From building TechCrunch to backing Uber and Airbnb, Michael Arrington has had a front-row seat to some of technology’s biggest shifts. He joins Tommy on The Delphi Podcast for a candid conversation about the unstoppable AI race, the psychology of exceptional founders, and why he believes Bitcoin is the hard money the world needs.
Michael shares how he broke the news of Google buying YouTube, what working with Steve Jobs taught him, and how his relationships with founders translated into early investments in generational companies. He also opens up about burnout, leaving TechCrunch, reinventing himself through crypto, and staying convinced through brutal market cycles.
The conversation closes with his advice for entrepreneurs: face your fears, play to your strengths, and build a team that complements your weaknesses.

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Mike: [00:00:00] So just to be clear, everything we said before we started rolling is now on the record. He's evil. I believe he's a psychopath. 

Tommy: I don't think any US lab can slow down AI because China will lap us, they'll win AGI and they win. 

Mike: Airbnb, I was like, "I'm gonna do it," but I wasn't 100% sure it was gonna 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, "This... Who is this guy?" Like, "This didn't happen." And then it was true. Never said how I got the tip. 

Tommy: Are you lying? 

Mike: Am I lying? This person said, "Uh, 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.

Tommy: Hey, everyone. Welcome back to the Delphi Podcast. Today, I'm in person with Michael Arrington. I'm excited for him to [00:01:00] join us. Michael founded TechCrunch from his 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.

You ended up selling it to AOL. Um, 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 get a lot of mileage out of this, but you're, you were Times, Times 100 Most Influential People, and then you backed Uber, Airbnb, Pinterest, and founded Arrington Capital.

Mike: So just to be clear, everything we said before we started rolling is now on the record, and I can also speak... Like, the Time 100 thing? 

Tommy: Oh, yeah, for sure. 

Mike: Okay. So we can talk about Steve? 

Tommy: Anything. 

Mike: Talk about Steve McLaughlin, who was on, uh, one of your great podcasts recently and- 

Tommy: He was just on. 

Mike: Yeah. Um, well, that was a very nice introduction.

Thank you. 

Tommy: Yeah, of course. Thank you so much for coming on. It wasn't easy to get you. It's my 

Mike: [00:02:00] honor. Wait, it's not easy to get me? 

Tommy: It was not easy to get you. 

Mike: This is my favorite podcast. 

Tommy: I appreciate that. 

Mike: Like, I watch just about every episode. 

Tommy: Are you lying? 

Mike: So... Am I lying? No. I did say I don't understand everything.

Fair. You get super tech. But, uh, you guys are just, like, honest journalists. Like, it's just great to watch, so- Thank you ... and, you know, uplifting and all that, so. 

Tommy: Appreciate it. 

Mike: But you know all that. 

Tommy: 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.

Uh-huh. 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- Yeah ... institutions are valued. It kind of breaks down. There's this crazy reset. 

Mike: Yeah. 

Tommy: Is that where we are right now? 

Mike: Well, it's interesting. Have, have you, had you ever heard of the book The Fourth Turning?

Tommy: Not before Kelly told me about it. 

Mike: So I, I read a lot, mostly fiction for fun, but I read [00:03:00] just, like, I read constantly, and so I've read many, many nonfiction books. There's two books that made a, such a huge impression on me that I'll never forget them. One is, uh, Guns, Germs, and Steel, which was, I think was published in the early '90s.

Um, 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- ... our ears or whatever. It explains sports team loyalty, and it's just really interesting. The Fourth Turning, uh, is another one that's a little bit sad, but seems to be very accurate.

And the book was published in '97, '98, I think. Uh, 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 US history, but they claim this maps to Chinese history, which is ancient, uh, Roman, British, et cetera, is that you have these [00:04:00] crises that come up every roughly 80 years.

And they, the US and like, and it, for example, it 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 kinda overdue. And the argument, there's, th- y- 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, like, you know, read the summary on Wikipedia or have your AI do it for you. But, um, you have a generation of, of people who, uh, uh, are leading the country who are weak, i- is the only real word to describe it. Um, they're also generally pretty rich. Like, they live a pretty happy life.

And, um, they tend to screw things up, and, uh, that leads to, say, World War II. And then you have, um- The generation, you know, they win because of the newest generation, the people who are 18 to 20 at the [00:05:00] time, uh, 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, I'm Generation X, right? I was born in 1970. And we're the people theoretically in World War II who are, like, the generals. Yeah. So we're a good, we're a good generation.

And then it's the millennials are utterly terrible, but then, you know, their children fight, uh, you know, the next war. And, uh, you know, is there some truth to that? I mean, it's... We've all seen the good times make weak men, et cetera. Um- 

Tommy: That circular meme. 

Mike: 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. Um, AI is suddenly looking like a real contender here. Uh, but they argue that, you know, at some time in the next [00:06:00] decade, we're gonna have, uh, real troubles on our hand. And we as a country, we as a world, and we're gonna have to get through it, and we may not.

Um, but if we do, we come out much stronger. 

Tommy: What do you think is the... Like, the book breaks into these 20-year segments. 

Mike: Yeah. 

Tommy: And the last segment, I think, is when the, the crisis happens. 

Mike: Yeah. 

Tommy: 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.

Mike: 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, we just don't know. I don't know if in 1930, if they had read this book, they would've thought that the, uh, you know, the 1929 crash and depression was that. Um, they're all interrelated, of course, right?

That obviously led to Germany re-armany, re-arming, uh, 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 US flexed its muscles militarily [00:07:00] and, uh, you know, the results were not great. Uh, the financial crisis, our debt is unpayable.

We all, we all know that. We just don't know when it, you know- Shit hits the fan. And then AI is terrifying and awesome. Mm. So I don't know. 

Tommy: It's hard for me to figure out what would be more impactful in hindsight, either crypto or AI if we looked back at the- 

Mike: Cry- crypto is not as revolutionary as AI, is my belief.

I could be wrong, but yeah. 

Tommy: But why would that cause such a destabilizing 100-year event? Like everyone- AI. Yeah, like everyone talks about, like, the prosperity that would come from it, the, the solving medicine, new technologies, traveling to stars. 

Mike: Inventing a new species that is smarter than us. You can't even imagine how that could go wrong?

Tommy: Well, I can, but there's so many counterbalances. Like, there's so many benefits to it 

Mike: I mean, we're using AI extensively in war right now, right? 

Tommy: Yeah, definitely. 

Mike: And the Chinese are pretty good at it, [00:08:00] right? I mean, I, you know- 

Tommy: It's crazy that we're getting freedom in open source on AI from China, though.

Mike: Crazy. 

Tommy: It's nuts. 

Mike: It's, it's amazing, actually. 

Tommy: I love it. 

Mike: But- 

Tommy: But- 

Mike: Yeah ... 

Tommy: yeah. Curious what you think. Yeah. 

Mike: Well, I think it's fantastic. I do think, though, that we need to, um... 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, you know, war way, would be really awesome.

And to see- 

Tommy: See, I don't know that as a dumb American. I just assume China's crushing it, robotics, AI- No, 

Mike: I mean, you've seen the ghost cities. You know, they, they put so much emphasis on GDP and they go... You know, they build a city, that's all new GDP. Um, but the debt issue in China is pretty bad as well. And the people there, you know, they were...

