending 8 years as a platoon commander in the U.S. Marine Corps, Don had stints at some of the most vaunted companies in tech, including Google, Facebook and Pinterest, the latter of which he served as the Head of Operations. It’s a really unique set of leadership experiences spanning very different cultures.  In today’s conversation, he answers some burning questions like if micromanagement is always a bad thing, how to create a long-term company vision that genuinely gets people fired up about the future, and what folks tend to get wrong in their all-hands meetings.  We also discuss what it takes to lead in this current environment, and how leadership looks different when things feel like they’re going off the rails, which plenty of startup folks are feeling right now. Don unpacks his biggest lessons on how to embrace transparency when things aren’t going well, and candidly shares his own experience of having to wind down a company.  Read the article Don penned for First Round Review: The Pivotal Stories Every Startup Leader Should be Able to Tell. You can follow Don on Twitter @donfaul You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson  Thu, 23 Feb 2023 09:00:00 -0000 full 83 First Round Before taking over the helm of CrossFit as its new CEO, Don Faul’s leadership experience included an 8-year stint as a U.S. Marine Corps platoon commander and executive roles at Pinterest, Meta and Google. Here, he unpacks the leadership principles that have carried him through vastly different operating environments. Our guest today is Don Faul, CEO of CrossFit. Don has a fascinating background where he’s been able to find success in environments as different as a combat zone and a corporate board room. After spending 8 years as a platoon commander in the U.S. Marine Corps, Don had stints at some of the most vaunted companies in tech, including Google, Facebook and Pinterest, the latter of which he served as the Head of Operations. It’s a really unique set of leadership experiences spanning very different cultures.  In today’s conversation, he answers some burning questions like if micromanagement is always a bad thing, how to create a long-term company vision that genuinely gets people fired up about the future, and what folks tend to get wrong in their all-hands meetings.  We also discuss what it takes to lead in this current environment, and how leadership looks different when things feel like they’re going off the rails, which plenty of startup folks are feeling right now. Don unpacks his biggest lessons on how to embrace transparency when things aren’t going well, and candidly shares his own experience of having to wind down a company.  Read the article Don penned for First Round Review: The Pivotal Stories Every Startup Leader Should be Able to Tell. You can follow Don on Twitter @donfaul You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson  Our guest today is Don Faul, CEO of CrossFit.


Don has a fascinating background where he’s been able to find success in environments as different as a combat zone and a corporate board room. After spending 8 years as a platoon commander in the U.S. Marine Corps, Don had stints at some of the most vaunted companies in tech, including Google, Facebook and Pinterest, the latter of which he served as the Head of Operations. It’s a really unique set of leadership experiences spanning very different cultures. 


In today’s conversation, he answers some burning questions like if micromanagement is always a bad thing, how to create a long-term company vision that genuinely gets people fired up about the future, and what folks tend to get wrong in their all-hands meetings. 


We also discuss what it takes to lead in this current environment, and how leadership looks different when things feel like they’re going off the rails, which plenty of startup folks are feeling right now. Don unpacks his biggest lessons on how to embrace transparency when things aren’t going well, and candidly shares his own experience of having to wind down a company. 


Read the article Don penned for First Round Review: The Pivotal Stories Every Startup Leader Should be Able to Tell.


You can follow Don on Twitter @donfaul


You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

]]> 4204 From kickoffs to retros and Slack channels — Stripe's documentation best practices with Brie Wolfson Our guest today is Brie Wolfson.  Brie spent nearly 5 years at Stripe, where she worked on bizops and launched Stripe Press, followed by a stint at Figma where she worked on education. She then started her consultancy, named The Kool-Aid Factory, to share her lessons on building team cultures. And now she’s operating as a first-time founder building Constellate, a new productivity and communications tool for teams. In today’s conversation, we’re focused on company culture. A decade or so ago, companies like Google and Amazon dominated the cultural zeitgeist, with founders wanting to emulate their secret sauce. Today, there’s a newer guard of companies that startups want to model themselves after, with Stripe at the very top of the list.  Brie peels back the layers into not just the cultural pillars that drove Stripe’s meteoric rise, but also how these showed up in day-to-day work.  We also zoom out beyond Stripe to talk about her work teaming up with companies with The Kool-Aid Factory, seeing culture and company-building up close. Brie shares advice on codifying your operating principles, establishing meaningful rituals, and growing this kernel of culture as the company scales.  Read the full essay Brie recommended during the interview: Reality has a surprising amount of detail and the article she penned for First Round Review: Ditch Your To-Do List and Use These Docs to Make More Impact. You can follow Brie on Twitter @zebriez You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson  Thu, 09 Feb 2023 09:00:00 -0000 full 82 First Round Former Stripe and Figma leader and founder of The Kool-Aid Factory Brie Wolfson takes us behind the scenes at how company cultures evolve over time, from operating principles to documentation and rituals. Our guest today is Brie Wolfson.  Brie spent nearly 5 years at Stripe, where she worked on bizops and launched Stripe Press, followed by a stint at Figma where she worked on education. She then started her consultancy, named The Kool-Aid Factory, to share her lessons on building team cultures. And now she’s operating as a first-time founder building Constellate, a new productivity and communications tool for teams. In today’s conversation, we’re focused on company culture. A decade or so ago, companies like Google and Amazon dominated the cultural zeitgeist, with founders wanting to emulate their secret sauce. Today, there’s a newer guard of companies that startups want to model themselves after, with Stripe at the very top of the list.  Brie peels back the layers into not just the cultural pillars that drove Stripe’s meteoric rise, but also how these showed up in day-to-day work.  We also zoom out beyond Stripe to talk about her work teaming up with companies with The Kool-Aid Factory, seeing culture and company-building up close. Brie shares advice on codifying your operating principles, establishing meaningful rituals, and growing this kernel of culture as the company scales.  Read the full essay Brie recommended during the interview: Reality has a surprising amount of detail and the article she penned for First Round Review: Ditch Your To-Do List and Use These Docs to Make More Impact. You can follow Brie on Twitter @zebriez You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson  Our guest today is Brie Wolfson. 


Brie spent nearly 5 years at Stripe, where she worked on bizops and launched Stripe Press, followed by a stint at Figma where she worked on education. She then started her consultancy, named The Kool-Aid Factory, to share her lessons on building team cultures. And now she’s operating as a first-time founder building Constellate, a new productivity and communications tool for teams.


In today’s conversation, we’re focused on company culture. A decade or so ago, companies like Google and Amazon dominated the cultural zeitgeist, with founders wanting to emulate their secret sauce. Today, there’s a newer guard of companies that startups want to model themselves after, with Stripe at the very top of the list. 


Brie peels back the layers into not just the cultural pillars that drove Stripe’s meteoric rise, but also how these showed up in day-to-day work. 


We also zoom out beyond Stripe to talk about her work teaming up with companies with The Kool-Aid Factory, seeing culture and company-building up close. Brie shares advice on codifying your operating principles, establishing meaningful rituals, and growing this kernel of culture as the company scales. 


Read the full essay Brie recommended during the interview: Reality has a surprising amount of detail and the article she penned for First Round Review: Ditch Your To-Do List and Use These Docs to Make More Impact.


You can follow Brie on Twitter @zebriez


You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

]]> 3217 Why comms deserves its own spot on the exec team — Aaron Zamost’s lessons from Square https://review.firstround.com/podcast/episode-81 Our guest today is Aaron Zamost. After a comms career at Google, Aaron joined Square in 2011 to lead corporate communications. He went on to join the exec team, reporting directly to Jack Dorsey and leading the comms strategy for Square’s IPO in 2015. In an interesting move, he also took on leading the people organization as well, running both orgs up until he left in late 2020. In addition to lecturing at UC Berkeley's School of Law, Aaron now runs Background Partners, a communications consulting firm. In today’s conversation, we dive deep into what founders need to know about both external and internal comms. Aaron shares more on: Why comms deserves its own spot on the exec team and why most founders shouldn’t hire PR agencies. The jobs-to-be-done of the comms function in the early days of a startup — and why it’s not a good customer acquisition strategy. A 3-question framework for simplifying your company message early on. How to prep for interviews and deal with difficult lines of questioning. How to think about commenting on events in the news, or message layoffs to the team. Given how much the media landscape has changed in recent years, and how many founders are grappling with internal comms issues these days, Aaron’s advice makes for a valuable listen.  We also recommend checking out his two excellent Medium posts: -What’s Your Hour in ‘Silicon Valley Time’? No, you don’t need to hire an agency You can follow Aaron on Twitter at @zamosta. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Thu, 02 Feb 2023 09:00:00 -0000 full 81 First Round Former Square exec Aaron Zamost on why comms belongs on the leadership team, why you shouldn’t hire a PR agency, and how to handle internal comms. Our guest today is Aaron Zamost. After a comms career at Google, Aaron joined Square in 2011 to lead corporate communications. He went on to join the exec team, reporting directly to Jack Dorsey and leading the comms strategy for Square’s IPO in 2015. In an interesting move, he also took on leading the people organization as well, running both orgs up until he left in late 2020. In addition to lecturing at UC Berkeley's School of Law, Aaron now runs Background Partners, a communications consulting firm. In today’s conversation, we dive deep into what founders need to know about both external and internal comms. Aaron shares more on: Why comms deserves its own spot on the exec team and why most founders shouldn’t hire PR agencies. The jobs-to-be-done of the comms function in the early days of a startup — and why it’s not a good customer acquisition strategy. A 3-question framework for simplifying your company message early on. How to prep for interviews and deal with difficult lines of questioning. How to think about commenting on events in the news, or message layoffs to the team. Given how much the media landscape has changed in recent years, and how many founders are grappling with internal comms issues these days, Aaron’s advice makes for a valuable listen.  We also recommend checking out his two excellent Medium posts: -What’s Your Hour in ‘Silicon Valley Time’? No, you don’t need to hire an agency You can follow Aaron on Twitter at @zamosta. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Our guest today is Aaron Zamost.


After a comms career at Google, Aaron joined Square in 2011 to lead corporate communications. He went on to join the exec team, reporting directly to Jack Dorsey and leading the comms strategy for Square’s IPO in 2015. In an interesting move, he also took on leading the people organization as well, running both orgs up until he left in late 2020. In addition to lecturing at UC Berkeley's School of Law, Aaron now runs Background Partners, a communications consulting firm.


In today’s conversation, we dive deep into what founders need to know about both external and internal comms. Aaron shares more on:

  • Why comms deserves its own spot on the exec team and why most founders shouldn’t hire PR agencies.
  • The jobs-to-be-done of the comms function in the early days of a startup — and why it’s not a good customer acquisition strategy.
  • A 3-question framework for simplifying your company message early on.
  • How to prep for interviews and deal with difficult lines of questioning.
  • How to think about commenting on events in the news, or message layoffs to the team.

Given how much the media landscape has changed in recent years, and how many founders are grappling with internal comms issues these days, Aaron’s advice makes for a valuable listen. 


We also recommend checking out his two excellent Medium posts:

-What’s Your Hour in ‘Silicon Valley Time’?

No, you don’t need to hire an agency


You can follow Aaron on Twitter at @zamosta. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

]]> 3954 What founders need to know about acquisitions: Shopify’s Daniel Debow on M&A lessons from selling three startups https://review.firstround.com/podcast/episode-80 Our guest today is Daniel Debow, a VP of Product for Demand at Shopify.  Daniel is a three-time founder and a seasoned M&A pro. Daniel oversaw the process of all three of his companies’ acquisitions and has helped continue to grow them at scale inside larger corporations. His most recent startup, Helpful, was acquired by Shopify in 2019. Before that, he co-founded Rypple which was acquired by Salesforce in 2011. His first startup, Workbrain, was acquired by Infor in 2007.  In our conversation today, we focus on all the moving parts of running an M&A process as a startup . Daniel shares tactical advice on: What conditions founders should look out for at potential acquirers, as well as what established companies can do to create a more “founder-friendly” environment How to spot clear buying signals and weed out companies that are just “tire kicking” How to build meaningful relationships with executives of all types, not just corp dev teams. Techniques for including your investors in the M&A process, as well as messaging tips when opening up about the process to the wider team.  You can follow Daniel on Twitter at @ddebow. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Thu, 26 Jan 2023 09:00:00 -0000 full 80 First Round Daniel Debow, VP of Product for Demand at Shopify and a three-time founder. He shares his playbook for how founders should navigate an acquisition. Our guest today is Daniel Debow, a VP of Product for Demand at Shopify.  Daniel is a three-time founder and a seasoned M&A pro. Daniel oversaw the process of all three of his companies’ acquisitions and has helped continue to grow them at scale inside larger corporations. His most recent startup, Helpful, was acquired by Shopify in 2019. Before that, he co-founded Rypple which was acquired by Salesforce in 2011. His first startup, Workbrain, was acquired by Infor in 2007.  In our conversation today, we focus on all the moving parts of running an M&A process as a startup . Daniel shares tactical advice on: What conditions founders should look out for at potential acquirers, as well as what established companies can do to create a more “founder-friendly” environment How to spot clear buying signals and weed out companies that are just “tire kicking” How to build meaningful relationships with executives of all types, not just corp dev teams. Techniques for including your investors in the M&A process, as well as messaging tips when opening up about the process to the wider team.  You can follow Daniel on Twitter at @ddebow. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Our guest today is Daniel Debow, a VP of Product for Demand at Shopify. 


Daniel is a three-time founder and a seasoned M&A pro. Daniel oversaw the process of all three of his companies’ acquisitions and has helped continue to grow them at scale inside larger corporations. His most recent startup, Helpful, was acquired by Shopify in 2019. Before that, he co-founded Rypple which was acquired by Salesforce in 2011. His first startup, Workbrain, was acquired by Infor in 2007. 


In our conversation today, we focus on all the moving parts of running an M&A process as a startup . Daniel shares tactical advice on:


  • What conditions founders should look out for at potential acquirers, as well as what established companies can do to create a more “founder-friendly” environment
  • How to spot clear buying signals and weed out companies that are just “tire kicking”
  • How to build meaningful relationships with executives of all types, not just corp dev teams.
  • Techniques for including your investors in the M&A process, as well as messaging tips when opening up about the process to the wider team. 


You can follow Daniel on Twitter at @ddebow. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

]]> 3823 How to build your culture like a product — Lessons from Anna Binder, Asana’s Head of People https://review.firstround.com/podcast/episode-79 Our guest is Anna Binder, Head of People at Asana. We go back to the earliest days when Anna first took on the role, starting with how she prioritized the initial things to tackle as a new People exec and combing through a slew of opinions that bubbled up from other folks at the company.  Next, she shares her tactical playbook for creating a culture of feedback for not just low-performers, but high-performers, too. Anna also unpacks her methodology of conscious leadership, and how the best leaders always interrogate how the opposite might be true. She shares her insights from working on Asana’s executive team for nearly 7 years, and how to build habits to make sure this group is a healthy nucleus at the center of the company.  We end with a rapid-fire round, with some quick hits tackling onboarding, all-hands meetings, and mentors.  You can follow Anna on Twitter @annaebinder. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson  Fri, 20 Jan 2023 04:00:00 -0000 full 79 First Round Anna Binder is the Head of People at Asana, joining the company back in 2016 as its first HR executive. She shares her advice from helping weave the culture at Asana, from getting comfortable with feedback to maintaining a healthy exec team. Our guest is Anna Binder, Head of People at Asana. We go back to the earliest days when Anna first took on the role, starting with how she prioritized the initial things to tackle as a new People exec and combing through a slew of opinions that bubbled up from other folks at the company.  Next, she shares her tactical playbook for creating a culture of feedback for not just low-performers, but high-performers, too. Anna also unpacks her methodology of conscious leadership, and how the best leaders always interrogate how the opposite might be true. She shares her insights from working on Asana’s executive team for nearly 7 years, and how to build habits to make sure this group is a healthy nucleus at the center of the company.  We end with a rapid-fire round, with some quick hits tackling onboarding, all-hands meetings, and mentors.  You can follow Anna on Twitter @annaebinder. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson  Our guest is Anna Binder, Head of People at Asana.


We go back to the earliest days when Anna first took on the role, starting with how she prioritized the initial things to tackle as a new People exec and combing through a slew of opinions that bubbled up from other folks at the company. 


Next, she shares her tactical playbook for creating a culture of feedback for not just low-performers, but high-performers, too. Anna also unpacks her methodology of conscious leadership, and how the best leaders always interrogate how the opposite might be true. She shares her insights from working on Asana’s executive team for nearly 7 years, and how to build habits to make sure this group is a healthy nucleus at the center of the company. 


We end with a rapid-fire round, with some quick hits tackling onboarding, all-hands meetings, and mentors. 


You can follow Anna on Twitter @annaebinder.


You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

]]> 3880 How to scale your career alongside your startup: Mike Boufford’s lessons after 10 years at Greenhouse https://review.firstround.com/podcast/episode-78 For our first episode of 2023, our guest is Mike Boufford, CTO of Greenhouse, an applicant tracking system and recruiting platform.  Mike has a unique career as an engineering leader. He wrote the first line of code at Greenhouse in May 2012, and he’s still there — over a decade later. This isn’t the typical path of non-co-founding engineers, who usually get layered or leave to start their own ventures. In our conversation today, we focus on how founders build an environment that makes early employees want to stay, and importantly, how leaders can build the career skills and self-awareness they need to succeed at a startup long-term. Mike shares more on: How his own motivation changed over time and how he managed his relationship with the company’s co-founders.  The techniques he used to prepare himself for every next phase of growth and how his role would have to change in 18-24 months. Why he read two books on every other executive’s area of the business when he joined the leadership team. Mike also refers to his First Round Review article in the interview, which we definitely recommend reading: Why This Engineering Leader Thinks You Shouldn’t Aim for Zero Regrettable Attrition. You can follow Mike on Twitter at @mboufford. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Thu, 12 Jan 2023 09:00:00 -0000 full 78 First Round Mike Boufford wrote Greenhouse’s first line of code in 2012 and he’s still CTO today. His advice for growing and getting more strategic as a leader. For our first episode of 2023, our guest is Mike Boufford, CTO of Greenhouse, an applicant tracking system and recruiting platform.  Mike has a unique career as an engineering leader. He wrote the first line of code at Greenhouse in May 2012, and he’s still there — over a decade later. This isn’t the typical path of non-co-founding engineers, who usually get layered or leave to start their own ventures. In our conversation today, we focus on how founders build an environment that makes early employees want to stay, and importantly, how leaders can build the career skills and self-awareness they need to succeed at a startup long-term. Mike shares more on: How his own motivation changed over time and how he managed his relationship with the company’s co-founders.  The techniques he used to prepare himself for every next phase of growth and how his role would have to change in 18-24 months. Why he read two books on every other executive’s area of the business when he joined the leadership team. Mike also refers to his First Round Review article in the interview, which we definitely recommend reading: Why This Engineering Leader Thinks You Shouldn’t Aim for Zero Regrettable Attrition. You can follow Mike on Twitter at @mboufford. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  For our first episode of 2023, our guest is Mike Boufford, CTO of Greenhouse, an applicant tracking system and recruiting platform. 


Mike has a unique career as an engineering leader. He wrote the first line of code at Greenhouse in May 2012, and he’s still there — over a decade later. This isn’t the typical path of non-co-founding engineers, who usually get layered or leave to start their own ventures.


In our conversation today, we focus on how founders build an environment that makes early employees want to stay, and importantly, how leaders can build the career skills and self-awareness they need to succeed at a startup long-term. Mike shares more on:


  • How his own motivation changed over time and how he managed his relationship with the company’s co-founders. 
  • The techniques he used to prepare himself for every next phase of growth and how his role would have to change in 18-24 months.
  • Why he read two books on every other executive’s area of the business when he joined the leadership team.


Mike also refers to his First Round Review article in the interview, which we definitely recommend reading: Why This Engineering Leader Thinks You Shouldn’t Aim for Zero Regrettable Attrition.


You can follow Mike on Twitter at @mboufford. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

]]> 3717 Founders: Here’s how to get your sales pitch in ship-shape — Peter Kazanjy Our guest is Peter Kazanjy, co-founder of Atrium and author of “Founding Sales: The Early Stage Go-to-Market Handbook.” As an early-stage founder, there’s something comforting about the build stage. You’re tinkering with the nascent product, honing your MVP and dreaming up the possibilities of how much folks are going to love what you create. But once you get out of that comfort zone of quietly building and start trying to sell, things tend to get infinitely more complicated. In today’s conversation, Pete lays out the roadmap for getting founder-led sales right in the early days. From small exercises to build up your selling muscles, like his “turbo rapport” challenge to thornier topics like self-diagnosing if your selling narrative is working, he’s got tons of advice for breaking down the art of a sales call. Pete also shares tailored guidance for folks who are facing the additional hurdle of creating a new category (and trying to create a new budget), with the playbooks he used building Atrium. You can follow Peter on Twitter @Kazanjy. Check out his articles for First Round Review, including his lessons on building a customer advisory board. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 15 Dec 2022 09:00:00 -0000 full 77 First Round Peter Kazanjy is the co-founder of Atrium and the author of “Founding Sales: The Early Stage Go-To-Market Handbook.” He shares advice for getting in front of customers and nailing your pitch in the early days. Our guest is Peter Kazanjy, co-founder of Atrium and author of “Founding Sales: The Early Stage Go-to-Market Handbook.” As an early-stage founder, there’s something comforting about the build stage. You’re tinkering with the nascent product, honing your MVP and dreaming up the possibilities of how much folks are going to love what you create. But once you get out of that comfort zone of quietly building and start trying to sell, things tend to get infinitely more complicated. In today’s conversation, Pete lays out the roadmap for getting founder-led sales right in the early days. From small exercises to build up your selling muscles, like his “turbo rapport” challenge to thornier topics like self-diagnosing if your selling narrative is working, he’s got tons of advice for breaking down the art of a sales call. Pete also shares tailored guidance for folks who are facing the additional hurdle of creating a new category (and trying to create a new budget), with the playbooks he used building Atrium. You can follow Peter on Twitter @Kazanjy. Check out his articles for First Round Review, including his lessons on building a customer advisory board. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Our guest is Peter Kazanjy, co-founder of Atrium and author of “Founding Sales: The Early Stage Go-to-Market Handbook.”


As an early-stage founder, there’s something comforting about the build stage. You’re tinkering with the nascent product, honing your MVP and dreaming up the possibilities of how much folks are going to love what you create. But once you get out of that comfort zone of quietly building and start trying to sell, things tend to get infinitely more complicated.


In today’s conversation, Pete lays out the roadmap for getting founder-led sales right in the early days. From small exercises to build up your selling muscles, like his “turbo rapport” challenge to thornier topics like self-diagnosing if your selling narrative is working, he’s got tons of advice for breaking down the art of a sales call. Pete also shares tailored guidance for folks who are facing the additional hurdle of creating a new category (and trying to create a new budget), with the playbooks he used building Atrium.


You can follow Peter on Twitter @Kazanjy. Check out his articles for First Round Review, including his lessons on building a customer advisory board.


You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 3588 Deepak Rao on how X1 pivoted, launched, built a +600K-long waitlist and fundraised in tough times Todd Jackson is back on the mic to guest host another product-market fit focused episode this week. He chats with Deepak Rao, co-founder and CEO of X1, a consumer fintech startup that’s building a credit card for a new generation.  Just last week, X1 announced a $15 million funding round. But we’re here to rewind the clock and unpack how the startup got to this point. As you’ll hear in today’s conversation, the path required a dramatic pivot. Here’s a preview of what Deepak shares: The emotional journey of how the pandemic forced them to abandon the initial idea for a personal loan product. How the team validated demand for the new idea by focusing on the launch announcement and getting all of the branding exactly right — before building anything. The launch strategy that crashed X1’s website and built up a 600K long waitlist. . Why finding product-market fit is different for consumer companies, plus advice on fundraising in tough times. Whether you’re in the early innings of starting a company, going through a tough pivot yourself, or planning out your product’s launch there are tons of helpful tactics here. You can follow Deepak on Twitter at @drao1. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @tjack. Thu, 08 Dec 2022 09:00:00 -0000 full 76 First Round Deepak Rao shares the dramatic story of how X1 pivoted during the pandemic and found product-market fit with a bold launch strategy. Todd Jackson is back on the mic to guest host another product-market fit focused episode this week. He chats with Deepak Rao, co-founder and CEO of X1, a consumer fintech startup that’s building a credit card for a new generation.  Just last week, X1 announced a $15 million funding round. But we’re here to rewind the clock and unpack how the startup got to this point. As you’ll hear in today’s conversation, the path required a dramatic pivot. Here’s a preview of what Deepak shares: The emotional journey of how the pandemic forced them to abandon the initial idea for a personal loan product. How the team validated demand for the new idea by focusing on the launch announcement and getting all of the branding exactly right — before building anything. The launch strategy that crashed X1’s website and built up a 600K long waitlist. . Why finding product-market fit is different for consumer companies, plus advice on fundraising in tough times. Whether you’re in the early innings of starting a company, going through a tough pivot yourself, or planning out your product’s launch there are tons of helpful tactics here. You can follow Deepak on Twitter at @drao1. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @tjack. Todd Jackson is back on the mic to guest host another product-market fit focused episode this week. He chats with Deepak Rao, co-founder and CEO of X1, a consumer fintech startup that’s building a credit card for a new generation. 


Just last week, X1 announced a $15 million funding round. But we’re here to rewind the clock and unpack how the startup got to this point. As you’ll hear in today’s conversation, the path required a dramatic pivot. Here’s a preview of what Deepak shares:


  • The emotional journey of how the pandemic forced them to abandon the initial idea for a personal loan product.
  • How the team validated demand for the new idea by focusing on the launch announcement and getting all of the branding exactly right — before building anything.
  • The launch strategy that crashed X1’s website and built up a 600K long waitlist. .
  • Why finding product-market fit is different for consumer companies, plus advice on fundraising in tough times.


Whether you’re in the early innings of starting a company, going through a tough pivot yourself, or planning out your product’s launch there are tons of helpful tactics here.


You can follow Deepak on Twitter at @drao1. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @tjack.

]]> 3368 How to lower barriers to change when building and selling products — Jonah Berger’s advice for founders https://review.firstround.com/podcast/episode-75 Our guest today is Jonah Berger, a marketing professor at the Wharton School at the University of Pennsylvania and the bestselling author of “Contagious” and “Invisible Influence.”  Today we’re chatting about his follow-up book, “The Catalyst: How to Change Anyone’s Mind.” Founders start companies to change industries and behaviors, but change is hard. Going back to chemistry, Jonah notes that catalysts don't just create change by pushing harder or exerting more energy — they remove or lower the barriers to change. (In the book Jonah offers a helpful framework about 5 specific barriers to change, called REDUCE — which stands for reactance, endowment, distance, uncertainty, and corroborating evidence.) We focus on how founders and leaders can do that in the context of building and selling products. Jonah shares his thoughts on: Whether you truly need to build a 10X better product and why a startup’s biggest competitor is actually inertia.  The role of urgency in selling or getting someone to adopt a product. How to apply the freemium approach in different contexts, like with physical products. Techniques for negotiating price, as well as the role that identity and category creation play in persuasion and product adoption. You can follow Jonah on Twitter at @j1berger. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Thu, 01 Dec 2022 09:00:00 -0000 full 74 First Round Wharton professor and author Jonah Berger on overcoming barriers to change when building breakthrough products, convincing customers or leading teams. Our guest today is Jonah Berger, a marketing professor at the Wharton School at the University of Pennsylvania and the bestselling author of “Contagious” and “Invisible Influence.”  Today we’re chatting about his follow-up book, “The Catalyst: How to Change Anyone’s Mind.” Founders start companies to change industries and behaviors, but change is hard. Going back to chemistry, Jonah notes that catalysts don't just create change by pushing harder or exerting more energy — they remove or lower the barriers to change. (In the book Jonah offers a helpful framework about 5 specific barriers to change, called REDUCE — which stands for reactance, endowment, distance, uncertainty, and corroborating evidence.) We focus on how founders and leaders can do that in the context of building and selling products. Jonah shares his thoughts on: Whether you truly need to build a 10X better product and why a startup’s biggest competitor is actually inertia.  The role of urgency in selling or getting someone to adopt a product. How to apply the freemium approach in different contexts, like with physical products. Techniques for negotiating price, as well as the role that identity and category creation play in persuasion and product adoption. You can follow Jonah on Twitter at @j1berger. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Our guest today is Jonah Berger, a marketing professor at the Wharton School at the University of Pennsylvania and the bestselling author of “Contagious” and “Invisible Influence.” 


Today we’re chatting about his follow-up book, “The Catalyst: How to Change Anyone’s Mind.” Founders start companies to change industries and behaviors, but change is hard. Going back to chemistry, Jonah notes that catalysts don't just create change by pushing harder or exerting more energy — they remove or lower the barriers to change. (In the book Jonah offers a helpful framework about 5 specific barriers to change, called REDUCE — which stands for reactance, endowment, distance, uncertainty, and corroborating evidence.)


We focus on how founders and leaders can do that in the context of building and selling products. Jonah shares his thoughts on:

  • Whether you truly need to build a 10X better product and why a startup’s biggest competitor is actually inertia. 
  • The role of urgency in selling or getting someone to adopt a product.
  • How to apply the freemium approach in different contexts, like with physical products.
  • Techniques for negotiating price, as well as the role that identity and category creation play in persuasion and product adoption.


You can follow Jonah on Twitter at @j1berger. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

]]> 3448 How Retool reached $2M in ARR before launch by focusing on developers — David Hsu Todd Jackson is back on the mic to guest host another product-focused episode this week. He chats with David Hsu, founder and CEO of Retool, a low-code platform for developers building custom internal tools. Today, Retool is valued at over $3 billion and has some of the biggest companies in the world building apps on its platform. But in this conversation, David rewinds the clock to Retool’s early days. He discusses why plenty of smart folks thought the idea for Retool would fail and that the product’s developer focus would sink the company. We explore why David had such strong conviction in his target customer, even in the face of doubters, and his early lessons on finding language-market fit. David also explains how Retool nabbed its earliest customers (which includes Brex, DoorDash and a Fortune 500 BigCo) and shares his playbook for creating incredibly tight feedback cycles with these early evangelists. On the surface, Retool’s path to product-market fit seems incredibly smooth. But as David tells it, there were plenty of bumps in the road — and he’s got tons of advice for early-stage founders that are finding their footing. Thu, 10 Nov 2022 09:00:00 -0000 full 74 First Round David Hsu is the founder and CEO of Retool, a low-code platform for developers building custom internal tools. He goes back to the early days of ideating on and building Retool, from going against the grain with his product idea, finding language/market fit, and signing on early customers in the Fortune 500. Todd Jackson is back on the mic to guest host another product-focused episode this week. He chats with David Hsu, founder and CEO of Retool, a low-code platform for developers building custom internal tools. Today, Retool is valued at over $3 billion and has some of the biggest companies in the world building apps on its platform. But in this conversation, David rewinds the clock to Retool’s early days. He discusses why plenty of smart folks thought the idea for Retool would fail and that the product’s developer focus would sink the company. We explore why David had such strong conviction in his target customer, even in the face of doubters, and his early lessons on finding language-market fit. David also explains how Retool nabbed its earliest customers (which includes Brex, DoorDash and a Fortune 500 BigCo) and shares his playbook for creating incredibly tight feedback cycles with these early evangelists. On the surface, Retool’s path to product-market fit seems incredibly smooth. But as David tells it, there were plenty of bumps in the road — and he’s got tons of advice for early-stage founders that are finding their footing. Todd Jackson is back on the mic to guest host another product-focused episode this week. He chats with David Hsu, founder and CEO of Retool, a low-code platform for developers building custom internal tools.


Today, Retool is valued at over $3 billion and has some of the biggest companies in the world building apps on its platform. But in this conversation, David rewinds the clock to Retool’s early days. He discusses why plenty of smart folks thought the idea for Retool would fail and that the product’s developer focus would sink the company.


We explore why David had such strong conviction in his target customer, even in the face of doubters, and his early lessons on finding language-market fit. David also explains how Retool nabbed its earliest customers (which includes Brex, DoorDash and a Fortune 500 BigCo) and shares his playbook for creating incredibly tight feedback cycles with these early evangelists.


On the surface, Retool’s path to product-market fit seems incredibly smooth. But as David tells it, there were plenty of bumps in the road — and he’s got tons of advice for early-stage founders that are finding their footing.

]]> 3391 How to approach GTM with an engineering lens — Rich Rao’s advice from Google & Meta Our guest is Rich Rao, the VP of the Small Business Group at Meta, where he manages the global revenue and operations for properties including Facebook, Instagram and WhatsApp. He also spent 10 years at Google, where he held a bunch of different go-to-market roles at the company, eventually becoming the GM for the Devices and Education verticals. In today’s conversation, Rich shares how his engineering background influences his approach to GTM, from his architecture method to the concept of refactoring. We also wind back the clock to his earliest days at Google on the team that was building and selling Gmail for your domain. There are a ton of early startup mental models that Rich shares from this period in the company’s history, including why they ended up ditching free trials and his biggest pricing lessons. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson. Thu, 03 Nov 2022 08:00:00 -0000 full 73 First Round Rich Rao is the VP, Small Business Group at Meta and former GM at Google. He uses his technical background to explain how leaders can apply an engineer’s playbook to their go-to-market strategy. Our guest is Rich Rao, the VP of the Small Business Group at Meta, where he manages the global revenue and operations for properties including Facebook, Instagram and WhatsApp. He also spent 10 years at Google, where he held a bunch of different go-to-market roles at the company, eventually becoming the GM for the Devices and Education verticals. In today’s conversation, Rich shares how his engineering background influences his approach to GTM, from his architecture method to the concept of refactoring. We also wind back the clock to his earliest days at Google on the team that was building and selling Gmail for your domain. There are a ton of early startup mental models that Rich shares from this period in the company’s history, including why they ended up ditching free trials and his biggest pricing lessons. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson. Our guest is Rich Rao, the VP of the Small Business Group at Meta, where he manages the global revenue and operations for properties including Facebook, Instagram and WhatsApp. He also spent 10 years at Google, where he held a bunch of different go-to-market roles at the company, eventually becoming the GM for the Devices and Education verticals.


In today’s conversation, Rich shares how his engineering background influences his approach to GTM, from his architecture method to the concept of refactoring. We also wind back the clock to his earliest days at Google on the team that was building and selling Gmail for your domain. There are a ton of early startup mental models that Rich shares from this period in the company’s history, including why they ended up ditching free trials and his biggest pricing lessons.


You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson.

]]> 3565 What startups can learn from enterprise corporate messaging — Sara Varni’s lessons from Salesforce & Twilio Our guest is Sara Varni, CMO of Attentive, a conversational commerce platform. Before joining Attentive, Sara was Twilio’s CMO and spent 10 years as a senior marketing leader at Salesforce. In today’s conversation, we talk about what startups can learn from enterprise marketing playbooks, particularly around creating and honing a corporate message. Sara takes us behind the scenes at how companies like Twilio and Salesforce craft a corporate message from the ground up, and tweak it as the company grows. She also shares specific advice for marketers with sights on the CMO seat, including how to form collaborative, not combative relationships with sales counterparts. You can follow Sara on Twitter at @SaraVarniBright You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 27 Oct 2022 08:00:00 -0000 full 72 First Round Sara Varni is the CMO of Attentive. She shares her biggest lessons from her marketing leadership career at Salesforce and Twilio, and what startups should know about crafting a corporate message that resonates. Our guest is Sara Varni, CMO of Attentive, a conversational commerce platform. Before joining Attentive, Sara was Twilio’s CMO and spent 10 years as a senior marketing leader at Salesforce. In today’s conversation, we talk about what startups can learn from enterprise marketing playbooks, particularly around creating and honing a corporate message. Sara takes us behind the scenes at how companies like Twilio and Salesforce craft a corporate message from the ground up, and tweak it as the company grows. She also shares specific advice for marketers with sights on the CMO seat, including how to form collaborative, not combative relationships with sales counterparts. You can follow Sara on Twitter at @SaraVarniBright You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Our guest is Sara Varni, CMO of Attentive, a conversational commerce platform. Before joining Attentive, Sara was Twilio’s CMO and spent 10 years as a senior marketing leader at Salesforce.


In today’s conversation, we talk about what startups can learn from enterprise marketing playbooks, particularly around creating and honing a corporate message. Sara takes us behind the scenes at how companies like Twilio and Salesforce craft a corporate message from the ground up, and tweak it as the company grows. She also shares specific advice for marketers with sights on the CMO seat, including how to form collaborative, not combative relationships with sales counterparts.


You can follow Sara on Twitter at @SaraVarniBright


You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 2952 Finding product-market fit twice — Alma’s Harry Ritter on pivots and staying close to customers https://review.firstround.com/podcast/episode-71 Todd Jackson’s back on the mic this week. (As a reminder, he’s guest hosting a few product-focused episodes this season — all about finding product-market fit.) Today, Todd chats with Harry Ritter, founder of Alma, a membership-based network that helps independent mental health care providers accept insurance and build thriving private practices. In our conversation, we go deep into Alma’s early days, and how they navigated the journey of finding traction and scaling.  As you’ll hear in the episode, the Alma team essentially had to find product-market fit twice as they went from physical, co-working office spaces pre-pandemic, to quickly building out their virtual care capabilities. Here’s a preview of what Todd and Harry cover: Approaching team building as a solo founder Refining the idea and getting more insights from your customers through structured interviews, using the technique doctors are trained on Rallying your team through a pivot Staying competitor aware — not competitor obsessed The difference between building a marketplace versus a platform. Whether you’re in the early stages of starting a company or going through a tough pivot, there are tons of helpful tactics here. You can follow Harry on Twitter at @harryritter1. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @tjack. Thu, 13 Oct 2022 08:00:00 -0000 full 71 First Round Founder Harry Ritter dives into Alma’s journey to product-market fit, with advice on rallying through tough pivots and building as a solo founder. Todd Jackson’s back on the mic this week. (As a reminder, he’s guest hosting a few product-focused episodes this season — all about finding product-market fit.) Today, Todd chats with Harry Ritter, founder of Alma, a membership-based network that helps independent mental health care providers accept insurance and build thriving private practices. In our conversation, we go deep into Alma’s early days, and how they navigated the journey of finding traction and scaling.  As you’ll hear in the episode, the Alma team essentially had to find product-market fit twice as they went from physical, co-working office spaces pre-pandemic, to quickly building out their virtual care capabilities. Here’s a preview of what Todd and Harry cover: Approaching team building as a solo founder Refining the idea and getting more insights from your customers through structured interviews, using the technique doctors are trained on Rallying your team through a pivot Staying competitor aware — not competitor obsessed The difference between building a marketplace versus a platform. Whether you’re in the early stages of starting a company or going through a tough pivot, there are tons of helpful tactics here. You can follow Harry on Twitter at @harryritter1. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @tjack. Todd Jackson’s back on the mic this week. (As a reminder, he’s guest hosting a few product-focused episodes this season — all about finding product-market fit.)


Today, Todd chats with Harry Ritter, founder of Alma, a membership-based network that helps independent mental health care providers accept insurance and build thriving private practices.


