Molly's Game Uncensored: The Truth Behind the World's Most Infamous Poker Game

(0:00) Molly Bloom joins the besties live in Las Vegas! (1:48) Did Jason actually play in "Molly's Game"? (3:23) Molly's background, starting the game, getting strong-armed by a famous actor, getting stiffed for $250K and losing the game (16:54) Moving the game to NYC, mob involvement, legal troubles, writing her memoir and making the movie (31:10) Best celebrity poker players, high-stakes poker archetypes, and more (34:31) Sales coaching advice Thanks to Oracle! Join Oracle AI Experience to discover how Oracle is your partner for accelerating your AI journey. https://www.oracle.com/artificial-intelligence/ai-experience/?source=:ex:sn:::::AllIn&SC=:ex:sn:::::AllIn&pcode= https://www.oracle.com/artificial-intelligence/ai-experience/?source=:ex:sn:::::AllIn&SC=:ex:sn:::::AllIn&pcode= Follow Molly: https://x.com/ImMollyBloom Follow the besties: https://x.com/chamath https://x.com/Jason https://x.com/DavidSacks https://x.com/friedberg Follow on X: https://x.com/theallinpod Follow on Instagram: https://www.instagram.com/theallinpod Follow on TikTok: https://www.tiktok.com/@theallinpod Follow on LinkedIn: https://www.linkedin.com/company/allinpod Intro Music Credit: https://rb.gy/tppkzl https://x.com/yung_spielburg Intro Video Credit: https://x.com/TheZachEffect

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Jason Calacanis?

  Hey everybody, the besties are taking Thanksgiving off, but hey, we didn't forget about you. We banked a couple of great content segments while we were in Vegas. First, here's an interview with Molly Bloom. You know, she ran the legendary high stakes game in LA and New York. I was invited to the LA one, we'll get into that. And her story was turned into the feature film and book Molly's Game. We have a great conversation, tons of insider stories, who imploded in her LA game, the best celebrity poker players, getting shaken down by the mob, how she got an Aaron Sorkin meeting, and much, much more. Big thank you to our friends at Oracle for partnering with us on this amazing VIP lunch we did in Vegas

• 0:45Jason Calacanis?

  at the Venetian. What a great hotel. Also, make sure you head over to our YouTube channel, a YouTube exclusive for the first ever bestie poker freeze out game. Who's gonna win? Chabot, Friedberg, me, or some of the world's greatest poker players, Alan Keating and Jason Kuhn? Also, Phil Hellmuth, he wound up there as well somehow. So, happy Thanksgiving, we love you, and be safe, and we'll see you all next week for a regular episode.

• 1:14David Friedberg?

  Listen, we have a guest.

• 1:15Jason Calacanis?

  We do have a guest.

• 1:16David Friedberg?

  She's an entrepreneur, bestselling author, one of Fortune Magazine's most powerful women. I didn't know that.

• 1:22Jason Calacanis?

  Oh.

• 1:22David Friedberg?

  Molly Bloom ran the world's most exclusive poker game. You probably know her from the movie Molly's Game, which we'll hear a little bit about today. But Molly's also, I think, got an amazing sense of what made her successful and the journey she's been through, I think, is a really interesting one to learn from. So, please join me in welcoming Molly.

• 1:41Jason Calacanis?

  Thank you. All right, nice to see you, Molly. Molly, what was the origin of the game? We know some of our friends played in it.

• 1:54David Friedberg?

  Hold on a second. Jason, you claimed on our show, let me just read the notes.

• 1:59Jason Calacanis?

  The notes?

• 2:00David Friedberg?

  Yeah, there are notes here.

• 2:01Jason Calacanis?

  What did I say now?

• 2:02David Friedberg?

  Apparently, where's the thing that Jason said? We were on the show, and Jason said he played in the game all the time, and...

• 2:09Jason Calacanis?

  No, no, no, no.

• 2:10David Friedberg?

  What did you say?

• 2:10Jason Calacanis?

  He said I was invited to the game.

