Jerry Colonna on 'Reunion': sustaining founder drive, enlightened leadership, and more! | E1864

0:00Very broadly speaking, there's a whole set of other issues when you don't successfully raise money or when you don't get money or you don't work. happened 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 Week in Startups is brought to you by Coriant. Real wealth requires real solutions. Coriant 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.

0:54Go 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. Did you know that, Jerry? This is your third? I thought it was the fourth. Well, 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.

1:37So you've been on a couple of times. um jerry's one of my oldest friends uh in the industry one of my oldest friends i met jerry in 1994 ish 93 maybe the internet was just emerging uh jerry was um working at a company called lycos 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 percent of the web right they had that too point communications yep point communications and so uh 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 meet jerry uh and i came to his office and we became friends he went on to do flat iron partners with uh 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 rabid capitalist in the dot-com era placing bats working 70 80 hours a week and uh 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 uh you work with i don't know how many dozens of founders but tell us your journey from you know a venture capitalist peak dot-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 um so the real story is okay he was homeless and penniless not too far from the truth in fact and he was he was hawking this magazine that he had started yeah cyber surfer my first magazine cybers right that's how like unhip he was and at 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 right and and And I think I gave you your first job.

3:56Yeah. So I said, hey, 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 an 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 Island Reporter magazine came out, and Fred said, listen, the Silicon Island Reporter - And the Fred is Fred Wilson, by the way.

4:40Fred 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 uh the ad salesperson and i said oh okay uh what are you talking about your wife said she's at home with our kids i said okay so i called joanne wilson and the kids are screaming in the background she's like hold on a second get off that you're gonna kill yourself okay um so tell me about the magazine and i said well tell me about you and she said i worked in the schmatz business i said i'm sorry god bless you what and she said no, no, schmatz business.

5:20I was selling like clothes. What does that have to do with a technology magazine? There's nothing. I can sell anything. And I said, okay. True story. And she wound up working with me as my partner on it and 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. Okay. So, and the greatest deal of the century that Fred Wilson and I ever negotiated, our venture capital firm was called Flatiron Partners.

5:52The 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 a company called Razorfish. And I don't think we paid you. No, you did. You paid. Yeah, you did. Yeah, but it wasn't very much. It was$250 an episode. I had said to my, per issue, I said to myself, I'm going to 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 i it was a photocopy just we called it a magazine but it was a photocopy and the village printer up on 43rd street manhattan printed it but it was eight pages so i said it was like 12 cents or whatever so i said 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 2100 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 gonna do here he's like well i'm gonna put the magazines over here and then you come back with another thousand i give them to you i said let me tell you i'm a kid from brooklyn i'm trying to make this magazine i got a credit card there's no way two thousand dollars gonna work can we charge like fifteen hundred and see if we're like i'll just charge a thousand don't worry about it kid and that's when i realized if you ask people for a favor yeah they'll do it yeah but i told them the story yeah i said listen i'm just a kid from brooklyn i'm trying to make a magazine this is the first episode my cards can't hold this and so my first two investors i would joke with people were american express and visa right and i said you know the two 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 uh 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 the guy's 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 uh can i have one and i just 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 and i said power wow yeah media is power i've never had any power yeah 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 bearage they're next to each other duiker heights in the middle we were the tougher part of the it was all tough but yes that's not i mean bensonhurst was the mafia um bearage was the cops and the firefighters i don't have a problem they all hang out in my dad's bar they were great tippers um and uh 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.

9:34Are you actually going to tell me that it's not driving you now? Definitely not. We'll talk. No, I mean, how many times can you ring the register or be famous, not famous, famous, not famous, 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 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.

10:19Corian 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 spanning 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 then we're like he just i know where he's going he's trying to make me cry it'll work um no jason i'm just trying to make sure that people know that you've got a real heart okay and i've known this guy a long time maybe longer than some of you have been alive um 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 the the merry-go-round I mean and to be clear so the story is I was 38 how many people are approaching 40 alright You're going to be okay.

12:20You're going to get through it. I promise you. I'm the old man. I'm 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 Calacanis of my day. no you guys were big deal we were 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 yep and you guys successful I got, the more miserable I became.

13:19There 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 um as my 30s ticked on um i got to be around 38 and there's a seminal moment which i'll which i'll speak to now and i i detail all this more in my first book reboot and in the new book reunion in which I was 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.

