Reboot: Jerry Colonna and the pursuit of lemon drops

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What do you do when you come to that realization in your life that your pursuits are leaving you with a sense of emptiness?

Jerry Colonna is one of the founders of Reboot which offers coaching services for individuals, teams and entire organizations.

Jerry’s ah-ha moment was when he realized he was always pursuing the feeling of having enough and that he never was reaching that goal. Now, he helps other founders and entrepreneurs find their fullest potential.

Jerry Colonna

Jerry Colonna


Jerry Colonna is one of the founders of Reboot which offers coaching services for individuals, teams and entire organizations.


Full Interview Transcript

Andrew: Hey, there, freedom fighters. My name is Andrew Warner. I’m the founder Mixergy, where I interview entrepreneurs about how they built their businesses for an audience of real entrepreneurs who are often building their businesses while they listen.
And I’m actually here in New York, only slept four hours last night on the plane. Thankfully, it was an empty plane, so I just laid down on four seats, which I hadn’t done since I was a kid. But I wanted to get sleep. And I wanted to do this interview.

And I came here to support my wife, who asked me to come to an event that her company is a part of. She’s with that PagerDuty. And I said, “The one thing I don’t want to miss is my interview with Jerry Colonna.” And frankly, I don’t want to miss any work, but I definitely want to miss that. He adjusted his schedule and our set time so that we could do this interview. I sat and I read his book, and then I thought, “Am I wrong to be working this hard? Am I making a mistake? Am I doing the things that he’s talking about his book?”

Okay. Let me introduce Jerry Colonna. Jerry Colonna is . . . Well, he was one of the most successful tech startup investors having co-founded Flatiron. He led investments or he did investments at CMG@Ventures. How do you pronounce that, by the way? Is it CMG@Ventures?

Jerry: CMG@Ventures, yeah. And it was Flatiron Partners.

Andrew: Flatiron Partners. Okay. I missed copied that. And then, JP Morgan Ventures, where you made other investments.

Jerry: JP Morgan Partners.

Andrew: Wow, how did I get Ventures in there?

Jerry: That’s all right. Yeah, yeah, that’s fine.

Andrew: But, please, keep interrupting me throughout the interview if I get anything wrong. I’d much rather get it right than worry about being corrected.

The thing that got me was that after doing all this, he decided that he wanted to be a coach. And I remember when I first heard that he wanted to be a coach, I said, “What is this guy doing? He’s going to be one of the richest, but more than that, one of the most respected, admired people in the space, and he’s giving it up to be a coach, which it feels like every 21 year old who grew up listening to Tony Robbins was aspiring to do.”

And then, I started to hear the people whose lives he changed. Entrepreneurs who would often come to my office saying that they’d been broken, and he actually helped them get back on track. And I said, “Wow. Now I kind of envy what he’s able to do. Why don’t I have that kind of meaning in my life?” And frankly, he’s built up a successful career having done this.

He is one of the founders of Reboot. The website is his It’s a coaching company that believes work doesn’t have to destroy us. I’m reading this off your website, Jerry, it says, “Work can be the way we achieve our fullest selves.” I feel like it’s more than that. I feel like some of the top achievers, who’ve raised money, who feel like they’re superheroes, but at the same time worry that they’re going to break and let everyone down and lose it all, they come to you and somehow you help them find their stability. Am I right about that?

Jerry: Well, that’s quite an introduction. I just want to say thank you for that.

Andrew: You know what? I didn’t even say anything about the book. I should say, the book is called “Reboot: Leadership and the Art of Growing Up.” I read it. I love it. And this interview is sponsored by HostGator and Toptal.

You know what? Why don’t we just go back and set this up better? I said that you are one of the top investors. What was the biggest success story that you had? Was it GeoCities?

Jerry: Let me respond first to something that you said at the very top, and then I’ll answer that question. You asked the question, “Was I doing the thing that he says I shouldn’t be doing in the book by getting only four hours sleep?” And I want to give you a little relief on that.

Andrew: Okay.

Jerry: In Buddhism we live by principles known as the four noble truths. And the most important in many ways is the fourth noble truth, which is the eightfold path. And the eightfold path consists of a number of items. But one of which is right intention. And what I hear is that you set the intention, you are driving yourself and you are at a point where you are physically depleted, because you put your life at the top of the priority heap. That feels like right in. So I want to give you a little relief. You’re exhausted. You’re tired. That’s fine.

You asked about my top performing investment. Yeah, I would say that when I was an active venture capitalist, the return on investment from GeoCities was probably the highest performing one.

But, you know, it’s now 20 years old. I don’t necessarily look at any one investment as the pinnacle of it, but I do look at the experience that Fred Wilson and I had in creating Flatiron Partners as a highlight of my life, as a high point in my life. Of course, it had this challenge aspects of it, but yeah, yeah. The short answer to your question is, yes, yes.

Andrew: I’m in New York City right now. I remember growing up in this city, and it was really important to be successful at anything, but ideally at making money. You hit that high. You say that you aspired to be like Bill Gates, and still, before this interview started, you said, “Soon after I wanted to commit suicide.” Can you tell me about that period? What was it like and then let’s understand . . .

Jerry: Sure, sure. Yeah, and what you’re referencing in a sense is, actually, in some ways, the first question that you were holding, and I think, even a first question that we’ve done in past conversations, which is, “How could someone who is externally perceived as at the pinnacle of success, step away from everything, why would someone do that?” And in the book I tell the story of being 38 years old, and really having to confront the fact that success, whatever the [inaudible 00:06:28] have, whatever the external affirmation that, a), did not feel like it was enough. And b), because it was not enough, I still felt an hollow inside, and was to the point where the depression was so intense, that old feelings of suicidal ideation came back. And this was at age 38, and so it was no joke because I had attempted when I was 18. So my lifelong relationship with depression and these feelings had been there.

And, you know, as anybody who has struggled with these kinds of feelings knows, there’s the feeling and then there’s the feelings you have about having the feelings, right? It’s terrifying to feel those feelings. It’s debilitating to feel those feelings. I had both feelings going on at the same time. And to be clear . . .

