Full Transcript for It's not AI Doom, It's a Fourth Turning

So just to be clear, everything we said before we started ruling is now on the record. He's evil. I believe he's a psychopath. I don't think any US lab can slow down AI because China will lap us, they'll win AGI and they win. Airbnb, I was like, I'm going to do it, but I wasn't 100% sure it was going to hit. But I put like 100 grand in and that turned into a fuck ton of money for our LPs.

I broke the story of Google buying YouTube and I had the price and everybody laughed at me. Like the Wall Street Journal was like, who is this guy? Like this didn't happen. And then it was true. Never said how I got the tip. Are you lying? Am I lying? This person said, I think crypto might be dead. That's what I was waiting for. If you have given up on crypto, the bottom is reached.

Bitcoin realistically can't be stopped. And that's going to save us all.

Hey, everyone. Welcome back to the Delphi Podcast. Today, I'm in person with Michael Arrington. I'm excited for him to join us. Michael founded TechCrunch from a Silicon Valley home back in 05. He built it into one of the world's top publications. It's where founders, tech communities used to break breaking news. He ended up selling it to AOL.

You were one of the first people, you were at one of the first Y Combinator demo days in 07, covering all the interesting founders, created Crunchbase. I know you said you got a lot of mileage out of this, but you were Times 100 most influential people. And then you backed Uber, Airbnb, Pinterest, and founded Arrington Capital. So just to be clear, everything we said before we started ruling is now on the record.

And I can also speak like the Time 100 thing. Oh, yeah, for sure. Okay. So we can talk about Steve? Anything.

Talk about Steve McLaughlin, who was on one of your great podcasts recently. He was just on. Yeah. Well, that was a very nice introduction. Thank you. Yeah, of course. Thank you so much for coming on. It wasn't easy to get you. It's my honor. It's not easy to get me? It was not easy to get you. This is my favorite podcast. I appreciate that.

Like, I watch just about every episode. Are you lying? So am I lying? No, I did say I don't understand everything. You get super tech.

But you guys are just like honest journalists. Like, it's just great to watch. So, you know, uplifting and all that. So appreciate it. You know, all that. We're here to host the best guests. We're here to make money. That's the goal. Mike, you every podcast I listen to about you, you always reference this concept called the fourth turning.

It's this concept that every hundred years the world changes and we're in. It happens within four 20 year segments where everything's great. Institutions are valued. It kind of breaks down. There's this crazy reset. Yeah. Is that where we are right now? Well, it's interesting. Have you had you ever heard of the book, the fourth turning? Not before Kelly told me about it.

So I read a lot, mostly fiction for fun, but I read just like I read constantly. And so I've read many, many nonfiction books. There's two books that made such a huge impression on me that I'll never forget them. One is Guns, Germs and Steel, which was I think was published in the early 90s. Incredible book about how humans form teams. And, you know, if we were all the same color, we'd find something to hate about each other.

It explains sports team loyalty. And it's just really interesting. The fourth turning is another one that's a little bit sad, but it seems to be very accurate. And the book was published in 97, 98, I think. And then just recently, I think one of the authors passed away, but just recently the other author did an update to it. And you can just read the update.

It goes back through the first book as well. But the idea is that especially in U .S. history, but they claim this maps to Chinese history, which is ancient Roman, British, etc., is that you have these crises that come up every roughly 80 years. And the U .S., for example, either gets through it or doesn't. And so our Civil War, I'm sorry, our Revolutionary War, our Civil War, World War II, and now we're kind of overdue.

And the argument, there's two parts to the argument. One is why does this happen, and two, what can we expect to happen? The why of it is, and I just urge people to read the summary on Wikipedia or have your AI do it for you, but you have a generation of people who are leading the country who are weak is the only real word to describe it.

They're also generally pretty rich. Like, they live a pretty happy life, and they tend to screw things up. And that leads to, say, World War II. And then you have the generation, you know, they win because of the newest generation, the people who are 18 to 20 at the time, go out and fight that war. And then, you know, that generation does extremely well and helps to rebuild the country.

And then they have kids who are utter screw -ups. And that would be our boomer generation. And then they have kids who are, in my case, generation X, right? I was born in 1970. And we're the people, theoretically, in World War II who are like the generals. So we're a good generation. And then it's the millennials are utterly terrible, but then, you know, their children fight, you know, the next war.

And, you know, is there some truth to that? I mean, we've all seen the good times make weak men, et cetera. That's a circular meme. But it does seem, yeah, but it does seem like we're in a very troubling spot right now. And, you know, a lot of people thought it would be the rise of China would trigger things or our debt spiral. AI is suddenly looking like a real contender here.

But they argue that, you know, sometime in the next decade, we're going to have real troubles on our hand. And we as a country, we as a world, and we're going to have to get through it. And we may not. But if we do, we come out much stronger. What do you think is the, like, the book breaks into these 20 -year segments? Yeah. And the last segment, I think, is when the crisis happens? Yeah.

Do you think the crisis is, is it back to the 08 bubble? Is it COVID? Is it AI? Like, those all feel like 10 years apart. I feel like we should record, like, four different segments of this answer. And then you guys later put in the one that's right. Like, we just don't know. I don't know if in 1930, if they had read this book, they would have thought that the, you know, the 1929 crash and depression was that.

They're all interrelated, of course, right? That obviously led to Germany rearming, et cetera. So I don't know. But financial crash, going back to 9 -11, we just hit the 25th anniversary. The world changed dramatically from there. The U .S. flexed its muscles militarily. And, you know, the results were not great. The financial crisis, our debt is unpayable.

We all know that. We just don't know when it, you know. Shit, it's a fan. And then AI is terrifying and awesome. So I don't know. It's hard for me to figure out what would be more impactful in hindsight, either crypto or AI, if we look back at the... Crypto is not as revolutionary as AI, is my belief. I could be wrong, but yeah. Why would that cause such a destabilizing 100 -year event? AI.

Yeah, like everyone talks about, like, the prosperity that would come from it. The solving medicine, new technologies, traveling stars. A new species that is smarter than us. You can't even imagine how that could go wrong? Well, I can, but there's so many counterbalances. Like, there's so many benefits to it. I mean, we're using AI extensively in war right now, right? Yeah, definitely.

And the Chinese are pretty good at it, right? I mean, you know. It's crazy that we're getting freedom and open source on AI from China, though. Crazy. It's nuts. It's amazing, actually. I love it. But yeah. Yeah. Curious what you think. Well, I think it's fantastic. I do think, though, that we need to... Look, China's not in an awesome position right now.

There are lots of things wrong with China right now. And to see the fall of the party and the rise of the people, hopefully in a non -war way, would be really awesome. See, I don't know that as a dumb American. I just assume China's crushing it. Robotics. I mean, you've seen the ghost cities. You know, they put so much emphasis on GDP and they build a city.

That's all new GDP. But the debt issue in China is pretty bad as well. And the people there, you know, they wanted to get their money out of China. China, there's capital controls. They still got out a lot, thanks to crypto. But then they got into real estate and they thought that was going to save them. And it turned out it didn't. And so you have a population.

You know, generally you don't have revolutions. I'm speaking as a novice. But like, you don't see revolutions happen until people are starving, basically. Usually. People aren't starving in China yet, but they do import a lot of food. They have to import all their energy. All kinds of problems with China. Interesting. And so I'm trying to tie in like what we're seeing with AI with the fourth turning to like try to understand like cause and effect here.

Like in the US, we have hyper centralization, max safety, doomerism, anthropic and opening. I want regulatory capture. China is giving us free open source. I think they're innovating way more than people give them credit for. Oh, they're coming second and they have a lot of benefits to coming second on this. For sure. Yeah. But. Mote building and AI seems to be a difficult thing to do.

