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Hey there. Let’s put together a great piece together here.
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First draft 🕵🏻‍♂️Jerry Colonna is the Co-Founder and CEO of Reboot, a leadership coaching company known for blending radical honesty with deep self-inquiry. Before becoming one of the most respected executive coaches in the startup world, he built a successful career in venture capital, serving as a partner at J.P. Morgan Partners and co-founding Flatiron Partners, one of the most influential early internet venture funds. His work today focuses on helping founders and leaders confront their fears, find meaning in their work, and lead with empathy and authenticity.
He’s also the author of Reboot: Leadership and the Art of Growing Up and Reunion: Leadership and the Longing to Belong, both of which explore how emotional awareness, vulnerability, and maturity can transform leadership. Combining his experience as an investor, Buddhist practitioner, and coach, Colonna challenges traditional notions of success—encouraging leaders to see personal growth not as separate from business growth, but as its foundation.
The man.
The first thing is to acknowledge everything you’re struggling with—like imposter syndrome. One of the biggest blockers for founders is pretending they have all the answers. Recognize that this is probably the hardest thing you’ve ever done and ever will do, and that’s okay. You’re joining the club. Drop the idea that you’re supposed to have it all figured out from the beginning.
https://www.youtube.com/watch?v=PJE7etZQ9us
I used to do public talks for first-time CEOs. I’d come on stage, let a pause hang, and then ask, “Who here wants to admit they haven’t a clue what they’re doing?” Everyone would laugh. I’m doing two things: naming the demon and normalizing it.
One way we make these feelings worse is by believing we’re the only ones who feel that way. My son, a retired professional Muay Thai fighter, is building a startup that makes high-end boxing gear. He’s been on an emotional roller coaster—dealing with tariffs, manufacturers in Thailand and Portugal. I told him, “Welcome to eating a bag of glass.” He laughed and said, “I thought it was just me.” I told him, “No, everybody’s messed up.”
Normalization, humor, and self-deprecation are key. You’re not the imposter you think you are, and you’re not the greatest thing walking the planet either. You’re just figuring it out every single day.
Absolutely. Let’s take an example: you’re the leader, and you talk too much. That means you’re not listening to people closest to the problem or the customer. You’re probably trying to quiet the voice in your head that says you don’t know what you’re doing—by talking.
Or maybe you quiet that voice by micromanaging, avoiding conflict, or pretending everything’s great—what I call toxic positivity. “Everything’s great.” No, it’s not. The product doesn’t work. Let’s fix it.
What we’re really talking about is the neuroses of the person with the most power distorting the organization. Sometimes it’s grandiosity, sometimes imposter syndrome, sometimes conflict avoidance, or conflict seeking. The point is: get your fucking shit together. If you’re going to be a leader, get your shit together.