• 2:11David Friedberg?

  No, you did not say that. Lisa, please pull the tape, and when you're ready, just raise your hand and let me know exactly what Jason said. And then Molly responded on Twitter that you did not play in my [bleep] game.

• 2:23Jason Calacanis?

  Okay, let's be clear. Molly, did you invite me to the game?

• 2:29Speaker 03

  I don't remember inviting you to the game. But here's the deal. So there were two versions of the game. There was the version where I was working for someone who would send me a list.

• 2:39Jason Calacanis?

  Got it.

• 2:39Speaker 03

  And I'm sure that you were probably on that list.

• 2:41Jason Calacanis?

  It was Jeffrey Epstein's list, right?

• 2:46Jason Calacanis?

  Okay.

• 2:47Speaker 03

  But when it was my game, you know...

• 2:49Jason Calacanis?

  I just remember the Four Seasons.

• 2:51Speaker 03

  Yeah, yeah.

• 2:52Jason Calacanis?

  Was that your game?

• 2:52Speaker 03

  It was.

• 2:53Jason Calacanis?

  Okay, so it was the Four Seasons. I remember you invited me and you said, "Toby's gonna be there, Leo's gonna be there, whatever, and they'd love to see you." And I said, "They would love to see me lose $50,000." There's no way I'm going to this game, because I was playing in a 5-10 game. But you were working for somebody at the Viper Room. The game started, you then took it over, and it very quickly became a big game. Famously, Tobey Maguire, a friend of ours, we play poker with sometimes, was part of this. And then you decided to move it to New York. Just let everybody know how this all got started for you and when you took over the game.

• 3:28Speaker 03

  Okay. So I was in college, came for the US ski team, had an accident, and retired, and kind of didn't know who I was, because sports were my identity. Went to LA simply because I wanted to be warm. I'd been cold since I was 2 years old. And ended up working for this guy, he had a real estate development company, and he said, "Tomorrow night, I need you to serve drinks at my poker game."

• 3:55Jason Calacanis?

  Okay.

• 3:56Speaker 03

  And so I showed up to this poker game, and, you know, it's A-list celebrities, like you've mentioned, but also the head of one of the biggest investment banks, a politician who was a household name, somebody from the tech world. And I get to be a fly on the wall in this incredibly compelling room. And also, you know, I'm 23 years old. This is access to information, to capital, to power. And then at the end of the night, they were tipping me in chips. And someone counted out $4,000 in cash, and I was like, "Okay, I don't know what's up with this chip-token economy, but I think I might want in." And over the next 8 months...

• 4:37Speaker 03

  I started to learn to speak the language of poker. But really, what I was focused on is how do I forge alliances? Because I knew that, I would say about three months in, I knew I didn't want to just serve drinks, I knew I wanted to have my own games. This was an incredible opportunity. I mean, it really was a Trojan horse. You could use it to infiltrate any subset of society. And I was learning about the world from some of the people who were actively involved in shaping culture. So it was a fascinating, interesting time, and it was also very lucrative. And so I decided to start my own games, and I had eight months of notes of what I would do differently.

• 5:22Speaker 03

  And I think because I wasn't a poker player, there was an advantage. Because I was able to zoom out and see, this isn't just about poker, this is about community, it's about storytelling, it's about belonging to something, and it's about escapism and fantasy. And so I really started to build on those topics. And those, you know, I wanted everyone to come into this room, and from the second they walked into this room, feel like they were in Monaco or in a James Bond movie. And so when I started the game, eight months later, you know, I was 24 years old, I didn't think these people who are rich and famous were going to come, let alone make it their home game.

• 6:03Speaker 03

  And so I would say that started the about four and a half, five year tenure of the LA game. And when we started out, when I was serving drinks, it was a $10,000 buy-in. I raised it to a $50,000 buy-in.

• 6:19Jason Calacanis?

  Yeah, that's the number I remember, and I was like, wow, those are high stakes. Because at the time, even in LA, people were not playing in those stakes.

• 6:27Speaker 03

  No, for sure.

