There's a handful of us that have known each other for a very long time. Me and Sax probably for 25 years, and then me and Jason for maybe 23.
And the three of us, there was like an early cohort of people in Silicon Valley that were really tight. We were three of those people, and it was a very small circle at the time because Silicon Valley was not that important. And we had two things: we would work together, and we played poker together, and we all loved poker, just a thing. And when COVID happened, we were just totally shut out from each other. And so we just started to film each other. And the fourth person, David, we've known for about 13 years. So he's been in our friend group for about 13 years, but that's how it started. We all used to live within like a few miles of each other. We used to spend all this time together, and then we were just completely put into our homes.
Would you typically play poker together?
Every Thursday at my house. And now after COVID, it's back every Thursday at my house, and we have like dinners, and we bring interesting people, and we kind of like will sit there and grill them, and not really grill them, but get to know them, and it's a treat for us. And then when they took it all away, like we would just record ourselves, and then I was like, 'Fuck it. Just post it.' It's like, 'This is so great. Just post it.' Like we're all going crazy. We're just like, 'What? What do you have to lose?' And then the thing just went crazy. Last week we were number one for the first time.
It really is a vision into a world that no one gets to see, right? I've been lucky enough a couple of times in my life to be in a room where people have conversations like the conversations you guys have every week, right? But I remember when I first heard it because it felt like the highest level insider information, right?
Yeah. I think that that's a really nice way to think about it.
And then to make it good takes real effort.
Tell me about each of the members.
They're also particular. Like Jason, I would say is, you know, the scene like where Ben Affleck says to Jeremy Renner, 'We're going to take my car, can't tell you where we're going to fuck some people up, and you can never talk about it again,' and the guy says, you know, kind of like, you know, 'Your car, mine,' or whatever, you just call. And he's so loyal, but he's also so infuriating because like his views I find just so frustrating, but I love him. And I love him like I would love a brother who I disagree with. Sax is, he's just the very, very smart kind of poker player, strategist kind of guy. And then Freeberg is like an incredibly earnest, first principles thinker, kind of like right on the borderline between naive and productive because I think sometimes he's a little too idealistic. But so then we're all like kind of like very different, but then we all grew up in a moment where like none of us were anything, and then you know we had various levels of success, and then various levels of kind of downfalls, and we all kind of just stayed close. That's, I think that's the key part.
You came up in Silicon Valley after the first wave of the PayPal mafia types.
I came right at the end of that. I joined a company and you know it had been bought by AOL. I was like, 'All right guys, I'm ready for this fucking party. Let's go.' And they were like, 'No, party shut down, bro.' And you know, everything had hit the skids.
But it seems like you've been welcomed by that old guard for some reason.
Well, I came right at the end of it. So, as far as everybody else is concerned, I'm effectively the old guard now. And I think I grinded in a way where I haven't really achieved what I'm trying to achieve or my potential, but I've demonstrated that I'm like decently good at various things.
Were you aware when you said 'just post it' how revolutionary the podcast is?
No, I didn't understand that our friend dynamics are actually quite rare. I didn't understand that. And look, we have always been just full-on totally candid, super candid, very off color, but it's very disarming as a result of that. I just didn't know. And I had only known that. So, I didn't know that other people weren't making that kind of music.
Well, other people talk like that and think like that, but don't release stuff like that, right?
Yeah. There's a real dividing line between people's public perception and who they actually are. And on your show, that's really these people feels revolutionary.
Yeah, it feels revolutionary.
Yeah. I think like there's like a simplified Maslow hierarchy which is like you have sex at the bottom, you have money in the middle, power at the top, and I think that for many years there was all these status games where you were trying to achieve one of the three, and it looks like a triangle because at the top power is so fleeting and there's so little of it. Few people play that game. More people can play the power game, and everybody can play the sex game basically, right? And I think what's happened is actually like this bottom layer has gone away and it's more now fame. And I think the fame game, the problem with like that status game is everybody that seeks it because of social media basically runs into a brick wall, and they run into a brick wall because they're not themselves. People just sniff it out and they're like, somebody said this which I think is true: nobody wants to be fucking sold something. Like even if you're the guy that's supposed to be selling you something, you just have to not be selling. And so you just have to be yourself and deal with it. And that's super hard for a lot of people because most of the time, most of our lives we are boring, predictable, not really interesting. We're all just grinding along, dealing with the same shit everybody else is dealing with. Woke up today, my fucking hip hurts. Woke up today, I feel, you know, out of shape, and, you know, I'm not eating well. It's the typical shit. And yet, instead, if you were to look on Instagram, it's like, 'I woke up today, I fly my private jet, and now I'm on my boat, now I'm in this party,' and it's like, this is not fucking true.
And even if it is true, it's not particularly interesting.
I mean, I don't think any of those people are much happier than anybody else.
But you have to play this lie. And I think the problem is the lie gets undone. So, it's just easier to be yourself. And then, oddly, being yourself is actually the hardest thing to do because so many of the times what you have to offer is really not that much. And you have to be okay with that. But then that's what actually sells because it's not being sold. It's weird.
One of the things I noticed about the show is that you often speak less than the others. And when you speak, it seems much more important.