In our conversation, we go deep into Alma’s early days, and how they navigated the journey of finding traction and scaling. 


As you’ll hear in the episode, the Alma team essentially had to find product-market fit twice as they went from physical, co-working office spaces pre-pandemic, to quickly building out their virtual care capabilities.


Here’s a preview of what Todd and Harry cover:


  • Approaching team building as a solo founder
  • Refining the idea and getting more insights from your customers through structured interviews, using the technique doctors are trained on
  • Rallying your team through a pivot
  • Staying competitor aware — not competitor obsessed
  • The difference between building a marketplace versus a platform.


Whether you’re in the early stages of starting a company or going through a tough pivot, there are tons of helpful tactics here.


You can follow Harry on Twitter at @harryritter1. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @tjack.

]]> 2948 Why everything we’ve been taught about quitting is wrong — Annie Duke https://review.firstround.com/podcast/episode-70 Our guest is Annie Duke, a retired pro poker player and First Round’s Special Partner focused on Decision Science. She’s also the author of the bestselling book, “Thinking in Bets.” In today’s conversation, we’re talking about her follow-up to that book, titled “Quit: The Power of Knowing When to Walk Away,” which was just released this week. Quitting is not a popular topic in startup circles and history is marked by success stories of founders who refused to quit, even when just about every signal was telling them to do so. But Annie offers a counterintuitive approach. She dives into all the misconceptions about quitting, and makes the case that it can actually be a superpower, rather than a weakness. Annie explores the psychology behind why it’s so hard to walk away, and tactically what folks can do to get a clearer picture of the decisions ahead of them, rather than being clouded by biases. She also offers specific advice for advice-givers who are trying to nudge someone to change course, with tested tips for getting your message across gently, yet firmly. And after the episode be sure to check out “Quit: The Power of Knowing When to Walk Away.” You can follow Annie on Twitter at @AnnieDuke. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 06 Oct 2022 08:00:00 -0000 full 70 First Round Annie Duke is First Round’s Special Partner of Decision Science. On the heels of releasing her new book, “Quit: The Power of Knowing When to Walk Away,” she dives into all of our misconceptions about quitting and makes the case that getting better at this skill lays the groundwork for greater success. Our guest is Annie Duke, a retired pro poker player and First Round’s Special Partner focused on Decision Science. She’s also the author of the bestselling book, “Thinking in Bets.” In today’s conversation, we’re talking about her follow-up to that book, titled “Quit: The Power of Knowing When to Walk Away,” which was just released this week. Quitting is not a popular topic in startup circles and history is marked by success stories of founders who refused to quit, even when just about every signal was telling them to do so. But Annie offers a counterintuitive approach. She dives into all the misconceptions about quitting, and makes the case that it can actually be a superpower, rather than a weakness. Annie explores the psychology behind why it’s so hard to walk away, and tactically what folks can do to get a clearer picture of the decisions ahead of them, rather than being clouded by biases. She also offers specific advice for advice-givers who are trying to nudge someone to change course, with tested tips for getting your message across gently, yet firmly. And after the episode be sure to check out “Quit: The Power of Knowing When to Walk Away.” You can follow Annie on Twitter at @AnnieDuke. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Our guest is Annie Duke, a retired pro poker player and First Round’s Special Partner focused on Decision Science. She’s also the author of the bestselling book, “Thinking in Bets.”


In today’s conversation, we’re talking about her follow-up to that book, titled “Quit: The Power of Knowing When to Walk Away,” which was just released this week.


Quitting is not a popular topic in startup circles and history is marked by success stories of founders who refused to quit, even when just about every signal was telling them to do so.


But Annie offers a counterintuitive approach. She dives into all the misconceptions about quitting, and makes the case that it can actually be a superpower, rather than a weakness. Annie explores the psychology behind why it’s so hard to walk away, and tactically what folks can do to get a clearer picture of the decisions ahead of them, rather than being clouded by biases. She also offers specific advice for advice-givers who are trying to nudge someone to change course, with tested tips for getting your message across gently, yet firmly.


And after the episode be sure to check out “Quit: The Power of Knowing When to Walk Away.”


You can follow Annie on Twitter at @AnnieDuke.


You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 4445 How to scale your co-founder relationship alongside your startup — Manu Sharma & Brian Rieger of Labelbox Our guests are Manu Sharma and Brian Rieger, co-founders of Labelbox. In this interview, we take a microscope to their co-founder DNA, exploring the ins and outs of how they’ve made the relationship work over the years. We discuss: How Manu and Brian came together as co-founders and landed on the idea for Labelbox. How they intentionally aligned their skillsets, values and responsibilities before writing a line of code. Their rituals for spending valuable time together as the company grows, including thought-starter questions for deep discussions and sharing an executive coach. How they run the executive team at scale and sketch out decision rights. Manu and Brian both have extremely valuable advice to other founders, either those in the early stages of looking for a co-founder, or folks who want to add a little magic to an existing co-founding relationship. You can follow Manu at @manuaero and Brian at @RiegerB on Twitter. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 29 Sep 2022 08:00:00 -0000 full 69 First Round Manu Sharma and Brian Rieger are the co-founders of Labelbox and in this conversation, they take a microscope to their co-founder DNA and share tons of advice for other entrepreneurs looking for magic in their founding team. Our guests are Manu Sharma and Brian Rieger, co-founders of Labelbox. In this interview, we take a microscope to their co-founder DNA, exploring the ins and outs of how they’ve made the relationship work over the years. We discuss: How Manu and Brian came together as co-founders and landed on the idea for Labelbox. How they intentionally aligned their skillsets, values and responsibilities before writing a line of code. Their rituals for spending valuable time together as the company grows, including thought-starter questions for deep discussions and sharing an executive coach. How they run the executive team at scale and sketch out decision rights. Manu and Brian both have extremely valuable advice to other founders, either those in the early stages of looking for a co-founder, or folks who want to add a little magic to an existing co-founding relationship. You can follow Manu at @manuaero and Brian at @RiegerB on Twitter. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Our guests are Manu Sharma and Brian Rieger, co-founders of Labelbox.


In this interview, we take a microscope to their co-founder DNA, exploring the ins and outs of how they’ve made the relationship work over the years. We discuss:

  • How Manu and Brian came together as co-founders and landed on the idea for Labelbox.
  • How they intentionally aligned their skillsets, values and responsibilities before writing a line of code.
  • Their rituals for spending valuable time together as the company grows, including thought-starter questions for deep discussions and sharing an executive coach.
  • How they run the executive team at scale and sketch out decision rights.

Manu and Brian both have extremely valuable advice to other founders, either those in the early stages of looking for a co-founder, or folks who want to add a little magic to an existing co-founding relationship.


You can follow Manu at @manuaero and Brian at @RiegerB on Twitter.


You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 2892 A crash course on founder-led customer success — Sydney Strader’s lessons from Catalyst & InVision https://review.firstround.com/podcast/episode-68 Today’s episode is with Sydney Strader, VP of Customer Success at Catalyst. Prior to joining Catalyst, Sydney was the VP of Customer Success at InVision. In our conversation we focus on founder-led customer success, an area of early company building that’s often overlooked. Here’s a preview of her tactical advice: How to structure early customer check-ins, plus a framework to help surface more specific feedback.  The most impactful questions that founders and customer success managers should ask all their customers. Why everyone at the company owns the net revenue retention metric — not just the customer success function. How to make your first customer success hire, from the ideal profile to structuring the interview process and setting comp.  You can follow Sydney on Twitter at @sydneystrader. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Thu, 22 Sep 2022 08:00:00 -0000 full 68 First Round Sydney Strader shares tips from Catalyst & InVision on founder-led customer success, from structuring customer conversations to making the first hire. Today’s episode is with Sydney Strader, VP of Customer Success at Catalyst. Prior to joining Catalyst, Sydney was the VP of Customer Success at InVision. In our conversation we focus on founder-led customer success, an area of early company building that’s often overlooked. Here’s a preview of her tactical advice: How to structure early customer check-ins, plus a framework to help surface more specific feedback.  The most impactful questions that founders and customer success managers should ask all their customers. Why everyone at the company owns the net revenue retention metric — not just the customer success function. How to make your first customer success hire, from the ideal profile to structuring the interview process and setting comp.  You can follow Sydney on Twitter at @sydneystrader. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Today’s episode is with Sydney Strader, VP of Customer Success at Catalyst. Prior to joining Catalyst, Sydney was the VP of Customer Success at InVision.


In our conversation we focus on founder-led customer success, an area of early company building that’s often overlooked. Here’s a preview of her tactical advice:


  • How to structure early customer check-ins, plus a framework to help surface more specific feedback. 
  • The most impactful questions that founders and customer success managers should ask all their customers.
  • Why everyone at the company owns the net revenue retention metric — not just the customer success function.
  • How to make your first customer success hire, from the ideal profile to structuring the interview process and setting comp. 


You can follow Sydney on Twitter at @sydneystrader. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

]]> 3516 The founder’s guide to making your first few hires — Steven Bartel on recruiting at Gem & Dropbox https://review.firstround.com/podcast/episode-67 Today’s episode is with Steven Bartel, co-founder and CEO of Gem. Before building the talent acquisition platform, Steven was an early engineer at Dropbox, where he spent 5 years working on analytics, Dropbox Paper, and hiring as the company grew from 25 to 1500 people. This experience from Dropbox, combined with his lessons from building out Gem’s own team and talking to his customer base of recruiters makes Steven the perfect person to talk to about early-stage recruiting. In our conversation we focus on how to make those fourth, fifth, or tenth hires — those really early days when your startup has zero brand recognition or recruiting help. Here’s a preview of his tactical advice: A trick for sourcing second-degree network connections The power of sending a “break-up” message in your candidate outreach.  How Gem brought candidates on to work with them in very structured trial periods before making a full-time offer.  Advice for working on your recruiting pitch and nurturing passive talent The similarities between early-stage hiring and founder-led sales You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson  Thu, 15 Sep 2022 08:00:00 -0000 full 67 First Round Gem co-founder Steven Bartel shares tactics for recruiting the first 10 hires, from sourcing and nurturing passive talent, to structuring interviews. Today’s episode is with Steven Bartel, co-founder and CEO of Gem. Before building the talent acquisition platform, Steven was an early engineer at Dropbox, where he spent 5 years working on analytics, Dropbox Paper, and hiring as the company grew from 25 to 1500 people. This experience from Dropbox, combined with his lessons from building out Gem’s own team and talking to his customer base of recruiters makes Steven the perfect person to talk to about early-stage recruiting. In our conversation we focus on how to make those fourth, fifth, or tenth hires — those really early days when your startup has zero brand recognition or recruiting help. Here’s a preview of his tactical advice: A trick for sourcing second-degree network connections The power of sending a “break-up” message in your candidate outreach.  How Gem brought candidates on to work with them in very structured trial periods before making a full-time offer.  Advice for working on your recruiting pitch and nurturing passive talent The similarities between early-stage hiring and founder-led sales You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson  Today’s episode is with Steven Bartel, co-founder and CEO of Gem.


Before building the talent acquisition platform, Steven was an early engineer at Dropbox, where he spent 5 years working on analytics, Dropbox Paper, and hiring as the company grew from 25 to 1500 people.


This experience from Dropbox, combined with his lessons from building out Gem’s own team and talking to his customer base of recruiters makes Steven the perfect person to talk to about early-stage recruiting.


In our conversation we focus on how to make those fourth, fifth, or tenth hires — those really early days when your startup has zero brand recognition or recruiting help. Here’s a preview of his tactical advice:

  • A trick for sourcing second-degree network connections
  • The power of sending a “break-up” message in your candidate outreach. 
  • How Gem brought candidates on to work with them in very structured trial periods before making a full-time offer. 
  • Advice for working on your recruiting pitch and nurturing passive talent
  • The similarities between early-stage hiring and founder-led sales


You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson 

]]> 3340 From product roadmapping to sprint planning: How to ship software at scale — Snir Kodesh Today’s episode is with Snir Kodesh, Head of Engineering at Retool, which is a development platform for building custom business tools. Before joining Retool, Snir spent six years as a Senior Director of Engineering at Lyft. In our conversation, we cover some of the biggest differences between leading engineering teams for a consumer product versus an enterprise platform — and the things that are consistent across both orgs. First, Snir pulls back the curtain on the software development cycle, starting with setting the product roadmap while balancing a diverse set of customer needs. He outlines who’s in the room to represent product, engineering and design, and what those meetings actually look and sound like. Next, he dives into how engineering actually starts taking that product roadmap and making a plan of action using the “try, do, consider” framework. He makes the case for leaning on QBRs instead of OKRs, why scope creep gets a bad rap, and his advice for getting better at estimating how long a feature will actually take to complete. Finally, we zoom out and cover his essential advice for engineering leaders — especially folks who are scaling quickly from leading a small team to a much bigger one. You can follow Snir on Twitter at @snirkodesh You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 08 Sep 2022 08:00:00 -0000 full 66 First Round Snir Kodesh is the Head of Engineering at Retool and former Senior Director of Engineering at Lyft. He unpacks the ins and outs of shipping software, from agreeing on the product roadmap, to setting your course, and getting better at estimating your development cycles. Today’s episode is with Snir Kodesh, Head of Engineering at Retool, which is a development platform for building custom business tools. Before joining Retool, Snir spent six years as a Senior Director of Engineering at Lyft. In our conversation, we cover some of the biggest differences between leading engineering teams for a consumer product versus an enterprise platform — and the things that are consistent across both orgs. First, Snir pulls back the curtain on the software development cycle, starting with setting the product roadmap while balancing a diverse set of customer needs. He outlines who’s in the room to represent product, engineering and design, and what those meetings actually look and sound like. Next, he dives into how engineering actually starts taking that product roadmap and making a plan of action using the “try, do, consider” framework. He makes the case for leaning on QBRs instead of OKRs, why scope creep gets a bad rap, and his advice for getting better at estimating how long a feature will actually take to complete. Finally, we zoom out and cover his essential advice for engineering leaders — especially folks who are scaling quickly from leading a small team to a much bigger one. You can follow Snir on Twitter at @snirkodesh You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Today’s episode is with Snir Kodesh, Head of Engineering at Retool, which is a development platform for building custom business tools. Before joining Retool, Snir spent six years as a Senior Director of Engineering at Lyft.


In our conversation, we cover some of the biggest differences between leading engineering teams for a consumer product versus an enterprise platform — and the things that are consistent across both orgs.


First, Snir pulls back the curtain on the software development cycle, starting with setting the product roadmap while balancing a diverse set of customer needs. He outlines who’s in the room to represent product, engineering and design, and what those meetings actually look and sound like.


Next, he dives into how engineering actually starts taking that product roadmap and making a plan of action using the “try, do, consider” framework. He makes the case for leaning on QBRs instead of OKRs, why scope creep gets a bad rap, and his advice for getting better at estimating how long a feature will actually take to complete.


Finally, we zoom out and cover his essential advice for engineering leaders — especially folks who are scaling quickly from leading a small team to a much bigger one.


You can follow Snir on Twitter at @snirkodesh


You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 3209 The 5 phases of Figma’s community-led growth — Claire Butler Today’s episode is with Claire Butler, Senior Director of Marketing at Figma, and one of the company’s first 10 employees. In today’s conversation, she sketches out Figma’s five phases of community-led growth — and shares tons of advice along the way for startups who also are looking to build an organic growth engine. In the first phase, Claire covers the biggest lessons from Figma’s years of stealth mode — and how you can start planting the seeds for a community when you don’t have a fully-formed product. She also unpacks the decision to eventually emerge from stealth, after years of quietly building. In the second phase, Claire opens up the pages of Figma’s launch playbook — from taking over design Twitter, to marketing to folks who tend to bristle at traditional SaaS marketing. In the third phase, she shares how Figma leveraged the community to get folks to try the product, even if they weren’t going to switch over right away to designing in Figma full-time. In this phase of community-building, Figma built out its evangelist strategy and Claire shares tons of tips for generating excitement around your nascent product. In the final two phases, Figma needed to connect the individual users that loved the product with a larger enterprise strategy. They didn’t layer in a sales team until four years after the product launched, and didn’t add a paid product tier until another two years after that. Claire explores the ins and outs of these GTM trade-offs. You can follow Claire on Twitter at @clairetbutler You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 01 Sep 2022 08:00:00 -0000 full 65 First Round Claire Butler, Figma’s first business hire, walks us through the different phases of the company’s community-led growth model — from planting the seeds in stealth all the way to org-wide enterprise adoption. Today’s episode is with Claire Butler, Senior Director of Marketing at Figma, and one of the company’s first 10 employees. In today’s conversation, she sketches out Figma’s five phases of community-led growth — and shares tons of advice along the way for startups who also are looking to build an organic growth engine. In the first phase, Claire covers the biggest lessons from Figma’s years of stealth mode — and how you can start planting the seeds for a community when you don’t have a fully-formed product. She also unpacks the decision to eventually emerge from stealth, after years of quietly building. In the second phase, Claire opens up the pages of Figma’s launch playbook — from taking over design Twitter, to marketing to folks who tend to bristle at traditional SaaS marketing. In the third phase, she shares how Figma leveraged the community to get folks to try the product, even if they weren’t going to switch over right away to designing in Figma full-time. In this phase of community-building, Figma built out its evangelist strategy and Claire shares tons of tips for generating excitement around your nascent product. In the final two phases, Figma needed to connect the individual users that loved the product with a larger enterprise strategy. They didn’t layer in a sales team until four years after the product launched, and didn’t add a paid product tier until another two years after that. Claire explores the ins and outs of these GTM trade-offs. You can follow Claire on Twitter at @clairetbutler You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Today’s episode is with Claire Butler, Senior Director of Marketing at Figma, and one of the company’s first 10 employees.


In today’s conversation, she sketches out Figma’s five phases of community-led growth — and shares tons of advice along the way for startups who also are looking to build an organic growth engine.


In the first phase, Claire covers the biggest lessons from Figma’s years of stealth mode — and how you can start planting the seeds for a community when you don’t have a fully-formed product. She also unpacks the decision to eventually emerge from stealth, after years of quietly building.


In the second phase, Claire opens up the pages of Figma’s launch playbook — from taking over design Twitter, to marketing to folks who tend to bristle at traditional SaaS marketing.


In the third phase, she shares how Figma leveraged the community to get folks to try the product, even if they weren’t going to switch over right away to designing in Figma full-time. In this phase of community-building, Figma built out its evangelist strategy and Claire shares tons of tips for generating excitement around your nascent product.


In the final two phases, Figma needed to connect the individual users that loved the product with a larger enterprise strategy. They didn’t layer in a sales team until four years after the product launched, and didn’t add a paid product tier until another two years after that. Claire explores the ins and outs of these GTM trade-offs.


You can follow Claire on Twitter at @clairetbutler


You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 3468 Airtable’s path to product-market fit — co-founder Andrew Ofstad on building horizontal products https://review.firstround.com/podcast/episode-64 Todd Jackson’s filling in as host again this week. (As a reminder, he’s hosting a few product-focused episodes this season — all about finding product-market fit.) Today, Todd chats with Andrew Ofstad, co-founder of Airtable. In our conversation, we go deep into Airtable’s early days, and how they navigated the journey of finding traction and scaling. Here’s a preview of what Todd and Andrew cover: How the founders came together, their vision for the product, and what the initial prototypes looked like.  Airtable’s alpha, beta, and launch timelines, as well as their early traction. The challenges of creating a horizontal product that can do many things, including identifying initial use cases and figuring out how to describe what they were building. How to approach pricing and competition, as well as their early go-to-market strategy. What the next 3 years will look like for Airtable, and how they’ve navigated scaling while staying true to their vision. Whether you’re a founder validating your own idea, or a product leader looking for growth advice, there are tons of tactics here that go much deeper than the typical founding stories you hear. You can follow Andrew on Twitter at @aofstad. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @tjack. Thu, 18 Aug 2022 08:00:00 -0000 full 64 First Round Airtable’s co-founder Andrew Ofstad shares Airtable’s early journey to product-market fit — from prototypes and launch, to go-to-market strategy. Todd Jackson’s filling in as host again this week. (As a reminder, he’s hosting a few product-focused episodes this season — all about finding product-market fit.) Today, Todd chats with Andrew Ofstad, co-founder of Airtable. In our conversation, we go deep into Airtable’s early days, and how they navigated the journey of finding traction and scaling. Here’s a preview of what Todd and Andrew cover: How the founders came together, their vision for the product, and what the initial prototypes looked like.  Airtable’s alpha, beta, and launch timelines, as well as their early traction. The challenges of creating a horizontal product that can do many things, including identifying initial use cases and figuring out how to describe what they were building. How to approach pricing and competition, as well as their early go-to-market strategy. What the next 3 years will look like for Airtable, and how they’ve navigated scaling while staying true to their vision. Whether you’re a founder validating your own idea, or a product leader looking for growth advice, there are tons of tactics here that go much deeper than the typical founding stories you hear. You can follow Andrew on Twitter at @aofstad. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @tjack. Todd Jackson’s filling in as host again this week. (As a reminder, he’s hosting a few product-focused episodes this season — all about finding product-market fit.)


Today, Todd chats with Andrew Ofstad, co-founder of Airtable. In our conversation, we go deep into Airtable’s early days, and how they navigated the journey of finding traction and scaling.


Here’s a preview of what Todd and Andrew cover:


  • How the founders came together, their vision for the product, and what the initial prototypes looked like. 


  • Airtable’s alpha, beta, and launch timelines, as well as their early traction.


  • The challenges of creating a horizontal product that can do many things, including identifying initial use cases and figuring out how to describe what they were building.


  • How to approach pricing and competition, as well as their early go-to-market strategy.


  • What the next 3 years will look like for Airtable, and how they’ve navigated scaling while staying true to their vision.


Whether you’re a founder validating your own idea, or a product leader looking for growth advice, there are tons of tactics here that go much deeper than the typical founding stories you hear.


You can follow Andrew on Twitter at @aofstad. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @tjack.

]]> 2788 Operations vs. Algorithms: Advice for scaling startups, from Opendoor CTO Ian Wong Today’s episode is with Ian Wong, co-founder and CTO of Opendoor. Before founding Opendoor, Ian was Square’s first data scientist, where he developed machine learning models and infrastructure for fraud detection. In today’s conversation, we cover his essential advice for how to integrate data science into your startup. As Ian puts it, in the early innings it might make sense for your startup to be operations heavy. But as you start to scale, data science becomes a critical component for running a business with longevity in mind. We dive into how both Square and Opendoor approached this transition. Along those lines, we discuss some of the early considerations for your fledgling data science team, including the type of folks to hire for the early team, like whether to look for generalists or specialists, and how to set up your interview loops. Ian also dives into his lessons on structuring the data science function so that it’s deeply integrated with the rest of the technical org. Next, we dive into some of his biggest lessons as a first-time founder and CTO, including his practice with Opendoor’s leadership team of doing pre-mortems to predict why something might not work. He also encourages founders to run through a bi-yearly exercise of re-writing their job rec. You can follow Ian on Twitter at @ihat You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 11 Aug 2022 08:00:00 -0000 full 63 First Round Ian Wong is the co-founder and CTO of Opendoor. He discusses the tricky balance between operations and data science in the early days of the startup, and his advice for other founders looking to make data science core to their business. Today’s episode is with Ian Wong, co-founder and CTO of Opendoor. Before founding Opendoor, Ian was Square’s first data scientist, where he developed machine learning models and infrastructure for fraud detection. In today’s conversation, we cover his essential advice for how to integrate data science into your startup. As Ian puts it, in the early innings it might make sense for your startup to be operations heavy. But as you start to scale, data science becomes a critical component for running a business with longevity in mind. We dive into how both Square and Opendoor approached this transition. Along those lines, we discuss some of the early considerations for your fledgling data science team, including the type of folks to hire for the early team, like whether to look for generalists or specialists, and how to set up your interview loops. Ian also dives into his lessons on structuring the data science function so that it’s deeply integrated with the rest of the technical org. Next, we dive into some of his biggest lessons as a first-time founder and CTO, including his practice with Opendoor’s leadership team of doing pre-mortems to predict why something might not work. He also encourages founders to run through a bi-yearly exercise of re-writing their job rec. You can follow Ian on Twitter at @ihat You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Today’s episode is with Ian Wong, co-founder and CTO of Opendoor. Before founding Opendoor, Ian was Square’s first data scientist, where he developed machine learning models and infrastructure for fraud detection.


In today’s conversation, we cover his essential advice for how to integrate data science into your startup. As Ian puts it, in the early innings it might make sense for your startup to be operations heavy. But as you start to scale, data science becomes a critical component for running a business with longevity in mind. We dive into how both Square and Opendoor approached this transition.


Along those lines, we discuss some of the early considerations for your fledgling data science team, including the type of folks to hire for the early team, like whether to look for generalists or specialists, and how to set up your interview loops. Ian also dives into his lessons on structuring the data science function so that it’s deeply integrated with the rest of the technical org.


Next, we dive into some of his biggest lessons as a first-time founder and CTO, including his practice with Opendoor’s leadership team of doing pre-mortems to predict why something might not work. He also encourages founders to run through a bi-yearly exercise of re-writing their job rec.


You can follow Ian on Twitter at @ihat


You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 3997 Want to go totally asynchronous? Repeat founder Sidharth Kakkar on building a remote team & autonomous culture https://review.firstround.com/podcast/episode-62 Today’s episode is with Sidharth Kakkar, founder and CEO of Subscript, a subscription intelligence platform that empowers B2B SaaS leaders to better understand their revenue. (Read more about the company in this Techcrunch article.) Previously, he was the founder, CEO of Freckle, an education platform that grew to serve 10 million students and was acquired by Renaissance Learning in 2019. As a repeat founder, Sidharth picked up a ton of valuable lessons, particularly when it comes to company culture and management. Right from the start, he knew he wanted to build Subscript to be global, distributed, and asynchronous. That’s why there are no internal company meetings. Everyone also operates autonomously, deciding what to work on for themselves. We dive into both the philosophy behind this unique approach and the nitty gritty details of how exactly it works in practice. Here’s a preview: How to share company updates asynchronously every week. Advice on how to approach goal-setting and performance feedback, while minimizing micromanagement. Tips for improving transparency and documentation, plus details on Subscript’s running product/market fit journal.  Thoughts on how to assess asynchronous communication skills when hiring. How this culture impacts a founder’s role and schedule. There’s tons of food for thought in here, whether you’re a founder thinking about shaping your company culture, or a manager looking for some fresh ideas.  You can follow Sidharth on Twitter at @sikakkar. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Thu, 21 Jul 2022 08:00:00 -0000 full 62 First Round Subscript founder Sidharth Kakkar shares tactical advice on how to build a totally asynchronous, distributed team with no internal meetings — from increasing transparency and encouraging autonomy, to how hiring and documentation need to change. Today’s episode is with Sidharth Kakkar, founder and CEO of Subscript, a subscription intelligence platform that empowers B2B SaaS leaders to better understand their revenue. (Read more about the company in this Techcrunch article.) Previously, he was the founder, CEO of Freckle, an education platform that grew to serve 10 million students and was acquired by Renaissance Learning in 2019. As a repeat founder, Sidharth picked up a ton of valuable lessons, particularly when it comes to company culture and management. Right from the start, he knew he wanted to build Subscript to be global, distributed, and asynchronous. That’s why there are no internal company meetings. Everyone also operates autonomously, deciding what to work on for themselves. We dive into both the philosophy behind this unique approach and the nitty gritty details of how exactly it works in practice. Here’s a preview: How to share company updates asynchronously every week. Advice on how to approach goal-setting and performance feedback, while minimizing micromanagement. Tips for improving transparency and documentation, plus details on Subscript’s running product/market fit journal.  Thoughts on how to assess asynchronous communication skills when hiring. How this culture impacts a founder’s role and schedule. There’s tons of food for thought in here, whether you’re a founder thinking about shaping your company culture, or a manager looking for some fresh ideas.  You can follow Sidharth on Twitter at @sikakkar. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Today’s episode is with Sidharth Kakkar, founder and CEO of Subscript, a subscription intelligence platform that empowers B2B SaaS leaders to better understand their revenue. (Read more about the company in this Techcrunch article.)


Previously, he was the founder, CEO of Freckle, an education platform that grew to serve 10 million students and was acquired by Renaissance Learning in 2019. As a repeat founder, Sidharth picked up a ton of valuable lessons, particularly when it comes to company culture and management.


Right from the start, he knew he wanted to build Subscript to be global, distributed, and asynchronous. That’s why there are no internal company meetings. Everyone also operates autonomously, deciding what to work on for themselves.


We dive into both the philosophy behind this unique approach and the nitty gritty details of how exactly it works in practice. Here’s a preview:

  • How to share company updates asynchronously every week.
  • Advice on how to approach goal-setting and performance feedback, while minimizing micromanagement.
  • Tips for improving transparency and documentation, plus details on Subscript’s running product/market fit journal. 
  • Thoughts on how to assess asynchronous communication skills when hiring.
  • How this culture impacts a founder’s role and schedule.


There’s tons of food for thought in here, whether you’re a founder thinking about shaping your company culture, or a manager looking for some fresh ideas. 


You can follow Sidharth on Twitter at @sikakkar. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

]]> 3911 Why COO is the most fluid role in the C-Suite — Sara Clemens, former COO of Twitch & Pandora Our guest is Sara Clemens, most recently COO of Twitch and former COO of Pandora. In this interview, we explore the nuances of the COO role, which can vary drastically across different companies. We cover: The three main COO archetypes and which sorts of folks are best suited for those roles. The tactical elements of being a COO, including Sara’s advice for what good strategy actually looks like, and how to truly create a no-blame culture. Sara’s lessons on keeping pace as a company doubles in size, including her tips on sketching out “decision rights.” Guidance for CEOs considering bringing on a COO to the executive suite. You can follow Sara on Twitter at @ClemensSara You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Learn more about our sponsor, Cocoon, at meetcocooon.com Thu, 07 Jul 2022 08:00:00 -0000 full 61 First Round Sara Clemens was most recently the COO of Twitch and also previously served as the COO of Pandora. She explores the nuances of this unique C-Suite role and her advice for CEOs considering bringing aboard their first COO. Our guest is Sara Clemens, most recently COO of Twitch and former COO of Pandora. In this interview, we explore the nuances of the COO role, which can vary drastically across different companies. We cover: The three main COO archetypes and which sorts of folks are best suited for those roles. The tactical elements of being a COO, including Sara’s advice for what good strategy actually looks like, and how to truly create a no-blame culture. Sara’s lessons on keeping pace as a company doubles in size, including her tips on sketching out “decision rights.” Guidance for CEOs considering bringing on a COO to the executive suite. You can follow Sara on Twitter at @ClemensSara You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Learn more about our sponsor, Cocoon, at meetcocooon.com Our guest is Sara Clemens, most recently COO of Twitch and former COO of Pandora.


In this interview, we explore the nuances of the COO role, which can vary drastically across different companies. We cover:

  • The three main COO archetypes and which sorts of folks are best suited for those roles.
  • The tactical elements of being a COO, including Sara’s advice for what good strategy actually looks like, and how to truly create a no-blame culture.
  • Sara’s lessons on keeping pace as a company doubles in size, including her tips on sketching out “decision rights.”
  • Guidance for CEOs considering bringing on a COO to the executive suite.


You can follow Sara on Twitter at @ClemensSara


You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson


Learn more about our sponsor, Cocoon, at meetcocooon.com

]]> 3752 From PM to VP of Product: Jiaona Zhang’s career advice from Webflow, Airbnb & Dropbox https://review.firstround.com/podcast/episode-60 For our 60th episode, we’re doing things a little bit differently — with a new guest host! Welcome to Todd Jackson, who’s filling in for Brett Berson this week. Todd is also a Partner at First Round, and the episodes he hosts will mostly focus on product, given his previous product roles, from the VP of Product & Design at Dropbox and Director of Product Management at Twitter, to being a PM at Facebook and Google, leading Newsfeed and Gmail. He was also a founder — his startup Cover was backed by First Round in 2013 and later acquired by Twitter. (For more on Todd and his advice for company building, check out his article in The First Round Review from a couple years ago.) Today, Todd chats with Jiaona Zhang, the VP of Product at Webflow. (She goes by JZ though, so you’ll hear that throughout their conversation.) You might remember her popular Review article, Don’t Serve Burnt Pizza (And Other Lessons in Building Minimum Lovable Products) Before joining Webflow, JZ was the Senior Director of Product Management at WeWork, a Product Lead at Airbnb, and a PM at Dropbox and at Pocket Gems, a mobile gaming company. JZ also teaches product at Stanford and mentors a lot of rising product leaders, so she’s the perfect person to talk to about building a career in product. As the framework for the entire conversation, we start with why she doesn’t think of it as a career ladder, but rather as three distinct phases: contributing as a PM, managing PMs, and then leading the function. Here’s a preview of what Todd and JZ cover: The PM role. Advice on breaking into the function, what you should look for when you’re a candidate interviewing for PM roles, and the mistakes that are easy to make early on. The managing phase, including how to think more strategically as you get more senior, archetypes to look for when hiring, and her advice for first-time managers.  The executive phase. JZ talks about thinking of your org as a product, and she shares super tactical pointers for working with your CEO, your peers on the exec team, and the board. Whether you’re trying to break into product, grow in your career, or you’re a founder looking for hiring advice, there’s tons in this conversation for you. You can follow JZ on Twitter at @jiaonazhang. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @tjack. Thu, 23 Jun 2022 08:00:00 -0000 full 60 First Round Jiaona Zhang shares her framework for building a product career, from PM, to manager, to exec, with advice from her time at Webflow, Airbnb & Dropbox. For our 60th episode, we’re doing things a little bit differently — with a new guest host! Welcome to Todd Jackson, who’s filling in for Brett Berson this week. Todd is also a Partner at First Round, and the episodes he hosts will mostly focus on product, given his previous product roles, from the VP of Product & Design at Dropbox and Director of Product Management at Twitter, to being a PM at Facebook and Google, leading Newsfeed and Gmail. He was also a founder — his startup Cover was backed by First Round in 2013 and later acquired by Twitter. (For more on Todd and his advice for company building, check out his article in The First Round Review from a couple years ago.) Today, Todd chats with Jiaona Zhang, the VP of Product at Webflow. (She goes by JZ though, so you’ll hear that throughout their conversation.) You might remember her popular Review article, Don’t Serve Burnt Pizza (And Other Lessons in Building Minimum Lovable Products) Before joining Webflow, JZ was the Senior Director of Product Management at WeWork, a Product Lead at Airbnb, and a PM at Dropbox and at Pocket Gems, a mobile gaming company. JZ also teaches product at Stanford and mentors a lot of rising product leaders, so she’s the perfect person to talk to about building a career in product. As the framework for the entire conversation, we start with why she doesn’t think of it as a career ladder, but rather as three distinct phases: contributing as a PM, managing PMs, and then leading the function. Here’s a preview of what Todd and JZ cover: The PM role. Advice on breaking into the function, what you should look for when you’re a candidate interviewing for PM roles, and the mistakes that are easy to make early on. The managing phase, including how to think more strategically as you get more senior, archetypes to look for when hiring, and her advice for first-time managers.  The executive phase. JZ talks about thinking of your org as a product, and she shares super tactical pointers for working with your CEO, your peers on the exec team, and the board. Whether you’re trying to break into product, grow in your career, or you’re a founder looking for hiring advice, there’s tons in this conversation for you. You can follow JZ on Twitter at @jiaonazhang. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @tjack. For our 60th episode, we’re doing things a little bit differently — with a new guest host! Welcome to Todd Jackson, who’s filling in for Brett Berson this week.


Todd is also a Partner at First Round, and the episodes he hosts will mostly focus on product, given his previous product roles, from the VP of Product & Design at Dropbox and Director of Product Management at Twitter, to being a PM at Facebook and Google, leading Newsfeed and Gmail. He was also a founder — his startup Cover was backed by First Round in 2013 and later acquired by Twitter. (For more on Todd and his advice for company building, check out his article in The First Round Review from a couple years ago.)


Today, Todd chats with Jiaona Zhang, the VP of Product at Webflow. (She goes by JZ though, so you’ll hear that throughout their conversation.) You might remember her popular Review article, Don’t Serve Burnt Pizza (And Other Lessons in Building Minimum Lovable Products)


Before joining Webflow, JZ was the Senior Director of Product Management at WeWork, a Product Lead at Airbnb, and a PM at Dropbox and at Pocket Gems, a mobile gaming company. JZ also teaches product at Stanford and mentors a lot of rising product leaders, so she’s the perfect person to talk to about building a career in product.


As the framework for the entire conversation, we start with why she doesn’t think of it as a career ladder, but rather as three distinct phases: contributing as a PM, managing PMs, and then leading the function. Here’s a preview of what Todd and JZ cover:


  • The PM role. Advice on breaking into the function, what you should look for when you’re a candidate interviewing for PM roles, and the mistakes that are easy to make early on.


  • The managing phase, including how to think more strategically as you get more senior, archetypes to look for when hiring, and her advice for first-time managers. 


  • The executive phase. JZ talks about thinking of your org as a product, and she shares super tactical pointers for working with your CEO, your peers on the exec team, and the board.


Whether you’re trying to break into product, grow in your career, or you’re a founder looking for hiring advice, there’s tons in this conversation for you.


You can follow JZ on Twitter at @jiaonazhang. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @tjack.

]]> 3416 “When They Win, You Win”: Russ Laraway unpacks his new guide for the modern manager Today’s episode is with Russ Laraway, a seasoned leader who's been at Google, Twitter, Candor Inc, Qualtrics, and is now the Chief People Officer for Goodwater Capital Since we last had Russ on the show, he’s written a new book, titled: “When They Win, You Win.” On today’s episode, we dive deep into the management frameworks and original research that Russ discusses in his book. He starts by pointing out how broken our process for selecting managers is to begin with, where we often default to just promoting the highest performer on a team, rather than looking for folks who explicitly demonstrate leadership chops. He explains the raw ingredients that point to whether someone’s ready to take on a management role — even if they weren’t the best individual contributor of the bunch. And if you’re looking to hire a manager from outside of the company, he’s got plenty of interview questions to suss out the right hire. Next, we explore the heaps of research that Russ did in writing this book, and how that led to him pulling together a few specific frameworks for managers to lean on. This includes a list of the behaviors of highly-engaging managers — and how you can put these into practice. As Russ discusses in today’s interview, there are countless resources out there on how to be a better manager — often with tons of conflicting advice. Russ distills all of this down to an essential, research-backed guide for the modern manager that cuts through the noise. You can follow Russ on Twitter at @ral1. His book, “When They Win, You Win” comes out on June 7, 2022. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 26 May 2022 08:00:00 -0000 full 59 First Round Russ Laraway is a seasoned leader who's been at Google, Twitter, Candor Inc, Qualtrics, and recently joined as the Chief People Officer for Goodwater Capital. Russ unpacks the management frameworks from his new book: “When They Win, You Win” and why he believes we’re in a manager crisis. Today’s episode is with Russ Laraway, a seasoned leader who's been at Google, Twitter, Candor Inc, Qualtrics, and is now the Chief People Officer for Goodwater Capital Since we last had Russ on the show, he’s written a new book, titled: “When They Win, You Win.” On today’s episode, we dive deep into the management frameworks and original research that Russ discusses in his book. He starts by pointing out how broken our process for selecting managers is to begin with, where we often default to just promoting the highest performer on a team, rather than looking for folks who explicitly demonstrate leadership chops. He explains the raw ingredients that point to whether someone’s ready to take on a management role — even if they weren’t the best individual contributor of the bunch. And if you’re looking to hire a manager from outside of the company, he’s got plenty of interview questions to suss out the right hire. Next, we explore the heaps of research that Russ did in writing this book, and how that led to him pulling together a few specific frameworks for managers to lean on. This includes a list of the behaviors of highly-engaging managers — and how you can put these into practice. As Russ discusses in today’s interview, there are countless resources out there on how to be a better manager — often with tons of conflicting advice. Russ distills all of this down to an essential, research-backed guide for the modern manager that cuts through the noise. You can follow Russ on Twitter at @ral1. His book, “When They Win, You Win” comes out on June 7, 2022. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Today’s episode is with Russ Laraway, a seasoned leader who's been at Google, Twitter, Candor Inc, Qualtrics, and is now the Chief People Officer for Goodwater Capital


Since we last had Russ on the show, he’s written a new book, titled: “When They Win, You Win.”


