And other life lessons from Jerry Colonna, Silicon Valley’s leadership coach and “CEO whisperer”

Spero Ventures
Aug 14 · 5 min read
Shripriya Mahesh, Partner at Spero Ventures introducing Jerry Colonna, founder of Reboot.io, to an audience of CEO’s and Investors during a Barefoot Interviews series event.

Last month we hosted Jerry Colonna, founder of leadership development firm Reboot.io and author of the new book, Reboot: Leadership and the Art of Growing Up, for a talk with Spero Founding Partner Shripriya Mahesh. Their conversation was part of an intimate evening with friends, mostly founders and investors, some of whom knew Colonna and told us that working with him caused them to change the direction and purpose of their careers.

Because we know that Colonna’s wisdom and perspective is helpful to so many people, we wanted to share highlights of the conversation here with you.

Colonna spent nearly two decades as an investor and board member for more than 100 companies. Some of his earliest investments included GeoCities, PlanetOut Partners, and Gamesville. Later he was an angel investor in Twitter. Working with Fred Wilson, he co-founded his second venture firm, Flatiron Partners, one of the earliest investors in the emerging NY-based technology scene, and then later joined the private equity arm of JP Morgan, JPMP. He began coaching in 2006 and co-founded Reboot in 2014 with the belief that “better humans make better leaders” and the idea that “work doesn’t have to destroy us.”

If that sounds like an unusual perspective for a former venture capitalist, that’s because Colonna isn’t the typical VC. Raised in Brooklyn, his family struggled financially. He graduated from Queens College with a BA in English Literature. Before going into finance, he worked at CMP Media, a digital media company, and was an editor for Information Week. He’s a committed Buddhist who serves as Chair of the Board of Trustees at Naropa University, a Buddhist-inspired university in Colorado.

After the dot-com crash, closure of his venture firm, and the 9/11 terrorist attacks, Colonna found himself in a dark depression. He put much of his time and effort into recovery through therapy and meditation. Going deep allowed Colonna to see the things in himself that he wanted to change — and it helped him see a new way to help others. Today he coaches leaders in one-on-one sessions, workshops, lectures and bootcamps.

Going deep allowed Colonna to see the things in himself that he wanted to change — and it helped him see a new way to help others.

To kick off the conversation, we asked Colonna to read aloud an excerpt of his book. He started by setting expectations: “It’s kind of about leadership, kind of not. It’s a book about being human.”

And then he proved it by reading a passage about the gut-wrenching experience of one of his clients, Chad Dickerson, who had just been fired as CEO of Etsy. It’s a CEO’s worst nightmare: a public rebuke of your performance. The night before the announcement was scheduled to go out, he sat down with Colonna on the rooftop of Etsy’s headquarters, near the East River. They reminisced about the six years they worked together while Dickerson was running the company, including the panicked moments that lead to stomach-churning vomit.

Dickerson’s story serves as a vehicle to teach about how to break through what Colonna calls “the not-knowing” — an unbearable state of existence for high-achievers. He explains an essential truth about leadership: “There’s no book, no path, no way that’s been kept hidden from you…The truest path, the only way for a warrior to emerge is through the path of radical self inquiry.”

“There’s no book, no path, no way that’s been kept hidden from you…The truest path, the only way for a warrior to emerge is through the path of radical self inquiry.”

In kind, Colonna shared a bit of his own story. Growing up, his mother suffered from mental illness and his father was an alcoholic. It was a constant struggle for Colonna to bounce back, time after time, from incredibly challenging situations. That experience taught him to be hyper vigilant — he learned to look deep into the eyes and behaviors of the adults around him, scanning for minute changes in their emotional weather, forever alert to any dangerous storms that might be building.

Colonna’s painful childhood forced his subconscious to invent a powerful defense mechanism that allowed him to understand people better, quicker, despite their best efforts to conceal their state of mind. He continued to fine-tune that ability throughout his life and used it to create a successful, meaningful career that has helped countless people live happier lives — and, in turn, made them better leaders and parents, which helped the people around them live happier lives.

Understanding this about himself has allowed Colonna to guide others through the same type of self-evaluation. He helps you identify your limitations and see how they are the result of past baggage or issues that are not yet resolved. Like a Freudian revelation, the hope, then, is that you can begin the work of healing and becoming stronger.

When you engage Colonna, there is no place to hide. He sees through the things most people gloss over: a joke about your controlling spouse when your marriage is falling apart; an artful dodge to avoid talking about your struggle with cancer; a side note about how no one ever listens to you. He calls those things “speed bumps” and encourages you to slow down and allow yourself to notice and address them.

If you’re in a small group of people and you ask a question, he pauses, then looks deep into your eyes. He walks over to you, uncomfortably close, and kneels at your feet, his eyes below yours — a deliberate signal to your lizard brain that he is not a threat — and gently but directly asks question after question, peeling away protective layer after layer, until finally he’s found it: your soft underbelly; the spot that still smarts like a fresh wound, even decades after being inflicted; the part of your unconscious that’s been trying to hide; the part of your mind that until now has been allowed to control the way you make decisions, act around other people, handle difficult conversations, and even judge yourself.

Toward the end of the evening, an investor in the room asked Colonna if he could help them understand — and conquer — their crippling inability to make decisions.

He walked, kneeled, asked. Asked again. And again. And again.

There! Their indecision started when they were a kid and their father left them. It’s clear when Colonna says the thing out loud, it resonates. And now the difficult work begins: how to move past it.

Scanning the room, there’s no doubt others have had similar challenges. Everyone who meets Colonna is affected by him.

As much as it may seem like a shameless plug, I’ll say it anyway: Radical self-inquiry leads to greater resilience. Buy Colonna’s book and see for yourself.


Spero Ventures

News, podcasts, and insights from Spero Ventures.

Spero Ventures

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Spero Ventures is an early-stage venture capital firm driven to deliver value to shareholders and society.

Spero Ventures

News, podcasts, and insights from Spero Ventures.

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