AI transcript
0:00:18 We’re on a mission to make you remarkable and this episode features Jerry Kelowna.
0:00:24 Now Jerry Kelowna and I first met when he was a venture capitalist and I think I was
0:00:25 one too.
0:00:32 I fully expected this episode to be all about venture capital and how you pick out entrepreneurial
0:00:38 teams and what you want in a pitch and you know all that kind of VC crap.
0:00:41 But let’s just say that he is now an executive coach.
0:00:47 He’s an author and he’s founder of Reboot, a leadership development company.
0:00:51 So maybe he was a venture capitalist in his checkered past, but Jerry has transitioned
0:00:55 to executive coaching and has a much higher calling.
0:01:00 Now back then he was recognized on Forbes list of the best VCs.
0:01:05 He was on Worth’s list of the top 25 most generous young Americans.
0:01:10 He was on Upside magazine’s list of the 100 most influential people of the new economy.
0:01:17 He’s the author of two books, Reboot, Leadership in the Art of Growing Up and Reunion, Leadership
0:01:19 in Longing to Belong.
0:01:23 Well in this episode we don’t touch on venture capital very much.
0:01:28 We talk about leadership, we talk about ethics, we talk about morals and we talk about what
0:01:30 really matters in life.
0:01:36 I’m Guy Kawasaki, this is Remarkable People and here comes Jerry Kelowna, former venture
0:01:43 capitalist and now I would say he’s a philanthropist and thought leader and just all around good
0:01:51 guy.
0:01:57 First of all Jerry, when I initially got the proposal for you and of course we said yes
0:02:04 I thought oh finally I can get a VC with like real VC experience and you know goes back
0:02:07 a long way, flat iron, really knows how to pick winners.
0:02:11 I’m thinking oh we’re gonna have this whole podcast about venture capital and what do
0:02:16 you want in a pitch and how you decide on entrepreneurs to invest in and what’s the
0:02:19 key to making a successful startup.
0:02:23 And then I get your book and I say holy shit there’s nothing to do with venture capital.
0:02:29 In fact I would say it’s the antithesis of venture capital right?
0:02:33 I don’t know if I had to trade in my capitalist card or not to do that book.
0:02:39 It’s been a journey since I was an active investor but yeah I think part of what I’m
0:02:46 doing in this new book is just asking people to consider the possibility that people matter
0:02:48 more than profits.
0:02:55 For no one else than me, how did you make this transition from New York finance, venture
0:03:01 capital and now we’re talking about belonging and othering and others and it’s completely
0:03:02 different.
0:03:05 It would be like if I interviewed Jane Goodall and all of a sudden she’s talking about hedge
0:03:08 funds.
0:03:13 I think that the best way to think about this and I was thinking about this conversation
0:03:20 guy and you won’t remember this but there was a talk you did at a learning annex maybe
0:03:32 about 27, 28 years ago and I followed you after that talk back when I was still an active
0:03:39 investor and I will say that one of the great misfortunes of my life is to try to go on
0:03:48 stage following Guy Kawasaki so I just needed to say that because you were fantastic then
0:03:50 and you are remarkable now.
0:03:56 I have to say that if one of the great misfortunes in your life is having to follow me on a stage
0:04:02 I would say you had a pretty goddamn good life chair.
0:04:07 So you’re not deaf, you don’t have pancreatic cancer, but you had to follow me, oh my god
0:04:11 you poor thing.
0:04:19 I’ll go back to your question, so our hero was in his late 30s as a successful venture
0:04:29 capitalist and I co-founded Flatiron Partners with Fred Wilson and spent most of my 30s
0:04:34 backing companies in what we would call the first internet wave.
0:04:43 So we’re talking 96, 97, 98 all the way into 2001, 2002 and that career got interrupted
0:04:50 by a massive depression and the depression was intensely serious.
0:04:55 It followed 9/11 attacks in 2001.
0:05:02 That was certainly a catalytic event for me, but it was really part of a longer arc of
0:05:07 a very challenging experience that stemmed from my own childhood and I detail a lot of
0:05:13 this in my first book, Reboot, Leadership in the Art of Growing Up.
0:05:22 By early 2002 I had transitioned out of Flatiron Partners, Fred had left and begun the work
0:05:28 to start what became Union Square Ventures and I joined JP Morgan, which was our main
0:05:35 investor in Flatiron Partners, thinking that what I didn’t want to do was fundraise but
0:05:41 really what I came to understand was I didn’t want to live in the body that I was in and
0:05:48 as intense as the feelings were, they only grew in intensity to the point where I was
0:05:52 suicidal and I’ve been very open about this.
0:06:00 The danger of suicide at that age, 38 years old, was intense because I had attempted it
0:06:01 when I was 18.
0:06:09 I had failed in my first attempt, thank goodness, but many folks who experience those kinds
0:06:16 of feelings two times over, often time succeed and so it was a very intense period.
0:06:22 After these feelings came up and there’s a really important moment where I was heading
0:06:26 up the New York City Olympic bid effort.