Andrew: Just so I understand it, it’s the feeling of, “I am not doing well. I’m not happy here. I want to kill myself,” and it’s, “What’s wrong with me that I want to kill myself? What’s wrong with me that I can’t stop feeling [inaudible 00:07:47]?”

Jerry: That’s right. Yeah. Yeah.

Andrew: Those are the two sets of feelings.

Jerry: Yeah, and yeah. And you know, folks like to focus on the suicide ideation. The more universal feeling is, “I feel like crap. What’s wrong with me that I feel like crap?”

Andrew: Right. So here’s the point that I wanted to ask you. I’m sorry to interrupt, but we’ve got a bad connection, that’s why it feels like we’re going to step on each other.

Why wasn’t the answer, instead of . . . What was it? Compassionate loving? I forget what the phrase was that you used in the book. Instead of that, why wasn’t the answer to just stop thinking about it, work even harder. If you’re feeling like you don’t have enough success, enough money, that you’re not doing enough, why wasn’t the answer to just work three times as hard, to sleep less, to work harder, to network more? Why isn’t that the answer?

Jerry: Because it doesn’t work.

Andrew: Why not?

Jerry: Because white knuckling and gripping the handlebars even more tightly, doesn’t chase away the feelings. And I see this in my [inaudible 00:08:59] as a coach all the time. The feeling of just doubled down on a strategy that’s not working, a lot of sense, it doesn’t make sense in your business and it doesn’t make sense in your personal life.

But we do it all the time. Your question is a really important question. And because it is the natural human instinct, is to simply double down on what it is that we’re trying to do. It just doesn’t work. It may work short term in short burst for some people. But generally speaking, I would say it doesn’t work.

Andrew: Because at some point you run out of hours in the day, you run out of things that you could do, and you’re not thinking clearly enough to do them well.

Jerry: That’s right. And I would say, at some point your body says, “Enough.” And oftentimes that’s at midlife, dude. Right? I often liken it, I mean, there’s another section in the book where I talk about these migraines that came upon prior to those feelings.

Andrew: Right after you started Flatiron Partners.

Jerry: Right after Fred and I started Flatiron. And I often liken it as if it was like my soul reached up, grabbed me by the neck, by the throat and said, “Stand still, motherfucker, sit still. This is not working.”

And the truth is, what I see is, whether it’s we have a semantic expression of it like that or we see people sort of diving more deeply into things like drugs and alcohol, or we see people relentlessly pursuing business. Not only does it not work for the individual, but it doesn’t work for those who love us, namely our children.

Andrew: Okay. Let me take this back, because you had that migraine. You had to go to the hospital. I think you were in and out of consciousness at that period because of it. It’s because you were trying to do, what? What was it that got you there? And then I don’t understand what helped you undo it, because at Flatiron, that’s where you had your biggest successes. So I want to know what was going on in your head that got you to have that breakdown, and then what did you do that allowed you to go beyond it, to be more successful.

Jerry: Yeah. And in the book I tell the story that the real breakthrough in coming to understand the migrants, and understand I had migraines going back to when I was a child, coming to understand that there was a breakthrough question that my then therapist asked me, which was in response to the migrants, and she asked me, “What are you not saying that needs to be said?”

And later I ended up adding two additional questions to that. “What am I saying that’s not being heard, and what’s being said to me that I’m not hearing?” And I laughingly call those “the three magic ninja questions.” Because those three questions, for me, defined so much of the root of my anxiety, my depression and the somatic expression of those being the migraines.

Because the truth is, Andrew, I was not talking about the things that needed to be talked about in my life.

Andrew: For example?

Jerry: The emptiness of chasing after lemon drops, the fact that I had enough, but I didn’t feel like I had enough. I had this approbation, and I still felt like crap about myself.

Andrew: The lemon drops are, what?

Jerry: Okay. So, I tell the story of being a boy. When I was a boy, I grew up with a significant amount of chaos and poverty in my childhood. And the good news from that was that it has shaped everything about me. It has made me the strong good man that I am, the healthy, strong good man that I am. But one of the consequences of that was that I developed this really interesting relationship with money. And my grandparents’ house, Dominic and Nicoletta [Guido’s 00:13:31] house, was this bastion of calm in a very, very chaotic childhood. And it smelled wonderfully of roses and ground coffee and lemon drops.

And my grandfather was so fixated on lemon drops that there was always a canister of lemon drops in their pantry. And in my young brain, I associated my grandparents with having enough. And so I associated lemon drops with having enough.

And later, as an adult, when I came to understand that I was pursuing and pursuing, what was that I was pursuing? I was pursuing the feeling of having enough. And that became symbolized by this notion of, “Do I have enough lemon drops?”

And now, when I work with clients, when I look at their organizations, when I look at the things that plague them as leaders, as entrepreneurs, what I see, oftentimes is a pursuit of lemon drops. See? If I have enough money, then I’ll be safe. And so therefore, I will twist my organization’s business purposes, I will drive my employees insane, I will drive myself to a physical death in order to feel safe, right?

The only reason I tell that story, the only reason I put myself out there, vulnerably to tell the stories of my childhood is so that I can make the linkage to the fact that, folks, look at the subroutines of your life, look at the programs of your life to understand why things are happening in your life in a particular way. So that’s what lemon drops means to me.

Andrew: So, the interesting thing to me is, most people who come to that realization about themselves say, “Okay, I’ve had enough. I’ll just live in peace and be okay.” Maybe one of the examples that you gave in your book of the entrepreneur who said, “I have an opportunity to sell my company, I’ll sell it.” I forget his name.

Jerry: Steve Kane.

Andrew: What was the name of the company, did you mention it?

Jerry: Gamesville.

Andrew: Gamesville, right, right. And so, but the for you, that wasn’t the realization you came to. You still worked to do more, even after you came to this understanding about yourself. Why didn’t you say, “All right. I think I’ve done enough. I’ll take it easy here, and . . . “?

Jerry: What you’re really asking is quite a large question. It’s a really important question, which is, why do we still struggle even when we come to understand these structures in our lives?

