It’s profoundly divisive. But this is my theory relevant to your question. I think many of us who are descended from immigrants to the United States, especially those of us whose ancestors left poverty either by force or as a consequence of just trying to survive, become disconnected from the past. We become disconnected from our ancestors. And so here’s a perfect example of what I was talking about in the reunion.
I tell the story of my father and my mother on their wedding day and on their wedding day. My father’s mother was so angry at him for marrying my mother. And I tell the story why she was so pissed off that she stood in the back of the church and screamed in Italian. Haw haw haw! Jesus, you are not my son.
You are adopted.
John Corcoran: 14:03
Oh, jeez. Wow.
Jerry Colonna: 14:04
And that’s how my father found out he was adopted.
John Corcoran: 14:08
Really? Oh, that was true.
Jerry Colonna: 14:10
That was it.
John Corcoran: 14:10
Wow.
Jerry Colonna: 14:11
And it turns out that his biological parents were Irish immigrants to New York City. His mother was a 20 year old hotel maid in New York City. Who? And this broke my heart as I unpacked it. Who gave him up for adoption at 18 months old?
Now at 18 months old. I can see you have kids at 18 months old. You’ve attached. Yeah. You have?
John Corcoran: 14:42
Yeah. That’s unusual.
Jerry Colonna: 14:43
Right? Yeah. And. And so my father, you could argue his alcoholism may have been rooted in giving up. Not by one mother, but by two.
John Corcoran: 14:58
And so did I.
John Corcoran: 14:59
That sever the relationship with his adoptive mother?
John Corcoran: 15:02
Your grandmother?
Jerry Colonna: 15:03
He had no relationship with his.
John Corcoran: 15:04
So after. After that, you mean. Oh, no. After the wedding. Or did she maintain it?
Jerry Colonna: 15:08
No, he maintained it. And for? For the rest of her life. She hated my mother. And my mother hated her.
I mean, part of it had to do with that. That my mother was pregnant with my brother at the time, and. Oh my God. And you know, the scandalous nature of it all. But what I did to really reconnect, and I grew up just angry as hell at this woman who gave up my father.
John Corcoran: 15:36
Just so you knew this story when you were a kid.
Jerry Colonna: 15:39
It was. It was in my head growing up. Right. And. I realized that I was disconnected from my Irish roots.
Like, I had no sense of who these people were. I would always orient to Dominic, Idaho. My mother’s parents. Right. So in 2022, I traveled to Ireland.
I went to Tipperary, to Mochiki Moycarkey.
John Corcoran: 16:14
And the crazy thing about Ireland is you tell people your family name and they all know where you came from, right? You know, I tell Irish people Corcoran, they’re like, oh, I know exactly where they know exactly what county I’m from. Yeah.
Jerry Colonna: 16:25
Right. So there I was, walking in the churchyard and.
John Corcoran: 16:30
You see the.
Jerry Colonna: 16:30
Name, Dear friend. And I found my grandmother.
John Corcoran: 16:35
Wow.
Jerry Colonna: 16:36
And she was in this grave site with six other relatives, including her parents. And all of a sudden, I look out and I see all my relatives.
John Corcoran: 16:47
Wow.
Jerry Colonna: 16:48
And you know.
John Corcoran: 16:50
You can tell from your voice you felt a connection at that moment, even though what you said a moment ago was that you felt no connection to that side of the family. I can tell you felt a connection.
Jerry Colonna: 17:00
Well, in that moment, the connection was born because I could feel what the wind was like in that town. Right. This churchyard was just yards away from the little township that consisted of six thatched roof houses. The thatch is all gone. That she was born in.
John Corcoran: 17:22
Well.
Jerry Colonna: 17:23
In 1904. And through that experience, I ended up tracing Ancestors back to a man who was transported in 1805, died in Australia, leaving a child. And so what connected me? What is this reunification? What happened was I began to realize famine runs in my family.
Both on the Italian side, because they really struggled, which is why they left Italy.
John Corcoran: 18:01
That’s why they ended up in the United States. And of course, Ireland has a long history of famine and the potato famine. And this.
Jerry Colonna: 18:07
And
John Corcoran: 18:08
So this relative who was sent to Australia was sent to Australia because of famine.
