Jerry Colonna: From Venture Capitalist to Conscious Leader

Guy Kawasaki:
I'm Guy Kawasaki, and this is Remarkable People. We are on a mission to make you remarkable. And this episode features Jerry Colonna. Now, Jerry Colonna and I first met when he was a venture capitalist, and I think I was one too. So I fully expected this episode to be all about venture capital and how you pick out entrepreneurial teams and what you want in a pitch and all that VC crap.
But let's just say that he is now an executive coach. He's an author and he's founder of Reboot, a leadership development company. So maybe he was a venture capitalist in his checkered past, but Jerry has transitioned to executive coaching and has a much higher calling.
Now, back then he was recognized on Forbes list of the best VCs. He was on Worth’s list of the top twenty-five most generous young Americans. And he was on Upside magazine's list of the 100 most influential people of the new economy. He's the author of two books, Reboot: Leadership and the Art of Growing Up, and Reunion: Leadership and Longing to Belong.
In this episode, we don't touch on venture capital very much. We talk about leadership, we talk about ethics, we talk about morals, and we talk about what really matters in life. I'm Guy Kawasaki. This is Remarkable People. And here comes Jerry Colonna, former venture capitalist, and now I would say he's a philanthropist and thought leader and just all around good guy.
First of all, Jerry, when I initially got the proposal for you, and of course we said yes, I thought, "Oh, finally I can get a VC with real VC experience and goes back a long way. Flatiron really knows how to pick winners."
I'm thinking, "Oh, we're going to have this whole podcast about venture capital and what do you want in a pitch and how you decide on entrepreneurs to invest in and what's the key to making a successful startup?" And then I get your book and I say, "Holy shit this has nothing to do with venture capital." In fact, I would say it's the antithesis of venture capital, right?
Jerry Colonna:
I don't know if I had a trade in my capitalist card or not to do that book. It's been a journey since I was an active investor. But yeah, I think part of what I'm doing in this new book is just asking people to consider the possibility that people matter more than profits.
Guy Kawasaki:
For no one else than me, how did you make this transition from New York finance venture capital and now we're talking about belonging and othering and others, and it's completely different. It would be like if I interviewed Jane Goodall and all of a sudden she's talking about hedge funds.
Jerry Colonna:
I think that the best way to think about this, and I was thinking about this conversation, Guy, and you won't remember this, but there was a talk you did at a learning annex maybe about twenty-seven, twenty-eight years ago. And I followed you after that talk back when I was still an active investor. And I will say that one of the great misfortunes of my life is to try to go on stage following Guy Kawasaki. I just needed to say that because you were fantastic then and you are remarkable now.
Guy Kawasaki:
Oh, Jerry, I have to say that if one of the great misfortunes in your life is having to follow me on a stage, I would say you had a pretty goddamn life, Jerry.
Jerry Colonna:
Amen.
Guy Kawasaki:
So you're not deaf, you don't have pancreatic cancer, but you had to follow me. Oh my God, you poor thing.
Jerry Colonna:
I'll go back to your question. So our hero was in his late thirties as a successful venture capitalist, and I co-founded Flatiron Partners with Fred Wilson and spent most of my thirties backing companies in what we would call the first internet wave. So we're talking 1996, 1997, 1998, all the way into 2001, 2002.
And that career got interrupted by a massive depression, and the depression was intensely serious. It followed the September Eleventh attacks in 2001. That was certainly a catalytic event for me, but it was really part of a longer arc of a very challenging experience that stemmed from my own childhood. And I detail a lot of this in actually my first book Reboot: Leadership and the Art of Growing Up.
By early 2002, I had transitioned out of Flatiron Partners. Fred had left and begun the work to start what became Union Square Ventures and I joined J. P. Morgan, which was our main investor in Flatiron Partners, thinking that what I didn't want to do was fundraise, but really what I came to understand was I didn't want to live in the body that I was in.
And as intense as the feelings were, they only grew in intensity to the point where I was suicidal. And I've been very open about this. The danger of suicide at that age thirty-eight years old was intense because I had attempted it when I was eighteen. I had failed in my first attempt, thank goodness. But many folks who experienced those kinds of feelings two times over oftentimes succeed. And so it was a very intense period.
After these feelings came up, and there's a really important moment where I was heading up the New York City Olympic bid effort. We were trying to bring the 2012 games to the city. And I left an Olympic committee meeting, which was down in Downtown New York, right near the World Trade Center, what was ground zero.