On today’s episode, we dive deep into the management frameworks and original research that Russ discusses in his book. He starts by pointing out how broken our process for selecting managers is to begin with, where we often default to just promoting the highest performer on a team, rather than looking for folks who explicitly demonstrate leadership chops. He explains the raw ingredients that point to whether someone’s ready to take on a management role — even if they weren’t the best individual contributor of the bunch. And if you’re looking to hire a manager from outside of the company, he’s got plenty of interview questions to suss out the right hire.


Next, we explore the heaps of research that Russ did in writing this book, and how that led to him pulling together a few specific frameworks for managers to lean on. This includes a list of the behaviors of highly-engaging managers — and how you can put these into practice.


As Russ discusses in today’s interview, there are countless resources out there on how to be a better manager — often with tons of conflicting advice. Russ distills all of this down to an essential, research-backed guide for the modern manager that cuts through the noise.


You can follow Russ on Twitter at @ral1. His book, “When They Win, You Win” comes out on June 7, 2022.

You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 3631 Building a highly-technical enterprise product? Essential advice for product leaders — Nate Stewart of Cockroach Labs Today’s episode is with Nate Stewart, CPO of Cockroach Labs, the creator of database product CockroachDB. In today’s conversation, we cover his essential advice for building a highly-technical product. He sketches out how the Cockroach team decided on the specific use case for its database product. Nate explains the steps the team took to reach conviction on their go-forward plan — which meant saying no to a lot of customers who didn’t align with the product roadmap. Nate dives into the tactical ways to avoid taking on too many customer commitments, which he calls tech debt for product teams. Next, Nate dives into his advice for approaching design partnerships, especially when handling more conservative enterprise clients. He explains the different types of design partners, and why you should have all of those represented in the early days of your startup. Finally, we wrap up with his advice for other product leaders, including how to create a rock-solid partnership with a CEO as the first head of product, and how he solicits honest feedback across the executive team. You can follow Nate on Twitter at @Nate_Stewart You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 19 May 2022 08:00:00 -0000 full 58 First Round Nate Stewart is the Chief Product Officer of Cockroach Labs, which is the creator of CockroachDB. He unpacks the ins and outs of building a product org for a highly technical enterprise product — from crafting the product roadmap, teaming up with the right design partners, and avoiding a product strategy that fails in the real world. Today’s episode is with Nate Stewart, CPO of Cockroach Labs, the creator of database product CockroachDB. In today’s conversation, we cover his essential advice for building a highly-technical product. He sketches out how the Cockroach team decided on the specific use case for its database product. Nate explains the steps the team took to reach conviction on their go-forward plan — which meant saying no to a lot of customers who didn’t align with the product roadmap. Nate dives into the tactical ways to avoid taking on too many customer commitments, which he calls tech debt for product teams. Next, Nate dives into his advice for approaching design partnerships, especially when handling more conservative enterprise clients. He explains the different types of design partners, and why you should have all of those represented in the early days of your startup. Finally, we wrap up with his advice for other product leaders, including how to create a rock-solid partnership with a CEO as the first head of product, and how he solicits honest feedback across the executive team. You can follow Nate on Twitter at @Nate_Stewart You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Today’s episode is with Nate Stewart, CPO of Cockroach Labs, the creator of database product CockroachDB.


In today’s conversation, we cover his essential advice for building a highly-technical product. He sketches out how the Cockroach team decided on the specific use case for its database product. Nate explains the steps the team took to reach conviction on their go-forward plan — which meant saying no to a lot of customers who didn’t align with the product roadmap. Nate dives into the tactical ways to avoid taking on too many customer commitments, which he calls tech debt for product teams.


Next, Nate dives into his advice for approaching design partnerships, especially when handling more conservative enterprise clients. He explains the different types of design partners, and why you should have all of those represented in the early days of your startup.


Finally, we wrap up with his advice for other product leaders, including how to create a rock-solid partnership with a CEO as the first head of product, and how he solicits honest feedback across the executive team.


You can follow Nate on Twitter at @Nate_Stewart


You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 3488 Building & selling a product into government is tricky — Phaedra Ellis-Lamkins shares critical advice for getting it right Today’s episode is with Phaedra Ellis-Lamkins, co-founder and CEO of Promise, a modern government payment solution. In today’s conversation, Phaedra explores the ins and outs of selling a product into government. Phaedra pulls back the curtain of how she and the Promise team tackle the extra-long sales cycles, navigate layers of subcontractors, and convince risk-averse decision-makers to take a chance on a startup. We also take a step back to traverse the winding road that led to Promise in its current form. Like plenty of founders before her, Phaedra had to pivot her way into product-market fit. She explains the signals that the first iteration of the product, a bail reform platform, wasn’t going to work as she’d hoped. She then doles out lessons for other founders in the process of pivoting. You can follow Phaedra on Twitter at @phaedrael You can learn more about our advertiser Cocoon at meetcocoon.com You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 28 Apr 2022 08:00:00 -0000 full 62 First Round Phaedra Ellis-Lamkins is the co-founder and CEO of Promise, a modern government payment solution. She shares her advice for other founders building a product for government — from dealing with long sales cycles, hiring folks with industry expertise, and pivoting with purpose. Today’s episode is with Phaedra Ellis-Lamkins, co-founder and CEO of Promise, a modern government payment solution. In today’s conversation, Phaedra explores the ins and outs of selling a product into government. Phaedra pulls back the curtain of how she and the Promise team tackle the extra-long sales cycles, navigate layers of subcontractors, and convince risk-averse decision-makers to take a chance on a startup. We also take a step back to traverse the winding road that led to Promise in its current form. Like plenty of founders before her, Phaedra had to pivot her way into product-market fit. She explains the signals that the first iteration of the product, a bail reform platform, wasn’t going to work as she’d hoped. She then doles out lessons for other founders in the process of pivoting. You can follow Phaedra on Twitter at @phaedrael You can learn more about our advertiser Cocoon at meetcocoon.com You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Today’s episode is with Phaedra Ellis-Lamkins, co-founder and CEO of Promise, a modern government payment solution.

In today’s conversation, Phaedra explores the ins and outs of selling a product into government. Phaedra pulls back the curtain of how she and the Promise team tackle the extra-long sales cycles, navigate layers of subcontractors, and convince risk-averse decision-makers to take a chance on a startup.

We also take a step back to traverse the winding road that led to Promise in its current form. Like plenty of founders before her, Phaedra had to pivot her way into product-market fit. She explains the signals that the first iteration of the product, a bail reform platform, wasn’t going to work as she’d hoped. She then doles out lessons for other founders in the process of pivoting.


You can follow Phaedra on Twitter at @phaedrael

You can learn more about our advertiser Cocoon at meetcocoon.com

You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 3614 The art of starting a startup — Gagan Biyani’s advice for generating, validating, and executing on ideas https://review.firstround.com/podcast/episode-56 Today’s episode is with Gagan Biyani, co-founder and CEO of Maven, a company that empowers the world’s experts to offer cohort-based courses directly to their audience. After being early at 3 startups that achieved over $1 million in run-rate in their first six months of going live, Gagan has learned some valuable lessons and seen a wide range of outcomes — from Udemy going on to IPO in 2021, to Sprig shutting down in 2017. In our conversation, we dive deeper into the process of starting a startup. We start on generating ideas and open-ended exploration. We talk about key signals to look for in the market and the competition, as well as the mistakes he sees many aspiring founders make. Next, he recaps his concept of minimum viable tests for validating early versions of your idea. As we mention in the episode, Gagan wrote a popular article on The First Round Review last year, where he shared much more detail about his “Minimum Viable Testing Process.” Then, we dig into how you start bringing the idea to life, from exploring different potential business models, to selecting your co-founders and managing that relationship as the company grows. If you’re eager to hear even more on finding startup ideas from Gagan, he’s teaming up with The Hustle’s Sam Parr to run an Ideation Bootcamp on the Maven platform — learn more and sign up here by May 2nd if you’re interested. You can follow Gagan on Twitter at @gaganbiyani. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Thu, 21 Apr 2022 08:00:00 -0000 full 56 First Round Maven co-founder Gagan Biyani shares advice on starting a company — from generating ideas, to exploring business models and finding co-founders. Today’s episode is with Gagan Biyani, co-founder and CEO of Maven, a company that empowers the world’s experts to offer cohort-based courses directly to their audience. After being early at 3 startups that achieved over $1 million in run-rate in their first six months of going live, Gagan has learned some valuable lessons and seen a wide range of outcomes — from Udemy going on to IPO in 2021, to Sprig shutting down in 2017. In our conversation, we dive deeper into the process of starting a startup. We start on generating ideas and open-ended exploration. We talk about key signals to look for in the market and the competition, as well as the mistakes he sees many aspiring founders make. Next, he recaps his concept of minimum viable tests for validating early versions of your idea. As we mention in the episode, Gagan wrote a popular article on The First Round Review last year, where he shared much more detail about his “Minimum Viable Testing Process.” Then, we dig into how you start bringing the idea to life, from exploring different potential business models, to selecting your co-founders and managing that relationship as the company grows. If you’re eager to hear even more on finding startup ideas from Gagan, he’s teaming up with The Hustle’s Sam Parr to run an Ideation Bootcamp on the Maven platform — learn more and sign up here by May 2nd if you’re interested. You can follow Gagan on Twitter at @gaganbiyani. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Today’s episode is with Gagan Biyani, co-founder and CEO of Maven, a company that empowers the world’s experts to offer cohort-based courses directly to their audience.


After being early at 3 startups that achieved over $1 million in run-rate in their first six months of going live, Gagan has learned some valuable lessons and seen a wide range of outcomes — from Udemy going on to IPO in 2021, to Sprig shutting down in 2017.


In our conversation, we dive deeper into the process of starting a startup. We start on generating ideas and open-ended exploration. We talk about key signals to look for in the market and the competition, as well as the mistakes he sees many aspiring founders make.


Next, he recaps his concept of minimum viable tests for validating early versions of your idea. As we mention in the episode, Gagan wrote a popular article on The First Round Review last year, where he shared much more detail about his “Minimum Viable Testing Process.”


Then, we dig into how you start bringing the idea to life, from exploring different potential business models, to selecting your co-founders and managing that relationship as the company grows.


If you’re eager to hear even more on finding startup ideas from Gagan, he’s teaming up with The Hustle’s Sam Parr to run an Ideation Bootcamp on the Maven platform — learn more and sign up here by May 2nd if you’re interested.


You can follow Gagan on Twitter at @gaganbiyani. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

]]> 3754 How to handle comp challenges at every startup stage — Kaitlyn Knopp’s advice from Pequity, Instacart, Cruise & Google https://review.firstround.com/podcast/episode-55 Today’s episode is with Kaitlyn Knopp, founder and CEO of Pequity, which automates HR workflows to make compensation more equitable and scalable. Prior to starting Pequity, Kaitlyn built compensation programs and teams at companies like Instacart, Cruise, and Google — bringing a deep well of experience to this often complicated topic. We start our conversation with her advice on the traps founders need to avoid when they’re making their first hires. She sketches out a lightweight framework of how to think about comp at this early stage, from broad levels to an initial comp philosophy. We then get into the pros and cons of negotiating offers, as well as creative approaches you can bring to other aspects of comp outside of salary, such as the exercise window. Kaitlyn also shares tons of tips around how to communicate the value of equity, especially with candidates who’ve never worked at a startup before. In the back half of our conversation, we dig into the comp challenges that come up as a company starts to grow quickly. Kaitlyn shares advice on retaining existing employees through techniques like equity refreshes. We also get into the psychology of bonuses, as well as how to navigate inflation and salary adjustments. Kaitlyn shares her take on the recent trend of offering very individualized packages, and she ends on the importance of helping employees to fully understand their comp, and not shying away from topics like dilution and tax considerations. You can follow Kaitlyn on Twitter at @KaitlynKnopp. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. For more information on Cocoon, visit http://meetcocoon.com/ Thu, 14 Apr 2022 08:00:00 -0000 full 55 First Round Kaitlyn Knopp, founder & CEO of Pequity, shares tactical compensation advice for every startup stage — from initial leveling and comp philosophy, to negotiating offers, extending exercise windows, and handling bonuses and inflation adjustments. Today’s episode is with Kaitlyn Knopp, founder and CEO of Pequity, which automates HR workflows to make compensation more equitable and scalable. Prior to starting Pequity, Kaitlyn built compensation programs and teams at companies like Instacart, Cruise, and Google — bringing a deep well of experience to this often complicated topic. We start our conversation with her advice on the traps founders need to avoid when they’re making their first hires. She sketches out a lightweight framework of how to think about comp at this early stage, from broad levels to an initial comp philosophy. We then get into the pros and cons of negotiating offers, as well as creative approaches you can bring to other aspects of comp outside of salary, such as the exercise window. Kaitlyn also shares tons of tips around how to communicate the value of equity, especially with candidates who’ve never worked at a startup before. In the back half of our conversation, we dig into the comp challenges that come up as a company starts to grow quickly. Kaitlyn shares advice on retaining existing employees through techniques like equity refreshes. We also get into the psychology of bonuses, as well as how to navigate inflation and salary adjustments. Kaitlyn shares her take on the recent trend of offering very individualized packages, and she ends on the importance of helping employees to fully understand their comp, and not shying away from topics like dilution and tax considerations. You can follow Kaitlyn on Twitter at @KaitlynKnopp. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. For more information on Cocoon, visit http://meetcocoon.com/ Today’s episode is with Kaitlyn Knopp, founder and CEO of Pequity, which automates HR workflows to make compensation more equitable and scalable.


Prior to starting Pequity, Kaitlyn built compensation programs and teams at companies like Instacart, Cruise, and Google — bringing a deep well of experience to this often complicated topic.


We start our conversation with her advice on the traps founders need to avoid when they’re making their first hires. She sketches out a lightweight framework of how to think about comp at this early stage, from broad levels to an initial comp philosophy.


We then get into the pros and cons of negotiating offers, as well as creative approaches you can bring to other aspects of comp outside of salary, such as the exercise window. Kaitlyn also shares tons of tips around how to communicate the value of equity, especially with candidates who’ve never worked at a startup before.


In the back half of our conversation, we dig into the comp challenges that come up as a company starts to grow quickly. Kaitlyn shares advice on retaining existing employees through techniques like equity refreshes. We also get into the psychology of bonuses, as well as how to navigate inflation and salary adjustments.


Kaitlyn shares her take on the recent trend of offering very individualized packages, and she ends on the importance of helping employees to fully understand their comp, and not shying away from topics like dilution and tax considerations.


You can follow Kaitlyn on Twitter at @KaitlynKnopp. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.


For more information on Cocoon, visit http://meetcocoon.com/

]]> 3777 A crash course on comms for founders — Nairi Hourdajian’s early-stage advice from Figma & Uber https://review.firstround.com/podcast/episode-54 Today’s episode is with Nairi Hourdajian, the VP of Communications, Content and Community Marketing at Figma. Prior to joining Figma, Nairi was the Chief Marketing Officer at Canaan, an early-stage venture capital firm. In 2013, she became Uber’s first communications person and spent the next 3 years building out the function. Before getting into tech, Nairi came from the world of politics. She was a VP at Glover Park Group, a communications consulting firm started by former Clinton officials, and she also served as a policy director for the Democratic Senatorial Campaign Committee and as a staff assistant to then-Senator Joe Biden. Our conversation focuses on what a great communications strategy looks like at early-stage startups. Nairi breaks down the basics for founders who aren’t familiar with this function, and shares advice for thinking beyond just announcing your Series A funding. She shares lots of thoughts on crafting foundational messaging for different audiences and shaping the company narrative — with examples from both Uber and Figma, as well as startups she’s advised. Next, we get into the nuts and bolts of building relationships with reporters. Nairi shares her take on handling negative stories about your competitors, and offers tons of tactical pointers on how to prepare for a media interview. We ended on her advice for assembling the team that can help you shape and execute on your comms strategy — from working with agencies and freelancers, to making your first full-time comms hire. You can follow Nairi on Twitter at @NairiHourdaj. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Thu, 31 Mar 2022 08:00:00 -0000 full 54 First Round Nairi Hourdajian (VP of Communications at Figma & first comms hire at Uber) shares advice on how startups can get comms right, from crafting a narrative and building relationships with reporters, to working with agencies and making a full-time hire. Today’s episode is with Nairi Hourdajian, the VP of Communications, Content and Community Marketing at Figma. Prior to joining Figma, Nairi was the Chief Marketing Officer at Canaan, an early-stage venture capital firm. In 2013, she became Uber’s first communications person and spent the next 3 years building out the function. Before getting into tech, Nairi came from the world of politics. She was a VP at Glover Park Group, a communications consulting firm started by former Clinton officials, and she also served as a policy director for the Democratic Senatorial Campaign Committee and as a staff assistant to then-Senator Joe Biden. Our conversation focuses on what a great communications strategy looks like at early-stage startups. Nairi breaks down the basics for founders who aren’t familiar with this function, and shares advice for thinking beyond just announcing your Series A funding. She shares lots of thoughts on crafting foundational messaging for different audiences and shaping the company narrative — with examples from both Uber and Figma, as well as startups she’s advised. Next, we get into the nuts and bolts of building relationships with reporters. Nairi shares her take on handling negative stories about your competitors, and offers tons of tactical pointers on how to prepare for a media interview. We ended on her advice for assembling the team that can help you shape and execute on your comms strategy — from working with agencies and freelancers, to making your first full-time comms hire. You can follow Nairi on Twitter at @NairiHourdaj. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Today’s episode is with Nairi Hourdajian, the VP of Communications, Content and Community Marketing at Figma.


Prior to joining Figma, Nairi was the Chief Marketing Officer at Canaan, an early-stage venture capital firm. In 2013, she became Uber’s first communications person and spent the next 3 years building out the function. Before getting into tech, Nairi came from the world of politics. She was a VP at Glover Park Group, a communications consulting firm started by former Clinton officials, and she also served as a policy director for the Democratic Senatorial Campaign Committee and as a staff assistant to then-Senator Joe Biden.


Our conversation focuses on what a great communications strategy looks like at early-stage startups. Nairi breaks down the basics for founders who aren’t familiar with this function, and shares advice for thinking beyond just announcing your Series A funding. She shares lots of thoughts on crafting foundational messaging for different audiences and shaping the company narrative — with examples from both Uber and Figma, as well as startups she’s advised.


Next, we get into the nuts and bolts of building relationships with reporters. Nairi shares her take on handling negative stories about your competitors, and offers tons of tactical pointers on how to prepare for a media interview.


We ended on her advice for assembling the team that can help you shape and execute on your comms strategy — from working with agencies and freelancers, to making your first full-time comms hire.


You can follow Nairi on Twitter at @NairiHourdaj. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

]]> 3492 How founders can get executive hiring right from startup to scale — advice from Lattice’s Jack Altman https://review.firstround.com/podcast/episode-53 Today’s episode is with Jack Altman, co-founder & CEO of Lattice. There were so many topics we could have gotten into with Jack as it relates to scaling as a founder and CEO, but we decided to dive deep on executive hiring, a huge challenge for founders.  The conversation starts with how the hiring profile for executives changes as the company grows. Jack is a strong believer that you should focus on hiring someone who’s a great fit for the next 18-24 months, not the next 5 or 10 years. (Here's the blog post he mentioned about the different stages a CEO faces.) He also talks about the traps of hiring “too big,” whether that’s over indexing on BigCo experience, or focusing on seniority and titles that don’t match your startup’s current challenges. Instead, Jack shares more about why founders should focus on getting good at assessing and taking a chance on more junior, undiscovered talent.  Next, we dig deep into his end-to-end hiring process, from how he sources folks and what he asks in interviews, to why he sometimes does references on a candidates’ references. Whether it’s diving into how a leader might build out their team, or the red flags that signal that an executive candidate doesn’t have an ownership mentality, Jack shares tons of tactical pointers. We also get into where executive hiring errors come from, as well as the leading performance indicators to look for and what to do when a new executive leader doesn’t work out. We end by chatting about promoting internally versus hiring externally, and why you should think about your executive team like you’re constructing a portfolio. You can follow Jack on Twitter at @jaltma. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Thu, 17 Mar 2022 08:00:00 -0000 full 53 First Round Jack Altman, co-founder & CEO of Lattice, shares tactical advice for assembling your startup’s executive team — from common traps and hiring profiles, to the end-to-end process of interviewing, checking references, and evaluating performance. Today’s episode is with Jack Altman, co-founder & CEO of Lattice. There were so many topics we could have gotten into with Jack as it relates to scaling as a founder and CEO, but we decided to dive deep on executive hiring, a huge challenge for founders.  The conversation starts with how the hiring profile for executives changes as the company grows. Jack is a strong believer that you should focus on hiring someone who’s a great fit for the next 18-24 months, not the next 5 or 10 years. (Here's the blog post he mentioned about the different stages a CEO faces.) He also talks about the traps of hiring “too big,” whether that’s over indexing on BigCo experience, or focusing on seniority and titles that don’t match your startup’s current challenges. Instead, Jack shares more about why founders should focus on getting good at assessing and taking a chance on more junior, undiscovered talent.  Next, we dig deep into his end-to-end hiring process, from how he sources folks and what he asks in interviews, to why he sometimes does references on a candidates’ references. Whether it’s diving into how a leader might build out their team, or the red flags that signal that an executive candidate doesn’t have an ownership mentality, Jack shares tons of tactical pointers. We also get into where executive hiring errors come from, as well as the leading performance indicators to look for and what to do when a new executive leader doesn’t work out. We end by chatting about promoting internally versus hiring externally, and why you should think about your executive team like you’re constructing a portfolio. You can follow Jack on Twitter at @jaltma. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Today’s episode is with Jack Altman, co-founder & CEO of Lattice. There were so many topics we could have gotten into with Jack as it relates to scaling as a founder and CEO, but we decided to dive deep on executive hiring, a huge challenge for founders. 


The conversation starts with how the hiring profile for executives changes as the company grows. Jack is a strong believer that you should focus on hiring someone who’s a great fit for the next 18-24 months, not the next 5 or 10 years. (Here's the blog post he mentioned about the different stages a CEO faces.)


He also talks about the traps of hiring “too big,” whether that’s over indexing on BigCo experience, or focusing on seniority and titles that don’t match your startup’s current challenges. Instead, Jack shares more about why founders should focus on getting good at assessing and taking a chance on more junior, undiscovered talent. 


Next, we dig deep into his end-to-end hiring process, from how he sources folks and what he asks in interviews, to why he sometimes does references on a candidates’ references. Whether it’s diving into how a leader might build out their team, or the red flags that signal that an executive candidate doesn’t have an ownership mentality, Jack shares tons of tactical pointers.


We also get into where executive hiring errors come from, as well as the leading performance indicators to look for and what to do when a new executive leader doesn’t work out. We end by chatting about promoting internally versus hiring externally, and why you should think about your executive team like you’re constructing a portfolio.


You can follow Jack on Twitter at @jaltma. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

]]> 3918 IC? Manager? Technical Founder? How to chart your engineering career path — Stripe & Cocoon’s Amber Feng Today’s episode is with Amber Feng, who is the co-founder and CTO of Cocoon, and was previously an engineering leader at Stripe for eight years. In today’s conversation, we pull on threads from Amber’s engineering career to weave together lessons for other engineers charting their own path. Although Amber’s spent the majority of her career at Stripe, she’s had all sorts of different experiences — from individual contributor, to engineering manager, to heading up entire orgs, and then back to individual contributor again. We begin by discussing the unexpected traits that differentiate the most high-achieving engineers up and down the org chart. We also get into the debate that most engineers face during their career — whether to hone your craft and become an expert IC, or go the management route. Amber’s gone back and forth between the two, and shares the advice she gives to other folks who are considering where their strengths may be best leveraged. Finally, we turn the page to the most recent chapter in her career journey — becoming a first-time founder. She shares the lessons from Stripe’s Patrick Collison that she’s applying to her own company Cocoon and shares words of wisdom for other engineers with interest in starting their own company from 0 to 1. You can follow Amber on Twitter at @amfeng You can read the First Round Review article Amber mentioned with the co-founder questionnaire here: https://review.firstround.com/the-founder-dating-playbook-heres-the-process-i-used-to-find-my-co-founder You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 10 Mar 2022 09:00:00 -0000 full 52 First Round Amber Feng is the co-founder and CTO of Cocoon, and was formerly an engineering leader at Stripe for eight years. She shares her advice for other engineers wrestling with whether to take the founder, IC or management career track, and the engineering lessons from Stripe she’s bringing to her new startup. Today’s episode is with Amber Feng, who is the co-founder and CTO of Cocoon, and was previously an engineering leader at Stripe for eight years. In today’s conversation, we pull on threads from Amber’s engineering career to weave together lessons for other engineers charting their own path. Although Amber’s spent the majority of her career at Stripe, she’s had all sorts of different experiences — from individual contributor, to engineering manager, to heading up entire orgs, and then back to individual contributor again. We begin by discussing the unexpected traits that differentiate the most high-achieving engineers up and down the org chart. We also get into the debate that most engineers face during their career — whether to hone your craft and become an expert IC, or go the management route. Amber’s gone back and forth between the two, and shares the advice she gives to other folks who are considering where their strengths may be best leveraged. Finally, we turn the page to the most recent chapter in her career journey — becoming a first-time founder. She shares the lessons from Stripe’s Patrick Collison that she’s applying to her own company Cocoon and shares words of wisdom for other engineers with interest in starting their own company from 0 to 1. You can follow Amber on Twitter at @amfeng You can read the First Round Review article Amber mentioned with the co-founder questionnaire here: https://review.firstround.com/the-founder-dating-playbook-heres-the-process-i-used-to-find-my-co-founder You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Today’s episode is with Amber Feng, who is the co-founder and CTO of Cocoon, and was previously an engineering leader at Stripe for eight years.


In today’s conversation, we pull on threads from Amber’s engineering career to weave together lessons for other engineers charting their own path. Although Amber’s spent the majority of her career at Stripe, she’s had all sorts of different experiences — from individual contributor, to engineering manager, to heading up entire orgs, and then back to individual contributor again. We begin by discussing the unexpected traits that differentiate the most high-achieving engineers up and down the org chart.


We also get into the debate that most engineers face during their career — whether to hone your craft and become an expert IC, or go the management route. Amber’s gone back and forth between the two, and shares the advice she gives to other folks who are considering where their strengths may be best leveraged.


Finally, we turn the page to the most recent chapter in her career journey — becoming a first-time founder. She shares the lessons from Stripe’s Patrick Collison that she’s applying to her own company Cocoon and shares words of wisdom for other engineers with interest in starting their own company from 0 to 1.


You can follow Amber on Twitter at @amfeng


You can read the First Round Review article Amber mentioned with the co-founder questionnaire here: https://review.firstround.com/the-founder-dating-playbook-heres-the-process-i-used-to-find-my-co-founder


You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 3413 Never done sales before? Meka Asonye shares GTM playbooks from Stripe, Mixpanel, and backing founders at First Round https://review.firstround.com/podcast/episode-51 Today’s episode is with Meka Asonye, a Partner at First Round Capital. This week marks the one year anniversary since he joined, making the transition from seasoned GTM leader to full-time early-stage investor. Prior to First Round, Meka served as the VP of Sales & Services at Mixpanel, where he ran the more than 100-person global revenue team and owned the customer lifecycle from first website visit to renewal. Meka also spent four years at Stripe as it scaled from 250 to 2000 people and matured its sales org. When he first joined in 2016, he served as one of the payments company’s early account executives, leading their first attempts to go upmarket and land enterprise logos. For the next three years, he headed up Stripe’s Startup/SMB business. In today’s conversation, Meka starts by digging into his playbook for founder-led sales, from what a great first customer conversation looks like, to how to self-diagnose what went wrong. He also shares advice for founders making their first hire, including the leveling mistake that’s easy to make, and what to ask in the interview and in reference calls. He also offers thoughts on comp and the leading indicators to look for after onboarding. We then dig into structuring early pilots, from what makes for a good design partner, to how to make sure your ICP is well defined enough. We also cover helpful tactics for customer success, which Meka finds is often the most overlooked aspect of go-to-market. Throughout the conversation, we also touch on how Meka’s experiences have translated into his first year as a VC. We end on his advice for startup folks looking to transition into venture. To read more of Meka’s go-to-market advice for founders, check out his article in the First Round Review: https://review.firstround.com/this-gtm-leader-turned-investor-crowdsources-early-lessons-from-stripe-figma-and-more  You can follow Meka on Twitter at @BigMekaStyle. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Thu, 03 Mar 2022 09:00:00 -0000 full 51 First Round One year after transitioning from GTM leader at Stripe and Mixpanel to early-stage investor at First Round, Meka Asonye dives into the playbooks and sales coaching advice he shares with the technical and product oriented founders he invests in. Today’s episode is with Meka Asonye, a Partner at First Round Capital. This week marks the one year anniversary since he joined, making the transition from seasoned GTM leader to full-time early-stage investor. Prior to First Round, Meka served as the VP of Sales & Services at Mixpanel, where he ran the more than 100-person global revenue team and owned the customer lifecycle from first website visit to renewal. Meka also spent four years at Stripe as it scaled from 250 to 2000 people and matured its sales org. When he first joined in 2016, he served as one of the payments company’s early account executives, leading their first attempts to go upmarket and land enterprise logos. For the next three years, he headed up Stripe’s Startup/SMB business. In today’s conversation, Meka starts by digging into his playbook for founder-led sales, from what a great first customer conversation looks like, to how to self-diagnose what went wrong. He also shares advice for founders making their first hire, including the leveling mistake that’s easy to make, and what to ask in the interview and in reference calls. He also offers thoughts on comp and the leading indicators to look for after onboarding. We then dig into structuring early pilots, from what makes for a good design partner, to how to make sure your ICP is well defined enough. We also cover helpful tactics for customer success, which Meka finds is often the most overlooked aspect of go-to-market. Throughout the conversation, we also touch on how Meka’s experiences have translated into his first year as a VC. We end on his advice for startup folks looking to transition into venture. To read more of Meka’s go-to-market advice for founders, check out his article in the First Round Review: https://review.firstround.com/this-gtm-leader-turned-investor-crowdsources-early-lessons-from-stripe-figma-and-more  You can follow Meka on Twitter at @BigMekaStyle. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Today’s episode is with Meka Asonye, a Partner at First Round Capital. This week marks the one year anniversary since he joined, making the transition from seasoned GTM leader to full-time early-stage investor.


Prior to First Round, Meka served as the VP of Sales & Services at Mixpanel, where he ran the more than 100-person global revenue team and owned the customer lifecycle from first website visit to renewal. Meka also spent four years at Stripe as it scaled from 250 to 2000 people and matured its sales org. When he first joined in 2016, he served as one of the payments company’s early account executives, leading their first attempts to go upmarket and land enterprise logos. For the next three years, he headed up Stripe’s Startup/SMB business.


In today’s conversation, Meka starts by digging into his playbook for founder-led sales, from what a great first customer conversation looks like, to how to self-diagnose what went wrong. He also shares advice for founders making their first hire, including the leveling mistake that’s easy to make, and what to ask in the interview and in reference calls. He also offers thoughts on comp and the leading indicators to look for after onboarding.


We then dig into structuring early pilots, from what makes for a good design partner, to how to make sure your ICP is well defined enough. We also cover helpful tactics for customer success, which Meka finds is often the most overlooked aspect of go-to-market. Throughout the conversation, we also touch on how Meka’s experiences have translated into his first year as a VC. We end on his advice for startup folks looking to transition into venture.


To read more of Meka’s go-to-market advice for founders, check out his article in the First Round Review: https://review.firstround.com/this-gtm-leader-turned-investor-crowdsources-early-lessons-from-stripe-figma-and-more 


You can follow Meka on Twitter at @BigMekaStyle. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

]]> 3957 The startup playbook for expanding internationally — Advice from Faire CEO Max Rhodes https://review.firstround.com/podcast/episode-50 Today’s episode is with Max Rhodes, the co-founder and CEO of Faire, an online wholesale marketplace that connects independent retailers and brands. Prior to starting Faire in 2017, Max spent several years at Square, where he was a founding member of Square Capital, the first product manager on Square Cash, and a Director of Consumer Product for Caviar. In today’s conversation, we dive deep into how startups can get international expansion right. After launching in the U.K. and Netherlands in March 2021, Faire company expanded into countries like France, Germany, Italy and the Nordic region. They’re now in 15 markets, with over 700 employees in 10 offices around the world.  After sharing the company’s origin story and initial strategy, Max offers a helpful analogy that helped him decide when to go international, and details some lessons he learned from other companies like DoorDash and Airbnb. Next, Max takes us through the nuts and bolts of how the Faire team approached their first international launch, from staffing and operations, to how they thought about local competitors. Max also walks us through the operating cadence and strategic planning process that powered Faire’s international growth. We also talk about the human side of scaling internationally, and the growing pains that come along with it.  To help mitigate the effects, Max shares how he’s implemented the concepts from the First Round Review article on “Giving away your Legos.” Read the article here: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups  You can follow Max on Twitter at @MaxRhodesOK. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Thu, 10 Feb 2022 09:00:00 -0000 full 50 First Round Max Rhodes, co-founder & CEO of Faire, shares tactical advice for expanding internationally, from getting the timing right and facing down competition, to hiring the team, tweaking the operational cadence, and crafting the strategy to pull it off. Today’s episode is with Max Rhodes, the co-founder and CEO of Faire, an online wholesale marketplace that connects independent retailers and brands. Prior to starting Faire in 2017, Max spent several years at Square, where he was a founding member of Square Capital, the first product manager on Square Cash, and a Director of Consumer Product for Caviar. In today’s conversation, we dive deep into how startups can get international expansion right. After launching in the U.K. and Netherlands in March 2021, Faire company expanded into countries like France, Germany, Italy and the Nordic region. They’re now in 15 markets, with over 700 employees in 10 offices around the world.  After sharing the company’s origin story and initial strategy, Max offers a helpful analogy that helped him decide when to go international, and details some lessons he learned from other companies like DoorDash and Airbnb. Next, Max takes us through the nuts and bolts of how the Faire team approached their first international launch, from staffing and operations, to how they thought about local competitors. Max also walks us through the operating cadence and strategic planning process that powered Faire’s international growth. We also talk about the human side of scaling internationally, and the growing pains that come along with it.  To help mitigate the effects, Max shares how he’s implemented the concepts from the First Round Review article on “Giving away your Legos.” Read the article here: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups  You can follow Max on Twitter at @MaxRhodesOK. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Today’s episode is with Max Rhodes, the co-founder and CEO of Faire, an online wholesale marketplace that connects independent retailers and brands.


Prior to starting Faire in 2017, Max spent several years at Square, where he was a founding member of Square Capital, the first product manager on Square Cash, and a Director of Consumer Product for Caviar.


In today’s conversation, we dive deep into how startups can get international expansion right. After launching in the U.K. and Netherlands in March 2021, Faire company expanded into countries like France, Germany, Italy and the Nordic region. They’re now in 15 markets, with over 700 employees in 10 offices around the world. 


After sharing the company’s origin story and initial strategy, Max offers a helpful analogy that helped him decide when to go international, and details some lessons he learned from other companies like DoorDash and Airbnb.


Next, Max takes us through the nuts and bolts of how the Faire team approached their first international launch, from staffing and operations, to how they thought about local competitors. Max also walks us through the operating cadence and strategic planning process that powered Faire’s international growth. We also talk about the human side of scaling internationally, and the growing pains that come along with it. 


To help mitigate the effects, Max shares how he’s implemented the concepts from the First Round Review article on “Giving away your Legos.” Read the article here: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups 


You can follow Max on Twitter at @MaxRhodesOK. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

]]> 3630 Usage-based? Hybrid? Tiered? Which pricing model is right for you? — Stripe’s Jeanne DeWitt Grosser Today’s episode is with Jeanne DeWitt Grosser, Head of Americas Revenue and Growth for Stripe, where she’s responsible for all sales functions and leads the company’s enterprise strategy. She joined Stripe after a career in sales at Google and also serving as Dialpad’s Chief Revenue Officer. In today’s conversation, we dive super deep into all things pricing. To start, Jeanne outlines the trade-offs when it comes to usage-based pricing versus SaaS pricing, and how usage-based gets your company more closely aligned with the customer. She also debates the merits of hybrid or tiered pricing that Stripe has implemented and provides tips for other companies looking to go this route. Next, she explains her philosophy of treating pricing like a product, and how this shows up in Stripe’s org design. Jeanne outlines some of the pricing experiments that have had the biggest impact on how the company does business, and her tips for getting a steady drumbeat of customer feedback. To wrap up, she shares her advice for founders when it comes to treating pricing as an art and a science. If you’re in sales, or are a founder just starting to think about pricing your product, you won’t want to miss Jeanne’s insights she’s picked up over the course of her career. She’s got plenty of ideas for small startups and larger companies alike. Along the way, Jeanne provides plenty of examples from her time at Stripe to illustrate her playbook in action. You can follow Jeanne on Twitter at @jdewitt29 You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 27 Jan 2022 09:00:00 -0000 full 45 First Round In this episode with Jeanne DeWitt Grosser, Head of Americas Revenue and Growth at Stripe, we dive super deep into all things pricing — including the pros and cons of usage-based pricing, exploring hybrid pricing models, and treating pricing like a product. Today’s episode is with Jeanne DeWitt Grosser, Head of Americas Revenue and Growth for Stripe, where she’s responsible for all sales functions and leads the company’s enterprise strategy. She joined Stripe after a career in sales at Google and also serving as Dialpad’s Chief Revenue Officer. In today’s conversation, we dive super deep into all things pricing. To start, Jeanne outlines the trade-offs when it comes to usage-based pricing versus SaaS pricing, and how usage-based gets your company more closely aligned with the customer. She also debates the merits of hybrid or tiered pricing that Stripe has implemented and provides tips for other companies looking to go this route. Next, she explains her philosophy of treating pricing like a product, and how this shows up in Stripe’s org design. Jeanne outlines some of the pricing experiments that have had the biggest impact on how the company does business, and her tips for getting a steady drumbeat of customer feedback. To wrap up, she shares her advice for founders when it comes to treating pricing as an art and a science. If you’re in sales, or are a founder just starting to think about pricing your product, you won’t want to miss Jeanne’s insights she’s picked up over the course of her career. She’s got plenty of ideas for small startups and larger companies alike. Along the way, Jeanne provides plenty of examples from her time at Stripe to illustrate her playbook in action. You can follow Jeanne on Twitter at @jdewitt29 You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Today’s episode is with Jeanne DeWitt Grosser, Head of Americas Revenue and Growth for Stripe, where she’s responsible for all sales functions and leads the company’s enterprise strategy. She joined Stripe after a career in sales at Google and also serving as Dialpad’s Chief Revenue Officer.