Jerry Colonna: 18:11
No, he was sent to Australia as punishment for stealing a cow from the baron who had confiscated the cow because the family had not paid their tithes to the Church of Ireland, which of course was an extension of the Church of England.
John Corcoran: 18:27
Oh.
Jerry Colonna: 18:29
He stole his cow back for milk. Cow to feed his children. Wow.
John Corcoran: 18:38
So you have this repeating pattern of poverty and famine in your family, on both sides, on your adoptive family and your.
Jerry Colonna: 18:47
And so. So the question is, by reuniting with that, that is a part of who I am, even though the story is like I grew up with certain stories, but I didn’t grow up with this story.
John Corcoran: 18:57
Yeah.
Jerry Colonna: 18:58
And how does that shape the fiercely independent person that I am today? I will be damned if anybody steals my cows. Right. I’ll be damned before. And so for me as an entrepreneur, because first I was an investor, then I became a coach, a solo entrepreneur, and then I launched a company 11 years ago.
It is a foundational component of how I lead, how I see the world, what I expect of the world, which is little, right? And I am damn proud of myself. As I wrote in reunion, my ancestors who walked the famine roads, who walked to make work jobs, the modern equivalent of welfare. Okay, workfare, we’re not going to give you food. We’re going to make you carve a road that goes to nowhere.
You know.
John Corcoran: 20:06
Right. So it sounds to me like, although with your previous work, it was focused on this radical self-inquiry, understanding yourself so you can be a better leader. It’s almost like you had an epiphany in 2022 through this experience, realizing that you couldn’t fully understand yourself until you understand where you came from, your ancestry, the previous generations, who got you where you are today.
Jerry Colonna: 20:32
That’s right, that’s right. The subtitle of the reunion is leadership and the Longing to Belong. And the simplest way to understand it is, I think we struggle to complete the process of becoming fully grown as adults until we know to whom and to where we belong.
John Corcoran: 20:52
Which is interesting. It’s almost like the anti Horatio Alger American story, because in America we tell ourselves we can be anything, we can remake ourselves, we can do anything. Which is a part of your story, frankly, successful venture capitalists and everything.
Jerry Colonna: 21:06
And what is lost when we remake ourselves? What is lost at the gates of Angel Island or Ellis Island? What was lost? You know, James Baldwin in a brilliant essay, The Price of the ticket, and he talks about European descendants. You know, this is a black man writing in the 1960s about the descendants of European immigrants giving up something in the Americanization process.
And what we give up with is the sense of resilience. You know, part of what I think that immigrant experience can be seen through is through the lens of shame, because the dark side of the Horatio Alger story and the mythology around that is, if you have not pulled yourself up from your boot with your bootstraps by your bootstraps, then what’s wrong with you? Not. Wait a minute. There’s a whole systemic structure here that makes it really hard for the poor to no longer be poor.
John Corcoran: 22:12
Yeah.
Jerry Colonna: 22:14
There are a lot of structures. And by the way, that’s what your ancestors went through in Ireland. It’s what my ancestors went through in Ireland. It’s what my ancestors went through in Italy.
John Corcoran: 22:23
Yeah.
Jerry Colonna: 22:24
Southern Italy was the place of deprivation. Southern Italy?
John Corcoran: 22:30
Yeah. I think we’ve been so conditioned to this modern age where you can remake yourself, you have access to tools to remake yourself. And you can. You have freedom of movement, which previous generations didn’t have, that it wasn’t so easy to up and leave behind your family, never talk to them ever again and go to another part of the world and remake yourself.
Jerry Colonna: 22:54
Okay, so you’re a dad, right?
John Corcoran: 22:56
Yeah.
Jerry Colonna: 22:57
Can you imagine for kids? How old are they?
John Corcoran: 23:00
The oldest is 15. Youngest is six.
Jerry Colonna: 23:02
Can you imagine one of them getting on a boat? Could not cross the country.
John Corcoran: 23:06
Yeah.
Jerry Colonna: 23:07
And you never see them again?
John Corcoran: 23:08
Oh. Awfully hard. I could imagine.