Andrew: Well, actually, I’m sorry to interrupt but, I worry when people talk to me the way that you are here, that I am going to lose my edge. I’m not going to want to work as hard and I’m going to accept it. Frankly, I’m doing okay. I don’t have to work as hard.

And what’s interesting is that you didn’t come to that, “I’ll just live in peace here and not work so hard and not do anything more with my life.” You actually got to a place where coming to that realization that it still led you to do your best work even afterwards, and people who’d gone to your program to [inaudible 00:16:45].

Jerry: Oh, I see which is the point you’re making.

Andrew: They kept on going, it didn’t make them weak, it didn’t make them passive. It made them more of themselves. And I’m wondering, what was it that happened to you that allowed you to [inaudible 00:16:56].

Jerry: Oh, you’re asking an even more sophisticated question. What you’re asking, let me see if I got it now, what you’re asking is, when people internalize the message that I have enough, or one of the concerns they have is that they’ll become complacent and they won’t strive anymore.

Andrew: Yes, yes.

Jerry: Right. And when I lose striving, I feel like I lose my edge. Am I hearing that right?

Andrew: Yes. But a few, it doesn’t. They don’t lose their edge, they find it.

Jerry: Oh, no, that’s right. Because there’s a really important difference. When we can understand and transform those structures that actually are fear-based, that are childhood-based, that drive the striving, when we can unpack those and sort that baggage, then what we can step into is the wonderful sacred creativity of work. See? I’m doing the best work of my life right now. But I am not depleting myself.

I just came off a 10-day business trip, and I feel more empowered, more alive, more refreshed than I did at the beginning of the trip because I know how to integrate and balance myself, because I’m not doing it merely because I’m trying to pursue lemon drops.

Andrew: So when you stop pursuing lemon drops, what was it that kept you going at Flatiron that allowed you to do . . . ?

Jerry: Oh, well, so let’s talk about the sequencing. I had already left Flatiron, I was at JP Morgan when I had the breakdown. And then what I had to do, was I had to leave the venture capital business, so that I could rediscover who I was, my core sense of purpose, my core identity, so that I can with that in mind, solidly in mind, I could then go back into the pursuit of work but do it out of love, do it out of creativity, not out of fear of not having enough.

Andrew: I would have thought that the fear of not having enough would be more powerful than the love of the work, and that if I had to pick one, I would have thought that fear would get me to do more.

Jerry: Yeah, well, that’s a mistake that a lot of folks make, and more, that’s a leadership perspective that people have. If I scare people, then they will do more. Now, Andrew, you have children, right?

Andrew: Yeah.

Jerry: Tell me how old they are. What are their names?

Andrew: Four and two, Shepard and River.

Jerry: Shepard and River. So when Shepard, who’s the older one, right?

Andrew: Yeah.

Jerry: Right. When Shepard stumbles and mispronounce as a word, and Shepard is a boy? Is that right?

Andrew: Yeah, they’re boys.

Jerry: Okay. They’re both boys. So, if Shepard mispronounced as a word, how well does he respond when you smack him in the face? You’re smiling, you’re laughing. He doesn’t.

Andrew: Right.

Jerry: But I’m trying to motivate him with fear. I don’t understand this, Jerry. Wouldn’t he learn the lesson of how to pronounce that word correctly or go through toilet training?

Andrew: I don’t know. As for me, I do remember toilet, I remember actually having accidents, and the fear of having people know that I was going to pee my pants. The embarrassment forced me to think about it so much until I could stop it.

Jerry: And what if you could be motivated by the pride of feeling like a big boy?

Andrew: You know, I do think that that’s true, that the pride of having this like understanding that this is who I am and having people recognize me for that would be . . . Maybe not for not enough peeing my pants, but for the more significant things, yes, absolutely.

Jerry: Yeah, I mean, that’s what we’re really talking about, is how do we motivate people. I understand that fear can clarify the mind. I understand that, especially if we’re leading a team of people, and we say, “Listen, if we don’t bust through this what seems like an impossible obstacle, then the company will fail.” And that could be a useful experience, especially if it’s true.

But when fear is used about untrue things, which happens all the time, the mind constantly tells itself stories that are not true in order to compel us to move forward. Well, when that happens, 10%, 20%, 50% of our brain is preoccupied. What if we unleash free the creativity if we know, “Google just finished that whole experiment understanding psychological safety,” but what if we all felt safe and desire to do great work, because it’s beautiful to work hard, because it’s fucking awesome to create magical things, not, “If I don’t have a unicorn, I am worthless.”

Andrew: I get that. And I do want that and I do feel that that’s where I do perform at my best.

All right. Let me talk about my first sponsor and then . . . I’m a little at a disadvantage because, usually, my office, if I’m looking through my notes to find that story that I can’t remember, it was about the two founders, I had their names, it’s on my iPad here, usually at my desk, you’d never know that I was looking for their names on my notes. But here, every time I look here it’s a little distracting because I know that you’re looking at my Adam’s apple, which is now obscured by the mic.

Jerry: I can’t, yeah, I can’t see it because of the mic.

Andrew: Yeah. You know that you do that. And you look at people’s Adam’s apple, I know you like to look at their eyes when you’re coaching them to get a sense of what they’re feeling that they may not be expressing with words, the Adam’s apple is to see when they’re quivering and might actually be onto something really emotional. Is that why you look at people’s Adam’s apple when you talk to them?

Jerry: Yeah, it’s less techniquey than the way you’ve just described it. But what I’m really describe when I do that is, I ask people to consider listening to more than just the words, right? And so there was a kind of breathlessness that you were holding as you were describing, as we were having a conversation about fear.

And what I was hearing into that, and this could be a story that I projected into you, it could be wrong, what I was hearing into that, was you, Andrew, the man, grappling with two truths, both of which feel real. One truth is, you know you do your best work when you’re leading from creative and loving place, and you worry, not just these other people, you worry that if you lose your edge, what’s going to happen to your safety. And that’s what I heard, I felt in that.

And so oftentimes, when we’re in relationship with people we can feel what they’re feeling. And I just use my empathy and intuition to imagine myself in that place, so that I can then feel connected to them. It’s one of the superpowers that I have.

