This Week in Startups - Jerry Colonna on 'Reunion': sustaining founder drive, enlightened leadership, and more! | E1864

Episode Date: December 13, 2023

This Week in Startups is brought to you by… Corient. Real wealth requires real solutions. Corient provides wealth management services centered around you. For more information, speak with an advisor today at Corient.com Lemon.io - Hire pre-vetted remote developers, get 15% off your first 4 weeks of developer time at https://Lemon.io/twist Coda. A new doc that brings words, tables and teams together. All your valuable data, plans, objectives, and strategies in one place. Go to https://coda.io/twist to get a $1,000 credit! * Today’s show: Jerry Colonna joins Jason in person for a philosophical dialogue about the search for meaning as an entrepreneur, drawing on their multi-decade friendship. They explore Jerry's personal journey from venture capitalist to founder coach (11:08), the challenges leaders face as startups evolve (40:03), how Jerry helps entrepreneurs transition from founder to CEO (28:54), and much more! Timestamps: (0:00) Jerry Colonna joins Jason (1:14) Jason's early internet days and first taste of money/power (10:08) Corient - Speak with one of Corient's wealth management advisors today at http://corient.com (11:08) Jerry's journey as a venture capitalist during the peak Dot-com era to founder coach (18:32) What pushed Jerry to his limits, and how did Jerry overcome his depression (23:36) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist (24:56) Jerry's Book "Reboot" and what Jerry sees drives founders (28:54) How to transition from a founder to a CEO (38:31) Coda - Get started for free at https://coda.io/twist (40:03) Finding the right motivation and the steps to being an enlightened leader (57:01) Acute issues that founders contact Jerry about * Check out Reboot: https://www.reboot.io/reboot-leadership-and-the-art-of-growing-up/ Check out reunion: https://www.reboot.io/reunion-leadership-and-the-longing-to-belong/ * Follow Jerry X: https://twitter.com/jerrycolonna LinkedIn: https://www.linkedin.com/in/jerry-colonna-reboot * Follow Jason: X: https://twitter.com/jason Instagram: https://www.instagram.com/jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis * Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland * Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow TWiST: Substack: https://twistartups.substack.com Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin * Subscribe to the Founder University Podcast: https://www.founder.university/podcast

Very broadly speaking, there's a whole set of other issues when you don't successfully raise money or when you don't find product market fit or it should never happen to you, you run out of cash. It's a whole different experience. What Jason just laid out is the pain that can come with succeeding. This Weekend Startups is brought to you by Coriant. Real wealth requires real solutions. Corrient provides wealth management services centered around you. For more information, speak with an advisor today at coriant.com, lemon.io. Need to speed up your product development without draining your budget?

Hire vetted engineers from Europe at lemon.io. Go to lemon.io slash twist to get 15% off for the first four weeks. And Coda is the all-in-one doc for teams. And they just introduced an AI-powered assistant to take the busy out of the work. Get started for free at coda.io slash twist. All right, everybody, welcome to another episode of this week in startups.

Jerry Colon is here. This is his third appearance. I thought it was the fourth. But we did a double episode when you're talking about reboot because you and I go back. But yeah, you've been on in 2013. Oh, no, wait, you were in June, 2013, then again in September 2013, and then in 2019.

So you've been on a couple times. Jerry's one of my oldest friends in the industry, one of my oldest friends. I met Jerry in 1994-ish, 93 maybe. The internet was just emerging. Jerry was working at a company called Like Us about a decade before. I was an investor in it. Oh, you were an investor in it. And it was helping Lycos and then 0.5,

which was the 0.5% of the web, right? They had that two. Point communications, yep. Point communications. And so there were only maybe 20 or 30 people in New York working in the internet. And so somebody said, you got to meet Jerry. I said, okay, I got to be Jerry. And I came to his office and we became friends.

He went on to do flat iron partners with Fred Wilson. And then something happened in his career and he decided, to be thoughtful and try to help founders. To stop being an investor. Without putting money in their companies. So I think it's a good place to start. You were a rabbit capitalist in the dot-com era, placing bats working 70, 80 hours a week,

and you burn the candle on both ends and you went as hard and fast as you could, and then something changed. And eventually then you became a coach and an author now, and you've got the coaching company with a couple dozen people in it. You work with, I don't know

how many dozens of founders, but tell us your journey from a venture capitalist peak.com era and then winding up as a coach of founders. So I'm going to disrupt this.

Yeah, do whatever you want. Okay, that's what I thought. Yeah. So the real story is, okay, he was homeless and penniless. Not too far. Far from the truth. In fact.

And he was, he was hock in this magazine that he had started. Yeah. Cyber Surfer. My first magazine. Cybers. Right. That's how like unhip he was. And the time cyber was sort of hip.

Sort of. I don't know. Maybe. Just show up in people's offices and put a stack on there and then like run out. It's like, what is this magazine? So. True stories. Right.

And I think I gave you your first job. Yeah. So I said, hey, you know, I want to do stuff. And he said, okay, will you read business plans? So back in the day, people wrote business plans. And he gave me two business plans. One of them was for Beverly Hills Internet. Yep.

And the other one was for the Spot. Beverly Hills Internet became GeoCities. The Spot was a online soap opera drama on the web. And I wrote some coverage of that because I was a writer for Fred and Jerry. And I would come by their office every two weeks, and they would buy me sushi or pay me a thousand bucks and just gave me some work. And then Silicon Out Reporter magazine came out. And Fred said, listen, the Silicon and I reporter. And Fred is Fred Wilson, by the way.