They wanted to get their money out of China. Uh, there's [00:09:00] capital controls. Um, they still got out a lot, thanks to crypto. Um, but then they got into real estate, and they thought that was gonna save them, and it turned out it didn't. And so you have a population... You know, generally, you don't have revolutions, I- I'm speaking as a novice, but, like, you don't see revolutions happen until people are starving- Mm

basically. Usually. Um, 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. 

Tommy: Interesting. And I... So I'm trying to tie in, like, what we're seeing with AI with the fourth turning- Yeah ... to, like, try and understand, like, cause and effect here.

Like, in the US, we have hyper centralization, max safety doomism, anthropic and OpenAI want regulatory capture. China's giving us free open source. I think they're innovating way more than people give them credit for. 

Mike: Well, they're coming second, and they have a lot of benefits to coming second on this. 

Tommy: For sure.

Mike: Yeah. 

Tommy: But- 

Mike: Moat building in AI seems to be a difficult thing to do ... 

Tommy: like, the [00:10:00] model layer, like the, the heavy infra. 

Mike: Yeah, 

Tommy: yeah. Yeah. So I'm trying to figure out how this plays out. 

Mike: I don't know how it plays out, but it's gonna be really interesting. Also, it'd be a really good idea to own some physical gold and Bitcoin while we watch-

um, stay mobile, collect passports, you know, things like that, so... 

Tommy: Why, why, why Bitcoin with, with AI? Like, max money printing UBI happens or just- 

Mike: S- sorry, your question is why Bitcoin with an AI threat? 

Tommy: Yeah, yeah. Like, why own Bitcoin given the rise 

Mike: of AI? It's hard... 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, I- 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 US, buy a gun. 

Tommy: Can I ask, like, maybe going back to the AI stuff I know it's newsy, [00:11:00] 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- No ... the rate of progress? Like, what do you, what do you- 

Mike: No, no, that's just regulatory capture. I, I mean, it's, it, it is... You know what I mean by that.

Mm-hmm. It's clearly what it is. You know, getting to a pole position and then asking 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? An, uh, a benevolent dictator. Yeah. Right. Uh, that, you know, it, it loves us and cares for us, like we do with the animals in our zoos.

Um, there's no way to keep it under control. 

Tommy: Wait, the benevolent dictator is AGI. 

Mike: I think that's our best hope, is that it, it, the... That it loves us and cares for us and defends us. Um, not that it sees us as [00:12:00] 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. 

Tommy: The hard part is, like, I want AGI to love us, too. 

Mike: Yeah. 

Tommy: And if you talk to people, that's the safety argument. Yeah. And then you become an effective altruist, and then you- 

Mike: Oh, don't say that word. 

Tommy: I hate it. 

Mike: I don't even wanna... Yeah. 

Tommy: It's SPF for me. Yeah, 

Mike: yeah.

Tommy: But, but that inevitably- I kind 

Mike: of shudder when you say 

Tommy: that ... it's gross. Yeah. It just feels dirt- I, I feel like I'm being- Yeah ... talked down to by an academic when I hear it. 

Mike: Yeah. 

Tommy: But- 

Mike: Yeah ... 

Tommy: I'm just curious, like, where it, where it shakes out. I don't 

Mike: fucking know, man. Yeah, yeah. Like, get an AI guy on here. But, like, it's, uh...

Have you guys started doing a lot of AI investments? 

Tommy: Yeah. 

Mike: 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. Um- 

Tommy: We started a couple [00:13:00] years ago, though. 

Mike: Yeah. We're, we're lucky that we can invest in whatever we want. Uh, and we have branched out into AI.

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. 

Tommy: I mean, there's a lot of similarities between crypto and open source AI. But- 

Mike: Okay ... 

Tommy: but not many with 

Mike: potentials. I just think crypto is a, is a very convenient way f- for AI to conduct financial transactions 

Tommy: Like it's the least friction option for an AI agent to- 

Mike: Yeah

Tommy: transact money. 

Mike: Yeah. It's almost made for AI, right? 

Tommy: 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? 

Mike: Why does it need to be on chain? 

Tommy: I guess it's like the next step between your idea and frictionless commerce [00:14:00] 

Mike: Okay, explain to me how a ledger holds AI.

Like, actually explain that to me, what you mean by that. 

Tommy: I think- 

Mike: Like, there's AI- Mm-hmm ... it's a thing, and then there's crypto, which is, you know, generally seen as a payments platform. 

Tommy: I think this is- As 

Mike: well ... 

Tommy: really hard to figure out right now, but- 

Mike: Yeah ... 

Tommy: if you did have a model and the weights were not messed with and it wasn't censored by, you know, a company- Yeah

and it persisted around the world, it's a very- Yeah ... similar concept to Bitcoin, and you could ping that and inference against it, things like 

Mike: that. So you mean it's, it's in- it's inherently auditable? Is that what you mean? Yeah, 

Tommy: for sure. 

Mike: Yeah. Okay. Yeah. Totally transparent. Super cool. 

Tommy: Yeah. 

Mike: Yeah. 

Tommy: We could...

We'll see where it goes. 

Mike: God, it must be hard to be your age. And even harder to be much younger, like college students. Like... But, like, you know, the world's either gonna end or it's gonna be a utopia in a good sense. Uh, it, it's gotta be terrifying. 

Tommy: I met with... I had an Anthropic guy over to my house last night.

We were chatting, eating dinner and [00:15:00] 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 

Mike: that." Yeah. He was joking, I hope, right? 

Tommy: No. No, he wasn't. 

Mike: What? 

Tommy: No, he wasn't at 

Mike: all.

Let's talk about this. Who is this? 

Tommy: He's, he's an Anthropic researcher. He's a buddy, but- 

Mike: And he legitimately thinks that we have six months of- 

Tommy: Not just him. Legitimately most people- 

Mike: Yeah ... at Anthropic think- 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 privately.

Tommy: He's the only one that I've, like, in person talked to. 

Mike: 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 it. 

Tommy: That's the stupid part. Like, you go to Dario at Anthropic and you say, "If, if that's inevitable, shut the company down."

Mike: Yeah, but that doesn't, that doesn't stop anything. 

Tommy: Yeah. Because- Because China will keep going and- 

Mike: Well, Open I- OpenAI 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 [00:16:00] happens when we get there. 

Tommy: I don't, I, 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. 

Mike: It just- Not only can they not, they won't. 

Tommy: Mm-hmm. 

Mike: They just won't. 

Tommy: They talk a lot about stopping. 

Mike: Yeah, it's regulatory capture. 

Tommy: Yeah. And the reg cap goes back a couple of years. Like, Sam's been at Congress multiple times.

Mike: Yeah. 

Tommy: Like, they're all- 

Mike: Yeah ... 

Tommy: crying wolf. 

Mike: I've known Sam a long time. I met Sam in my TechCrunch days, and he had a startup. It was 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. 

Tommy: There's that video of him wearing the purple polo or something on stage pitching that company.

I forgot the name of it. Uh- 

Mike: I forgot the name of it too, but it ultimately was... He made, he made money for his investors, but it was, the tech was thrown away. But he's an exceptional salesperson. He has exceptional charisma. Um- Do you think 

Tommy: he's evil?[00:17:00] 

Mike: He's evil. I believe he's a psychopath 

Tommy: So s- uh- 

Mike: Which is different than being evil 

Tommy: Why, why is it different? 

