Jerry Colonna is the CEO and Co-founder of Reboot.io, an executive coaching and leadership development firm dedicated to helping leaders grow through the practice of radical self-inquiry. A former venture capitalist, Jerry is a renowned executive coach and the author of two acclaimed books, Reboot: Leadership and the Art of Growing Up and Reunion: Leadership and the Longing to Belong. Known for his candid storytelling and exploration of personal and generational challenges, Jerry draws on his experiences as an immigrant, entrepreneur, and leader to help others uncover unconscious patterns and build authentic connections.
Here’s a Glimpse of What You’ll Hear:
- [2:11] Jerry Colonna opens up about how generational influences shape our fears, beliefs, and business decisions
- [6:51] Why trusting yourself can become the most powerful driver of entrepreneurial success
- [10:43] Jerry shares how radical self-inquiry became a turning point in his leadership journey
- [14:11] How uncovering family secrets reshaped Jerry’s understanding of identity and ambition
- [17:23] The profound impact of reconnecting with ancestral roots in Ireland
- [20:32] Why Jerry believes belonging is essential for becoming a grounded, authentic adult
- [24:25] Exploring the moral responsibilities leaders face in today’s divided and fast-changing world
- [41:14] Jerry’s take on the hidden dangers of AI-driven therapy and our growing digital dependence
In this episode…
What if the beliefs, fears, and resilience that shape our lives today are not just personal traits, but echoes from generations past? Understanding how ancestors faced change, poverty, and struggles with belonging can transform the way we lead and live. Could reconnecting with our family history reveal where — and to whom — we truly belong?
Jerry Colonna, a renowned executive coach and author, tackles these profound questions by tracing his family’s immigrant journey and exploring how generational experiences inform our sense of self. Using stories of his entrepreneurial grandfather and the hardships his own parents faced, Jerry reveals how both inspiration and trauma cascade through generations, influencing our choices, leadership styles, and even our capacity for resilience. He shares his personal quest to bridge the disconnections in his own lineage — including a revelatory trip to Ireland to reclaim lost roots, demonstrating how true self-understanding only comes when we look beyond ourselves to our collective past.
Tune in to this episode of the Smart Business Revolution Podcast as John Corcoran interviews Jerry Colonna, CEO and Co-founder of Reboot.io, about the legacy of generational trauma, belonging, and leadership. Jerry shares candid reflections on family resilience, the illusion of self-reinvention, and how embracing your roots can strengthen both heart and leadership.
Resources mentioned in this episode:
- John Corcoran on LinkedIn
- Rise25
- Jerry Colonna on LinkedIn
- Reboot.io
- Reboot: Leadership and the Art of Growing Up
- Reunion: Leadership and the Longing to Belong
Quotable Moments:
- “I fundamentally believe in me more than I believe in anybody else. And that’s a positive and a negative.”
- “The central question is: how have I been complicit in creating the conditions I say I don’t want?”
- “We struggle to become fully grown adults until we know to whom and to where we belong.”
- “Violence is what we do when we don’t know what to do with suffering.”
- “It is not yours to complete the work, but neither are you at liberty to ignore the work.”
Action Steps:
- Engage in radical self-inquiry: Reflect regularly on your beliefs, behaviors, and emotional responses to understand the unconscious patterns that drive you and promote intentional growth.
- Explore your ancestry and family history: Research and connect with your roots to foster a deeper sense of belonging and resilience.
- Cultivate empathy and compassion: Make a conscious effort to relate to others’ experiences to bridge divisions and strengthen communities.
- Take responsibility for your influence: Assess how your actions affect broader systems and identify meaningful ways to support inclusion and reduce suffering.
- Build real-world connections and community: Seek genuine face-to-face interactions to counter isolation and strengthen communal bonds.
Sponsor: Rise25
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Episode Transcript
Intro: 00:00
All right. Today we’re talking about how generations shape our fears and our belief systems and how we see the world. My guest today is the author of Reboot and Reunion. His name is Jerry Colonna. I’ll tell you more about him in a second, so stay tuned.
John Corcoran: 00:16
Welcome to the Smart Business Revolution Podcast, where we feature top entrepreneurs, business leaders, and thought leaders and ask them how they built key relationships to get where they are today. Now let’s get started with the show.