Fred Wilson said, listen, this thing's going to get very big, the magazine. And working for us, it's going to be like a small opportunity for you. I think you should do the magazine. It's kind of hard to be a venture capitalist and then write about the companies. So which one do you think you want to do? And I said, I'll do the magazine. He said, great. Hire my wife.

The ad sales person. And I said, oh, okay. What are you talking about your? She's at home with our kids. I said, okay. So I called Joanne Wilson. And the kids are screaming in the back. She said, hold on a second.

Get off that. You're going to kill yourself. Okay. So tell me about the magazine. And I said, well, tell me about you. And she said, I worked in the schmatsu business. I said, I'm sorry. God bless you, what?

And she said, no, no, schmats of business. I was selling like clothes. What does it have to do with the technology magazine? Nothing. I can sell anything. And I said, okay. And she wound up working with me as my partner on it, sold ads like a banshee. It was just the greatest salesperson I ever met and just one of the great people.

And, okay, so you see, isn't this a better way to open than just what he was asking me about? Yeah, okay. We'll get to that story. We'll get to all that. Okay. So, and the greatest deal of the century that Fred Wilson and I ever negotiated, our venture capital firm was called Flatiron Partners. The greatest deal of the century that we ever negotiated. was a permanent centerfold two-page ad in every copy of Silicon Alley.

It was, yeah, you guys were one of the first two advertisers along with the company called Razorfish. And I don't think we paid you. No, you did. You paid. Yeah. Yeah, but it wasn't very much. It was $250 an episode. I had said to my, per issue, I said to myself, I can get four advertisers for $250,

I could print a thousand copies of this because the guy told me it'd be a dollar per copy. Right. because it was a photocopy. Just, we called it a magazine, but it was a photocopy. And the village printer up on 43rd Street in Manhattan printed it, but it was eight pages. So it was like 12 cents or whatever. So it's at eight times 12.

It's like a buck. So a buck per episode per issue. I get four advertisers. I break even. I'm good. So then I go to pick up the first thousand copies at like midnight one night. I was so excited. And the guy says, okay, $2,100 bucks.

I said, what? He said, yeah. I said, but you said it's eight cents a page or whatever. He says, yeah, eight pages and it's double-sided. It's 16 pages. I don't have that kind of money. He goes, okay. I said, what are we going to do here?

He's like, well, I'm going to put the magazines over here, and then you come back with another thousand and I give them to you. I said, let me tell you, I'm going to get from Brooklyn. I'm trying to make this magazine. I got a credit card. There's no way $2,000 going to work. Can we charge like $1,500 and see if work? He goes, I'll just charge $1,000.

Don't worry about it, kid. and that's when I realized if you ask people for a favor they'll do it but I told them the story I said listen I'm just a kid from Brooklyn I'm trying to make a magazine this is the first episode

my cars can't hold this and so my first two investors I would joke with people were American Express and Visa and I said you know the difference between these two investors was Visa you know was very patient

and American Express wanted their money back the next month they were not patient capital and I took the magazine to Roseland because there was an internet party happening there. In New York, the internet parties were like a party party.

So I got there and I had a, I used to carry a luggage cart. Yeah. With like two or three hundred episodes. I'm walking down. Issues. And I get there and I go in and I was like, what's with that?

I'm like, it's my new magazine. He's like, what's it about? And I said the internet. He goes, oh, I got the internet too. Can I have one? And I gave it to the guy, the bouncer, go in.

And I start showing it to people. And all of a sudden, the entire party of 300 people coalesce on me with the magazine. They hand it out. And then everybody goes out and I look around and everybody was looking at my magazine. Yeah. Wow. Media is power.

I've never had any power. I'm going to be powerful and rich at some point. Because I had never had any power. and I had never had any money and all the problems I had in my life growing up in Brooklyn we both grew up in Brooklyn he was in Bensonhurst

I was in Bay Ridge next to each other Tiger Heights in the middle we were the tougher part of the Brooklyn it was all tough but yes that's not I mean Bensonhurst was the mafia

um Bay Ridge was the cops and the firefighters I don't have a problem but they all hung out of my dad's bar they were great tippers and yeah that's when I realized

ah, that's how you get power. That's how you get money. And that's what drove me for the first, I don't know, 10 years just trying to get power. Are you actually going to tell me that it's not driving you now? Definitely not. Well, talk. No, I mean, how many times can you ring the register

or be famous, not famous, famous, not famous, not famous. You do get to a point where you realize it's not what matters. And it doesn't correlate with happiness. And then you have the people around you and you watch people get wealthy and you watch people get famous. And then you see it's typically a negative correlation. More power, more money, more problems, more sadness, anxiety. And you see it all the time.

Our friends at Corian provide wealth management services centered around you. Corian's goals are to exceed your expectations, simplify your life, and help you establish a legacy that lasts for generations. Corian has been helping high achievers just like you enjoy their lives more fully, preserve their wealth, and provide for the people, causes, and communities they care about. They're one of the largest integrated fee-only U.S. registered investment advisors, and Coriant has deeply experienced teams in 23 strategic locations. Each team has extensive knowledge spending the full spectrum of planning, investing, lending, and money management disciplines. The team at Coriant put the collective

power of their expertise into building you the custom wealth investment and family office solutions that can help you reach your holistic financial goals, no matter how complex they may be. Real wealth requires real solutions. For more information, speak with an advisor today at coriant.com. That's coriant.com. Well, I not only see it all the time. Thank you for that. Wasn't that a better opening? I know where he's going. He's trying to make me cry. It'll work. No, Jason, I'm just trying to make sure that people know that you've got a real heart. Thanks, man.