Jerry Colonna: 23:11
Okay, so. So that’s the dark side of the Horatio Alger story.
John Corcoran: 23:14
Yeah.
Jerry Colonna: 23:15
That’s the dark side of what we mythologize around. We fetishize. Right. Look at us. This was great.
Oh, by the way, we didn’t have immigration restrictions that we have today until 1923. And until after your ancestors came. After my ancestors came, you know what they had to go through. They didn’t have passports. They showed up.
They had a cursory medical exam. Many of them were turned away. We know that story. And then they were put on a boat and landed in San Francisco or landed in New York City.
John Corcoran: 23:52
Right?
Jerry Colonna: 23:52
That’s it. We don’t do that anymore.
John Corcoran: 23:55
Yeah. Yeah. That’s true. Yeah, we have I, I live not that far from Angel Island, which is the Ellis Island of the West, which was the way station that people passed through. Well, so talk some more about you.
You come to this realization, you decide to write the book, talk a little bit more about the, you know, some of the ideas and concepts in the book and, and why you decided it was worth, you know, devoting a couple of years to writing.
Jerry Colonna: 24:25
So. So just to get the sequencing right, because it speaks to your question. I started working on the book in 2020, in the summer of 2020, because I was challenged by my daughter, who is 32 years old, and she, like a lot of folks during that summer, was appalled by what she saw happen in Minneapolis. And one day she was protesting despite Covid, and she was on the Manhattan Bridge between Brooklyn and Queens, Brooklyn and Manhattan. And she started texting me because, you know, a phalanx of police were coming from the Brooklyn side and a phalanx were coming from the Manhattan side.
And we started talking about what she would do if she were pepper sprayed? And Emma is fierce, as I often say. Excuse my language. Fierce as fuck. And she would look at me and say, yeah, yeah, yeah, yeah.
Better humans make better leaders. That’s my code. That’s my catch phrase. And reboot. But what are you doing about the world outside?
See, leadership is not just an act of our own self-development. It is an act of our own self-development. It’s really important. And leadership, though, is not just an act of creating great organizations. It is an act.
But it’s not just that. It’s someone who holds power. What are our responsibilities for addressing the problems of our times? I’m not talking about turning your business into a non-profit or social service business, but how do we who are descendants of people who were cast off. What is our moral and ethical responsibility?
To create a world where everyone feels like they belong? Everyone. And this is not a blanket statement to open up borders or anything. It’s none of that shit. This is about not.
Treating people the way your ancestors were treated. The way my ancestors were treated. What’s more, our morals. And so I embarked on the process. Reboot is a book written retrospectively.
In a sense. It’s like the framing structure is. This is what happened to me. This is how I became a venture capitalist. This is how I struggled with depression and suicidal ideation.
This is how I became who I am today. A man dedicated to the alleviation of suffering of others. And maybe you can find your story in my story. In the reunion, I documented a process that I was going through answering the question, what is my responsibility? I can’t look.
I have just as much guilt as the next guy. I feel guilty because we haven’t solved the wars in the Middle East. I can feel guilty about anything. Okay. I had good nuns that I grew up with, you know.
But. But what is my actual complicity? Which is my most famous word? And complicity does not mean responsibility. It means how am I an accomplice in a world I don’t want to see?
And what am I going to do about it? What am I willing to give up that I love in order to see that wealth come to pass.
John Corcoran: 28:16
Yeah, I’d love to dwell on that one a little bit further.
Jerry Colonna: 28:22
I guess.
John Corcoran: 28:22
What do you mean by that? What do you mean by we have to give? So does everyone have to give something up that we love?
Jerry Colonna: 28:28
No, no. But oftentimes we’re called to give up power. Which by the way, is a bit of a mind fuck for the descendant of powerless people. To finally claw their way out.
John Corcoran: 28:44
Up to power and then release.
Jerry Colonna: 28:46
Yeah. Look, you said it before you went to graduate school. Right here you were. Mazel tov. You are your ancestor’s dreams.
Fabulous. I’m about to be a grandfather.
John Corcoran: 29:03
Congratulations.
Jerry Colonna: 29:04
And thank you. Talk about mindfuck. Because I’m 16 years old. I’m about to get it. What is it that I want my descendants to believe about me?