• 6:27Jason Calacanis?

  And you really elevated the game. Somehow, the mob got involved, and the game moved to New York. Fast forward to this, because this got pretty dark pretty quick.

• 6:37Speaker 03

  It did. So I lost the game in LA.

• 6:39Jason Calacanis?

  How do you lose the game in LA?

• 6:42Speaker 03

  Well... One of the players who was making 10x what he was making in the poker game, became very obsessed with this game and wanted to talk about it all the time. And then sort of to want to kind of do things that felt wrong.

• 7:01Jason Calacanis?

  Okay.

• 7:01Speaker 03

  Okay.

• 7:02Jason Calacanis?

  Like maybe target certain weak players, maybe get some of your tip money.

• 7:08Chamath Palihapitiya?

  Like actively cheat the game?

• 7:09Speaker 03

  Yep.

• 7:11Jason Calacanis?

  Angle shoot the game?

• 7:12Speaker 03

  Angle shoot. And also was complaining that I made too much money.

• 7:17Jason Calacanis?

  Got it.

• 7:18Speaker 03

  And basically gave me this offer, "I'll pay you a salary and you can work for me. You can be the figurehead."

• 7:23Jason Calacanis?

  Uh huh.

• 7:24Speaker 03

  And I really wanted to keep the game. I was making millions of dollars legally. I was paying my taxes. I was, you know, like I had mentioned, it was incredibly exciting and educational. But I didn't want to be under, I didn't want to work for him.

• 7:40Jason Calacanis?

  Right. There's a power imbalance because this person theoretically might have been famous.

• 7:44Speaker 03

  Famous.

• 7:45Jason Calacanis?

  And the players might follow them if they boxed you out.

• 7:48Speaker 03

  Yeah, he said, "Turns out they want to play at a movie star's house."

• 7:52Jason Calacanis?

  Ah. They wanted to what?

• 7:53Speaker 03

  Play at a movie star's house.

• 7:55Jason Calacanis?

  Got it.

• 7:56Chamath Palihapitiya?

  And is it well-known who that person is?

• 7:58Speaker 03

  It's well speculated.

• 7:59Jason Calacanis?

  She never says. Who'd they speculate, J K? Toby Maguire. Uh huh. And he, the concept also was, there was this device called a Shuffle Master, which was in the first iteration. It makes the game go much faster. And three people, myself, Toby, and another person had a Shuffle Master in Los Angeles because you could buy them

• 8:18Speaker 03

  Right.

• 8:18Jason Calacanis?

  from somebody in Vegas theoretically, but they weren't available. And Chamath remembers because he got an early one and I used to bring mine to Chamath's game. He'd say, "Hey, can you bring the Shuffle Master?" He also angle shot you and wanted you to rent a Shuffle Master.

• 8:30Speaker 03

  I'll never forget going to his house.

• 8:31Chamath Palihapitiya?

  No, he, Toby, not me.

• 8:33Jason Calacanis?

  Not you.

• 8:33Speaker 03

  Not you.

• 8:34Jason Calacanis?

  Not you.

• 8:35Speaker 03

  Yeah, I'll never forget. So he was right.

• 8:38Jason Calacanis?

  Chamath renting out a Shuffle Master. I mean, he had a tough couple of years. You said there was a pretty big down drift.

• 8:45Speaker 03

  So Shuffle Masters cost 17,000 at the time.

• 8:47Jason Calacanis?

  Yeah.

• 8:48Speaker 03

  And he was right that we needed one. And so he said, "Well, how about we'll use mine? Just come up to my house and get it," right? So go to his house and get it. And then I brought it back and he said, I'm gonna need $200 for this. I'm like, you're kidding, right? Like, I'm sitting there looking at his mansion, you know? $200 a shot. I mean, and about five months in, I'm like, we need to buy our own shuffle master.

• 9:13Jason Calacanis?

  Right. Yeah, they can be obtained. So you get the game taken away from you. The game moves to New York.

• 9:19Chamath Palihapitiya?

