Ryan Caldbeck (@ryan_caldbeck) / X

Ryan Caldbeck

5,410 posts

Ryan Caldbeck

@ryan_caldbeck

Founder, CEO, Board Member Starting something new

San Francisco Bay Area, CA

Joined August 2015

Ryan Caldbeck
@ryan_caldbeck
Mar 25, 2018
1/ In honor of all the CEOs who have told me they are "crushing it," and that they “can’t keep up with the growth” - I’d like to put forward just some of the many many mistakes I’ve made as CEO. Some were bad for @CircleUp , some were just embarrassing:
Ryan Caldbeck
@ryan_caldbeck
Oct 15, 2020
1/ Tuesday was my last day as CEO of @CircleUp. I’ve been CEO since starting the co. in 2011 with my co-founder @roryeakin. This is a thread about what happened, why and my emotions about it. For more detail: ryancaldbeck.medium.com/transitions-fa… Much of this I have never talked about.
Transitions
From ryancaldbeck.medium.com
Ryan Caldbeck
@ryan_caldbeck
May 27, 2018
1/ I believe there are things that CEOs almost universally feel, but are afraid to talk about, making this journey as a CEO lonelier and less healthy. I recently had an amazing dialogue with some other CEOs about these topics. I wanted to broaden the conversation publicly.
Ryan Caldbeck
@ryan_caldbeck
Apr 7, 2018
1/ A picture is worth a thousand words. And to me, an x-y is worth a million. Here are some things I believe to be true based on my experience as a CEO and investor. Some or all may be completely wrong.
Ryan Caldbeck
@ryan_caldbeck
Mar 14, 2018
1/ Everyone in consumer is trying to figure out how to play emerging CPG (<$15m in revenue). EVERYONE. Every public CPG company, every retailer, every consumer VC and PE firm, every meaningful public investor. EVERYONE. Here is why.
Ryan Caldbeck
@ryan_caldbeck
Apr 16, 2019
1/ We Pivoted a few yrs ago. This is the story- mostly my feelings. It has never been told publicly. This will be rambly and represents the chaos in my head at the time. There is [hopefully] no advice here. I don’t know if we did it right.
Ryan Caldbeck
@ryan_caldbeck
Jul 21, 2018
Dear @elonmusk and @Tesla – I just saw another similarly horrible story yesterday. Is there a simple hack -i.e. weight in baby seat results in air conditioning turned on (if internal temp too high) or alarm on phone (via app)? cnn.com/2018/07/03/hea…
Ryan Caldbeck
@ryan_caldbeck
May 3, 2018
When a CEO/founder says "culture is the most important thing", it's really hard to understand how true that is until you've been a CEO/founder. Learning that culture is the most important thing is probably the most important lesson I've learned as a CEO.
Ryan Caldbeck
@ryan_caldbeck
Aug 20, 2018
1/ How to get promoted at a startup: At larger companies career tracks are (too) well defined, and there are clear paths on how to move up. But at startups there isn’t a playbook for how to get promoted.
Ryan Caldbeck
@ryan_caldbeck
Jul 31, 2018
Am I the only human that is amazed that @Gmail hasn’t figured out how to more effectively notify users that your fonts are jacked up when you send an email that has different font sizes/styles? That feels like a solvable problem in 2018 to help users not look like clowns.
Ryan Caldbeck
@ryan_caldbeck
Mar 25, 2018
Replying to @ryan_caldbeck
11/ I heard so many times “if you are thinking about firing someone the decision has already been made.” That is correct.
Ryan Caldbeck
@ryan_caldbeck
Jul 5, 2018
Most underreported story in sports over the past 15 years.
NBACentral
@TheDunkCentral
Jul 4, 2018
Best role model in sports.
Ryan Caldbeck
@ryan_caldbeck
Mar 6, 2022
1/ Leadership lessons from Coach K. I was a walk-on for the 2001 @DukeMBB national championship team. It isn’t something I talk much about publicly (or privately) because it’s hard to summarize authentically in a tweet or a quick conversation. Today is an exception. #CoachK 🐐
Ryan Caldbeck
@ryan_caldbeck
May 27, 2018
Replying to @ryan_caldbeck
9/ ….a quote from Howard Schultz I really like: “One of the fundamental aspects of leadership, I realized more and more, is the ability to instill confidence in others when you yourself are feeling insecure.”