And rather than leaping in front of a subway train, which is what the feeling was, I wisely called my therapist who said, "Come to my office, we have to talk." And so that's what I did. The reason I often speak to that moment as the moment of transition was I always feel like I had two choices, to live, or to die. What was not acceptable was continuing to live the life that I was living. You can probably relate to this given the number of people that you've spoken to in your own journey in your own life.
Despite the enormous success that I had in my thirties, in fact, because of the enormous success that I had in my thirties, I felt more and more distant from my true self. I often describe it as the inner me and the outer me were in conflict. And the crazy thing, Guy, is that the more I tap danced my way and performed well, the worse I felt inside. The more success I had, the worse I felt inside.
And you asked a simple question, but complicated for me, how did I go from being a successful VC to writing a book about systemic othering and our universal longing to belong, it was through a broken heart and pausing and tending to that. And that began what has now been a twenty-five year career being something other than the VC who was standing on stage at the learning attics following Guy Kawasaki. So that's my long-winded answer to your complicated question.
Guy Kawasaki:
And what did you do to make this transition?
Jerry Colonna:
A lot. I rebuilt myself. D. H. Lawrence has this brilliant poem. There's a line of which that it goes something like this. Are you willing to be erased to be sponged out? Because only then will you be able to change. And so I entered this period three or four years where I started studying Buddhism.
I went to psychoanalysis three times a week. I did art therapy, I did dance therapy. I tried to write a novel about a man in midlife having a crisis. And I traveled the world. I went across the polar ice cap in Greenland, I rafted the Grand Canyon, I went down to Chile and rafted rivers in Chile. I started traveling to Tibet. I built a school in Tibet.
But ultimately, Guy, what really started to change was I started to sit still and meditate and do what I call a practice of radical self-inquiry. Who am I really? What is this person inside? Forget the performing monkey that I had trained myself to be. Who am I really? And how can I live as close as possible to that? And that work led me eventually to becoming a coach, an executive coach, and then writer and doing the work that I do today.
Guy Kawasaki:
So if people are listening to this and they know someone who is going through a similar situation, what is your advice to them?
Jerry Colonna:
I'll share what I came to understand through the work of one of my dearest friends and a mentor of mine, a brilliant Quaker writer named Parker Palmer. Now, Parker is in his mid-eighties, and we often joke, he likes to refer to himself as my little brother.
Newsflash, I'm only sixty, okay? Parker, you've got the math wrong. But he wrote a book called Let Your Life Speak, and it's a Quaker aphorism, which has a double meaning, the first of which is to let the inside of you speak through your actions, and the second is to let your life speak to you.
In that book, which I read when I was in the midst of this depression, in that book, he describes his own journey with depression. And he describes a particular period of depression where every afternoon a neighbor of his, Bill, would stop by his house and sit next to him and not do the thing that the depressed person almost can't stand. Bill would not cheer him up. I know this is counterintuitive.
Bill would not sit there and say, "Come on, buck up. Look at the sunshine. It's beautiful outside." What Bill would do is sit next to Parker and say, "It looks like you're having a hard day today," or, "You look stronger today." And sometimes Bill would take Parker's shoes off and rub his feet because as Parker described, it was the only spot on his body he could bear to be touched.
I was so moved by that scene of a friend, not trying to fix, not trying to make it better, but with deep compassion being able to bear witness to the difficult feelings and do the smallest of human gestures, just rub some feet, let the depressed person know they're not alone.
And so I'll speak to anybody who's feeling that right now. You're not alone. You'll be surprised at the number of people you admire who also struggle. And take comfort in the fact that no matter what your depression tells you, it's a lie. You are lovable, you are worthy, and it will pass. And let somebody rub your feet.
Guy Kawasaki:
Wow. Shit, Jerry, we could end the recording right here and be done.
Jerry Colonna:
Thank you.
Guy Kawasaki:
Wow.
Jerry Colonna:
Thank you for hearing me, honestly.
Guy Kawasaki:
So let me move to your book. So first of all, could you just define belonging to give us a foundation?
Jerry Colonna:
Yeah. Again, a little bit more context. In my first book Reboot, I describe the process by which we could use our work, our experience of becoming the leaders we were born to be, complete our process, and be an adult.
