Jerry Colonna: From Venture Capitalist to Conscious Leader

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0:48I'm Guy Kawasaki and this is Remarkable People. We're 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, you know, all that kind of 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.

1:36Now, back then, he was recognized on Forbes' list of the best VCs. He was on Worth's list of the top 25 most generous young Americans. 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. Well, 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.

2:17And now I would say he's a philanthropist and thought leader and just all around good guy.

2:32First 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 like real VC experience and, you know, goes back a long way, flat iron, 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, there's nothing to do with venture capital. In fact, I would say it's the antithesis of venture capital, right?

3:09I don't know if I had to 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. 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 and she's talking about hedge funds. I mean, 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 Learning Annex, maybe about 27, 28 years ago.

4:05And 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 so I just needed to say that because you were fantastic then and you are remarkable now. 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 good life, Jerry. Amen. So you're not deaf. You don't have pancreatic cancer, but you had to follow me. Oh my God, you poor thing. I'll go back to your question. So our hero was in his late 30s as a successful venture capitalist.

5:01And I co-founded Flatiron Partners with Fred Wilson. and spent most of my 30s backing companies in what we would call the first internet wave. So we're talking 96, 97, 98, all the way into 2001, 2002. And that career got interrupted by a massive depression. And the depression was intensely serious. It followed 9-11 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 in the Art of Growing Up. By early 2002, I had transitioned out of Flatiron Partners.

6:00Fred had left and begun the work to start what became Union Square Ventures. And I joined JP 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, 38 years old, was intense because I had attempted it when I was 18. I had failed in my first attempt, thank goodness. But many folks who experience those kinds of feelings two times over oftentimes succeed.

6:54And 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. And 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.

7:46What was not acceptable was continuing to live the life that I was living. And 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 30s. In fact, because of the enormous success I had in my 30s, 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. You asked a simple question, but complicated for me.

8:36How 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 25-year career being something other than the VC who was standing on stage at the Learning Addicts following Guy Kawasaki. So that's my long-winded answer to your complicated question.

9:18What did you do to make this transition? Oh, a lot. I rebuilt myself. D.H. Lawrence has this brilliant poem. There's a line of which that 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.

10:17I started traveling to Tibet. I built a school in Tibet. But ultimately, 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. So if people are listening to this and they know someone who is going through a similar situation, what is your advice to them?

11:12I'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. Parker is in his mid-80s and we often joke he likes to refer to himself as my little brother newsflash I'm only 60 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 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.

12:02And 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.

12:51I 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'd 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 wow shit jerry we could end the recording right here and be done i mean thank you thank you wow thank you for hearing me honestly yeah so let me move to your book so first of all Could you just define belonging to give us a foundation?

14:01Yeah. Again, a little bit more context. In my first book, Reboot, I described the process by which we could use our work, our experience of becoming the leaders we were born to be, to 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.

14:57That 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 the sense of how, 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.

15:51We 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. Because here's the thing, Guy. You and I just started talking today, and we haven't connected in 20 years, 25 years. and our lives intertwined and I overlapped and you were over here and I was over here.

16:35But 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?

17:25Not 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. But Jerry, what about people who seem to be hell-bent on making people feel they don't belong? And in a 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.

18:24So what do you do with that kind of feeling? 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 31 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, who is, I will tell you, man, she is fierce as fuck. She doesn't take shit and she works in education.

19:19She has spent her last 10 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 computer screen.

20:12I 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. So 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?

21:07And I'll leave it at that. 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? 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.

21:55Or 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 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.

22:49looking 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. After my first book came out, I was this beloved pseudo Zen Buddhist. Oh, Jerry. 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. Okay. Okay, let's get one more definition.

23:39Just please define othering. I think that's a great word, othering. Tell us what othering means. Yeah, so to give credit where credit is due, the scholar John A. Powell, who is the founder of the Center for Othering and 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 try we create tribes of who belongs and who doesn't right 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.

24:38It 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. 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, right? Or is it positive? Because it sure can be negative. Well, is community neutral? I wish it were but yeah 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.

25:53In fact, when we look at, say, wars that might be going on even as we speak, every side says, I belong to this, right? 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?

26:43Of course not. The problem isn't the wish. The problem are the conditions that seem to send a message that the only place that child belongs is with a group like that. 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? I mean, they're being exploited. Let's just say, okay, 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? Yeah, that's the conundrum, right?

27:35Because the connection that you're speaking about, the way in which certain individuals and 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, right?

28:24Some 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, Valerie 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.

29:12That 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, really hard. But I'm not at liberty not to try. Now, just for clarification, when you say they've taught us to love them, you mean the other people? Yes. Love even those whom you disagree with. Love even those who would hate you. I mean, I see why you say this is so hard because I don't know.

30:09Let's take an extreme. OK, let's take the most extreme case. You're telling me I'm supposed to love Donald Trump. Yeah, I love that you went there because I had the same difficulty. I absolutely have the same difficulty.

30:28Yeah, 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 93 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 not repeat. I can avoid repeating the mistakes of escalating tribalism and hate.

31:27And 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. And what's the answer to that question? Who does benefit? Almost always people in power. Yeah. Call me naive, Jerry, but I think that no one benefits ultimately. Because, yes, in the short term. You're not naive.

32:14You're absolutely right. I agree with you completely. They are diminishing themselves, whether it's one side of a war or the other side of the war, right? 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 was 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?

32:59Guy, 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? Why is that? When I started speaking about this book, I would often be confronted with, well, 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?