Andrew: I think the ultimate example that I have to keep coming back to about fear versus love, as a personal motivator is, just reading your book. I like to read the book of a person who I’m going to meet, because otherwise it’s a wasted hour. We’re just creating content for bullshit’s sake. I want to read your book and ask all the questions that if I didn’t know you, I could come back and say, “Aha, here’s what I wanted to know.”

But if I would have started this morning on the airplane or last night at midnight on the airplane saying, “I’ve got to read this book or else Jerry’s going to think I’m a loser,” and there’s part of me that thought that or else the audience is going to think that I’m not prepared or else I will have been a liar for saying that I like to prepare. There are times when that came up and it was not going to be fun. It was going to be one of those things that I procrastinated on, and then I hated myself. I hated my work, and I hated you if I allowed myself to linger on that.

And I kept coming back and saying, “No, this is your opportunity to clarify something for yourself, and through that, other people are going to really get something honest in the conversation. This is your opportunity to read a book that you care about, and if you don’t care about it, then just tell me you don’t want to show up and cancel.”

And that is a little example in my life. But I have to keep coming back to those little examples, because the big ones, Jerry, harder to believe, harder to believe that without the fear, without the . . . Ah, it’s not so . . .

Jerry: Well, let’s just pause there and let’s go back to what you just said. And let me just tell you that I’m smiling deeply.

Andrew: I see it.

Jerry: And the reason I’m smiling is because you just showed up in a really profoundly important way, because you named that fear, that story that you were telling yourself, which kind of in, you know, to headline is, “Jerry and the audience are going to think I’m a loser.”

Andrew: Yeah.

Jerry: Right. So notice that feeling. How long Andrew have you carried the fear that people are going to think that you’re a loser?

Andrew: I would say, with a small change, I don’t so much . . . I’m sure that I’ve carried that since maybe I was 10 in New York and was . . . Like the way . . .

Jerry: Just stay there.

Andrew: I would also say though, it’s more . . .

Jerry: But just stay there. Let’s go back to it just for a moment. I know I’m taking over the interview, I apologize.

Andrew: Go ahead.

Jerry: But here’s the thing. That makes personally human, that makes you so universally human, that is community. To acknowledge that there’s a little voice in your head, as I call them in the book, whispery voices in the head that questions your worthiness, right? And by you, as an adult, as a man, as a good man, being able to acknowledge that that voice still has some power, but doesn’t have the power it may have had in another time in your life, to be able to come back and to say, “I’m going to do the best job I can. I’m going to take advantage of this opportunity. We’re going to have an amazing conversation however it unfolds.” You’ve created space, not only for me to show up, but you’ve created space for the people who are listening to this conversation to show up themselves. That feels great. That feels sacred.

Andrew: And I would want to get rid of that in more places. It’s true that if I could get rid of that voice, and actually replace it with this feeling of . . . Oh, that greatness that I felt when I was 13 years old walking through this city, this sense of, not only possibility but, “I am entitled to this because there’s something special about me that separates me from all these other defuses at Hillcrest camp.” I get that. That’s a harder one to get back into that feeling, and I think if I could crush that first one, I could get to the second.

Let me take a moment talk about my sponsor. I’m just going to thank them. And then I want to come back and ask you about this delusion, because I do feel like I enjoyed that delusion that I had at 13, and you’re saying, at one of your talks at your boot camp, “We’re here to exercise delusion.” I remember you saying that you even, almost like were a preacher, the type of preacher you admired, as you woke up and you talked to them about this.

All right. I’m just going to, instead of telling you guys about HostGator, I’m just going to thank HostGator for allowing me to . . . They’re not even supposed to be a sponsor today, but I knew that I’m tired, my head is not clear. Instead of worrying about what sponsor to pull out, I can just say, “This is sponsored by HostGator,” and they will pay me for doing this. And I really appreciate them doing that.

So if you want a hosting package, you can go to and find out about them and why that’s a good package.

Jerry: Can I thank them too?

Andrew: Yes, please.

Jerry: Thank you, HostGator, I really appreciate you’re helping make this happen. It means a lot.

Andrew: It really does. I appreciate that they just be okay with this and be understanding.

So let’s come back to that. You said, and I feel like that’s one of the best things that I’ve heard about your boot camps, that people can actually just be themselves and let go of the delusions, and at the same time, I feel like when I was delusional, that’s when I was at my best.

I remember talking to Sahil Lavingia recently at my office, I interviewed him. And he said that when he was starting out with Gumroad, he had this belief that he was going to be Bill Gates, that he had that power. And then when he lost it, and the business was so bad that his investor said, “Here, give us $1 and we’ll give you your shares back, we just want to be done with you.” He felt crushed, and I sense that he went to Mormonism to feel connected to God, so that he could have that superpower feeling again.

I would do anything to have that delusional 13-year-old-kid’s feeling again. How do I get that, and do you think I should get that? How do I get that without kidding myself to the point where I am distracting?

Jerry: Yeah. So, in the book, one of the things that it’s really important to understand is, you used the phrase before, “crushing that old mindset.” I don’t want you to crush that old mindset. I don’t want you to crush the drive.

Andrew: Why not? The mindset of saying to myself that, “You’re not hitting your goals, you’re not . . . ”

Jerry: You know why it was important, Andrew?

Andrew: Why?

Jerry: Because it got you out of Hillcrest camp.

Andrew: You mean that sense of grandeur got me out of Hillcrest camp?

Jerry: That’s right. Because it was a childhood survival strategy. You developed it in order to move into adulthood. It was a beautiful strategy that you developed at 10. It was incredibly sophisticated, but it’s no longer valuable. In fact, the negative side of it outweighs the positive side of it. That’s the thing about being an adult. That’s why the book’s subtitle is “Leadership and the Art of Growing Up,” because what we want to do with those past structures is thank them, is bless them so that we can then develop new structures, so that we can develop new goals.

Andrew: But I feel like if that structure helped me, shouldn’t I be tapping into that old structure?

Jerry: Yes, as long as it doesn’t get in your way.