And I talk about in our childhood the fact that one way to think about what experiences we have is to see ourselves constantly in pursuit of three things, to love and be loved, to feel safe, physically, emotionally, experientially, spiritually, and to know without a shadow of a doubt that we belong.
Now, I wrote about that, and I was blown away by the number of people who said, "That story is my story. That is my childhood. That is how I believe. I believe that in order to feel safe, I must work myself to the bone." I was guilty of that. Or, "I believe that in order for me to feel worthy of love, I have to please everybody around me and deny my own feelings." I was also guilty of that.
But this notion of belonging stayed with me after I wrote the book. And what I wanted to do was to really explore this sense. In Buddhism we often talk about this notion of interdependence and the way we are all interconnected to one another.
For me, the pandemic was a perfect experience of this. We needed each other in ways that we were not always cognizant of it. We needed each other to take care of each other. We needed each other in some cases to wear masks. We needed each other possibly to take a vaccine. We needed each other.
And when I look at the struggles that we have, and I did not imagine that the world would be as divided as it is today, even back in 2020, what struck me was the degree to which we can feel groundless in our sense of belonging.
Here's the thing, Guy, you and I just started talking today and we haven't connected in twenty year, twenty-five years, and our lives intertwined and overlapped, and you were over here, and I was over here. But the truth is, we're connected. We belong to one another. Even if your political views are different, even if your religious views are different.
And in exploring this question, what it motivated me was to ask a deep and profound question, what is the responsibility of someone who is like me, privileged, lucky as shit, powerful no matter how I feel, I have power? What is my responsibility in a world? And I'm going to get a little dramatic here.
In a world where babies are murdered for ideology, or grandmothers are shot down in a supermarket, or worshipers in a temple are killed? What is my responsibility? Not from a guilt perspective, but what can I do to make a difference?
To me, this is the most logical extension of the pursuit of love, safety, and belonging. See, if I can make you feel that you belong through the power of interconnection, you will make me feel that I belong.
Guy Kawasaki:
But Jerry, what about people who seem to be hell-bent on making people feel they don't belong? In sense, I think what they believe is I'm going to make some people feel like they belong and some people feel like they don't belong, so that the people who feel like they belong, feel they belong stronger. So it's by defining who's on the outs that helps us strengthen who's on the in as if it's a zero-sum game. So what do you do with that kind of feeling?
Jerry Colonna:
That you just named it. The problem with applying a zero-sum game mentality to human beings is that babies die. By logical extension, some will needlessly die. As you know from reading the book, what sparked me doing this exploration was a challenge by my daughter who's now thirty-one who joined millions and millions of people. And I want to just acknowledge that my children's mom is Chinese American.
My children identify as biracial. I am white, Italian and Irish ancestry. And my daughter, I will tell you, man, she is fierce as fuck. She doesn't take shit. And she works in education. She has spent her last ten years helping build charter schools in low-income neighborhoods, specifically in Nashville, motivated by making a difference in the world. You should have her on your podcast. Forget her father. She's remarkable.
I was motivated and challenged by her with a simple phrase that she used to say to me all the time. When I would think I was doing enough, she would say, "Dad, it's not enough to be an ally. You have to be a co-conspirator."
And when she took to the streets to protest the murder of George Floyd in the middle of a damn pandemic, and I was sitting on this farm that I live on in Colorado, safe and comfortable, and worrying about the world from the safety behind my television screen, my computer screen. I organized myself around this question of how can we be better humans so that we can then be better leaders? And her challenge to me was, "What are you doing, Dad, in a world where this sort of thing happens every day?"
I'm totally lost in my own thoughts, but what motivated me as I write in the book was to be the ancestor worthy of my descendants to look back and say, it's not enough, Guy, that I helped create a bunch of companies, 150, 200 companies, but what am I doing? What is the legacy that I'm going to leave when I turn to dust? And writing a book like Reunion where I take people through this whole question of what is our responsibility? I'll leave it at that.
Guy Kawasaki:
Okay. So now when Emma says to you this challenge about being a co-conspirator, what does it mean in actual terms to be a co-conspirator?
Jerry Colonna:
That's a great question. For me, it means to use what skills and power and privilege I have to tilt at the windmill, to do the work. I don't know why God gave me a gift. I can put words together in such a way that people listen to me. I can do that in writing and I can do that in speaking. Now, I can do that, to quote an old friend of yours, to sell sugar water, or I can do that to look at the questions that really plague us.