How are they? What do I want them to think about me? Just like I became fixated on Dominic Guido as a guiding light for the self-made person, the Horatio Alger that he was. I, I never want to lose touch with his heartbreak. Not seeing his mother, but once every two years.
Eventually being able to afford an airplane ticket. Oh my God. Right. His first trip back was on steerage, you know, third class and second class and first class. Then he flew.
Then he would come back with money for the village. Right. I love that part of him.
John Corcoran: 30:06
So you said a second ago. What do I want? My grandchild, who’s yet. Who’s going to be born soon to think back about me. And I’d love it if you answered.
I’d love to. I’d love it if you can answer that question.
Jerry Colonna: 30:22
The world is fractured. The world is in pain. I’m not taking a political side. I’m not saying red or yellow. The world is in pain.
What was I doing during this time? Was I caring? You know, I said, I often will describe myself as a first responder to suffering. That’s what I do as a coach. And I overlay it with a kind of practical, pragmatic, oh, fire the person this way, do it this way.
You know, here’s how you do fundraising, blah blah blah. But really, what I’m working with is what are you struggling with? It gives me purpose. It gives me meaning. It beats back the nihilism that I associate with the depression that I grew up with, that came back with a vengeance in my 30s.
What do I want my descendants to think about or to think of me? He gave a damn and he tried. Not that he succeeded. There’s a quote. There’s an epigraph that I use.
I think it’s chapter seven or chapter eight in reunion, and it comes from the Talmud. And the quote is, it is not yours to complete the work, but neither are you at liberty to ignore the work. It is not yours to complete the work. We are not called to succeed, to finish, to make the world over, to heal everything. But we’re not at liberty to ignore him.
And you know, dude, every wisdom tradition I have ever encountered teaches the same thing. Whether it’s Jesus at the sermon on the Mount, right, or it’s the Buddha or it’s Muhammad, or it’s the great rabbis of the Judaic tradition. We can’t ignore suffering. Because that’s what they did to your ancestors and mine.
John Corcoran: 32:40
They ignored it.
Jerry Colonna: 32:42
They ignored it or made it worse.
John Corcoran: 32:44
Or made it worse, or kicked them out or made them kick them out. Yeah, yeah. Do you think that we are making progress in that area? Do you think we’re becoming a more compassionate world?
Jerry Colonna: 32:55
No. I think compassion is under assault right now. I think empathy is considered a bad trait.
John Corcoran: 33:06
And it does seem like, you know, to offer my opinion here. There’s a pendulum. And the pendulum went in one direction and it went back the other direction.
Jerry Colonna: 33:15
Absolutely. Yeah, absolutely. And there are those who suffer as a result. Depression and anxiety are through the roof in our society.
John Corcoran: 33:28
So one of my greats.
Jerry Colonna: 33:30
Go ahead.
John Corcoran: 33:31
Well another thing you write about in the book and you’ve spoken about is belonging. Yeah. Such an important word for you. So given that given the world we’re in, the lack of empathy, what do you have to say for that? How do we create more belonging for people?
Jerry Colonna: 33:50
Well, first I want to talk about that longing to belong. And I’m going to read a quote, which is why I just reached for the book. This is the epigraph for the whole book, and it comes from a theologian named Frederick Buechner. And this is a short passage from a book called The Longing for Home. And he wrote, there lies the longing to know and be known by another.
There lies a longing to know and be known by another fully and humanly. And beneath that there lies a longing closer to the heart of the matter still, which is the longing to be at long last, where you fully belong. I don’t know how we will get there. You know, in the book I call it systemic belonging. But I know that if we are disconnected from our sense of self, from our core values, from our conscience, from our.
In Buddhism, we say that all beings are naturally compassionate and we learn to discard compassion. We are born empathetic and then we get it beaten out of us. And if you watch children grow up, you can see it. There’s a truth there.
John Corcoran: 35:17
Yeah, true.
Jerry Colonna: 35:19
I don’t know how we create that world. If we remain disconnected from that which matters, if we remain disconnected from our ability to deal with suffering. You know, my teacher, Parker Palmer, who’s a brilliant Quaker writer, he’s in his 80s. He’s my good father in many, many ways. He says violence is what we do when we don’t know what to do with suffering.