Mike: 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- 

Tommy: What a show

do 

Mike: you even know what Dexter is? 

Tommy: What a show. 

Mike: Yeah. 

Tommy: Loved it. 

Mike: Um- Yeah ... yeah, a friend of mine hadn't seen it, uh, within the last few days, and I'm like, "Oh, you have such a treat to watch that show for the first time." Uh, and also I'm not a psychiatrist, so I can't really diagnose anybody. 

Tommy: Mm. 

Mike: But, um- 

Tommy: Well, how do you like, uh, how do you know, like what was the, the feeling that led you to identify him as like a psychopath?

And I ask this because I'm gonna ask you- Yeah, yeah ... about your founders. 

Mike: We do a lot of work at Arrington Capital around, um, psychology. And [00:18:00] there's a company, it's called Pathwise. It's an actually 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, 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 they are. Uh, and so there are certain tells, 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. 

Tommy: So you don't really know why, you just know they're not right? 

Mike: You... [00:19:00] 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, in our, our industry meaning tech in general.

Um, and it's useful to know one from the other. Yeah. 

Tommy: Maybe like a dumb question, but you, do you have... I'm assuming you wanna meet your founders in person then, that you invest in. Like, can you get that through a video call? 

Mike: Absolutely. 

Tommy: You can? 

Mike: Absolutely. 

Tommy: Interesting. 

Mike: Yeah. God, how many of your founders do you meet in person before investing?

Tommy: Not a lot. Yeah. But I try to make it a point, but we don't. It's- It's hard ... 

Mike: just too slow. 

Tommy: Yeah. 

Mike: Yeah. So, um, I mean, we can talk about it n- now if you want or- Yeah ... I don't 

Tommy: know. 

Mike: So- No, 

Tommy: sure. 

Mike: 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.[00:20:00] 

Tommy: Ugh. 

Mike: 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.

Mm-hmm. 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 are great. Probably half the people we invest in are narcissists. 

Tommy: Fundament- I don't think any other venture fund would admit that. 

Mike: 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. 

Tommy: Yeah. I mean, we have a very [00:21:00] similar... Like, uh, my partner Jose led what we call our founder North Star, and when we look at founders, it's, you know, do they have a chip on their shoulder? Yeah. Have they seen greatness? 

Mike: Yeah. 

Tommy: Uh, you know, are they trying to prove something to the world? 

Mike: Yeah. 

Tommy: 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, there needs to be more. 

Mike: Yeah. 

Tommy: Like, surviving isn't enough, but- 

Mike: Yeah ... 

Tommy: I don't think I've ever looked at it from a narcissist point of view. 

Mike: Also, I'm not talking about narcissistic personality disorder. I mean, that- Oh

you need psychiatric help. I'm just talking about people tend towards one of the seven personality types, and, and that's my belief. And, uh, you know, if they're a little narcissistic, that's not a terrible thing. 

Tommy: You mentioned 50% of the founders are... 

Mike: I mean, a lot of narcissists and a lot of psychopaths and a lot of schizoids.

That really- ... you know, 

Tommy: accounts for about- Is that the other 50? 

Mike: I don't know if it's 50. Look, narcissists are, like, a small percentage of the population, but a much higher percentage [00:22:00] in our world. 

Tommy: What's a schizoid? 

Mike: Uh, it's somebody who, uh... Well, it's somebody who's schizophrenic. You've heard that term. For sure.

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. Mm. 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 maybe psychopath, but I get schizoid vibes from him. And, um- 

Tommy: He has a really good PR team now, though. He seems human.

Mike: Well, he's, he's working out. He looks, like, awesome. 

Tommy: I know. 

Mike: Yeah. 

Tommy: Years ago, he looked- Weird. Like he was 

Mike: I mean, we all look a little weird, but yeah. Um I don't know why I needed to defend [00:23:00] Zuckerberg in there. He's- 

Tommy: Well, then the fact that I said he looks human now implies I also thought he was a lizard person back then.

Mike: 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. He, you know, he was pretty freaky. 

Tommy: Yeah. 

Mike: So- 

Tommy: What are the personality types you don't invest in? The ones that... 'Cause- 

Mike: Oh, I try- Yeah ... avoid psychopaths, like, at all costs.

So, we actually had a psychopath working for us once. 

Tommy: What? 

Mike: Yeah. Uh- 

Tommy: How long until you found out? 

Mike: Huge overachiever. Pretty quickly. Actually let him go eventually 'cause 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 another fund, and he had, uh, he had told that fund he was a partner with Arrington [00:24:00] Capital.

And, you know, I... We don't have a lot on our website for security purposes. We don't wanna, 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 didn't. 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 in him.

Tommy: Did... I mean, not to put you on the 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? 

Mike: When we hired him? 

Tommy: Yeah. 

Mike: I mean, we hired him as, like, a summer intern, and it- Ah ... and we, like, made him into, like, a something else. It was more permanent.

Tommy: Okay. 

Mike: He was, you know, a very junior guy, but, uh, I, 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. [00:25:00] Like, genuinely scared of him. Yeah. 

Tommy: 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 a narcissist. Like- 

Mike: No ... 

Tommy: they wanna take over the world. They overachiever. 

Mike: Gen- it is generally hard to tell, but there are some tells. Psychopaths, m- uh, you know, psychopaths mimic normal behavior. They, they taught themselves to be normal 'cause they, they don't feel empathy, uh, let alone sympathy.

They're, 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 realize that they creep people out, you know? And so they learn to fake it to the point where they become excellent at it, and quite often they fake being narcissists.

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. 

Tommy: I feel like I could tell- really quickly and connect the dots over longer periods of [00:26:00] time, which is obviously easier. Yeah. 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

usually how I catch it. 

Mike: Yeah. And I've made mistakes, and we have invested in psychopaths. But, um Uh, including one... We're not gonna mention the company here, but including one we were talking about a little earlier- Mm-hmm ... before we started rolling. Um, but, um, y- you know, it just helps if you can weed some of them out.

Tommy: I'd love to see fund, like, returns for the portfolio companies within your fund based on the personality type of the founder. Oh, we track 

Mike: that. Yeah, we 

Tommy: track. That's cool. 

Mike: Yeah, yeah. 

Tommy: Is it pretty markedly- 

Mike: Yeah, narcissists rock. 

Tommy: Man. 

Mike: Yeah. Interesting. They, they, they're a, they're a 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. I 

Tommy: like that. 

Mike: Yeah. 

Tommy: And the team knows to, like... It, it, yeah, it's just, it's just awesome that, that you're so focused on this [00:27:00] founder psychology. 

Mike: Yeah. So, uh, 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's served us well. 

Tommy: Is this, like, the start of the fund you did this, or was this something you learned and implemented later? I 

Mike: 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. Cool. All of our partners have been through it, so... 

Tommy: It's interesting. I do understand the weaponi- Like, if you talk to an AI model today, like- 

Mike: Yeah ... 

Tommy: OpenAI or Anthropic, if you put somebody's personality in there, like- 

Mike: Yeah ... 

Tommy: it won't give you advice on how to- 

Mike: Really? ... 

Tommy: effectively target them because it views it as, like, weaponization, like what you said.

Like, I don't know. 