And from where I sit, there are two big challenges facing the species. One is climate change and one is the way in which we systemically other people. One is the way we make the other person, the person who is not like us, unacceptable. And we see that throughout this through line of whether it's denial of healthcare rights to individuals because of how they identify or the denial of civil rights, or literally the denial of lifesaving care because of who they are or who they love or how they worship. This is a plague.
So being a co-conspirator means two things. Looking at the ways in which I have been complicit in and benefited from the world as it is, even if I don't like the world as it is, and considering what is it that I'm willing to give up that matters to me, that I love, to see that difference.
Guy, after my first book came out, I was this beloved pseudo-zen Buddhist. "Oh, Jerry. Oh." Right. And here I am putting out a book that challenges people to really question their assumptions. They may not like me after. My friends in the venture business disagree with me. Some of them do. But that's what it means to be a co-conspirator.
Guy Kawasaki:
Okay. Let's get one more definition. Just please define othering. I think that's a great word, othering. Tell us what othering means.
Jerry Colonna:
Yeah, so to give credit where credit is due, the scholar John A. Powell, who is the founder of the Center for Othering & Belonging at UC Berkeley is the first person I heard use that term. And Powell is a brilliant Black legal mind, but really one of the giants in trying to understand beyond the term systemic racism, which doesn't encompass all of the ways in which we create tribes of who belongs and who doesn't.
And it might be the Japanese during World War II, or it might be the Chinese in America during the pandemic or during the Chinese Exclusion Act. It goes beyond our normal conceits of prejudice. It encompasses all of that. And what's beautiful about the term is that it does lead exactly into this notion of belonging, where imagine a world where any child knew, every child knew down to their core that they belonged. I know it's not possible in my lifetime, but I'll be damned if I don't try.
Guy Kawasaki:
But what if this child feels like he or she belongs to a gang or belongs to something that you would not consider positive, belonging is neutral, or is it positive? Because it sure can be negative.
Jerry Colonna:
Is community neutral?
Guy Kawasaki:
I wish it were, but yeah.
Jerry Colonna:
I think you raise a really important point. I can create a sense of belonging in an environment where what brings us together might be violence. And I think what you're backing into is there is a universal longing to belong, and that can be exploited for evil or that can be used for good.
In fact, when we look at say wars that might be going on even as we speak, every side says, "I belong to this." And that wish for belonging, and we know this to be true, is exploited by those who have power to maintain or enhance their power. So yes, the longing to belong can be weaponized, just like the longing for love and safety can be weaponized. That is true.
And so I think we're called to look at this larger question in the light just the way you're looking the question right now, is the answer to deny belonging to that child who seeks a sense of connection and community by joining a gang? Of course not. The problem isn't the wish. The problem with the conditions that seem to send a message that the only place that child belongs is with a group like that.
Guy Kawasaki:
So if there are people who see that the only group that they belong to are Nazis or white nationalists or Christian nationalists or MAGA or whatever, what do you do with that? They're being exploited, let's just say. I think they're being exploited, that people are more similar than they're different and we could all get along, but some people just want to whip them into a fervor. What do you do with that?
Jerry Colonna:
Yeah, that's the conundrum because the connection that you're speaking about, the way in which certain individuals in certain groups will come together in a shared belief about the negative experience of the other person, the negative qualities of the other person, whether it's white nationalists or white supremacists, or those who would deny healthcare rights to women, for example, and find common cause with a group of people.
What you're asking is how should those of us who seek to find, to build diversity and diverse communities, how should we respond in the face of that? Because the existence of the longing to belong exists on all sides.
Some of our greatest wisdom teachers, some of our greatest elders have modeled the behavior. And I'm going to say it's really hard for me to do what I'm about to say. It's really hard for me.
So I don't want to make light of how hard it is, but the truth is, Guy, every single wisdom tradition that has survived teaches us of the brilliance of what one writer, a friend of mine, Valarie Kaur wrote about in her book, See No Stranger, speaking of a foundational belief of the sick faith. Every wisdom tradition at its root seeks to teach us to see no stranger. And every wisdom tradition gets manipulated. That is true.
In Reunion, the epigram for I think it's chapter seven, is a quote from the Talmud. And the quote the Rabbi teaches, while it is not your duty to complete the work, neither you at liberty to neglect the work. So what you've just described is incredibly hard. Our wisdom teachers have taught us, our elders have taught us to love them, and that's really hard. But I'm not at liberty not to try.