Okay, and I've known this guy a long time, maybe longer than some of you have been alive. It's been 30 years. And he's got a heart that's made out of gold. Okay. And to jump off on his point, his question to me was, so there you were. Yeah. flat iron partners, partners with Fred Wilson, walked away from that.

What a fucking asshole I am, because I walked away, right? Well, I mean, I think you did very well, but you didn't do the next cycle. You got off. I got off. I got off the roller,

the merry-go round. Yeah. I mean, and to be clear, so the story is I was 38. How many people are approaching 40? All right. You're going to be okay. You're going to get through it.

I promise you. I'm the old man. On the other side of the room, you're going to be fine. You're going to be fine. I was 38. And then, you know, at that point, I was, I often tell this story by citing New York magazine, which called Fred and I, the princes of New York. But now I'm going to change that story.

I was the Jason Calacanus. my day. No, you guys were big deal. We were hot. Definitely. And it seemed like everything that we touched turned to gold. And it was not far from the truth. You had a string of close to a dozen investments that became unicorns, and you did it

out of New York, a place where people laughed at that nobody would ever be able to do it from there. And you guys did it over and over and over again. Right. and the more successful I got, the more miserable I became. There it is. Because one of the things that can happen is that you start to play for the audience. You start to get accolades and affirmation for how well you're doing.

Hey, you're doing a great job. Fantastic. Keep doing what you're doing. But I don't like to do what, but keep doing it. Right. and as my 30s ticked on, I got to be around 38. And there's a seminal moment, which I'll speak to now. And I detail all this more in my first book reboot than in the new book, Reunion,

in which I was, you know, a big-ass VC. I had a portfolio company in San Francisco. And I had to get on a plane and fly across the country and fire the CEO and then get on a plane and fly all the way back because that's what you were expected to do. And I got into the house after this incredibly exhausting day. And my then daughter Emma, my daughter Emma, who was then three years old, she's now 31 and engaged to be married. Yeah. It was at the top of the stairs. And I looked up at her and I spun around.

And as I was collapsing and going down, hitting my head on the bathroom door, I heard her say, Mommy, Mommy, Daddy died. And I said to myself, what the fuck am I doing? Who have I become? Prince of New York the Jason Calacanus of my era and I am never going to stop giving him

Oh God, it's so brutal It's so brutal Because as we said last night That's what you do when you're from Brooklyn That's how you show love When you're in Brooklyn Well, as a survival take, people don't understand Because what you do is you sit on the stoop

Right And you just make fun of each other That's right And then you make fun of your moms And your brother and your dad. And whoever cracks first, that's like losing. So you just break chops incessantly.

Incessantly. Incessantly. But it's a joke. That was the beginning of what took about a year and a half of realization that this was not the life that I was meant to live. That didn't matter how successful I was. And I was pretty good. This is not what I was born to do. You know, I went through 9-11.

which kicked my ass emotionally. Fred and I wound down flat iron partners. He went on with Brad Burnham to start Union Square Ventures. I joined J.P. Morgan. If you ask him, he will tell you he threw me to the wolves at J.P. Morgan in order to get us out of the contract we had to them. I don't think he did that. I just felt I could not do it again.

and I took this sort of interim step of joining a big $23 billion asset undermanagement, private equity firm. I did four or five more investments, and I was still miserable. From that point, I was working at J.P. Morgan, and it was a few months after 9-11, February 2nd, 2002, and I was down at Ground Zero. which is what we called the pit, the place that was left over, when my old feelings of suicidal ideation came back. And to be clear, I had spent much of my childhood in depression.

So when this came back, it came back with a vengeance. And I made the best decision of my life at that moment. I decided not to jump in front of that train. and anything good that I do in the world today stems from that moment deciding that this was not going to be way it was going to end. Anyway, don't mean to bring you all too down. So that's how I left the venture capital business. I wandered in the desert for a few years. I had too many stupid board seats, 27 at one point at the same time.

and eventually trained to become a coach. And I've been doing that now for 23 years. What is it about that moment in time and you look back on it and you have distance from it? That made you think that that was a viable option, like to just end it. Like what goes through a person's mind that they're just like, they're so miserable? Because you also coach people,

you probably dealt with people who've had tremendous loss. Like you were winning and you had this ideation. There are people who are right now, there's been a tough two years, shutting their companies down, losing their identities, lost tons of money, lost personal fortunes.

And, yeah, suicide's like real thing. So what was, what takes somebody to that point in your experience, not just your experience, with the experience, working with coaching people and stuff like that?

Yeah. So think of me as a prosumer as it comes to psychology. I'm not a therapist. I am a coach, but I have, through my own lens of my own experience, spent a lot of time kind of on that question. We've talked about Tony, we've talked about other people that we know. And I mentioned that I'd grown up with depression. How many people have read reboot? I know that there's at least one.

Okay. So you know a little bit of the story about how rough my childhood was. It sucked. I mean, you know, but how many people's childhood sucked? You know, there's a lot right. There we go. There we go. Okay.