I don't know. I think I've learned the hard way. I used to really need to hear the sound of my own voice because I think I felt like if I'm not saying something, it's not important, or how can they say something and I'm not saying anything? It must be like being in a band and you're like, 'Oh, that's a great guitar riff, oh, that's a great lyric, okay, hold on, I need to add to that,' because if I don't add to that... And now I'm more like that fucking thing can just stand on its own right there, and I have my own things to contribute to. And also I've realized I think there's like things that I know that are arcane that will only matter in moments. So it's kind of like sinusoidal, and society kind of moves across the sinusoid, and when it intersects it's valuable, but there's going to be many times where what you have to say is just meaningless. And then if I start to reach, I'm going to be this person that's kind of faking it, and it'll come off, and I'll sound like a fucking idiot. So I just think everybody, you kind of have to just be in your lane and just realize like the earth has these undulating things that it needs or requires, and when it intersects you'll be there, and I think that that's okay, but it's hard to know that.
Yeah. Tell me a little bit about the group dynamic of the four of you.
We are what we are like in real life, and one's definitely on the autism spectrum. One's definitely this pugnacious Brooklynite that doesn't want to be told that he's not good enough. One's kind of like a very eager beaver overachiever. One's like an insecure immigrant type. It's like we're all actually like very typical.
We're all archetypes of like these personas that have existed now, and you can point to so many people in your own lives. And so I think we bicker like a family. Sometimes I'm really mean to my sister. You know, my kids are sometimes mean to my other kids in ways that I just think are insufferable. But I don't know, it's kind of like how families communicate, I think.
Has anything come from the show really positive or really negative?
I think the really positive thing, I've probably been cancelled, well, attempted to be cancelled at least once in a really big way.
Because of something I said on the show, and I would say that that was incredibly positive for me because of what it taught me after the fact. I didn't understand how the game was played.
Can you give me the specifics?
Yeah, the whole story was Jason was talking about human rights or something like that, and I essentially said something to the effect of, 'Stop virtue signaling because you nor anybody else in America are willing to actually make the substantive changes if you actually thought this was an issue. So you say it's an issue, but your behavior betrays it being an issue. And as far as I'm concerned, it's below my line.' That's the thing that became a meme, or like there's a picture of me talking about the Uyghurs in China specifically.
Well, I said the uncomfortable truth because it's true, and it's like, you know, I think it's very dangerous to say things matter when they don't matter.
Yeah. Well, when you don't treat them like they matter.
Yeah. So like, you know, you have to reserve your words, otherwise you become the boy who cried wolf. This matters. That thing matters. The other thing matters, and you do nothing about it. Nothing matters.
And then you're an unserious person. And so are we an unserious society, or are we just caught up in fringe politics? So I got frustrated and I said something, and I personalized it. And then, you know, at the time, like I remember the sequence of events was like, I think that was like on a Thursday we tape, typically it comes out on a Friday. It was Martin Luther King, so it was a long weekend. Some guy clips it. It starts to go viral. People start to post about it. I was a co-owner of the Warriors. They are part of an organization that has an incredibly complicated relationship with China. So then the Warriors distance themselves from me. And, you know, my initial reaction was very reflexive: 'These guys are spineless.' But really they're doing the right thing just to manage the fallout because it's like, you know, 'We appreciate your capital, but we're not getting into this.' Which I didn't understand then. I get now.
And then the White House put out some comment on the Monday on Martin Luther King Day, which I thought, 'This is crazy. This is intense.'
The White House put out a comment about you, something you said on a podcast?
Yeah. On my own podcast. And so I was like, 'What the fuck have I touched here?' Like, 'What is going on? Insane.' And I remember a friend of mine texted me, and he sent me this study which was when you look back at all of these moments online when you're kind of like in the public firing line. He said if you believe it, you should never apologize. Never ever apologize. Ever. And then he gave me this like study that showed it. Like even if you said something reasonable and then you apologized, you just got run over. I kind of stood my ground and I said, 'Yeah, you know, may have said it indelicately.' And this is before cancel culture was cancelled.
And so it was in the throes of it, and so I felt it on my skin, and I realized this is not a way a sustainable society operates.
Did that make you want to dig in harder?
No. Initially I wanted to go in because I felt like, 'Oh my god, like this is really bad. What have I done?' And, you know, I can't believe people are looking at me this way. And some people I think were probably joyous like, 'Yeah, finally he's getting some of his own shit.' And it was very hard to deal with, but in hindsight, I tell you, that's the greatest gift that I've gotten from the pod is that one moment because it was like all these important things all at once that showed me where we were and kind of where we needed to be. And if I'm trying to make the point, and the point is valuable, I think it's really important to actually make the point, I could have done it in a much smarter way. I also could have taken the time in post to really think about how I threaded the needle, and I would not because I was a little cavalier about it, you know.
Did you even know it was an issue though in post?
I didn't even look at it in post. I was more of like, you know, the golf analogy, grip and rip. I would walk in, I would do it. I'm like, I thought it was cool for me to say, first cut, go.
When you said it, did you think, 'Oh, this is something that's really gonna...'
I thought it was benign. I had gotten frustrated at Jason. Like, this is a family conversation. I'm fighting with my brother.