Guy Kawasaki:
Just for clarification, when you say they've taught us to love them, you mean the other people?
Jerry Colonna:
Yes. Love even those whom you disagree with. Love even those who would hate you.
Guy Kawasaki:
I see why you say this is so hard. Let's take an extreme, okay. Let's take the most extreme case. You're telling me I'm supposed to love Donald Trump?
Jerry Colonna:
I love that you went there because I had the same difficulty. I absolutely had the same difficulty. Yeah, I am. Here's the way I look at somebody like Donald Trump. I can get clinical and I can sometimes sound like a psychologist, I'm not a trained psychologist, but based on what I know what I see is malignant narcissism. And when I see that, what I see is a boy who was abused by his parents.
And while I struggle to love the adult with ninety-three convictions and how many felony accounts or whatever, I can love that boy. There was at some point in that human's life where it could have gone a different way. I can love him in that moment, and I can endeavor to listen. And I cannot repeat, I can avoid repeating the mistakes of escalating tribalism and hate.
And I know it's hard. I know it's hard, dude. But when I look at the world and we see what's going on right now in the Middle East, where does it end? I'll tell you what it's easier for me to focus my energy on. It's easier for me to focus on the question of who benefits from more, who benefits from division, who benefits from us hating one another, and I can work towards overturning their power.
Guy Kawasaki:
And what's the answer to that question? Who does benefit?
Jerry Colonna:
Almost always people in power.
Guy Kawasaki:
Yeah. Call me naive, Jerry, but I think that no one benefits ultimately because yes, in the short term.
Jerry Colonna:
You're not naive. You're absolutely right. I agree with you completely. They're diminishing themselves whether it's one side of a war or the other side of the war, but there are those who manipulate our longing for belonging. There are those who weaponize our wish for love. And those are the people who are really the bad actors, not necessarily the followers.
See, I think this is what Emma was getting to when she was talking about being a co-conspirator, she's getting to power. She's getting to the question of how do we dismantle the powers that maintain separation and division? How do we call it out? Guy, I'll tell you, as a white man, I can't tell you the number of people of color who've called me or reached out to me and said, "Do you know how infrequently white men of power speak about white supremacy?" And why is that?
When I started speaking about this book, I would often be confronted with, "Who are you to speak about such things?" Because I have benefited from the structures.
And my answer has been consistently, "Who am I to not speak about such things? Who am I as a man not to use the word patriarchy? How dare I be complicit through silence? How dare I? How dare I look at the world and complain about Donald Trump, but not stand up and proffer a vision where business leaders could lead society as they have in the past at times?"
Guy Kawasaki:
Let me ask you a theoretical question that I have struggled with, when Trump was elected and he created these business panels with VIP CEOs. And I used to see Tim Cook sitting to his right or to his left of Donald Trump in the White House and Tim Cook giving Donald Trump tour of the factory in Austin and all that. And at some level I understand Tim Cook is the CEO of Apple, his responsibility is to the shareholders.
And if that takes making sure that the US government doesn't do anything against Apple, I can understand his fiduciary responsibility. But the other half of me, Jerry, is thinking, if not Tim Cook, if not Apple, the most valuable company in the world, if they cannot stand up to him, who the hell can? I don't know what's stronger than shaking my head, but why are people not taking this on? Why are they complicit?
Jerry Colonna:
I'm with you, brother. I'm with you on that. I know your relationship to Apple. I understand that over the years. And I sit here and I listen to you ask that question, and let me put a question to you. What did it feel like for you to watch that happen?
Guy Kawasaki:
To watch Donald Trump getting a tour of the Apple factory sitting next to Tim Cook?
Jerry Colonna:
Yeah.
Guy Kawasaki:
Let me be subtle. I wanted to fucking throw up. Really. I wanted to throw up.
Jerry Colonna:
Can you say more?
Guy Kawasaki:
What else more is there to say? How can you not stand up? To go on a little rant here, and I look at all these social media influencers and they got millions of followers. And I don't know if you follow me on social media, but I definitely have taken a stand. And I look at all these other influencers, and they don't touch politics at all.
And I know because I've talked to them, they say, "I don't want to lose any followers. I don't want to antagonize anybody. This is not my business to comment about social injustice and the threats to democracy. I'm just a social media influencer, blah-blah-blah." And I thank God for Taylor Swift, but other than that.