Like the model layer, like the heavy infra. Yeah. Yeah. So I'm trying to figure out how this plays out. I don't know how it plays out, but it's going to be really interesting. Also, it'd be a really good idea to own some physical gold and Bitcoin while we watch. Stay mobile, collect passports. You know, things like that. So. Why, why, why Bitcoin with, with AI? Like max money printing UBI happens or just.

Sorry. Your question is why Bitcoin with an AI threat? Yeah. Yeah. Like why on Bitcoin given the right. It's hard money. It's, it is the only true form of money. It's a beautiful God given thing. Like I like to think of Bitcoin as being discovered, not invented. I like that. It was invented, but like it was inevitable that something like that would have to happen.

Just like the internet was inevitable. Um, so, uh, you know, if you're in the U S by gun. Can I ask like maybe going back to the AI stuff? I know it's newsy, but it's kind of could be timeless. Like, I'm curious, like what your ideal scenario would be to what's going on with AI. Like, do you want Dario and Sam Altman to like run a foundation, which decides the rate of progress? Like, what do you, what do you.

No, no, that's just regulatory capture. I mean, it's, it's, it is, you know what I mean by that. It's clearly what it is, you know, getting to a poor position and asking me to be regulated means you'll never have any other competition.

Uh, the ideal scenario is, um, uh, what do they call it? Like in Dubai and, uh, the benevolent dictator. Yeah. Uh, that, you know, it, it loves us and cares for us. Like we do with the animals in our zoos.

There's no way to keep it under control. Wait, the medieval dictator is AGI. I think that's our best hope is that it, it, they, that it loves us and cares for us and defends us. Um, not that it sees us as unnecessary and just doesn't care about us, lets us die out, anything like that. But, you know, these are, these are big questions that like can't be answered right now, at least by me.

Um, but yeah, I'm, I'm both terrified and excited by it. The hard part is like, I want AGI to love us too. Yeah. And if you talk to people, that's the safety argument. And then you become an effective altruist and then you. Oh, don't say that word. I hate it. I don't want to. Yeah. It's SPF. Yeah. But, but that inevitably case you, it's gross.

It just feels dirty. I feel like I'm being talked down to by an academic when I hear it. Yeah. But yeah, I'm just curious, like where it, where it shakes out. I don't know. Fucking no, man. Like get an AI guy on here. But like it's, uh, you guys started doing a lot of AI investments. Yeah. Yeah. It's funny. There's like two kinds of crypto funds.

Now the ones that are allowed to invest in other things and the ones that aren't. We started a couple of years ago though. Yeah. We're, we're lucky that we can invest in whatever we want. Uh, and we have branched out into AI at first, sort of calling it crypto adjacent. Um, and then, you know, from there we just invest in AI and our LPs are perfectly fine with it.

I mean, there's a lot of similarities between crypto and open source AI. Okay. But not many with. I just think crypto is a, is a very convenient way for AI to conduct financial transactions. Like it's the least friction option for an AI agent to transact money. Yeah. It's almost made for AI, right? I mean, beyond transacting money, do you think there's like some bigger story around AGI existing or evolving on chain or like living on chain or anything like that? Or no.

Why does it need to be on chain? I guess it's like the next step between your idea and frictionless commerce.

Okay. Explain to me how a ledger holds AI. Like actually explain that to me, what you mean by that. I think. Like there's AI, it's a thing. And then there's crypto, which is, you know, generally seen as a payments platform. I think this is really hard to figure out right now. But if you did have a model and the weights were not messed with and it wasn't censored by, you know, a company and it persisted around the world, it's a very similar concept to Bitcoin.

And you could ping that and inference against it. So you mean it's inherently auditable? Is that what you mean? Yeah, for sure. Yeah. Totally transparent. Super cool. Yeah. Yeah. We could. We'll see where it goes. God, it must be hard to be your age. And even harder to be much younger. Like, it's like, but like, you know, the world's either going to end or it's going to be a utopia in a good sense.

It's got to be terrifying. I met with, I had an anthropic guy over my house last night. We were chatting, eating dinner and stuff. And he's like, yeah, I'm just enjoying my last six months. And I was like, brother, come on. Like his poor girlfriend's sitting there like wanting to have kids and stuff. And I'm like, you can't say. Yeah. He was joking, I hope.

Right. No, no, he wasn't. What? No, he wasn't at all. Let's talk about this. Who is this? He's an anthropic researcher. He's a buddy, but. And he legitimately thinks that we have six months. Not just him. Legitimately most people. Yeah. I've seen this stuff, but I've never talked to an actual person that worked at one of these places. Say that to me private.

He's the only one that I've like in person talked to. And the idea is like, of course, if he personally could stop it, he probably would. Is that the, I mean, if he doesn't want the world to end in six months. Well, that's the. But he can't stop. That's the stupid part. Like you go to Dario Ananthropic and you say, if that's inevitable, shut the company down.

Yeah. But that doesn't, that doesn't stop anything. Yeah. Because China keeps going. Well, open AI would keep going. But yes, China would for sure keep going. And so we're in a catch 22 position where we have to push it forward. And we don't know what happens when we get there. I don't, I don't, I agree. I don't think any US lab can slow down AI because China will lap us.

They'll win AGI and they win. Not only can they not, they won't. They just won't. They talk a lot about stopping. Yeah. It's regulatory capture. Yeah. And the red cap goes back a couple of years. Like Sam's been at Congress multiple times. Yeah. Like they're all crying wolf. I've known Sam a long time. I met Sam in my tech crunch days and he had a startup Sequoia backed and he sold it.

And then I knew him when he took over Y Combinator. I've known Sam a long time. He's a very smart man. There's that video of him wearing the purple polo or something on stage, pitching that company. I forgot the name of it. I forgot the name of it too. But it ultimately was, he made money for his investors, but the tech was thrown away. But he's an exceptional sales person.

He has exceptional charisma. Do you think he's evil?

He's evil. I believe he's a psychopath. So. Which is different than being evil. Why is it different? Well, a psychopath is a medical condition, right? Uh, it's something that, that happens to you and you can't help. And there are plenty of psychopaths, you know, that aren't evil. I mean, Dexter, who's a fictional character, but. What a show.

Do you even know what Dexter is? What a show. Yeah. Loved it. Um, yeah. A friend of mine hadn't seen it within the last few days. And I'm like, oh, you have such a treat to watch that show for the first time. Um, uh, and also I'm not a psychiatrist, so I can't really diagnose anybody. But, um. Well, how do you like, uh, how do you know, like, what was the feeling that led you to identify him as like a psychopath? And I asked this because I'm going to ask you.

Yeah. We do a lot of work at Arrington Capital around, um, psychology. And there's a company, it's called Pathwise. It's actually a pretty small company. They're based in Seattle. Um, and we put all of our partners through their program. The program is a one -year program. You meet, I think, four -ish hours. I've done it so long ago now. You meet like four hours a month for a year.

Uh, in a group. And you go through basic, uh, Jungian and Freudian, like, personality types. And, um, the idea is to allow you to, well, my friend who recommended it to me calls it weaponized psychology because it gives you, uh, certain advantages in some circumstances. They don't describe it that way. It's just, you know, try to understand who you're dealing with because your input to them, the output you get will change dramatically based on the type of person you are.

Uh, and so there are certain things. And especially somebody you've known a long time. Uh, the easiest way though, with a psychopath is just the, literally when you're in their presence, like the hairs in the back of your neck stick up. So you don't really know why you just know they're not right.