0:06:32 We were trying to bring the 2012 games to the city and I left an Olympic Committee meeting
0:06:38 which was down in downtown New York, right near the World Trade Center, what was ground
0:06:44 zero and rather than leaping in front of a subway train, which is what the feeling was,
0:06:52 I wisely called my therapist who said, “Come to my office, we have to talk,” and so that’s
0:06:53 what I did.
0:07:00 The reason I often speak to that moment as the moment of transition was I always feel
0:07:05 like I had two choices, to live or to die.
0:07:11 What was not acceptable was continuing to live the life that I was living and you can
0:07:16 probably relate to this given there the number of people that you’ve spoken to in your own
0:07:19 journey in your own life.
0:07:25 Despite the enormous success that I had in my thirties, in fact, because of the enormous
0:07:32 success that I had in my thirties, I felt more and more distant from my true self.
0:07:38 I often describe it as the inner me and the outer me were in conflict and the crazy thing
0:07:47 guy is that the more I tap dance my way and performed well, the worse I felt inside.
0:07:51 The more success I had, the worse I felt inside.
0:07:56 You asked a simple question, but complicated for me.
0:08:02 How did I go from being a successful VC to writing a book about systemic othering and
0:08:04 our universal longing to belong?
0:08:12 It was through a broken heart and pausing and tending to that and that began what has
0:08:20 now been a twenty five year career being something other than the VC who was standing
0:08:24 on stage at the learning addicts follow guy Kawasaki.
0:08:38 So that’s my long winded answer to your complicated question.
0:08:41 What did you do to make this transition?
0:08:43 Oh, a lot.
0:08:50 I rebuilt myself, DH Lawrence has this brilliant poem.
0:08:56 There’s a line of which that it goes something like this, are you willing to be erased to
0:09:00 be sponged out because only then will you be able to change.
0:09:09 And so I entered this period three or four years where I started studying Buddhism.
0:09:14 I went to psychoanalysis three times a week.
0:09:18 I did art therapy, I did dance therapy.
0:09:26 I tried to write a novel about a man in midlife having a crisis and I traveled the world.
0:09:30 I went across the polar ice cap in Greenland.
0:09:33 I rafted the Grand Canyon.
0:09:36 I went down to Chile and rafted rivers in Chile.
0:09:38 I started traveling to Tibet.
0:09:41 I built a school in Tibet.
0:09:49 But ultimately got what really started to change was I started to sit still and meditate
0:09:54 and do what I call a practice of radical self-inquiry.
0:09:56 Who am I really?
0:09:58 What is this person inside?
0:10:04 Forget the performing monkey that I had trained myself to be.
0:10:06 Who am I really?
0:10:10 And how can I live as close as possible to that?
0:10:18 And that work led me eventually to becoming a coach and executive coach and then writer
0:10:20 and doing the work that I do today.
0:10:27 So if people are listening to this and they know someone who is going through a similar
0:10:31 situation, what is your advice to them?
0:10:38 I’ll share what I came to understand through the work of one of my dearest friends and
0:10:44 a mentor of mine, a brilliant Quaker writer named Parker Palmer.
0:10:50 Parker is in his mid-80s and we often joke he likes to refer to himself as my little
0:10:52 brother, News Flash.
0:10:53 I’m only 60.
0:10:54 Okay.
0:11:01 Parker, you’ve got the math wrong, but he wrote a book called Let Your Life Speak.
0:11:07 And it’s a Quaker aphorism which has a double meaning, first of which is to let the inside
0:11:11 of you speak through your actions.
0:11:14 And the second is to let your life speak to you.
0:11:20 In that book, which I read when I was in the midst of this depression, in that book he describes
0:11:22 his own journey with depression.
0:11:30 And he describes a particular period of depression where every afternoon a neighbor of his, Bill,
0:11:37 would stop by his house and sit next to him and not do the thing that the depressed person
0:11:39 almost can’t stand.
0:11:41 Bill would not cheer him up.
0:11:44 I know this is counterintuitive.
0:11:48 Bill would not sit there and say, “Come on, buck up.
0:11:49 Look at the sunshine.
0:11:51 It’s beautiful outside.”
0:11:57 What Bill would do is sit next to Parker and say, “Looks like you’re having a hard day
0:11:58 today.”
0:12:00 Or, “You look stronger today.”
0:12:07 And sometimes Bill would take Parker’s shoes off and rub his feet because as Parker described,
0:12:11 it was the only spot on his body he could bear to be touched.
0:12:18 I was so moved by that scene of a friend not trying to fix, not trying to make it better,
0:12:25 but with deep compassion being able to bear witness to the difficult feelings and do
0:12:28 the smallest of human gestures.
0:12:30 Just rub some feet.
0:12:35 Let the depressed person know they’re not alone.
0:12:38 And so I’ll speak to anybody who’s feeling that right now.
0:12:39 You’re not alone.
0:12:44 You’ll be surprised at the number of people you admire who also struggle.
0:12:50 And take comfort in the fact that no matter what your depression tells you, it’s a lie.
0:12:52 You are lovable.
0:12:54 You are worthy.
0:12:58 And it will pass and let somebody rub your feet.