Mike: I... The, the really, uh, funny thing with this is after I took the class, I had a meeting with the co-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 [00:28:00] 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." And 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 he...

And, 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. Hm. 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. Hm. Um, but that's the, those simple rules, like... And, and if you compliment a psychopath, they're not gonna react the same way as a [00:29:00] narcissist, so that's another tell, so...

Tommy: This is so interesting. Yeah. 

Mike: And it's 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- 

Tommy: That's definitely a superpower for being a journalist. 

Mike: It, yeah, it's not so great in, in personal 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 ma- you gotta be able to question yourself on something. 

Tommy: Can we talk early TechCrunch days? 

Mike: I'd love to, yeah. 

Tommy: So- Yeah ... like the genesis of TechCrunch is so interesting to me. You're in- Yeah ... the first Y Combinator meeting, like story- Yeah ... is it funded or accelerated?

I don't know the- 

Mike: It's an accelerator, but it- It's 

Tommy: both ... 

Mike: it, it, 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, it was like [00:30:00] just another thing, but it was like 20, 25 new startups I could go and cover in one day.

Tommy: Did he take the 7% early on? 

Mike: I don't, I don't know if it was seven early on. 

Tommy: Okay. 

Mike: Yeah. 

Tommy: So you're in- Yeah ... so like walk me through it. Like Paul invites you, or you just sh- you kind of show up, and you see all these startups, and you're like... 

Mike: 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. 

Tommy: So you were press before YC? 

Mike: Yeah, I started TechCrunch in '05.

Tommy: Okay. 

Mike: And you know, YC came a little bit after that. Yeah. 

Tommy: Okay. So before YC you were covering just normal tech breaking news? 

Mike: 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. [00:31:00] She had a job. I'd quit my job. I spent a year just surfing and playing video games-

and eating, eating, uh, burritos. It was fantastic. And, um- 

Tommy: It's crazy because you're so successful. Like, I can't imagine you taking a year off 

Mike: Just had had a rough couple years. If- I'd started my own company. I sold it, doubled investor money, didn't make any money myself because of- 

Tommy: That's the one with the 1X pref you didn't- 

Mike: Yeah, it was 2X liquidation preference- 2X

back then. So sold it for 35 million, but we ne- we had, um, taken 17 and a half million in investment. So- 

Tommy: You literally made nothing? 

Mike: 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 it sat in a garage for 10 years.

But, uh, so I was sitting there, and I was like, "All right. I, I need a job." Um- But I'd realized I had gotten out of tech for a little bit. Like I had, I had taken a little bit of time off and things were [00:32:00] moving very quickly. The read-write web was becoming a thing. Instead of static web pages, these web pages you could also interact with and like create content like a 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 gonna start a blog. Blogs were cool back then, and I'm just gonna post my research. And so the first few articles on TechCrunch, which I think are still there, were just, like, very formatted, you know, company name, you know, product description, fundraising to date.

And I- No 

Tommy: journalistic edge. What? No, no opinion. 

Mike: I, I didn't know what I was doing. Uh, but back then, everybody had a, like a Google search on themselves, right? I forget what it was called, but, like, you know, you get a notification in an email if, you know, there was a search, if, 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 [00:33:00] was. I had four readers. But they'd start getting these n- Google notifications, and then they'd come and they'd comment, and they'd send it to all their friends and their moms, always 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 till 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.

Tommy: Did you build that alert system? Like, d- I'm sorry, just- 

Mike: Built a what system? D- 

Tommy: double-click on that. Like, the, the alert system where people would get- Oh, no ... auto-tagged when they- 

Mike: You can probably still do this on Google. I don't know. But you'd go to Google, and you would, like... There was a way to set up a notification if Google found a document that your, that word was- 

Tommy: Did you know that going into TechCrunch?

Mike: Everybody knew that back then. 

Tommy: But, like, you- Yeah ... knowingly, like, used 

Mike: that as- There, 

Tommy: there was 

Mike: no Twitter, no social media. Like- 

Tommy: It's just such a great way to 

Mike: hunt for- This is one thing you had. Yeah. And so if somebody mentioned you, you'd learn about it that way. 

Tommy: So- 

Mike: So- 

Tommy: So then two- Yeah ... years go by, and [00:34:00] you're in YC.

Mike: Well, so the... TechCrunch 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. 

Tommy: So is this, like- Um ... a one-off good tip, or is this, like, demonstrating- You know- ... how deep you o- like, yeah, what 

Mike: was it? Never said how I got the tip, but it was a buddy of mine who had been funded by Sequoia. Hm. And the Sequoia partner had told him, boasting, and he called me. I've literally never told this story.

Wow. 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. 

Tommy: So y- it sounds like TechCrunch flipped from you going out and finding it versus- Yeah

people coming to you in '06. 

Mike: Yeah. I rented a house in Silicon Valley, and I started having barbecues at my [00:35:00] house. These things got famous. Police would shut them down. Um, hundreds of people, uh, would come. 

Tommy: Damn. 

Mike: 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 'cause I- the whole company was run out of my house.

Um, but people love being at those parties, so, um, that built a whole community as well. So 

Tommy: So then, so then in '07 though, you, you flip again, and now you start doing the work. Well- You're going out- 

Mike: I- ... 

Tommy: finding founders. 

Mike: I mean, I always did that. There, I'd have meetups at my house. Founders would come. Mm. 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

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- Yeah ... 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 [00:36:00] crash, so.

Tommy: Did you cover things negatively as well? 

Mike: 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. 

Tommy: I love how you say real journalists, but you're the one that built TechCrunch.

Mike: Yeah. They, 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, they were my rock stars. Like, I didn't care... I don't really care about celebrities, but, like, Steve Jobs, who was 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 were 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, [00:37:00] like, it was like I met some famous person, and, uh, and, uh- 

Tommy: There's so many rabbit holes here. What- 

Mike: I genuinely love entrepreneurs.

Tommy: I, I... So many rabbit... Now, now I'm going off, off... But, like, what was the most interesting stuff with Steve? Like, those are early days, '90s knows Steve. Yeah, yeah, yeah. That's not- 

Mike: Uh, I had a... So we represented him when he sold NeXT, uh, to Apple, and... This was a big deal in, like, uh, the late '90s, 'cause it brought Steve Jobs back to Apple.

Tommy: S- got it. That was... Okay. 

Mike: Yeah. 

Tommy: So he's back to Apple, yep. 

Mike: And he owned- he had NeXT and 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 'cause we were 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'd talk, sit down and talk to me. Uh, he was just a super cool dude. Now, I mean, he was, he was a bit crazy, but I never saw that. Like, he was very [00:38:00] charming. Um, and, uh, I wanted to be just like him when I grew up.

Tommy: Did you learn anything specifically from Steve that you think is, like- Yeah ... a valuable life lesson? 

Mike: Yeah, don't be a lawyer. Like- ... be out there build... Like, I was, like- In Silicon, I was at the law firm in Silicon Valley. You know, Marc Andreessen, 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 'cause we were the lawyers, and I worked on the Apple Next deal, but I wasn't cool. Steve Jobs was cool, right? Mm. 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 Andreessen, so.

Back when Andreessen had hair. 

Tommy: So Steve kind of taught you indirectly? 

Mike: 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 [00:39:00] a voicemail, 'cause 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 but me. But he said, uh, he'd got a bunch of Apple stock in the, in the, in the merger, and he left me a voicemail saying, "I wanna 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. 