He said something, I got mad. 'Shut the fuck up, Jason.' And I just left it. And I thought, you know, just kind of move on. And it became so much more than that. But it's a great moment because it's like it just allowed one side to take the side of 'you can't have serious conversations anymore.' It took the other side to say it's really important to keep saying these things even if it's not true. Don't buy the iPhone if actually you believe in this. Don't go to Walmart and expect these goods to cost 99 cents. They are being made in China, and don't for a second think that you know how they're being made. So either understand the hypocrisy and live with it and be honest about it, and then have like the moral clarity to say this is wrong but I am indirectly supporting it. I don't like, I think people don't like the moral ambiguity of that. They don't like that. And so it's a real gift because I lived it, and being in the middle of it is very different than looking at it.
And you realize then you can't be cancelled. So, it's an enormous gift to know that you cannot be cancelled. It allows me to be a little bit closer every day to my truer and truer self because whenever I get afraid, I can go back to that moment and remember how it felt like, but then remember what the outcome was.
Yeah. Have you been able to mentor any people through things like that since?
Yeah, since then. I keep telling them all the time that I go back, that is a very incredible thing. So that was I think really probably the most positive thing.
Which again, from the face, it would seem like the most negative thing turned out to be the most positive.
Exactly. And I think the most negative thing about it is again, it's just an hour and a half a week, right? So then the intimacy that you have that you sometimes is not real, meaning like we will talk about moments, but they can be so viewed out of context that I think it's easy for us to oftentimes look like detached dilettante kind of rich guys opining, whereas the truth of it is we are four guys, we were all born into nothing, three of the four of us were born here, we were all immigrants to America in every single which way, none of us were given a fucking thing. We all made it in a way that you would be proud for your kids to make it. And then we've all enjoyed the trappings of that success to various degrees. But I think that the way that in an hour and a half sometimes the way that we joke with each other, the way that we do in private, when you see a window into it, if you're just a voyeur or a random person that observes that in a moment, I definitely think it creates these perceptions, and a lot of times those perceptions are deeply incomplete, and then that carries with them, and then it comes back to you later, and that's negative. And then most people would say that's positive because like you look like you're on top of the world, you have quote unquote, you know, notoriety, fame, whatever it is, people see you that. But the downside is they don't really know because you can't, you know, and you're not supposed to carry a fucking placard on your neck that says, 'Hey, I grew up on welfare. Hey, my dad beat the shit out of me every day. Hey, I worked at fucking Burger King when I was 14.' You can't do that. That's not real. And so you get into these misperceptions. And I think these misperceptions can be complicated.
How is the notoriety different than you would have thought it would be?
This is going to sound really weird, but like society works at the intersection of like humans' incentives and the technology that we use. Meaning, think of how much of our world, the knock-on effect of the world, is because of how people's perceptions are shaped. But those perceptions are shaped overwhelmingly by social media. That is a brittle algorithmic way of taking an issue and either highlighting it or not. But the thing is, if you understand how the algorithm works, you can then by definition manipulate what is perceived to be important, what is not. And as a byproduct of that, you actually are shaping in an otherwise abnormal way what society thinks. When you look at, for example, an AI, or if you look at the core structural algorithms that we use inside of Facebook or Instagram or X or Google, the best way to describe it is these are fame weights. They're oriented around attention. In fact, the most critical technological breakthrough in AI which allowed us to have this current set of experiences that we live with today, the seminal paper was called 'Attention Is All You Need.' And it's like, well, if you just took that as a statement and you said, 'Is attention all you need?' No. You'd say no. That's like, in fact, all kinds of deleterious outcomes will happen if only you focused on attention.
Right. But that's how we have framed this current era. So we are unfortunately fame-oriented. It is a critical underpinning of how society works. And being a part of that, I think unless you're super vigilant about the fact that it's going to lead you into places that may not be where you want to be, you're going to get sucked into it. And I think that's probably like a very negative outcome of this. And most people would never because you think, 'Oh, it's cool to be like somebody sees you and you take a picture.' I think that is as it is very cool. And it's cool to have the benefits that come with recognition, but I think most people do not understand that everything has a cost, right? It's an equal offsetting reaction. Like whatever you're getting as a positive, there's an equal and offsetting negative reaction. And I think the negative thing is that we are all part of a fame and attention machine. And I think it has the potential to really fuck up society.
Based on your experience of being cancelled, do you think that there's a cooling effect in society where people are afraid to say what they think?
Yeah, I think that there's been a long period of time where you can't really say what you think. And but here's the crazy thing. I think what I've also realized is most things, it's like a bell distribution, right? Where like you have these crazy crazy long-tail things on the left and crazy crazy long-tail things on the right that one could say, most things are in the middle. The problem is the things on the edges causes people to not even say the stuff in the middle because they don't know where the boundary is. That's the chilling effect. And so what cancel culture does is, you know, this is why like, you know, Elon and all these others who are owners of these platforms, why they say the most important piece of information you interact with is the one you disagree with the most, and gauging your reaction to that is so critical. And I think what he means by that is if you can talk, if you're like on the far left and you see something on the far right and you can disagree but tolerate it, or you're on the far right and you see something on the far left and you disagree and tolerate it, what that tells is most of the rest of us who are mostly in the middle plus or minus a few degrees how to talk about everything that's in the middle. And it's everything that's in the middle that actually governs your quality of life. These fringe far issues affect incredibly small populations of people, yet they take up all the noise, and if you weaponize them properly, it actually suffocates the ability to talk about the 99% of the stuff that is in the middle.
And that everybody agrees on.
And that everybody agrees on, or you can actually have a debate on.