You, again, I probably misdiagnose all the time, but I find it highly effective in first meetings, um, in determining how to act towards somebody. Cause there's a lot of psychopaths and narcissists in our, in our industry and our industry, meaning tech in general. Uh, and it's useful to know one from the other. Yeah. Maybe like a dumb question, but you, do you have, I'm assuming you want to meet your founders in person that you invest in.

Like, can you get that through a video call? Absolutely. You can. Absolutely. Yeah. God, how many of your founders do you meet in person before investing? Not a lot. Yeah. But I try to make it a point, but we don't. It's hard. It's too slow. Yeah. Yeah.

So, um, I mean, we could talk about it now if you want or. No, sure. Um, okay. So let's say I'm meeting you for the first time and you're pitching me your company and, um, you start name dropping a lot. Uh, and you know, that happens, you know, sometimes you have a pitch with a company and they introduce themselves and it's 10, 15 minutes.

You've seen that, right? And it's like, and then in kindergarten, I, um, that's a basic level of insecurity that points towards narcissism. Narcissism is fantastic because these are people who are feeling very empty inside and a need to prove themselves to whoever they'll work their butts off for you. You just have to be able to handle them.

Um, you have to be able to compliment them and realize they can't take any kind of criticism, which is very true. Um, and of course, never criticize them in a, in a non -private setting, you know, things like that. Narcissists agree. Probably half the people we invest in are narcissists. I don't think any other venture fund would admit that.

Fundamentally we're all broken by the way. Uh, but fundamentally broken in a way that gives them the, the intense desire to succeed. What's not to like about that? I, nothing. Yeah. I mean, we have a very similar, like my partner, Jose led what we call our founder Northstar and we look at founders. It's, you know, do they have a chip on their shoulder? Yeah.

Have they seen greatness? Yeah. Uh, you know, are they trying to prove something to the world? Yeah. All those traits and you can't really fake it. I mean, you could survive an earthquake. That doesn't make you a great founder. Like there needs to be more. Yeah. Like surviving isn't enough, but yeah, I don't think I've ever looked at it from a narcissist point of view.

Also, I'm not talking about narcissistic personality disorder. I mean that you need psychiatric help. I'm just talking about people tend towards one of the seven personality types and that's my belief. And, uh, you know, they're a little narcissistic. That's not a terrible. You mentioned 50% of the founders are, I mean, a lot of narcissists and a lot of psychopaths and a lot of schizoids that really, you know, is that the other 50? I don't know if it's 50.

Look, narcissists are like a small percentage of the population, but a much higher percentage in our, what's the schizoid? Uh, it's somebody who, uh, well, it's somebody who's schizophrenic. You've heard that term, multiple personalities, you know, sees things, hears things. Uh, but somebody who's schizoid is, um, not like that. Of course, they just live a very rich inner life.

It takes a long time for them to like you. And, but once they do, they're loyal forever. I've had business partners who were schizoids in the past. I have them now. They're the best. Um, the, you know, if you talk about like Mark Zuckerberg, who I've known for a long time, like people call him a lizard person or whatever. Um, and they think baby psychopath, but I get schizoid vibes from him.

And, um, he has a really good PR team now though. He seems human. Well, he's, he's working out. He looks like awesome. I know. Yeah. Years ago, he looked weird. Like he was, I mean, we all look a little weird, but yeah. Um,

I don't know why I needed to defend Zuckerberg in there. He's well, then the fact that I said he looks human now implies, I also thought he was a lizard person back. Look, he was a little, he was an oddball, but like, you know, a lot of like, you know, I don't know if you've ever seen Bill Gates when he was, you know, like at Harvard, you know, he was pretty freaky.

Yeah. So what are the personality types you don't invest in? The ones that, cause I try to avoid psychopaths, like at all costs. So we actually had a psychopath working for us once. What? Yeah. Uh, how long until you found out huge overachiever pretty quickly actually let him go eventually because of some sexual harassment stuff with somebody else on the team.

But funny thing is when he left, um, cause he was fired, he showed up a few months later, maybe six months later as a partner at a, another fund.

And he had, uh, he had told that fund he was a partner with Arrington capital. And, you know, I, we don't have a lot on our website for security purposes. We don't want to like blast everyone's name out there. So it was hard to tell. Now I knew the guy who founded the fund. He could have called me. He just did. Uh, and, uh, he got fired. The whole fund got shut down actually.

Um, but you know, this guy was like super charming, super handsome, very smart. And he just had this flaw that meant he could never achieve what he wanted to because he was so over the top, like psychopathic that like people could sense it. Did, I mean, not to put you on a spot, but like what did he go through the study and you found out or like, how did he get past like the gates that you guys have when we hired him? Yeah.

I mean, we hired him as like a summer intern and it like made him into like a something else that was more permanent. Okay. He was, you know, very junior guy, but, uh, I frankly didn't pay a ton of attention at first, but when I started to get to know him, I, I realized I was scared, scared of that guy. Like genuinely scared of him. Yeah.

I think it's just so hard. I mean, you have like muscle memory or you have like a refined taste. Like, I feel like it's very hard to tell the difference between a psychopath and an arsonist. Like they want to take over the world. They overachieve. It is genuinely hard to tell, but there are some tells psychopaths, uh, you know, psychopaths mimic normal behavior.

They taught themselves to be normal because they, they don't feel empathy, uh, let alone sympathy there. You know, they just don't, they don't have feelings that other people have and they don't actually, supposedly, they don't actually feel empty because of that. They just feel different. And so then they realized that they creep people out, you know, and so they learned fake it to the point where they become excellent at it.

And quite often they fake being narcissist. Um, and it's hard to tell, but you can tell if you like study this and really think about it and go through it. I feel like I could tell really quickly and connect the dots over longer periods of time, which obviously easier because they'll, they'll slightly wrong you in a lot of small things and it'll start to add up.

And that's for sure. That's usually how I catch it. And I've made mistakes and we have invested in psychopaths, but, um,

uh, including when we're not going to mention the company here, but including when we were talking about a little earlier before we started rolling. Um, but, um, you know, it just helps if you can weed some of them out. I'd love to see fund like returns for the portfolio companies within your fund based on the personality type of. Oh, we track that.

Yeah. We track. That's cool. Yeah. Is it pretty markedly. Yeah. Narcissists rock. Man. Yeah. They, they, they're, uh, they're terror on their like husbands, wives, partners, whatever. Like it sucks. They're rough with their children. They tend to make new narcissists, but yeah. Hire them. Fantastic. People like that. Yeah. And the team knows to like, yeah, it's just, it's just awesome that you're so focused on this founder psychology.

Yeah. So it's mostly to weed people out, uh, you know, and you still have to have a good idea and a good team, of course, but it's very important for us. Yeah. And it served us well. Is this like the start of the fund you did this or was this something you learned and implemented later? I took this class, I think in 2016 or 17. So I had used it and then, you know, I started putting the partners through it pretty early on.

Yeah. All of our partners have been through it. So it's interesting. I do understand the weapon. I like, if you talk to an AI model today, like open AI or Anthropic, if you put somebody's personality in there, like it won't give you advice on how to really effectively target them because it views it as like weaponization, like what you said, like, I don't know.

I, the, the really funny thing with this is after I took the class, I had a meeting with the coach, founder of the company and we were sitting in a cafe in Seattle and I, his name is Chad and Chad is a admitted narcissist.

Um, and we were sitting there talking and I go, you know, I just got so much out of the class, uh, really like changed my life. And Chad, like, you're so awesome. And like, and like, I don't think anybody could have taught me like you did. He starts like puffing up a little bit. And I go, and you're like, you're like, it's not important, but like, you're also just like really handsome guy and he, and I look at him and I go, gotcha.