  Sorry, so Toby takes the game away?

• 9:21Jason Calacanis?

  Somebody takes the game.

• 9:22Chamath Palihapitiya?

  Somebody takes the game away. Right. And so you're like, I'm moving to New York and restarting the game there?

• 9:27Speaker 03

  Well, I was really pissed. And I, you know, and I, it was 2008. So, yeah, I was like, I'm gonna build the biggest poker game in the world.

• 9:38David Friedberg?

  Can we talk, like, can you just talk a little bit about how you did that with respect to salesmanship and building confidence to grow that game? Like, you moved to a new city, you don't know anyone. How do you convince them? And maybe talk a little bit about what you learnt early on about sales and earning people's trust and how you got that to happen.

• 9:58Speaker 03

  Yeah. So, what I focused on much, much earlier than, you know, eventually I realized that if you're, if you're treating the business, if you're treating the poker game like a business, essentially what you want is you want nine people seated around a table with equal playing styles, equal skill, skill levels. And hopefully, you get these heart-pumping results, but at the end of the year, the money changes hands and the house wins. Okay? But before I realized that, what I had was, I was raised by parents who were, were very, they, they believed in teaching lessons all the time. And my dad's was excellence and discipline and overcoming fear.

• 10:43Speaker 03

  And my mom's was integrity, integrity, integrity. And what can you do for the world? And don't make people feel like they're transactions. And so, you know, that's, that's the education that I had. And so, I was a really hard worker and I really held myself to a high standard. So, for instance, when I started running these games, there was a lot of pros that would offer me free rolls, straight cash, if they could play, but I knew that that would compromise the integrity of the game. So, what I did is, I didn't take shortcuts, I just was trustworthy. And I invested in people and I, you know, I developed relationships and I was very intentional about...

• 11:24Speaker 03

  Before I walk in this, you know, not asking them for favors because everyone in the world was asking them for favors. And just, you know, instead of what can you do for me, what can I do for you? And over time, you know, I think people sense that you're a trustworthy person and that you are really deeply invested in their outcome. And I think that that was focusing on that relational capital and focusing on cultivating that trust and being a part of someone's life, doing events, you know, expanding the time that you spend together outside of just poker and, you know, doing events with the whole, with the whole crew. And so that's what I focused on and that was so incredibly valuable.

• 12:09Jason Calacanis?

  And a big part of this culture at the time was unlike, say, some other games where we have a group of friends, it's like a high trust environment, we settle up yearly, et cetera. The tradition in LA, at least in the ones I played in, was you settle up the next day, people would, and that would be your responsibility, I assume, or one of your runners, to go collect checks and settle with people. And then sometimes, you know, people maybe couldn't settle and it can get a little bit awkward. So maybe you could tell us about that part of the job that people don't see, which is, hey, you gotta go the next day. Somebody lost 50 grand, 250 grand. What's the big loss that you had to go collect? What was that like?

• 12:49Speaker 03

  A couple things. First of all, what shocked me was if you looked at the net worth at a lot of these people that were playing, it would indicate that a loss of a couple hundred thousand or even a million wasn't a big deal, right? But that wasn't the case. I saw crazy behavior.

• 13:14Speaker 03

  When I realized, kind of like, because I would ask myself the question, what's underneath this? You know, what is, what's causing this flipping of the tables, screaming at me that you're never going to pay, you know, whatever? And what I kind of got to is it's fear. Even though it doesn't make logical sense compared to someone's net worth, losing money or losing in general kind of triggers this fear response. You feel out of control. So, my job consistently was having enough top-down control to be able to be the one that could then make that person feel safe. Because I saw in other games, the game runner's on the hook for the money, this person's saying, "I'm never going to pay you," then they're both in fear, then they get into the sparring match, games end, things fall apart.

• 13:58Speaker 03

  So, it was really useful for me to just be able to emotionally regulate myself and understand what was going on.

• 14:07Jason Calacanis?

  And just talk them down from a ledge and get them to pay, because if somebody stiffs the game, the game, you could break the game, permanently.