You know, hey, you want universal healthcare? Okay. Hey, I want waste, fraud, and abuse out of the government. Okay, let's find the middle ground. Right. Hey, you can't even do that because those two issues, which are actually very benign issues, they get transacted on the same ledger where you talk about immigration and ICE and trans rights, and those are two totally different sets of issues.
And you personally have a universal healthcare experience because you come from Canada and now you live here. What did you experience about the strengths and weaknesses of the universal healthcare?
I think it's important to, you got to look at it from a point in time. When I was growing up, my father had a whole series of heart attacks, and he was very unhealthy, drank a lot, and was a diabetic when he was 42, and basically he died when he was 72. So those 30 years were like a decade of pills, then a decade of insulin, then a decade of dialysis, and then he cardiac arrested and died. So, if you had to manage your life in the United States with a 30-year chronic illness like that, it would have been a shitshow. We would have been bankrupt. And I mean, we were so poor anyways, but he could go and get care. So, my perception of universal healthcare was very positive. And then I came to the United States, and then I was lucky enough to have healthcare. Amazing. But then you see what's happened since in Canada. My mom is 85. If she wants to get an MRI, it's now a year and a half wait to get an MRI. Nobody wants to admit that that's true, but it is true.
What are the odds of most people who are waiting a year and a half for an MRI dying in that year and a half?
I think probably quite high. I think it's very sad to note that we had universal healthcare but not legalized euthanasia in Canada. We've maintained a perception that we have universal healthcare, or they have universal healthcare, but now they've legalized euthanasia, and I think it's quite crazy to see that there are so many people that choose to take their own life in a country that theoretically proposes completely free and available healthcare. I think that that's just a really important distinction that somebody needs to explain to me because I don't understand why that is, because I think there's something about that that's linked where you have these issues. Maybe they're acute, maybe they're chronic, but maybe you just see finality of your life as a simpler solution that I find absolutely unacceptable. Should you be able to get an MRI in 3 weeks? Yeah. 3 days? Yeah. Should the MRIs take an hour? No. Technologically, we know how to make these things so that they're in 10 minutes. Why don't we? And that goes back to this whole stagnation of Western societies. It's like we wanted flying cars. Instead, we got, you know, 140 characters type thing. So, you can't take a label of a social program and use it to launder the fact that we've actually stagnated. And we then have created these programs to deal with the outcomes of that stagnation. Yes, we have a universal system, but sorry, it's going to take you a year and a half to get an MRI. Yes, we have this great way to take care of you. It's completely free, but oh, by the way, you can also choose to kill yourself. That doesn't make any sense to me. Whereas in the United States, we have a different problem which is in a moment in time where the United States tried to thread the needle, it made a fundamental mistake, and we can't seem to admit it. And you have to be intellectually honest on one very narrow point which is when they implemented Obamacare, there was a single thing that he did not study well enough, or his team did not understand, or they lobbied to include, which has had horrible negative consequences to the United States healthcare system, which is this concept of capping the medical loss ratio. What does that mean in simple terms? When you have a business, let's say you sell a good for $100, your incentive is to make that $100 good for $20 and capture $80 of profit. What they said was your margin is capped at 20%.
Most you can make. So you want to sell it for 100, it has to cost 80. Find a way to spend 80. Well, what do you think these guys did? They were like, 'Well, I want to make $200. I want to make $2,000. So, okay, I'm going to charge 4,000.' And if you look at the prices that have made the medical industry so completely unaffordable in the United States, it's that simple decision. And so, undo the decision. The problem is that the messenger there, I think so many people dislike, they have TDS. But Trump put his finger on that and said that's stupid. He said that as an outsider, and even in 2016. Now I wasn't listening as carefully in 2016, but that is a legitimate thing that if you fixed, you would change the financial incentives of all the people in the system. And instead of saying universal healthcare, you have to go one level deeper and say how is a system executed so that it's going to work properly for people. And you can't use universal healthcare as a way to deliver care in 3 years where the alternative is euthanasia. That's not a compassionate system. I think we're much better off just fixing the current system and just saying, 'Okay, sorry guys, that was a mistake, and we need more free market competition here.' And I'm sure the $3,000 MRI is going to go to 100. Here's a pathway that we're going to prove things that can be scientifically proven in 6 months as opposed to 6 years, and you'd probably find somebody build an MRI machine that can do it in 15 minutes.
But why would that be a political issue? That just seems like it's good for everybody.