So I think that what happens is when we come to that point, the depression and the sense of overwhelm, is so great that we're convinced there's no other way out. We're convinced that this is the only way to end the pain. And what it does is it actually lies. Like the belief system is a lie. Because what it does is oftentimes we will ignore the people that we will hurt and we stay focused on our own struggle.

And so I often think of it as a moment where I felt trapped. A moment where I felt like I had made the major change in my life. This is back to being 38, back to 2001. And to be clear, the depression seemed to actually have begun to peak or come on strongest, oddly, in December of 1999. when things were up into the right

everywhere when Yahoo was added to the S&P 500 this just happened to Uber the other day I did yeah

Yahoo was added and I owned yeah yeah and I owned a ton of shares because we had sold Geo Cities to Yahoo

and the more that stock went up the worse I felt which you want to talk about mine for a That's a real, real mind-de-h. And so from that point, what ended up happening was I started to feel like I couldn't breathe.

Like the more success that we had, I couldn't breathe. And then what happened in March 2001, or March 2000, I think was the crash. March 2000 was a crash. And then September 11th. And then September 11th. So I'm in this like fog of like, and I remember saying to Fred because we were like, we got to get the hell out of our, we had a single investor relationship with what, what, what became J.P. Morgan Chase. And I said, I got to get the hell out of this relationship.

You know, we're like hampered because we got one investor. And if they don't like something, we can't do it and all this stuff. And I said, I can't, I can't commit to fundraising. I can't go forward. So it was in that period, I made the change. I joined J.P. Morgan. I thought I was going to feel better. I didn't feel better. I was like, what else do I have to do?

And to be clear, I was married with three kids. And again, the best decision of my life was choosing to live. I think that there was a part of me. I mean, I can't look at this guy without thinking of Brooklyn. So forgive us for constantly mentioning it. But there's a part of me that goes all the way back there, which is resilient. Yep. You know that part.

Sure. It's like, knock me down and I will pick myself back up. Yeah, of course. Right now, startups have to do more with less. And fundraising, well, we all know that's really hard today. So if you need tech talent, but you don't have the time to interview dozens and dozens of candidates, you need to check out lemon.io. They have thousands of on-demand developers to choose from.

and these devs are vetted experience, result-oriented, and they charge competitive rates. Great developers are incredibly hard to find. We all know that. And when you find them, it can be hard to integrate them into your team. Well, lemon.io handles all of that for you. Startup's choose Lemonio because they only offer hand-picked developers with three or more years of experience and very strong portfolios.

Only 1% of developer candidates who apply to Lemon.io actually get into the talent pool. And if something ever goes wrong, lemon.io will get your replacement, ASAP. A couple of my launch founders have worked with lemon.com and they've had great experiences. So they've been tested, battle tested in fact. So here's

a very easy call to action. I want you to go to lemon.com slash twist and find your perfect developer or tech team in 48 hours or less. And Twist listeners get 15% off their first four weeks. So stop burning money and hire developers smarter by visiting Lemon

In that period of time, this is when Brooklyn wasn't cool and fancy. It was like about survival. And it wasn't cool to be from Brooklyn at the time. And you were trying to get out of Brooklyn. Right. The hope was that you could have the escape velocity to get over the Brooklyn bridge, get through the tunnel, and get to Manhattan. Get over the East River.

Or maybe get to California. And you knew like one out of like every two or 300 people made that jump. Yep. And you were like, well, that guy, that gal went to California. this person went to Manhattan. They got a police in Manhattan. They're in Manhattan. The city.

You got to the city. And that was my whole life. I got to get to the city. I got to be able to have a key and a door in the city, get a loft in the city, and then I've arrived. Yeah. And, but you have that fight in you where you can never give up and you've been through a lot of stuff. And so you did a lot of personal work. And then you started working with founders.

Yeah. And so let's start talking about founders and what that means because we've established here, sometimes being successful, sometimes checking all the boxes does not lead to happens. When do you typically engage with founders at the firm? The firm is also called a reboot. I'm always on brand, by the way. So the book is and then, yeah, and you named it reboot. You rebooted your life in a three-finger salute. control,

alt delete. It's like, you don't reboot things anymore, but, yeah. Well, sometimes you still

smack it in the side. You're buying it. Yeah, it used to work, actually. Someone was wrong with the fan or the card wasn't incorrectly.

But when do you start working with founders in the firm? And then what, what is the theme with founders that you notice, that drives the engine? And then,

I think we can get into maybe the level, the levels of being a founder because the thing I've noticed is the ones who are successful typically have something broken. Parent relationship, not an ideal childhood. And they got a chip, they got something to prove, and that can take you very far. But it can't take you all the way there, can it? nine so two of my clients are sitting right here and they're both going let me let me take the first

question so i'm going to speak generically about like when a coach drops in and and versus a me because it's similar but a little bit different so um kind of anywhere in the journey in the arc of the experience, it might be helpful. I have worked with people precede. One of my clients, I started working with him when he was employed at a different company, and I was coaching the whole C-suite at that company, and then he got into his head. He wanted to leave and start another business. And with the CEO's permission, we all sort of worked it out, and I continued working with him.

And he launched that business. And I think it was 12 years later. Here we are. And he's just recently stepped down as CEO, stepped into the executive chair position. And he's much happier, by the way. So, you know, there are people who will work with a coach for a short period of time on a particular issue. And they'll come in for six months. and they, you know, sort of get them through a difficult time.