In today’s conversation, we dive super deep into all things pricing. To start, Jeanne outlines the trade-offs when it comes to usage-based pricing versus SaaS pricing, and how usage-based gets your company more closely aligned with the customer. She also debates the merits of hybrid or tiered pricing that Stripe has implemented and provides tips for other companies looking to go this route.


Next, she explains her philosophy of treating pricing like a product, and how this shows up in Stripe’s org design. Jeanne outlines some of the pricing experiments that have had the biggest impact on how the company does business, and her tips for getting a steady drumbeat of customer feedback.


To wrap up, she shares her advice for founders when it comes to treating pricing as an art and a science. If you’re in sales, or are a founder just starting to think about pricing your product, you won’t want to miss Jeanne’s insights she’s picked up over the course of her career. She’s got plenty of ideas for small startups and larger companies alike. Along the way, Jeanne provides plenty of examples from her time at Stripe to illustrate her playbook in action.


You can follow Jeanne on Twitter at @jdewitt29


You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 2996 The Product Strategy Playbook that Powered Growth at Tinder & TripAdvisor — Ravi Mehta Today’s episode is with Ravi Mehta, who is formerly the Chief Product Officer at Tinder, and taught product strategy as an Executive in Residence at Reforge. In today’s conversation, we dive exceptionally deep into product strategy, starting with what Ravi sees as the most common disconnect between product strategy and what product teams actually work on day-to-day. In the bulk of our discussion, we walk through the core tenants of what he calls the product strategy stack, which includes the company mission, company strategy, product strategy, product roadmap, and product goals. Next, he unpacks his alternative approach to OKRs, called NCTs. He makes the case that outlining narratives, commitments, and tasks sidesteps some of the most common headaches when it comes to OKRs, and gives suggestions for implementing NCTs within your own product teams. Strategy is often misunderstood and has come to mean all sorts of different things. What struck me about Ravi is how clearly he’s able to articulate these amorphous ideas like “mission” or “vision.” He’s also got plenty of examples from his own career at TripAdvisor and Tinder, plus his work as an advisor for other fast-growing startups. You can follow Ravi on Twitter at @ravi_mehta. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 20 Jan 2022 09:00:00 -0000 full 48 First Round Ravi Mehta is the former CPO at Tinder and taught product strategy as an Executive in Residence at Reforge. He explains what he calls the product strategy stack that he developed in his career at Tinder and TripAdvisor, and his alternative approach to OKRs. Today’s episode is with Ravi Mehta, who is formerly the Chief Product Officer at Tinder, and taught product strategy as an Executive in Residence at Reforge. In today’s conversation, we dive exceptionally deep into product strategy, starting with what Ravi sees as the most common disconnect between product strategy and what product teams actually work on day-to-day. In the bulk of our discussion, we walk through the core tenants of what he calls the product strategy stack, which includes the company mission, company strategy, product strategy, product roadmap, and product goals. Next, he unpacks his alternative approach to OKRs, called NCTs. He makes the case that outlining narratives, commitments, and tasks sidesteps some of the most common headaches when it comes to OKRs, and gives suggestions for implementing NCTs within your own product teams. Strategy is often misunderstood and has come to mean all sorts of different things. What struck me about Ravi is how clearly he’s able to articulate these amorphous ideas like “mission” or “vision.” He’s also got plenty of examples from his own career at TripAdvisor and Tinder, plus his work as an advisor for other fast-growing startups. You can follow Ravi on Twitter at @ravi_mehta. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Today’s episode is with Ravi Mehta, who is formerly the Chief Product Officer at Tinder, and taught product strategy as an Executive in Residence at Reforge.


In today’s conversation, we dive exceptionally deep into product strategy, starting with what Ravi sees as the most common disconnect between product strategy and what product teams actually work on day-to-day. In the bulk of our discussion, we walk through the core tenants of what he calls the product strategy stack, which includes the company mission, company strategy, product strategy, product roadmap, and product goals.


Next, he unpacks his alternative approach to OKRs, called NCTs. He makes the case that outlining narratives, commitments, and tasks sidesteps some of the most common headaches when it comes to OKRs, and gives suggestions for implementing NCTs within your own product teams.


Strategy is often misunderstood and has come to mean all sorts of different things. What struck me about Ravi is how clearly he’s able to articulate these amorphous ideas like “mission” or “vision.” He’s also got plenty of examples from his own career at TripAdvisor and Tinder, plus his work as an advisor for other fast-growing startups.


You can follow Ravi on Twitter at @ravi_mehta.


You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 3783 After building hundreds of startup brands, Arielle Jackson shares 6 early marketing missteps to avoid https://review.firstround.com/podcast/episode-47 Today’s episode is with Arielle Jackson. For the past 7 years, she’s helped hundreds of companies build their positioning and brands from the ground up, both as our Marketing Expert in Residence here at First Round and in her own consulting work. Before helping early-stage startups, Arielle started her career in Product Marketing at Google, where she helped launch and grow Google Books and AdWords before leading marketing for Gmail. She then joined Square, where she led the launch of the Square Stand. She then headed up marketing & communications at Cover, an Android app that was acquired by Twitter. Given that she’s worked with so many companies, Arielle is a pro at spotting common patterns when it comes to early marketing, so today we spend our time digging into the challenges and missteps she’s seen so many founders run into. From category creation and company purpose, to messaging, brand personality and launch strategy, Arielle details both common pitfalls to avoid and the exercises and frameworks that she shares with founders in her consulting work. Whether it’s about not falling into the trap of focusing too much on other startup competitors, relying on emotional instead of functional benefits, or coming with unrealistic PR expectations, Arielle has tons of examples to bring these concepts to life.  If you are looking to learn more, Arielle has turned the brand strategy work she does at First Round into a cohort-based course, powered by Maven. The course runs in February and applications close on Jan 28th – find out more and apply here. Additionally, here are the resources we talked about in the episode Arielle’s First Round Review articles: - Positioning Your Startup is Vital — Here’s How to Nail It - ​​Three Moves Every Startup Founder Must Make to Build a Brand That Matters - So You Think You’re Ready to Hire a Marketer? Read This First. The books on the subject that Arielle recommends: - Positioning: The Battle for Your Mind - Play Bigger: How Rebels and Innovators Create New Categories and Dominate Markets - Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life - Predictably Irrational: The Hidden Forces That Shape Our Decisions You can follow Arielle on Twitter at @hiiamArielle. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Thu, 13 Jan 2022 09:00:00 -0000 full 47 First Round After helping to launch iconic products at Google and Square, Arielle Jackson has worked with hundreds of early-stage startups on brand strategy as First Round’s Marketer in Residence. Here are the most common early marketing mistakes that she sees. Today’s episode is with Arielle Jackson. For the past 7 years, she’s helped hundreds of companies build their positioning and brands from the ground up, both as our Marketing Expert in Residence here at First Round and in her own consulting work. Before helping early-stage startups, Arielle started her career in Product Marketing at Google, where she helped launch and grow Google Books and AdWords before leading marketing for Gmail. She then joined Square, where she led the launch of the Square Stand. She then headed up marketing & communications at Cover, an Android app that was acquired by Twitter. Given that she’s worked with so many companies, Arielle is a pro at spotting common patterns when it comes to early marketing, so today we spend our time digging into the challenges and missteps she’s seen so many founders run into. From category creation and company purpose, to messaging, brand personality and launch strategy, Arielle details both common pitfalls to avoid and the exercises and frameworks that she shares with founders in her consulting work. Whether it’s about not falling into the trap of focusing too much on other startup competitors, relying on emotional instead of functional benefits, or coming with unrealistic PR expectations, Arielle has tons of examples to bring these concepts to life.  If you are looking to learn more, Arielle has turned the brand strategy work she does at First Round into a cohort-based course, powered by Maven. The course runs in February and applications close on Jan 28th – find out more and apply here. Additionally, here are the resources we talked about in the episode Arielle’s First Round Review articles: - Positioning Your Startup is Vital — Here’s How to Nail It - ​​Three Moves Every Startup Founder Must Make to Build a Brand That Matters - So You Think You’re Ready to Hire a Marketer? Read This First. The books on the subject that Arielle recommends: - Positioning: The Battle for Your Mind - Play Bigger: How Rebels and Innovators Create New Categories and Dominate Markets - Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life - Predictably Irrational: The Hidden Forces That Shape Our Decisions You can follow Arielle on Twitter at @hiiamArielle. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Today’s episode is with Arielle Jackson. For the past 7 years, she’s helped hundreds of companies build their positioning and brands from the ground up, both as our Marketing Expert in Residence here at First Round and in her own consulting work.


Before helping early-stage startups, Arielle started her career in Product Marketing at Google, where she helped launch and grow Google Books and AdWords before leading marketing for Gmail. She then joined Square, where she led the launch of the Square Stand. She then headed up marketing & communications at Cover, an Android app that was acquired by Twitter.


Given that she’s worked with so many companies, Arielle is a pro at spotting common patterns when it comes to early marketing, so today we spend our time digging into the challenges and missteps she’s seen so many founders run into.


From category creation and company purpose, to messaging, brand personality and launch strategy, Arielle details both common pitfalls to avoid and the exercises and frameworks that she shares with founders in her consulting work.


Whether it’s about not falling into the trap of focusing too much on other startup competitors, relying on emotional instead of functional benefits, or coming with unrealistic PR expectations, Arielle has tons of examples to bring these concepts to life. 


If you are looking to learn more, Arielle has turned the brand strategy work she does at First Round into a cohort-based course, powered by Maven. The course runs in February and applications close on Jan 28th – find out more and apply here.


Additionally, here are the resources we talked about in the episode


Arielle’s First Round Review articles:

- Positioning Your Startup is Vital — Here’s How to Nail It

- ​​Three Moves Every Startup Founder Must Make to Build a Brand That Matters

- So You Think You’re Ready to Hire a Marketer? Read This First.


The books on the subject that Arielle recommends:

- Positioning: The Battle for Your Mind

- Play Bigger: How Rebels and Innovators Create New Categories and Dominate Markets

- Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life

- Predictably Irrational: The Hidden Forces That Shape Our Decisions


You can follow Arielle on Twitter at @hiiamArielle. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

]]> 5122 Buy or build? Focus on the core product or innovate? Zendesk CTO Adrian McDermott's advice for scaling https://review.firstround.com/podcast/episode-46 Today’s episode is with Adrian McDermott, CTO of Zendesk. Adrian started at the company back in 2010, when they were only 50 employees. Since then, he’s led product management and engineering teams as the company has gone public and scaled to over 5000 employees. Our discussion digs into the challenges that come from scaling startups. We start off by diving into a common decision point: whether to continue with what's working or try to make a change. Adrian goes much deeper than the “what got you here won’t get you there” advice you hear all the time in startups. Next, we cover the struggle over exploring new product areas, while still continuing to make the central product brilliant, with Adrian sharing how they use the zone to win frameworks at Zendesk. Then we dive into another classic startup dilemma: whether to build or to buy. Adrian walks us through the origin stories of several Zendesk products, from the wins to the lessons learned. In addition to sharing his perspective on the role of competition in product strategy, he also offers up his definition of a truly great product. In the back half of our conversation, Adrian shares what he’s learned leading both product and engineering teams, as well as some of the go-to-market lessons he’s picked up along the way. We end on team building and recruiting. Adrian’s interviewed more than a thousand engineers, and shares more about how he’s approached hiring at the different phases of scale at Zendesk. You can follow Adrian on Twitter at @amcdermo. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson Thu, 09 Dec 2021 09:00:00 -0000 full 46 First Round Adrian McDermott joined Zendesk in 2010, when the company had 50 employees. Now as CTO, he’s seen the team grow to over 5000. He shares his lessons on scaling, answering common startup dilemmas and offering advice for leading product and eng teams. Today’s episode is with Adrian McDermott, CTO of Zendesk. Adrian started at the company back in 2010, when they were only 50 employees. Since then, he’s led product management and engineering teams as the company has gone public and scaled to over 5000 employees. Our discussion digs into the challenges that come from scaling startups. We start off by diving into a common decision point: whether to continue with what's working or try to make a change. Adrian goes much deeper than the “what got you here won’t get you there” advice you hear all the time in startups. Next, we cover the struggle over exploring new product areas, while still continuing to make the central product brilliant, with Adrian sharing how they use the zone to win frameworks at Zendesk. Then we dive into another classic startup dilemma: whether to build or to buy. Adrian walks us through the origin stories of several Zendesk products, from the wins to the lessons learned. In addition to sharing his perspective on the role of competition in product strategy, he also offers up his definition of a truly great product. In the back half of our conversation, Adrian shares what he’s learned leading both product and engineering teams, as well as some of the go-to-market lessons he’s picked up along the way. We end on team building and recruiting. Adrian’s interviewed more than a thousand engineers, and shares more about how he’s approached hiring at the different phases of scale at Zendesk. You can follow Adrian on Twitter at @amcdermo. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson Today’s episode is with Adrian McDermott, CTO of Zendesk.


Adrian started at the company back in 2010, when they were only 50 employees. Since then, he’s led product management and engineering teams as the company has gone public and scaled to over 5000 employees.


Our discussion digs into the challenges that come from scaling startups. We start off by diving into a common decision point: whether to continue with what's working or try to make a change. Adrian goes much deeper than the “what got you here won’t get you there” advice you hear all the time in startups.


Next, we cover the struggle over exploring new product areas, while still continuing to make the central product brilliant, with Adrian sharing how they use the zone to win frameworks at Zendesk.


Then we dive into another classic startup dilemma: whether to build or to buy. Adrian walks us through the origin stories of several Zendesk products, from the wins to the lessons learned. In addition to sharing his perspective on the role of competition in product strategy, he also offers up his definition of a truly great product.


In the back half of our conversation, Adrian shares what he’s learned leading both product and engineering teams, as well as some of the go-to-market lessons he’s picked up along the way. We end on team building and recruiting. Adrian’s interviewed more than a thousand engineers, and shares more about how he’s approached hiring at the different phases of scale at Zendesk.


You can follow Adrian on Twitter at @amcdermo. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson

]]> 3585 The biggest lessons from building Hubspot, from co-founder harmony to engineering the culture — Dharmesh Shah Today’s episode is with Dharmesh Shah, the co-founder and CTO of Hubspot. In today’s conversation, we deeply explore some of the marquee moments along the 15-year journey building Hubspot. To start, Dharmesh unpacks the very specific way he and his co-founder Brian Halligan approached evaluating their compatibility as co-founders. He’s got tons of advice for other potential founding pairs to increase the likelihood of success and smoother sailing. Next, he points to some of the foundational building blocks that keep him jazzed about his role at Hubspot still to this day, including the way he elicits feedback through “bug reports.” He also explains the reasoning behind his decision to never take on any direct reports and remain an individual contributor as a co-founder. Finally, Dharmesh tells the story about how he came to own culture at Hubspot, even as the self-described least social person at the company. He walks us through how he approached culture as an engineering exercise, which continues today in his assessment of the culture as a product. You can follow Dharmesh on Twitter at @dharmesh. Thu, 02 Dec 2021 09:00:00 -0000 full 45 First Round Dharmesh Shah is the co-founder and CTO of Hubspot. He explores the 15-year journey building the company — from his partnership with co-founder Brian Halligan, choosing to never have direct reports, and treating company culture as a product. Today’s episode is with Dharmesh Shah, the co-founder and CTO of Hubspot. In today’s conversation, we deeply explore some of the marquee moments along the 15-year journey building Hubspot. To start, Dharmesh unpacks the very specific way he and his co-founder Brian Halligan approached evaluating their compatibility as co-founders. He’s got tons of advice for other potential founding pairs to increase the likelihood of success and smoother sailing. Next, he points to some of the foundational building blocks that keep him jazzed about his role at Hubspot still to this day, including the way he elicits feedback through “bug reports.” He also explains the reasoning behind his decision to never take on any direct reports and remain an individual contributor as a co-founder. Finally, Dharmesh tells the story about how he came to own culture at Hubspot, even as the self-described least social person at the company. He walks us through how he approached culture as an engineering exercise, which continues today in his assessment of the culture as a product. You can follow Dharmesh on Twitter at @dharmesh. Today’s episode is with Dharmesh Shah, the co-founder and CTO of Hubspot. In today’s conversation, we deeply explore some of the marquee moments along the 15-year journey building Hubspot. To start, Dharmesh unpacks the very specific way he and his co-founder Brian Halligan approached evaluating their compatibility as co-founders. He’s got tons of advice for other potential founding pairs to increase the likelihood of success and smoother sailing.


Next, he points to some of the foundational building blocks that keep him jazzed about his role at Hubspot still to this day, including the way he elicits feedback through “bug reports.” He also explains the reasoning behind his decision to never take on any direct reports and remain an individual contributor as a co-founder.


Finally, Dharmesh tells the story about how he came to own culture at Hubspot, even as the self-described least social person at the company. He walks us through how he approached culture as an engineering exercise, which continues today in his assessment of the culture as a product.


You can follow Dharmesh on Twitter at @dharmesh.

]]> 3226 The story of why Canva worked: Zach Kitschke shares his lessons from early hire to current CMO https://review.firstround.com/podcast/episode-44 Today’s episode is with Zach Kitschke, CMO of Canva, an online design and publishing tool. Since launching in 2013, Canva has grown from an Australian startup to a global company, with 60 million monthly active users, over 2,000 employees, and a $40 billion valuation. Zach was one of Canva's first employees, leading comms efforts around their initial launch and fundraise. But since then, he’s done everything from answering support tickets and cooking the team lunch, to serving as a product lead and spinning up the people function.  This career history gives Zach a unique vantage point on why Canva worked. The discussion starts off focused on the early days — from unpacking all the work that went into their launch, to how they improved the early product and focused on the use case for social media managers and content creators.  Next, we dig into supporting and scaling the team during hypergrowth. Canva has several unique practices around onboarding, learning and development, and keeping the team connected — from vision decks, strategy docs and a specific skills framework, to their ‘chaos to clarity’ spectrum and ‘season opener’ ritual for making company planning more fun. Zach also shares what he figured out personally along the different chapters in his career at Canva, including how to leverage advisors and when to bring someone else in to take over your role. Whether you’re a marketer, a founder, a people leader, or a product manager, there are tons of helpful takeaways for everyone in this conversation. You can follow Zach on Twitter at @zachkitschke. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Thu, 18 Nov 2021 09:00:00 -0000 full 44 First Round Zach Kitschke was an early Canva hire, and since 2013 he’s done everything from comms, support tickets and cooking team lunch, to starting the people function. Now as CMO, he shares his own career lessons and digs into why the company worked. Today’s episode is with Zach Kitschke, CMO of Canva, an online design and publishing tool. Since launching in 2013, Canva has grown from an Australian startup to a global company, with 60 million monthly active users, over 2,000 employees, and a $40 billion valuation. Zach was one of Canva's first employees, leading comms efforts around their initial launch and fundraise. But since then, he’s done everything from answering support tickets and cooking the team lunch, to serving as a product lead and spinning up the people function.  This career history gives Zach a unique vantage point on why Canva worked. The discussion starts off focused on the early days — from unpacking all the work that went into their launch, to how they improved the early product and focused on the use case for social media managers and content creators.  Next, we dig into supporting and scaling the team during hypergrowth. Canva has several unique practices around onboarding, learning and development, and keeping the team connected — from vision decks, strategy docs and a specific skills framework, to their ‘chaos to clarity’ spectrum and ‘season opener’ ritual for making company planning more fun. Zach also shares what he figured out personally along the different chapters in his career at Canva, including how to leverage advisors and when to bring someone else in to take over your role. Whether you’re a marketer, a founder, a people leader, or a product manager, there are tons of helpful takeaways for everyone in this conversation. You can follow Zach on Twitter at @zachkitschke. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Today’s episode is with Zach Kitschke, CMO of Canva, an online design and publishing tool. Since launching in 2013, Canva has grown from an Australian startup to a global company, with 60 million monthly active users, over 2,000 employees, and a $40 billion valuation.


Zach was one of Canva's first employees, leading comms efforts around their initial launch and fundraise. But since then, he’s done everything from answering support tickets and cooking the team lunch, to serving as a product lead and spinning up the people function. 


This career history gives Zach a unique vantage point on why Canva worked. The discussion starts off focused on the early days — from unpacking all the work that went into their launch, to how they improved the early product and focused on the use case for social media managers and content creators. 


Next, we dig into supporting and scaling the team during hypergrowth. Canva has several unique practices around onboarding, learning and development, and keeping the team connected — from vision decks, strategy docs and a specific skills framework, to their ‘chaos to clarity’ spectrum and ‘season opener’ ritual for making company planning more fun.


Zach also shares what he figured out personally along the different chapters in his career at Canva, including how to leverage advisors and when to bring someone else in to take over your role. Whether you’re a marketer, a founder, a people leader, or a product manager, there are tons of helpful takeaways for everyone in this conversation.


You can follow Zach on Twitter at @zachkitschke. You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

]]> 3667 Take your design org from good to great with these principles from Segment to Twilio — Hareem Mannan Today’s episode is with Hareem Mannan, who was a product design leader at Segment for nearly four years, and joined Twilio as a Senior Director of Product, Enablement & Design following the company’s acquisition of Segment. In today’s conversation, we deeply explore Hareem’s three pillars of what makes a great designer. To summarize, they are a product quality ambassador, serve as the glue across product areas, and intricately understand the go-to-market motion. We peel back the layers for each of these pillars to excavate why each is critical, and how folks can build up their skills in every pillar. Next, she takes us through her hiring loop and how she probes for core competencies in each of these three areas. Hareem also flags some of her own mistakes she’s learned from as a hiring manager. From there, she explains her favorite onboarding rituals, like unexpectedly pairing new designers with a solutions engineer, and crowd-sourcing a “Dear New Designer” document that’s become a huge hit on her team. We then turn our attention to her biggest lessons on leading a high-impact design org. She unpacks the aha moment that her fear of micromanaging had unintended consequences, and how she’s leveraged rituals like office hours and team bonding events to set a high bar for design quality. To learn more about the “Dear New Designer” onboarding document, visit Hareem’s Medium page: https://medium.com/segment-design/dear-new-designer-1fd006fc7390 You can follow Hareem on Twitter at @hareemmannan. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 11 Nov 2021 09:00:00 -0000 full 43 First Round Hareem Mannan is the Senior Director of Product, Enablement & Design at Twilio, which she joined via the company’s Segment acquisition. She explores the three pillars that set great designers apart and her top lessons on hiring, onboarding and managing a high-impact design org. Today’s episode is with Hareem Mannan, who was a product design leader at Segment for nearly four years, and joined Twilio as a Senior Director of Product, Enablement & Design following the company’s acquisition of Segment. In today’s conversation, we deeply explore Hareem’s three pillars of what makes a great designer. To summarize, they are a product quality ambassador, serve as the glue across product areas, and intricately understand the go-to-market motion. We peel back the layers for each of these pillars to excavate why each is critical, and how folks can build up their skills in every pillar. Next, she takes us through her hiring loop and how she probes for core competencies in each of these three areas. Hareem also flags some of her own mistakes she’s learned from as a hiring manager. From there, she explains her favorite onboarding rituals, like unexpectedly pairing new designers with a solutions engineer, and crowd-sourcing a “Dear New Designer” document that’s become a huge hit on her team. We then turn our attention to her biggest lessons on leading a high-impact design org. She unpacks the aha moment that her fear of micromanaging had unintended consequences, and how she’s leveraged rituals like office hours and team bonding events to set a high bar for design quality. To learn more about the “Dear New Designer” onboarding document, visit Hareem’s Medium page: https://medium.com/segment-design/dear-new-designer-1fd006fc7390 You can follow Hareem on Twitter at @hareemmannan. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Today’s episode is with Hareem Mannan, who was a product design leader at Segment for nearly four years, and joined Twilio as a Senior Director of Product, Enablement & Design following the company’s acquisition of Segment.

In today’s conversation, we deeply explore Hareem’s three pillars of what makes a great designer. To summarize, they are a product quality ambassador, serve as the glue across product areas, and intricately understand the go-to-market motion. We peel back the layers for each of these pillars to excavate why each is critical, and how folks can build up their skills in every pillar.

Next, she takes us through her hiring loop and how she probes for core competencies in each of these three areas. Hareem also flags some of her own mistakes she’s learned from as a hiring manager. From there, she explains her favorite onboarding rituals, like unexpectedly pairing new designers with a solutions engineer, and crowd-sourcing a “Dear New Designer” document that’s become a huge hit on her team.

We then turn our attention to her biggest lessons on leading a high-impact design org. She unpacks the aha moment that her fear of micromanaging had unintended consequences, and how she’s leveraged rituals like office hours and team bonding events to set a high bar for design quality.

To learn more about the “Dear New Designer” onboarding document, visit Hareem’s Medium page: https://medium.com/segment-design/dear-new-designer-1fd006fc7390

You can follow Hareem on Twitter at @hareemmannan.

You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 3844 Instacart co-founder Max Mullen gets tactical on crafting company values and intentionally building culture https://review.firstround.com/podcast/episode-42 Today’s episode is with Max Mullen, co-founder of Instacart. He started as a generalist, running everything from product to payroll, but as the company has grown over the years, he’s come to focus on one particular area: culture. Since Max is also an active angel investor, he’s also been able to partner with tons of founders and help them think about architecting their own culture at the early stages — which is exactly what we dive into in today’s episode. In the first half of our conversation, we dig into company values. Max shares both the process the Instacart team used to come up with unique values like “Every minute counts,” and his advice for making sure values actually guide behavior. He has tons of creative tactics for making employees feel more connected to them, as well as lots of helpful advice on hiring for values early on.  After getting into measuring culture and better surfacing feedback from employees, we end our conversation by chatting about some of the pitfalls when it comes to culture — the mistakes that are easy for founders to make, the factions that can develop between early employees and newcomers, and the onset of politics and bureaucracy as the company gets bigger. There’s lots of great advice here on how founders can take a more deliberate role in shaping culture from the very beginning — we hope you enjoy the episode. You can follow Max on Twitter at @Max.  You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  If you're interested in learning more about how Cocoon makes employee leave easy, visit https://www.meetcocoon.com/ Thu, 04 Nov 2021 08:00:00 -0000 full 42 First Round Max Mullen has worn many hats as a co-founder of Instacart, but he’s been uniquely focused on culture. He shares advice for crafting unique values, tips for making sure they guide day-to-day behavior, and pointers for sidestepping common mistakes. Today’s episode is with Max Mullen, co-founder of Instacart. He started as a generalist, running everything from product to payroll, but as the company has grown over the years, he’s come to focus on one particular area: culture. Since Max is also an active angel investor, he’s also been able to partner with tons of founders and help them think about architecting their own culture at the early stages — which is exactly what we dive into in today’s episode. In the first half of our conversation, we dig into company values. Max shares both the process the Instacart team used to come up with unique values like “Every minute counts,” and his advice for making sure values actually guide behavior. He has tons of creative tactics for making employees feel more connected to them, as well as lots of helpful advice on hiring for values early on.  After getting into measuring culture and better surfacing feedback from employees, we end our conversation by chatting about some of the pitfalls when it comes to culture — the mistakes that are easy for founders to make, the factions that can develop between early employees and newcomers, and the onset of politics and bureaucracy as the company gets bigger. There’s lots of great advice here on how founders can take a more deliberate role in shaping culture from the very beginning — we hope you enjoy the episode. You can follow Max on Twitter at @Max.  You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  If you're interested in learning more about how Cocoon makes employee leave easy, visit https://www.meetcocoon.com/ Today’s episode is with Max Mullen, co-founder of Instacart.


He started as a generalist, running everything from product to payroll, but as the company has grown over the years, he’s come to focus on one particular area: culture. Since Max is also an active angel investor, he’s also been able to partner with tons of founders and help them think about architecting their own culture at the early stages — which is exactly what we dive into in today’s episode.


In the first half of our conversation, we dig into company values. Max shares both the process the Instacart team used to come up with unique values like “Every minute counts,” and his advice for making sure values actually guide behavior. He has tons of creative tactics for making employees feel more connected to them, as well as lots of helpful advice on hiring for values early on. 


After getting into measuring culture and better surfacing feedback from employees, we end our conversation by chatting about some of the pitfalls when it comes to culture — the mistakes that are easy for founders to make, the factions that can develop between early employees and newcomers, and the onset of politics and bureaucracy as the company gets bigger.


There’s lots of great advice here on how founders can take a more deliberate role in shaping culture from the very beginning — we hope you enjoy the episode.


You can follow Max on Twitter at @Max. 


You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 


If you're interested in learning more about how Cocoon makes employee leave easy, visit https://www.meetcocoon.com/

]]> 3733 Growing from founder to CEO: Executive coach Alisa Cohn on how to get better feedback https://review.firstround.com/podcast/episode-41 Today’s episode is with Alisa Cohn, an executive coach with nearly 20 years of experience working with companies like Etsy, Venmo, InVision, The Wirecutter, Google and IBM. Her new book, From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business, just came out this week.  In our conversation today, we focus on what founders and startup leaders can learn from Alisa’s experiences as a coach. We start by getting into self-awareness, and how tough it can be for executives to get truly candid feedback. As an expert in the art of conducting 360 feedback, Alisa shares the right questions to ask, as well as tips for getting at the root of what people are actually saying in their feedback.  We also dive into what to do with what you hear, from why not every piece of feedback is useful, to her tips on how to actually enact change in your day-to-day routine. Next, we tackle the most common opportunities for growth that she’s seen time and time again in her coaching practice, from communication and decision-making, to how the CEO’s own personality is often unconsciously reflected in the company culture. We wrap up by covering how to have effective conversations about layering and letting people go, as well as the reflection ritual that she recommends every founder incorporate into their daily routine. This episode will be helpful for those who are making the transition from scrappy founder to established CEO, but it’s a great listen for any startup leader who’s struggling to give away their Legos. You can follow Alisa on Twitter at @AlisaCohn.  You can email us questions directly at review@firstround.com or follow us on Twitter @FirstRound and @BrettBerson. Thu, 28 Oct 2021 08:00:00 -0000 full 41 First Round Alisa Cohn has nearly 20 years of experience in executive coaching at companies like Etsy, InVision, and Google. Here, she shares advice for getting better feedback and actually enacting change on the journey from scrappy founder to seasoned CEO. Today’s episode is with Alisa Cohn, an executive coach with nearly 20 years of experience working with companies like Etsy, Venmo, InVision, The Wirecutter, Google and IBM. Her new book, From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business, just came out this week.  In our conversation today, we focus on what founders and startup leaders can learn from Alisa’s experiences as a coach. We start by getting into self-awareness, and how tough it can be for executives to get truly candid feedback. As an expert in the art of conducting 360 feedback, Alisa shares the right questions to ask, as well as tips for getting at the root of what people are actually saying in their feedback.  We also dive into what to do with what you hear, from why not every piece of feedback is useful, to her tips on how to actually enact change in your day-to-day routine. Next, we tackle the most common opportunities for growth that she’s seen time and time again in her coaching practice, from communication and decision-making, to how the CEO’s own personality is often unconsciously reflected in the company culture. We wrap up by covering how to have effective conversations about layering and letting people go, as well as the reflection ritual that she recommends every founder incorporate into their daily routine. This episode will be helpful for those who are making the transition from scrappy founder to established CEO, but it’s a great listen for any startup leader who’s struggling to give away their Legos. You can follow Alisa on Twitter at @AlisaCohn.  You can email us questions directly at review@firstround.com or follow us on Twitter @FirstRound and @BrettBerson. Today’s episode is with Alisa Cohn, an executive coach with nearly 20 years of experience working with companies like Etsy, Venmo, InVision, The Wirecutter, Google and IBM. Her new book, From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business, just came out this week. 


In our conversation today, we focus on what founders and startup leaders can learn from Alisa’s experiences as a coach. We start by getting into self-awareness, and how tough it can be for executives to get truly candid feedback. As an expert in the art of conducting 360 feedback, Alisa shares the right questions to ask, as well as tips for getting at the root of what people are actually saying in their feedback. 


We also dive into what to do with what you hear, from why not every piece of feedback is useful, to her tips on how to actually enact change in your day-to-day routine. Next, we tackle the most common opportunities for growth that she’s seen time and time again in her coaching practice, from communication and decision-making, to how the CEO’s own personality is often unconsciously reflected in the company culture.


We wrap up by covering how to have effective conversations about layering and letting people go, as well as the reflection ritual that she recommends every founder incorporate into their daily routine.


This episode will be helpful for those who are making the transition from scrappy founder to established CEO, but it’s a great listen for any startup leader who’s struggling to give away their Legos.


You can follow Alisa on Twitter at @AlisaCohn. 


You can email us questions directly at review@firstround.com or follow us on Twitter @FirstRound and @BrettBerson.

]]> 3683 Executive hiring is incredibly difficult to get right — Robinhood COO Gretchen Howard shares her playbook Today’s episode is with Gretchen Howard, COO of Robinhood. Gretchen joined Robinhood in early 2019 as the company’s COO and just its second executive hire. She climbed aboard the Robinhood rocketship after 5 years building CapitalG, Alphabet’s investment fund. In today’s conversation, we dive really deep into what she’s learned about executive hiring. To start, she explains how to align the hiring profile to the trajectory of the business to make sure you’re investing in the right places. She also unpacks her hiring philosophy as it pertains to Robinhood, including balancing financial industry expertise with an innovative, hands-on mindset that’s critical for startups. Next, she walks us through the executive interview process she’s crafted at Robinhood, including the three traits that are always at the top of her wish list for candidates — including sussing out whether someone has a “knower” versus a “learner” attitude. She also explains her complicated feelings towards certain interview exercises and how she leverages reference checks. Finally, she shares her tips for successfully onboarding new executives so these hires don’t result in what she calls “organ rejection.” If you’re struggling with your executive hiring — whether it’s coming up with the right candidate profile, aligning on culture fit, or finding that your interview process doesn’t seem to be surfacing the best candidates, this conversation is a must-listen. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Learn more about how Cocoon makes employee leave easy by visiting https://www.meetcocoon.com/ Thu, 21 Oct 2021 08:00:00 -0000 full 40 First Round Gretchen Howard is the COO of Robinhood and former Partner at CapitalG, Alphabet’s investment fund. She covers the ins and outs of building your executive team — from developing the profile and recruiting to interviewing and onboarding. Today’s episode is with Gretchen Howard, COO of Robinhood. Gretchen joined Robinhood in early 2019 as the company’s COO and just its second executive hire. She climbed aboard the Robinhood rocketship after 5 years building CapitalG, Alphabet’s investment fund. In today’s conversation, we dive really deep into what she’s learned about executive hiring. To start, she explains how to align the hiring profile to the trajectory of the business to make sure you’re investing in the right places. She also unpacks her hiring philosophy as it pertains to Robinhood, including balancing financial industry expertise with an innovative, hands-on mindset that’s critical for startups. Next, she walks us through the executive interview process she’s crafted at Robinhood, including the three traits that are always at the top of her wish list for candidates — including sussing out whether someone has a “knower” versus a “learner” attitude. She also explains her complicated feelings towards certain interview exercises and how she leverages reference checks. Finally, she shares her tips for successfully onboarding new executives so these hires don’t result in what she calls “organ rejection.” If you’re struggling with your executive hiring — whether it’s coming up with the right candidate profile, aligning on culture fit, or finding that your interview process doesn’t seem to be surfacing the best candidates, this conversation is a must-listen. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Learn more about how Cocoon makes employee leave easy by visiting https://www.meetcocoon.com/ Today’s episode is with Gretchen Howard, COO of Robinhood. Gretchen joined Robinhood in early 2019 as the company’s COO and just its second executive hire. She climbed aboard the Robinhood rocketship after 5 years building CapitalG, Alphabet’s investment fund.


In today’s conversation, we dive really deep into what she’s learned about executive hiring. To start, she explains how to align the hiring profile to the trajectory of the business to make sure you’re investing in the right places. She also unpacks her hiring philosophy as it pertains to Robinhood, including balancing financial industry expertise with an innovative, hands-on mindset that’s critical for startups.


Next, she walks us through the executive interview process she’s crafted at Robinhood, including the three traits that are always at the top of her wish list for candidates — including sussing out whether someone has a “knower” versus a “learner” attitude. She also explains her complicated feelings towards certain interview exercises and how she leverages reference checks. Finally, she shares her tips for successfully onboarding new executives so these hires don’t result in what she calls “organ rejection.”


If you’re struggling with your executive hiring — whether it’s coming up with the right candidate profile, aligning on culture fit, or finding that your interview process doesn’t seem to be surfacing the best candidates, this conversation is a must-listen.