But today it is a political issue. If there's a solution that's good for everybody, the best thing that could happen for the world is if aliens dropped in, because then you wouldn't care about Republicans versus Democrats. You'd care about humans versus non-humans. And you could make these decisions. But today, we're highly tribal. You have to be on one line or the other, and I'm going to choose which side I'm going to be on based on a whole series of factors. You're going to choose as well, and we're going to choose to disagree because that's the sport, and that's a shame. And you find very little commonality. So like, you know, if you go back, at least in the United States, it's now become quite predictable when you go back three or four presidencies now what happens since Clinton. So if you look at Bush, Obama, Trump one, Biden, Trump two, in these four-year windows, except when you're a president for eight in the case of Bush and Obama in a row, right? When you first get elected, you're basically given one big shot on goal, and you're like, 'Okay, in the first two years, it doesn't matter who it is. Go after it, and we basically will get it passed, whatever it is.' In Bush's case, it was crazy to say, but global war on terror. It was the Iraq invasion. It was the Patriot Act, which is insane. Insane in terms of civil liberties. And then after that, it was relatively stayed. Obama comes in, gets slammed with the global financial crisis in 2008. Obama has to unwind that, but gets a massive shot on goal, and he chooses Obamacare. Gets it done in the first two years. But again, just like Bush, Obama loses the mandate, and then the next six years, they're just kind of swimming sideways. Trump one had one big shot on goal, got a huge domestic economic package passed. Biden one had one huge shot on goal. It was a sustainability tax credit, long-term investment program around these very narrow kind of technologies. And then Trump two was essentially resetting the body politic with respect to tariffs and then refining some of the economic incentives. So the reason why more doesn't change is that there's this dynamic where you get one shot on goal, and your calculus, whether you know it or not, is more like, man, what is the thing that I can do that has the best chance of helping me in the next two years going into the midterms and then, you know, getting reelected. And I think in that calculus it's hard to get people rallied around this other thing. And then when you pick something like healthcare and say we're going to change the MLR, it's too esoteric, you know, it's like it seems narrow. It's hard to explain. It's hard to communicate. And there's enormous financial incentives now to keep things the way they are. And I think that's why things don't change.
Tell me about incentives. Is incentives the best way to understand how everything happens?
Yeah. Is there any downside to looking, considering only incentives?
There's no downside. It's not a complete picture, but I think it really helps me at least understand why is this thing happening? Like I think at the end of the day, you know, we're going to go through this really important change from being overwhelmingly psychological in terms of how our society works to overwhelmingly deterministic as AI becomes more and more part of our society.
TBD. I think there are certain systems that will benefit profoundly from determinism. Like I'll give you an example. The United States government processes half a trillion dollars of healthcare payments a year. The best guess that I've seen online is that about a hundred to $200 billion dollars of that is just waste. The downstream...
Is it fraud or is it waste?
They're two different things. I do think fraud exists. Maybe fraud is more like 25 or 50 billion, but most people are not spending most of their time trying to figure out how to break the law. But most people, like I'll give you a benign example, are given a job as a Medicare coder in a hospital, and they're told, 'Hey, listen. When Rick comes in for an MRI of the knee, here's how you code it.' And now you have like, you're tested for your ACL, your MCL, you also are tested for sciatica, and now you have like, you know, you're upcoded. I don't think that that's fraud, but I do think that that's wasteful. And maybe there are systems that can deterministically be more precise and say, 'No, Rick's coming in for this. This is the code. We're going to reinsure him once,' or you know, those kinds of simple decisions like that. I think they would save a lot of money. It would have a very long-term impact on our system, which is, you know, right now our system is not trust but verify, our system is reject and you fight and you figure it out. So determinism in a system like that is really healthy because I think all of us will feel much more safe that things are working in a very logical way, you'll be able to explain it to yourself. Other systems, I don't know. I was on Rogan like a couple years ago, and I mentioned this example which seemed far-fetched then, but it's probably going to happen now, where I said, you know, it makes no sense for policemen to be first responders in a crisis. It completely makes sense for droids and for robots to be the first responders, and you can start to program them to really understand how to de-escalate situations because, you know, it's sort of like the entropy of human-on-human chaos is cut in half because it's just human-on-robot, right? And then determinism is great because now, you know, cops are much more likely to take the first action that's the just action. That has huge implications to how entire neighborhoods are policed and behaviors, and then your trust in the system and your ability to deploy police everywhere. Is that good or bad? I mean, there will be people that think that's really bad.
Yeah, I could see both sides.
Yeah. Yeah. I wonder if I was going through some difficult time if I would be as comforted by a robot trying to deal with my situation as a human.
I think that if I was totally stressed out or totally afraid, I would be very scared if I thought that the human couldn't empathize with me. I would feel safer personally, me, with something that was more deterministic.
That was like, 'All right, Jimoth, what are you going through?' It asks me 15 or 20 questions or whatever, and just can just de-escalate because it's programmed, because we know how to do that. Like if you talk to the best kidnap negotiator, he or she knows how to de-escalate, and we can learn from that, and we can make that programmatic and predictable so everybody has access to that. I don't know. That to me sounds like better.
What are your thoughts on prediction markets?
I'm just so torn. I think it is a sign of real societal decay. The fact that they are popular as they are, the fact that you spent all this time betting on everything, it's just a different form of entertainment.
Is that how you think of them?
It's a dangerous form of entertainment. I think there's a different aspect of prediction markets, but those are financial markets, which are truth machines. I think the way that it would be sold to you and I as like a societal good is that these are truth machines that induce insider information. And I think that's what the creators of these markets would tell you. And why? Because you can't resolve an unknown market like that in the absence of inside information. You have the two sides. They should theoretically be equal. The fact that there is an actual imbalance between one and the other side is the sign of the actual truth, and that necessarily has to come from inside information. Somebody is a sharp in that market, and everybody else is a square. So I understand that logic for why now that's like super valuable. But it's such a slippery slope from there to like you're betting on whether the player in the Super Bowl flips it with his left thumb or the right thumb. The shoelace comes untied. Like it's like, what the hell is that? That's just degenerate gambling.
If you were looking at trying to understand what a likely outcome was for something that's going to happen in a month, would you more likely trust what you find on a prediction market or what you read in the New York Times?
Oh, overwhelmingly prediction market. Overwhelmingly.
