THE KNOWLEDGE PROJECT #81 Jason Calacanis

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THE KNOWLEDGE PROJECT #81 Jason Calacanis THE KNOWLEDGE PROJECT #81 Jason Calacanis fs.blog Shane Parrish: Today I’m talking with Jason Calacanis, tech entrepreneur, angel investor, and so much more. This conversation focuses on poker, investing, decision making, the culture of Silicon Valley, wealth distribution, and how systems enable or forbid. I just want to say this episode touched on politics a little more than we normally do. It wasn’t intentional, it’s just a by-product of the organic conversation we had. It’s time to listen and learn. Jason, so good to have you on the show. Jason Calacanis: I’m a big fan of your work. Thanks for having me. You’re a high stakes poker player. Can you talk to me a little bit about what’s going through your mind when there’s a lot of money on the line? Yeah. I play higher stakes poker these days. I started playing poker in New York with my friends at a place called Forlini’s down in Chinatown, an Italian place below Little Italy. We would just buy in for like 10 bucks and people would just get drunk real quick and people didn’t know if a flush was better than a straight, but over time I went for bigger and bigger tables and learned a lot about trying different styles of poker. And so I made lot of friends in the poker community. I’m good friends with Phil Hellmuth and back in the day Annie Duke, and really just loved the game and what it teaches you about taking risk and what’s an intelligent risk. And it’s very analogous to angel investing in many ways, and also not. It’s a very interesting way to learn how to take risk and to read people and to understand situations with a little bit of math involved which if you think about what I do for a living now, angel investing, it’s very analogous. I have to read people, I have to take risks, I’ve got to take intelligent risks, and I only make money if I’m taking risks on a very consistent basis, right? Poker, people have this idea that there’s this big advantage people have. Sometimes in poker people have a 51% to 49% or 60/40 advantage, but they’re playing so many hands of poker over such a long duration, that that little edge adds up over many hands. 2 FS.BLOG | © 2020 FARNAM STREET MEDIA INC. And that’s why you see sometimes the world’s greatest player like Phil Hellmuth losing over and over again because yeah, he might be 60/40 versus somebody which over time means that person’s going to lose millions of dollars to him but you might not see it in a particular hand or in a particular five hand run or a 10 hand run where two players are playing against each other. Well, let’s double click on that for a second. How do you get feedback then when you’re right or wrong, because you could play the hand perfectly and still have a bad outcome. Yeah. And that’s why when Trump was at 15% I made a bet with my friend that Trump was going to win because, and I think a lot of people were shocked when they saw Trump won. And they’re like oh my God, Trump won. He only had 15% or he’s only 20%. And it’s like, anybody who’s ever had aces and had them cracked knows how often 20% actually happens, right? It’s like one out of five times, it does happen. That’s where a tilt control comes in and you’ve got to be very careful to understand when you’ve played bad or when you’ve played good. And that’s why recording your hands and writing them down in your iPhone or whatever during a session or replaying the hand and understanding the mistakes you made and being super critical of yourself is really important. And I think that’s a skill that very few people have. They remember their wins and then they get this survivorship bias of, they hit a two outer and they’re like, “I’m a great poker player.” And it’s like well, you had a 4% chance to hit that card. You’re not a good poker player, you got your money in bad. Or I got my money in good and the other person hit their two outer, they had a 4% chance, I want that situation every time even though I just lost $10,000 on that hand, right? And so when you put money into the equation, it really does change when you have skin in the game. It really does change people’s behavior. And that’s why you’ll see the really good players try to kick up the stakes constantly because at a certain point, people’s brains kind of tick over and break and they’re like oh, my God, this is a lot of money. 3 FS.BLOG | © 2020 FARNAM STREET MEDIA INC. And once you have somebody thinking this is a lot of money I’m risking, their game just collapses and it becomes predictable because they start taking less risk and then they start playing tight. And that’s why I’ve always loved to play well below my means and not have the amount of money change the way I play. And I opt out of very big games. I was invited to all the Molly’s games in L.A. because I was living there at the time, and she used to invite me to all these games and be at the Four Seasons. “Oh, Leo’s here and Toby’s here and they really want to see you.” And I was like, “They really want to see me lose 30 grand.” They don’t want to see Jason Calacanis, give me a break. But they were playing very high stakes poker and I think they were trying to get people uncomfortable and get an edge. And poker is all about having an edge. And then you’re at that table you’re looking at the other players saying, “Which two players are better than me, which three players am I better than and which three players are as good as me.” And you want to stay out of hands with the players that are better than you and you want to get in hands where the players who are not as good as you, at least everything I’ve learned. How do you develop that edge and how do you know what your edge is? Yeah. I think being super self-aware of not only how other people are playing but how you’re playing, right? So how do people perceive me at the poker table? I think about that a lot. How do people perceive me as an angel investor? How do people perceive me in Silicon Valley, and then what advantage do I have in that perception of my role here and how do I lean into that. So people generally would look at me as a very conservative type poker player who cares about the money, which means if I take the time to bluff or I fold a lot, people expect me to have it. So when I do bluff my chances of successfully bluffing go up, but I might be laying down a lot of good hands. And what I’ve learned in poker is really, it’s about when you get up from the table because if everybody’s relatively similar in their ability what I see a lot is, there’s people who like to lose. I know this sounds like a really crazy concept, but there are people who are gamblers who love the feeling of being down. And if you’ve seen the movie Uncut Gems, have you seen it yet? 4 FS.BLOG | © 2020 FARNAM STREET MEDIA INC. No. Okay. So Adam Sandler’s Uncut Gems is a masterpiece. It’s very uncomfortable to watch if you’re not a gambler or you don’t know somebody who’s a degenerate gambler. But it is about a degenerate gambler and he has the disease where he loves to come back from being down and low. There are people who if they’re down $100,000 and they come back to zero, that’s more rewarding to them than getting $100,000 up from zero. Oh, wow. So let me say that again. Digging themselves out of a hole is a better feeling, more rewarding to their dopamine receptors than being up a hundred from zero. And I know a lot of people like that, actually. And it really is about when you leave the table. And so I did this when my wife was asking me to explain gambling to her. I was like oh, let’s go down to the roulette table. I’ll teach you the Martingale system where you double your bet every time. And I took out a hundred dollar bill. I said, “Where do you want to go to lunch?” We were at the Wynn and she said, “I want to go to the dim sum place,” I was like, “Yeah, perfect. That’s what I like.” And so I said, “Okay, look at all the roulette tables. Which one has the most number of reds in a row?” And she said, “That one has six.” And I said, “Okay, so that means nothing statistically because every chance is 50/50, right?” She’s like, “Obviously.” She’s smarter than I am.
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