Andrew: Yeah. Okay. So then I do want to get back into that. By the way, Jerry.

Jerry: If it doesn’t get into the way.

Andrew: I feel like you’re not mindful of promoting your book and yourself, and in my head, in this conversation, I’ll be fully open with you, I keep thinking, “No, I want to talk about those two CEOs who came to Jerry, so that we can show the audience that Jerry is important enough for them to care about the rest of this interview, because if they see that he didn’t just help himself, he also helped these two other entrepreneurs and they see his technique, than they’re going to understand his technique better, and if they care about the book and his ideas, they’ll be able to follow up, Jerry will be happy, the audience will be happy.” I think that all the time in interviews. And I feel like that’s a good thing.

I’m sensing that you’re not thinking that, that you go into, and this is where you’re really good you, you want to be the coach in this conversation, that you’ve got that magical power and you’d rather exercise that. And if people read the book because of it, great. If they don’t, great. You just want to be you in this conversation with me.

Jerry: Well, I wrote the book so that people can experience asking themselves deep questions so that they can be coached. And when I see somebody that potentially is struggling, part of my old pattern is to go at that space. I’m happy to talk about those CEOs that you’re thinking about, and I love talking about my book. I’m proud of the book. I think it’s a different book.

Andrew: You should be, it’s not . . . You said, right in the beginning, first of all, you said, right in the beginning, “I was told it doesn’t have to be a standard business book and I started to cry.” And I go, “This guy cries a lot.” If I do a search on the word weep, it’s got to be seven times in the book. And then you say, “Great, this could be the book I always wanted it to be,” and it is. You know what makes your book great? You’re a good storyteller. You just will say, “Here’s what happened in my life,” and you let me draw my own conclusion. And if I need your help, it’s clear, it’s written there. But I like that, I like specific stories, it shows the credibility that most people leave for, like the back cover or the . . . I don’t know what.

Jerry: Yeah. Well, what I’d say is, I think stories are how we learn. And you know, in the afterword, I give people an image, which is that we’re all sitting around a campfire telling stories, trying to make sense of our lives.

So you know, look, let’s pull up a level and talk about it from this perspective. What makes a great leader? Right? There are dozens and dozens of really worthy books that will give you the five things that you need to know to be a great leader. To me, one of the most important questions, one of the most essential issues is, who am I as a leader? Because if I tell you the five things, Andrew, and I’m successful, all I’m going to do is turn you into a clone of me. And you’re going to come up short.

You know it’s the entrepreneur’s dilemma. The entrepreneur thinks that they’re supposed to be Steve Jobs. And the problem is they’re not as smart as Steve Jobs, and they never will be. And so they feel like crap. And then they kick it around on their company, and they don’t access their innate creativity.

So I feel it’s a sacred mission, it’s part of my sacred duty to create the space for every individual to grow into the fullness of who they are, to grow into the fullness of their leadership.

Andrew: Can you give me an example of somebody who grew into who they were instead of into Steve Jobs or . . . ?

Jerry: Well, I’ll tell the story of Chad Dickerson, and I’d tell that story of the night before he’s announcing that he’s been fired as CEO of Etsy. And I make the observation that in that moment, I saw him and all his fullness as a CEO, because he carried himself with grace and dignity, even into the last days in that position. And the result, and if you jump forward in the end of the book, the result was that he’s a better, happier man, because he enabled himself to be a full-blown human.

He didn’t get up there to announce in front of the team, “Oh, I’m taking time off to be with family.” Some bullshit euphemism. He said, “I was fired.” And my good friend, Fred Wilson, stood up in front of the same team and didn’t say, “Blah, blah, blah, bullshit, bullshit, bullshit.” He stood up there and said, “And if you have a problem with that, it was my decision. Take it out on me.” That’s courage. That’s warriorship. That’s leadership.

Andrew: Okay. I’m going to challenge again because I want to understand. Two days ago, maybe it was three at this point, I was running a marathon in Santiago, Chile. Mile 17 or 20, I don’t remember what it was, but I recorded it into my phone. I wasn’t happy. I was just miserable. It was very hot, harder than I expected and they ran out of water, which, “Come on, as an organizer, don’t run out of water.”

Jerry: It’s dangerous.

Andrew: Yeah. They had Gatorade because they were a sponsor, not water. And I needed water, Gatorade just tasted too salty for some reason at the time. And even though I was not happy, I just kept on going because it was important to me not to be happy but to be complete, to get to the end, to finish, to hit that milestone.

And I feel like we are prioritizing happiness over, I’m going to say it, over money, over accomplishment. I don’t know that . . . I admire what he did, what Chad Dickerson did building that company more than the ending. And if at the end of that story, you would’ve said, “Because he was happier, he was able to create this other company.” I feel like I would be more receptive to it. I feel it [inaudible 00:37:25].

Jerry: First of all, on Chad, he’s not done. Second, I hear you. Okay? And I am not demeaning the pursuit of good work. Good work is really important. Good work, it’s sacred, it’s divine. You striving to finish that marathon, is enormously life affirming. You pushing through that moment, is enormously powerful.

The question I would ask you to consider is, if you push through, why would you not? Think back to the book and think of the story I tell about my friend and former client, Ben Saunders, the polar explorer, who successfully skied from the edge of Antarctica to the South Pole and back across four months. He and one other mate. No one has ever done that in the history of humanity.

Later on, several years later, he’s trying to do something similar, solo skiing across Antarctica, from one side to another. And he gives up at the South Pole, because it was just too hard.

Later he said, “It’s better to be a live donkey than a dead lion.” Okay? Now, what I love about both sides of the story is, he pushed himself. Trust me, he pushed himself for months on the ice, three changes of underwear. That was hard.

Andrew: Yeah.

Jerry: But in the second story, it was not worth losing his life for. And that’s really the issue, sometimes, because of our old subroutine programs, we lose sight of what’s most important. And this is not my book, my talks, my work, is not an exhortation to not work hard, quite the opposite. Go out and build magnificent structures. Go change the fucking world, just don’t die doing it.

Andrew: And do it for the right reasons, not to pretend or the ones that you’ve taken on from your childhood.