Well, overwhelmingly the prediction market. So, in terms of getting information,
That's a different question. How would I answer a question that I had for a month from now? I have my own process to get to first principles opinions on things that I think are important for me. And I look at neither.
So if I'm curious, I usually start on X. I go to the search bar, I type it in, and I just see a stream of stuff. And I will then probably spend an hour consuming all this information. Then I'll go to a couple of the AIs, and I'll have structured questions that I would ask. Then I would probably go to Google and just do a web search to see if there are authoritative things that I've missed. And then I go back and I try to write something that's less than a few paragraphs that just kind of explains what I think. And then I leave it for typically a day or two. And then I come back and I read it, and I'm like, 'That's fucking stupid,' or I'll be like, 'That sounds right. There's like something there.' And so it's like a very intuitive thing. Like I've been very lucky that I have this weird alchemy in my brain sometimes that helps me kind of just like write shit down that's, I can't explain it. It's just like this thing that shapes. But so much of it is not right. But I really give into that process, and I'm okay with the wrongness.
Yeah. Do you trust your intuition?
I really trust my intuition, and that's an incredible thing because I wrapped my intuition in tons of insecurity, and so I would pervert what I saw, and that's caused huge mistakes in my life that I've made that have cost me tremendously, mostly financially. So in the end it's not that important, but it's important as a learning lesson, and in that it's like essential because I think like everybody is given gifts. Some people have no intuition, but they have other gifts. And so, we're all embodied with something that's very special to be grateful that you have a chance to just be in that thing and feel it. It's very lucky. And so, I'm mostly in a place where I can kind of like follow my intuitions. I'm in the business of my own intuition. That's a crazy thing to say because I feel lucky there. It means nothing to anybody else. But before I would kind of like, you know, pervert that intuition with my own insecurity.
How did you find out that you could trust your intuition?
I mean, look, there's a very incredibly famous clip of you, you know, with Anderson Cooper where you're just like, 'I kind of just feel it. I'm not musical.' And then like it became a whole meme, which by the way is also like, memes are very powerful because they are little nuggets of truth, everlasting truth. My takeaway from your meme is you have to be very comfortable in your intuition, and then you have to measure your intuition. And the way that I inferred that from what you were saying is like, you know, you're there with Jay-Z, and I think it was like, you know, maybe it was like 99 Problems where you were like, 'I like that. Like I like whatever version of that.' But you were right because in that sinusoidal wave, society was intersected with what you thought was right in that moment, and it was a fucking huge hit. But that's a quantitative validation that your...
intuition was right. In my world, it's similar, but the measurement is different. I made an investment. I started a company. I created a product. And every now and then, those things are massively right. Massively. Like decadillion dollars, right? And it's not that the money is important, but it's a signal to me that I'm on the right track.
Your intuition served you.
And then I then but then I have it on the list where I can see where all the other times my intuition was wrong. And I'm like, but as a body of work, that thing is right enough. I got to go with it. And so I I'll be sitting there in product meetings and we're like, you know, trying to figure out the shape of a product or like we're trying to figure out like how do we start this thing and get off the ground or whatever. And it's not rooted in anything other than intuition. I think
how does it relate to taste?
This sounds incredibly arrogant to say, but I have developed incredible tastes.
My wife. She's a pain in the ass. She is such a hard ass on so many dimensions. She's up my ass on everything. Italian raised in Milan, grounded in like the Italian education method has. I mean, it's like if you think about it, it's like you're educating the Michelangelos and the Dainci, but you know, along the way, you're educating, you know, the Natalie Dump. That's my wife's name. And it's crazy because they have a broad-based education which amplifies all of these senses, you know, like the Italian language. I think there's something important about this. Like when you're taught a language where when you speak, there's nine different ways of saying the word tasty. And when your brain processes these nuances, you become extremely detail oriented. So as a culture, they're very detail-oriented. So when you see the things that they make, it's beautiful. And when I met her, I had my intuition wrapped in my insecurities. So, what did I look like? I was technically an owner of a basketball team pretending to be like dressed like a player. You know what I mean? Like horrible ripped jeans with leather patches and all these sweaters with these logos and all this. And she's like, "What is all of this?" And I was like, "Well, what do you mean? Like, I have a stylist. You know what I mean?" And she's like, "This is all" or like my house or like all these things that were expressions. She's like, "This is not your intuition."
You were copying what you thought was cool around you.
Exactly. Exactly. And then like I got a normal haircut. Literally like a normal haircut. You know, my haircut was a way of trying to belong. I got normal clothes. Everything didn't have a label. And for all this time, I was like very insecure. And so it started in these small ways. Then it's into business. She's like, "Why did you do that deal? Why did you make that investment? That thing seems way too oversized." And I was like, like I was like, it's hard, man. And I'm like I knew there's a reason why she's in my life. And so she helped me unbuckle my intuition from my insecurity. I still have this insecurity. It's a huge This is my dark passenger for me. But then on my intuition, she's like, "Why don't you express it in a son's insecure way?" Oh, you you don't need to make an investment that's $200 million. You can do 25. No, I can't. People will think I'm poor. What are you talking about? Calm the down. What are you doing? Think about this as like you have to make this thing successful. You want to save your money so that if it works, you can give it more oxygen. If that doesn't work, if you believe in the idea, you want to go chase the other thing that so that that could work because you care about the solution. And she's like, "You're not giving yourself any optionality." So, I learned how to like have some taste, right? This is good. This is not good. This is oversized. This is undersized. This is wrong. This is right. This is a good bet to make this creates the right sensation. Like, and it's it's been hard for me.