Tommy: What the hell did he sell it for? Like, it had to have been- 

Mike: He did not- ... not He... I forgot what it... Like, at the time, you, like Wasn't super into Apple.

I- was he... I guess he was the CEO. He wasn't the CEO right away. I don't know, but he was still a little bitter about Apple, 'cause he was treated very badly in the '80s- 

Tommy: Yeah ... with 

Mike: Apple, so, um- 

Tommy: I mean, he passed away as a m- definitely a multi-billionaire before- Oh, yeah ... I mean, like, Tim Cook 10X'd to four tril, so it was $400 bill or something when he probably passed, something like 

Mike: that.

He had a lot of money, and he had that, that yacht he built. I've been on that yacht. Not with him, but, uh, his wife... He ne- I don't think he ever stepped foot on it, but his wife took it over, and now [00:40:00] she's, uh, she at least for a time spent a lot of time on it with her trainer, and I just thought- ... he was so pissed.

Um- 

Tommy: Was Steve alive while the boat was around, or did it finish? I 

Mike: don't think it was finished before he died. I don't know for sure. 

Tommy: That's so 

Mike: messed up. It's a sweet boat. You should look it up. The picture, it's very modern even now, but, uh- 

Tommy: It's kinda crazy to be on a yacht with your b- your dead husband's yacht with your boyfriend, but yeah, people are nuts.

That is 

Mike: crazy. Yeah. 

Tommy: Yeah. Um, so back to TechCrunch days, '07- Yeah ... Y Combinator, you're starting to break huge stories- 

Mike: Yeah ... 

Tommy: about founders. W- like, yeah, I wanna know, like, I, I, I don't really... I wanna know, like, about how you operated those days. Like, was it easy? Was it hard? Was early TechCrunch days easy hours?

It was, it was- Like, hire people ... 

Mike: I n- I gained so much weight. I worked... So I'm, I'm like, turns out I'm hypercompetitive, so I didn't love the work, 'cause it- it's hard to write. Like, let's say I was writing about some startup, and it was not some [00:41:00] simple startup. I, I... There were, you know, like I used to call them mufflers, like all the foundational sort of infrastructure stuff, 'cause I hated it and I didn't understand it.

If I was gonna write a story, there's a way to cheat, and journalists do it all the time, where they kinda write a story, but they don't understand the product. Mm. And it, the story is written, right? But you don't really learn anything. Like, I needed to understand the product and explain it a way so that I could talk to people and, and so I had to actually learn stuff, and, and 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 this breaking story, and so my sleep got really bad. Yeah. I'd work all night. I'd go to sleep at dawn. The, when the birds 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, uh, I loved April Fools' Day. And one [00:42:00] year I had, like, these infamous posts, but one year I was at a conference speaking on April Fools'- And I don't even remember 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, and there was 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 p- 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 past 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 'cause somebody read it [00:43:00] and was like, the Wall Street Journal editor was like, "Why the fuck are we saying goo-clear nu- 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. Is it- Yeah.

Tommy: What was, what was another irresponsible use of the, the press? I don't know if it's irresponsible though. It's driving views to TechCrunch, like you could argue that's- 

Mike: Oh, I, um- There's other April Fool's stuff. But, like, there was a time when... You re- do you even know what Zynga is? 

Tommy: Oh, yeah. 

Mike: They had this... God, I'm 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. 

Tommy: I remember watching your YouTube video on it. You were standing up in a crowd, and you were saying- 

Mike: Terrible video.

Yeah. 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 [00:44:00] that, right? God, you know, I don't remember what she 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. Hm. Um, so I... Uh, it was actually, like, I didn't start it as a business. I had 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. 

Tommy: 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 were like, "Hell, I kinda wanna actually sell this, and I'm burnt out"? Or was it... How did you- Um- Did you say your health was going downhill? You 

Mike: know, 

Tommy: was it 

Mike: maybe- Yeah, I was pretty burnt 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 then he went to AOL. And [00:45:00] he's like, "We'd love, we'd love to buy TechCrunch." 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 on 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. 

Tommy: You're not 300 pounds now. 

Mike: Uh, no, I weigh a little less. Uh, but I was so competitive that it... nothing else mattered besides working, and it was rough. 

Tommy: But how do you... I don't understand how you turn it off, though. Like, how do you- 

Mike: I sold the company, and then I started a venture fund- 

Tommy: Fair

Mike: which AOL backed. They were the, they were the ba- they were the, the main backer. And then I had Sequoia and, uh, not Andreessen. They weren't really doing anything yet, but, uh- 

Tommy: This is pre-Craig 

Mike: down ... called Big Funds. This is just- Yeah, this is like 2010 or '11. Um, it was approved by the board. They'd bought Arianna Huffington's, uh, the Huffington Post by then, and, and I...

And somehow she was my boss. And, um... But I wouldn't take her calls, 'cause she was annoying. Um- [00:46:00] And I had to 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 TechCrunch, and everyone went ape shit because I was both, like, a power broker at TechCrunch and an investor.

And sh- Arianna didn't like the press, so she fired me on, like, a tweet, which immediately AOL came out and said, "You know, 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 know, 5 million bucks, like, instantly. And, uh, so they regretted that, but, um- 

Tommy: It feels like the- 

Mike: Yeah

Tommy: the newer generation would understand, like, Semi Analysis being a comp, like, big research firm. 

Mike: They don't understand what? 

Tommy: Like, Semi Analysis being a comp to what you did. Like, big- Yeah ... research firm now starting a fund. 

Mike: Yeah. 

Tommy: Yeah. 

Mike: But, uh, yeah, so then I was free. And then, um, I got even fatter somehow.[00:47:00] 

I mean, 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. Nope, nope, nope." 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 

Tommy: feel like not fit Mike is the successful Mike, but obviously it's not healthy, but... 

Mike: It... Hey, what... Wait, what are you saying about current Mike and his level of success? 

Tommy: Well, no, now you're just escape velocity, but 

Mike: I, uh-

I don't know, but I, uh, I feel a lot better now. 

Tommy: Nice. 

Mike: Yeah. 

Tommy: So you... So the fund is done- 

Mike: I'm never gonna let you... I'm never gonna forgive you for that scene. 

Tommy: I, I didn't mean it in a bad way. 

Mike: Yeah, that makes it worse. 

Tommy: Apologize. 

Mike: Fat Mike was a successful Mike. 

Tommy: I didn't say it, like, with that kind of tone, though.

It was, like, genuinely- 

Mike: I will watch the tape later, but, you know, it is what it is, right? 

Tommy: So [00:48:00] you leave the fund- I, I can't, 

Mike: I can't. 

Tommy: Cut. Mike's gonna kill me. So you, so you leave, the fund is done. Arianna, you get paid. 

Mike: No, the fund was great. 

Tommy: Oh, the fund kept going? 

Mike: They had already... Oh, we did three funds. Yeah, it was CrunchFund.

We did three funds and, uh, uh, it just didn't work for AOL anymore, so. 

Tommy: And CrunchFund was, like, sourcing founders from TechCrunch? Like, that was the angle or- Yeah, 

Mike: I still had every relationship I had, so I, you know, right away we invested in Uber. I was actually... Uber, uh, 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...