Jerry: That’s right. David Whyte, the poet, whom I admire so much, has a wonderful phrase, which we’ve turned into a mantra for the business, “Good work done well for the right reasons.” And my challenge is, the challenge I see is that, too many people don’t understand the reasons by which things are happening in their life. They just sort of, almost like automatons, work hard, work hard, work hard, work hard. Work hard, know why you’re working. Pursue money, go to it. Money is great, but it doesn’t close the hole in your chest that says you’re not worth anything.

Andrew: So then, what does close the hole in our chest?

Jerry: Love. It’s the only one thing.

Andrew: And you’re saying, if I close the hole in my chest, I’ll still have the energy . . . In fact, you’re saying, you’ll have more energy and more satisfaction if you do it.

Jerry: Because you will create great works. Here’s the thing, I’ve created, in this book, the thing I’m more proud of than anything I’ve ever done. I don’t know if it’s going to have any financial return. I don’t know. From my lips to God’s ears, yes. Because many people took a bet on me. But I can lay my head down on the pillow at night and say, “Good work, done well, for the right reasons.” And there’s . . .

Andrew: [inaudible 00:41:14] with the book with Reboot?

Jerry: That’s a great question. So that people can be free to do their best work of their lives. I don’t want people to not work. I want people to find the joy in work, in hard work.

Andrew: That’s why I’m coming to you with my challenges. So, you know what it is? I want you as the voice in my head really badly, because I do notice that you’re someone who’s saying, “Andrew, there’s good in you but it’s not going to make you weak. I don’t want you to sit under a tree and meditate all day.” And I’ve seen the results that you’ve gotten for people.

Jerry: So just pause on that. See, see? You’re asking me to coach you. So here’s the thing. You ask what’s the reason for the book, I want to be the voice in your head. You know want my image is? This is my image. And this has started happening, number of people that have the uncorrected galleys, the book that I sent you, right. I’ve gotten two or three folks who’ve texted me a picture of their copy of the book, and it’s got sticky notes in it and it’s got page turns and they’ve written in it. And my image is five years from now, somebody turns to somebody else who’s struggling and it says, “Here’s my copy. It’s torn up, it’s beaten up, it’s been engaged with, it’s been consumed, it’s been engulfed. Here, this might help you.” That’s my image.

Andrew: So there is a part in the book that I was bringing up . . . But you know? Let me take a moment, I’m going to say, if you guys are out there looking to hire . . . My second sponsor is Toptal. Go to They’ve got a phenomenal program where as soon as you go to that page, you hit a button, you’re going to get on a call with a matcher, they’ll understand your needs, and if it’s a good fit, they’ll help you hire a developer. You can often get them to get started with them within a day or two. If it’s not a good fit, they’ll frankly tell you it’s not a good fit and you’ll be upset with them for not taking your money and you’ll email me. But I’m still happy to tell you that, go to,

Okay, so here’s the story in the book that I mentioned earlier. Two co-founders, they sit in front of you and they say, “We bicker all the time,” and sure enough, they bicker in front of you all the time. You get to a point where, as calm and as full as with equanimity as you are, you say, “Shut up already,” or some version of that.

Jerry: I think I said, “Shut the fuck up.”

Andrew: Oh, all right. And I thought maybe I was going harsher, it turns out I wasn’t harsh enough. And then you say, “Why do you argue . . . ?” And I forget what the magical question that you asked was, but you asked the magical question. And one of the co-founders says to you, she says, “I feel like I argue all the time because I have to be right,” and you ask, “Where does that come from?” And she says, “It comes from, in my family, if you weren’t right, my dad would . . . ” I forget what it was, I think it was a word like wallop, and I don’t know if she meant literally hit her on my.

Jerry: Annihilate.

Andrew: Yeah. Annihilate. And so, she needs to always be right and that realization helped her become a better communicator with her co-founder. What I wonder is, now that I know that, will I be able to find that shut-the-fuck-up-Andrew moment, will the reader who comes to Reboot, the book, be able to recognize these moments.

And by the way, the book is great at that, you had this freaking phenomenal podcast with Derek Flanzraich, the founder of Greatest, where he was not looking at his finances and you helped him, in that call that you recorded and turned into a podcast, understand how that ties back into his parents and how that helps them get to a point where he realizes . . . I think to his dad, where he realizes he has to look at the books, even if it’s painful to look at the books. He had to acknowledge himself that the books weren’t as great as this greatest guy in the world is portraying. Well, he wasn’t, but you know, he had to get himself to a point where he could get that. Can a book get someone to the realization that Derek got? Can a book get someone to realization that his co-founder got?

Jerry: Well, you asked a lot of questions in there. So I’ll go in reverse order. The answer is, yes. I think so. I know that books have been asteroids in my life and changed the course and trajectory of my life. And one of the reasons why every chapter of the book ends with a set of questions, or designed to prompt people to consider what I’ve just written, but consider its effect on their own life. So I think that the answer is, yes, that can happen. But so can a podcast, so can a random conversation with a stranger, so can many things get people to sort of pause and unpack things.

To go back to the one instance that you’re talking about, the story of the two co-founders fighting, yeah, the realization that that woman always needed to be right . . . To take a step back, the propensity that she had as part of her leadership to always be right, mirrored the way her father annihilated everybody at the dinner table. Meaning, everybody in her leadership team felt wiped out by her need to always be right. Especially, because 90% of the time she was right. Great. So fantastic. You’re right. Now you’ve built an unscalable leadership team because you’re the only one who’s right. Totally undermining the very essence of what it is that a CEO is supposed to do, which is to build a scalable leadership team. That’s the number one job.

By unpacking that, and seeing the roots of that, she got to be able to pause and ask herself the question, “That served me well as a child because I could stand up to the bullying of my father. But now, I myself have become a bully. And I don’t need to be a bully to surround myself with really great leaders.” Right? And that critical juncture is really important.

Now, to be clear, just because we unpack that and see it clearly, it doesn’t mean it changes overnight. In fact, cognitive awareness alone, doesn’t create transformation. Cognitive awareness creates the conditions by which transformation can happen. Transformation happens with work.