Would you say that she had a better understanding of what quality of life actually is?
She has no ego and I have a huge ego. And
I think that was my response to being poor, to being fat when I was younger, to not having a lot of experiences with women, you know, when I was a kid. And so my protective mechanism became that ego. And then when you when you imbue that with accidental success or success at an age where it's not deserved, it's like lighting a brush fire and it takes it takes over.
You believe the hype, but she's just built differently. She's like, "I'm a steward of a business. I make drugs for rare diseases. You know, I broke my back when I was 11 and I was in traction and then I had to kind of relearn how to walk and I have to manage what I eat because otherwise my body will get inflamed and my body shuts down and I can't I'm in so much pain." She has no ego that way. So, she's just like is like very like sees the thing. And then more than anything else, she cares about me so much that she sees the visual I have is like it's like you close your eyes and you see energy and she knows when my energy is off. She can just feel it by my words, even my tone of my voice. And I can do that now for her in different ways. I'm learning how to do that. Uh which I think is like very cool. And then I find I can do that now in a few cases for my friends where I've been able to kind of like, whoa, hold on. I see I I've seen this before. this was me. So, you know, taste is weird because like you can define it as a very superficial thing. I think it's quite profound. It's very deep. It's where your intuition, your emotion, your selectivity, and your judgment all comes together. And you're like, "This is really beautiful. You know, this should exist." And interestingly, taste is actually very non-judgmental, which is weird because like I thought what taste means is that sucks. That's not taste.
Taste is the part where you're like, "That's amazing." So I can hone in on the thing that's beautiful, that's right, at the exclusion of this stuff without denigrating that stuff.
Beautiful. Do you think of yourself as a gambler?
Always. I love gambling. Why? One is very superficial, which is I don't think I deserve to win. And so there's a weird comfort in losing. And I think if you talk to a lot of gamblers, we all are a little broken this way, which is we have this weird sadistic joy in losing. You nobody will ever say that to you as a gambler, but real gamblers love the the churn of losing more than they love the high of winning
because it reinforces what you believe about yourself.
It tells you, I think, that you're not that worthy.
It creates a pattern and a cycle in some people that's very comforting. But then I think like there's a part of gambling which is incredibly useful which is like you're a version of yourself and there's a theoretical version that you can be and let's just say you're like a 20 out of 100 but you can theoretically be a 100 out of 100 in terms of you're the best version of you. Whatever best means to you. You are not going to get from 20 to 100 without taking some shots that take 20 to 10. Just not going to happen. You don't go 20 to 21 to 22. It's there's no straight line path there. And gambling is this really interesting way of training your mind to be able to take those bets and processing the loss. And I don't love losing, but I can process losing and I can deal with it and I can move on from it. And part of it is because I started from a place where I thought I'm supposed to lose. But as I get older and as I got more comfortable with it, I'm like, I can manage this. I know how to take risk. I know what the losses are meant to teach me. Most people don't understand that. And I think they think about gambling as a negative thing. And specifically what I mean by gambling, by the way, to be clear, is poker. I don't really gamble in any other way. I don't sports bet. I don't I don't do that. I don't play blackjack really. Every now and then in the casino, but not really. I play poker. But it's this incredible journey of taking risk, sometimes being right, sometimes being wrong, processing wins, sometimes you did the right thing, but sometimes you got lucky. Processing losses, sometimes you did all the right things, sometimes you got unlucky. And staying in a process, that's amazing. Balancing intuition with data and your judgment and having taste. Where does taste come into a poker game? You can be incredibly creative. And why is that? Because the number of probabilities in how you play any sequence is quasi infinite. And so there's a real element of creativity in the game. It's like chess but on super steroids. You know, people talk about creative chess players. Bobby Fischer, like how did you do that? Like how did you find these paths in the middle game? And Bobby was incredibly creative. Poker gives you that outlet, too. But it it requires some taste. And there are some incredible players that are just so creative and you're just like how do they do these things?
How much does luck play in in poker?
I think as the number of hands go down the amount of luck goes way up. So at one hand luck is I would call it 100%. And at an infinite hands luck is zero really. And so the question is where are you in that spectrum? And probably the real demarcation point is maybe after kind of 10,000 hands. It's mostly skill. So this is another crazy thing. Poker is not many many many games. It's one infinite game.
Maybe you play on a Wednesday. Then maybe you don't play for two months. Then maybe you play in a year. Then you play all part of the same. Then you play seven games in a row. It could be different blinds like different risk levels raw one game. It's the same ace king you're getting in the small game is the big game. It's the same pocket twos. How are you reacting to this? How are you managing this? Do you have a system? Can you maintain discipline under pressure? Can you find creativity? There's very few things in life where you can have an infinite game. And that is an infinite game with yourself. And so I tell everybody, play poker if you can learn to love the game. It's an infinite game against you.
I imagine you know the statistics as you're playing of what's likely to happen.
Yeah. Okay. Knowing the statistics, do you ever make a choice where your intuition tells you to go against what the statistics are telling you?