0:12:59 Wow.
0:13:01 Shit, Jerry.
0:13:04 We could end the recording right here and be done, I mean.
0:13:05 Thank you.
0:13:06 Thank you.
0:13:07 Wow.
0:13:11 You’re cheering me, honestly.
0:13:14 So let me move to your book.
0:13:20 So first of all, could you just define belonging to give us a foundation?
0:13:21 Yeah.
0:13:23 Again, a little bit more context.
0:13:32 In my first book, Reboot, I described the process by which we could use our work, our
0:13:39 experience of becoming the leaders we were born to be, to complete our process and be
0:13:40 an adult.
0:13:48 And I talk about, in our childhood, the fact that one way to think about what experiences
0:13:55 we have is to see ourselves constantly in pursuit of three things, to love and be loved,
0:14:02 to feel safe physically, emotionally, experientially, spiritually, and to know without a shadow
0:14:05 of a doubt that we belong.
0:14:13 Now I wrote about that and I was blown away by the number of people who said, “That story
0:14:16 is my story.
0:14:18 That is my childhood.
0:14:20 That is how I believe.
0:14:25 I believe that in order to feel safe, I must work myself to the bone.”
0:14:27 I was guilty of that.
0:14:33 Or I believe that in order for me to feel worthy of love, I have to please everybody around
0:14:37 me and deny my own feelings.
0:14:39 I was also guilty of that.
0:14:45 But this notion of belonging stayed with me after I wrote the book.
0:14:53 And what I wanted to do was to really explore the sense of how, in Buddhism, we often talk
0:15:00 about this notion of interdependence and the way we are all interconnected to one another.
0:15:04 For me, the pandemic was a perfect experience of this.
0:15:11 We needed each other in ways that we were not always cognizant of it.
0:15:13 We needed each other to take care of each other.
0:15:17 We needed each other in some cases to wear masks.
0:15:20 We needed each other possibly to take a vaccine.
0:15:22 We needed each other.
0:15:27 And when I look at the struggles that we have, and I did not imagine that the world would
0:15:38 be as divided as it is today, even back in 2020, what struck me was the degree to which
0:15:42 we can feel groundless in our sense of belonging.
0:15:43 Because here’s the thing, Guy.
0:15:49 You and I just started talking today, and we haven’t connected in 20 or 25 years.
0:15:55 And our lives intertwined, and I overlapped, and you were over here, and I was over here.
0:15:57 But the truth is, we’re connected.
0:16:03 We belong to one another, even if your political views are different, even if your religious
0:16:06 views are different.
0:16:11 And in exploring this question, what it motivated me was to ask a deep and profound
0:16:13 question.
0:16:21 What is the responsibility of someone who is like me, privileged, lucky as shit, powerful,
0:16:25 no matter how I feel, I have power?
0:16:32 What is my responsibility in a world, and I’m going to get a little dramatic here, in
0:16:38 a world where babies are murdered for ideology, or grandmothers are shot down in a supermarket,
0:16:42 or worshipers in a temple are killed?
0:16:44 What is my responsibility?
0:16:51 Not from a guilt perspective, but what can I do to make a difference?
0:16:56 To me, this is the most logical extension of the pursuit of love, safety, and belonging.
0:17:06 See, if I can make you feel that you belong through the power of interconnection, you
0:17:08 will make me feel that I belong.
0:17:18 But Jerry, what about people who seem to be hell-bent on making people feel they don’t
0:17:25 belong, and in a sense, I think what they believe is, I’m going to make some people
0:17:30 feel like they belong, and some people feel like they don’t belong, so that the people
0:17:34 who feel like they belong feel they belong stronger.
0:17:42 So, it’s by defining who’s on the outs that helps us strengthen who’s on the in, as if
0:17:46 it’s a zero-sum game, so what do you do with that kind of feeling?
0:17:48 That you just named it.
0:17:56 The problem with applying a zero-sum game mentality to human beings is that babies die.
0:18:02 Mental extension, some will needlessly die.
0:18:09 As you know from reading the book, what sparked me doing this exploration was a challenge by
0:18:15 my daughter, who’s now 31, who joined millions and millions of people, and I want to just
0:18:22 acknowledge that my children’s mom is Chinese American, my children identify as biracial.
0:18:32 I am white, Italian, and Irish ancestry, and my daughter, who has, I will tell you, man,
0:18:39 she is fierce as fuck, she doesn’t take shit, and she works in education, she has spent
0:18:46 her last 10 years helping build charter schools in low-income neighborhoods, specifically in
0:18:50 Nashville, motivated by making a difference in the world.
0:18:55 You should have her on your podcast, forget her father, she’s remarkable.
0:19:02 I was motivated and challenged by her with a simple phrase that she used to say to me
0:19:03 all the time.
0:19:07 When I would think I was doing enough, she would say, “Dad, it’s not enough to be an
0:19:13 ally, you have to be a co-conspirator,” and when she took to the streets to protest the
0:19:21 murder of George Floyd in the middle of a damn pandemic, and I was sitting on this farm
0:19:29 that I live on in Colorado, safe and comfortable and worrying about the world from the safety
0:19:31 behind my computer screen.