John Corcoran: 00:33
All right. Welcome, everyone. John Corcoran here I am, the host of this show. And you know, if you’ve listened before that every week we have interesting and smart CEOs, founders and entrepreneurs from all kinds of companies. And if you check out the archives, we’ve got Netflix and Grubhub, Redfin, Gusto, Kinko’s, Activision Blizzard, LendingTree, lots of great episodes.
So check those out. And of course, this episode brought to you by our company, Rise25, where we help businesses to give to and connect to their dream relationships and partnerships. How do we do that? We do that by being the easy button for any company to launch and run a podcast. We do three things: strategy, accountability in full execution.
And we even invented what some are calling the Wix of B2B podcasting, which is our platform podcast Co-Pilot. So go to our website at rise25.com, or you can email our team at support@rise25.com to learn more about it. All right. I’m super excited about today’s guest. His name is Jerry Colonna.
He’s the CEO and co-founder of Reboot.io. So a coaching and leadership development firm is dedicated to the practice of self-inquiry. He’s a former VC and executive coach. He helps entrepreneurs, CEOs and leaders to explore various different emotional and psychological challenges that come with leadership. I’ve seen him speak in person.
He came to our San Francisco chapter about a year and a half ago, really had a huge impact on me and everyone else who was there. Jerry, I’m super excited to have you here today and to dive into this conversation. But, you know, I always start by getting to know people a little bit, what they were like as a kid. And you and I have a few parallels in our backgrounds, but tell me a little bit about your grandfather. You had a grandfather who had a big impact on you.
Ran a home ice delivery business back when that was a thing. And growing up in Brooklyn, what was that like?
Jerry Colonna: 02:12
Well, the first thing I want to say is thank you for having me on the show. And you forgot one part of my bio, which is that I’m devastatingly handsome, so. Okay. Yes, sir. You know.
John Corcoran: 02:20
What? It was there. I just skipped over it.
Jerry Colonna: 02:22
You just skipped over it? Yeah, right. So, grandpa. Grandpa was Dominic. Guido and I spent a lot of time in my first book, reboot, talking about Dominic.
And then pick up some of the story in In Reunion. My second book, Dominic, came from a small town in southern Italy called Palo de Colle in Puglia, which is the hot place to visit now in Italy wasn’t then. It was incredibly poor, and he emigrated to the United States when he was 16. And the somewhat apocryphal story is that he got off the ferry from Ellis Island, landed in Little Italy, passed a pushcart that had ice on it, picked up the pushcart, stole it, and began selling from the back of this pushcart. And eventually he had a little bit of an empire in Brooklyn with something like 3 or 4 trucks and maybe 30, 40 people working for him.
He had no more than a sixth grade education. And the reason I tend to focus on him, aside from the fact that he and his wife, my grandmother Nicoletta, aside from the fact that they were an immense source of stability in a very tumultuous life. My mother had bipolar disorder. My father was an alcoholic. We talked about that.
He was the first person that I ever saw who did the magic trick of starting something out of nothing. And the result was he was able to bring over relatives. He was able to put all seven of his kids through a pretty good education. Wow. He and I always have this image of him.
My mother used to say again, I think she was exaggerating, but I liked the image. She used to say that my grandfather’s shoulders were hairy because he would carry £50 blocks of ice on his shoulders, up and down the stoops of Brooklyn. Wow. And. It’s a really powerful image for me, because he was the first person who taught me about what it really means to be an entrepreneur.
John Corcoran: 04:55
And did it draw you to entrepreneurship because you saw his experience, you saw what he had built from literally nothing.
Jerry Colonna: 05:02
Well, I yes and no. What really propelled me was a kind of negative experience. It was a negative space. We were talking a little bit before the show and we have another thing in common. My father lost his job when I was ten and my father was like a lot of men of his generation.
I’m 62, so he would have been over 100 now if he had lived. He died about 30 years ago. When? He had spent most of his life working for the same company. He went to the high school for the New York High School for the Printing Arts.
Took a break. Went to the Army. Spent, you know, a couple years in the Army as a youngster. Came back and worked for the same printing company. And as is often the case and we may be going through this period right now, technology basically crushed the company.
People started using computers to do letter sets and typesetting, not the big old typesetting machines that were in his company with lead type and all that.
John Corcoran: 06:30
This was the mid 70s, if you were 19. 1973 okay.