And he goes, he goes, he goes, fuck. He goes, okay. I taught you pretty well. Um, and if you compliment narcissists, they love it and they love you. If you compliment a psychopath inside, forgetting what they show you, they think, oh, this is a weak person. And so with a psychopath, you actually need to make yourself physically threatening, not touch them, but like, get up, get big, don't compliment them.

And they will respect that and respond in a way that's better. Now that's more when you're negotiating a business deal and you don't have the opportunity to just walk away. Um, but that's the, those simple rules, like, and if you compliment a psychopath, they're not going to react the same way as a narcissist. So that's another tell. So this is so interesting.

It is super fascinating. Yeah. And just how broken we all are. So I'm parent. Uh, I have a paranoid personality and that has served me well in being a journalist back in the day. Uh, that's definitely a superpower for being a journalist. Yeah. It's not so great in interpersonal relationships where you're constantly like thinking ahead and what's going wrong and what the real motivations are, but it can do well in business.

Yeah. A lot of false positives though. So you can, you gotta be able to question yourself on something. Can we talk early tech crunch days? I'd love to. Yeah. So like the Genesis of tech crunch is so interesting to me. You're in the first Y Combinator meeting, like story, the funder and accelerator. I don't know that. It's an accelerator, but at the time it wasn't anything.

It was just some dude named Paul in Mountain View who was like, had some startups come in and he guided them. Like it was like just another thing, but it was like 20, 25 new startups I could go and cover in one day. Did he take the 7% early on? I don't, I don't know if it was seven early on. Okay. So you're in, so like walk me through it.

Like Paul invites you or you just shoot, you kind of show up and you see all these startups and you're like. I could have to look through my emails, but I don't know if Paul invited me or I heard about it and just came. Um, I think I started the second one. I think there was a first one that like nobody was at when I went, there were like not very many people in the audience and I was the only press and I had my laptop open and I was typing away and blogging real time.

So you were pressed before YC? Yeah. I started TechCrunch in 05. Okay. And you know, YC came a little bit after that. Yeah. Okay. So before YC you were covering just normal tech breaking news. Yeah. I, so I was sitting, I was in an apartment on the strand, which means on the beach in Manhattan beach. I had a girlfriend. She had a job. I'd quit my job.

I spent a year just surfing and playing video games and eating, eating a burritos. It was fantastic. And, um, it's crazy. Cause you're so successful. Like I can't imagine you taking a year off just to had a rough couple of years. If I had started my own company, I sold it, doubled investor money. Didn't make any money myself because of. That's the one with the one X breath.

You didn't. Yeah. It was two X liquidation preference back then. So sold it for 35 million, but we, we had, um, taken 17 and a half million in investment. So you literally made nothing. No, I got 150 grand. They, they had to pay us something to not veto it. Um, and so I bought a Porsche Boxster. Yeah. But then I moved to England and I sat in a garage for 10 years.

But, uh, so I was sitting there and I was like, all right, I need a job. Um, but I'd realized I had gotten out of tech for a little bit. Like I, I had taken a little bit of time off and things were moving very quickly. The read, write web was becoming a thing instead of static webpages, these webpages you could also interact with and like create content like Google doc.

Right. Um, so I started researching and in my research, I found it was like very few places to find information about these startups.

And so I decided, you know, I'm going to start a blog. Blogs were cool back then. And I'm just going to post my research. And so the first few articles on tech crunch, which I think are still there, were just like very formatted, you know, company name, you know, product description, fundraising to date and journalistic edge. No, no opinion.

I didn't know what I was doing. Uh, but back then everybody had a, like a Google search on themselves, right? I forgot what it was called. Like, you know, you get a notification, an email, if you know, there was a search, if a document popped up with your name on it or your company's name, everybody had them back then. And so these, these founders would start getting, they didn't know who I was.

I had four readers, but they'd start getting these Google notifications. And then they'd come and they'd comment and they'd send it to all their friends and their mom. So it was the mom, you know, look, I got some press. And so suddenly like all these, these people who started companies that could get no press before that, nobody would cover them until they got really big, like latched onto me as, as like a life buoy, like a way to like, you know, grow and be able to hire new people and like all that.

And so I accidentally just struck oil with that. Did you build that alert I'm sorry, just double click on that, like the alert system where people would get auto -tagged when they You could probably still do this on Google, I don't know, but you'd go to Google and there was a way to set up a notification if Google found a document that that word was Did you know that going into tech? Everybody knew that back then But like you knowingly No Twitter, no social media It's just such a great way to hunt And so if somebody mentioned you, you'd learn about it that way So then two years go by and you're in YC Well, so the tech crunch just kind of hummed along, but then in the next

year in 06, I broke the story of Google buying YouTube and I had the price And I had it like four days before it was announced and everybody laughed at me Like the Wall Street Journal was like this, who is this guy? Like this didn't happen and then it was true So is this like a one -off good tip or is this like demonstrating? You know deep you are like, yeah I never said how I got the tip, but it was a buddy of mine Who had been funded by sequoia And the sequoia partner had told him Boasting And he called me i've literally never told this story He called me and so I wrote it and I was right and uh Then that was sort of the era of me breaking big stories and so I started

like people started coming to me with information I broke a lot of big stories so it sounds like tech crunch flipped from You going out and finding it versus people coming to you in 06. Yeah I rented a house in silicon valley and I started having barbecues at my house These things got famous police would shut them down Um hundreds of people Uh would come Damn Yeah, it was fun.

I'm also super introverted and not a narcissist And so for me I would end up like retreating into my office because the company was run out of my house Um, but people love being to those parties. So, um that built a whole community as well So, so then so then you know seven though you you flip again and now you start doing the work You're going out I finding founders I mean, I always did that there I have meetups at my house founders would come but um

You know It wasn't like me going to y combinator that first time was like this major story that I was gonna yeah These were like no name startups who knows if they're all gonna fail. I didn't really know who paul was Um, I did it because that's what I did like I if there was a startup I covered it if you had a startup I was gonna cover it at least those first few years because It was still pretty slow after the nuclear winter of the 2000 crash.

So did you cover things negatively as well? um Yes, but for the most part no for the most part I was on the founder's side and gave them the benefit of the doubt I got a lot of pushback from real journalists that um would constantly criticize me over that and it caused me a lot of stress I love how you say real journalists, but you're the one that built that crunch Yeah, they um Um and journalism has changed now where that's considered normal to like have an opinion but at the time it wasn't and uh I was just unabashedly pro -founder they were They were my rock stars like I didn't care.

I don't really care about celebrities but like steve jobs Who is a mentor of mine? I spent decent amount of time with him in the late 90s When he was at next before he sold it back to apple Just because I was one of his lawyers But like these are the people who like when I first met steve jobs He walked into a room. I had a styrofoam cup of coffee in my hand and I poured it all over myself like a total like fucking idiot and like it was like I met some famous person and uh and uh, so many rabbit holes here.

I genuinely love entrepreneurs I I I so many rabbit holes now now i'm going off off but like what was the Most interesting stuff with steve like those are early days 90s. No, yeah, yeah, that's not oh I had a So we represented him when he sold next uh to apple And this is a big deal in like, uh, the late 90s because it brought steve jobs back to apple Got it.

That was okay. So he's back to apple And he owned he had next in pixar pixar was sold later, but uh, he went back to apple. So um, we negotiated that deal as his lawyers not as his bank But so we thought we were super cool because we are the lawyers, but the bankers did all the real work, but um, you know, I I was fairly junior and so I went to his house a couple times to get signatures He talked sit down and talk to me Uh He's just a super cool dude No, I mean he was he was a bit crazy, but I never saw that like he was very charming um and uh I wanted to be just like him when I grew up Did you learn anything specifically from steve that you think's like yeah, you'll life

lesson? Yeah, don't be a lawyer like Be out there built like I was like In silicon I was at the law firm in silicon valley, you know mark andreason I first met him at netscape then um And all these guys that were super cool, but we were the lawyers and we thought we were cool because we were the lawyers And I worked on the apple next deal, but I wasn't cool.