You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson


Learn more about how Cocoon makes employee leave easy by visiting https://www.meetcocoon.com/

]]> 3605 Building a hybrid go-to-market motion — GC Lionetti’s lessons from Confluent, Dropbox & Atlassian https://review.firstround.com/podcast/episode-39 Today’s episode is with Giancarlo 'GC' Lionetti, the former CMO of Confluent and VP of Self-Serve Growth at Dropbox. (GC also previously spent 6 years at Atlassian, as a sales engineer and product marketing manager for developer tools.) He describes his career as more of a maze than a ladder, and this functional diversity combined with his deep experience at standout B2B companies gives him a unique perspective. In today’s conversation, we dig deep into why he advocates for a hybrid go-to-market strategy that brings together more traditional selling with modern product-led growth. We start by mining lessons from GC’s time at Atlassian and Dropbox, including his takes on the differences between their business models and what it takes to make a multi-product go-to-market motion work. Then we dive right into his advice for a hybrid approach, covering everything from his litmus tests for picking the right metrics, to the structure of his weekly meetings. GC explains how he sinks tons of time into understanding the customer journey, mapping out the delta between reality and the ideal vision.  He also shares plenty of pro-tips about pricing, packaging, and activation, as well as a broader diagnostic framework that he’s developed to evaluate a company’s go-to-market strategy. We wrap up by focusing on team building for a hybrid go-to-market strategy — from hiring profiles to team structure. It’s a great listen for founders, product and go-to-market leaders, with tons of examples of specific impactful experiments he ran, metrics that did or didn’t work out, and common traps that he sees teams falling into.  You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Thu, 07 Oct 2021 08:00:00 -0000 full 36 First Round Giancarlo ‘GC’ Lionetti has been the CMO of Confluent, a VP of Growth at Dropbox, and sales engineer and product marketing manager at Atlassian. He digs into building hybrid go-to-market motions that combine product-led growth and traditional sales. Today’s episode is with Giancarlo 'GC' Lionetti, the former CMO of Confluent and VP of Self-Serve Growth at Dropbox. (GC also previously spent 6 years at Atlassian, as a sales engineer and product marketing manager for developer tools.) He describes his career as more of a maze than a ladder, and this functional diversity combined with his deep experience at standout B2B companies gives him a unique perspective. In today’s conversation, we dig deep into why he advocates for a hybrid go-to-market strategy that brings together more traditional selling with modern product-led growth. We start by mining lessons from GC’s time at Atlassian and Dropbox, including his takes on the differences between their business models and what it takes to make a multi-product go-to-market motion work. Then we dive right into his advice for a hybrid approach, covering everything from his litmus tests for picking the right metrics, to the structure of his weekly meetings. GC explains how he sinks tons of time into understanding the customer journey, mapping out the delta between reality and the ideal vision.  He also shares plenty of pro-tips about pricing, packaging, and activation, as well as a broader diagnostic framework that he’s developed to evaluate a company’s go-to-market strategy. We wrap up by focusing on team building for a hybrid go-to-market strategy — from hiring profiles to team structure. It’s a great listen for founders, product and go-to-market leaders, with tons of examples of specific impactful experiments he ran, metrics that did or didn’t work out, and common traps that he sees teams falling into.  You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Today’s episode is with Giancarlo 'GC' Lionetti, the former CMO of Confluent and VP of Self-Serve Growth at Dropbox. (GC also previously spent 6 years at Atlassian, as a sales engineer and product marketing manager for developer tools.)

He describes his career as more of a maze than a ladder, and this functional diversity combined with his deep experience at standout B2B companies gives him a unique perspective. In today’s conversation, we dig deep into why he advocates for a hybrid go-to-market strategy that brings together more traditional selling with modern product-led growth.

We start by mining lessons from GC’s time at Atlassian and Dropbox, including his takes on the differences between their business models and what it takes to make a multi-product go-to-market motion work.

Then we dive right into his advice for a hybrid approach, covering everything from his litmus tests for picking the right metrics, to the structure of his weekly meetings. GC explains how he sinks tons of time into understanding the customer journey, mapping out the delta between reality and the ideal vision. 

He also shares plenty of pro-tips about pricing, packaging, and activation, as well as a broader diagnostic framework that he’s developed to evaluate a company’s go-to-market strategy. We wrap up by focusing on team building for a hybrid go-to-market strategy — from hiring profiles to team structure.

It’s a great listen for founders, product and go-to-market leaders, with tons of examples of specific impactful experiments he ran, metrics that did or didn’t work out, and common traps that he sees teams falling into. 

You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

]]> 3965 Creating physical products and getting feedback from toddlers — KiwiCo’s Sandra Oh Lin https://traffic.libsyn.com/secure/firstround/EP.38_-_Sandra_Oh_Lin_FINAL.mp3 Today’s episode is with Sandr Oh Lin, founder and CEO of KiwiCo, which creates hands-on learning kits for children. Sandra started KiwiCo over ten years ago, after a career with executive positions at PayPal and eBay. She was looking for ways to give her own kids more hands-on projects to exercise their creativity, which led her down the path to become an entrepreneur and create KiwiCo. Today, KiwiCo has expanded to include 8 different lines of crates that are shipped out monthly. In the first half of today’s conversation, we excavate some of the thornier challenges that come with creating a physical product — and Sandra’s biggest aha moments as a first-time founder. She talks about creating the first KiwiCo crate, including the product development process and spinning up a supply chain and shipping department. Sandra also walks us through how KiwiCo approaches new product lines, particularly in the last year when KiwiCo demand skyrocketed. She also discusses how the team gathers quality consumer feedback when your customer is often a toddler. In the second half of our interview, she talks about some of the cultural practices at KiwiCo that all sorts of companies can learn from. Sandra’s a big believer in manager training for everyone from folks that manage just one person, to executives that have been managing for decades. She outlines the specific management training modules they leverage at KiwiCo and makes the case for having everyone at the company fill out a motivations spreadsheet. Finally, she discusses the specific tactics she leans on for creating a feedback-rich environment for herself as a CEO. You can follow Sandra on Twitter at @sandraohlin. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 30 Sep 2021 08:00:00 -0000 full 38 First Round Sandra Oh Lin is the founder and CEO of KiwiCo, which creates hands-on learning kits for children. We discuss how Sandra tackled the early obstacles in creating a physical product — from the design process, production, and consumer testing when your cus Today’s episode is with Sandr Oh Lin, founder and CEO of KiwiCo, which creates hands-on learning kits for children. Sandra started KiwiCo over ten years ago, after a career with executive positions at PayPal and eBay. She was looking for ways to give her own kids more hands-on projects to exercise their creativity, which led her down the path to become an entrepreneur and create KiwiCo. Today, KiwiCo has expanded to include 8 different lines of crates that are shipped out monthly. In the first half of today’s conversation, we excavate some of the thornier challenges that come with creating a physical product — and Sandra’s biggest aha moments as a first-time founder. She talks about creating the first KiwiCo crate, including the product development process and spinning up a supply chain and shipping department. Sandra also walks us through how KiwiCo approaches new product lines, particularly in the last year when KiwiCo demand skyrocketed. She also discusses how the team gathers quality consumer feedback when your customer is often a toddler. In the second half of our interview, she talks about some of the cultural practices at KiwiCo that all sorts of companies can learn from. Sandra’s a big believer in manager training for everyone from folks that manage just one person, to executives that have been managing for decades. She outlines the specific management training modules they leverage at KiwiCo and makes the case for having everyone at the company fill out a motivations spreadsheet. Finally, she discusses the specific tactics she leans on for creating a feedback-rich environment for herself as a CEO. You can follow Sandra on Twitter at @sandraohlin. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Today’s episode is with Sandr Oh Lin, founder and CEO of KiwiCo, which creates hands-on learning kits for children. Sandra started KiwiCo over ten years ago, after a career with executive positions at PayPal and eBay. She was looking for ways to give her own kids more hands-on projects to exercise their creativity, which led her down the path to become an entrepreneur and create KiwiCo. Today, KiwiCo has expanded to include 8 different lines of crates that are shipped out monthly.

In the first half of today’s conversation, we excavate some of the thornier challenges that come with creating a physical product — and Sandra’s biggest aha moments as a first-time founder. She talks about creating the first KiwiCo crate, including the product development process and spinning up a supply chain and shipping department. Sandra also walks us through how KiwiCo approaches new product lines, particularly in the last year when KiwiCo demand skyrocketed. She also discusses how the team gathers quality consumer feedback when your customer is often a toddler.

In the second half of our interview, she talks about some of the cultural practices at KiwiCo that all sorts of companies can learn from. Sandra’s a big believer in manager training for everyone from folks that manage just one person, to executives that have been managing for decades. She outlines the specific management training modules they leverage at KiwiCo and makes the case for having everyone at the company fill out a motivations spreadsheet. Finally, she discusses the specific tactics she leans on for creating a feedback-rich environment for herself as a CEO.

You can follow Sandra on Twitter at @sandraohlin.

You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 3490 no How to hire the right marketer at the right time for your startup — Mux & Segment’s Maya Spivak https://traffic.libsyn.com/secure/firstround/EP.37_-_Maya_Spivak_FINAL.mp3 Today’s episode is with Maya Spivak, the Head of Marketing at Mux, which is ​​an API for developers to build video experiences. Maya recently joined Mux after five years at Segment, where she was the company’s second marketer and its Head of Global Brand Marketing and Communications, as well as a stint at Wealthfront as a marketing director. In today’s conversation, she takes a magnifying glass to the core components of a startup’s marketing org. She starts by breaking down the three pillars of marketing roles — product, brand, and growth. She explains the leading indicators that your startup is ready to hire folks within each of these pillars — which starts with analyzing your sales motion and sizing up the founders’ strengths and weaknesses. Next, Maya pulls back the curtain on how she architects interview loops for each of these different roles, and the unique capabilities that separate good candidates from great, must-hire folks. Finally, she reflects on her experience as one of the earliest marketing hires at Segment, and how she built the marketing org in the first couple of years to keep up with the shifting needs of the growing startup. Today’s conversation is of course a must-listen for marketers, particularly marketing leaders and hiring managers that are trying to pluck out the best and the brightest to join their org. But there’s a ton for other folks to learn from this interview, which explains some of the nuances of startup marketing you may not fully appreciate. You can follow Maya on Twitter at @papayamaya. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 16 Sep 2021 08:00:00 -0000 full 37 First Round Maya Spivak is the Head of Marketing at Mux and former Head of Global Brand Marketing & Comms at Segment. She explains the three core pillars of the marketing org (product, brand and growth), how to know which one is right for your startup stage, and tips Today’s episode is with Maya Spivak, the Head of Marketing at Mux, which is ​​an API for developers to build video experiences. Maya recently joined Mux after five years at Segment, where she was the company’s second marketer and its Head of Global Brand Marketing and Communications, as well as a stint at Wealthfront as a marketing director. In today’s conversation, she takes a magnifying glass to the core components of a startup’s marketing org. She starts by breaking down the three pillars of marketing roles — product, brand, and growth. She explains the leading indicators that your startup is ready to hire folks within each of these pillars — which starts with analyzing your sales motion and sizing up the founders’ strengths and weaknesses. Next, Maya pulls back the curtain on how she architects interview loops for each of these different roles, and the unique capabilities that separate good candidates from great, must-hire folks. Finally, she reflects on her experience as one of the earliest marketing hires at Segment, and how she built the marketing org in the first couple of years to keep up with the shifting needs of the growing startup. Today’s conversation is of course a must-listen for marketers, particularly marketing leaders and hiring managers that are trying to pluck out the best and the brightest to join their org. But there’s a ton for other folks to learn from this interview, which explains some of the nuances of startup marketing you may not fully appreciate. You can follow Maya on Twitter at @papayamaya. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Today’s episode is with Maya Spivak, the Head of Marketing at Mux, which is ​​an API for developers to build video experiences. Maya recently joined Mux after five years at Segment, where she was the company’s second marketer and its Head of Global Brand Marketing and Communications, as well as a stint at Wealthfront as a marketing director.

In today’s conversation, she takes a magnifying glass to the core components of a startup’s marketing org. She starts by breaking down the three pillars of marketing roles — product, brand, and growth. She explains the leading indicators that your startup is ready to hire folks within each of these pillars — which starts with analyzing your sales motion and sizing up the founders’ strengths and weaknesses.

Next, Maya pulls back the curtain on how she architects interview loops for each of these different roles, and the unique capabilities that separate good candidates from great, must-hire folks. Finally, she reflects on her experience as one of the earliest marketing hires at Segment, and how she built the marketing org in the first couple of years to keep up with the shifting needs of the growing startup.

Today’s conversation is of course a must-listen for marketers, particularly marketing leaders and hiring managers that are trying to pluck out the best and the brightest to join their org. But there’s a ton for other folks to learn from this interview, which explains some of the nuances of startup marketing you may not fully appreciate.

You can follow Maya on Twitter at @papayamaya.

You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 3412 no From developer to CMO — Archana Agrawal’s marketing lessons from Airtable & Atlassian https://traffic.libsyn.com/secure/firstround/EP.36_-_Archana_Agrawal_FINAL.mp3 Today’s episode is with Archana Agrawal, CMO of Airtable, a low-code platform for building collaborative apps. Archana joined Airtable last year after 7 years at Atlassian, where she eventually became the company’s Head of Enterprise and Cloud Marketing. She also sits on the board for MongoDB and Zendesk. We start today’s conversation by dissecting some of the messaging challenges facing horizontal products like both Airtable and Atlassian, and her tips for narrowing in on the right persona. She also dives into the close interplay between product and marketing teams, particularly for product-led growth companies. Throughout our conversation, we talk a lot about organizational design, and how to set your teams up for breaking down siloes and fostering experimentation. She explains how she oversees all the different marketing functions that report up to her as CMO, and the rituals she’s established for keeping the pulse on what most deserves her attention. Today’s conversation is of course a must-listen for marketers, but folks all over the org chart at product-led growth companies will appreciate the insights from both Atlassian and Airtable. As a former engineer-turned-marketer, Archana has an incredibly unique, data-driven perspective as a CMO. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 09 Sep 2021 08:00:00 -0000 full 36 First Round Archana Agrawal is CMO of Airtable and former Head of Enterprise and Cloud Marketing for Atlassian. She shares her biggest marketing lessons from the two product-led growth companies, including developing the right personas and strategic org design. Today’s episode is with Archana Agrawal, CMO of Airtable, a low-code platform for building collaborative apps. Archana joined Airtable last year after 7 years at Atlassian, where she eventually became the company’s Head of Enterprise and Cloud Marketing. She also sits on the board for MongoDB and Zendesk. We start today’s conversation by dissecting some of the messaging challenges facing horizontal products like both Airtable and Atlassian, and her tips for narrowing in on the right persona. She also dives into the close interplay between product and marketing teams, particularly for product-led growth companies. Throughout our conversation, we talk a lot about organizational design, and how to set your teams up for breaking down siloes and fostering experimentation. She explains how she oversees all the different marketing functions that report up to her as CMO, and the rituals she’s established for keeping the pulse on what most deserves her attention. Today’s conversation is of course a must-listen for marketers, but folks all over the org chart at product-led growth companies will appreciate the insights from both Atlassian and Airtable. As a former engineer-turned-marketer, Archana has an incredibly unique, data-driven perspective as a CMO. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Today’s episode is with Archana Agrawal, CMO of Airtable, a low-code platform for building collaborative apps. Archana joined Airtable last year after 7 years at Atlassian, where she eventually became the company’s Head of Enterprise and Cloud Marketing. She also sits on the board for MongoDB and Zendesk.

We start today’s conversation by dissecting some of the messaging challenges facing horizontal products like both Airtable and Atlassian, and her tips for narrowing in on the right persona. She also dives into the close interplay between product and marketing teams, particularly for product-led growth companies.

Throughout our conversation, we talk a lot about organizational design, and how to set your teams up for breaking down siloes and fostering experimentation. She explains how she oversees all the different marketing functions that report up to her as CMO, and the rituals she’s established for keeping the pulse on what most deserves her attention.

Today’s conversation is of course a must-listen for marketers, but folks all over the org chart at product-led growth companies will appreciate the insights from both Atlassian and Airtable. As a former engineer-turned-marketer, Archana has an incredibly unique, data-driven perspective as a CMO.

You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 3379 no How to pivot your way to product/market fit & other 0-1 lessons — Rupa Health CEO Tara Viswanathan https://review.firstround.com/podcast/episode-35 Today’s episode is with Tara Viswanathan, co-founder and CEO of Rupa Health. Tara started Rupa Health in early 2018, but the product vision today looks very different from what she first built. As she’ll talk about over the course of today’s interview, she went through plenty of sometimes painful pivots on the path to finding product/market fit for Rupa. Tara is incredibly candid about all of the things she had to learn the hard way as a first-time founder going from zero to one. For the first half of our interview, we pay particular attention to her lessons in finding the elusive startup holy grail of product/market fit. We cover the aha moment that the first iteration of the product wasn’t going to work, and why she thinks hiring a few folks before finding product/market fit was one of her earliest mistakes. We then dive into her decision to create a new product knowing that it wasn’t going to be the thing that ultimately worked — but was bullish that it would lead down the right path. In the second half of our interview, she talks about hiring Rupa’s early team, and her tactics that go against the grain of conventional startup wisdom. For starters, she leaned heavily on external contractors rather than full-time employees on the path to product/market fit — and she thinks more founders should consider doing the same. She also dives into why she hates job descriptions, and what she prescribes instead. As a founder still in the trenches, Tara is game to get super tactical about the things she’s tried along Rupa’s winding journey that did and didn’t work. It’s a must-listen for other founders — or anyone that’s got a burning curiosity about what it’s actually like to be an entrepreneur. You can follow Tara on Twitter at @taraviswanathan. To learn more about the “who” interview, check out the book “Who: The A Method for Hiring.” Be sure to check out the recent coverage of Rupa Health in Forbes. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 02 Sep 2021 08:00:00 -0000 full 35 First Round In this episode with first-time founder Tara Viswanathan, co-founder and CEO of Rupa Health, we cover her biggest lessons on finding product/market fit and hiring the early team. Today’s episode is with Tara Viswanathan, co-founder and CEO of Rupa Health. Tara started Rupa Health in early 2018, but the product vision today looks very different from what she first built. As she’ll talk about over the course of today’s interview, she went through plenty of sometimes painful pivots on the path to finding product/market fit for Rupa. Tara is incredibly candid about all of the things she had to learn the hard way as a first-time founder going from zero to one. For the first half of our interview, we pay particular attention to her lessons in finding the elusive startup holy grail of product/market fit. We cover the aha moment that the first iteration of the product wasn’t going to work, and why she thinks hiring a few folks before finding product/market fit was one of her earliest mistakes. We then dive into her decision to create a new product knowing that it wasn’t going to be the thing that ultimately worked — but was bullish that it would lead down the right path. In the second half of our interview, she talks about hiring Rupa’s early team, and her tactics that go against the grain of conventional startup wisdom. For starters, she leaned heavily on external contractors rather than full-time employees on the path to product/market fit — and she thinks more founders should consider doing the same. She also dives into why she hates job descriptions, and what she prescribes instead. As a founder still in the trenches, Tara is game to get super tactical about the things she’s tried along Rupa’s winding journey that did and didn’t work. It’s a must-listen for other founders — or anyone that’s got a burning curiosity about what it’s actually like to be an entrepreneur. You can follow Tara on Twitter at @taraviswanathan. To learn more about the “who” interview, check out the book “Who: The A Method for Hiring.” Be sure to check out the recent coverage of Rupa Health in Forbes. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Today’s episode is with Tara Viswanathan, co-founder and CEO of Rupa Health. Tara started Rupa Health in early 2018, but the product vision today looks very different from what she first built. As she’ll talk about over the course of today’s interview, she went through plenty of sometimes painful pivots on the path to finding product/market fit for Rupa.

Tara is incredibly candid about all of the things she had to learn the hard way as a first-time founder going from zero to one. For the first half of our interview, we pay particular attention to her lessons in finding the elusive startup holy grail of product/market fit.

We cover the aha moment that the first iteration of the product wasn’t going to work, and why she thinks hiring a few folks before finding product/market fit was one of her earliest mistakes. We then dive into her decision to create a new product knowing that it wasn’t going to be the thing that ultimately worked — but was bullish that it would lead down the right path.

In the second half of our interview, she talks about hiring Rupa’s early team, and her tactics that go against the grain of conventional startup wisdom. For starters, she leaned heavily on external contractors rather than full-time employees on the path to product/market fit — and she thinks more founders should consider doing the same. She also dives into why she hates job descriptions, and what she prescribes instead.

As a founder still in the trenches, Tara is game to get super tactical about the things she’s tried along Rupa’s winding journey that did and didn’t work. It’s a must-listen for other founders — or anyone that’s got a burning curiosity about what it’s actually like to be an entrepreneur.

You can follow Tara on Twitter at @taraviswanathan.

To learn more about the “who” interview, check out the book “Who: The A Method for Hiring.”

Be sure to check out the recent coverage of Rupa Health in Forbes.

You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 3441 no Building an operationally-intensive business and avoiding upside down unit economics  — Thirty Madison’s Steve Gutentag https://review.firstround.com/podcast/episode-34 Today’s episode is with Steve Gutentag, the co-founder and CEO of Thirty Madison, a healthcare company focused on widening access to specialized care for chronic conditions.  After previously starting two other companies with his co-founder Demetri Karagas, they launched Thirty Madison in 2017 with Keeps, a men’s hair loss solution. The team has since gone on to launch several new brands, including Cove (for migraines), Evens (for GI issues), and Picnic (for allergies). With the acceleration in telemedicine due to COVID-19, the company has tripled both their revenue and their team size in the past year, recently announcing $140M in Series C funding and a more than $1B evaluation. We start our conversation by getting into the challenges of building an operationally complex business with a physical or real-world component. Steve shares the lessons he learned from building his first two startups, and figuring out what he was uniquely suited to build. He also shares why they wanted to pick a business that worked with unit economics on day one, walking us through their methodical approach to figuring out if the idea for Thirty Madison would. From their conservative assumptions for each line item, to the unlocks that came from more inventive moves, Steve shares tons of pointers here — including why you should think of your own internal operations as a marketplace, and how unit economics won’t magically fix themselves at scale. In the last part of our conversation, we get into building the team that’s pulling all of this complex work off. We talked about when to hire for industry experience versus a fresh perspective, as well as more granular hiring tactics such as the interview questions he asks to learn about a candidate’s journey as a manager. You can follow Steve on Twitter @stevengoodday, and you can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Thu, 19 Aug 2021 08:00:00 -0000 full 34 First Round Steve Gutentag shares the lessons he’s learned building three startups, including how to figure out if there’s founder/product fit and how to build an operationally complex business with unit economics that work from day one. Today’s episode is with Steve Gutentag, the co-founder and CEO of Thirty Madison, a healthcare company focused on widening access to specialized care for chronic conditions.  After previously starting two other companies with his co-founder Demetri Karagas, they launched Thirty Madison in 2017 with Keeps, a men’s hair loss solution. The team has since gone on to launch several new brands, including Cove (for migraines), Evens (for GI issues), and Picnic (for allergies). With the acceleration in telemedicine due to COVID-19, the company has tripled both their revenue and their team size in the past year, recently announcing $140M in Series C funding and a more than $1B evaluation. We start our conversation by getting into the challenges of building an operationally complex business with a physical or real-world component. Steve shares the lessons he learned from building his first two startups, and figuring out what he was uniquely suited to build. He also shares why they wanted to pick a business that worked with unit economics on day one, walking us through their methodical approach to figuring out if the idea for Thirty Madison would. From their conservative assumptions for each line item, to the unlocks that came from more inventive moves, Steve shares tons of pointers here — including why you should think of your own internal operations as a marketplace, and how unit economics won’t magically fix themselves at scale. In the last part of our conversation, we get into building the team that’s pulling all of this complex work off. We talked about when to hire for industry experience versus a fresh perspective, as well as more granular hiring tactics such as the interview questions he asks to learn about a candidate’s journey as a manager. You can follow Steve on Twitter @stevengoodday, and you can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. Today’s episode is with Steve Gutentag, the co-founder and CEO of Thirty Madison, a healthcare company focused on widening access to specialized care for chronic conditions. 

After previously starting two other companies with his co-founder Demetri Karagas, they launched Thirty Madison in 2017 with Keeps, a men’s hair loss solution. The team has since gone on to launch several new brands, including Cove (for migraines), Evens (for GI issues), and Picnic (for allergies). With the acceleration in telemedicine due to COVID-19, the company has tripled both their revenue and their team size in the past year, recently announcing $140M in Series C funding and a more than $1B evaluation.

We start our conversation by getting into the challenges of building an operationally complex business with a physical or real-world component. Steve shares the lessons he learned from building his first two startups, and figuring out what he was uniquely suited to build.

He also shares why they wanted to pick a business that worked with unit economics on day one, walking us through their methodical approach to figuring out if the idea for Thirty Madison would. From their conservative assumptions for each line item, to the unlocks that came from more inventive moves, Steve shares tons of pointers here — including why you should think of your own internal operations as a marketplace, and how unit economics won’t magically fix themselves at scale.

In the last part of our conversation, we get into building the team that’s pulling all of this complex work off. We talked about when to hire for industry experience versus a fresh perspective, as well as more granular hiring tactics such as the interview questions he asks to learn about a candidate’s journey as a manager.

You can follow Steve on Twitter @stevengoodday, and you can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.

]]> 3596 no Don’t have a UX research team? Jane Davis’ tips from Zoom, Zapier & Dropbox to get you started https://review.firstround.com/podcast/episode-33 Today’s episode is with Jane Davis, the Director of UX Research and UX Writing at Zoom. She previously led UX Research and Content Design at Zapier, and managed the growth research team at Dropbox. Throughout the episode, Jane tackles the thorniest customer development questions and walks us through the end-to-end research process in incredible detail, covering everything from clarifying your goals and asking the right questions, to selecting participants and synthesizing insights.     We start by going through how she applies her playbook in the early-stage startup context — when you’re shipping the first version of your product and don’t yet have the resources to invest in a full research team. We also dig into challenges such as deeply understanding the problem you’re solving, taking on a competitive or a greenfield market, and figuring out willingness to pay. We also get into best practices for prototyping and iterating, as well as some of the common roadblocks startups face later on, including how to build for multiple users and what to do when people aren’t excited about your product or using it frequently. Whether you’re talking to potential customers before you start a company, or are looking to get better feedback from your current users, there’s tons of insights in here for founders, product-builders, and design folks alike. Here’s the book Jane mentioned in the episode: Just Enough Research by Erica Hall. We also recommend checking out Jane’s recent article: What’s the point of a UX research team? You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Thu, 12 Aug 2021 08:00:00 -0000 full 33 First Round Jane Davis shares the playbooks she’s honed leading user research teams at Zoom, Zapier and Dropbox, tackling everything from specific questions to ask in customer interviews, to frameworks for getting feedback as you launch and prototype products. Today’s episode is with Jane Davis, the Director of UX Research and UX Writing at Zoom. She previously led UX Research and Content Design at Zapier, and managed the growth research team at Dropbox. Throughout the episode, Jane tackles the thorniest customer development questions and walks us through the end-to-end research process in incredible detail, covering everything from clarifying your goals and asking the right questions, to selecting participants and synthesizing insights.     We start by going through how she applies her playbook in the early-stage startup context — when you’re shipping the first version of your product and don’t yet have the resources to invest in a full research team. We also dig into challenges such as deeply understanding the problem you’re solving, taking on a competitive or a greenfield market, and figuring out willingness to pay. We also get into best practices for prototyping and iterating, as well as some of the common roadblocks startups face later on, including how to build for multiple users and what to do when people aren’t excited about your product or using it frequently. Whether you’re talking to potential customers before you start a company, or are looking to get better feedback from your current users, there’s tons of insights in here for founders, product-builders, and design folks alike. Here’s the book Jane mentioned in the episode: Just Enough Research by Erica Hall. We also recommend checking out Jane’s recent article: What’s the point of a UX research team? You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Today’s episode is with Jane Davis, the Director of UX Research and UX Writing at Zoom. She previously led UX Research and Content Design at Zapier, and managed the growth research team at Dropbox.

Throughout the episode, Jane tackles the thorniest customer development questions and walks us through the end-to-end research process in incredible detail, covering everything from clarifying your goals and asking the right questions, to selecting participants and synthesizing insights.    

We start by going through how she applies her playbook in the early-stage startup context — when you’re shipping the first version of your product and don’t yet have the resources to invest in a full research team. We also dig into challenges such as deeply understanding the problem you’re solving, taking on a competitive or a greenfield market, and figuring out willingness to pay.

We also get into best practices for prototyping and iterating, as well as some of the common roadblocks startups face later on, including how to build for multiple users and what to do when people aren’t excited about your product or using it frequently.

Whether you’re talking to potential customers before you start a company, or are looking to get better feedback from your current users, there’s tons of insights in here for founders, product-builders, and design folks alike.

Here’s the book Jane mentioned in the episode: Just Enough Research by Erica Hall.

We also recommend checking out Jane’s recent article: What’s the point of a UX research team?

You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

]]> 3810 no Getting startup employees to stick around & learning from couples therapy — Flatiron’s Alex Buder Shapiro https://review.firstround.com/podcast/episode-32 Today’s episode is with Alex Buder Shapiro, the Chief People Officer at Flatiron Health, a company that focuses on accelerating cancer research and improving patient care.   Alex first joined Flatiron back in 2016, after an 8-year stint on Google’s People Operations team. Before her promotion to Flatiron’s executive team this past March, Alex previously ran the HR business partner and employee relations team as the startup rapidly scaled.   We kicked things off by talking about resolving conflict at work. Alex talks us through the patterns she’s seen across her career and her advice for troubleshooting, including why she loves borrowing techniques from the world of couples therapy.   We also touch on the challenge of getting employees to stick around long-term at startups. From hiring your own boss to navigating tough career conversations, Alex shares helpful tips, as well as more about her own journey rising through the ranks from IC to exec at Flatiron.   Her experiences mean that she’s also seen the growing pains that come with scaling first hand — things like the challenge of “selling” your new role with an elevator pitch when you first join, or the danger of locking into people processes and frameworks too early.   This episode explores so many different facets of what it means to be both a people leader and a long-tenured employee at a fast-growing startup, meaning there are plenty of lessons for managers and leaders in any function.   You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Thu, 29 Jul 2021 08:00:00 -0000 full 32 First Round Flatiron Health’s Chief People Officer Alex Buder Shapiro shares her lessons from scaling, including resolving workplace conflict with techniques from couples therapy and getting employees to stick around long-term at startups.  Today’s episode is with Alex Buder Shapiro, the Chief People Officer at Flatiron Health, a company that focuses on accelerating cancer research and improving patient care.   Alex first joined Flatiron back in 2016, after an 8-year stint on Google’s People Operations team. Before her promotion to Flatiron’s executive team this past March, Alex previously ran the HR business partner and employee relations team as the startup rapidly scaled.   We kicked things off by talking about resolving conflict at work. Alex talks us through the patterns she’s seen across her career and her advice for troubleshooting, including why she loves borrowing techniques from the world of couples therapy.   We also touch on the challenge of getting employees to stick around long-term at startups. From hiring your own boss to navigating tough career conversations, Alex shares helpful tips, as well as more about her own journey rising through the ranks from IC to exec at Flatiron.   Her experiences mean that she’s also seen the growing pains that come with scaling first hand — things like the challenge of “selling” your new role with an elevator pitch when you first join, or the danger of locking into people processes and frameworks too early.   This episode explores so many different facets of what it means to be both a people leader and a long-tenured employee at a fast-growing startup, meaning there are plenty of lessons for managers and leaders in any function.   You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Today’s episode is with Alex Buder Shapiro, the Chief People Officer at Flatiron Health, a company that focuses on accelerating cancer research and improving patient care.

 

Alex first joined Flatiron back in 2016, after an 8-year stint on Google’s People Operations team. Before her promotion to Flatiron’s executive team this past March, Alex previously ran the HR business partner and employee relations team as the startup rapidly scaled.

 

We kicked things off by talking about resolving conflict at work. Alex talks us through the patterns she’s seen across her career and her advice for troubleshooting, including why she loves borrowing techniques from the world of couples therapy.

 

We also touch on the challenge of getting employees to stick around long-term at startups. From hiring your own boss to navigating tough career conversations, Alex shares helpful tips, as well as more about her own journey rising through the ranks from IC to exec at Flatiron.

 

Her experiences mean that she’s also seen the growing pains that come with scaling first hand — things like the challenge of “selling” your new role with an elevator pitch when you first join, or the danger of locking into people processes and frameworks too early.

 

This episode explores so many different facets of what it means to be both a people leader and a long-tenured employee at a fast-growing startup, meaning there are plenty of lessons for managers and leaders in any function.

 

You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

]]> 3456 no How to find product/market fit before you start building — UserLeap’s Ryan Glasgow https://review.firstround.com/podcast/episode-31 Today’s episode is with Ryan Glasgow, the founder and CEO of UserLeap, a product research platform that helps PMs, user researchers, and growth marketers launch microsurveys to uncover customer insights faster. Before founding UserLeap in 2018, Ryan was a PM and early team member at Weebly (which was acquired by Square) and Vurb (which was acquired by Snapchat).    We start by rewinding the clock back to the 6-month period before Ryan started the company — when he was validating his idea and assessing the crowded market. From how he approached segmentation and early customer conversations, to common product/market fit mistakes, there’s so much advice in here for aspiring entrepreneurs.   We also get into what the first version of the product looked like, how they think about adding new features, and how UserLeap’s 3 product principles are used day-to-day. We also dig into how this self-described “product guy” taught himself founder-led sales, including the specific tactics that made the biggest difference and how he’s refined his approach into a repeatable playbook.   From the question he always asks in customer meetings, to the books that have had the biggest impact on his development, there’s tons of really tactical nuggets in here for founders and product leaders alike.   Here are the books Ryan mentioned in the episode: What Customers Want: Using Outcome-Driven Innovation to Create Breakthrough Products and Services by Anthony Ulwick You Can't Teach a Kid to Ride a Bike at a Seminar by David Sandler User Story Mapping: Discover the Whole Story, Build the Right Product by Jeff Patton   You can follow Ryan on Twitter at @ryanglasgow.   You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Thu, 22 Jul 2021 08:00:00 -0000 full 31 First Round UserLeap founder & CEO Ryan Glasgow stops by to share tactics for validating startup ideas, approaching early customer conversations, operationalizing product principles, and teaching yourself founder-led sales. Today’s episode is with Ryan Glasgow, the founder and CEO of UserLeap, a product research platform that helps PMs, user researchers, and growth marketers launch microsurveys to uncover customer insights faster. Before founding UserLeap in 2018, Ryan was a PM and early team member at Weebly (which was acquired by Square) and Vurb (which was acquired by Snapchat).    We start by rewinding the clock back to the 6-month period before Ryan started the company — when he was validating his idea and assessing the crowded market. From how he approached segmentation and early customer conversations, to common product/market fit mistakes, there’s so much advice in here for aspiring entrepreneurs.   We also get into what the first version of the product looked like, how they think about adding new features, and how UserLeap’s 3 product principles are used day-to-day. We also dig into how this self-described “product guy” taught himself founder-led sales, including the specific tactics that made the biggest difference and how he’s refined his approach into a repeatable playbook.   From the question he always asks in customer meetings, to the books that have had the biggest impact on his development, there’s tons of really tactical nuggets in here for founders and product leaders alike.   Here are the books Ryan mentioned in the episode: What Customers Want: Using Outcome-Driven Innovation to Create Breakthrough Products and Services by Anthony Ulwick You Can't Teach a Kid to Ride a Bike at a Seminar by David Sandler User Story Mapping: Discover the Whole Story, Build the Right Product by Jeff Patton   You can follow Ryan on Twitter at @ryanglasgow.   You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Today’s episode is with Ryan Glasgow, the founder and CEO of UserLeap, a product research platform that helps PMs, user researchers, and growth marketers launch microsurveys to uncover customer insights faster. Before founding UserLeap in 2018, Ryan was a PM and early team member at Weebly (which was acquired by Square) and Vurb (which was acquired by Snapchat). 

 

We start by rewinding the clock back to the 6-month period before Ryan started the company — when he was validating his idea and assessing the crowded market. From how he approached segmentation and early customer conversations, to common product/market fit mistakes, there’s so much advice in here for aspiring entrepreneurs.

 

We also get into what the first version of the product looked like, how they think about adding new features, and how UserLeap’s 3 product principles are used day-to-day. We also dig into how this self-described “product guy” taught himself founder-led sales, including the specific tactics that made the biggest difference and how he’s refined his approach into a repeatable playbook.

 

From the question he always asks in customer meetings, to the books that have had the biggest impact on his development, there’s tons of really tactical nuggets in here for founders and product leaders alike.

 

Here are the books Ryan mentioned in the episode:

 

You can follow Ryan on Twitter at @ryanglasgow.

 

You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

]]> 3915 no Nick Caldwell on the engineering cultures that power Microsoft, Reddit, Looker & Twitter https://traffic.libsyn.com/secure/firstround/EP.30_-_Nick_Caldwell_FINAL.mp3 Today’s episode is with Nick Caldwell, VP of Engineering at Twitter. Previously, Nick was at Microsoft for 15 years, eventually becoming GM of Power BI. Nick has also held roles as Reddit’s VP of Engineering and Looker’s Chief Product and Engineering Officer.   Between Microsoft, Reddit, Looker, and now Twitter, Nick’s worked for companies with vastly different cultures. And in today’s conversations, we comb through the biggest lessons from each of these orgs.    With Microsoft, we unpack what Nick believes is a massively underrated approach to organizational design. He explains the company’s rigorously approach to regular pruning and shaping the org chart. He also gives us an inside look at their management training and talent development, as well as what Nick calls the fairest performance review system he’s seen.   As Nick tells it, there was a steep learning curve when he pivoted from 15 years at Microsoft to Reddit. He doles out advice for other folks getting their bearings after a big career move. He also explains how Reddit’s mission-driven culture informs his approach to leadership at Twitter.    Finally, with Looker, Nick unpacks his biggest lessons from leading both the product and engineering teams, which offered him a unique perspective on how these two orgs that are often at odds can properly team up.   It’s an incredibly wide-reaching conversation, so there’s something for pretty much everyone. Whether you’re interested in the cultural practices that power some of the world’s biggest companies, or you’re a manager looking to level up, or you’re an engineer with goals to take on leadership, Nick’s got plenty of advice and insider stories to share.    You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 15 Jul 2021 08:00:00 -0000 full 30 First Round In this episode with Nick Caldwell, we have a wide-reaching conversation on his storied engineering leadership career at Microsoft, Reddit, Looker, and now Twitter.  Today’s episode is with Nick Caldwell, VP of Engineering at Twitter. Previously, Nick was at Microsoft for 15 years, eventually becoming GM of Power BI. Nick has also held roles as Reddit’s VP of Engineering and Looker’s Chief Product and Engineering Officer.   Between Microsoft, Reddit, Looker, and now Twitter, Nick’s worked for companies with vastly different cultures. And in today’s conversations, we comb through the biggest lessons from each of these orgs.    With Microsoft, we unpack what Nick believes is a massively underrated approach to organizational design. He explains the company’s rigorously approach to regular pruning and shaping the org chart. He also gives us an inside look at their management training and talent development, as well as what Nick calls the fairest performance review system he’s seen.   As Nick tells it, there was a steep learning curve when he pivoted from 15 years at Microsoft to Reddit. He doles out advice for other folks getting their bearings after a big career move. He also explains how Reddit’s mission-driven culture informs his approach to leadership at Twitter.    Finally, with Looker, Nick unpacks his biggest lessons from leading both the product and engineering teams, which offered him a unique perspective on how these two orgs that are often at odds can properly team up.   It’s an incredibly wide-reaching conversation, so there’s something for pretty much everyone. Whether you’re interested in the cultural practices that power some of the world’s biggest companies, or you’re a manager looking to level up, or you’re an engineer with goals to take on leadership, Nick’s got plenty of advice and insider stories to share.    You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Between Microsoft, Reddit, Looker, and now Twitter, Nick’s worked for companies with vastly different cultures. And in today’s conversations, we comb through the biggest lessons from each of these orgs. 

 

With Microsoft, we unpack what Nick believes is a massively underrated approach to organizational design. He explains the company’s rigorously approach to regular pruning and shaping the org chart. He also gives us an inside look at their management training and talent development, as well as what Nick calls the fairest performance review system he’s seen.

 

As Nick tells it, there was a steep learning curve when he pivoted from 15 years at Microsoft to Reddit. He doles out advice for other folks getting their bearings after a big career move. He also explains how Reddit’s mission-driven culture informs his approach to leadership at Twitter. 