And then sometimes there are people where the coach becomes this relationship that helps you navigate, how to transition from being a founder, if you will, to a CEO. Explain that. Yeah, explain the difference. Well, I mean, you all know, right? I mean, it's a tremendously challenging transition. you go from many times and many people in what we would call Silicon Valley. Let's use that in the broadest. Right, the tech industry.

Our product-oriented leaders. So they found a company because they have the brilliant idea to launch this product, this service. And they might have co-founders sort of sorting it through. And then they run into, right, Jason? they run into the reality of managing people. Anybody know that reality? Okay, this is a quote for you. Jean-Paul Sartre in No Exit says,

hell is other people. Okay. Okay. Cause human beings are really, really a pain in the ass. Why don't they just do what I tell them to do? Right. Now, you made the conversation. comment about us all, you know, all founders are wounds. You want to know the truth?

Yep. Everybody has. Everybody has. And one of the hardest parts of making a transition is creating the structures that have enough process in place so that the organization can scale while dealing with all the people bring into the office because they are remotely Zoom. The org. Right.

The org. Thank you. Well, let's go one level deeper because I do agree. Founder. Go deeper? Well,

I mean, might as well. We're here. There's zero to one. Sure. Okay, there's nothing. I created something.

Right. We're incorporated. We got money in the bank. I raise the funding. We birthed this product. Some number of people love it. Okay, great. And now we're at 30.

people and it has to go to 300 and it's got to go from 1 million to 30 million to 300 million. Okay. Yeah. Operations, all this stuff. But then let's go inside the person because it takes a certain amount of to be the zero to one founder. Then we'll just call it the founder. Creativity.

It's intimate. And you can manage the personalities of under 10 people relatively easily. Not easy, but relatively easy. think. Now you start getting to hundreds of people. It's just something very different, maybe not as enjoyable. Then there's also purpose. Why am I here? Right. So let's assume it is successful, right? Let's say you're the 1% to 5% of companies that do become successful, get escape velocity. A lot of that I think what you then deal with is, correct me if I'm wrong, purpose, why keep going? Is there something else I should be doing? Is it a constant,

voice in my head. You could do this. You could do this. The drowning in opportunity. That's a constant voice in your head. Absolutely. Just too many opportunities. Right.

And what if I took that path or that path? Choose your own adventure here. Choose your own adventure there. Then I have some friends who have Asperger's or are they on the spectrum. And it's not, what if I do that, that and that in the ADD brain, ADHD brain. Yeah. It's the, I'm going to block out everything to the detriment of important things in the world, people's feelings, relationships, whatever, and I'm just going to go deep into this one thing.

Right. Yeah. And so there's a higher level, I think, maybe that then people get to. Purpose, should I be here? Should I not be here? What's the point of it all? When does that emerge in all of this? Should I coach him?

You knew he's going to do it at some point. Oh, yeah. Okay. Wow. Tell me about your father. Exactly. Um, notice in your, um, example, Jason, the company that you're talking about is succeeding. Yeah.

Notice that. Because there's a, you know, very broadly speaking, there's a whole set of other issues when you don't successfully raise money or when you don't find product market fit. Or it should never happen to you. You run out of cash. It's a whole different experience. What Jason just laid out is the pain that can come with succeeding. I thought that if, fill in the blank, right?

We hit 100 million A-R, we hit 500 employees, or we rave that round of financing. that everything would be better. Or we go public. Then I can finally relax. Yeah. And yeah, you're shaking your head, you know. I mean, the problem is not the process. The problem is not the industry as much as the setup of what we believe as we go into it.

because what can happen, even in the most successful experiences, is that we attach our sense of self-worth to the success. And so when success does what it's supposed to do, which is it becomes fleeting, or when life does what it's supposed to do, you remember reboot in chapter seven, I talk about life on the roller coaster. and that the mistake we make is that we think that life is not supposed to be up and down.

And we isolate that feeling and we're feeling up and down and up and down. And what's our conclusion? We must be broken. Because everybody else has got all figured out. You know, we've been doing boot camps at reboot for 10 years. And these are multi-day immersive experiences. And when I first started doing the boot camps, the first thing I used to say on opening night was the bull-h-h-stops here. We're crushing it stops here.

Because nobody crushes it constantly all the time every single moment of the experience. That's just not normal. It's hard. It's really hard. and one of the challenges a lot of with a lot of the media that's associated with this experience called being a founder is it promulgates the myth that everything is okay that's always up in the right because that sells more than oh how was your day today yeah what did I say to you before Jason Day? How much glad you? How much glass, did you eat this weekend? Right? A lot of glass, a lot of broken glass.

Right. And you choose to get on the roller coaster. I mean, this is one of the profound things you said to me at some point. What have you done to create your own circumstances and suffering? Right, right. There's a more precise way you say it, but essentially... It's how have you been complicit in creating the conditions you say you don't want. So we architected. Our unconscious architects it. Our unconscious architects it. Our unconsciously. conscious architects it. So we create these,

and I use the word complicit purposefully because I want to evoke the notion of the accomplice, not the guy who's sticking up the bank teller, but the guy who's driving the getaway car. And it's really important.

This is true in our leadership journey, but it's mostly true in our journey to becoming an adult and being able to withstand that role. roller coaster is we start to ask questions like, why did I start this business in the first place? What was I looking for?