0:19:37 I organized myself around this question of how can we be better humans so that we can
0:19:39 then be better leaders?
0:19:44 And her challenge to me was, “What are you doing, Dad, in a world where this sort of
0:19:46 thing happens every day?”
0:19:55 So I’m totally lost in my own thoughts, but what motivated me as I write in the book was
0:20:03 to be the ancestor worthy of my descendants, to look back and say, “It’s not enough, guy,
0:20:10 that I helped create a bunch of companies, 150, 200 companies, but what am I doing?
0:20:15 What is the legacy that I’m going to leave when I turn to dust?”
0:20:25 And writing a book like Reunion where I take people through this whole question of what
0:20:30 is our responsibility, and I’ll leave it at that.
0:20:38 Okay, so now when Emma says to you this challenge about being a co-conspirator, what does it
0:20:42 mean in actual terms to be a co-conspirator?
0:20:44 That’s a great question.
0:20:53 For me, it means to use what skills and power and privilege I have to tilt at the windmill,
0:20:54 to do the work.
0:20:56 I don’t know why.
0:20:58 God gave me a gift.
0:21:02 I can put words together in such a way that people listen to me.
0:21:05 I can do that in writing and I can do that in speaking.
0:21:17 Now I can do that to quote an old friend of yours to sell sugar water, or I can do that
0:21:20 to look at the questions that really plague us.
0:21:26 And from where I sit, there are two big challenges facing the species.
0:21:33 One is climate change, and one is the way in which we systemically other people.
0:21:40 One is the way we make the other person, the person who is not like us, unacceptable.
0:21:46 And we see that throughout this through line of whether it’s denial of healthcare rights
0:21:53 to individuals because of how they identify, or the denial of civil rights, or literally
0:22:02 the denial of lifesaving care because of who they are or who they love or how they worship.
0:22:03 This is a plague.
0:22:09 So being a co-conspirator means two things.
0:22:15 Looking at the ways in which I have been complicit in and benefited from the world as it is,
0:22:20 even if I don’t like the world as it is, and considering what is it that I’m willing to
0:22:25 give up that matters to me, that I love to see that difference.
0:22:32 Guy, after my first book came out, I was this beloved pseudo Zen Buddhist.
0:22:37 Oh, Jerry, right.
0:22:44 And here I am, putting out a book that challenges people to really question their assumptions.
0:22:46 They may not like me after.
0:22:52 My friends in the venture business disagree with me, some of them do.
0:22:55 But that’s what it means to be a co-conspirator.
0:22:59 Okay, let’s get one more definition.
0:23:02 Just please define othering.
0:23:04 I think that’s a great word, othering.
0:23:06 Tell us what othering means.
0:23:14 Yeah, so to give credit where credit is due, the scholar John A. Powell, who is the founder
0:23:20 of the Center for Othering and Belonging at UC Berkeley, is the first person I heard use
0:23:22 that term.
0:23:30 And Powell is a brilliant black legal mind, but really one of the giants in trying to
0:23:40 understand beyond the term systemic racism, which doesn’t encompass all of the ways in
0:23:45 which we create tribes of who belongs and who doesn’t.
0:23:53 And it might be the Japanese during World War II, or it might be the Chinese in America
0:23:57 during the pandemic or during the Chinese Exclusion Act.
0:24:02 It goes beyond our normal conceits of prejudice.
0:24:04 It encompasses all of that.
0:24:13 And what’s beautiful about the term is that it does lead exactly into this notion of belonging,
0:24:20 where imagine a world where any child knew, every child knew, down to their core that
0:24:22 they belonged.
0:24:27 I know it’s not possible in my lifetime, but I’ll be damned if I don’t try.
0:24:35 But what if this child feels like he or she belongs to a gang or belongs to something
0:24:38 that you would not consider positive?
0:24:40 Belonging is neutral, right?
0:24:41 Or is it positive?
0:24:44 Because it sure can be negative.
0:24:47 Well is community neutral?
0:24:48 I wish it were, but yeah.
0:24:51 I think you raise a really important point.
0:25:00 I can create a sense of belonging in an environment where what brings us together might be violence.
0:25:07 And I think what you’re backing into is, there is a universal longing to belong.
0:25:13 And that can be exploited for evil, or that can be used for good.
0:25:23 In fact, when we look at say wars that might be going on even as we speak, every side says
0:25:26 I belong to this, right?
0:25:31 And that wish for belonging, and we know this to be true, is exploited by those who have
0:25:36 power to maintain or enhance their power.
0:25:42 So yes, the longing to belong can be weaponized, just like the longing for love and safety
0:25:44 can be weaponized.
0:25:45 That is true.
0:25:52 And so we, I think we’re called to look at this larger question in the light just the
0:25:55 way you’re looking the question right now.
0:26:01 Is the answer to deny belonging to that child who seeks a sense of connection and community
0:26:02 by joining a gang?
0:26:03 Of course not.
0:26:05 The problem isn’t the wish.