I think life is about these very important deviations. Poker is a good representation of that. There is the path that's well defined, right? I guess maybe the Robert Frost quote. And then there's the path less traveled. And there's all kinds of situations where you want to understand what the conventional wisdom is and why. And more than I would say 80 to 90% of the time in poker, the right thing to do is to follow the conventional wisdom. And in life, it's the same thing. Okay, I graduated high school. Conventional wisdom says go to university. Conventional wisdom says study finance or accounting or engineering. Then conventional wisdom says you get a job at like a big consulting firm. Conventional wisdom then says, you know, go to MBA school. Then it says get married, have two kids. All conventional wisdom. And by the way, that's a very legitimate and quite a dignified life in my opinion. And I think so many people should be proud of that life. And then life gives you these small little egresses off that path and you have to weigh how to make that decision and you have to get over the loss aversion that is required. That's the key insight when you're on a path that's largely defined and you're about to go off. The biggest thing that most people will struggle with is, "Oh my god, I'm giving up all of this stuff." You look forward. You think about the sum total of all of that value. You discount it back. You may not know you're doing this, but you're like, "Shit, I'm going to give up all of that." And that's what stops so many people from deviating.
Risk aversion. Loss aversion specifically. So in poker, just to go back to a very narrow example, you'll be in very specific situations where you're given the ability to challenge risk aversion and loss aversion. you're able to go and say, "hm, I know the conventional wisdom is this. The result should probably be that, but gosh, I just want to follow my intuition here on this. I'm going to zag when everybody zigs." Now, the problem is that may mean half the time I'm just going to lose everything. And then you have this critical question. Am I okay with that? And most people's answer to that question is no. And then they stay to the conventional path. But then the problem is there's a weird butterfly effect. You cannot live the conventional path the same way because you entertain this and kind of capitulated back to this which is effectively your way of saying I don't want this but it's safer than that.
And instead what you're supposed to do is go I want that or I want that. Choose where you want to be. So I think like in life and in poker it's the exact same idea. you're going to be tempted to deviate from the conventional wisdom and it's very legitimate to explore it but you have to understand how to deal with the loss aversion and that's a training and if you can train yourself to be okay that like things did not go as what they predicted okay what am I going to learn from that that's an incredibly useful thing to give a person I'm sure you've made records where you're like I followed my intuition and it sucks it's like not good
ah You wouldn't say that.
No, cuz I follow my intuition until I think it's great. Now, other people might not like it.
So, it depends on what the metric of success is. If the metric of success is it got on the radio and a lot of people bought it,
I don't play that game. I'm focused only on staying true to the intuition all the way.
When you go back and listen to some things that you thought were great, do you still think they're great or do you think
I think they're great for what?
They're inviably great over time. It's like immutably great. Yes, they're immutably great in the way that when you put what happened to you today in your diary, if you look at it 5 years later, that is what happened. It's true to the moment.
Yeah, that's what I mean. It's true to the moment, but is it true in the future?
Well, I wouldn't question it, right? In my case, once it happens, I assume that I know I did everything I could do to make it the best it could be, right? And when I listen back to it now, it reminds me of that that, right? It does.
So your mind doesn't work in the other way where you're like, "Oh, I would have changed this. I would change that."
See, that's incredible because that takes I think a lot of self assuredness. I don't have that. I unfortunately am constantly like, you know, we say in computer science, I'm diing. I'm like thinking like the what the version of it would have been today. And that's very like it's problematic for me because I think like it it occupies a bunch of brain cycles that are unhealthy and wasted.
But I would like to get to where you are. So when you're playing, there's the conventional wisdom and then there's your intuition that says to go the other way. What percentage of the time going the way that you choose to go was in fact the thing to do?
I don't think that I'm heterodoxical, but I think I am unconventional. Meaning I don't really care what the orthodoxy nor the heterodoxy is. I just think like I think I like what I like.
And of that I would say I'm probably 80 to 90% wrong.
And is the 10% right enough to make up for the 80 or 90% wrong?
That 10% is I mean it's changed my life for sure.
Yeah. Well, let let me say this way. I think that of the 10% I haven't yet been right in the way that I want.
Mhm. You know, like I look back, like if I look at my career as a lens, I've had some hit records, a bunch of hit records, but I've not made an album that I'm really proud of. And I look at the studio teams in which I made these records with, and none of them are are with me anymore. And so I wonder to myself like am I just this procurial pain in the ass or can I actually build something a little bit more enduring? It doesn't happen by aiming at it. I'll say from my experience.
it comes from being true to how you see it. And then once you're true to how you see it, either other people see it that way or they don't. And that's totally out of your control. Okay. So, I think that sometimes I like I daydream of the shape like I can see the shape of what I want to make, but then I can be so sometimes hard to deal with in the making of the of the shape. I would love to make a shape of something where people are really like, "God, we made that together."
But you're still in the outcome game. And what I'm saying is
the artist perspective is in the making game. It's not in the outcome game. the outcome happens. So you can't say I want it to accomplish these things and then make a thing hoping it accomplishes those things. That's not the way to make the great thing. The great thing comes when you're purely making the great thing just for yourself for you. You can't wait to show it to your friends cuz you think they'll like it and want to use it. It might even change their lives, right? But it doesn't go beyond that.
I mean, when you say it, I I have an internal panic and and I'll tell you why. My internal panic, Rick, is like, "Fuck, I don't know how often I've really felt that way."
Yeah. Because you still care what other people think.
I think so. And then it also says to me like, "God, like maybe I'm just still so primordial. Like, I'm just not as evolved as I want to be or think I am."