Steve jobs is cool, right? And so I I said I gotta get out of here I gotta stop being a lawyer and go start a company. So I did uh, and he He's one of the people that taught me that as well as andreason So back when andreason had hair So steve kind of taught you indirectly No, like I sat in his house and he talked to me about how much he hates lawyers

The other cool thing is after the transaction closed the main partner on the deal was on vacation And so he had told steve if you need anything call mike And so I have this voicemail because I missed his call. Thank god And the voicemail said, uh, I think attorney client privilege is lapsed now Everybody's pretty much passed away with me, but he said, uh, he got a bunch of apple stock In the in the in the merger and he left me a voicemail saying I want to sell it all And he did he sold all of his apple stock and so I had to then call the bankers and figure out how to do it I kept that voicemail for like 10 years before I lost it What the hell did he sell like it had to

have been he did not he I forgot what it was like at the time he like Wasn't super into apple. I was he I guess he was a ceo. He wasn't the ceo right away I don't know, but he was still a little bitter about apple because he was treated very badly in the 80s. Yeah So, um, I mean he passed away as a definitely a multi -billionaire before Tim cook 10x to four trails So it was 400 bill or something when he probably passed something like that He had a lot of money any of that that yacht he built I've been on that yacht Not with him, but uh, his wife, you know, I don't think he ever stepped foot on it, but his wife Took it over and now she's she at least for a time spent a lot

of time on it with her trainer and I just thought He was so pissed

Was steve alive while the boat was around or did it finish? I don't think it was finished before he died. I don't know for sure It's a sweet boat. You should look at the picture. It's very modern even now, but uh, it's kind of crazy to be on a yacht with your your dead husband's yacht with your boyfriend, but Yeah, people are nuts That is yeah Um, so back to tech crunch days oh seven y combinator you're starting to break huge stories Yeah about founders Like yeah, I want to know like I I don't really I want to know like about how you operated those days Like was it easy? Was it hard was early tech crunch days easy hours like the higher people? I gained so much weight.

I worked So i'm i'm like turns out i'm hyper competitive So I didn't love the work because it's hard to write like let's say I was writing about some startup And it was not some simple startup There were you know, I used to call them mufflers like all the foundational sort of infrastructure stuff because I hated it And I didn't understand it if I was going to write a story There's a way to cheat and journalists do it all the time where they kind of write a story But they don't understand the product And it the story is written right, but you Don't really learn anything like I needed to understand the product and explain it away so that I could talk to people in it And so

I had to actually learn stuff and that I insisted on it and so a lot of work went into writing and um And you know stuff would happen all night if I hated the idea of going to sleep and missing a breaking story And so my sleep got really bad I'd work all night i'd go to sleep at dawn that when the bird started chirping it would like make me go to sleep um sleep a little bit my health was terrible uh but I was winning like I dominated for a few years and uh to the point where I could joke around like I loved april fool's day and one year I had like these infamous posts but one year I was at a conference speaking on april fool's and I don't even know what I was talking

about but I said hey, I gotta get going There is possibly the biggest story of my life and i'm gonna break it It's bigger than anything i've ever written about and i'm gonna break it and I left There's a lot of press there and I went back to the office and I hit publish on a story that said google goes nuclear And the first part of the story was that they were buying Uh or building a nuclear plant to power their data centers it read normal Then it got into they needed a nuclear deterrent against google or against china that kept hacking them None of the press read passed the first line and so wall street journal everybody Within a minute had reposted That google is going

nuclear and so then I started screenshotting everything and adding it as updates to the post and um Pretty soon they figured it out because somebody read it and like the wall street journal editor was like Why the fuck are we saying google google's building nuclear weapons? So I had that kind of power for a while and I didn't use it responsibly Um And it was a lot of fun Yeah

What was what was another irresponsible use of the brand? I don't know if it's irresponsible though. It's driving views to tech crunch like you could argue Oh, I um

There's other april fool stuff, but like there was a time when you remember do you don't even know what zynga is? Oh, yeah They had this kind of forgetting now But like they had this like weird ad product that was super lame and it was powered by this other company I forgot what it was doing wrong But I stood up at a conference where the woman the ceo of the company was speaking and i'm like hey, can you address this? Like accusation blah blah blah I remember watching your youtube video on it.

You're standing up in a crowd and you're saying a video. Yeah, and she's like it's shit It's double shit. It's not true. Anyway, it was true. She got fired and so You know, I felt very righteous about that right god You know, I don't remember what you did wrong, but I felt very righteous about that. Um Self -righteous about that But yeah, it was it was fun for a time.

It also was slowly killing me. Um, so I It was actually like I didn't start it as a business I'd started two or three companies before that that didn't work out for one reason or another This was just a hobby and then it was the first actual money I made when I sold it so what was the I feel like the burning out and the sale is never perfectly timed or was it? Like did you get to a point where you're like hell? I kind of want to Actually sell this and i'm burnt out or was it how did you Did you say your health was going downhill? Yeah, I was pretty burned out.

Um and uh and then, um Brad garlinghouse Who's the ceo of ripple He had become a pretty good friend of mine at that point. He was he was a yahoo executive and they went to aol And he's like We'd love we'd love to buy tech crunch And so he kind of shepherded it through and it was one of the first things he did for me that like set me off of my career I owe a lot to him And it was just it was just time I was you know 300 plus pounds Couldn't sleep.

I had sleep apnea. You're not 300 pounds now. No, I weigh a little less, uh, but I was so competitive that it nothing else matter besides Working and it was rough, but how do you I don't understand how you turn it off that like how do you I sold the company and then I started a venture fund Fair which it will back they were the they were the back they were the the main backer and then I had sequoia and uh, not andresen.

They weren't really doing anything yet, but uh, this is pre -credited funds. This is just yeah It was like 2010 or 11 Um, it was approved by the board. They bought pariana huffington's uh, the huffington post by then and and I somehow she was my boss And um, but I wouldn't take her calls because she was annoying. Um And I had an earn out for about I don't know 10% of the money they owed me Anyway, she had approved it But then I announced the fund on tech crunch and everyone went apeshit because I was both like a power broker at tech crunch and an investor and Ariana didn't like the press.

So she fired me on like a tweet which Immediately Aol came out said you're not fired and I'm like yeah, but you just my boss just fired me publicly so uh, they had to pay me, uh, like an extra I don't 5 million bucks like instantly and uh, so they regretted that but it feels like the yeah, the newer generation would understand like semi analysis being a comp like Big research they don't understand what like semi analysis being a comp to what you did Like big research firm now starting a fund.

Yeah. Yeah, but uh, yeah, so then I was free and then, um, I Got even fatter somehow

Hey look, you can look up like pictures of me and you'll see me I was a big fat fucker and uh Uh It really only stopped when my doctor said I was pre -diabetic and I said no No, no, no, no She's like we're gonna start putting you on the drugs. I'm like, no, we're not doing any of that I took a year off and got fit Um, but I feel like not fit mike is the successful mike but obviously it's not healthy but It what wait what are you saying about current mike and his level of success? Well, no now you're just escape velocity, but I uh

I uh I don't know, but I uh, I feel a lot better now. Nice. Yeah So you so the fund is never gonna let you I'm never gonna forgive you for that. See I think you did a bad way Yeah, that makes it worse

Apologize Fat mike was a successful mine I didn't say like with that kind of tone though. It was like genuinely I will watch the tape later But you know, it is what it is, right? So you leave the fun. I can't I can't

Cut Mike's gonna kill me So you so you leave the fund is done ariana you get paid No, the fun is great. Oh the fun kept going They had already I we did three funds. Yeah, it was crunch fund. We did three funds and uh, uh, I just didn't work for aol anymore so and crunch fund was like Sourcing founders from tecra like that was the angle or I still had every relationship I had so I you know right away We invested in uber.