 

Finally, with Looker, Nick unpacks his biggest lessons from leading both the product and engineering teams, which offered him a unique perspective on how these two orgs that are often at odds can properly team up.

 

It’s an incredibly wide-reaching conversation, so there’s something for pretty much everyone. Whether you’re interested in the cultural practices that power some of the world’s biggest companies, or you’re a manager looking to level up, or you’re an engineer with goals to take on leadership, Nick’s got plenty of advice and insider stories to share. 

 

You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 3542 no “Everyone wants a silver bullet” — Selling lessons from Sam Taylor, of Dropbox, Quip & now Loom https://traffic.libsyn.com/secure/firstround/EP.29_-_Sam_Taylor_FINAL.mp3 Today’s episode is with Sam Taylor, VP of Sales and Success at Loom. Previously, Sam was Dropbox’s first enterprise sales rep, and also served as Quip’s first sales leader. In today’s conversation, we dig into the key learnings from each stop in Sam’s career so far. Starting with his earliest experience at Dropbox, he walks us through his aha moment that sales is an insight driver — which includes his lessons on pricing and packaging, as well as plotting the feature roadmap as Dropbox moved up market. Next, he reflects on his time at Quip, including what sticks with him from working closely with its CEO Bret Taylor and COO Molly Graham. He also digs into his tested tactics for selling in a competitive market where you’re going up against plenty of established players, like Google and Microsoft. We then turn our attention to his current role at Loom, and how he’s threading all of those experiences together. He pays particular attention to his partnership with Loom’s product leaders, and how they’re teaming up to achieve what he jokingly calls “total Loom domination.” If you’re in sales, you won’t want to miss Sam’s insights he’s picked up over the course of multiple startup success stories. And folks that work for other functions at product-led growth companies will come away with a greater understanding and appreciation for how sales fits in. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 08 Jul 2021 08:00:00 -0000 full 29 First Round In this episode with Sam Taylor, we get super tactical with the lessons he’s picked up from his career as an early sales leader at top product-led growth companies — Dropbox, Quip and now Loom. Today’s episode is with Sam Taylor, VP of Sales and Success at Loom. Previously, Sam was Dropbox’s first enterprise sales rep, and also served as Quip’s first sales leader. In today’s conversation, we dig into the key learnings from each stop in Sam’s career so far. Starting with his earliest experience at Dropbox, he walks us through his aha moment that sales is an insight driver — which includes his lessons on pricing and packaging, as well as plotting the feature roadmap as Dropbox moved up market. Next, he reflects on his time at Quip, including what sticks with him from working closely with its CEO Bret Taylor and COO Molly Graham. He also digs into his tested tactics for selling in a competitive market where you’re going up against plenty of established players, like Google and Microsoft. We then turn our attention to his current role at Loom, and how he’s threading all of those experiences together. He pays particular attention to his partnership with Loom’s product leaders, and how they’re teaming up to achieve what he jokingly calls “total Loom domination.” If you’re in sales, you won’t want to miss Sam’s insights he’s picked up over the course of multiple startup success stories. And folks that work for other functions at product-led growth companies will come away with a greater understanding and appreciation for how sales fits in. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Today’s episode is with Sam Taylor, VP of Sales and Success at Loom. Previously, Sam was Dropbox’s first enterprise sales rep, and also served as Quip’s first sales leader.

In today’s conversation, we dig into the key learnings from each stop in Sam’s career so far. Starting with his earliest experience at Dropbox, he walks us through his aha moment that sales is an insight driver — which includes his lessons on pricing and packaging, as well as plotting the feature roadmap as Dropbox moved up market.

Next, he reflects on his time at Quip, including what sticks with him from working closely with its CEO Bret Taylor and COO Molly Graham. He also digs into his tested tactics for selling in a competitive market where you’re going up against plenty of established players, like Google and Microsoft.

We then turn our attention to his current role at Loom, and how he’s threading all of those experiences together. He pays particular attention to his partnership with Loom’s product leaders, and how they’re teaming up to achieve what he jokingly calls “total Loom domination.”

If you’re in sales, you won’t want to miss Sam’s insights he’s picked up over the course of multiple startup success stories. And folks that work for other functions at product-led growth companies will come away with a greater understanding and appreciation for how sales fits in.

You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 3708 no The do’s and don’ts of scaling from dozens of employees to thousands — McKenna Quint https://traffic.libsyn.com/secure/firstround/EP.28_-_McKenna_FINAL.mp3 Today’s episode is with McKenna Quint, who was most recently the Head of People at Plaid and also built and led the people team at Cruise Automation. Currently, she’s co-founder and general partner at Quint Capital, a seed-stage fund.   In today’s conversation, we focus on the people challenges that inevitably crop up when you’re going from a couple dozen employees to a couple thousand. We start by discussing when startups should draw from established playbooks in the people space versus when to start from first principles. She also dives into the details of bringing her data mindset to the people space, including designing a sophisticated attrition model.   Next, she tackles some of the questions she most often gets from startup founders, including whether the company should introduce levels, what to look for in your first people leadership hire, and how to approach performance reviews.   Finally, we dive into a larger conversation about the roles that companies play in today’s employee experience. From the company cultures that most inspire her, to the evolution of uncomfortable conversations in the workplace, and what pieces of the Google cultural revolution she’s ready to leave behind.   Today’s conversation is a must-listen for HR leaders of course, but also for folks at startups across the org chart that want an inside look at what’s top of mind for people leaders today — and the systems behind the scenes that powers startups to reach new heights.   Let My People Go Surfing: https://www.amazon.com/Let-People-Surfing-Education-Businessman/dp/0143037838   Management Lessons from the Mayo Clinic: https://www.amazon.com/Management-Lessons-Mayo-Clinic-Organizations/dp/1260011836   Let’s Not Kill Performance Evaluations Yet: https://hbr.org/2016/11/lets-not-kill-performance-evaluations-yet   You can follow McKenna on Twitter at @mckmoreau   You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 24 Jun 2021 08:00:00 -0000 full 28 First Round In this episode with McKenna Quint, most recently Head of People at Plaid, she unpacks the unique people challenges when aggressively scaling, including decoding data, when to pull from existing playbooks, and looking for your first people leader. Today’s episode is with McKenna Quint, who was most recently the Head of People at Plaid and also built and led the people team at Cruise Automation. Currently, she’s co-founder and general partner at Quint Capital, a seed-stage fund.   In today’s conversation, we focus on the people challenges that inevitably crop up when you’re going from a couple dozen employees to a couple thousand. We start by discussing when startups should draw from established playbooks in the people space versus when to start from first principles. She also dives into the details of bringing her data mindset to the people space, including designing a sophisticated attrition model.   Next, she tackles some of the questions she most often gets from startup founders, including whether the company should introduce levels, what to look for in your first people leadership hire, and how to approach performance reviews.   Finally, we dive into a larger conversation about the roles that companies play in today’s employee experience. From the company cultures that most inspire her, to the evolution of uncomfortable conversations in the workplace, and what pieces of the Google cultural revolution she’s ready to leave behind.   Today’s conversation is a must-listen for HR leaders of course, but also for folks at startups across the org chart that want an inside look at what’s top of mind for people leaders today — and the systems behind the scenes that powers startups to reach new heights.   Let My People Go Surfing: https://www.amazon.com/Let-People-Surfing-Education-Businessman/dp/0143037838   Management Lessons from the Mayo Clinic: https://www.amazon.com/Management-Lessons-Mayo-Clinic-Organizations/dp/1260011836   Let’s Not Kill Performance Evaluations Yet: https://hbr.org/2016/11/lets-not-kill-performance-evaluations-yet   You can follow McKenna on Twitter at @mckmoreau   You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Today’s episode is with McKenna Quint, who was most recently the Head of People at Plaid and also built and led the people team at Cruise Automation. Currently, she’s co-founder and general partner at Quint Capital, a seed-stage fund.

 

In today’s conversation, we focus on the people challenges that inevitably crop up when you’re going from a couple dozen employees to a couple thousand. We start by discussing when startups should draw from established playbooks in the people space versus when to start from first principles. She also dives into the details of bringing her data mindset to the people space, including designing a sophisticated attrition model.

 

Next, she tackles some of the questions she most often gets from startup founders, including whether the company should introduce levels, what to look for in your first people leadership hire, and how to approach performance reviews.

 

Finally, we dive into a larger conversation about the roles that companies play in today’s employee experience. From the company cultures that most inspire her, to the evolution of uncomfortable conversations in the workplace, and what pieces of the Google cultural revolution she’s ready to leave behind.

 

Today’s conversation is a must-listen for HR leaders of course, but also for folks at startups across the org chart that want an inside look at what’s top of mind for people leaders today — and the systems behind the scenes that powers startups to reach new heights.

 

Let My People Go Surfing: https://www.amazon.com/Let-People-Surfing-Education-Businessman/dp/0143037838

 

Management Lessons from the Mayo Clinic: https://www.amazon.com/Management-Lessons-Mayo-Clinic-Organizations/dp/1260011836

 

Let’s Not Kill Performance Evaluations Yet: https://hbr.org/2016/11/lets-not-kill-performance-evaluations-yet

 

You can follow McKenna on Twitter at @mckmoreau

 

You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 3973 no A look at one repeat founder’s frameworks for validating ideas — Pilot’s Waseem Daher https://review.firstround.com/podcast/episode-27 Today’s episode is with Waseem Daher, co-founder and CEO of Pilot, a company that specializes in bookkeeping, tax prep, and CFO services for high-growth startups. In addition to Pilot, Waseem co-founded two other startups with the same group of co-founders, including Ksplice, which was acquired by Oracle in 2011, and Zulip, which was acquired by Dropbox in 2014.    In today’s conversation, we pay particular attention to the earliest days of Pilot. Waseem takes us behind the scenes of the ideation stage for what would eventually become Pilot, and how the founding team gained conviction to actually start building. He also explains why Pilot landed on its human plus machine model, with a software component in addition to employing full-time accountants and tax preparers to partner with customers.     Next, we talk about building out Pilot’s ICP, and how he started getting the product into the hands of paying customers. He’s got some great tips for framing conversations with potential customers to make sure you’re building a must-have product that solves hair-on-fire problems, not a nice-to-have. Finally, he looks out to the horizon and shares how he prioritizes which offerings to add to Pilot’s product suite.    Today’s conversation is an absolute must-listen for founders and folks that have goals to one day become founders. Product pros also won’t want to miss learning from Waseem’s playbook honed over the course of building three companies.    You can follow Waseem on Twitter at @waseem. For more startup real talk from Waseem, you can subscribe to his Substack: https://waseem.substack.com/    You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson  Thu, 17 Jun 2021 08:00:00 -0000 full 27 First Round Waseem Daher is the co-founder and CEO of Pilot and previous co-founder of Ksplice (acquired by Oracle) and Zulip (acquired by Dropbox). He digs into the first year of validating a startup idea, choosing an ICP, and outlining the product roadmap. Today’s episode is with Waseem Daher, co-founder and CEO of Pilot, a company that specializes in bookkeeping, tax prep, and CFO services for high-growth startups. In addition to Pilot, Waseem co-founded two other startups with the same group of co-founders, including Ksplice, which was acquired by Oracle in 2011, and Zulip, which was acquired by Dropbox in 2014.    In today’s conversation, we pay particular attention to the earliest days of Pilot. Waseem takes us behind the scenes of the ideation stage for what would eventually become Pilot, and how the founding team gained conviction to actually start building. He also explains why Pilot landed on its human plus machine model, with a software component in addition to employing full-time accountants and tax preparers to partner with customers.     Next, we talk about building out Pilot’s ICP, and how he started getting the product into the hands of paying customers. He’s got some great tips for framing conversations with potential customers to make sure you’re building a must-have product that solves hair-on-fire problems, not a nice-to-have. Finally, he looks out to the horizon and shares how he prioritizes which offerings to add to Pilot’s product suite.    Today’s conversation is an absolute must-listen for founders and folks that have goals to one day become founders. Product pros also won’t want to miss learning from Waseem’s playbook honed over the course of building three companies.    You can follow Waseem on Twitter at @waseem. For more startup real talk from Waseem, you can subscribe to his Substack: https://waseem.substack.com/    You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson  https://waseem.substack.com/    You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson ]]> 4014 no Killing stories and creating categories — Comms tips from Shannon Brayton’s 25+ years in tech https://review.firstround.com/podcast/26 Today’s episode is with Shannon Brayton, a Silicon Valley veteran with more than two decades of experience shaping corporate narratives and leading teams at companies like LinkedIn, OpenTable, eBay, Yahoo!, and Intuit. She recently joined Bessemer as the venture capital firm’s first-ever CMO.   In today’s conversation, Shannon shares the comms and leadership lessons she’s picked up along the way. In addition to sharing her broader philosophy around the role of comms and her thoughts on why it’s one of the more underappreciated functions, Shannon gets into the tactical weeds on everything from killing stories and creating new categories, to her frameworks for building relationships with reporters. There’s plenty of career advice as well, from how she approaches selecting companies to work for, to what the transition from head of comms to CMO was like, to what she’s learned from mentors and bosses like Jeff Weiner.   Here’s the reverse mentoring post Shannon mentioned on how she approached taking on the CMO role: https://www.linkedin.com/pulse/how-i-tackled-first-100-days-my-new-role-reverse-brayton/    You can follow Shannon on Twitter at @sstubo.   You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson Thu, 10 Jun 2021 08:00:00 -0000 full 26 First Round Bessemer CMO Shannon Brayton has worked at Yahoo!, eBay, OpenTable and LinkedIn (as head of comms and CMO)— today she shares the comms and leadership lessons she’s picked up after 25+ years in Silicon Valley. Today’s episode is with Shannon Brayton, a Silicon Valley veteran with more than two decades of experience shaping corporate narratives and leading teams at companies like LinkedIn, OpenTable, eBay, Yahoo!, and Intuit. She recently joined Bessemer as the venture capital firm’s first-ever CMO.   In today’s conversation, Shannon shares the comms and leadership lessons she’s picked up along the way. In addition to sharing her broader philosophy around the role of comms and her thoughts on why it’s one of the more underappreciated functions, Shannon gets into the tactical weeds on everything from killing stories and creating new categories, to her frameworks for building relationships with reporters. There’s plenty of career advice as well, from how she approaches selecting companies to work for, to what the transition from head of comms to CMO was like, to what she’s learned from mentors and bosses like Jeff Weiner.   Here’s the reverse mentoring post Shannon mentioned on how she approached taking on the CMO role: https://www.linkedin.com/pulse/how-i-tackled-first-100-days-my-new-role-reverse-brayton/    You can follow Shannon on Twitter at @sstubo.   You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson Today’s episode is with Shannon Brayton, a Silicon Valley veteran with more than two decades of experience shaping corporate narratives and leading teams at companies like LinkedIn, OpenTable, eBay, Yahoo!, and Intuit. She recently joined Bessemer as the venture capital firm’s first-ever CMO.

 

In today’s conversation, Shannon shares the comms and leadership lessons she’s picked up along the way. In addition to sharing her broader philosophy around the role of comms and her thoughts on why it’s one of the more underappreciated functions, Shannon gets into the tactical weeds on everything from killing stories and creating new categories, to her frameworks for building relationships with reporters. There’s plenty of career advice as well, from how she approaches selecting companies to work for, to what the transition from head of comms to CMO was like, to what she’s learned from mentors and bosses like Jeff Weiner.

 

Here’s the reverse mentoring post Shannon mentioned on how she approached taking on the CMO role: https://www.linkedin.com/pulse/how-i-tackled-first-100-days-my-new-role-reverse-brayton/ 

 

You can follow Shannon on Twitter at @sstubo.

 

You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson

]]> 3542 no People leaders aren’t the CEO of culture, they’re product managers — Credit Karma’s Colleen McCreary https://review.firstround.com/podcast/25 Today’s episode is with Colleen McCreary, the Chief People Officer at Credit Karma.    With more than 20 years of experience in HR, operations, recruiting and M&A, Colleen has headed up the people function at companies such as Vevo, The Climate Corporation, and Zynga. She’s also seen the early-stages and scaled through multiple IPOs and acquisitions, which means she has a great perspective on the people problems founders tend to run into as their businesses grow.   We kick this conversation off with Colleen’s explanation of why she designs for the 80% and focuses on clarity, context, and consistency when building people organizations and crafting culture. She walks us through some really tactical examples of that work, including how her team approaches compensation at Credit Karma and the reason they do promotions quarterly.   Colleen also shares why she views the Chief People Officer not as the CEO of culture, but rather the product manager of the systems and tools that run the company. She gives a detailed look at how she approaches many of those systems, from how rewards and recognition were incredibly different at Zynga and Credit Karma, to why career growth isn’t just about a promotion. Colleen also shares her take on whether we should double down on strengths or focus on correcting weaknesses when it comes to performance.   Given her experience as a 4X Chief People Officer, today’s episode is a must-listen for first-time founders and early people leaders looking for a roadmap as their startups scale.   You can follow Colleen on Twitter at @Chiefpplofficer, and you can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Thu, 03 Jun 2021 08:00:00 -0000 full 25 First Round Today’s episode is with Colleen McCreary, the Chief People Officer at Credit Karma and former CPO at Vevo, The Climate Corporation, and Zynga. Colleen shares why she thinks of her role as the product manager of the systems that run the company, flagging Today’s episode is with Colleen McCreary, the Chief People Officer at Credit Karma.    With more than 20 years of experience in HR, operations, recruiting and M&A, Colleen has headed up the people function at companies such as Vevo, The Climate Corporation, and Zynga. She’s also seen the early-stages and scaled through multiple IPOs and acquisitions, which means she has a great perspective on the people problems founders tend to run into as their businesses grow.   We kick this conversation off with Colleen’s explanation of why she designs for the 80% and focuses on clarity, context, and consistency when building people organizations and crafting culture. She walks us through some really tactical examples of that work, including how her team approaches compensation at Credit Karma and the reason they do promotions quarterly.   Colleen also shares why she views the Chief People Officer not as the CEO of culture, but rather the product manager of the systems and tools that run the company. She gives a detailed look at how she approaches many of those systems, from how rewards and recognition were incredibly different at Zynga and Credit Karma, to why career growth isn’t just about a promotion. Colleen also shares her take on whether we should double down on strengths or focus on correcting weaknesses when it comes to performance.   Given her experience as a 4X Chief People Officer, today’s episode is a must-listen for first-time founders and early people leaders looking for a roadmap as their startups scale.   You can follow Colleen on Twitter at @Chiefpplofficer, and you can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson.  Today’s episode is with Colleen McCreary, the Chief People Officer at Credit Karma. 

 

With more than 20 years of experience in HR, operations, recruiting and M&A, Colleen has headed up the people function at companies such as Vevo, The Climate Corporation, and Zynga. She’s also seen the early-stages and scaled through multiple IPOs and acquisitions, which means she has a great perspective on the people problems founders tend to run into as their businesses grow.

 

We kick this conversation off with Colleen’s explanation of why she designs for the 80% and focuses on clarity, context, and consistency when building people organizations and crafting culture. She walks us through some really tactical examples of that work, including how her team approaches compensation at Credit Karma and the reason they do promotions quarterly.

 

Colleen also shares why she views the Chief People Officer not as the CEO of culture, but rather the product manager of the systems and tools that run the company. She gives a detailed look at how she approaches many of those systems, from how rewards and recognition were incredibly different at Zynga and Credit Karma, to why career growth isn’t just about a promotion. Colleen also shares her take on whether we should double down on strengths or focus on correcting weaknesses when it comes to performance.

 

Given her experience as a 4X Chief People Officer, today’s episode is a must-listen for first-time founders and early people leaders looking for a roadmap as their startups scale.

 

You can follow Colleen on Twitter at @Chiefpplofficer, and you can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson. 

]]> 4096 no Go unreasonably deep on complex problems and build with naivety — Bowery Farming’s Irving Fain https://review.firstround.com/podcast/24 Today’s episode is with Irving Fain, founder and CEO of Bowery Farming. Bowery is a modern farming company that grows produce indoors, free from pollutants and using significantly less water and space. Just this week, the company announced a $300 million Series C round, the largest private fundraise to date for an indoor farming company.   Bowery’s mission to democratize access to fresh, locally grown food. It’s no doubt an extremely complex problem, so it might surprise you that its founder, Irving, didn’t have any background in agriculture before starting Bowery. He was previously the CEO and founder of CrowdTwist, a loyalty and analytics solution that was eventually acquired by Oracle, and helped build iHeartRadio.    But looking back on the early days of Bowery, Irving believes his naivety was in fact an asset. Coming in with no preconceived notions about how to solve the problem, he committed to approaching agriculture with a wide aperture and going unreasonably deep. In today’s conversation, he walks us through his multi-pronged approach to developing the idea for what would become Bowery, which includes paying just as much attention to the doubters as to the folks who believed in the vision.      Next we switch gears and talk about assembling Bowery’s small-but-mighty team of five, which Irving kept deliberately small and sought out folks that didn’t have vast agriculture experience and could approach problems from first principles. Whether you’re a founder yourself or have long-term career goals to make the leap, today’s episode is packed with equal parts inspiration and tactical takeaways.    You can follow Irving on Twitter at @ifain   You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson    To learn more about Bowery Farming and its most recent fundraise, https://techcrunch.com/2021/05/25/indoor-farming-company-bowery-raises-300m/amp/ Wed, 26 May 2021 08:00:00 -0000 full 24 First Round Today’s episode is with Irving Fain, founder and CEO of Bowery Farming. Bowery’s efficient indoor farms grow produce free from pollutants and using significantly less water — democratizing access to fresh, local food. It’s an incredibly complex sy Today’s episode is with Irving Fain, founder and CEO of Bowery Farming. Bowery is a modern farming company that grows produce indoors, free from pollutants and using significantly less water and space. Just this week, the company announced a $300 million Series C round, the largest private fundraise to date for an indoor farming company.   Bowery’s mission to democratize access to fresh, locally grown food. It’s no doubt an extremely complex problem, so it might surprise you that its founder, Irving, didn’t have any background in agriculture before starting Bowery. He was previously the CEO and founder of CrowdTwist, a loyalty and analytics solution that was eventually acquired by Oracle, and helped build iHeartRadio.    But looking back on the early days of Bowery, Irving believes his naivety was in fact an asset. Coming in with no preconceived notions about how to solve the problem, he committed to approaching agriculture with a wide aperture and going unreasonably deep. In today’s conversation, he walks us through his multi-pronged approach to developing the idea for what would become Bowery, which includes paying just as much attention to the doubters as to the folks who believed in the vision.      Next we switch gears and talk about assembling Bowery’s small-but-mighty team of five, which Irving kept deliberately small and sought out folks that didn’t have vast agriculture experience and could approach problems from first principles. Whether you’re a founder yourself or have long-term career goals to make the leap, today’s episode is packed with equal parts inspiration and tactical takeaways.    You can follow Irving on Twitter at @ifain   You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson    To learn more about Bowery Farming and its most recent fundraise, https://techcrunch.com/2021/05/25/indoor-farming-company-bowery-raises-300m/amp/ Today’s episode is with Irving Fain, founder and CEO of Bowery Farming. Bowery is a modern farming company that grows produce indoors, free from pollutants and using significantly less water and space. Just this week, the company announced a $300 million Series C round, the largest private fundraise to date for an indoor farming company.

 

Bowery’s mission to democratize access to fresh, locally grown food. It’s no doubt an extremely complex problem, so it might surprise you that its founder, Irving, didn’t have any background in agriculture before starting Bowery. He was previously the CEO and founder of CrowdTwist, a loyalty and analytics solution that was eventually acquired by Oracle, and helped build iHeartRadio. 

 

But looking back on the early days of Bowery, Irving believes his naivety was in fact an asset. Coming in with no preconceived notions about how to solve the problem, he committed to approaching agriculture with a wide aperture and going unreasonably deep. In today’s conversation, he walks us through his multi-pronged approach to developing the idea for what would become Bowery, which includes paying just as much attention to the doubters as to the folks who believed in the vision.   

 

Next we switch gears and talk about assembling Bowery’s small-but-mighty team of five, which Irving kept deliberately small and sought out folks that didn’t have vast agriculture experience and could approach problems from first principles. Whether you’re a founder yourself or have long-term career goals to make the leap, today’s episode is packed with equal parts inspiration and tactical takeaways. 

 

You can follow Irving on Twitter at @ifain

 

You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

 

To learn more about Bowery Farming and its most recent fundraise, https://techcrunch.com/2021/05/25/indoor-farming-company-bowery-raises-300m/amp/

]]> 4078 no The story behind Slack’s marketing and the leap from marketer to CEO — Abstract’s Kelly Watkins  https://traffic.libsyn.com/secure/firstround/EP.23_-_Kelly_Watkins_FINAL.mp3 Today’s episode is with Kelly Watkins, CEO of Abstract, a platform for structure and transparency in the design process. In joining Abstract last year, Kelly is one of very few folks from a marketing background to take on the CEO seat. She brings a wealth of experience leading incredibly high-performing marketing teams for Slack, Github, and Bugsnag.   In today’s conversation, we start by reflecting on her first year as CEO. She shares her alternative to yearly planning, borrowing from famed military strategist John Boyd. Kelly also walks us through Abstract’s most recent product launch, and how it clearly crystallized her leadership point of view to constantly optimize for trade-offs, rather than clear-cut right and wrong.    Next we switch gears to talk about some of the lessons from her storied marketing career. She unpacks her jobs-to-be-done approach for crafting a product story when there’s loads of competition. She also takes us behind the scenes in developing Slack’s “where work happens” tagline, and crossing the chasm from a passionate early adopter customer base to the ubiquitous product it is today.    Today’s conversation is a must-listen for marketing folks, who will surely appreciate the peek behind the curtain. But all sorts of leaders with goals to more effectively collaborate with the org will come away with a deeper understanding of marketing’s art and science.    You can follow Kelly on Twitter at @_kcwatkins   You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson    To learn more about Kelly’s advice on hiring your first head of marketing, read her Medium article: https://medium.com/hackernoon/how-to-hire-your-first-head-of-marketing-67c43dd2cd73 For more on the jobs-to-be-done framework, check out this article on the Review: https://review.firstround.com/build-products-that-solve-real-problems-with-this-lightweight-jtbd-framework Thu, 20 May 2021 08:00:00 -0000 full 23 First Round Today’s episode is with Kelly Watkins, CEO of Abstract. Before joining Abstract, Kelly ran top marketing teams at Slack, Github, and Bugsnag. She shares her biggest lessons from her first year as a CEO and then she pulls back the curtain on some of the Today’s episode is with Kelly Watkins, CEO of Abstract, a platform for structure and transparency in the design process. In joining Abstract last year, Kelly is one of very few folks from a marketing background to take on the CEO seat. She brings a wealth of experience leading incredibly high-performing marketing teams for Slack, Github, and Bugsnag.   In today’s conversation, we start by reflecting on her first year as CEO. She shares her alternative to yearly planning, borrowing from famed military strategist John Boyd. Kelly also walks us through Abstract’s most recent product launch, and how it clearly crystallized her leadership point of view to constantly optimize for trade-offs, rather than clear-cut right and wrong.    Next we switch gears to talk about some of the lessons from her storied marketing career. She unpacks her jobs-to-be-done approach for crafting a product story when there’s loads of competition. She also takes us behind the scenes in developing Slack’s “where work happens” tagline, and crossing the chasm from a passionate early adopter customer base to the ubiquitous product it is today.    Today’s conversation is a must-listen for marketing folks, who will surely appreciate the peek behind the curtain. But all sorts of leaders with goals to more effectively collaborate with the org will come away with a deeper understanding of marketing’s art and science.    You can follow Kelly on Twitter at @_kcwatkins   You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson    To learn more about Kelly’s advice on hiring your first head of marketing, read her Medium article: https://medium.com/hackernoon/how-to-hire-your-first-head-of-marketing-67c43dd2cd73 For more on the jobs-to-be-done framework, check out this article on the Review: https://review.firstround.com/build-products-that-solve-real-problems-with-this-lightweight-jtbd-framework review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson    To learn more about Kelly’s advice on hiring your first head of marketing, read her Medium article: https://medium.com/hackernoon/how-to-hire-your-first-head-of-marketing-67c43dd2cd73
For more on the jobs-to-be-done framework, check out this article on the Review: https://review.firstround.com/build-products-that-solve-real-problems-with-this-lightweight-jtbd-framework]]> 3756 no Ask why it won’t work — Rick Song’s lessons from Square and building from 0 to 1 https://traffic.libsyn.com/secure/firstround/EP.22_-_Rick_at_Persona_FINAL.mp3 Today’s episode is with Rick Song, the co-founder and CEO of Persona, a platform that enables companies to create the ideal identity verification experience for their customers. Before founding Persona in 2018, Rick was an engineer at Square for 5 years, and an early team member at Square Capital.  Rick is at an exciting inflection point in his journey of building from zero to one — just last week, Persona shared that they’ve raised a $50 million Series B round. The company plans to double the team this year to keep up with revenue that’s surged more than 10x and a customer base that’s grown to include big logos like Square, Postmates, and Gusto. In today’s conversation, one theme stands out: Rick is somewhat obsessed with the idea of pre-mortems, or figuring out why things might not work out. From all the ways a candidate might fail, to why a customer won’t want a product, to how a commonly-used framework might not be a good fit, Rick brings this mindset to every aspect of running Persona.  From hiring lessons to go-to-market strategies, Rick offers up some counterintuitive thinking, including why his engineers sell and cold-email prospects, and why he doesn’t try to convince candidates that Persona is a company that will change the world. Today’s episode holds tons of insights for anyone who’s a founder or thinking about starting a company one day, but there’s also plenty in here for engineering leaders and hiring managers. You can follow Rick on Twitter at @rickcsong and learn more about Persona at https://withpersona.com/  You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 13 May 2021 08:00:00 -0000 full 22 First Round Today’s episode is with Rick Song, CEO of Persona. Before starting the identity verification company, Rick was an engineer at Square and an early team member at Square Capital. On the heels of raising a Series B round, Rick shares his approach to buildi Today’s episode is with Rick Song, the co-founder and CEO of Persona, a platform that enables companies to create the ideal identity verification experience for their customers. Before founding Persona in 2018, Rick was an engineer at Square for 5 years, and an early team member at Square Capital.  Rick is at an exciting inflection point in his journey of building from zero to one — just last week, Persona shared that they’ve raised a $50 million Series B round. The company plans to double the team this year to keep up with revenue that’s surged more than 10x and a customer base that’s grown to include big logos like Square, Postmates, and Gusto. In today’s conversation, one theme stands out: Rick is somewhat obsessed with the idea of pre-mortems, or figuring out why things might not work out. From all the ways a candidate might fail, to why a customer won’t want a product, to how a commonly-used framework might not be a good fit, Rick brings this mindset to every aspect of running Persona.  From hiring lessons to go-to-market strategies, Rick offers up some counterintuitive thinking, including why his engineers sell and cold-email prospects, and why he doesn’t try to convince candidates that Persona is a company that will change the world. Today’s episode holds tons of insights for anyone who’s a founder or thinking about starting a company one day, but there’s also plenty in here for engineering leaders and hiring managers. You can follow Rick on Twitter at @rickcsong and learn more about Persona at https://withpersona.com/  You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Today’s episode is with Rick Song, the co-founder and CEO of Persona, a platform that enables companies to create the ideal identity verification experience for their customers. Before founding Persona in 2018, Rick was an engineer at Square for 5 years, and an early team member at Square Capital. 

Rick is at an exciting inflection point in his journey of building from zero to one — just last week, Persona shared that they’ve raised a $50 million Series B round. The company plans to double the team this year to keep up with revenue that’s surged more than 10x and a customer base that’s grown to include big logos like Square, Postmates, and Gusto.

In today’s conversation, one theme stands out: Rick is somewhat obsessed with the idea of pre-mortems, or figuring out why things might not work out. From all the ways a candidate might fail, to why a customer won’t want a product, to how a commonly-used framework might not be a good fit, Rick brings this mindset to every aspect of running Persona. 

From hiring lessons to go-to-market strategies, Rick offers up some counterintuitive thinking, including why his engineers sell and cold-email prospects, and why he doesn’t try to convince candidates that Persona is a company that will change the world.

Today’s episode holds tons of insights for anyone who’s a founder or thinking about starting a company one day, but there’s also plenty in here for engineering leaders and hiring managers.

You can follow Rick on Twitter at @rickcsong and learn more about Persona at https://withpersona.com/ 

You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 3457 no Product Pitfalls From 0 Customers to the Messy Middle and IPO — Eric Berg on Okta, Intel & Fauna https://traffic.libsyn.com/secure/firstround/EP.21_-_Eric_Berg_FINAL.mp3 Today’s episode is with Eric Berg, CEO of Fauna, which is an adaptive operational database platform. In joining Fauna as its CEO in the summer of 2020, he brought a wealth of experience as a product leader. Most recently, he was the Chief Product Officer at Okta, scaling the company from 10 employees and zero customers to its eventual IPO in 2017. He started his career in product at Intel, working under the legendary Andy Grove, as well as a five-year stint as a product leader at Microsoft.   In today’s conversation, he opens up his executive playbook as he weaves together each of those experiences — and covers a lot of ground along the way. He starts by talking about early go-to-market lessons and the keys to honing in on an ICP to get Okta off the ground. He also dives into the often-maligned “messy middle,” particularly when it comes to moving upmarket and developing a pricing and packaging model that, when done well, takes a company to new heights.         We then switch gears and discuss more broadly about team building and company building — particularly the cultural lessons that stick with him from his tenure at each stop in his career. His biggest learnings include hiring folks up and down the org chart with the right ego to talent ratio and the tactical steps he takes to implement a “disagree and commit’ value so it’s not just a long-forgotten team motto. Finally, we touch on the biggest surprises as he approaches one year of sitting in the CEO seat.    Today’s conversation is a must-listen particularly for product folks, as well as others who want to more deeply understand the trade-offs that nearly every great company faces on the path to scale.    You can follow Eric on Twitter at @ericberg.   You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  Thu, 06 May 2021 08:00:00 -0000 full 21 First Round Today’s episode is with Eric Berg, CEO of Fauna. Before joining at the helm of Fauna, Eric was a product leader at some of the most interesting companies around. He shares his executive playbook, weaved together from his experiences at Okta, Microsoft a Today’s episode is with Eric Berg, CEO of Fauna, which is an adaptive operational database platform. In joining Fauna as its CEO in the summer of 2020, he brought a wealth of experience as a product leader. Most recently, he was the Chief Product Officer at Okta, scaling the company from 10 employees and zero customers to its eventual IPO in 2017. He started his career in product at Intel, working under the legendary Andy Grove, as well as a five-year stint as a product leader at Microsoft.   In today’s conversation, he opens up his executive playbook as he weaves together each of those experiences — and covers a lot of ground along the way. He starts by talking about early go-to-market lessons and the keys to honing in on an ICP to get Okta off the ground. He also dives into the often-maligned “messy middle,” particularly when it comes to moving upmarket and developing a pricing and packaging model that, when done well, takes a company to new heights.         We then switch gears and discuss more broadly about team building and company building — particularly the cultural lessons that stick with him from his tenure at each stop in his career. His biggest learnings include hiring folks up and down the org chart with the right ego to talent ratio and the tactical steps he takes to implement a “disagree and commit’ value so it’s not just a long-forgotten team motto. Finally, we touch on the biggest surprises as he approaches one year of sitting in the CEO seat.    Today’s conversation is a must-listen particularly for product folks, as well as others who want to more deeply understand the trade-offs that nearly every great company faces on the path to scale.    You can follow Eric on Twitter at @ericberg.   You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  Today’s episode is with Eric Berg, CEO of Fauna, which is an adaptive operational database platform. In joining Fauna as its CEO in the summer of 2020, he brought a wealth of experience as a product leader. Most recently, he was the Chief Product Officer at Okta, scaling the company from 10 employees and zero customers to its eventual IPO in 2017. He started his career in product at Intel, working under the legendary Andy Grove, as well as a five-year stint as a product leader at Microsoft.

 

In today’s conversation, he opens up his executive playbook as he weaves together each of those experiences — and covers a lot of ground along the way. He starts by talking about early go-to-market lessons and the keys to honing in on an ICP to get Okta off the ground. He also dives into the often-maligned “messy middle,” particularly when it comes to moving upmarket and developing a pricing and packaging model that, when done well, takes a company to new heights.      

 

We then switch gears and discuss more broadly about team building and company building — particularly the cultural lessons that stick with him from his tenure at each stop in his career. His biggest learnings include hiring folks up and down the org chart with the right ego to talent ratio and the tactical steps he takes to implement a “disagree and commit’ value so it’s not just a long-forgotten team motto. Finally, we touch on the biggest surprises as he approaches one year of sitting in the CEO seat. 

 

Today’s conversation is a must-listen particularly for product folks, as well as others who want to more deeply understand the trade-offs that nearly every great company faces on the path to scale. 

 

You can follow Eric on Twitter at @ericberg.