0:26:13 The problem with the conditions that seem to send a message that the only place that
0:26:16 child belongs is with a group like that.
0:26:25 If there are people who see that the only group that they belong to are Nazis or white
0:26:32 nationalists or Christian nationalists or MAGA or whatever, what do you do with that?
0:26:35 I mean, they’re being exploited.
0:26:41 Let’s just say, okay, I think they’re being exploited that people are more, more similar
0:26:43 than they’re different.
0:26:49 And we could all get along, but some people just want to whip them into a fervor.
0:26:51 What do you do with that?
0:26:55 Yeah, that’s the conundrum, right?
0:27:00 Because the connection that you’re speaking about the way in which certain individuals
0:27:07 and certain groups will come together in a shared belief about the negative experience
0:27:13 of the other person, the negative qualities of the other person, whether it’s white nationalists
0:27:22 or white supremacists or those who would deny health care rights to women, for example,
0:27:28 and find common cause with a group of people.
0:27:34 What you’re asking is how should those of us who seek to find to build diversity and
0:27:38 diverse communities, how should we respond in the face of that?
0:27:44 Because the existence of the longing to belong exists on all sides, right?
0:27:50 Some of our greatest wisdom teachers, some of our greatest elders have modeled the behavior.
0:27:55 And I’m going to say it’s really hard for me to do what I’m about to say.
0:27:57 It’s really hard for me.
0:28:01 So I don’t want to make light of how hard it is.
0:28:08 But the truth is, guy, every single wisdom tradition that has survived teaches us of
0:28:16 the brilliance of what one writer, a friend of mine, Valerie Core, wrote about in her book
0:28:23 “See No Strangers,” speaking of a foundational belief of the sick faith.
0:28:29 Every wisdom tradition, at its root, seeks to teach us to see no stranger, and every
0:28:32 wisdom tradition gets manipulated.
0:28:33 That is true.
0:28:40 In Reunion, the epigram for I think it’s chapter seven is a quote from the Talmud.
0:28:47 And the quote the rabbi teaches, “While it is not your duty to complete the work, neither
0:28:51 you at liberty to neglect the work.”
0:28:54 So what you’ve just described is incredibly hard.
0:28:56 Our wisdom teachers have taught us.
0:28:58 Our elders have taught us to love them.
0:29:00 And that’s really, really hard.
0:29:03 But I’m not at liberty not to try.
0:29:11 Now, just for clarification, when you say they’ve taught us to love them, you mean the other
0:29:12 people.
0:29:13 Yes.
0:29:18 Love even those whom you disagree with.
0:29:20 Love even those who would hate you.
0:29:30 I mean, I see why you say this is so hard, because I don’t know, let’s take an extreme,
0:29:31 okay?
0:29:33 Let’s take the most extreme case.
0:29:36 You’re telling me I’m supposed to love Donald Trump?
0:29:41 Yeah, I love that you went there, because I had the same difficulty.
0:29:44 I absolutely had the same difficulty.
0:29:49 Yeah, I am.
0:29:52 Here’s the way I look at somebody like Donald Trump.
0:29:58 I can get clinical, and I can sometimes sound like a psychologist.
0:30:00 I’m not a trained psychologist.
0:30:06 But based on what I know, what I see is malignant narcissism.
0:30:12 And when I see that, what I see is a boy who was abused by his parents.
0:30:21 And while I struggle to love the adult with 93 convictions and convictions and how many
0:30:25 felony counts or whatever, I can love that boy.
0:30:32 There was at some point in that human’s life where it could have gone a different way.
0:30:39 I can love him in that moment, and I can endeavor to listen, and I cannot repeat.
0:30:47 I can avoid repeating the mistakes of escalating tribalism and hate.
0:30:50 And I know it’s hard.
0:30:51 I know it’s hard, dude.
0:30:57 But when I look at the world, and we see what’s going on right now in the Middle East, where
0:30:58 does it end?
0:31:02 I’ll tell you what it’s easier for me to focus my energy on.
0:31:09 It’s easier for me to focus on the question of who benefits from more, who benefits from
0:31:13 division, who benefits from us hating one another.
0:31:16 And I can work towards overturning their power.
0:31:18 And what’s the answer to that question?
0:31:21 Who does benefit?
0:31:23 Almost always people in power.
0:31:24 Yeah.
0:31:31 Very naive, Jerry, but I think that no one benefits ultimately because, yes, the short
0:31:32 term.
0:31:33 You’re not naive.
0:31:34 You’re absolutely right.
0:31:37 I agree with you completely.
0:31:43 They’re diminishing themselves, whether it’s one side of a war or the other side of the
0:31:44 war, right?
0:31:50 But there are those who manipulate our longing for belonging.
0:31:53 There are those who weaponize our wish for love.
0:31:59 And those are the people who are really the bad actors, not necessarily the followers.
0:32:05 See, I think this is what Emma was getting to when she’s talking about being a co-conspirator.
0:32:07 She’s getting to power.
0:32:14 She’s getting to the question of how do we dismantle the powers that maintain separation
0:32:16 and division?
0:32:18 How do we call it out?