I was actually uber Travis Kalanick and I Were driving from like san francisco to like somewhere down in the south bay on 280 And he was telling me about He had done a couple startups. He was telling me about The three startup ideas he had and one of them was uber and uh, garrett camp Had Suggested he started I think he had started at that point, but he wasn't the ceo and he told me about the other two And he really liked one of the other two i'm like, you know that uber thing.

That's amazing I'm, like like like you can now use an app like other people could like use their own cars and do this and he's like Well, yeah, but anyway, he and i'm not saying it's because of me But like he ended up firing the ceo and taking it over And you know, it like I was writing about it and nobody thought it was interesting until they did and So he let me invest right away in uber very early at that point um and airbnb same thing uh pinterest a few others, but That first fund was crazy because I knew all these people and they were my friends because I'd written positively about them for a long time You say a few others so like casually but those are like

generational winning companies like They're ridiculously successful investments. It was stupid. Yeah, it was stupid money But like when I put money in I I uber I had a feeling but airbnb I was like i'm gonna do it but I wasn't a hundred percent sure it was gonna hit but I put like a hundred grand in and that turned into a fuck ton of money for our lps um so it was super It was super great Yeah, but then as the years went by and we did our second and third fund but these were very small funds They were all about 30 million.

So they weren't big even then um but I and the reason they were big is I really like the earliest stages of startup I hate it when you have to look at a spreadsheet heat it um, I agree it started like I started just getting a little bored like, you know, I take the meetings Just like I had done at tech rents. I'm meeting people and then instead of writing about them i'm writing a check but I just felt like

same Shit over and over and I I don't understand like these people like reed hoffman famous investor founded linkedin He's gonna keep investing. He's got more money than he can count, but he keeps doing it And I know I speaking for him. I don't know but like I assume he's also kind of bored of this shit But like these people never stopped doing it And I think it's because they they're afraid of reinventing themselves and failing and I love reinventing myself And so kind of at the height of investing in non -ai is when I said I don't want to do this And I wanted to learn about ai which was you know, this is in like early 2017 I had invested in coinbase and I had bought

bitcoin But that's it by that point and then in 2017. I was like this is amazing and I don't know anything about it So I can learn stuff again How did you find like how did you find coinbase and bitcoin in 17 though? Like what was the I was tech crunch tech crunch. I saw these guys all the time everywhere. Yeah, like I just knew all so Yeah, maybe one question though like the second and third funds of the second and third crunch funds were you still like In the mix with founders tech crunch wise like writing about them going to the parties or was it different like it was when The second and third funds because the first fund no tech they wouldn't even allow me in the

office Okay, yeah, yeah, yeah I didn't know them at all because the first one sounds like you're kind of riding this Crazy social network you have yeah, the investment becomes early the second and third funds sound different in terms of like Maybe more traditional venture style funds versus they were exactly the same and had some big wins uh, but they weren't as easy as earlier on when I like just started the fund and went from tech crunch to writing checks So it's like a three -month period where like everything I wanted I got except stripe I almost got into strength And I met with the brothers and like they were gonna let me in but the round had been closed for like six

months okay, and They're like, yeah, we're gonna take we'll let it will small check like a hundred grand i'm like fuck. Yeah, and They went back and the other investors like What no absolutely not and so I didn't get in and and that really sucks I would not be here right now if I'd gotten that hundred grand check So you don't hang out with me just because you'd be richer.

I love you and I love this apartment but like no, I would be uh Doing other things there. Yeah So what was the decision tree to wake up and say in 2017? Uh full crypto no more traditional vc was that a day thing a month thing? What was the like all great stories? It's a woman and she's explaining all this bullshit about, you know land titles on on blockchains And i'm like, whatever, but you know, then I started paying attention to all the uh Were they called icos back then? Oh, yeah, and I was like Oh my god, so he put a little bit of money in a couple of them and like Those little bit of money became like a whole lot of money And I said i'm gonna start funder on this and

that Wow, so that was a luna was in there and some other big winners. So yeah, so that's a liquid investment But you're arrington capital is very active doing private vc deals too though. Yeah, just not lately

Just not excited with what you're seeing or what's the well a uh, we've done quite a few ai deals Uh, we've done a few crypto deals, but uh, you know normally in these down times is the best time to invest That's super true but You know, I think people just kind of gave up and we had a brain drain into ai and so we just need to get through this period a little bit I think crypto is really trying to figure out what it's gonna be at this point I think the yeah Most successful investments we ever made are always in bear markets Yeah Well, and the reason is because valuations come down and there's less there's less competition from other investors, right? um

It's super true um As someone like I mean But i've seen like a there just hasn't been a lot to look at Unless our deal flow dried up and no one else's did but like i'm looking at it. I'm like No, I mean we've we've slowed down on the crypto side and we're way more active on the ai side. It's just yeah what it's like yeah the the crazy part to me though is You've been through so many cycles Like very intimately like you've been involved in like early internet you've been involved in like three four five crypto bear markets however, we we count like you've seen three or four yeah Gotta be a lot.

I mean Yeah team 21 Recently that's three 22 not 21. Yep. It was spring of 22. Um And then this last one. Yeah You're just like you have so much context on bubbles Like I made more money in 2021 than i've made the rest of my life combined and I bet You guys did quite well Yeah, we did. Okay. Yeah, um And I just moved to florida I moved in 21 to completely unrelated to my income, but I had just moved to florida um The problem is I left so much of it in the fund I um because 22 was rough um And uh, I did of course pay my taxes Thank god and I actually overpaid my taxes by a lot by accident So that was really nice to get that back but Good times are here and you know in the

bad times like One of my partners and I won't say who but you know this person Uh recently we're going for a walk. This is maybe a couple months ago three months ago And this this person said, uh, I think crypto might be dead And i'm like that's what I was waiting for If you Have given up on crypto the bottom is reached and like I will not let this person live it down because like shortly thereafter, you know, things took off And uh, that's it you wait for everybody to think it's absolutely dead and then you just go all in I was uh, like Pretty not depressed but I don't really get depressed like pretty down a couple weeks ago Why I was just like, you know, the market

sucked and I wanted to go get out of the house Yeah, I told my wife molly i'm like, hey, i'm gonna go to this park walk around i'll be back in a couple hours And I took a bunch of pictures That day was 57k bitcoin a couple weeks ago. It's just crazy how that happened. Yeah, and I thought it was dead, too Yeah, you were dead No, I mean, I didn't think bitcoin was dead, but the venture side stuff.

You're not we're not seeing the stuff we used to see Yeah, it is what it is on the venture side, but um I just don't lose hope anymore Like the ups and downs don't don't don't affect me at all for some reason um Can I ask like not a dick question but maybe for like the listeners? Is that like because you have money now or is that like? No, no, no, no, no, actually I don't Money's not that important to me.