'Cause he'd 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 start it. I think he had started at that point, but he wasn't the CEO. And then he told me about the other two, and he [00:49:00] really liked one of the other two, and I'm like, "No, 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 this because of me, but, like, he ended up firing the CEO and taking it over, and, you know, it, 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 'cause I'd written positively about them for a long time. 

Tommy: You say a few others so, like, casually, but those are, like, generational winning companies.

Like- Oh ... those are ridiculously successful investments also. It was 

Mike: stupid. Yeah, it was stupid money. But, like, when I put money in, I, I, uh, Uber I had a feeling, but Airbnb I was like, "I'm gonna do it," but I wasn't 100% sure it was gonna hit. But I put, like, 100 grand in and that turned into [00:50:00] 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... By the way, these were very small funds. They were all about 30 million, so they weren't big even then. Um, but- And the reason that we're big is I really like the earliest stages of startup.

Tommy: Mm-hmm. 

Mike: I hate it when you have to look at a spreadsheet. Hate it. Um- 

Tommy: I agree. 

Mike: It started like, I started just getting a little bored. Like, you know, I take the meetings just like I had done at TechCrunch. I'm meeting people, and then instead of writing about them, I'm writing a check. But I just, it felt like Same shit over and over, and I, I don't understand.

Like, these people... Like Reid 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, I'm 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 stop doing it, and I think it's because they- they're afraid of [00:51:00] 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 wanna do this anymore," 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."

Tommy: So... How, how did you find, like, how did you find Coinbase and Bitcoin in, in '17 though? Like, what was the genesis? 

Mike: Oh, it was TechCrunch. 

Tommy: TechCrunch. 

Mike: I saw these guys all the time, everywhere. Yeah, like I just knew all of them, so yeah. 

Tommy: 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 TechCrunch-wise, like writing about them, going to the parties, or was it different?

Like it was- 

Mike: When? 

Tommy: The second and third funds, 'cause the first fund- 

Mike: No, Tech, they wouldn't even allow me in the office. 

Tommy: Okay. 

Mike: Yeah, yeah, yeah. I didn't know them at all. '

Tommy: Cause the first fund- Yeah ... sounds like [00:52:00] you're kind of riding this crazy social network you have. Yeah. The investment comes early. The second and third fund sound different in terms of like maybe more traditional venture style funds versus- 

Mike: They were exactly the same.

Okay. And had, and had some big wins, uh, but they weren't as easy as earlier on when I like had just started the fund and went from TechCrunch to writing checks. Sure. So it was like a three-month period where like everything I wanted I got, except Stripe. 

Tommy: Ah. 

Mike: I almost got into Stripe. Hmm. 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... We'll... Small check, like 100 grand." I'm like, "Fuck yeah." And they went back, and the other investors were 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 100 grand check. 

Tommy: So you don't wanna hang out with me just 'cause you'd be richer?

Mike: I love you and I love this apartment, but like, no- ... I'd, I would be, uh, [00:53:00] doing other things. 

Tommy: Yeah. 

Mike: Fair. Fair. Yeah. 

Tommy: So what was the decision tree to wake up and say in 2017, "Ah, full crypto, no more traditional VC"? Was that a day thing, a month thing? What was the- 

Mike: Like all great stories, it's a woman, and she's explaining all this whole shit 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? 

Tommy: Oh, yeah. 

Mike: And I was like, "Oh my God." So we put a little bit of money in a couple of them, and like i- those little bit of money became like a whole lot of money. And I said, "Oh, I'm gonna start a fund around this." 

Tommy: A- and that...

Wow. So that 

Mike: was- But, uh, Luna was in there- Yeah ... and some other big winners, so yeah. 

Tommy: So that's a liquid investment, but your... Arrington Capital's very active doing private VC deals too, though. 

Mike: Yeah, just not lately. 

Tommy: Fair. Fair. Just not excited with who you're seeing, or what's the- 

Mike: Well, AI, uh, we're- we've done quite a few AI deals.

Uh, we've done a [00:54:00] few crypto deals, but, uh, you know, normally in these down times is the best time to invest. Like, that's super true. But, you know, I think people just kind of gave up when we had a brain drain into AI, and so we just need to get through this period a little bit. I think crypto's really trying to figure out what it's gonna be at this point, so.

Tommy: I think the- 

Mike: Yeah ... 

Tommy: most successful investments we ever made are always in bear markets. 

Mike: Yeah. Y- well, and the reason is because valuations come down and there's less, there's less competition from other investors, right? Um, it, it's super true. Um, 

Tommy: but- As someone, like, I mean, the- 

Mike: But I- 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 and I'm like, "Eh." 

Tommy: No, I mean, we've, we've slowed down on the crypto side and we're way- Yeah ... more active on the AI side. It's just- 

Mike: Yeah ... 

Tommy: what it's like. Yeah. Yeah. The, the crazy part to me, though, is you've been through so many cycles, like, very intimately.

Yeah. Like, [00:55:00] you've been involved in- Yeah ... 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? 

Mike: Yeah. 

Tommy: Gotta be a lot. I mean- 

Mike: Yeah ... '

Tommy: 18, '21. Recently, that was three. '

Mike: 22, not '21. 

Tommy: 22, yep. 

Mike: It was spring of '22. Um, and then this last one.

Yeah. 

Tommy: You're just, like, you have so much context on bubbles. Like- 

Mike: I made more money in 2021 than I've made the rest of my life combined. And I bet you guys did quite well. 

Tommy: Yeah, we did okay. 

Mike: Yeah. 

Tommy: Yeah. 

Mike: Um, and I just moved to Florida. 

Tommy: I moved in '21 too. 

Mike: 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... 'Cause '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 [00:56:00] accident. Hmm. 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 were going for a walk, this was 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, 'cause 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, you just go all in.

Tommy: I was, uh, like, pretty, not depressed, but I don't really get depressed, but like pretty- Yeah ... down a couple weeks ago. 

Mike: Why? 

Tommy: I was just like, you know, the market sucked and I wanted to go get out of the house and- 

Mike: Yeah ... 

Tommy: 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- Yeah

hours," and I took a bunch of pictures. That day was 57K Bitcoin, couple weeks ago. It's just crazy how that happened. 

Mike: Yeah. Yeah. 

Tommy: And I thought it was dead too. 

Mike: Yeah. [00:57:00] You were dead? 

Tommy: No. I mean, I didn't think Bitcoin was dead, but the venture side's tough. You're not, we're not seeing the stuff we used to see.

Mike: 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- 

Tommy: Can I ask, like, not a, a dick question, but maybe for, like, the listeners, is that, like, because you have money now? Or is that, like, because- 

Mike: No, no, no, no.

No. Actually, and I don't... Money's not that important to me. Uh, it, like, really... Ah, 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, uh, their old- I don't

great inve- 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 were rough times. I mean, it was like cr- tech [00:58:00] was dead for like four years until Google went public. Nothing was happening. There was a venture fund that returned $0.

It was like a $200 million venture fund, Drake Fisher Jurvetson, that like around that time they actually managed to return $0 of it. 

Tommy: Zero. 

Mike: 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. But like- Unless there's nuclear war or something or AI takes over. 

Tommy: But knowing, knowing what you know though, and being through so many cycles, like you, you have to wake up and, and make a decision like, "Do I spend my time on crypto or do I spend it on AI?"