14:31And I got into the house after this incredibly exhausting day, and um my then daughter emma my my daughter emma who was then three years old she's now 31 and engaged to be married yay um 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 am i doing who have i become prince of new york the jason calicanis of my era and i am never going to stop giving him oh god it's so brutal never it's so brutal um 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 tech people don't understand uh 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 brothers and your dad you just and whoever cracks first that's that's losing so you you just break chops incessantly but incessantly incessantly so it's a joke it's 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.

16:12That 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. um fred and i wound down flat iron partners he went on with brad burnham to start union square ventures i joined jp morgan if you ask him he will tell you he threw me to the wolves at jp 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 i took this sort of interim step of joining a big 23 billion dollar asset under management private equity firm i did four or five more investments and i was still miserable and from that point i was working at jp morgan and it was a few months after 9-11, February 2nd, 2002.

17:22And 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 the 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.

18:14I 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 when you look back on 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 you were winning and you had this ideation there are people who are right now it's been a tough two years shutting their companies down losing their identities lost tons of money lost personal fortunes um and uh yeah suicide's like real thing so um what was what takes somebody to that point in your experience not just your experience but 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 and we've talked about Tony and we've talked about other people that 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.

19:57I 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 um 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 the depression seemed to actually have begun to peak um or or come on strongest oddly in uh december of 1999 when things were up into the right everywhere when yahoo you were rich yeah yahoo was added to the s &p 500 this just happened to uber the other day did yeah yahoo was added and i owned uh 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 mind that's a real real mind and so from from that point what 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 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 uh investor relationship with what what what became JP Morgan Chase.

22:35And I said, I got to get the hell out of this relationship. You know, we got, we're like hampered because we've 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 JP 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.

23:24But there's a part of me that goes all the way back there, which is resilient. 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, experienced, result-oriented, and they charge competitive rates. Great developers are incredibly hard to find.

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24:39I want you to go to Lemon.io 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.io slash twist. in that period of time this is when brooklyn wasn't cool and fancy it was like about survival like you 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 or maybe get to california and you knew like one out of like every two or three hundred people made that jump yep and you're like well that guy that that gal went to california this person went to manhattan they got a place in manhattan they're in manhattan the city he got to the city and that was my whole life was that i gotta get to the city i gotta 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 um and so you did a lot of personal work and then you start working with founders yeah and so let's start talking about founders sure and what that means because we've established here sometimes being successful sometimes checking all the boxes does not lead to happiness when do you typically engage with founders at the firm the firm is also called a reboot you do i'm always on brand by the way always so the book is and then yeah and you named did reboot you rebooted your life um and a three-finger salute control alt delete um it's like you don't reboot things anymore but well sometimes you still smack it on the side you bang it yeah it used to work actually someone's 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 what is the theme with founders um that you notice that drives the engine and then i think we can get into maybe 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 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 nice 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 um i have worked with people precede like 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 you know 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, uh, is much happier by the way.

28:29Um, so, you know, there, there, 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 who, where the, where the coach becomes this, um, relationship that helps you navigate how to transition from being a founder if you will to a ceo because it's like that yeah explain the difference well i mean you all know right i mean um it's a tremendously challenging transition you go from uh many times and many people in what we would call silicon valley let's use that in the broadest right the tech industry um are 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 because 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 comment about us all founders are wounds.

30:11You want to know the truth? Everybody has s***. Everybody has s***. 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 s*** people bring into the office because they are remotely zoom you aren't right the org thank you but let's go one level deeper because i do agree founder go deeper well i mean we might as well we're here um there's zero to one sure okay there's nothing i created something right we're incorporated we got money in the bank i raised the funding uh 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 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 um not easy but relatively easy i 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 one percent to five percent of companies that do become successful get escape velocity a lot of that i think what you then deal with is and correct me if i'm wrong purpose why keep going is there something else i should be doing there's a constant constant voice in my head you could do this you could do this you could do this drowning an opportunity constant voice in your head absolutely just too many opportunities right and what if i took that path or that path right choose your own adventure here choose your adventure there then i have some friends who have asperger's or they're 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 um 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 gonna do it at some point 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 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.

33:55It's like, me. I thought that if fill in the blank, right? We hit a hundred million ARR, we hit 500 employees, or we raise that round of financing, that everything would be better. Or we go public.