You said it well before. You're like, this is a kid. He's still a kid from Bay Ridge who's looking across the East River to the city, hoping to get to the Emerald, the Emerald City. Yeah. And you just kept going west. Yep. Right.

and like what happens when you realize you're already in the Emerald City. Yeah. All right. Let me tell you about how I'm able to manage thousands of applicants and hundreds of attendees for Founder University. Every time we do a new cohort, which is quarterly, we have thousands of people apply. We track them all in Coda. Cota is a dock on steroids. And then when they get accepted, we have three, four, five hundred founders in Codally.

side of Founder University, and every week, I ask them to send me an update on how their startup is doing, and then we can look at all that in Coda. Then we send automated reminders to those folks, and we track their week-over-week growth with these beautiful charts that Coda produces for us. Let me just tell you, I was going to build all this with a developer, but my team, they built an app in Coda in days and saved me, I think, 100 large. They also just announced Cota 4.0. This includes Coda AI. Basically, they've made a work assistant that knows your company. And then Coda AI will actually perform tasks for you.

But here's the best part. It's free for doc makers. You can make all kinds of great documents inside of Coda. You can build databases and great workflows. This is the future. Honestly, if you want a platform that will empower your team to work, organize, and collaborate together at lightning speed. And speed matters.

I always say this velocity. We'll get started with Cota today. With a free trial, head over to Coda.io. That's Codda.com. slash twist and get started for free. I am obsessed with Coda. I love Coda. So go to coda.io slash twist and get on Coda today for free.

There's an interesting thing. You know, I've really thought about motivation. Yeah. I've really thought about it. And I was watching that Michael Jordan documentary. I don't know if you're watching it. Yeah, yeah. And you realize, wow, we all enjoyed watching him.

We used to go to the Knicks game. Yeah. You guys had good Nix tickets. Thank you for taking me so many times. And great seats. We'd see Michael Jordan and it's just spectacular to watch somebody at the top of his game.

And then you watch him looking at people talking about him. And he's so full of piss and vinegar and anger. You realize he didn't enjoy any of it. Now, we enjoyed it. We were watching the master at work. We were watching him do the double nickel game. We were watching him soar through the air,

hit shots. We couldn't believe the flu game, all this stuff. And you realize, he was miserable the whole fucking time. Right. And he was making everybody around him miserable. And he's a billionaire.

And the more successful he got, the more he made people miserable. Yes. And he's still miserable. And Oakley doesn't talk to him and Pippin doesn't talk to him and none of those relationships ever lasted. Still miserable.

I know a good coach for him. Exactly. But, you know, it was, he's like, I took that personally. I took that personally. It's like, ah. this person was so obsessed with winning. That he manufactured his own architected,

his own, he was complicit in making his own suffering to win and to be the greatest. And now he's still there. He's still absolutely unhappy. I just thought, wow, that is up.

And I look at my early career, I was battling everybody. I used everybody as, as an adversary at New York Alley Cat, whoever it was The way you went out to the at New York guys was crazy. Deranged.

Deranged. That's right. Deranged. I'll just tell... How about Nick Den? Deranged. And I realized when I was watching the Michael Jordan, they're going to do not put myself in sleep, but I do put the disease in there, which was

I needed to battle somebody in order for it to be meaningful for me to get in that office every day at 8 a.m. and stay up until 2 a.m. And I'd ever win. I had to win. Had to win. And with the at New York guys, they were the nicest guys.

Good journalists. Great journalist. And they started at the same time as me, this weekly newsletter where they did a roundup. And I was doing a monthly magazine. And then one time they scooped who was going to be on the cover of the magazine, they put in their newsletter. And some company was launching. I was like, motherfucker.

got my story. I have to destroy them. And so I called the meeting and I brought my 12 editors in. I said, how do we beat him? I said, we can't. I said, that's not the right answer. I kicked the person out of the meeting. Somebody tell me an answer or else I'm just firing everybody starting over.

I don't need any of you here. I was a lunatic. So everybody's like, well, we could start a weekly. It's thought about it. I was like, yeah, that's what we'll do. We'll start our own weekly email newsletter. And then I said, no. we'll go dally.

They did. Silicon Allie Dally. Hire two more people. We don't have the money. I said, sell more ads. We're doing Silicon Alli Daly. Well, how do we supposed to do that?

And then how do we have a monthly magazine and then scoop ourselves? I said, I don't care. I want those guys to wake up next week and just shake their fucking head and say, Calicanus. Fibon Calicanus! And I did it. And they lost their minds.

Oh, God. And then I just put two people on it, three people on it. Then the Alley Cat people got put another newsletter and Silicon Alley. And they did an event. Oh, yeah. And this event got all this press. And these two very wonderful women were running it. They were incredibly charming and nice.

Whoever. I said, I have to kill them. And I said, we're doing our own event. Silicon Alley 1996 1996 1997 1998

yeah I said okay who's been in the magazine in the daily for the last month give me every single name email every single person and tell them I want them

to come to my event give me the top 50 people in Silicon Valley got me the list of the top 50 people invited them to the event and then I sent an email where will you be on February 26 and 27

Silicon Alley 1997 and I listed the 50 people. And I sent it up. Fred on top. Yeah, put Fred on top. Everything.

You guys on top. And I just went after them. And then the New York New Media Association. Oh, God. Then they decided that they were going to put three people on, they're going to put some people on the board. And they interviewed me, Stephanie Simon, and I think it was Jason Trevokas from out in New York. And they put those two on the board and not me. And then you took them down.

I said, that's fucking it. I'm going to go crazy. And it worked. And then I got in the fight with Nick Denton over Gawker. Right. and he was going to compete with me. Right. And he wrote a blog post, like, kind of giving me a hard time.

