How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC)

**Jerry Colonna** (0:00)
We're socialized to bullshit not only ourselves, but everybody else, especially in the entrepreneurial community. All our companies are moving up and to the right. Every product is working. We don't really have any problems because we're crushing it. And that's just a lie. The question that I often ask is, how have I been complicit in creating the conditions I say I don't want? The purpose of this question is actually to evoke your own agency. A perfect example of that would be, I say I don't want to feel busy all the time. But the truth of the matter is, I feel really unnerved and disconcerted if my agenda isn't jam-packed. So if you want to create a high-functioning team, do your work. And it starts with the person who has the most power.

**Lenny Rachitsky** (0:48)
Today, my guest is Jerry Colonna. Jerry is one of the most well-known and respected executive coaches in the world. He's co-founder and CEO of Reboot, an executive and leadership development firm grounded in the belief that better humans make better leaders. Prior to coaching, Jerry co-founded Flatiron Partners with Fred Wilson, which ended up being one of the most successful early-stage investment funds in the world. He's also a partner at JPMorgan Chase and is the author of two books, Reboot and Reunion. As you might expect, this ended up being a very real and very open conversation about being busy and self-inquiry and the dangers of a growth mindset and the reasons that leaders and teams most often fail and it's not what you think. Also, we talk about a very simple equation that Jerry and his team use to cultivate great leaders. This is an episode that everybody should listen to and spend time with. It'll make you a better person, a better partner, and a better leader. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also, if you become an annual subscriber of my newsletter, you now get a year free of Linear, Superhuman, Notion, Perplexity, and Granola. Check it out at lennysnewsletter.com and click Bundle. With that, I bring you Jerry Colonna. This episode is brought to you by Epo. Epo is a next-generation AB testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams. Companies like Twitch, Miro, ClickUp, and DraftKings rely on Epo to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features. And Epo helps you increase experimentation velocity while unlocking rigorous deep analysis in a way that no other commercial tool does. When I was at Airbnb, one of the things that I loved most was our experimentation platform, where I could set up experiments easily, troubleshoot issues, and analyze performance all on my own. Epo does all that and more with advanced statistical methods that can help you shave weeks off experiment time and accessible UI for diving deeper into performance, and out-of-the-box reporting that helps you avoid annoying, prolonged analytic cycles. Epo also makes it easy for you to share experiment insights with your team, sparking new ideas for the A-B testing flywheel. Epo powers experimentation across every use case, including product, growth, machine learning, monetization, and email marketing. Check out Epo at getepo.com/lenny, and 10x your experiment velocity. That's geteppo.com/lenny. This episode is brought to you by ContentSquare, the analytics platform that helps companies build better digital experiences. Ever wonder why customers drop off before converting? Or why some pages perform better than others? ContentSquare takes the guesswork out of digital experiences, giving you real time insights into how users interact with your site or app. With AI-powered analytics, automatic frustration detection, and clear visualizations, you'll know exactly what's working and what's holding your customers back. Whether you're optimizing an e-commerce checkout, refining a B2B lead flow, or improving a mobile app experience, ContentSquare pinpoints exactly what needs fixing and why. ContentSquare powers better customer journeys across 1.3 million websites and apps. Discover the insights you've been missing at contentsquare.com/lenny.
Jerry, thank you so much for being here. Welcome to the podcast.

**Jerry Colonna** (4:19)
Well, thanks for having me, Lenny. It's really a delight to meet you and to be with you today.

**Lenny Rachitsky** (4:24)
I want to start with a very classic Jerry Colonna piece of advice that I've heard you share in other places, and I just want more people to hear this advice. And this is a question that you ask people when things aren't going their way. And I'll give you a hint, the question contains the word complicit.

**Jerry Colonna** (4:40)
Right.

**Lenny Rachitsky** (4:40)
Can you share this question and why it's so important to ask this of yourself?