34:15then I can finally relax. Yeah.

34:21And 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 it all figured out

35:29you know um i've we've been doing boot camps at reboot for 10 years and these are multi-day uh immersive experiences and i when i first started doing the boot camps the first thing i used to say on on opening night was the bull stops here the we're crushing it stops here

35:57because 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 there's always up in the right

36:37because that sells more than oh how was your day today yeah what what did i say to you before jason 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 circumstance 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 architect it our unconscious architects our unconscious architects it so we create these we we 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

37:41and 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 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 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 Foundry University.

38:39Every time we do a new cohort, which is quarterly, we have thousands of people apply. We track them all in Coda. Coda is a doc on steroids. And then when they get accepted, we have three, four, 500 founders inside of Foundry 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.

39:20They also just announced Coda 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 will get started with Coda today with a free trial head over to coda.io that's coda.io 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 um and i was watching that michael jordan documentary i don't know if you're watching yeah yeah and you realize wow we all enjoyed watching him we used to go to the knicks game yeah you guys had good knicks 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 the stuff and you realize he was miserable the whole time right and he was making everybody around him miserable and he's a 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 right 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 and i just thought wow that is and i look at my early career i was battling everybody i used everybody as an adversary at new york alley cat whoever it was the way you went after the at new york guys was crazy deranged deranged that's right deranged i'll just how about mcdenden deranged deranged and i realized when i was watching the michael jordan thing and i do not put myself as lee but i do put the disease in there which was i needed to have 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 till 2 a.m and i'm gonna win i had to win i had to win and with the at new york guys they were the nicest guys good journalists great journalists and uh 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 it in their newsletter right and then some company was launching and i was like motherfuckers 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 them i said we can't i said that's not the right answer and 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 let's thought about it i was like yeah that's what we'll do We'll start our own weekly email newsletter.

43:19Then I said, no. We'll go Dally. They did? Silicon Alley Dally. Hire two more people. They said, we don't have the money. I said, sell more ads. We're doing Silicon Alley Dally. Well, how are 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 head and say, Calicanus. F***ing Calicanus. 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 uh put the newsletter another newsletter and alley 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 courtney and whoever um i said i have to kill them and i said we're doing our own event silicon alley 1996 1997 1998 yeah i said okay who's been in the magazine and then 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 alley got me the list of top 50 people invited them to the event and then i sent an email where will you be on february 26 and 27th silicon alley 1997 and i listed the 50 people and i sent it up fred on top yeah i put fred on top everything you guys 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 they're going to put some people on the board and they interviewed me stephanie simon and i think it was jason travocus 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 it i'm gonna go crazy and it worked and then i got in the fight with nick denton over gawker right and he was gonna compete with me right and he wrote a blog post like kind of giving me a hard time and i said uh okay who's this top writer elizabeth spire she's doing gawker i found out how much he 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's blog stuff 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 his moto is it his moto the gadget thing yeah the gadget thing i said who runs that peter rojas okay went to peter rojas said peter i'll double your salary give you macbook air he said uh what about equity i said what do you mean equity said well denton promised me i would own some of gizmodo and then he reneged i said i'll give you equity and weblogs inc i'll make you a millionaire but you 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 till he gets back i said what tell me more he says he's going to argentina i said when sunday i said how do you know he said because i got to meet with him before he goes to the airport because we got to make plans and i i'm managing everything from us oh great i said okay i'll pay 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

46:48you didn't realize how evil this guy was he goes you're hardcore i said yeah and you're going to be a millionaire and sure enough i had the right to buy a 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 him millions of dollars and i said i couldn't have done it without your buddy um and then nick denton called me after he came back he said lunch it was the email i 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 riders 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 with 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 well i was just gonna i was 100 my dad owned a bar right 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 the bar my dad would give me his gun 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 then i don't talk about anymore but yeah i thought we'd make it real here you still see it i 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 failed i will say that but uh i don't 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 um 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 for 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.

50:12And 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 down 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.

51:04how good can he get and then how do you keep the fire right that's the question everybody 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 imbalanced 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.

52:06I 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

52:59and 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.

53:10But 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.

53:55Because 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, as dope that people pay a lot of money for. It's a technical term. It's a technical term.

54:32And not be a jerk. It's possible. And it's really, really hard because the forces collude.