And I said, okay, who's his top writer? Elizabeth Spire? She's doing Gawker. I found out how much she was getting paid. I said, I'll double your salary and I'll give you a MacBook air. She said, I'm going to New York Magazine to be a writer for a magazine. This blog stuff is bullshit. I said, okay.

I talked to another blogger. He said, oh, no, he doesn't make any money from Gawker. I said, how does he make all this money? He's Modo. Is Moda the gadget thing? Yeah, the gadget thing. I said, who runs that? Peter Rojas.

I went to Peter Rojas. He said, Peter, I'll double your salary, give you a MacBook Air. He said, what about equity? I said, what do you mean equity? He said, well, Denton promised me I would own some of Gizmodo, and then he renamed. I said, I'll give you equity in Weblogs, Inc.

I'll make you a millionaire. We have to agree to do it right now. He said, okay, great. He says, but I have to, I can't commit for two weeks because Nick's going on vacation on Sunday. He's been working like a dog, and he's going on vacation so I don't want to tell him until he gets back. I said, tell me more.

He says, he's going to Argentina. I said, when? Sunday. I said, how do you know? He said, because I've got to meet with him before he goes to the airport because we've got to make plans and I'm managing everything from us. Oh, great. I said, okay, I'll pay you your first month now and get to the MacBook Air. I want you after you meet with him to email him your resignation so he gets it when he lands.

You didn't realize how. evil this guy was, did you? Peter Ross left to me, he goes, you're all core. I said, yeah, and you're going to be a millionaire. And sure enough, I had the right to buying gadget from Peter for like a small amount of money, like a half million dollars or whatever.

And when we sold, I ripped that up and I just gave millions of dollars. And I said, who couldn't have done it without your buddy. And then Nick Denton call me after he came back. He said, lunch? He said, okay, we went to lunch. He said, we're the only two people. doing this blog thing. We both know it's going to be huge. Can we agree to a non-aggression pact? Non-aggression. I've never heard of such a thing. Tell me more. He said, I'll never

poach any of your people. You never poach any of mine. We just split the pie up. And we charge, we pay the writers the same amount. Is it price fixing? Isn't that illegal? It's like, maybe. I said, I'm in. Sounds good. And then we went to battle and we launched A car blog versus a car blog, sports blog, for sports blog. But we never. And I just look back on myself at that time like, oh my Lord, I was insane. I was deranged. And that was all my dad.

I was just going to ask. I was 100%. My dad owned a bar. He kicked people's asses for a living. Right. I'll never forget you telling me about the baseball bat and the gun and all the stuff that was under the bar. My dad would give me his gun to put that in the ice box. Got it.

put it in a Ziploc bag, put it in the ice. You all knew this about him, right? No, I don't talk about the . Yeah. I thought we'd make it real here. Can you still see it? I don't have that aggressiveness anymore. I don't want to kill people anymore.

No, I don't. I don't actually want to defeat people. Right. I mean, it's great that lift fell. I will say that. But I don't have that motivation anymore. The motivation has changed. And that's what I was sort of getting at is like, when does the motivation change?

Well, when did it change for you? I think it changed for me when I saw how great it was to help friends. And I realized a lot of the people who I was friends with looked at me as their best friend and the person they would call for help. Right. And advice. And when I saw that, I was like, that's more meaningful to me. It's more meaningful to me to be the first investor in somebody's company to have helped them, to have had them on the podcast, whatever I did to help them and have them say, I really appreciate that. It's more meaningful to me, and it has been more meaningful to me for 27 years to be someone who walks up to me having read my book and said, this really changed my life.

This really helped me. The unlock from me that released me from my own crazy suffering that would drive me across the country and collapse in front of my daughter was actually looking outward and saying, what can I do to help? you know to me everything i do is organized around making sure you don't collapse in front of your daughter and feel the way i did at 38 and i mean i said this to you today i said this to you over to you i am incredibly lucky i get to do have these kinds of conversations all day long not so as we've been, but I get to have meaningful conversations and help people all day long, and people will pay me. I mean, sometimes they're on time, sometimes they're not, but, you know, they'll pay me for that.

And so let's talk about being an enlightened leader. Let's say you get past the Jordan battling everybody being a miserable but winning, and then you get to some level of purpose and you actually start enjoying it, you start finding meaning in it. How good can he get? And then how do you keep the fire? Right.

That's the question. Everybody asks. How do you keep the fire and the desire to win because this is a hard pursuit? It's a competitive pursuit. It's not easy. It's a roller coaster

with people fighting with swords in the roller coaster cards. Right. Like it's like literally gladiators on a roller coaster. I mean, just regular life is a roller coaster. In this one, like, people are jumping from car to car trying to decapitate each other. So how do you then, in the eye of that storm, find purpose and resolve, peace, equanimity, whatever word we want to use here, or is it not possible if you pursue this? Is it always going to be sort of in balance or unbalanced or intense? The answer is in the setup. And the setup is I can either be competitive or be a nice guy or a nice person. I can either be successful or be a nice person. That's the setup.

And it is true that the kind of drive that you were describing about yourself, and we both know plenty of people who have that kind of drive, who are still driven in the same ways, it is true that the world and markets can reward that behavior. It is true. It's almost designed to do so. It is almost designed to do so. One might argue.