Jerry Colonna:
Thank God for Taylor Swift, another fierce as fuck young woman who's actually teaching older white guys, older men like how the do you stand up? Because I am with you 100 percent. As I wrote in the book, do you remember the 1980s and the AIDS epidemic? And there was an activist organization called ACT UP, and they plastered New York City with little stickers that said, "Silence equals death."
Whether it's on the southern border of the United States or in a shutdown abortion clinic in Florida, or a healthcare facility that is no longer providing gender-affirming care to a teenager in a world where suicide is the number one cause of death for trans kids, suicide, or where in a world where gun violence is the number one cause of death for children under the age of twenty in the United States.
Guy Kawasaki:
How can that be?
Jerry Colonna:
How can that be? You know how it can be, Guy? Because you named it, because God bless Tim Cook, he's done a fantastic job, but people who have power have a moral responsibility to speak up and to speak out even if it risks your status, even if it risks whatever safety you hold. Because if not, how will you look your descendants in the eye?
Guy Kawasaki:
Exactly. Jerry, if Donald Trump wins, which thanks to our Supreme Court, why we have three branches of government, I'm not sure anymore. But if Donald Trump wins Jerry, they're going to come for me and you. I don't know what we're going to do.
Jerry Colonna:
Take me away, but I will not be silent. We're joking, but we're not joking. We're serious in really what we're saying. And the truth is, Guy, when we started, I didn't know where you stood. I didn't know how you were going to react to this book. I didn't know what you would say. And I am with you on this one because there are too many lives at stake.
Don't make me cry. I saw Emma for dinner last night, and when she hugged me goodbye and kissed me goodbye, she said, "I am so fucking proud of you." Okay. It takes a lot for her because she's so straight. She's sharp in the way she sees things. Maybe they'll drag me off, maybe they'll drag us into jail, but I'll be damned if I go silently.
Guy Kawasaki:
We can be cellies. I want the bottom bunk, okay? In your book, you talk a lot about the value of knowing and understanding and relating to your ancestors. So please explain why this is so important.
Jerry Colonna:
The best way to respond to that is to quote from James Baldwin. He has a brilliant essay called The Price of the Ticket, and it's actually one of the essays in a collection of essays called The Price of the Ticket. And in it, he talks about, for the most part, the descendants of European immigrants. So people who look like me.
And he talks about this movement towards whiteness, this movement towards acceptability and the process of denial of the past as a necessary part of that process. See, the price of that ticket is to disconnect from the reality of who your ancestors were and what they went through. And it's heartbreaking.
And I tell the story of coming into relationship, new relationship with my ancestors. I grew up exquisitely aware of my Italian American ancestors. I was close to those grandparents and all. But what I denied for complicated reasons having to do with my father's depression, what I denied was my father's biological parents. See, my father was adopted at eighteen months old, but he didn't know this until his wedding day.
On his wedding day his adopted mother was so mad at him for marrying my mother that she stood at the back of the church and screamed, "putana," whore, whore, whore, and then screamed, "You're not my son. You were adopted."
And I had a complicated relationship with my father. His alcoholism made it very difficult to be in relationship with him. And one of the things that I do in the book is to try to understand what his relationship was with his parents, having had one mother who gave him up, and the other mother who denied him.
And long story short, I end up in Ireland at the grave of his biological mother, reuniting, if you will, with those ancestors, including an ancestor who turned out had been transported from Ireland during the famine to Australia for having stolen a cow to feed his family.
So my sense of belonging, who the hell do I belong to? Led me down a path of having a wider aperture. Who am I really? And from what place might I understand, say, your family story and where your ancestors came from and what their experience was.
Guy Kawasaki:
Yeah. There seems to be a lot of, shall I say, whitewashing of people's ancestry very conveniently.
Jerry Colonna:
You said it. I call it the gauzy myths of our ancestors, and oh, they were resilient and they came to United States. Why do people on the southern border of the United States cross illegally into United States? That's a good question. My ancestors came here legally. This is the wrap. The truth is, until the 1920s, our immigration laws were so loose, unless you were Asian, our immigration laws, if you were coming from Europe, other than passing a health check, you could come to the United States.