Andrew: It’s not going to be a aha moment and then that’s it.

Jerry: No.

Andrew: And what she had to do, if I remember right, was pay attention to when she was arguing and work on that?

Jerry: Right, and ask herself the core question like, “Is it really necessary that I need to be right in this moment? What’s in service to the organization?” It may be in service to her to make her number two employee feel wrong. But it doesn’t necessarily serve the business. Great. You feel great for five minutes. And then you’ve got a problematic set of employees.

Andrew: You were talking earlier about sitting around the fire. I think you mean literally, right? At the boot camp.

Jerry: So, yeah, we do do some work around fires at boot camp. Yeah, that is true. You have heard right.

Andrew: One of the questions I’ve had was, actually, the feeling that I had until I read this book was, these programs are not for me. Even when I heard about your book, it was from someone who gone to one, and he’s an investor and I get why it would be for him. He’s is in India. He’s investing in companies. I get it. The people who come to you are the people who, I imagine, like Brad Feld, the investor and others send to you. I feel like, do you have to raise a bunch of money to be okay to be part of this or . . . ? Actually, I’ve always felt that that’s absolutely the truth. It’s for people who raises a bunch of money.

Jerry: Okay. So I’m sorry, you keep presenting the opportunities to coach you. So, how does it serve you to see that doing this kind of work isn’t for you?

Andrew: Oh, it doesn’t. It was his unconscious belief that I didn’t realize until I . . . I don’t know what it . . .

Jerry: Yeah, yeah. So, how might it have served you in the old days?

Andrew: Oh, I see. Okay. You’re saying, “To believe that this is not for me.” Oh, it would have kept me from being vulnerable around people who I cannot . . .

Jerry: And how might that have made you safe?

Andrew: Maybe they would have thought that I was stronger and more successful than I was, because apparently everyone around the campfire talks about how they’re not what people think they are.

Jerry: Right. And so, think about that brilliant but flawed logic of a five-year old. See, I should not avail myself of any relief that might come of an imposter syndrome that I might have or belief system that I might have, because doing so would make me vulnerable and perhaps challenge people’s perceptions of me. So I’m going to maintain that structure by telling myself, “That’s not for me.”

Andrew: So how do I even recognize that I have that structure so that I can figure out why it’s there and then remove it?

Jerry: Well, let’s point out what happened. You saw it after reading the book.

Andrew: Right, right. Okay. I see. And you know what it was about the book that helped me see that? It was . . .

Jerry: What?

Andrew: It was examples from other people. It’s so hard for me to think, “That woman is such a fool for yelling at people.” And then when I say, “That woman is such a fool,” I think about how Devon and I, who traveled to Santiago, I got into an argument with him, it wasn’t like this big heated up thing, and I recognized it was something in me that’s causing it. It’s not necessarily what happened to her. But it’s easier for me to point fingers at her and go, “Ah, I’m kind of similar.”

Jerry: Mazal tov. This is what we do when we sit in community with each other. This is really what you’re doing with your interviews, Andrew. It’s you’re helping other entrepreneurs by them listening to the entrepreneurs’ stories. That’s what we do.

Andrew: I do aspire to do that. I do aspire to do that, to have them talk about themselves in a way that then other people can say, “Hey, that actually is similar to me. I been also . . . ”

Jerry: Right. And so you just felt viscerally the power of sitting around the campfire, if you will, and telling true stories, and telling stories that are more than true, that are deep and revealing. So that we are sitting in community, and not only I’ll warrant to guess, because this is a feeling that many folks who come to our retreats experience. “Wait, wait, wait, you mean I’m not alone in my craziness? Wait, oh. And if I’m not alone then I must not be uniquely broken.” And there’s a whole relief that comes from that.

Now, let’s drop the mic and go back to leaders for a moment. Imagine that the leader is carrying all of this belief system. “I better not tell that I’m struggling, because if I tell them that I’m struggling, then they’re going to think I’m weak. And if they think I’m weak, then they’re going to leave me.” Right? That’s part of the whole mantra.

“Wait, so what you’re saying, Jerry, is if I experience this person’s story, and I feel a relief, then imagine if my employees see someone who has power be real and true, then all of a sudden what starts to happen is they start to feel relief and then what gets released is creative power.” So instead of all this all walking around bullshitting and pretending, we get to step into the best work of our lives.

Andrew: The example that comes to mind, and again, if I could cheat totally, if I was at my desk, it was the story of the one entrepreneur who came to you and said, “We don’t have enough money and I can’t tell . . . ” And you told him, I think that, “Why aren’t you telling people?” And he said, “If I tell people, they’re all going to leave.” And he came to the decision that he was just going to tell people on his team. And not only did they not leave, but they took a pay cut.

Jerry: Took a pay cut.

Andrew: And as a result, the company did better. I wonder, I know that story is one that’s going to stick with me for a long time, and frankly, it’s going to stick with me because of who he is and because of his connection to you. I wonder, what would have happened if they would’ve left, if they would have like on the sly look for other jobs?

Jerry: Well, as I often say, “Would you rather have them stay for a lie?”

Andrew: Yes, because I think that maybe, if they’re staying for a lie, we can all create this lie together and make it real.

Jerry: And I would say that that’s a . . .

Andrew: Jerry, I don’t mean that, I wonder about it.

Jerry: Well, there’s a cost to lying. And the cost is personal.

Andrew: [Tells us more 00:54:22] about that.

Jerry: Yeah. Because what happens when we consistently fib and avoid the truth, it’s kind of like Derek in that first podcast, in that podcast that you were referencing, we can participate in a collective delusion and pretend that the numbers are fine when in fact the numbers are not fine, and from my seat, I’ve sat on 120 boards of directors, okay? I can tell you that the companies that do best face their challenges with [fearlessness 00:54:57], with directness and with clarity. That doesn’t mean they all survive. Okay? This is not about survival. This is about, if you’re going to give yourself a fighting chance, you must be strong and brave. Right?