Uh It like really yeah, whatever every rich guy says that um, if I Go back to like my first startup when I left the law firm. I started a company This is the one I sold for 35 but didn't make any money on it I was in You know, rre ventures. I was in there Oh, I don't rate in venture firm. I was in their offices in new york and like the day the market fell It was like march or something of 2000 Right And uh, those are rough times I mean It was like tech was dead for like four years until google went public Nothing was happening There was a venture fund that returned zero dollar It was like a 200 million dollar venture fund a draper fisher jervison that like around that

time They actually managed to return zero dollars of it zero that's statistically impossible And uh, it was rough and you know, like I Did what I talked about I went to denmark and Found a girlfriend and I surfed in la every day um but We came back from that and I'll always assume we're gonna come back Unless there's nuclear war or something But knowing what you know though and being through so many cycles like you you have to wake up and make a decision Like do I spend my time on crypto or do I spend on ai? Like how do you? How do you piece that puzzle together? You know i'm 56 now I think the days of reinventing myself I mean a little bit with ai but like i'm not gonna

keep reinventing myself like right now I consider myself a steward of my firm And and mentoring my team The partners in particular not that they all need my mentoring the guy that runs our liquid fund is smarter than Everyone in this room probably you have an incredible team. I've met a lot of them. They're great and we're small But uh, I feel like i'm a steward and I do bring value to the firm Um, I won't go into why or how but like I bring in investors and I brought in a few deals Uh, you know, we're we did the spack for ever north the ripple dat which I actually think is going to be pretty cool Um, luckily they weren't public during that bad time Uh, but for the most

part like I let them do their thing and and I get a lot of joy Yeah, and I get a lot of joy out of making people rich, right? Like I Like five people became millionaires when I sold tech crunch like I care more about that than the money I made again standard thing a rich person might say but like I I I get joy to that now and so I don't know if i'm going to reinvent myself and I actually don't even think i'm addressing whatever your original question is No, you're addressing it better.

Do you like is there any like but I feel like the fundamentals of crypto are very sound I I agree. It's just the the it I don't know how to stop believing in it. I don't I don't not believe in it. I super believe in it This i'm just accusing you of that. Why would I stop believing in it when I believe in it religiously? So I just hard money is the only thing that can save us.

Yeah, no, no, I agree on that hard money that governments can't stop Right. We've had hard money in the past, but government have we seen they always debase it

Bitcoin realistically can't be stopped and that's going to save us all Yeah, no, I will they're never going to slow down spending money. We've tried elon tried like we're never gonna Absolutely cannot. Yeah, there's yeah The only way to do that is again with the benevolent dictator Somebody who doesn't answer to democracy, which you know, democracy is Two wolves.

What is it two wolves decided in a sheep deciding on what's for dinner? I mean, it's just it's just you know, democracy doesn't work Churchill said, you know, what do you say? He said democracy is Terrible

It's just better than everything else or something like it It's a real problem. And so we're never going to stop spending so do you like Being so do you prepare in a certain way like personally like you're not really involved in politics that i'm aware of or Oh, I keep my head down in politics. I'm a libertarian So my candidates will never get elected um I how do I prepare? I mean, i've got Guns and bitcoin and gold Yeah, there's two there's two theories on preparing one is, you know guns And you're done because then everyone's stuff is your stuff And the other way is, you know, you buy all the stuff, you know You freeze -dried rice or whatever the fuck people buy but um

Look, i'm not crazy even though I am paranoid. Uh But you know, I have guns i'm a God -fearing american. I believe it's our literally our duty to own a weapon safely and like responsibly Same, but I hope that it doesn't come to it. I am a little worried that every fucking billionaire. I know are we allowed to swear on this podcast? Yeah, I know we are of course listen well, but every fucking billionaire.

I know Uh, you know has a goddamn bunker somewhere And like do you have a bunker? I'm not a billionaire yet But like I know I don't I own one house the one I live in and uh I actually would love to have a bunker what i'd love is one of those retired missile silos. Yeah, it'd just be super cool Yeah, right But no, I don't have a bunker but these guys legitimately have bunkers in multiple countries and like There are the ones in charge.

Yeah, they're in charge of everything and so, you know They know what's up. Yeah I like what's the endgame they go in their bunker they come out after the nuclear war and everything's fine like the world's over It's what's the point as far as i'm concerned when they go in their bunker whoever their head of security runs the place and you know So you better be really really nice to your head of security Years before you need them, right? Yeah, because you know, they'll kill you.

It's gonna suck. Yeah If that happens. Yeah, what's your like? Do you have any advice for like the 20 year? I just sounded super crazy, didn't I no not at all? The bunkers sound crazy I mean, would you have a bunker if you could like afford it without blinking? Absolutely. So they're not crazy They're they're crazy in that they're like actively I mean, I want to say that like it's so cliche like they're actively working to destroy the world, but they're not really it's just Game theory and humans doing what we do And there's no way out of you know, we talked about with ai like yeah, let's say the us says we're going to regulate and slow down ai That's not going to do a

darn thing except make sure we lose right so It's a catch -22 these these billionaires that have the bunkers that you know, like any interesting ones that you think Oh, I only know what I read in the press No, no one has actually taken me to their bunker or like invited me into the bunker group. I

I don't know if brad has one if he does I don't know about it I feel like if they tell you it ruins the whole point I mean you want to be included in these things. Yeah, fair. You want to be part of the bunker We could group together, you know, there's enough of us here in miami We could get a bunker and just I mean if I contribute a hundred bucks and you contribute the rest we could have a great bunker Oh, I think you're doing a lot better than being able to contribute a hundred bucks, but you know, we could just uh Socialist utopia in our bunker It would be fun for a couple of weekends It might be life -saving.

I don't know but any advice to the 20 year olds facing what you see Like what do you give your what advice do you give your kids? I don't know how old your kids are No, no, I don't have kids. Uh, I have a stepdaughter. Uh, but that ended when uh Natalia my uh ex you didn't ask about the ending of that and we won't get into it, but uh No kids if I was 20 i'd be freaking the fuck out and probably just getting high every day Like I don't know, you know what I definitely would like lean towards being a plumber or something But like I I I don't know what you I don't I don't there's got to be something they could do like use ai all day By the way, you're you said 28 30 You're

okay. You're still a puppy, right? Like you're very young and I think you're gonna be okay money wise but like imagine you were a normal 32 year old and had Scary as fuck can't buy a house in your account. Like what are you gonna do? I don't know I think like the scary part for me is like they don't have an option so they like Create a really stupid socialist government like Like they have to take more out of the system, you know, uh, uh altman was talking about ubi early on um And yeah, okay, maybe I can imagine a world that elon talks about where there's you know, plenty of everything Everything's free material stuff and we can afford to do that.

Okay um But what about like, you know the fact that You know, is it half more than half of the adult population are on antidepressants now? It's because we have no purpose We're already living too well and we're not scared of anything and like we just like fester in our own minds like what's gonna happen then And I I it's scary. It's super scary ubi scares the shit out of me because I'm like such a pro Meritocracy kind of person like yeah, I don't think the person that works less than they should have more than me Like that's just my point of view I agree But what about when like, you know, like five million people in the u .s.

Starved to death? Like what are you gonna do? Right? I mean you're going to do some form of ubi We already do some form of ubi Everybody has free medical care Food stamps It's not great, but yeah, but Gosh, those people live miserable lives We're kind of closing back to the fourth turning It's I feel like we've come full circle And I remember the whole boiling frog thing like this stuff like is Coming up on us Yeah Also, nobody has ever lived in a period of technological change as abrupt as we are Right? Like it's just crazy how fast the world is changing when you know before like 19 even 40 the world changed very very slowly and so The boiling frog thing is like I I

don't think we even understand right now sitting here how bad it's gotten. And I think if you were like, took your 1995 brain, I know you probably weren't born yet, but like, and just suddenly shoved it now, I think we'd be petrified. Like bad it's gotten, like how fast it's moving? Yeah, just how like scary everything is. I mean, these Flock cameras fascinate me.