• 14:13Speaker 03

  Well, I've been stiffed, and I wrote those checks.

• 14:15Jason Calacanis?

  Really? What's the biggest you got stiffed for?

• 14:17Speaker 03

  Two fifty.

• 14:18Jason Calacanis?

  Two fifty? And the person could afford to pay it?

• 14:20Speaker 03

  For sure.

• 14:21Jason Calacanis?

  And they stiffed you?

• 14:22Speaker 03

  For sure.

• 14:23Jason Calacanis?

  And then you've got to come out of pocket for that?

• 14:25Speaker 03

  Yep.

• 14:26Jason Calacanis?

  And make good?

• 14:27Speaker 03

  Yep.

• 14:28Jason Calacanis?

  Yeah, that's, that's hard.

• 14:29Speaker 03

  Yeah. But it teaches you to do a really good job on the, on the vetting.

• 14:32Jason Calacanis?

  Yes.

• 14:33Speaker 03

  I mean, I had bank employees on my payroll, basically, because in LA, people drive a Lamborghini, they rent a house in the valley, right?

• 14:41David Friedberg?

  Yeah. So, Molly, can you just talk about, you talked earlier with us, when we were playing poker, or during lunch, about, someone said, I think, "What sort of stuff are you into?"

• 14:52Speaker 03

  Yeah.

• 14:53David Friedberg?

  And you said, "I'm really into like adrenaline stuff, like adrenaline sports," right? And you're like competitive skier and so on. But this feels like that sort of high stakes environment that you put yourself in. Where did that come from? And do you think you selected yourself into this environment because it feels like heli-skiing?

• 15:12Speaker 03

  I think, first of all, I come from a really competitive family. One brother went to the Olympics twice, was a world champion in mogul skiing, world champ at sixteen. Then he went on to, after the Turin Olympics, get drafted, fifth round of the Philadelphia Eagles. He was an Abercrombie model.

• 15:36Speaker 03

  Then he started and sold a tech company at like literally the highest valuation like down to the second, I think. And now he's CEO of the X Games. And then my other brother is Harvard educated cardiothoracic surgeon at MassGen.

• 15:50Jason Calacanis?

  Which one do your parents love most?

• 15:52Speaker 03

  Well, they loved them more, but then Costner played my dad in a movie, so I became instantly the favorite kid.

• 15:58Jason Calacanis?

  So they eventually loved you?

• 16:00Speaker 03

  Eventually, but it took, I mean, it took a lot.

• 16:03Jason Calacanis?

  It did, yeah.

• 16:04Speaker 03

  So that was part of it. We grew up skiing and my dad was really insistent on fear is not going to sideline you. And so from an early age, like some kids get grounded for talking back or, you know, whatever, we got in trouble for letting fear get in the way. Or, and so something started to happen, I think, in those early years where it was like this very like exciting experience to look at something, be afraid of it, and then do it.

• 16:34Jason Calacanis?

  Like run a big game where people go south for 250K and then you decide, hey...

• 16:39David Friedberg?

  But that was the behavior you were trained on early on.

• 16:42Speaker 03

  I think it was a byproduct of socialization.

• 16:44David Friedberg?

  Look fear in the face and jump into it.

• 16:45Speaker 03

  Yeah. And that's a pretty great feeling, right?

• 16:49David Friedberg?

  Totally.

• 16:50Jason Calacanis?

  And a bit of pride, you wanted to restart the game. And so you had that pride.

• 16:54Speaker 03

  Big time pride.

• 16:55Jason Calacanis?

  So take us to the game, moving to New York, and the mob getting involved, you getting beat up, the getting pinched, and this whole thing going sideways.

• 17:03Speaker 03

  Okay. So moved to New York, to your question, really started interviewing poker players. What's the problem in the current system? Because there is really well-established games and whatever. And what I found was that there is a problem with trust. A lot of times gamers would play in their own games. If they did, had a bad night, the rake would be higher, da-da-da-da-da, I wasn't taking a rake. And then I realized, okay, well, if I can become the bank for these games and I can settle them and then provide this experience in which you could sit down next to your hero, or, you know, you could sit next to somebody who's going to change your life and business, and then there's no pros and it's all action. This is how I'm going to do it.