My ancestors came legally because there was no law to break, but they would've come illegally to escape the poverty that they escaped. So my ancestors are more like the families on the southern border of the United States than my relatives might be willing to admit.
Guy Kawasaki:
As they say, there but for the grace of God, go I, right?
Jerry Colonna:
That's right. That's right. That's right. But you make a really important point. We whitewash what happened. We whitewash, we mythologize or romanticize. Part of the journey for me was trying to understand just the level of poverty that existed in Southern Italy and in Ireland when my ancestors immigrated to the United States. People don't leave home lightly.
Guy Kawasaki:
Yeah. Why don't we walk across Mexico and enter the United States? That sounds like a fun thing to do, why don't we do that?
Jerry Colonna:
Yeah. Or why don't we walk even more, make our way from Haiti to Panama crossing Central America, experiencing rape and murder and exploitation on the thin little hope that a child is going to make it across the board. What courage, what amazing strength.
Guy Kawasaki:
The way I look at it is thank God that we still live in a country that people want to get into. That's the way to look at that.
Jerry Colonna:
That's right. And how can we lift that up and build upon that? I get there's so much exploitation that we need a good and safe immigration system. We absolutely need that, but to mistreat other people simply because say they're poor or they're migrants, that is not what our elders taught us to be. Be nice. Be kind.
Guy Kawasaki:
I'll close with a story and let you comment on this. So in 2016, I was in Germany and I met with two of my friends. They're about forty-five years old, and they were saying, "Guy, to this day, we ask our parents and our grandparents, 'How the hell did Hitler take over Germany? How could someone like that so evil take over this country?'"
And then they said to me, "Guy, right now it's 1930 in America. So Guy, you have a question to face. This is about your descendants, right? What kind of ancestor do you want to be?" So they said, "Guy, it's 1930 in America.
So you have a question to face, which is do you want your grandchildren to wonder, 'Did grandpa resist or was grandpa part of it or was he merely complicit? But what did grandpa do?'" And that's the day I decided, screw it, I'm just going to go do it I can at least. I'm not going to just say, "Oh, I don't want to risk my followers." That was the day. I remember that dinner so well.
Jerry Colonna:
I'm grateful to your friends. I'm really grateful to your friends for challenging you the way my daughter challenged me. And it is the 1930s again, I think of that Sinclair Lewis novel. It Can't Happen Here. Here's the thing, it is happening here.
Guy Kawasaki:
It is.
Jerry Colonna:
And this goes beyond even the 2024 election. It's not just democracy that's at risk, although that is profoundly at risk, but it's also human and civil rights at risk right now. When I wrote the book, as I said before, I could not imagine it getting worse, and then it got worse, and it's getting worse.
Guy Kawasaki:
Poor Margaret Atwood. Margaret Atwood is thinking, "Oh, I'm making up this really fantastic piece of fiction called The Handmaid's Tales, inspired by George Orwell 1984. But this is great fiction." And it's not great fiction anymore.
Jerry Colonna:
That's what art does, provokes us. Art warns us. Art challenges us. Like Emma, like your friends. Guy, it's not enough to be an ally. You got to be a co-conspirator.
Guy Kawasaki:
Suffice it to say that this episode did not at all go how I first thought it would go, and probably you feeling the same.
Jerry Colonna:
I'm happy to have it go wherever it went. I really am, and I'm actually really grateful that it went where it went. I'm happy to talk about, I'll come back another time, we can talk about the state of VC because the truth is an executive coach, I coach CEOs of venture-backed companies all the time and VCs, but this is a powerful message that we're talking about.
Guy Kawasaki:
There isn't going to be a venture capital market if there's no democracy. So what difference does it make, right? That's right.
Jerry Colonna:
Yeah, that's right.
Guy Kawasaki:
I hope you enjoyed this interview with Jerry Colonna, from VC to what shall we say humanist philosopher, all around good guy. Sorry for all the profanity, but sometimes you just need to use profanity to truly express how you feel. Thank you, Jerry Colonna. I'm Guy Kawasaki. This is Remarkable People.
My thanks to the Remarkable People team. That would be Madisun Nuismer, producer and co-author of Think Remarkable. Tessa Nuismer, researcher. Shannon Hernandez and Jeff Sieh, sound design mavens. And then there's Luis Magaña, Fallon Yates, and Alexis Nishimura. This is the Remarkable People team, and we're on a mission to make you remarkable. Until next time, mahalo and aloha.