So you have to sort of go back and say, what does success look like for you? How much is enough? And I'm not going to sit here and take a moral stance and say, you have enough, stop, right? That's not for me to decide. but I would ask you, you know, we were talking before about the unconscious drives, I would ask you to consider how much is enough for you. And whatever answer you come up with, do a little bit of what I would call radical self-inquiry and ask yourself, why is that my answer?

Because if the reason for that answer is because I continue to try to rescue my father who's stuck behind a bar, because I never want to end up like that, then no amount of money, no amount of success in the world will close that hole in your chest. Because what you've done is outsourced your sense of self-worth, your worthiness of being loved, to some ephemeral object that's out there outside of your control.

Now let's talk about the opposite. It is entirely possible, but it is hard, to stay competitive, to want to build, as one client told one of my partners, dope shit that people pay a lot of money for. It's a technical term.

It's a technical term. And not be a jerk. It's possible. And it's really, really hard. Because the forces collude. And so from where I said, I think it forces us to make certain choices. How much is enough? How successful do I need to be to rescue my parents, my grandparents, my great-grandparents, to live up to the sacrifices that they may have made to prove all those doubters wrong?

Yeah, no doubt of me. Because he was just a kid from Brooklyn who got doubted except by me. you're sure right so he was just going to prove everybody and you know as a motivation that's okay it's great powerful until it's no longer works correct so did i answer that question i think pretty well yeah no i think it's i think it's probably one of the things i see in the successful founders

uh over and over again which is I have to be the person who deals with the problems that my team can't solve. I get all the worst problems. I get all the hardest things. And then people disappoint me. And to make dope shit, as your client explained, sometimes that requires,

well, this person is not capable of making the dope shit. They have to go. Sure. But they've been here from the beginning. Sure. And they're not dope anymore. The bar has been raised.

Sure. And they got to go. And, you know, that is one of the hardest things. You can be an asshole about doing that or you can be a kind about doing that. Yeah, but even when you're kind, still sucks. Oh, it's always going to suck. Yeah. This is not about sucking, not sucking.

Yeah. It's always going to suck. They'll be suffering. Always. Yeah. Is it consistent? The question is how do you deal with it? What are the most acute things people call you about regularly?

I'm dealing with this. I would suspect firing a co-founder and having to get to- getting to the point of navigating the fight with co-founders. Yeah. Not even getting into the vision of being able to get clarity and say one of you has to go. But just navigating the space. you know, and what I often see is people don't resolve it. And then, you know, like, invariably I'll get called in and there are co-CEOs and I'm like, uh-huh.

Yeah, the co-ceo-dead titles. That's the reddest flag you could wave. What was the fight you refused to resolve that led to that structure? Right. Well done, Jerry. When did you become a coach? I'm like, I'm like sitting here, like looking at this guy. You know, it's pretty straightforward.

forward. Tony died. Yeah. He was the person who wrote the book delivering happiness, but he couldn't be happy. And that sent me on my journey. Right. That was a mind for it. It was a my, and that set me on my journey to just,

hey, wait a second. Am I actually happy? I mean, I checked a lot of boxes, but I'm actually enjoying all this? And then I just made the list of the things I don't enjoy, things I do enjoy. And this list got super deprecated. And then this list got longer and richer and better.

And did you lose your edge? Did I lose my edge? I feel like it's a different edge now. It's a different edge. I was like taking that sword and swinging it all over the place. Berserker. That was the fighting style. And there's like an amazing scene in the Seven Samurai.

There's a character to Shura Mufune, who in the Seven Samurai is the berserker. But then there's some other guys in the seven samurai. And they're just a scene where like, a guy comes charging at one guy. You just see, whoosh. And then the guy just falls. He's cut.

And the sword's back in the sheet. I can just, when I need to use that sword, or like, it's a great scene. When you get older and you get deft at this stuff, Obi-Wan's in the bar at Moes-Sisely, and somebody starts to fight with Luke Skywalker.

This little one's not worth your trouble. I'll tell you who's worth a trouble. rubble, and then they attack him. And then you just see, and then the lightsaber comes out, and then gets back on Obi-Wan's belt, and he's an old man. And you see the arm on the ground. And then the bar just goes back to normal. That's what I can do now. And that scene was taken from another Akira Kurosawa film, Yojimbo. It's about a Ronan, basically, solo samurai.

And I have just channeled myself to be very deft, and I only take out the sword when I need it. And it's incredibly rare that I need to be a berserker. But it's like a superpower. Just take it out when you need it. It's not the default mode anymore. The default mode got me here. In this deft mode, it's like you can just go much further.

You could take on the entire empire by yourself. And you can make other. people great and you don't need to be berserky. You certainly don't need to go to somebody's office and have them get you arrested. I mean, that's, I salute you, sir. I mean, in my derangedness, I never considered going to the at New York or Alleycat office to confront them for being good people and being normal. You did it at parties.

I did do that, yes. But, yeah, but I mean, anyway, I do think, like, you do not lose your edge in a evolving. You just gain. You gain and you gain and you gain. Yeah, like, there's high leverage activities. If I take my daughter's two hours of skiing and then work for 12 hours, they will talk about those two hours of skiing for a year. And so I just make it so, hey, we're going to do these two hours skiing. Here's the map. These are the trails we're going to do. And we're going to have the best time ever. I'm going to go look for these creatures or whatever. And it's really about thoughtfulness and presence, right? He can do things being present with the person. I've seen it

over and over again in 10 minutes, what might take another person 10 years to have processed. Deafness. Like Professor X. Everybody, Jerry Colon. Thank you.