• 17:48Speaker 03

  So I became the bank for these games. The game in New York was a $250,000 buy-in. It was 2008 and I remember the first game. The president like was in the background on the, on the television like giving the State of the Union on the economy and there was like 10 million dollars on the table.

• 18:07Speaker 03

  These were insane games, they were playing insane variations.

• 18:14David Friedberg?

  And you loved the thrill, you feel the thrill, yeah.

• 18:17Speaker 03

  I did, yeah.

• 18:20Speaker 03

  I mean, this was the game that like ultimately someone lost 100 million. So, um, so yeah, so again, um, that definitely made noise.

• 18:28David Friedberg?

  Even by Coon standards.

• 18:32Speaker 03

  And yeah, so, and then I just decided, you know, I, cause I told my parents, listen, cause they're like, please go back to school, you know, please finish it, like go to law school.

• 18:42David Friedberg?

  They knew what you were doing.

• 18:43Speaker 03

  Yeah, and I was like, okay, but I just have to do this thing real fast. So I, I decided I was gonna go as big as I possibly can and then I started smaller games and it, and it got out of control and some of these guys from Brighton Beach started playing and I had them vetted, but their, and their stories checked out. I knew something was off, it was really off. They were running the biggest insurance fraud scheme in New York City history. They had alleged ties to the Russian mob. My only involvement with them was they played on my poker game. The next thing that happened was, um,

• 19:13Speaker 03

  the Italian mob or impersonators of the Italian mob, uh, came to me and said, you know, we, we want a piece of your game and I turned them down. And then they didn't just go away, um, and they sent someone to my apartment and, uh,

• 19:32Speaker 03

  this guy broke, broke in my apartment and he put a gun in my mouth.

• 19:35David Friedberg?

  Jesus.

• 19:36Speaker 03

  And he told me that, um, I work for them and that if I told anyone, law enforcement or anybody, that they had found out where my family lives in Colorado. And then he beat the hell out of me. And forced me to like, you know, you. Took everything out of my safe and there was money and there was a gold bar in there for some reason, but also things that my grandmother, who I was named after, left for me and you know, it was just terrifying and I was completely terrified, ashamed for what I was now implicating my family in and I couldn't call anyone and

• 20:14Jason Calacanis?

  Wow.

• 20:15Speaker 03

  I kept waiting for their call.

• 20:16Chamath Palihapitiya?

  Did you think at that moment to just stop and just say, you know what, okay, done?

• 20:20Speaker 03

  Yeah, but I didn't know if it was an option anymore.

• 20:23Chamath Palihapitiya?

  Right.

• 20:24Speaker 03

  Because they were looking at me as a big earner now and they, they'd said, this is a warning, it's not, it's not up to you anymore.

• 20:31Chamath Palihapitiya?

  Wow.

• 20:32Speaker 03

  So I didn't know what to do, like literally for the person.

• 20:35Jason Calacanis?

  Did you confide in anyone?

• 20:36Speaker 03

  I didn't, I didn't tell a single soul.

• 20:37Jason Calacanis?

  You didn't tell, you kept that all in?

• 20:39Speaker 03

  Yeah. And I'm in my apartment, I can't go outside because it's very clear I've been assaulted. And I'm confused as to why I'm not hearing them because about three or four days go by and I don't hear anything from them. And then I get the New York Times and on the cover it says, 125 arrested and the biggest mob-related takedown in New York City history. And I never heard from them again.

• 21:01Jason Calacanis?

  Oh my gosh, wow.

• 21:05Chamath Palihapitiya?

  Dodging a bullet, my gosh.

• 21:07Speaker 03

  But yeah, but then

• 21:08Chamath Palihapitiya?

  Oh my gosh.