Yes, you’re smiling because here’s the thing, the perception is that the things that I speak about are soft, and I say, “That’s bullshit,” because it’s much braver and harder to stand up in front of a team and say, “We’re out of cash in three weeks,” than it is to pretend and be sleepless for three weeks.

Andrew: That’s true. And I do then, it falls back to my belief that the brave do better, and that I’d want to be brave.

Jerry: Right. So being brave is a function of facing the fear, it’s not being without fear.

Andrew: I smile because at that point when you said that, that’s when your voice got in my head.

Jerry: Good.

Andrew: You mentioned a conversation that you had, in your book, with Seth Godin, and I thought, “Hey, it’s kind of cool that he know Seth Godin.” And then I realized you invested in Seth Godin before he was this big guru.

Jerry: Before he was Seth.

Andrew: Before he was Seth. He got in my head years ago because I had the same kind of conversation with him and he appreciated that I was challenging him on his book “Tribes,” and the way he got in my head was, I said, “You want me to have a tribe of people. There’s nobody watching this freaking thing. You’re the only one who’s watching this interview right now, Seth, because you’re the first person to do it via video.”

And he told me the story about how Barack Obama was in a car with nobody, except the photographer, who was trying to trail this guy who was trying to be president. And he just kept talking about what he believed in until people gravitated towards him, until he had this big arena full of people, some of whom were fainting because they were listening to him. And that voice was in my head throughout, as nobody was watching I said, “Yes, but just speak about what you care about and then the right people will show up, and if they don’t, to the last level, at least you’ve spoken about what you care about and that’s a better way to go.”

All right. You’ve done that with this book. I love this book. As a reader, as someone who, I really could have just BS my way through, with any one of the author interviews, authors are great where they will like, “Go on,” because they’ve spent so much time about their books. All you have to say is, “Why did you write the book? Who is it for?” Right?

I don’t want that. I want to really understand and I want to get in the book. And the book was so good because, as I said, it’s just like this collection of stories. It’s easy to get lost in a collection of stories.

What you don’t, I feel like I do enough in this interview is, and I hope that we’ve communicated is, you don’t talk enough about your success that I worry in my head, and maybe I shouldn’t, will the audience take this guy seriously? In this world, in America, in entrepreneurship, we take people seriously when they’ve achieved a lot. I almost want you to be in that same backdrop that you were in the first interview that you did with me where it was like this beautiful room, like very spacious and I think it was even in New York.

Jerry: Oh, that was my apartment in New York. This is my basement office in my house, in Boulder. It’s lovely. It’s snowing. It was 82 degrees yesterday.

Andrew: Yeah. And you don’t feel the need to boast, which actually is it makes me feel good because I hate boasting, I hate like posting stuff online. I’m more interested in other people. And I feel like in this world of Instagram and talk up your successes that maybe I’m not being doing right by my work, but it helps to see that you’re the way you are.

Jerry: Wow, thank you. It helps me to be the way I am, which is . . . Most days I [feel good 00:58:37] about myself, and you know, material success . . .

Andrew: You don’t feel good about yourself. I feel like you’ve done the work, both business and emotional, how do you still not always feel good about yourself?

Jerry: Human. And I have subroutines and I love the subroutines.

Andrew: What’s a subroutine that makes you not feel good about yourself?

Jerry: Will I have enough, still an old subroutine.

Andrew: Still? Even after going through the work for yourself, helping other people, it’s still, “Will I have enough?” Enough for, what? For me it’s enough to stand up in New York City.

Jerry: To be safe.

Andrew: Safe from the childhood you had?

Jerry: Yeah. From the poverty.

Andrew: From poverty. And inflicting it on yourself or inflicting it on your family?

Jerry: Oh, on myself right now. I feel really proud of the fact that I have created a really, really healthy container for my children. That’s super important for me.

Andrew: What do you mean by “container?”

Jerry: They are moving into adulthood with grace and fierceness. They are strong, capable people who know how to be in relationship with their own fears, with their own woundedness, just like . . . they’re becoming the adults that they were born to be. Which is really what our work is to do.

You know, the closing chapter of the book speaks to this process of becoming an adult. And one of the purposeful reasons behind the subtitle “The Art of Growing Up” is that it is an art. It’s not a science. It’s not a moment in which one day you’re not and one day you are. It’s a process of coming into relationship with yourself. And to be an adult leader, is a wonderful lifelong practice. Just like being kind is a lifelong practice. Being true is a lifelong practice.

And there are going to be moments when you’re not true. And there are moments when you’re unkind. And there are moments when you struggle. And being okay with yourself during those moments, I think is the greatest opportunity in the journey of becoming a leader. Because then you can create organizations where to do that for other people. And I stepped on your line.

Andrew: No. I had so many more things I wanted to ask, but I’ve learned when it gets to the heart of the conversation, “Andrew, let it go for a little bit. Sit with what you just heard. Don’t go for the next item on your mental list.”

I’m going to say to people, if they’re interested in reading the book, it is called “Reboot.” We will be publishing this interview, I think the week that the book is out or somewhere around there. Frankly, go just get it preordered if you can, get it if you if it’s available by the time you hear it. I think it’s great. I just think it’s a great book. I want to hear more from you.

Jerry, Dan Putt introduced me to you a long time ago. It took a while for me to hear your stuff from lots of different angles until it got into my head. I think there’s somebody right now who goes, “I listened to the whole thing. It’s kind of interesting. I’m never going to get the book.” But I think that we’ve just kind of introduced it, the way that, when I heard you with . . . Maybe it was Jason Calacanis, it was just another little drop. When I heard you somewhere else, it was another, a blog post, a conversation with someone. It’s another little drop and then I realized, “Okay, I get this direction.” And I hope that we’ve done that for people.

And for those who want to get a lot of drops, the book is called “Reboot.” You can find it everywhere, of course. And the website, if you’re interested in coaching, in the events, in . . . What is it all [inaudible 01:02:35] that you have?

Jerry: All things reboot.

Andrew: All things reboot. If you want to actually experience it, go to And finally, I want to thank the two sponsors who made this interview happen because I know that they’re going to cover anything if it’s a last minute interview. I want to thank them for doing that, and Thanks, Jerry. Bye, everyone.

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