0:32:23 Guy, I’ll tell you, as a white man, I can’t tell you the number of people of color who
0:32:29 have called me or reached out to me and said, “Do you know how infrequently white men of
0:32:32 power speak about white supremacy?
0:32:33 Why is that?”
0:32:39 When I started speaking about this book, I would often be confronted with, “Well, who
0:32:42 are you to speak about such things?”
0:32:45 Because I have benefited from the structures.
0:32:52 And my answer has been consistently, who am I to not speak about such things?
0:32:56 Who am I as a man not to use the word patriarchy?
0:33:00 How dare I be complicit through silence?
0:33:01 How dare I?
0:33:08 How dare I look at the world and complain about Donald Trump, but not stand up and proffer
0:33:14 a vision where business leaders could lead society?
0:33:17 What’s they have in the past at times?
0:33:24 Up next on Remarkable People, I end up in Ireland at the grave of his biological mother,
0:33:30 reuniting, if you will, with those ancestors, including an ancestor who turned out had been
0:33:38 transported from Ireland during the famine to Australia for having stolen a cow to feed
0:34:06 his family.
0:34:13 Let me ask you a theoretical question that I have struggled with.
0:34:22 When Trump was elected and he created these business panels with VIP CEOs, I used to see
0:34:28 Tim Cook sitting to his right or to his left of Donald Trump in the White House and Tim
0:34:33 Cook giving Donald Trump tour of the factory in Austin and all that.
0:34:39 And at some level, I understand Tim Cook is the CEO of Apple, his responsibility is to
0:34:44 the shareholders and if that takes making sure that the US government doesn’t do anything
0:34:49 against Apple, I can understand his fiduciary responsibility.
0:34:56 But the other half of me, Jerry, is thinking, if not Tim Cook, if not Apple, the most valuable
0:35:02 company in the world, if they cannot stand up to him, who the hell can?
0:35:07 I don’t know what’s stronger than shaking my head, but I like, why are people not taking
0:35:08 this on?
0:35:10 Why are they complicit?
0:35:11 I’m with you, brother.
0:35:13 I’m with you on that.
0:35:15 I know your relationship to Apple.
0:35:18 I understand that over the years.
0:35:23 And I sit here and I listen to you ask that question.
0:35:25 And let me put a question to you.
0:35:29 What did it feel like for you to watch that happen?
0:35:35 To watch Donald Trump getting a tour of the Apple factory sitting next to Tim Cook?
0:35:36 Well, let me be sorry.
0:35:39 I wanted to fucking throw up really.
0:35:41 I wanted to throw up.
0:35:42 Can you say more?
0:35:44 What else more is there to say?
0:35:51 I mean, how can you not stand up and to go on a little rant here?
0:35:55 And I look at all these quote unquote social media influencers, right?
0:35:59 And they got like, got millions of followers and I don’t know if you follow me on social
0:36:02 media, but I definitely have taken a stand.
0:36:08 And I look at all these other influencers and they don’t touch politics at all.
0:36:12 And I know because I’ve talked to them, they say, well, I don’t want to lose any followers.
0:36:14 I don’t want to antagonize anybody.
0:36:21 This is not my business to comment about social injustice and the threats to democracy.
0:36:23 I’m just a social media influencer, blah, blah, blah.
0:36:26 And thank God for Taylor Swift.
0:36:29 But other than that, thank God for Taylor Swift.
0:36:35 Another fiercest fuck young woman who’s actually teaching older white guys, older men, like
0:36:38 how the fuck do you stand up?
0:36:41 Because I am with you 100 percent.
0:36:45 As I wrote in the book, do you remember the 1980s in the AIDS epidemic?
0:36:50 And there was an activist organization called Act Up and they plastered New York City with
0:36:55 little stickers that said silence equals death, whether it’s on the southern border of the
0:37:05 United States or in a shut down abortion clinic in Florida or a health care facility
0:37:11 that is no longer providing gender affirming care to a teenager.
0:37:19 In a world where suicide is the number one cause of death for trans kids, suicide.
0:37:25 Or where in a world where gun violence is the number one cause of death for children
0:37:30 under the age of 20 in the United States.
0:37:31 How can that be?
0:37:32 How can that be?
0:37:34 How can that be?
0:37:36 You know how it can be, guy?
0:37:39 Because you named it because God blessed him cook.
0:37:45 He’s done a fantastic job, but people who have power have a moral responsibility to speak
0:37:48 up and to speak out.
0:37:58 Even if it risks your status, even if it risks whatever safety you hold, because if not,
0:38:01 how will you look your descendants in the eye?
0:38:02 Exactly.
0:38:08 Jerry, if Donald Trump wins, which thanks to our Supreme Court, why we have three branches
0:38:10 of government, I’m not sure anymore.
0:38:14 But if Donald Trump wins, Jerry, they’re going to come for me and you.
0:38:16 I don’t know what we’re going to do.
0:38:17 Take me away.
0:38:19 But I will not be silent.
0:38:23 I’m not going to be, I’m not going to, okay.
0:38:25 We’re joking, but we’re not joking.
0:38:29 We’re serious and really what we’re saying.