Oh, yeah. Like- Yeah ... how do you, how do you piece that puzzle together? 

Mike: 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- Mm ... and, and mentoring [00:59:00] 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 put together. You have 

Tommy: an incredible team. I've met a lot of them. 

Mike: 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've brought in a few deals.

Uh, you know, we're, we did the SPAC for Evernorth, the Ripple debt, which I actually think is gonna 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 out of that, and I get a lot of joy out of making people rich, right?

Like I... I think five people became millionaires when I sold TechCrunch. 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 out of that now. Mm. And so I don't know if I'm gonna reinvent myself, and I actually don't even think I'm addressing whatever your original question is.

Tommy: No, you're addressing it better. Oh. Do, do you like... Is there any like- 

Mike: But I, I feel like the fundamentals of crypto are very sound. 

Tommy: I, I [01:00:00] agree. It's just the, the, it... I don't know how to describe- 

Mike: Like, why would I stop believing in it? I 

Tommy: don't- 

Mike: Because- 

Tommy: I don't not believe in it. I super believe in it. This just- 

Mike: I'm just accusing you of that.

Yeah. I'm saying 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. 

Tommy: Yeah. No, no, I agree on that. 

Mike: Hard money that governments can't stop, right? We've had hard money in the past, but government, as we've seen, they always debase it. 

Tommy: Yeah.

Mike: Bitcoin realistically can't be stopped, and that's going to save us all. 

Tommy: Yeah. No, I... Well, they're never gonna slow down spending money. We've tried. Elon tried. Like, we're never gonna- 

Mike: We absolutely cannot. 

Tommy: Yeah, there's no way. Yeah, 

Mike: the only way to do that is, again, with a benevolent dictator, somebody who doesn't answer to democracy, which, you know, democracy is two wolves, what is it?

Two wolves decide- and a sheep deciding on what's for dinner. Um, I mean, it's just, it's just, you know, democracy doesn't work. Churchill said, you know, what did he say? He said, "Democracy is [01:01:00] terrible-" It, it's just better than everything else or something? Like, it, it's a real problem. And so we're never gonna stop spending.

Tommy: So do you, like, being so- do, do you prepare in a certain way? Like, personally? Like, you're not really involved in politics that I'm aware of, or- 

Mike: 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- 

Tommy: Guns and Bitcoin and gold.

Mike: 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. Mm-hmm. And the other way is, you know, you buy all the stuff. You know, y- 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 'cause I'm a God-fearing American. I believe it's our, literally our duty to own a, a weapon safely and, like, responsibly. 

Tommy: Same. 

Mike: But I hope that it doesn't come to it. I am a little worried that every fucking [01:02:00] billionaire I kn- Are we allowed to swear on this podcast? Yeah, I know we are.

Of course. Listen along. But every fucking billionaire I know, uh, you know, has a goddamn bunker somewhere. And, like- 

Tommy: Do you have a bunker? 

Mike: I'm not a billionaire yet. But, like, no, 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.

Tommy: Yeah. 

Mike: 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, they're also the ones in charge. It occurs to you? Yeah, they're in charge of everything. And so, you know, they know what's up. 

Tommy: Yeah. I, I... Like, what, what's the end game?

They go in their bunker, they come out after the nuclear war and everything's fine? Like, the world's over. Look- What's the point? It's 

Mike: like- ... 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?

Tommy: Yeah. '

Mike: Cause you... Yeah. 

Tommy: They'll kill you. 

Mike: It's gonna suck- 

Tommy: Yeah ... 

Mike: if that happens. Yeah. 

Tommy: What, what's your like... Do you have any [01:03:00] advice for, like, the 20-year-olds? I 

Mike: just sounded super crazy, didn't I? 

Tommy: No, not at all. The, the billionaires- ... with the bunkers sound crazy. 

Mike: Uh, I mean, would you have a bunker if you could, like, afford it without blinking?

Tommy: Absolutely. 

Mike: So they're not crazy. 

Tommy: Fair. 

Mike: They're crazy in that they're, like, actively... I mean, I wanna say that. Like, it's so cliche, but, 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 it. You know, we talked about with AI, like yeah, let's say the US says we're gonna regulate and slow down AI.

That's not gonna do a darn thing except make sure we lose, right? So it's a catch-22. 

Tommy: These, these billionaires that have the bunkers that you know, like any interesting ones that you think 

Mike: like- Oh, I only know what I read in the press. Fair. No, no one has actually taken me to their bunker or like invited me into the bunker group.

I- Um, I don't know if Brad has one. If he does, I don't know about it. But- 

Tommy: I feel like if they tell you, it ruins the whole point ... 

Mike: I mean, you wanna be included in these things, 

Tommy: right? Yeah. Fair. You wanna- You wanna be part of the [01:04:00] bunker ... 

Mike: we could group together. You know, there's enough of us here in Miami. We could get a bunker and just- 

Tommy: I mean, if I contribute 100 bucks and you contribute the rest, we could have a great bunker

Mike: Oh, I think you're doing a lot better than being able to contribute 100 bucks. But, you know, we could just, uh, socialist utopia in our bunker. 

Tommy: It would be fun for a couple of weekends. 

Mike: It might be lifesaving. I don't know. Yeah But- 

Tommy: 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 have- I don't know how old your kids are, 

Mike: but- No, no, I don't have kids. Uh- Okay ... I have a stepdaughter. Uh, eh, but that ended when, uh, Natalia, my, uh, ex... You didn't ask about the ending of that. I mean, we'll 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 know. 

Tommy: There's gotta be something they could do, like use AI all day. I'm j- 

Mike: By the way, you're, you said 28? 30- 32 ... You're, you're, [01:05:00] 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- 

Tommy: Scary as fuck. Can't buy a 

Mike: house ... $5 in your account. Yeah. Like, what are you gonna do? Like, I- Yeah ... I don't know. 

Tommy: I think the, 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. 

Mike: Well, 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?

Mm. 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? [01:06:00] And I, I... It's scary. It's super scary. 

Tommy: UBI scares the shit out of me because I'm, like, such a pro-meritocracy kind of person. Like- 

Mike: Yeah

Tommy: I don't think the person that works less than me should have more than me. Like, that's just my point of view. I 

Mike: agree, but what about when, like, you know, like, 5 million people in the US starving to death? Like, what are you gonna do? Yeah. Right? I mean, you're going to do some form of UBI. We already do some form of UBI.

Everybody has free medical care. You... And- 

Tommy: Food stamps ... 

Mike: it's not great, but yeah. But gosh, those people live miserable lives. 

Tommy: We're kinda closing back to the fourth turning It's, I feel like we've come full circle 

Mike: And 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, [01:07:00] I don't think we even understand right now sitting here how bad it's got. 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, we'd, we'd petrify.

Tommy: Like, bad it's gotten, like how fast it's moving i- is- 

Mike: Yeah, just how, like, scary everything is, how there's... I mean, these Flock cameras fascinate me, and like- 

Tommy: That's nuts to me ... 

Mike: 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 that make me?

Uh- 

Tommy: Those are the good ones. 

Mike: Yeah, I'm not so sure they are. But the, uh, uh, 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- 

Tommy: I thought I just realized politics 'cause I was getting older.