 

You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

]]> 3723 no After leading product & growth teams at Instacart, Wealthfront & LinkedIn, Elliot Shmukler is tackling zero to one as founder & CEO of Anomalo https://traffic.libsyn.com/secure/firstround/EP.20_-_Elliot_Shmukler_FINAL.mp3 Today’s conversation is with Elliot Shmukler, founder and CEO of Anomalo, which is a platform that validates and documents all of your data. Elliot founded Anomalo after a storied career as a product and growth leader at some of the most interesting companies around. Most recently, he was Instacart’s Chief Growth Officer, driving fast and profitable growth and geographic expansion. His jam-packed resume also includes stops at Wealthfront as the VP of Product and Growth and as a product leader at LinkedIn and eBay.    In today’s conversation, we pull on threads from his newest role as a founder of a startup going from zero to one, including his biggest surprises in the transition from executive to CEO. We also touch on how he prioritizes his time at a startup still in the earliest stages of company-building, and how to avoid wasting your time on prospects that are not all that interested in actually buying.    Next, we turn our attention to his history of picking incredible companies to work for — from the questions he asks as a candidate to the decision-making frameworks he borrows from his poker playing. Finally, we end with his biggest lessons from the best CEOs he’s worked with, including habits that set the best communicators apart from the pack, and the tactics for keeping office politics at bay so the best ideas are able to surface.    All sorts of folks will find something worthwhile in today’s conversation — whether you’re a founder still in the early phases of customer discovery, an executive with long-term goals to start your own company, or someone earlier in their career that wants to get better at spotting the next unicorn.    You can follow Elliot on Twitter at @eshmu.   You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson   To learn more about how Elliot uses A/B testing as a management framework, check out this article on First Round Review: https://review.firstround.com/how-a-b-testing-at-linkedin-wealthfront-and-ebay-made-me-a-better-manager   And check out “The Goal,” which Elliot cited as the most influential management book he’s ever read: https://www.amazon.com/Goal-Process-Ongoing-Improvement/dp/0884271951 Thu, 29 Apr 2021 09:30:00 -0000 full 20 First Round Today’s episode is with Elliot Shmukler, founder and CEO of Anomalo. Before starting Anomalo, Elliot was a top product and growth leader at Instacart, Wealthfront, LinkedIn, and eBay. He shares his biggest lessons from transitioning from exec to CEO, ho Today’s conversation is with Elliot Shmukler, founder and CEO of Anomalo, which is a platform that validates and documents all of your data. Elliot founded Anomalo after a storied career as a product and growth leader at some of the most interesting companies around. Most recently, he was Instacart’s Chief Growth Officer, driving fast and profitable growth and geographic expansion. His jam-packed resume also includes stops at Wealthfront as the VP of Product and Growth and as a product leader at LinkedIn and eBay.    In today’s conversation, we pull on threads from his newest role as a founder of a startup going from zero to one, including his biggest surprises in the transition from executive to CEO. We also touch on how he prioritizes his time at a startup still in the earliest stages of company-building, and how to avoid wasting your time on prospects that are not all that interested in actually buying.    Next, we turn our attention to his history of picking incredible companies to work for — from the questions he asks as a candidate to the decision-making frameworks he borrows from his poker playing. Finally, we end with his biggest lessons from the best CEOs he’s worked with, including habits that set the best communicators apart from the pack, and the tactics for keeping office politics at bay so the best ideas are able to surface.    All sorts of folks will find something worthwhile in today’s conversation — whether you’re a founder still in the early phases of customer discovery, an executive with long-term goals to start your own company, or someone earlier in their career that wants to get better at spotting the next unicorn.    You can follow Elliot on Twitter at @eshmu.   You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson   To learn more about how Elliot uses A/B testing as a management framework, check out this article on First Round Review: https://review.firstround.com/how-a-b-testing-at-linkedin-wealthfront-and-ebay-made-me-a-better-manager   And check out “The Goal,” which Elliot cited as the most influential management book he’s ever read: https://www.amazon.com/Goal-Process-Ongoing-Improvement/dp/0884271951 Today’s conversation is with Elliot Shmukler, founder and CEO of Anomalo, which is a platform that validates and documents all of your data. Elliot founded Anomalo after a storied career as a product and growth leader at some of the most interesting companies around. Most recently, he was Instacart’s Chief Growth Officer, driving fast and profitable growth and geographic expansion. His jam-packed resume also includes stops at Wealthfront as the VP of Product and Growth and as a product leader at LinkedIn and eBay. 

 

In today’s conversation, we pull on threads from his newest role as a founder of a startup going from zero to one, including his biggest surprises in the transition from executive to CEO. We also touch on how he prioritizes his time at a startup still in the earliest stages of company-building, and how to avoid wasting your time on prospects that are not all that interested in actually buying. 

 

Next, we turn our attention to his history of picking incredible companies to work for — from the questions he asks as a candidate to the decision-making frameworks he borrows from his poker playing. Finally, we end with his biggest lessons from the best CEOs he’s worked with, including habits that set the best communicators apart from the pack, and the tactics for keeping office politics at bay so the best ideas are able to surface. 

 

All sorts of folks will find something worthwhile in today’s conversation — whether you’re a founder still in the early phases of customer discovery, an executive with long-term goals to start your own company, or someone earlier in their career that wants to get better at spotting the next unicorn. 

 

You can follow Elliot on Twitter at @eshmu.

 

You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

 

To learn more about how Elliot uses A/B testing as a management framework, check out this article on First Round Review: https://review.firstround.com/how-a-b-testing-at-linkedin-wealthfront-and-ebay-made-me-a-better-manager

 

And check out “The Goal,” which Elliot cited as the most influential management book he’s ever read: https://www.amazon.com/Goal-Process-Ongoing-Improvement/dp/0884271951

]]> 3915 no A deep-dive into product-led growth & self-serve strategies — Notion’s & Dropbox’s Kate Taylor https://traffic.libsyn.com/secure/firstround/EP.20_-_Kate_Taylor_FINAL.mp3 Today’s episode is with Kate Taylor, who recently joined Notion as their Head of Customer Experience. Previously, Kate spent 8 years at Dropbox, leading their SMB revenue and scaled sales operation before leaving in 2020. Prior to that, she started her career as a sales rep at Salesforce.   In today’s conversation, Kate shares a wealth of advice for building out product-led growth and self-serve motions. She shares tons of nuances around going up market, competing with sales and product planning, offering up tactical advice that any founder, product or go-to-market leader can learn from.   Kate also gives us a detailed look at how they approach product prioritization at Notion, including their system of 700 tags and examples of tradeoffs they’ve had to navigate. We also get into pricing and packaging, from specific experiments at Dropbox to why interestingly Notion’s trial isn’t time based.    We also chat about how to handle a wide range of use cases, as well as the “front door” customer experience her team is trying to build. From why customer service shouldn’t be focused on getting customers off the phone faster, to the questions she asks to find more signal in their product feedback, Kate shares some counterintuitive thoughts here.   Finally, we wrap up by talking about her approach to leading teams, including why she hires for curiosity, how she tries to teach her team to ride the ups and downs of startup life, and how working for three very different CEOs — Marc Benioff, Drew Houston and Ivan Zhao — has impacted her own leadership style.   Kate isn’t on Twitter, but you can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson  Thu, 22 Apr 2021 09:30:00 -0000 full 19 First Round Today’s episode is with Kate Taylor, who spent 8 years at Dropbox (leading their SMB revenue and scaled sales operation) and is now the Head of Customer Experience at Notion. Kate is full of actionable tactics on getting product-led growth, self-serve a Today’s episode is with Kate Taylor, who recently joined Notion as their Head of Customer Experience. Previously, Kate spent 8 years at Dropbox, leading their SMB revenue and scaled sales operation before leaving in 2020. Prior to that, she started her career as a sales rep at Salesforce.   In today’s conversation, Kate shares a wealth of advice for building out product-led growth and self-serve motions. She shares tons of nuances around going up market, competing with sales and product planning, offering up tactical advice that any founder, product or go-to-market leader can learn from.   Kate also gives us a detailed look at how they approach product prioritization at Notion, including their system of 700 tags and examples of tradeoffs they’ve had to navigate. We also get into pricing and packaging, from specific experiments at Dropbox to why interestingly Notion’s trial isn’t time based.    We also chat about how to handle a wide range of use cases, as well as the “front door” customer experience her team is trying to build. From why customer service shouldn’t be focused on getting customers off the phone faster, to the questions she asks to find more signal in their product feedback, Kate shares some counterintuitive thoughts here.   Finally, we wrap up by talking about her approach to leading teams, including why she hires for curiosity, how she tries to teach her team to ride the ups and downs of startup life, and how working for three very different CEOs — Marc Benioff, Drew Houston and Ivan Zhao — has impacted her own leadership style.   Kate isn’t on Twitter, but you can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson  Today’s episode is with Kate Taylor, who recently joined Notion as their Head of Customer Experience. Previously, Kate spent 8 years at Dropbox, leading their SMB revenue and scaled sales operation before leaving in 2020. Prior to that, she started her career as a sales rep at Salesforce.

 

In today’s conversation, Kate shares a wealth of advice for building out product-led growth and self-serve motions. She shares tons of nuances around going up market, competing with sales and product planning, offering up tactical advice that any founder, product or go-to-market leader can learn from.

 

Kate also gives us a detailed look at how they approach product prioritization at Notion, including their system of 700 tags and examples of tradeoffs they’ve had to navigate. We also get into pricing and packaging, from specific experiments at Dropbox to why interestingly Notion’s trial isn’t time based. 

 

We also chat about how to handle a wide range of use cases, as well as the “front door” customer experience her team is trying to build. From why customer service shouldn’t be focused on getting customers off the phone faster, to the questions she asks to find more signal in their product feedback, Kate shares some counterintuitive thoughts here.

 

Finally, we wrap up by talking about her approach to leading teams, including why she hires for curiosity, how she tries to teach her team to ride the ups and downs of startup life, and how working for three very different CEOs — Marc Benioff, Drew Houston and Ivan Zhao — has impacted her own leadership style.

 

Kate isn’t on Twitter, but you can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

]]> 3433 no Setting up the people function and training for empathy — Lambda School’s Mark Frein https://traffic.libsyn.com/secure/firstround/EP.19_-_Mark_Frein_FINAL.mp3 Today’s episode is with Mark Frein, the Chief People Officer & Head of Alumni Programs at Lambda School. Previously, Mark served as the Chief People Officer at both InVision and Return Path. He also ran his own leadership development consultancy and taught on HR topics as an adjunct professor.   Mark has an invaluable perspective and tons of advice to share after setting up several people orgs in a range of different companies. In this conversation, Mark shares his approach to the CPO role and his philosophy around the function more generally, including why he thinks at its core, it’s a data and analytical function and how to match the employee experience to your company’s competitive positioning.   He also gets incredibly tactical on a wide range of topics, from how to hire with empathy and advice for approaching skip-levels, to gathering employee feedback and driving career conversations.   Today’s conversation is a must-listen for both founders and early-stage people leaders trying to thoughtfully scale this function, as well as for current and aspiring managers hoping to hone their leadership and development chops.   You can follow Mark on Twitter at @freintime, and you can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  Thu, 15 Apr 2021 09:30:00 -0000 full 18 First Round Today’s episode is with Mark Frein, the Chief People Officer & Head of Alumni Programs at Lambda School and former CPO at InVision. As we dive into how to set up this essential startup function, Mark shares advice on everything from org design and onboa Today’s episode is with Mark Frein, the Chief People Officer & Head of Alumni Programs at Lambda School. Previously, Mark served as the Chief People Officer at both InVision and Return Path. He also ran his own leadership development consultancy and taught on HR topics as an adjunct professor.   Mark has an invaluable perspective and tons of advice to share after setting up several people orgs in a range of different companies. In this conversation, Mark shares his approach to the CPO role and his philosophy around the function more generally, including why he thinks at its core, it’s a data and analytical function and how to match the employee experience to your company’s competitive positioning.   He also gets incredibly tactical on a wide range of topics, from how to hire with empathy and advice for approaching skip-levels, to gathering employee feedback and driving career conversations.   Today’s conversation is a must-listen for both founders and early-stage people leaders trying to thoughtfully scale this function, as well as for current and aspiring managers hoping to hone their leadership and development chops.   You can follow Mark on Twitter at @freintime, and you can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  Today’s episode is with Mark Frein, the Chief People Officer & Head of Alumni Programs at Lambda School. Previously, Mark served as the Chief People Officer at both InVision and Return Path. He also ran his own leadership development consultancy and taught on HR topics as an adjunct professor.

 

Mark has an invaluable perspective and tons of advice to share after setting up several people orgs in a range of different companies. In this conversation, Mark shares his approach to the CPO role and his philosophy around the function more generally, including why he thinks at its core, it’s a data and analytical function and how to match the employee experience to your company’s competitive positioning.

 

He also gets incredibly tactical on a wide range of topics, from how to hire with empathy and advice for approaching skip-levels, to gathering employee feedback and driving career conversations.

 

Today’s conversation is a must-listen for both founders and early-stage people leaders trying to thoughtfully scale this function, as well as for current and aspiring managers hoping to hone their leadership and development chops.

 

You can follow Mark on Twitter at @freintime, and you can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

]]> 4045 no How Thumbtack CEO Marco Zappacosta Parses Through Mountains of Advice as a First-Time Founder https://traffic.libsyn.com/secure/firstround/EP.18_-_Marco_Zappacosta_FINAL.mp3 Today’s episode is with Marco Zappacosta, co-founder and CEO of Thumbtack. He’s spent the last 13 years building the company into a billion-dollar business  — and it’s his first and only job after graduating college.   In today’s conversation, Marco dives into the company milestones that require a return to first principles versus pulling from a tested playbook, and the mental models he leans on when parsing through the mountains of advice he gets as a first-time founder and CEO. He connects these dots to how he manages Thumbtack’s board so those quarterly meetings are a critical resource, not just a time suck — and why he shares the board deck with the entire company.   He also candidly reflects on Thumbtack’s COVID-related layoff last year, and what he specifically did as CEO to make sure the folks that remained still had confidence in the company and his leadership moving forward.    Finally, he opens up his playbook for choosing what to spend his time on as a busy CEO with only so many hours in the day — and perhaps more importantly, how he stays accountable for these priorities.   Today’s conversation is a must-listen for company-builders across all industries and growth stages, as well as folks that have hopes to someday occupy these same seats.    To learn more about how Marco and Thumbtack approach executive hiring, check out the article on First Round Review: https://review.firstround.com/assembling-an-executive-leadership-team-is-daunting-let-thumbtacks-ceo-help   You can follow Marco on Twitter at @mlz.   You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson  Thu, 08 Apr 2021 09:30:00 -0000 full 17 First Round Today’s episode is with Marco Zappacosta, co-founder and CEO of Thumbtack. Reflecting on the 13-year journey of creating Thumbtack as a first-time founder, Mark pays special attention to the many cultural hurdles that founders must clear on the path to Today’s episode is with Marco Zappacosta, co-founder and CEO of Thumbtack. He’s spent the last 13 years building the company into a billion-dollar business  — and it’s his first and only job after graduating college.   In today’s conversation, Marco dives into the company milestones that require a return to first principles versus pulling from a tested playbook, and the mental models he leans on when parsing through the mountains of advice he gets as a first-time founder and CEO. He connects these dots to how he manages Thumbtack’s board so those quarterly meetings are a critical resource, not just a time suck — and why he shares the board deck with the entire company.   He also candidly reflects on Thumbtack’s COVID-related layoff last year, and what he specifically did as CEO to make sure the folks that remained still had confidence in the company and his leadership moving forward.    Finally, he opens up his playbook for choosing what to spend his time on as a busy CEO with only so many hours in the day — and perhaps more importantly, how he stays accountable for these priorities.   Today’s conversation is a must-listen for company-builders across all industries and growth stages, as well as folks that have hopes to someday occupy these same seats.    To learn more about how Marco and Thumbtack approach executive hiring, check out the article on First Round Review: https://review.firstround.com/assembling-an-executive-leadership-team-is-daunting-let-thumbtacks-ceo-help   You can follow Marco on Twitter at @mlz.   You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson  Today’s episode is with Marco Zappacosta, co-founder and CEO of Thumbtack. He’s spent the last 13 years building the company into a billion-dollar business  — and it’s his first and only job after graduating college.

 

In today’s conversation, Marco dives into the company milestones that require a return to first principles versus pulling from a tested playbook, and the mental models he leans on when parsing through the mountains of advice he gets as a first-time founder and CEO. He connects these dots to how he manages Thumbtack’s board so those quarterly meetings are a critical resource, not just a time suck — and why he shares the board deck with the entire company.

 

He also candidly reflects on Thumbtack’s COVID-related layoff last year, and what he specifically did as CEO to make sure the folks that remained still had confidence in the company and his leadership moving forward. 

 

Finally, he opens up his playbook for choosing what to spend his time on as a busy CEO with only so many hours in the day — and perhaps more importantly, how he stays accountable for these priorities.

 

Today’s conversation is a must-listen for company-builders across all industries and growth stages, as well as folks that have hopes to someday occupy these same seats. 

 

To learn more about how Marco and Thumbtack approach executive hiring, check out the article on First Round Review: https://review.firstround.com/assembling-an-executive-leadership-team-is-daunting-let-thumbtacks-ceo-help

 

You can follow Marco on Twitter at @mlz.

 

You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

]]> 4070 no Building engineering orgs and new products at Segment, Dropbox & Facebook — Tido Carriero https://traffic.libsyn.com/secure/firstround/EP.17_-_Thomas_Carriero_FINAL.mp3 Today’s episode is with Tido Carriero, the Chief Product Officer at Segment, a customer data platform which was recently acquired by Twilio. Before that, he built out the engineering teams that worked on the core product and the initial business product at Dropbox. Tido started out his career in 2008 as an early member of the Facebook ads engineering team, and went on to become an eng manager on the Pages team, a transition from IC to leadership that he talks about in this episode.    In today’s conversation, we dig into his career lessons from building engineering orgs and launching new product lines at several different top tech companies. From the pros and cons of single threaded leadership to his black box analogy for assessing a team’s performance, there are tons of tactics in here on how leaders can think differently about org design, planning and execution. He also shares several gems of advice for new engineering managers and new managers-of-managers.   We also chat about the path to product/market fit, especially for multi-product strategies. Tido shares his advice for going from zero to one in a new product, including the simple milestone his teams have to hit before he’ll greenlight a new project, why he prefers iterative approaches over “big bang launches,” and his thoughts on why Dropbox struggled here. (Tido shares more of his thoughts on finding product/market fit in the context of multi-product strategies here in this blog post: https://segment.com/blog/finding-product-market-fit-again/)   Tido isn’t on Twitter, but you can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 01 Apr 2021 09:30:00 -0000 full 16 First Round Today’s episode is with Tido Carriero, an engineering leader who’s built out teams at Facebook, Dropbox and Segment, where he is currently the Chief Product Officer. From his thoughts on organizational design and advice for newly minted engineering ma Today’s episode is with Tido Carriero, the Chief Product Officer at Segment, a customer data platform which was recently acquired by Twilio. Before that, he built out the engineering teams that worked on the core product and the initial business product at Dropbox. Tido started out his career in 2008 as an early member of the Facebook ads engineering team, and went on to become an eng manager on the Pages team, a transition from IC to leadership that he talks about in this episode.    In today’s conversation, we dig into his career lessons from building engineering orgs and launching new product lines at several different top tech companies. From the pros and cons of single threaded leadership to his black box analogy for assessing a team’s performance, there are tons of tactics in here on how leaders can think differently about org design, planning and execution. He also shares several gems of advice for new engineering managers and new managers-of-managers.   We also chat about the path to product/market fit, especially for multi-product strategies. Tido shares his advice for going from zero to one in a new product, including the simple milestone his teams have to hit before he’ll greenlight a new project, why he prefers iterative approaches over “big bang launches,” and his thoughts on why Dropbox struggled here. (Tido shares more of his thoughts on finding product/market fit in the context of multi-product strategies here in this blog post: https://segment.com/blog/finding-product-market-fit-again/)   Tido isn’t on Twitter, but you can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson https://segment.com/blog/finding-product-market-fit-again/)   Tido isn’t on Twitter, but you can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson]]> 3484 no Essentials to engaging employees & developing high-quality managers — Qualtrics’ Russ Laraway https://traffic.libsyn.com/secure/firstround/EP.16_-_Russ_Laraway_FINAL.mp3 Today’s episode is with Russ Laraway. After starting out in the Marine Corps, Russ made his way into the world of startups, joining Google in 2005 where he led teams for 7 years and was recognized as one of the company’s best managers. Russ then went to Twitter, where he founded and ran the SMB advertising business. Afterwards, he teamed up with Kim Scott to co-found Candor, Inc to help people implement the concepts from Radical Candor and have better relationships at work.    In 2018, he joined Qualtrics as the Chief People Officer, a position he stepped away from this past January to focus on helping the company’s customers think differently about employee experience. Russ also has a book on this topic coming out soon — and we can’t wait to read it.   In today’s conversation, we dig into how startups can drive employee engagement and develop high-quality managers. Russ reaches across his career to serve up some incredible wisdom, whether you’re a first-time manager or a seasoned leader.   He starts by sharing his direction-coaching-career framework, along with his thoughts on where companies go wrong on OKRs. He also gets really tactical, sharing the typical phrases he relies on when delivering feedback, his go-to questions for soliciting what folks on his team really think, and underrated questions to include in employment engagement surveys. Finally, Russ gives us 13 recommendations for leadership reads for managers.   For more of his thinking on talent development, we recommend reading his article from a few years ago in the First Round Review: https://review.firstround.com/three-powerful-conversations-managers-must-have-to-develop-their-people    You can follow Russ on Twitter at @ral1 and you can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  Thu, 18 Mar 2021 09:30:00 -0000 full 15 First Round Today’s episode is with Russ Laraway, a seasoned leader who’s been at Google, Twitter, Candor Inc, and Qualtrics, where he recently served as Chief People Officer before shifting into a new role helping the company’s customers think differently abou Today’s episode is with Russ Laraway. After starting out in the Marine Corps, Russ made his way into the world of startups, joining Google in 2005 where he led teams for 7 years and was recognized as one of the company’s best managers. Russ then went to Twitter, where he founded and ran the SMB advertising business. Afterwards, he teamed up with Kim Scott to co-found Candor, Inc to help people implement the concepts from Radical Candor and have better relationships at work.    In 2018, he joined Qualtrics as the Chief People Officer, a position he stepped away from this past January to focus on helping the company’s customers think differently about employee experience. Russ also has a book on this topic coming out soon — and we can’t wait to read it.   In today’s conversation, we dig into how startups can drive employee engagement and develop high-quality managers. Russ reaches across his career to serve up some incredible wisdom, whether you’re a first-time manager or a seasoned leader.   He starts by sharing his direction-coaching-career framework, along with his thoughts on where companies go wrong on OKRs. He also gets really tactical, sharing the typical phrases he relies on when delivering feedback, his go-to questions for soliciting what folks on his team really think, and underrated questions to include in employment engagement surveys. Finally, Russ gives us 13 recommendations for leadership reads for managers.   For more of his thinking on talent development, we recommend reading his article from a few years ago in the First Round Review: https://review.firstround.com/three-powerful-conversations-managers-must-have-to-develop-their-people    You can follow Russ on Twitter at @ral1 and you can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  Today’s episode is with Russ Laraway. After starting out in the Marine Corps, Russ made his way into the world of startups, joining Google in 2005 where he led teams for 7 years and was recognized as one of the company’s best managers. Russ then went to Twitter, where he founded and ran the SMB advertising business. Afterwards, he teamed up with Kim Scott to co-found Candor, Inc to help people implement the concepts from Radical Candor and have better relationships at work. 

 

In 2018, he joined Qualtrics as the Chief People Officer, a position he stepped away from this past January to focus on helping the company’s customers think differently about employee experience. Russ also has a book on this topic coming out soon — and we can’t wait to read it.

 

In today’s conversation, we dig into how startups can drive employee engagement and develop high-quality managers. Russ reaches across his career to serve up some incredible wisdom, whether you’re a first-time manager or a seasoned leader.

 

He starts by sharing his direction-coaching-career framework, along with his thoughts on where companies go wrong on OKRs. He also gets really tactical, sharing the typical phrases he relies on when delivering feedback, his go-to questions for soliciting what folks on his team really think, and underrated questions to include in employment engagement surveys. Finally, Russ gives us 13 recommendations for leadership reads for managers.

 

For more of his thinking on talent development, we recommend reading his article from a few years ago in the First Round Review: https://review.firstround.com/three-powerful-conversations-managers-must-have-to-develop-their-people 

 

You can follow Russ on Twitter at @ral1 and you can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

]]> 4292 no CEO Jeff Lawson Reflects on the Peaks and Valleys of Twilio’s Growth Story https://traffic.libsyn.com/secure/firstround/EP.15_-_Jeff_Lawson_FINAL.mp3 Today’s episode is with Jeff Lawson, co-founder and CEO of Twilio. He’s spent the last 13 years building and running the company, including leading through a successful IPO in 2016.    In today’s conversation, Jeff looks back on some of the peaks and valleys in Twilio’s journey, and his own evolution as the CEO. He dives into some of the initial wins, like going against conventional wisdom to launch a second product in the early days of Twilio. He’s equally game to unpack some of the mistakes along Twilio’s path — like when one of their biggest customers, Uber, significantly scaled back their investment in Twilio’s products.    Jeff also opens up the pages from the playbook he pulled from his time at Amazon, chiefly Twilio’s “write it down” company value, and makes his case for why PowerPoint is a terrible decision-making tool. He takes us inside Twilio’s C-suite, including why they do post-mortems when things go right — not just when they go wrong. He also sketches out his “aha” moment that his executive team needed to argue more.    Today’s conversation is a must-listen for company-builders across all industries and growth stages, as well as folks that have hopes to someday occupy these same seats.    Jeff’s new book is titled “Ask Your Developer: How to Harness the Power of Software Developers and Win in the 21st Century.” https://www.amazon.com/Ask-Your-Developer-Software-Developers/dp/0063018292   To learn more about how Twilio approaches company values, check out this article on First Round Review: https://review.firstround.com/draw-the-owl-and-other-company-values-you-didnt-know-you-should-have   You can follow Jeff on Twitter at @jeffiel.   You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  Thu, 11 Mar 2021 10:30:00 -0000 full 14 First Round Today’s episode is with Jeff Lawson, co-founder and CEO of Twilio. Reflecting on the 13-year journey of creating Twilio, Jeff shares the peaks and valleys and some unexpected aha moments — from getting his executive team to argue more, missteps with t Today’s episode is with Jeff Lawson, co-founder and CEO of Twilio. He’s spent the last 13 years building and running the company, including leading through a successful IPO in 2016.    In today’s conversation, Jeff looks back on some of the peaks and valleys in Twilio’s journey, and his own evolution as the CEO. He dives into some of the initial wins, like going against conventional wisdom to launch a second product in the early days of Twilio. He’s equally game to unpack some of the mistakes along Twilio’s path — like when one of their biggest customers, Uber, significantly scaled back their investment in Twilio’s products.    Jeff also opens up the pages from the playbook he pulled from his time at Amazon, chiefly Twilio’s “write it down” company value, and makes his case for why PowerPoint is a terrible decision-making tool. He takes us inside Twilio’s C-suite, including why they do post-mortems when things go right — not just when they go wrong. He also sketches out his “aha” moment that his executive team needed to argue more.    Today’s conversation is a must-listen for company-builders across all industries and growth stages, as well as folks that have hopes to someday occupy these same seats.    Jeff’s new book is titled “Ask Your Developer: How to Harness the Power of Software Developers and Win in the 21st Century.” https://www.amazon.com/Ask-Your-Developer-Software-Developers/dp/0063018292   To learn more about how Twilio approaches company values, check out this article on First Round Review: https://review.firstround.com/draw-the-owl-and-other-company-values-you-didnt-know-you-should-have   You can follow Jeff on Twitter at @jeffiel.   You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  Today’s episode is with Jeff Lawson, co-founder and CEO of Twilio. He’s spent the last 13 years building and running the company, including leading through a successful IPO in 2016. 

 

In today’s conversation, Jeff looks back on some of the peaks and valleys in Twilio’s journey, and his own evolution as the CEO. He dives into some of the initial wins, like going against conventional wisdom to launch a second product in the early days of Twilio. He’s equally game to unpack some of the mistakes along Twilio’s path — like when one of their biggest customers, Uber, significantly scaled back their investment in Twilio’s products. 

 

Jeff also opens up the pages from the playbook he pulled from his time at Amazon, chiefly Twilio’s “write it down” company value, and makes his case for why PowerPoint is a terrible decision-making tool. He takes us inside Twilio’s C-suite, including why they do post-mortems when things go right — not just when they go wrong. He also sketches out his “aha” moment that his executive team needed to argue more. 

 

Today’s conversation is a must-listen for company-builders across all industries and growth stages, as well as folks that have hopes to someday occupy these same seats. 

 

Jeff’s new book is titled “Ask Your Developer: How to Harness the Power of Software Developers and Win in the 21st Century.” https://www.amazon.com/Ask-Your-Developer-Software-Developers/dp/0063018292

 

To learn more about how Twilio approaches company values, check out this article on First Round Review: https://review.firstround.com/draw-the-owl-and-other-company-values-you-didnt-know-you-should-have

 

You can follow Jeff on Twitter at @jeffiel.

 

You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

]]> 3868 no Treat Operational Debt like Tech Debt — Leah Sutton on Elastic’s Distributed Work Playbook https://traffic.libsyn.com/secure/firstround/EP.14_-_Leah_Sutton_FINAL.mp3 Today’s episode is with Leah Sutton, SVP of Global HR at Elastic. Leah’s been in the HR space for over 20 years, and now leads everything from HR operations to recruiting and employee engagement for Elastic’s fully-distributed employee base, which includes over 2,000 spread across 40 countries and 48 states.  In today’s conversation, we look closely under the hood of what Leah calls Elastic’s “distributed by design” company DNA. She walks us through her learnings tackling challenges companies now are paying close attention to — including how to interview for leaders that can manage well remotely — and even dives into the nitty-gritty details about payroll and compensation across regions. She also outlines a few of the tactics Elastic has leaned on to smooth over some of the language and cultural barriers that often trip up global leadership teams. Leah zooms out even further to discuss Elastic’s source code, which she describes as not so much a traditional list of values but more the things that make Elastic, Elastic. Finally, she sketches out her pitch for why companies should talk about operational debt as much as they do technical debt. Today’s conversation is a must-listen for HR leaders and founders — and for folks on the hunt for a more systematic approach to the new challenges of distributed work.   Learn more about Elastic’s source code here: https://www.elastic.co/about/our-source-code   You can follow Leah on Twitter at @leahesutton   You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  Thu, 04 Mar 2021 10:30:00 -0000 full 13 First Round Today’s episode is with Leah Sutton, SVP of Global HR at Elastic, which provides open-source software for search and data analytics. Elastic has been a distributed company from the beginning, now with over 2,000 employees across 40 countries and 48 stat Today’s episode is with Leah Sutton, SVP of Global HR at Elastic. Leah’s been in the HR space for over 20 years, and now leads everything from HR operations to recruiting and employee engagement for Elastic’s fully-distributed employee base, which includes over 2,000 spread across 40 countries and 48 states.  In today’s conversation, we look closely under the hood of what Leah calls Elastic’s “distributed by design” company DNA. She walks us through her learnings tackling challenges companies now are paying close attention to — including how to interview for leaders that can manage well remotely — and even dives into the nitty-gritty details about payroll and compensation across regions. She also outlines a few of the tactics Elastic has leaned on to smooth over some of the language and cultural barriers that often trip up global leadership teams. Leah zooms out even further to discuss Elastic’s source code, which she describes as not so much a traditional list of values but more the things that make Elastic, Elastic. Finally, she sketches out her pitch for why companies should talk about operational debt as much as they do technical debt. Today’s conversation is a must-listen for HR leaders and founders — and for folks on the hunt for a more systematic approach to the new challenges of distributed work.   Learn more about Elastic’s source code here: https://www.elastic.co/about/our-source-code   You can follow Leah on Twitter at @leahesutton   You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  Today’s episode is with Leah Sutton, SVP of Global HR at Elastic. Leah’s been in the HR space for over 20 years, and now leads everything from HR operations to recruiting and employee engagement for Elastic’s fully-distributed employee base, which includes over 2,000 spread across 40 countries and 48 states. 

In today’s conversation, we look closely under the hood of what Leah calls Elastic’s “distributed by design” company DNA. She walks us through her learnings tackling challenges companies now are paying close attention to — including how to interview for leaders that can manage well remotely — and even dives into the nitty-gritty details about payroll and compensation across regions. She also outlines a few of the tactics Elastic has leaned on to smooth over some of the language and cultural barriers that often trip up global leadership teams.

Leah zooms out even further to discuss Elastic’s source code, which she describes as not so much a traditional list of values but more the things that make Elastic, Elastic. Finally, she sketches out her pitch for why companies should talk about operational debt as much as they do technical debt.

Today’s conversation is a must-listen for HR leaders and founders — and for folks on the hunt for a more systematic approach to the new challenges of distributed work.

 

Learn more about Elastic’s source code here: https://www.elastic.co/about/our-source-code

 

You can follow Leah on Twitter at @leahesutton

 

You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

]]> 3447 no “My product is the company” — Kevin Fishner on how startups can build better systems https://traffic.libsyn.com/secure/firstround/EP.10_-_Kevin_Fishner_FINAL.mp3 Today’s episode is with Kevin Fishner, Chief of Staff at HashiCorp. As the first business hire at the cloud infrastructure automation company, he previously built out the sales, marketing and product management teams. Now as chief of staff, he’s focused on building a strong foundation of company-wide systems, now that the team has grown to over 1000 people. In today’s conversation, Kevin shares a detailed look at how they run meetings, set and track progress toward goals, and make decisions through writing at HashiCorp.  He also shares incredibly tactical advice for making annual planning more effective, including the unique business simulation they run, their scorecard system, and the weekly and quarterly meetings that help them stay focused on important KPIs. While today’s episode is clearly a must-listen for fellow chiefs of staff and founders spinning up a company from scratch, managers and leaders of all kinds will walk away with several takeaways on how to make their teams more effective. Because so much of what he shared is so detailed, we’ll be sharing some templates and visuals to go along with Kevin’s interview over on the First Round Review, so be sure to check that out.  You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  Thu, 25 Feb 2021 10:30:00 -0000 full 12 First Round Today’s episode is with Kevin Fishner, the first business hire, former VP of Product, and current Chief of Staff at HashiCorp, a cloud infrastructure automation company. Kevin takes us through the most important systems at HashiCorp, including how they Today’s episode is with Kevin Fishner, Chief of Staff at HashiCorp. As the first business hire at the cloud infrastructure automation company, he previously built out the sales, marketing and product management teams. Now as chief of staff, he’s focused on building a strong foundation of company-wide systems, now that the team has grown to over 1000 people. In today’s conversation, Kevin shares a detailed look at how they run meetings, set and track progress toward goals, and make decisions through writing at HashiCorp.  He also shares incredibly tactical advice for making annual planning more effective, including the unique business simulation they run, their scorecard system, and the weekly and quarterly meetings that help them stay focused on important KPIs. While today’s episode is clearly a must-listen for fellow chiefs of staff and founders spinning up a company from scratch, managers and leaders of all kinds will walk away with several takeaways on how to make their teams more effective. Because so much of what he shared is so detailed, we’ll be sharing some templates and visuals to go along with Kevin’s interview over on the First Round Review, so be sure to check that out.  You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  Today’s episode is with Kevin Fishner, Chief of Staff at HashiCorp. As the first business hire at the cloud infrastructure automation company, he previously built out the sales, marketing and product management teams.

Now as chief of staff, he’s focused on building a strong foundation of company-wide systems, now that the team has grown to over 1000 people. In today’s conversation, Kevin shares a detailed look at how they run meetings, set and track progress toward goals, and make decisions through writing at HashiCorp. 

He also shares incredibly tactical advice for making annual planning more effective, including the unique business simulation they run, their scorecard system, and the weekly and quarterly meetings that help them stay focused on important KPIs.

While today’s episode is clearly a must-listen for fellow chiefs of staff and founders spinning up a company from scratch, managers and leaders of all kinds will walk away with several takeaways on how to make their teams more effective.

Because so much of what he shared is so detailed, we’ll be sharing some templates and visuals to go along with Kevin’s interview over on the First Round Review, so be sure to check that out. 

You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

]]> 4411 no Growing a consumer product from scratch to 1 billion users — Google Photos’ David Lieb https://traffic.libsyn.com/secure/firstround/EP.11_-_David_Lieb_FINAL.mp3 Today’s episode is with David Lieb, the Director of Google Photos. Previously, he was the founder/CEO of Bump, an app that allowed users to swap contact information by physically bumping phones. Bump was acquired by Google in 2013, and formed the basis for the design of Google Photos, which launched in 2015 and passed the 1 billion users mark in 2019. In today’s conversation, David takes us through that journey of building a consumer product from scratch and scaling it to over a billion users in just four years. He shares the mistakes they made while building Bump, what he learned from navigating big company politics at Google, and how they pinpointed the problem in the photo-sharing space. From the precise questions they asked in user interviews, to how they stack ranked for the canonical users, there’s tons of wisdom in here for early product builders. There’s also lessons from operating at Google’s scale as well, including how his approach to planning and org design have evolved. Learn more about the Spotify “squads’ model that David mentioned in the org design section here: https://medium.com/pm101/spotify-squad-framework-part-i-8f74bcfcd761    You can follow David on Twitter at @dflieb, and you can learn more about his approach to building products on First Round Review: https://firstround.com/review/cognitive-overhead-is-your-products-overlord-topple-it-with-these-tips/    You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  Thu, 18 Feb 2021 10:30:00 -0000 full 11 First Round Today’s episode is with David Lieb, the Director of Google Photos and former founder/CEO of Bump. He unpacks the underpinnings of Google Photos’ success and walks us through how product builders can focus on solving real problems. From how annual plan Today’s episode is with David Lieb, the Director of Google Photos. Previously, he was the founder/CEO of Bump, an app that allowed users to swap contact information by physically bumping phones. Bump was acquired by Google in 2013, and formed the basis for the design of Google Photos, which launched in 2015 and passed the 1 billion users mark in 2019. In today’s conversation, David takes us through that journey of building a consumer product from scratch and scaling it to over a billion users in just four years. He shares the mistakes they made while building Bump, what he learned from navigating big company politics at Google, and how they pinpointed the problem in the photo-sharing space. From the precise questions they asked in user interviews, to how they stack ranked for the canonical users, there’s tons of wisdom in here for early product builders. There’s also lessons from operating at Google’s scale as well, including how his approach to planning and org design have evolved. Learn more about the Spotify “squads’ model that David mentioned in the org design section here: https://medium.com/pm101/spotify-squad-framework-part-i-8f74bcfcd761    You can follow David on Twitter at @dflieb, and you can learn more about his approach to building products on First Round Review: https://firstround.com/review/cognitive-overhead-is-your-products-overlord-topple-it-with-these-tips/    You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  Today’s episode is with David Lieb, the Director of Google Photos. Previously, he was the founder/CEO of Bump, an app that allowed users to swap contact information by physically bumping phones. Bump was acquired by Google in 2013, and formed the basis for the design of Google Photos, which launched in 2015 and passed the 1 billion users mark in 2019.

In today’s conversation, David takes us through that journey of building a consumer product from scratch and scaling it to over a billion users in just four years. He shares the mistakes they made while building Bump, what he learned from navigating big company politics at Google, and how they pinpointed the problem in the photo-sharing space.

From the precise questions they asked in user interviews, to how they stack ranked for the canonical users, there’s tons of wisdom in here for early product builders. There’s also lessons from operating at Google’s scale as well, including how his approach to planning and org design have evolved.