Jerry Colonna: 06:36
And he came home just before Christmas and said that there was going to be no Christmas. He had just lost his job after working all those years since high school for the same company.
John Corcoran: 06:50
Yeah.
Jerry Colonna: 06:51
And what if you put these two experiences together? What you had was I have had a hard time working for other people. And it’s not because I don’t I controlling. There’s an aspect of my personality that is controlling. But I found my grandfather Dominic.
I fundamentally believe in myself more than I believe in anybody else. And that’s a positive and a negative. And so I, you know, as I often joke, I am absolutely convinced that if you drop me off on a desert island, I will build a business selling lemonade to myself. I will find a way. Which is what I got from my grandfather.
What I got from my father was. It’s really hard to count on anybody else.
John Corcoran: 07:46
Yeah. Yeah. And I had a similar experience. My father lost his job when I was, I think seven, 11 and 14, so three separate times. And each time we had to move across the country like we were living on each coast and we like to get a new job months later in another city across the country, so massive, you know, change.
Jerry Colonna: 08:05
So how did it impact your job choices?
John Corcoran: 08:08
Well, it led me down a journey of self-discovery where I studied other successful people across different industries. And I didn’t become an entrepreneur until I was about 30, 31 years old. But it was similar to you. Like it led me to trust myself. You know, I ended up getting a law degree.
My parents had never gone to graduate school. You know, I ended up, you know, trusting myself. Really? I was going to ask, actually, you mentioned your grandfather had this ice delivery business, and I was thinking of disruption. You mentioned that it hit your father.
Did your grandfather? Do you ever see your grandfather experience that as refrigeration took hold?
Jerry Colonna: 08:44
Sure, absolutely.
John Corcoran: 08:45
And how did he adapt to that?
Jerry Colonna: 08:48
You know, it’s a good question. I and no one’s alive of that generation for me to ask. I know that when I was born in 63, by 63, the business was gone. But my earliest memories of him working were again working for a family business. In this case, it was my Uncle Leo, and he was my mother said my mother had six siblings, one of whom was my aunt Rose.
She married Leo, and Leo had a very famous Italian restaurant in Brooklyn on 18th Avenue. I think that’s where it was or McDonald Avenue. And my earliest memory of my grandfather is of him working there.
John Corcoran: 09:42
So your grandfather eventually went to work for his son in law.
Jerry Colonna: 09:46
Yeah. And? And another uncle worked for that same guy. Uncle Louie was a chef who worked for Leo, and grandpa worked there. But by the time I’m cognizant of him, my grandfather died shortly after my father lost his job.
So I don’t have clear memories of him going to work. But I do have memories of him being in his 80s and still working. Which, now that I think about it, that’s a pretty profound memory as well.
John Corcoran: 10:20
It is. Right? Yeah. So all of this is kind of a prologue to a discussion around how our generations before us, our ancestors, really influenced who we are today. So talk to me a little bit about how this background, your family background, influenced what you eventually came to write about and to talk to others about?
Jerry Colonna: 10:43
Well. So. In the reboot, there’s a central theme. And the theme. This is my first book.
The central question is how have I been complicit in creating the conditions I say I don’t want? So it’s a core part of the work I do is where I encourage a kind of radical self-inquiry. And in that the subtitle of that book is leadership in the Art of Growing Up. And so I use the act of storytelling stories about my own experience growing up in adverse conditions with my mother’s mental illness, my father’s alcoholism, to really sort of unpack, well, who am I and how am I wired so that, you know, there’s a famous quote from Carl Jung that goes until you make the unconscious conscious, it will direct your life and you will call it fate. And boy, does that land right.
So reboot really sort of unpacks that. What I tried to do in reunion, and because I was sort of looking at a written reunion, I started writing reunion in the summer of 2020. And if you remember back then, yeah, we had protests in the street, we had Covid going on, and there are a couple of different events that really sparked that, one of which was my daughter protesting the murder of George Floyd and out in the streets there. And what I really wanted to understand was, how have I been complicit in and benefited from a world I say I don’t want to see? And what I came to understand is that there is a profound disconnection.
There are several profound disconnections. There’s a disconnection between our sense of self and how we really are wired. And in a sense I approach that in reboot. There’s obviously a disconnect between people. I mean, and we’re living through times like that again right now that lead to children shooting children in high school.