0:38:33 And the truth is, guy, when we started, I didn’t know where you stood.
0:38:36 I didn’t know how you were going to react to this book.
0:38:41 I didn’t know what you would say and I am with you on this one because there are too
0:38:44 many lives at stake.
0:38:45 Don’t make me cry.
0:38:47 I saw Emma for dinner last night.
0:38:51 And when she hugged me goodbye and kissed me goodbye, she said, I am so fucking proud
0:38:52 of you.
0:38:53 Okay.
0:38:57 It takes a lot for her because she’s so straight.
0:39:01 I mean, she’s sharp in the way she sees things.
0:39:02 Maybe they’ll drag me off.
0:39:06 Maybe they’ll drag us into jail, but I’ll be damned if I go silently.
0:39:07 We can be sellies.
0:39:14 I want the bottom bunk, okay?
0:39:21 In your book, you talk about a lot about the value of knowing and understanding and
0:39:25 relating to your ancestors.
0:39:29 So please explain why this is so important.
0:39:36 The best way to respond to that is to quote from James Baldwin, he has a brilliant essay
0:39:41 called the price of the ticket and it’s actually one of the essays in a collection of essays
0:39:48 called the price of the ticket and in it, he talks about it for the most part, the descendants
0:39:50 of European immigrants.
0:39:56 So people who look like me and he talks about this movement towards whiteness, this movement
0:40:07 towards acceptability and the process of denial of the past as a necessary part of that process.
0:40:14 See, the price of that ticket is to disconnect from the reality of who your ancestors were
0:40:23 and what they went through and it’s heartbreaking and I tell the story of coming into relationship,
0:40:27 new relationship with my ancestors.
0:40:33 I grew up exquisitely aware of my Italian American ancestors.
0:40:40 I was close to those grandparents and all but what I denied for complicated reasons of having
0:40:48 to do with my father’s depression, what I denied was my father’s biological parents.
0:40:55 My father was adopted at 18 months old but he didn’t know this until his wedding day.
0:41:01 On his wedding day, his adopted mother was so mad at him for marrying my mother that
0:41:07 she stood at the back of the church and screamed putana putana putana whore whore whore and
0:41:13 then screamed you’re not my son, you were adopted and I had a complicated relationship
0:41:20 with my father. His alcoholism made it very, very difficult to be in relationship with
0:41:29 him and one of the things that I do in the book is to try to understand what his relationship
0:41:36 was with his parents having had one mother who gave him up and the other mother who denied
0:41:44 him and long story short I end up in Ireland at the grave of his biological mother reuniting
0:41:51 if you will with those ancestors including an ancestor who turned out had been transported
0:41:59 from Ireland during the famine to Australia for having stolen a cow to feed his family.
0:42:06 So my sense of belonging, who the hell do I belong to led me down a path of having a
0:42:14 wider aperture on who it was that who am I really and from what place might I understand
0:42:22 say your family story and where your ancestors came from and what their experience was.
0:42:34 There seems to be a lot of, shall I say, whitewashing of people’s ancestry very conveniently.
0:42:39 You said it, I call it the gauzy myths of our ancestors and oh they were resilient and
0:42:43 they came to the United States and why do people on the southern border of the United
0:42:50 States cross illegally into the United States? It’s a good question. Why my ancestors came
0:42:58 here legally? This is the rap. The truth is until the 1920s our immigration laws were
0:43:04 so loose other than unless you were Asian our immigration laws if you were coming from
0:43:10 Europe other than passing a health check you could come to the United States. So there
0:43:16 was no crossing my ancestors came legally because there was no law to break but they
0:43:22 would have come illegally to escape the poverty that they escaped. So my ancestors are more
0:43:30 like the families on the southern border of the United States than my relatives might
0:43:36 be willing to admit. As they say there but for the grace of God go I am right. That’s
0:43:42 right. Yeah. That’s right. Yeah. That’s right. But you make a really important point. We
0:43:50 whitewash what happened. We whitewash, we mythologize or romanticize. Part of the journey
0:43:56 for me was trying to understand just the level of poverty that existed in southern Italy
0:44:04 and in Ireland when my ancestors immigrated to the United States. People don’t leave home
0:44:11 lightly. Yeah. Yeah. Yeah. Why don’t we walk across Mexico and enter the United States?
0:44:15 This sounds like a fun thing to do. Why don’t we do that? Yeah. Yeah. Or why don’t we walk
0:44:24 even more. We’ll make our way from Haiti to Panama. Yeah. Crossing Central America experiencing
0:44:31 rape and murder and exploitation on the thin little hope that a child is going to make
0:44:39 it across the border. Yeah. What courage. What amazing strength. The way I look at it
0:44:46 is thank God that we still live in a country that people want to get into. That’s the way
0:44:53 to look at that. That’s right. And how can we lift that up and build upon that? I get
0:45:01 there’s so much exploitation that we need a good and safe immigration system. We absolutely
0:45:10 need that. But to mistreat other people simply because say they’re poor or they’re migrants.