Learn more about the Spotify “squads’ model that David mentioned in the org design section here: https://medium.com/pm101/spotify-squad-framework-part-i-8f74bcfcd761 

 

You can follow David on Twitter at @dflieb, and you can learn more about his approach to building products on First Round Review: https://firstround.com/review/cognitive-overhead-is-your-products-overlord-topple-it-with-these-tips/ 

 

You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

]]> 4170 no An inside look at the system that will outlast Bezos—Bill Carr & Colin Bryar on lessons from Amazon https://traffic.libsyn.com/secure/firstround/EP.12_-_Bill_and_Colin_FINAL.mp3 Today’s episode is with Bill Carr and Colin Bryar, two long-time Amazon executives who just published a new book, “Working Backwards,” which provides an inside look at how the leadership principles and business processes that have made the company so successful. Bill started at Amazon in 1999, and went on to launch and run the Prime Video, Amazon Studios, and Amazon Music businesses before he left the company in 2014. Colin joined Amazon in 1998, as the Director for Amazon Associates and Amazon Web Services Programs. He also spent two years as Jeff Bezos’ technical advisor or “shadow,” and later served as the COO for IMDb.com.  In today’s conversation, Bill and Colin take us through Amazon’s culture of innovation and the origin stories of the Kindle, AWS, and Prime businesses. From granular details about the “working backwards” process, to an inside look at how players like Jeff Bezos and incoming CEO Andy Jassy operated up close, they share invaluable insights on diving deep and operational excellence. Whether it’s their lessons on why innovation can’t be a part-time job, or the perils of taking a “skills-forward” approach to exploring new opportunities, or why mechanisms are more important than good intentions, there’s lots of food for thought in here for founders and startup leaders. Learn more about “Working Backwards” here You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson   Tue, 09 Feb 2021 10:30:00 -0000 full 10 First Round Former Amazon execs share an inside look at the company's leadership principles and business processes in their new book Today’s episode is with Bill Carr and Colin Bryar, two long-time Amazon executives who just published a new book, “Working Backwards,” which provides an inside look at how the leadership principles and business processes that have made the company so successful. Bill started at Amazon in 1999, and went on to launch and run the Prime Video, Amazon Studios, and Amazon Music businesses before he left the company in 2014. Colin joined Amazon in 1998, as the Director for Amazon Associates and Amazon Web Services Programs. He also spent two years as Jeff Bezos’ technical advisor or “shadow,” and later served as the COO for IMDb.com.  In today’s conversation, Bill and Colin take us through Amazon’s culture of innovation and the origin stories of the Kindle, AWS, and Prime businesses. From granular details about the “working backwards” process, to an inside look at how players like Jeff Bezos and incoming CEO Andy Jassy operated up close, they share invaluable insights on diving deep and operational excellence. Whether it’s their lessons on why innovation can’t be a part-time job, or the perils of taking a “skills-forward” approach to exploring new opportunities, or why mechanisms are more important than good intentions, there’s lots of food for thought in here for founders and startup leaders. Learn more about “Working Backwards” here You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson   Today’s episode is with Bill Carr and Colin Bryar, two long-time Amazon executives who just published a new book, “Working Backwards,” which provides an inside look at how the leadership principles and business processes that have made the company so successful.

Bill started at Amazon in 1999, and went on to launch and run the Prime Video, Amazon Studios, and Amazon Music businesses before he left the company in 2014. Colin joined Amazon in 1998, as the Director for Amazon Associates and Amazon Web Services Programs. He also spent two years as Jeff Bezos’ technical advisor or “shadow,” and later served as the COO for IMDb.com. 

In today’s conversation, Bill and Colin take us through Amazon’s culture of innovation and the origin stories of the Kindle, AWS, and Prime businesses. From granular details about the “working backwards” process, to an inside look at how players like Jeff Bezos and incoming CEO Andy Jassy operated up close, they share invaluable insights on diving deep and operational excellence.

Whether it’s their lessons on why innovation can’t be a part-time job, or the perils of taking a “skills-forward” approach to exploring new opportunities, or why mechanisms are more important than good intentions, there’s lots of food for thought in here for founders and startup leaders.

Learn more about “Working Backwards” here

You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  

]]> 4305 no From exec roles to board seats — Anne Raimondi’s leadership lessons for the startup C-Suite https://traffic.libsyn.com/secure/firstround/EP.11_-_Anne_Raimondi_FINAL.mp3 Today’s episode is with Anne Raimondi, Chief Customer Officer at Guru, and independent board member at Asana, Gusto and Patreon. Previously, she was part of the founding team at Blue Nile, spent five years in product marketing at eBay, and led marketing as an early employee at SurveyMonkey, before pivoting to operations as an SVP at Zendesk.  In today’s conversation, Anne pulls on threads from across her impressive career as a founder, operator, executive and board member to deliver spot-on advice for folks with an eye for the C-suite. From what enables the best executives to scale up, to how she’s approached her own 30, 60, 90-day plans as a brand-new hire — she doles out plenty of prescriptions for getting this critical transition right and avoiding common traps. She also opens up her playbook for approaching executive recruiting, interviewing and hiring, and when to mine executive talent internally rather than defaulting to external hires. Finally, she opens up about her board work, sharing the essential ingredients for productive, impactful boards across every growth stage.  Today’s conversation is a must-listen for executives, founders and board members looking to level up their leadership frameworks — and for folks who someday hope to step into these same shoes. You can follow Anne on Twitter at @anneraimondi and you can learn more about her approach to diagnosing and repairing team trust on First Round Review: https://firstround.com/review/use-this-equation-to-determine-diagnose-and-repair-trust/ You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  Thu, 04 Feb 2021 10:30:00 -0000 full 9 First Round Today’s episode is with Anne Raimondi, Chief Customer Officer at Guru, a knowledge management platform. Across her career in tech, Anne has been a founder, operator, executive and an independent board member at companies like eBay, SurveyMonkey, Zendesk Today’s episode is with Anne Raimondi, Chief Customer Officer at Guru, and independent board member at Asana, Gusto and Patreon. Previously, she was part of the founding team at Blue Nile, spent five years in product marketing at eBay, and led marketing as an early employee at SurveyMonkey, before pivoting to operations as an SVP at Zendesk.  In today’s conversation, Anne pulls on threads from across her impressive career as a founder, operator, executive and board member to deliver spot-on advice for folks with an eye for the C-suite. From what enables the best executives to scale up, to how she’s approached her own 30, 60, 90-day plans as a brand-new hire — she doles out plenty of prescriptions for getting this critical transition right and avoiding common traps. She also opens up her playbook for approaching executive recruiting, interviewing and hiring, and when to mine executive talent internally rather than defaulting to external hires. Finally, she opens up about her board work, sharing the essential ingredients for productive, impactful boards across every growth stage.  Today’s conversation is a must-listen for executives, founders and board members looking to level up their leadership frameworks — and for folks who someday hope to step into these same shoes. You can follow Anne on Twitter at @anneraimondi and you can learn more about her approach to diagnosing and repairing team trust on First Round Review: https://firstround.com/review/use-this-equation-to-determine-diagnose-and-repair-trust/ You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  Today’s episode is with Anne Raimondi, Chief Customer Officer at Guru, and independent board member at Asana, Gusto and Patreon. Previously, she was part of the founding team at Blue Nile, spent five years in product marketing at eBay, and led marketing as an early employee at SurveyMonkey, before pivoting to operations as an SVP at Zendesk. 

In today’s conversation, Anne pulls on threads from across her impressive career as a founder, operator, executive and board member to deliver spot-on advice for folks with an eye for the C-suite. From what enables the best executives to scale up, to how she’s approached her own 30, 60, 90-day plans as a brand-new hire — she doles out plenty of prescriptions for getting this critical transition right and avoiding common traps.

She also opens up her playbook for approaching executive recruiting, interviewing and hiring, and when to mine executive talent internally rather than defaulting to external hires. Finally, she opens up about her board work, sharing the essential ingredients for productive, impactful boards across every growth stage. 

Today’s conversation is a must-listen for executives, founders and board members looking to level up their leadership frameworks — and for folks who someday hope to step into these same shoes.

You can follow Anne on Twitter at @anneraimondi and you can learn more about her approach to diagnosing and repairing team trust on First Round Review: https://firstround.com/review/use-this-equation-to-determine-diagnose-and-repair-trust/

You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

]]> 4687 no Plaid & Dropbox’s Jean-Denis Grèze’s playbook for building an engineering culture of ownership https://traffic.libsyn.com/secure/firstround/EP.08_-_Jean-Denis_Greze_FINAL.mp3 Today’s episode is with Jean-Denis Grèze, Head of Engineering at Plaid, which securely connects your bank to your apps. Before joining Plaid, Jean-Denis served as Director of Engineering at Dropbox, and even had a stint in law school and one year as a lawyer under his belt before diving deep into the world of CS.  While he says becoming a lawyer was a “four-year detour he probably didn’t need,” there’s a lot to be said for how it’s shaped his engineering career and management philosophy. As he puts it, he strongly favors pragmatism over perfection, and it’s something he hammers home within his engineering teams. In today’s conversation, Jean-Denis pulls on threads from across his career to weave together a modern playbook for engineering leadership — and the hard-won lessons that stick with him. He also shares his insights on why his engineering org doesn’t have titles, the one question he asks every engineering manager candidate, and how his team prioritizes technical debt and keeping the lights on versus sexy, brand-new projects. Today’s conversation is a must-listen for technical leaders or those who are eyeing the engineering leadership track. From motivating a team to tracking the right KPIs, Jean-Denis has got tons of great tactics and stories from his time at Plaid and Dropbox for you to learn from. You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  Thu, 14 Jan 2021 10:30:00 -0000 full 8 First Round Today’s episode is with Jean-Denis Grèze, Head of Engineering at Plaid, which securely connects your bank to your apps like Venmo and Betterment. Before joining Plaid back in 2017, Jean-Denis was Director of Engineering at Dropbox and even took a 4-yea Today’s episode is with Jean-Denis Grèze, Head of Engineering at Plaid, which securely connects your bank to your apps. Before joining Plaid, Jean-Denis served as Director of Engineering at Dropbox, and even had a stint in law school and one year as a lawyer under his belt before diving deep into the world of CS.  While he says becoming a lawyer was a “four-year detour he probably didn’t need,” there’s a lot to be said for how it’s shaped his engineering career and management philosophy. As he puts it, he strongly favors pragmatism over perfection, and it’s something he hammers home within his engineering teams. In today’s conversation, Jean-Denis pulls on threads from across his career to weave together a modern playbook for engineering leadership — and the hard-won lessons that stick with him. He also shares his insights on why his engineering org doesn’t have titles, the one question he asks every engineering manager candidate, and how his team prioritizes technical debt and keeping the lights on versus sexy, brand-new projects. Today’s conversation is a must-listen for technical leaders or those who are eyeing the engineering leadership track. From motivating a team to tracking the right KPIs, Jean-Denis has got tons of great tactics and stories from his time at Plaid and Dropbox for you to learn from. You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  Today’s episode is with Jean-Denis Grèze, Head of Engineering at Plaid, which securely connects your bank to your apps. Before joining Plaid, Jean-Denis served as Director of Engineering at Dropbox, and even had a stint in law school and one year as a lawyer under his belt before diving deep into the world of CS. 

While he says becoming a lawyer was a “four-year detour he probably didn’t need,” there’s a lot to be said for how it’s shaped his engineering career and management philosophy. As he puts it, he strongly favors pragmatism over perfection, and it’s something he hammers home within his engineering teams. In today’s conversation, Jean-Denis pulls on threads from across his career to weave together a modern playbook for engineering leadership — and the hard-won lessons that stick with him.

He also shares his insights on why his engineering org doesn’t have titles, the one question he asks every engineering manager candidate, and how his team prioritizes technical debt and keeping the lights on versus sexy, brand-new projects.

Today’s conversation is a must-listen for technical leaders or those who are eyeing the engineering leadership track. From motivating a team to tracking the right KPIs, Jean-Denis has got tons of great tactics and stories from his time at Plaid and Dropbox for you to learn from.

You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

]]> 3411 no Upstart just went public — CEO Dave Girouard shares why it isn’t a typical success story https://traffic.libsyn.com/secure/firstround/EP.07_-_Dave_Girouard_FINAL.mp3 Today’s episode is with Dave Girouard, the CEO and co-founder of Upstart, an AI-powered lending platform that recently went public. Before founding Upstart, Dave was President of Google Enterprise, and spent 8 years building Google's billion dollar cloud apps business. Here at First Round, we first came to know Dave when we invested in Upstart’s seed round back in 2012, and we’ve found him to be one of the most tenacious and focused founders we’ve ever backed. In today’s conversation, Dave gives us an inside look at how the business was built and what other startups can learn from its early days. In addition to unpacking the initial idea and subsequent business model pivot, Dave gets into what it felt like flying under the radar of Silicon Valley, why he “sucked at fundraising,” and how he and his co-founders have stuck together for almost a decade.  From his “Are you Airbnb or Paypal?” test and why you should look at your career in landscape mode, to the three mental models he leans on to manage his psychology as a founder, Dave shares helpful frameworks that any startup leader can learn from. We also dive into his “management by exception” philosophy, what he learned from Google, how he runs his leadership team, and why he leans on references, not interviews, when hiring execs.   You can follow Dave on Twitter at @davegirouard and you can read his First Round Review articles that we mentioned in the episode here:  https://firstround.com/review/speed-as-a-habit/  https://firstround.com/review/how-does-your-leadership-team-rate/  https://firstround.com/review/a-founders-guide-to-writing-well/    You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  Tue, 22 Dec 2020 10:30:00 -0000 full 7 First Round Today’s episode is with Dave Girouard, the CEO and co-founder of Upstart, an AI-powered lending platform that recently went public. First Round invested in Upstart’s seed round back in 2012, so we were thrilled to chat with Dave about his lessons from Today’s episode is with Dave Girouard, the CEO and co-founder of Upstart, an AI-powered lending platform that recently went public. Before founding Upstart, Dave was President of Google Enterprise, and spent 8 years building Google's billion dollar cloud apps business. Here at First Round, we first came to know Dave when we invested in Upstart’s seed round back in 2012, and we’ve found him to be one of the most tenacious and focused founders we’ve ever backed. In today’s conversation, Dave gives us an inside look at how the business was built and what other startups can learn from its early days. In addition to unpacking the initial idea and subsequent business model pivot, Dave gets into what it felt like flying under the radar of Silicon Valley, why he “sucked at fundraising,” and how he and his co-founders have stuck together for almost a decade.  From his “Are you Airbnb or Paypal?” test and why you should look at your career in landscape mode, to the three mental models he leans on to manage his psychology as a founder, Dave shares helpful frameworks that any startup leader can learn from. We also dive into his “management by exception” philosophy, what he learned from Google, how he runs his leadership team, and why he leans on references, not interviews, when hiring execs.   You can follow Dave on Twitter at @davegirouard and you can read his First Round Review articles that we mentioned in the episode here:  https://firstround.com/review/speed-as-a-habit/  https://firstround.com/review/how-does-your-leadership-team-rate/  https://firstround.com/review/a-founders-guide-to-writing-well/    You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  Today’s episode is with Dave Girouard, the CEO and co-founder of Upstart, an AI-powered lending platform that recently went public. Before founding Upstart, Dave was President of Google Enterprise, and spent 8 years building Google's billion dollar cloud apps business.

Here at First Round, we first came to know Dave when we invested in Upstart’s seed round back in 2012, and we’ve found him to be one of the most tenacious and focused founders we’ve ever backed. In today’s conversation, Dave gives us an inside look at how the business was built and what other startups can learn from its early days.

In addition to unpacking the initial idea and subsequent business model pivot, Dave gets into what it felt like flying under the radar of Silicon Valley, why he “sucked at fundraising,” and how he and his co-founders have stuck together for almost a decade. 

From his “Are you Airbnb or Paypal?” test and why you should look at your career in landscape mode, to the three mental models he leans on to manage his psychology as a founder, Dave shares helpful frameworks that any startup leader can learn from. We also dive into his “management by exception” philosophy, what he learned from Google, how he runs his leadership team, and why he leans on references, not interviews, when hiring execs.

 

You can follow Dave on Twitter at @davegirouard and you can read his First Round Review articles that we mentioned in the episode here: 

https://firstround.com/review/speed-as-a-habit/ 

https://firstround.com/review/how-does-your-leadership-team-rate/ 

https://firstround.com/review/a-founders-guide-to-writing-well/ 

 

You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

]]> 3806 no Unpacking all the non-consensus moves in Atlassian’s story — Jay Simons https://traffic.libsyn.com/secure/firstround/EP.06_-_Jay_Simons_FINAL.mp3 Today’s episode is with Jay Simons, who’s currently a partner at Bond and serves on the boards of Hubspot and Zapier. But before that, he had a long run as the President of Atlassian, which develops software collaboration tools like Jira, Confluence and Trello. In today’s conversation, Jay dives into Atlassian’s growth story, from what’s misunderstood or not talked about enough, to the strategic choices that went against the grain. He shares an inside look at how Atlassian built a product that can sell itself and deferred short-term openings for more durable long-term opportunity. In addition to unpacking what he calls their “three-legged stool” of self-service, a global network of channel partners, and eventual enterprise upselling, Jay gives us a deep dive into their pricing strategy and how they thought about exploring adjacent product areas. From spinning the flywheels of a remarkable product and a high-velocity self-service funnel, to building a culture that focuses on first principles, there’s tons of great advice in here — not only for go-to-market and revenue leaders, but for anyone who works at a startup. This blog post from Intercom has the flywheel graphic that Jay mentioned in the episode. https://www.intercom.com/blog/podcasts/scale-how-atlassian-built-a-20-billion-dollar-company-with-no-sales-team/  You can follow Jay on Twitter at @jaysimons. You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  Thu, 17 Dec 2020 10:30:00 -0000 full 6 First Round Today’s episode is with Jay Simons, who spent the last 12 years as the president of Atlassian, overseeing go-to-market strategy and big acquisitions as the company went from startup to IPO. He digs into their unconventional moves, such as using channel Today’s episode is with Jay Simons, who’s currently a partner at Bond and serves on the boards of Hubspot and Zapier. But before that, he had a long run as the President of Atlassian, which develops software collaboration tools like Jira, Confluence and Trello. In today’s conversation, Jay dives into Atlassian’s growth story, from what’s misunderstood or not talked about enough, to the strategic choices that went against the grain. He shares an inside look at how Atlassian built a product that can sell itself and deferred short-term openings for more durable long-term opportunity. In addition to unpacking what he calls their “three-legged stool” of self-service, a global network of channel partners, and eventual enterprise upselling, Jay gives us a deep dive into their pricing strategy and how they thought about exploring adjacent product areas. From spinning the flywheels of a remarkable product and a high-velocity self-service funnel, to building a culture that focuses on first principles, there’s tons of great advice in here — not only for go-to-market and revenue leaders, but for anyone who works at a startup. This blog post from Intercom has the flywheel graphic that Jay mentioned in the episode. https://www.intercom.com/blog/podcasts/scale-how-atlassian-built-a-20-billion-dollar-company-with-no-sales-team/  You can follow Jay on Twitter at @jaysimons. You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  Today’s episode is with Jay Simons, who’s currently a partner at Bond and serves on the boards of Hubspot and Zapier. But before that, he had a long run as the President of Atlassian, which develops software collaboration tools like Jira, Confluence and Trello.

In today’s conversation, Jay dives into Atlassian’s growth story, from what’s misunderstood or not talked about enough, to the strategic choices that went against the grain. He shares an inside look at how Atlassian built a product that can sell itself and deferred short-term openings for more durable long-term opportunity.

In addition to unpacking what he calls their “three-legged stool” of self-service, a global network of channel partners, and eventual enterprise upselling, Jay gives us a deep dive into their pricing strategy and how they thought about exploring adjacent product areas. From spinning the flywheels of a remarkable product and a high-velocity self-service funnel, to building a culture that focuses on first principles, there’s tons of great advice in here — not only for go-to-market and revenue leaders, but for anyone who works at a startup.

This blog post from Intercom has the flywheel graphic that Jay mentioned in the episode. https://www.intercom.com/blog/podcasts/scale-how-atlassian-built-a-20-billion-dollar-company-with-no-sales-team/ 

You can follow Jay on Twitter at @jaysimons.

You can email us questions directly at review@firstround.com or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

]]> 4607 no Partnerships lessons from Stripe & Notion — Cristina Cordova on creating win-win deals https://traffic.libsyn.com/secure/firstround/EP.05_-_Cristina_Cordova_FINAL.mp3 Today’s episode is with Cristina Cordova, Notion’s Head of Platform & Partnerships. Previously, she was the 28th employee and the first partnerships hire at Stripe, where she cultivated partnerships with companies like Shopify, Squarespace and Apple, built out the BD org, and led their new Corporate Card effort.  After a decade in partnerships, Cristina has bagged big deals, honed her negotiation skills, built out teams — and made plenty of mistakes she hopes others can learn from. In today’s conversation, Cristina pulls from across her career to share the inside scoop on deals that had an unexpected outsized impact — as well as the ones that went sideways.  She also shares her playbook for being a startup’s first partnership hire, including the three critical areas to focus on first, and the common traps to avoid. It’s also full of actionable tactics on everything from dealing with partners trying to push you around, to how to hire for partnerships roles and structure the org chart. Today’s conversation is a must-listen of course for folks currently in or hoping to break into partnerships, platform or BD roles, but Cristina also shares great tactics for getting better at negotiating, as well as some fascinating stories of how Stripe and Notion scaled — meaning there’s tons to learn here for everyone. You can follow Cristina on Twitter at @cjc. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson  Thu, 10 Dec 2020 10:30:00 -0000 full 5 First Round Today’s episode is with Cristina Cordova, who spent 7 years at Stripe (as the 28th employee and first partnerships hire), and is now the Head of Platform & Partnerships at Notion. Cristina is full of actionable tactics on crafting win-win deals and buil Today’s episode is with Cristina Cordova, Notion’s Head of Platform & Partnerships. Previously, she was the 28th employee and the first partnerships hire at Stripe, where she cultivated partnerships with companies like Shopify, Squarespace and Apple, built out the BD org, and led their new Corporate Card effort.  After a decade in partnerships, Cristina has bagged big deals, honed her negotiation skills, built out teams — and made plenty of mistakes she hopes others can learn from. In today’s conversation, Cristina pulls from across her career to share the inside scoop on deals that had an unexpected outsized impact — as well as the ones that went sideways.  She also shares her playbook for being a startup’s first partnership hire, including the three critical areas to focus on first, and the common traps to avoid. It’s also full of actionable tactics on everything from dealing with partners trying to push you around, to how to hire for partnerships roles and structure the org chart. Today’s conversation is a must-listen of course for folks currently in or hoping to break into partnerships, platform or BD roles, but Cristina also shares great tactics for getting better at negotiating, as well as some fascinating stories of how Stripe and Notion scaled — meaning there’s tons to learn here for everyone. You can follow Cristina on Twitter at @cjc. You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson  Today’s episode is with Cristina Cordova, Notion’s Head of Platform & Partnerships. Previously, she was the 28th employee and the first partnerships hire at Stripe, where she cultivated partnerships with companies like Shopify, Squarespace and Apple, built out the BD org, and led their new Corporate Card effort. 

After a decade in partnerships, Cristina has bagged big deals, honed her negotiation skills, built out teams — and made plenty of mistakes she hopes others can learn from. In today’s conversation, Cristina pulls from across her career to share the inside scoop on deals that had an unexpected outsized impact — as well as the ones that went sideways. 

She also shares her playbook for being a startup’s first partnership hire, including the three critical areas to focus on first, and the common traps to avoid. It’s also full of actionable tactics on everything from dealing with partners trying to push you around, to how to hire for partnerships roles and structure the org chart.

Today’s conversation is a must-listen of course for folks currently in or hoping to break into partnerships, platform or BD roles, but Cristina also shares great tactics for getting better at negotiating, as well as some fascinating stories of how Stripe and Notion scaled — meaning there’s tons to learn here for everyone.

You can follow Cristina on Twitter at @cjc.

You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

]]> 4787 no Start with the story — Drift’s David Cancel on lessons he’s learned as a 5X founder https://traffic.libsyn.com/secure/firstround/EP.04_-_David_Cancel_FINAL.mp3 Today’s episode is with David Cancel. David has been a CEO and founder of multiple different companies throughout his career. He’s also been a software engineer, a serial CTO, and the Chief Product Officer at Hubspot, giving him a unique lens into company building and leadership at different levels. In today’s conversation, David unpacks those lessons and tells us why he’s so focused on storytelling these days as the co-founder and CEO of Drift, a conversational marketing and sales platform. From screenplay writing inspiration, to how storytelling training is part of their onboarding, David shares how they teach storytelling and drive narrative internally at Drift. He also shares tactical advice for engaging with exec teams and getting better at zooming in and out as CEO, as well as some really tactical frameworks, including Charlie Munger’s practice of inversion, the weekly rituals Drift relies on, and how they use asynchronous video communication. It’s a must-listen for current founders and CEOs, and anyone looking to level up their leadership skills.   You can follow David on Twitter at @dcancel. He also pens a popular newsletter called “The One Thing,” and hosts a great podcast called “Seeking Wisdom”  For reference, the books he mentioned in the episode include Jon Kabat-Zinn’s work on mindful meditation, and “The Passion Paradox” by Brad Stulberg.  To learn more about how Drift approaches storytelling, check out this article David wrote for Inc: https://www.inc.com/david-cancel/five-storytelling-tips-to-better-communicate-your-brand-message.html  To learn more about Charlie Munger’s concept of inversion that David mentioned, check out this Farnam Street post: https://fs.blog/2013/10/inversion/ You can email us questions directly at review@firstround.com or follow us on Twitter @firstround (twitter.com/firstround) and @brettberson (twitter.com/brettberson)  Thu, 03 Dec 2020 10:30:00 -0000 full 4 First Round Today’s episode is with David Cancel, co-founder and CEO of Drift, a conversational marketing and sales platform. This 5X founder has also been a serial CTO and the Chief Product Officer at Hubspot, giving him a unique perspective on leadership. In addi Today’s episode is with David Cancel. David has been a CEO and founder of multiple different companies throughout his career. He’s also been a software engineer, a serial CTO, and the Chief Product Officer at Hubspot, giving him a unique lens into company building and leadership at different levels. In today’s conversation, David unpacks those lessons and tells us why he’s so focused on storytelling these days as the co-founder and CEO of Drift, a conversational marketing and sales platform. From screenplay writing inspiration, to how storytelling training is part of their onboarding, David shares how they teach storytelling and drive narrative internally at Drift. He also shares tactical advice for engaging with exec teams and getting better at zooming in and out as CEO, as well as some really tactical frameworks, including Charlie Munger’s practice of inversion, the weekly rituals Drift relies on, and how they use asynchronous video communication. It’s a must-listen for current founders and CEOs, and anyone looking to level up their leadership skills.   You can follow David on Twitter at @dcancel. He also pens a popular newsletter called “The One Thing,” and hosts a great podcast called “Seeking Wisdom”  For reference, the books he mentioned in the episode include Jon Kabat-Zinn’s work on mindful meditation, and “The Passion Paradox” by Brad Stulberg.  To learn more about how Drift approaches storytelling, check out this article David wrote for Inc: https://www.inc.com/david-cancel/five-storytelling-tips-to-better-communicate-your-brand-message.html  To learn more about Charlie Munger’s concept of inversion that David mentioned, check out this Farnam Street post: https://fs.blog/2013/10/inversion/ You can email us questions directly at review@firstround.com or follow us on Twitter @firstround (twitter.com/firstround) and @brettberson (twitter.com/brettberson)  Today’s episode is with David Cancel. David has been a CEO and founder of multiple different companies throughout his career. He’s also been a software engineer, a serial CTO, and the Chief Product Officer at Hubspot, giving him a unique lens into company building and leadership at different levels.

In today’s conversation, David unpacks those lessons and tells us why he’s so focused on storytelling these days as the co-founder and CEO of Drift, a conversational marketing and sales platform. From screenplay writing inspiration, to how storytelling training is part of their onboarding, David shares how they teach storytelling and drive narrative internally at Drift.

He also shares tactical advice for engaging with exec teams and getting better at zooming in and out as CEO, as well as some really tactical frameworks, including Charlie Munger’s practice of inversion, the weekly rituals Drift relies on, and how they use asynchronous video communication.

It’s a must-listen for current founders and CEOs, and anyone looking to level up their leadership skills.

 

You can follow David on Twitter at @dcancel. He also pens a popular newsletter called “The One Thing,” and hosts a great podcast called “Seeking Wisdom” 

For reference, the books he mentioned in the episode include Jon Kabat-Zinn’s work on mindful meditation, and “The Passion Paradox” by Brad Stulberg. 

To learn more about how Drift approaches storytelling, check out this article David wrote for Inc:

https://www.inc.com/david-cancel/five-storytelling-tips-to-better-communicate-your-brand-message.html 

To learn more about Charlie Munger’s concept of inversion that David mentioned, check out this Farnam Street post: https://fs.blog/2013/10/inversion/

You can email us questions directly at review@firstround.com or follow us on Twitter @firstround (twitter.com/firstround) and @brettberson (twitter.com/brettberson) 

]]> 3030 no Lessons from a first-time CEO — Steve El-Hage on learning everything the hard way https://traffic.libsyn.com/secure/firstround/EP.03_-_Steve_El-Hage_FINAL.mp3 Our third episode is with Steve El-Hage, co-founder and CEO of Drop, an electronics company that creates products powered by feedback by a massive community of enthusiasts and experts. Reflecting on his 8-year, heads-down grind since becoming a first-time founder at 22, Steve shares the lessons that he figured out the hard way, from revenue dropping off a cliff and painful pivots, to hiring blunders and severe burnout. Thu, 19 Nov 2020 10:30:00 -0000 full 3 First Round Our third episode is with Steve El-Hage, Founder and CEO of Drop (formerly Massdrop). Drop is an electronics brand that creates products based on feedback from enthusiast communities. Steve and Drop aren’t household names — you’ve very likely... Our third episode is with Steve El-Hage, co-founder and CEO of Drop, an electronics company that creates products powered by feedback by a massive community of enthusiasts and experts. Reflecting on his 8-year, heads-down grind since becoming a first-time founder at 22, Steve shares the lessons that he figured out the hard way, from revenue dropping off a cliff and painful pivots, to hiring blunders and severe burnout. 5531 no Product lessons from Cash App & Carbon Health — Ayo Omojola on going “unreasonably deep” https://review.firstround.com/podcast Our second episode is with Ayo Omojola, VP of Product at Carbon Health. Previously, he was the founding product manager on the banking team for Cash App at Square, where he co-created the Cash Card and helped build out Square’s technical banking infrastructure. He’s also a former founder of a Y Combinator-backed startup and an active angel investor, which gives him a unique lens into finding and evaluating startup ideas. Tapping into Ayo’s experience working in the heavily regulated spaces of healthcare and financial services, we dive into how he untangles regulations to find “the opportunities where it’s easy to stop” and goes “unreasonably deep” when building early products. Ayo thinks a lot about problem selection and makes the case for putting more effort into choosing what to work on. It’s a must-listen for anyone who’s thinking about starting a company someday, or a product leader who hopes to help a new product take shape. But even if those aren’t goals of yours, there’s still tons to learn. Ayo shares the individuals he learned the most from during his time at Square and the frameworks he picked up from them, such as on how to get better at process, setting context, and “optimizing for the outstanding.” Last but not least, we get into his management and hiring philosophy, including why he loves to hire former founders. You can follow Ayo on Twitter at @ay_o. For reference, the leaders he gave a shout out to in the episode include Robert Andersen (the founding designer at Square), Dhanji Prasanna (who led engineering for Cash App), Jim Esposito (Operations Lead for Cash App) and Emily Chiu (who led strategic development efforts for Cash App). You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Thu, 12 Nov 2020 10:30:00 -0000 full 2 First Round Our second episode is with Ayo Omojola, VP of Product at Carbon Health and the founding product manager for Cash App at Square, where he co-created the Cash Card. Tapping into his experience working in heavily regulated spaces, we dive into how he finds s Our second episode is with Ayo Omojola, VP of Product at Carbon Health. Previously, he was the founding product manager on the banking team for Cash App at Square, where he co-created the Cash Card and helped build out Square’s technical banking infrastructure. He’s also a former founder of a Y Combinator-backed startup and an active angel investor, which gives him a unique lens into finding and evaluating startup ideas. Tapping into Ayo’s experience working in the heavily regulated spaces of healthcare and financial services, we dive into how he untangles regulations to find “the opportunities where it’s easy to stop” and goes “unreasonably deep” when building early products. Ayo thinks a lot about problem selection and makes the case for putting more effort into choosing what to work on. It’s a must-listen for anyone who’s thinking about starting a company someday, or a product leader who hopes to help a new product take shape. But even if those aren’t goals of yours, there’s still tons to learn. Ayo shares the individuals he learned the most from during his time at Square and the frameworks he picked up from them, such as on how to get better at process, setting context, and “optimizing for the outstanding.” Last but not least, we get into his management and hiring philosophy, including why he loves to hire former founders. You can follow Ayo on Twitter at @ay_o. For reference, the leaders he gave a shout out to in the episode include Robert Andersen (the founding designer at Square), Dhanji Prasanna (who led engineering for Cash App), Jim Esposito (Operations Lead for Cash App) and Emily Chiu (who led strategic development efforts for Cash App). You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Our second episode is with Ayo Omojola, VP of Product at Carbon Health. Previously, he was the founding product manager on the banking team for Cash App at Square, where he co-created the Cash Card and helped build out Square’s technical banking infrastructure. He’s also a former founder of a Y Combinator-backed startup and an active angel investor, which gives him a unique lens into finding and evaluating startup ideas.

Tapping into Ayo’s experience working in the heavily regulated spaces of healthcare and financial services, we dive into how he untangles regulations to find “the opportunities where it’s easy to stop” and goes “unreasonably deep” when building early products. Ayo thinks a lot about problem selection and makes the case for putting more effort into choosing what to work on. It’s a must-listen for anyone who’s thinking about starting a company someday, or a product leader who hopes to help a new product take shape.

But even if those aren’t goals of yours, there’s still tons to learn. Ayo shares the individuals he learned the most from during his time at Square and the frameworks he picked up from them, such as on how to get better at process, setting context, and “optimizing for the outstanding.” Last but not least, we get into his management and hiring philosophy, including why he loves to hire former founders.

You can follow Ayo on Twitter at @ay_o. For reference, the leaders he gave a shout out to in the episode include Robert Andersen (the founding designer at Square), Dhanji Prasanna (who led engineering for Cash App), Jim Esposito (Operations Lead for Cash App) and Emily Chiu (who led strategic development efforts for Cash App).

You can email us questions directly at review@firstround.com or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

]]> 4311 no Molly Graham’s management lessons from Google, Facebook, Quip & Lambda School https://review.firstround.com/podcast Our first episode is with Molly Graham, a seasoned exec and builder who particularly excels at helping startups to go not from 0 to 1, but from 1 to 2. We’ve interviewed her four times on First Round Review — which might be a record — because the advice she has to share and the experiences she can draw from are unbelievably helpful to founders and startup leaders. She helped build and scale Facebook, Quip, The Chan Zuckerberg Initiative in their early days, and is now the COO of Lambda School. While on The Review she’s shared advice on everything from managing your emotions and struggling with scaling, to codifying your culture and setting up your first comp system, today’s conversation is focused on a different topic — management.  This is a topic Molly has strong opinions on—she’s seen time and time again across her career how so many startup mistakes come down to general management issues. We cover everything from the traps that are easy to fall into, to why you should be spending more time with your highest—not your lowest—performers, to the managers she’s learned the most from, so there’s tons of insightful advice and practical tactics for both first-time managers and seasoned leaders alike. You can read more about Molly’s approach to scaling startups on First Round Review. We particularly recommend following her advice to ‘give away your Legos’ https://firstround.com/review/give-away-your-legos-and-other-commandments-for-scaling-startups/ And here’s the article on compensation that Molly mentioned in the interview: https://firstround.com/review/A-Counterintuitive-System-for-Startup-Compensation/    You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson  Thu, 29 Oct 2020 09:30:00 -0000 full 1 First Round Our first episode is with Molly Graham, who helped scale Facebook, Quip, The Chan Zuckerberg Initiative in their early days, and is now the COO of Lambda School. We dive into her thoughts on management, from the traps that are easy to fall into, to why yo Our first episode is with Molly Graham, a seasoned exec and builder who particularly excels at helping startups to go not from 0 to 1, but from 1 to 2. We’ve interviewed her four times on First Round Review — which might be a record — because the advice she has to share and the experiences she can draw from are unbelievably helpful to founders and startup leaders. She helped build and scale Facebook, Quip, The Chan Zuckerberg Initiative in their early days, and is now the COO of Lambda School. While on The Review she’s shared advice on everything from managing your emotions and struggling with scaling, to codifying your culture and setting up your first comp system, today’s conversation is focused on a different topic — management.  This is a topic Molly has strong opinions on—she’s seen time and time again across her career how so many startup mistakes come down to general management issues. We cover everything from the traps that are easy to fall into, to why you should be spending more time with your highest—not your lowest—performers, to the managers she’s learned the most from, so there’s tons of insightful advice and practical tactics for both first-time managers and seasoned leaders alike. You can read more about Molly’s approach to scaling startups on First Round Review. We particularly recommend following her advice to ‘give away your Legos’ https://firstround.com/review/give-away-your-legos-and-other-commandments-for-scaling-startups/ And here’s the article on compensation that Molly mentioned in the interview: https://firstround.com/review/A-Counterintuitive-System-for-Startup-Compensation/    You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson  Our first episode is with Molly Graham, a seasoned exec and builder who particularly excels at helping startups to go not from 0 to 1, but from 1 to 2. We’ve interviewed her four times on First Round Review — which might be a record — because the advice she has to share and the experiences she can draw from are unbelievably helpful to founders and startup leaders. She helped build and scale Facebook, Quip, The Chan Zuckerberg Initiative in their early days, and is now the COO of Lambda School.

While on The Review she’s shared advice on everything from managing your emotions and struggling with scaling, to codifying your culture and setting up your first comp system, today’s conversation is focused on a different topic — management. 

This is a topic Molly has strong opinions on—she’s seen time and time again across her career how so many startup mistakes come down to general management issues. We cover everything from the traps that are easy to fall into, to why you should be spending more time with your highest—not your lowest—performers, to the managers she’s learned the most from, so there’s tons of insightful advice and practical tactics for both first-time managers and seasoned leaders alike.

You can read more about Molly’s approach to scaling startups on First Round Review. We particularly recommend following her advice to ‘give away your Legos’ https://firstround.com/review/give-away-your-legos-and-other-commandments-for-scaling-startups/

And here’s the article on compensation that Molly mentioned in the interview: https://firstround.com/review/A-Counterintuitive-System-for-Startup-Compensation/ 

 

You can email us questions directly at review@firstround.com or follow us on Twitter @firstround and @brettberson 

]]> 4588 no Preview of In Depth from First Round https://traffic.libsyn.com/secure/firstround/EP.00_Welcome_to_In_Depth_FINAL.mp3 Welcome to In Depth, a new podcast from First Round Review that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves. We’ll cover a lot of ground and a wide range of topics, from hiring executives and becoming a better manager, to the importance of storytelling inside of your organization. But every interview will hit the level of tactical depth where the very best advice is found. I hope you’ll join us. Subscribe to “In Depth” now and learn more at firstround.com Thu, 15 Oct 2020 01:19:00 -0000 trailer First Round Welcome to In Depth, a new podcast from First Round Review that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves. We’ll cover a lot of ground and a wide range of... Welcome to In Depth, a new podcast from First Round Review that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves. We’ll cover a lot of ground and a wide range of topics, from hiring executives and becoming a better manager, to the importance of storytelling inside of your organization. But every interview will hit the level of tactical depth where the very best advice is found. I hope you’ll join us. Subscribe to “In Depth” now and learn more at firstround.com Welcome to In Depth, a new podcast from First Round Review that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves.

We’ll cover a lot of ground and a wide range of topics, from hiring executives and becoming a better manager, to the importance of storytelling inside of your organization. But every interview will hit the level of tactical depth where the very best advice is found.

I hope you’ll join us. Subscribe to “In Depth” now and learn more at firstround.com

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