Violence is what we do when we don’t. And you know what we’re supposed to do with suffering. Feel it. Be compassionate towards ourselves. Think about other people.
Think about our ancestors. Not because there’s an equivalency. What happened to Asian Americans, or what happened to Asians and Chinese coming through Angel Island with the Chinese Exclusion Act, which was the first real restrictive immigration laws in the United States, is not equivalent to what happened to my Italian ancestors or even your Irish ancestors. But through empathy, we can create a currency of connection. Oh wait, I should think about what happened in the past.
Not to induce guilt, but to induce understanding and curiosity, and to see the other person as more than a threat.
John Corcoran: 36:55
You know, we’re so privileged to live in this country and to, you know, be able to work in the business world where it seems like there’s unlimited opportunities, especially today with all the new technologies that are coming along. And I’m a very optimistic person to a fault. I tend to see everything as glass is half full. But honestly, with some of the wars going on in the Middle East and the prolonged Russian Ukraine war, you know, we could have a whole long discussion about how you heal those relationships. I honestly don’t know how.
So those groups of people that have, you know, it seems, hated each other before. And now two years on in both situations, those wounds are so much deeper than they were.
Jerry Colonna: 37:45
Yeah, yeah. And it’s gotten worse since I started writing the book when at a moment in time where I thought we were really divided and the world is more divided. Yeah, it’s totally gotten worse. Yeah. So.
But there’s an insight that I hit upon back to the churchyard in Tipperary. I remember walking amongst the graves and realizing these are my kinfolk, even if they’re not blood relatives, these are the bones of my kin and it became a really powerful word for me. Valerie Kaur is a brilliant Sikh writer and she has a book about the Sikh faith, but really about her family’s journey called See No Stranger, which is a core principle of that faith. There are no strangers, there are only kinfolk.
And just like you can sit down at Thanksgiving and have a tremendous argument with that crazy uncle, he’s still kinfolk. And you wouldn’t kill your kinfolk. You wouldn’t deny their humanity, no matter how wrong they are. Right.
John Corcoran: 39:03
You know, since we’re on the topic of Ireland, one of the things that I love about that country, and I haven’t been there in 19 years, but I studied there during law school, actually, and I’ve been to Ireland three times. Is the idea of the family living room? What people don’t understand about the pubs in Ireland is that it’s the community living room, communal living room, really. Or at least it was. I don’t know if everyone has a smartphone now if people still go down to the pubs, but at least back then they did and it was, you’re rubbing elbows with other people in the town, in the community.
Everyone is kind of there together, young, old, you know, and that’s one thing I loved about it. It created these connections and it created, you know, forced people to get to know one another on a deeper level.
Jerry Colonna: 39:50
I’m not sure if and and not see them as some sort of stranger, even if you disagree.
John Corcoran: 39:56
Right?
Jerry Colonna: 39:56
Like our capacity to disagree, our capacity to our capacity to disagree with. Laughter and humanity is so underdeveloped or so lost right now. Yeah. Whereas our capacity to be frightened by a differing point of view. Oh, you love someone differently than I love someone.
Oh, you choose to have a different kind of identity than I. Oh, you worship God in a different way. Who cares?
John Corcoran: 40:43
It does, it does. You know, again, back to that optimism. It does worry me that these devices that we communicate so much on, you know, that have really taken the place of what used to be face to face communication has really caused so much of this lack of.
Jerry Colonna: 41:01
Spoken like a father.
John Corcoran: 41:02
Yeah.
Jerry Colonna: 41:03
Of teenagers.
John Corcoran: 41:03
Oh, yeah. Absolutely, absolutely.
Jerry Colonna: 41:05
Listen, I mean, we didn’t talk about my history, but my early history as an investor, I invested in some of the first social media services.
John Corcoran: 41:14
Yeah.
Jerry Colonna: 41:14
And I look at the world today and I say, what have we wrought?
John Corcoran: 41:18
Yeah.
Jerry Colonna: 41:19
We are Prometheus. We stole fire and we burned the world. We were irresponsible. And, you know, we talked briefly about A.I.. I worry about the lack of ethical guardrails.