0:45:17 That is not what our elders taught us to be. Be nice. Be kind. I’ll close with a story
0:45:25 and let you comment on this. So in 2016 I was in Germany and I met with two of my friends.
0:45:31 They’re about 45 years old and they were saying God to this day we ask our parents and our
0:45:35 grandparents how the hell did Hitler take over Germany? How could someone like that
0:45:43 so evil take over this country? And then they said to me you know guy right now it’s 1930
0:45:49 in America. So guy you have a question to face. This is about your descendants. Right.
0:45:53 What kind of ancestor do you want to be? So I said you know guy it’s 1930 in America.
0:46:00 So you have a question to face which is do you want your grandchildren to wonder did
0:46:07 grandpa resist or was grandpa part of it or was he merely complicit? But what did grandpa do?
0:46:15 And that’s the day I decided screw it. I’m just going to go you know do what I can at least. I’m
0:46:22 not going to just say oh I don’t want to risk my followers. That was the day. I remember that dinner
0:46:28 so well. I’m grateful to your friends. I’m really grateful to your friends for challenging you the
0:46:34 way my daughter challenged me. Yeah. And it is. It is the 1930s again. I think of that Sinclair
0:46:41 Lewis novel. It can’t happen here. Here’s the thing. It is happening. It is. And this goes beyond
0:46:50 even the 2024 election. It’s not just democracy that’s at risk although that is profoundly at risk.
0:46:57 But it’s also human and civil rights at risk right now. And when I wrote the book
0:47:06 as I said before I could not imagine it getting worse and then it got worse and it’s getting worse.
0:47:12 I mean poor Margaret Atwood right. Margaret Atwood is thinking oh I’m making up this really
0:47:21 fantastic piece of fiction called The Handmaid’s Tale. It’s inspired by George Orwell 1984. But
0:47:27 this is like great fiction and it’s not great fiction anymore. But that’s what art does right.
0:47:36 Art provokes us. Art warns us. Art challenges us like Emma like your friends. Guy it’s not
0:47:42 enough to be an ally. You got to be a co-conspirator. Suffice it to say that this episode did not at all
0:47:48 go how I first thought it would go. And probably you feeling the same. I’m happy to have it go
0:47:54 wherever it went. I really am. And I’m actually really grateful that it went where it went.
0:47:58 I’m happy to talk about I’ll come back another time we can talk about the state of V.C.
0:48:06 because the truth is an executive coach a coach CEOs of venture back companies all the time and
0:48:12 V.C.s. But this is a powerful message that we’re talking about. You know what there isn’t going
0:48:18 to be a venture capital market if there’s no democracy. So what difference does it make right.
0:48:26 That’s right. That’s right. Remember the phrase people are more important than profits. He came
0:48:32 from a venture capital background and has progressed to become a humanist and philosopher.
0:48:38 This is very different from the billionaire bros who only care about capital gains tax
0:48:44 and making crypto successful. But I digress. Sorry about the profanity in this episode but
0:48:51 sometimes you just need to use profanity to truly express how you feel. Thank you Jerry Kelowna.
0:48:59 I’m Guy Kawasaki. This is Remarkable People. My thanks also to the Remarkable People team.
0:49:06 They are, of course, Matt as a Neismar producer and co-author of Think Remarkable. And then there’s
0:49:13 Tessa Neisler our ACE researcher. Then there’s the ACE sound design team of Shannon Hernandez
0:49:20 and Jeff C. And finally there’s Louise Magana, Fallon Yates and Alexis Nishimura. This is the
0:49:28 Remarkable People team and we are on a mission to make you remarkable and humanist and empathetic
0:49:40 and caring. Till next time, Mahalo and Aloha. This is Remarkable People.
In this episode of Remarkable People, join host Guy Kawasaki as he speaks with Jerry Colonna, an accomplished executive coach, author, and the founder of Reboot. Jerry shares his remarkable journey from being a successful venture capitalist to becoming a passionate advocate for leadership, ethics, and what truly matters in life. Exploring themes from his books Reboot: Leadership and the Art of Growing Up and Reunion: Leadership and Longing to Belong, Colonna dives into the importance of belonging, the dangers of systemic othering, and the responsibility of those in positions of power to create a more inclusive and compassionate world. This conversation goes beyond the typical venture capital discussion, touching on issues of mental health, privilege, and the moral imperative to speak up against injustice. Listeners will be inspired by Jerry’s personal journey and his vision for ethical leadership that prioritizes people over profits.
—
Guy Kawasaki is on a mission to make you remarkable. His Remarkable People podcast features interviews with remarkable people such as Jane Goodall, Marc Benioff, Woz, Kristi Yamaguchi, and Bob Cialdini. Every episode will make you more remarkable.
With his decades of experience in Silicon Valley as a Venture Capitalist and advisor to the top entrepreneurs in the world, Guy’s questions come from a place of curiosity and passion for technology, start-ups, entrepreneurship, and marketing. If you love society and culture, documentaries, and business podcasts, take a second to follow Remarkable People.
Listeners of the Remarkable People podcast will learn from some of the most successful people in the world with practical tips and inspiring stories that will help you be more remarkable.
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