I didn't think, like- 

Mike: Well, world's very different than it used to be. Men and women used to go on dates and, like, like each other.[01:08:00] 

Like, the world was, like, pretty nice. And, um- 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 a, I'm really scared for a lot of things right now. Yeah. I- Okay ... 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. 

Tommy: The rumination part I've spent a lot of time learning about because it's- Yeah ... really hard to let, like, a really bad investment go, a really bad- Yeah ... you know, something you missed, a great employee, a- Yeah, 

Mike: yeah, yeah

Tommy: an event. Like, rumination could, could kill you if it's not productive. Yeah. I like the Pema 

Mike: Chö- I don't know if it would kill you, but it would- Well- It definitely sucks. 

Tommy: Yeah, it 

Mike: sucks. It's not productive. 

Tommy: What's like, for me it was like Pema Chödrön helped me a lot, like, on that. Like, what, what gets you out of- What book?

ruminating? Pema Chödrön, like a really great Buddhist. I love her books. She has one on getting [01:09:00] unhooked, which is phenomenal. 

Mike: Taoism's actually more my style. Uh, it's very easy to look up the difference, but, like, it, it speaks to me. It, it definitely speaks to me. Yeah. And, uh, so I'd love to read the book. I don't know who that person is.

Tommy: I'll send you one. Yeah. Yeah. It, it was good. But, but sorry, so how do you get out of ruminating, though? What's your- 

Mike: I r- oh, I'm terrible at it. Yeah. 

Tommy: But, but how do you- Yeah ... like, how do you focus on productive stuff if you don't? Well, I, 

Mike: I have some hobbies. You know, uh, I think you said you go for a run sometimes.

Like, I, I- 

Tommy: I don't like running. I just go. 

Mike: Yeah. You know, actually, one of the things I've talked about today is, like, you, you h- 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, in the office near me ran marathons all the time, and I didn't really even know what a marathon was, and it scared the hell out of me 'cause I'm not built for running I ran a marathon in a couple years. I trained for it and I ran a marathon.

I hated it, my nipples bled. Like, it was a disaster, but I finished, [01:10:00] 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, like, just whatever you're scared of, just go do it. Mm. And you will get over your fear of anything pretty quickly.

Um, I just wanted to fit that in, 'cause 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, where am I weak, and learn those skills, and he said, "Listen, I went to this 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, oh, never swim upstream. Mm. 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.

Un- unless it's, like, something horrible that's gonna 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 at it. I'm moody, I'm [01:11:00] 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 for, like, younger entrepreneur types. 

Tommy: The first, the first iteration of you implementing that was hiring the manager from that lesson? 

Mike: Oh, no. I mean, at TechCrunch I hired Heather Harde. She was my CEO. Like, I just wanted to be the guy writing stories. She managed, like, TechCrunch got up to, like, 50 people.

Tommy: You didn't manage them, though? 

Mike: Fuck no. They d- they c- Interesting. One time I tried to manage somebody. I got mad at an engineer about something and he quit on the spot. And I'm like, "You can't q-" So we had signed the deal with AOL but it, but, like, it wasn't closed yet. Mm. And I'm like, "Listen, listen, come here.

I can't disrupt this. Like, we're getting acquired and, like, 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, uh, he did. He waited and then I personally gave him $10,000. But- ... I'm terrible at managing 

Tommy: people.

Mike: Yeah. 

Tommy: That's interesting. Yeah. 

Mike: Like, [01:12:00] really bad at it. 'Cause I'm moody. Yeah. 

Tommy: But you know you're bad at it. 

Mike: Terrible. 

Tommy: But you know you're bad at it and you're smart. I feel like you would be able to figure it out. 

Mike: Why? I know what I'm really good at. Hmm. I'm really good at hiring people and picking early stage companies that are gonna win.

Tommy: Like that. 

Mike: I don't need to be anything else in my professional life. 

Tommy: So, like, why s- waste the time fixing something that you might not even be able to fix? 

Mike: Well, I'm pretty sure it can't be fixed. 

Tommy: Fair. 

Mike: I think I have some personality quirks- ... that make me, um, difficult to be around sometimes. 

Tommy: Fair. 

Mike: Yeah. Yeah.

Tommy: Who is the, uh... I wanna close out with, like, who the absolute best entrepreneur founder that's listening to this that would reach out to you to wanna invest in them, who would that be? 

Mike: You mean the type of person or the actual name of the person? 

Tommy: I want the name first. Who do you want? 

Mike: Look, we're, uh, very [01:13:00] much...

Our AUM is large. Our AUM, as you know, like varies widely, but we are a hedge fund so we never end. Um- We've consistently been early stage investors, even when our AUM was over 2 billion, uh, because that's what I like. We do other stuff as well, but other people do it. I'm the guy, I wanna 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 a idea that is nothing and they wanna turn it into something, and I wanna be there for them. And I've found that, like, even if they fail, which they usually do, they're gonna have good memories of me, and they're gonna recommend me to other people.

And that- that's all I really want. 

Tommy: Maybe a last question for you. How do you, um- 

Mike: Yeah, and I know you guys are tremendous investors. You also have this whole thing figured out with, like, [01:14:00] investing, building, the podcast. Like, the, you know, the TechCrunch angle for me as an investor was really nice. Like, you've got it all figured out, but I, you know, I hope people understand, like, you guys are people, like, investors like us always wanna see on the cap table.

And I'm not just saying that 'cause I'm- I 

Tommy: appreciate it. Thank you, Mike ... 

Mike: like, you know that. Like, you know that. You're good guys. And, you know, a lot of investors aren't. Don't- don't be a bad fucking investor and ruin people's lives- 

Tommy: Yeah ... 

Mike: just to make money. 

Tommy: I appreciate it. It- Yeah. Maybe... I, I really appreciate it, and, and we love co-investing, obviously, but maybe one last question for you.

You said you're a bad manager, but you- you like giving the founders advice. Like, how do you marry the two? 

Mike: Oh, well, that's- '

Tommy: Cause if, like, if you give advice, you're kind of managing a ti- like, I don't know. Like, if I give advice, I'm, like- If 

Mike: I'm on the board, I'm managing the- the investor. 

Tommy: Mm. 

Mike: Uh, and I can keep it together, right?

Mm. 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 [01:15:00] whatever you're building. So, uh, I just learned, like, I don't need to be doing that.

Tommy: Yeah. 

Mike: I don't... You- you've 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, um, before you spend energy and time doing that. 

Tommy: No, it's great advice. Yeah. 'Cause you just lean into your strengths, and you realize, hey, is this worth fixing or not?

Yeah. And go be successful. I like the advice. 

Mike: Yeah. But again, like, I, 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. And you guys have figured stuff out very early on. Thank you. No, seriously. And, like- I didn't make any money till I was 40, and I just fucked up repeatedly.

So, um, you guys, you guys are pretty awesome, and I'm pretty excited to be on this podcast because- Thank you, Mike ... this is like being on Rogan for me. 

Tommy: Damn. That means a lot. Thank you so much. I really, I really appreciate you coming on. It's, uh- I'm 

Mike: so excited. 

Tommy: Yeah. I [01:16:00] really appreciate it. It real- really means a lot to me, and obviously all my partners and everyone here, so 

Mike: thank you.

Thanks. I can't wait to send this to my mom and show her I made it. I'm not kidding. 

Tommy: Mike, thank you so much. 

Mike: Thank you.