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Executive Function: Building systems that can make decisions without you | Jeanne DeWitt Grosser (COO, Vercel)
Executive Function

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.
Applied Intuition’s Path to Product-Market Fit — The $15B Founder’s Formula for a Winning Company
Product

Applied Intuition’s Path to Product-Market Fit — The $15B Founder’s Formula for a Winning Company

Co-founder and CEO Qasar Younis lays out the personal and business moves he's made to build a company only he could start.
Gusto’s Path to Product-Market Fit — How Listening to Customers Built a $9.6B Company
Product

Gusto’s Path to Product-Market Fit — How Listening to Customers Built a $9.6B Company

Cold-calling from a walk-in closet taught Tomer London how to recognize what PMF really feels like.
Canva’s Path to Product-Market Fit — How a Two-Hour Founder Date Led To a $42B Design Platform
Product

Canva’s Path to Product-Market Fit — How a Two-Hour Founder Date Led To a $42B Design Platform

Cameron Adams goes deep on finding early evangelists, the unconventional tactics that led to massive growth, and more.
The 30 Best Pieces of Company Building Advice We Heard in 2025
Must-reads

The 30 Best Pieces of Company Building Advice We Heard in 2025

A roundup of the standout startup wisdom we collected last year.
The Merger Playbook: Crossbeam’s CEO Breaks Down Every Detail of the Deal That Worked
Product

The Merger Playbook: Crossbeam’s CEO Breaks Down Every Detail of the Deal That Worked

A founder's firsthand account of how he merged with a competitor to materially change the trajectory of his company.
What’s in a Name? A Lot, Actually. Here’s How to Pick the Right One For Your Company
Starting Up

What’s in a Name? A Lot, Actually. Here’s How to Pick the Right One For Your Company

A playbook for picking a name that actually fits your company (and all the logistics that come with naming you may not be thinking about).
The Other PMF: Wes Kao’s Framework for Founders Who Want to Communicate — and Lead — Better
Management

The Other PMF: Wes Kao’s Framework for Founders Who Want to Communicate — and Lead — Better

Tactical advice for founders on mastering “personality-message fit": leaning into your natural communication style.
Sentry's Path to Product-Market Fit — A High School Dropout Turned an Open-Source Project into a $3B Company
Product

Sentry's Path to Product-Market Fit — A High School Dropout Turned an Open-Source Project into a $3B Company

From Burger King shifts to a billion-dollar business, Sentry co-founder and CPO David Cramer shares his lessons for early stage founders.
When Should You Stop Clinging to Product and Hire Your First PM? Advice From a Founder and CPO
Product

When Should You Stop Clinging to Product and Hire Your First PM? Advice From a Founder and CPO

Saumil Mehta outlines a framework for early-stage founders on timing the first product manager hire.
Mercury’s Path to Product-Market Fit — Do the Hard Part First
Product

Mercury’s Path to Product-Market Fit — Do the Hard Part First

Serial founder Immad Akhund shares what he's learned about finding product-market fit from his fourth act, Mercury.
What Early Stage Founders Should Know About Comp: The Rules To Break (And A Few You Should Actually Follow)
Starting Up

What Early Stage Founders Should Know About Comp: The Rules To Break (And A Few You Should Actually Follow)

There’s no shortage of advice on how to structure compensation. Here’s how to know which of it applies to you — with insights from Clay, Google and Instacart.
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For the founder's notepad:
"If you personally want to grow as fast as your company, you have to give away your job every couple months." – Molly Graham
“Asking ‘Why can't this be done sooner?’ methodically, reliably and habitually can have a profound impact on the speed of your organization.” – Dave Girouard
“End every meeting or conversation with the feeling and optimism you’d like to have at the start of your next conversation with the person.” – Chris Fralic
“Focus is doing things with a clear intention. It doesn’t mean you charge single-minded toward a goal. It means you pay rapt and incremental attention to how you need to turn the rudder on a project.” – Fidji Simo
“It’s essential to grow with the company — rather than having the company grow around you.” – Cristina Cordova 
“You have to be impatient with shipping, but patient with your career.” – James Everingham
“‘I trust you, make the call’ might be the six most powerful words you can hear from a manager.” – Sean Twersky
“Your job as a CEO is to build fire departments, not put out fires.” – Sam Corcos 
“Can you say with confidence that each report would want to be on your team again? If you aren’t sure that the answer is yes, it’s probably no — much like how if you have to ask, ‘Am I in love?’ you’re probably not.” – Julie Zhuo 
“People can get addicted to yak shaving. An effective engineering generalist knows when to move on. Pay attention to whether they used their time wisely, not just the results.” – Mike Krieger 
“It sounds so simple to say that bosses need to tell employees when they're screwing up. But it very rarely happens.” – Kim Scott
“You’ll know you understand the customer problem enough when you can predict 75% of what a customer tells you. Keep having these conversations until three-quarters of it is stuff you already know.” – Christina Cacioppo
“I have a rule: no company swag until the business has at least $250K of revenue or 250k users. Until then, you don’t get to “feel” the benefits of having started a company.” – Gagan Biyani
“The business model ends up becoming the business. It’s equally important as the market you’re going after and the product that you build.” – Jay Simons 
“If speed is the yin, the yang is prioritization. You can’t be fast if you don’t know what’s important.” – Jaleh Rezaei
“If you treat your connections as a kind of personal ATM you use for frequent withdrawals, you’ll quickly be disappointed (and overdrawn).” – Karen Wickre 
“Delighting the customer always yields better returns than countering or copying a competitor. It’s just a lot harder to do.” – Andy Rachleff 
“When you’re a founder, every moment you’re not writing code or getting users, you need to be making a conscious choice: Is whatever you’re doing worth your time?” – Alexis Ohanian
“‘Why would a customer not want this?’ is often a far more interesting question than why they would.” – Rick Song
“When you leave the planning process wondering if you put too many resources behind a single bet, that’s the bet that ends up succeeding. Bold ideas need bold resourcing.” – Lenny Rachitsky and Nels Gilbreth
“Treat customer development as a one-on-one with a direct report — you just want to ask the hard questions.” – Ryan Glasgow
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