That's nuts to me. They're everywhere. They're everywhere. And it's not just Flock, there's other companies, some of which I've invested in, but which, you know, what kind of person does it make me? Those are the good ones. Yeah, I'm not so sure they are. But the the politics that we all hate each other all the time, like we didn't hate each other in the 90s.

Like Republicans and Democrats kind of got along. Not totally, but they kind of did. Now we all just hate each other all the time. And I thought I just realized politics because I was getting older. I didn't think like the world's very different than it used to be. Men and women used to go on dates and like, like each other.

I feel like the world was like pretty nice. And.

I don't know what's going on now. Again, am I just getting old? Am I just get off my lawn kind of guy now? I don't know, but I'm I'm really scared for a lot of things right now. Yeah. And the way I deal with that is not the doomerism. I try to just live life, you know, every day. And I think that that's good for anybody that over ruminates is just get out of your head and live your life.

The rumination part. I've spent a lot of time learning about because it's really hard to let like a really bad investment go or really bad, you know, something you missed a great employee. Yeah. Yeah. An event like rumination could could kill you if it's not productive. I like the show would kill you, but it would. It definitely sucks. Yeah, it's not product.

What's like for me, it was like Pema Chodron helped me a lot like on that. Like what gets you out of what I'm dating Pema Chodron, like a really great Buddhist. I love her books. She has one on getting unhooked, which is phenomenal. Taoism is actually more my style. It's very easy to look up the difference, but like it speaks to me. It definitely speaks to me.

And so I'd love to read the book. I don't know who that person I'll send you on. Yeah, it was good. But sorry. So how do you get out of ruminating now? What's your oh, I'm terrible. Yeah. But how do you like how do you focus on productive stuff? Well, I have some hobbies, you know.

I think you said you go for a run sometimes. Like I don't like running. I just go. Yeah. You know, actually, one of the things I've talked about today is like you. You know, you have a lot of entrepreneurs that listen to this and like the best skill I learned early on is like face your fears. Whatever you're scared of, attack it. And for me, it was marathons.

When I was in my first year after law school, the partner in the office near me ran marathons all the time. I didn't really even know what a marathon was and it scared the hell out of me because I'm not built for running. I ran a marathon in a couple of years. I trained for it and I ran a marathon. I hated it. My nipples bled like it was a disaster.

But I finished and I don't have to worry about that anymore. And I'm not scared of it. And I've done that. I've always like that's one of the main tenets of my life. Just whatever you're scared of, just go do it. And you will get over your fear of anything pretty quickly. I just wanted to fit that in because the other thing I learned, and this is by a sales guy that used to work for me, is like always play to your strengths.

Like I wanted to be the renaissance man, the perfect like public company CEO when I was like your age. And I was trying to like wear my week and learn those skills. And he said, listen, I went to a sales seminar and they said, forget all that. Just like figure out what you're good at and do a lot of that. And I wrote about it at TechCrunch.

It's never swim upstream. And in your personal life or with your partners, yes, be a renaissance man. Be curious about the world. But when it comes to like your profession and making money, don't worry about what you're bad at. Unless it's like something horrible that's going to send you to prison like you're a psychopath. But like, you know, just whatever you're good at, do that.

And that immediately changed. Like I don't manage people. I'm terrible. I'm moody. I'm annoying. I always hired somebody to do that. And so I have a COO now that manages us. And just that's my main piece of advice. Like younger type. The first iteration of you implementing that was hiring the manager from that lesson? Oh, no. I mean at TechCrunch, I hired Heather Hardy.

She was my CEO. Like I just wanted to be the guy writing stories. She managed like the TechCrunch got up to like 50 people. You didn't manage them though. No. One time I tried to manage somebody. I got mad at an engineer about something. He quit on the spot. And I'm like, you can't. So we had signed the deal with AOL, but like it wasn't closed yet.

And I'm like, listen, listen, come here. I can't disrupt this. Like we're getting acquired. And I can't disrupt it. I'll give you $10 ,000 if you just like wait until after the acquisition. He's like, yeah. And so, and we're still friends actually. But he did. He waited. And then I personally gave him $10 ,000. But I'm terrible at managing people.

Yeah. It's interesting. Yeah. Like really bad. Because I'm moody. Yeah. But you know you're bad at it. Terrible. But you know you're bad at it and you're smart. I feel like you'd be able to figure it out. Why? I know what I'm really good at. I'm really good at hiring people and picking early stage companies that are going to win. Like that.

I don't need to be anything else in my professional life. So like why waste the time fixing something that you might not even be able to fix? I'm pretty sure it can't be fixed. Fair. I think I have some personality quirks that make me difficult to be around sometimes. Fair. Yeah. Who is the– I want to close out with like who the absolute best entrepreneur founder that's listening to this that would reach out to you to want to invest in them.

Who would that be? You mean the type of person or the actual name of the person?

I want the name first. Who do you want? Look, we're very much– our AUM is large. Our AUM varies widely. But we are a hedge fund, so we never end.

We've consistently been early stage investors even when our AUM was over $2 billion because that's what I like. We do other stuff as well, but other people do it. I am the guy– I want to be your first investor in your first round. I don't have to lead. I don't have to have any power. I think investors generally do more damage than good.

I'm very careful with that. I just– I'm very excited about somebody with an idea that is nothing and they want to turn it into something, and I want to be there for them. And I've found that even if they fail, which they usually do, they're going to have good memories of me and they're going to recommend me to other people. And that's all I really want.

Maybe the last question for you. How do you– And I know you guys are tremendous investors. You also have this whole thing figured out with investing, building, the podcast. The TechCrunch angle for me as an investor was really nice. You've got it all figured out. But I hope people understand you guys are people like investors like us always want to see on the cap table.

And I'm not just saying that because I'm finished. I appreciate it. Thank you, Mike. But you know that. You know that. You're good guys. And a lot of investors aren't. Don't be a bad fucking investor and ruin people's lives. Yeah. Just to make money. I appreciate it. Maybe– I really appreciate it. And we love co -investing obviously. But maybe one last question for you.

You said you're a bad manager but you like giving the founders advice. Like how do you marry the two? Oh, well– Because it's like if you give advice, you're kind of managing. It's like– I don't know. Like if I give advice– If I'm on the board on managing the investor and I can keep it together, right, for a board meeting once a month.

I'm talking about each and every day, especially when I'm hyper -stressed. I don't get super stressed anymore. But like when I'm hyper -stressed, like you can't manage people and be like hyper -stressed about whatever you're building.

So I just learned like I don't need to be doing that. Yeah. I don't– you really focused on that? It's like I think it's good to know your weaknesses. And yes, improve yourself. But think about if you want– if you can actually fix it and then if you actually want to fix it before you spend energy and time doing that. No, it's great advice.

Yeah, because you just lean into your strengths and you realize, hey, is this worth fixing or not? And go be successful. I like the advice. Yeah. But again, like I mean I don't have a lot of advice for you. Like you're way ahead of where I was at your age. I doubt it. You guys have figured stuff out very early on. No, seriously. And like I didn't make any money until I was 40.

And I just fucked up repeatedly. So you guys are pretty awesome and I'm pretty excited to be on this podcast. Thank you, Mike. Because this is like being on Rogan for me. Damn. That means a lot. Thank you so much. I really appreciate you coming on. I'm so excited. Yeah. I really appreciate it. It really means a lot to me and obviously all my partners and everyone here.

Thanks. I can't wait to send this to my mom and show her I made it. I'm not kidding. Mike, thank you so much. Thank you.