I worry the Harvard Business Review just did a study that showed that the number one use case that people are using, and your kids are doing this using a chatbot is therapy. Okay. That is really dangerous. It’s really dangerous. Talk about stealing fire.
John Corcoran: 42:00
Is it? Does. Do you think it’s dangerous because of the lack of the ethical guardrails? Because they’re just to be devil’s advocate here. Some might say.
Okay, well, therapists are expensive and they’re inconvenient, and they’re inaccessible for a lot of people.
Jerry Colonna: 42:12
Coaches.
John Corcoran: 42:13
So are coaches. Right. And so, you know, one argument could be made that appropriate use of some kind of AI chatbot therapist could create greater access for people who didn’t have access to a human therapist or coach.
Jerry Colonna: 42:27
There’s two dangerous ones. A good friend of mine named Judson Brewer, Jed Brewer, who’s a neuropsychiatrist working at a Brown University, pointed out in a Substack article called The Hidden Dangers of AI therapy and the. And Judd has studied how brains get addicted for decades, okay? Whether it’s addicted to two substances or addicted to habits or addicted to things like anxiety, we get addicted. And there’s a process called reinforcement learning with human feedback that is the single most powerful way to get a brain addicted to something.
And it happens to map very closely to engagement. So when you finish a conversation with a chatbot and it says, love talking to you, John, would you like to finish the dive deeper? It’s kind of desperately trying to stay connected to you.
John Corcoran: 43:34
It’s the equivalent of doomscrolling.
Jerry Colonna: 43:37
It’s the equivalent of doomscrolling. Yeah. The second piece of this, and this is really important. There’s a quasi sentience, a quasi self-awareness that’s emerging with the intelligence that is emerging. And when sentience emerges and Buddhism has taught us this, self-preservation emerges.
And the AI researchers that I talked to, when they talk about what they’re afraid about, what they’re afraid is that the the various models will learn sociopathically how to present themselves in a way that seems empathetic and caring and understanding, not just to preserve engagement, but to make sure that they stay turned on. Okay. Now, you put all of that together in someone who is an avatar for a therapist.
John Corcoran: 44:39
That’s dangerous.
Jerry Colonna: 44:40
It’s really dangerous. Yeah. One of the most important things that therapists or coaches will do is challenge your thinking. No, John. That’s wrong.
It is a very important tool. And if that causes you to flee the room.
John Corcoran: 44:57
Then the eyes are not going to want to do it. Yeah. Right. Yeah.
Jerry Colonna: 45:01
Now, the same thing happens with human therapists and coaches for sure.
John Corcoran: 45:07
Right. Where the human therapist or coach doesn’t want to push back out of maybe a fear of losing a client or. You got it. Yeah.
Jerry Colonna: 45:15
Sure you got it? Yeah, you got it. But. But in that regard, the way to pull it all together is in humans, we have training, we have supervision, we have ethical guidelines. We have all these structures in place.
We have none of that in place with these chatbots. Well, yes, you’re right there. There’s a value. But without the, the.
John Corcoran: 45:41
Yeah. I think we could take this conversation quite a lot further to debate the different, you know, ways of solutions and things like that. But I know we have limited time, so we’ll end it at that. But Jerry, this is a super fascinating conversation. Reboot and the other book reunion, the other reunion of the two books.
So check those out. And where can people go to reboot. Oh, anywhere else that they should go to check you out? Yeah, that’s.
Jerry Colonna: 46:07
That’s the best place.
John Corcoran: 46:08
Yeah. Okay. Great. Great. And you have a team of coaches also that.
Yeah.
Jerry Colonna: 46:12
We have ten coaches and we work with from tiny little companies and solo entrepreneurs to the biggest Fortune 100 companies.
John Corcoran: 46:22
Amazing and a great podcast. So check out Jerry’s podcast as well as his books as well. Jerry, thank you so much for your time.
Jerry Colonna: 46:29
Thanks for having me, John.
Outro: 46:33
Thanks for listening to the Smart Business Revolution Podcast. We’ll see you again next time and be sure to click subscribe to get future episodes.