• 21:09Speaker 03

  Then the bullet of me came into play and you know, so then I, I just started getting out of control and like I said, like, you know, integrity was an important thing to me, but over time I was making these little decisions, there were just a little left or right of, of where, where I stood and, and you know, greed, money, it became everything. And, and so I started doing things that my attorneys told me not to do.

• 21:33Jason Calacanis?

  Raking the game?

• 21:35Speaker 03

  Yeah, taking a rake.

• 21:36Jason Calacanis?

  Taking a rake. Now, for people who don't know, if you have a home game and you collect tips, it's kind of a gray zone, but generally speaking, people don't have a problem with it legally, but in the casino business, the legal gaming business, they feel that's their business to take a rake and they went through the proper channels to get a license to do that rake and you can't do that at a home game.

• 21:57Speaker 03

  Right.

• 21:58Jason Calacanis?

  And so now you're breaking the law.

• 21:59Speaker 03

  Right.

• 22:00Jason Calacanis?

  To make extra money.

• 22:01Chamath Palihapitiya?

  Sorry, just to be clear, a rake just means when you put money in the pot, they take a little bit of it out, they put it on the side, they keep it for themselves.

• 22:08Jason Calacanis?

  Or you pay an hourly rake, right? Yeah, that's a rake too.

• 22:11Chamath Palihapitiya?

  That's a rake too.

• 22:12Jason Calacanis?

  Yeah.

• 22:13Chamath Palihapitiya?

  But you were, you were, you were taking money out of the pots, keeping them for yourself.

• 22:16Speaker 03

  So basically what I was doing was I had become Much more lenient about who I was letting in the game. And so my exposure was getting bigger. And so in some of those games where I was betting on the players and they were bad bets, I started to take a rake. This was the last six months. The feds had put a confidential informant in the game because they were listening to the Russians phone. Who tracked that and in and then a couple of months later, I got a text message from one of the dealers. They said, "Don't come here, the FBI is here looking for you." And finally, I knew it was game over. And I would just wanted to go home, even though I pushed my family really far away.

• 23:01Speaker 03

  Like, I just wanted to go home. And so I tried to book a plane ticket from JFK to Denver and my credit card got declined. And then my next card got declined and I looked, logged into my bank account and it read negative nine million, nine hundred ninety-nine thousand. The Division of Asset Warfare had taken everything because your property, unlike your personhood, doesn't have the presumption of innocence, except for maybe in Florida.

• 23:28Jason Calacanis?

  Wow.

• 23:29Speaker 03

  I'm not up on the asset.

• 23:30Jason Calacanis?

  So now you're pinched. You get shaken down by the mob, then you get pinched by the feds.

• 23:34Speaker 03

  So the feds are, so my lawyers call and they say, you know, "She can sue us because this is on the civil side, but anything she says will also be counted as a confession." They said, "Do you want her? Are you pursuing any criminal charges?" They said, "No." I couldn't try to get my money back. I moved in with my mom, felt really sorry for myself, took me about two years to put my life back together, finally got this little job in LA, moved back into this little studio apartment. And I thought, "Okay, it's a fresh start," you know? Five days later, in the middle of the night, seventeen FBI agents, machine guns, high beam flashlights, put me in handcuffs and shackles and put this piece of paper in front of me that said, "The United States of America versus Molly Bloom."

• 24:19Jason Calacanis?

  Wow. What a year.

• 24:23Speaker 03

  I was really running hot.

• 24:24Jason Calacanis?

  Yeah.

• 24:25Speaker 03

  Um.

• 24:26Jason Calacanis?

  Couple of bad beats.

• 24:27Speaker 03

  So I had a day and a half to get to New York City to find an attorney and

• 24:32Jason Calacanis?

  And you're broke.

• 24:33Speaker 03

  And I don't have a penny. Yeah.

• 24:35Jason Calacanis?

  Wow.

• 24:36Speaker 03

  So.

• 24:37Jason Calacanis?

  How does it all resolve? How does the story resolve?

• 24:39Speaker 03

  So I found someone honorable and great to represent me. I didn't have money to fight it. So I pled out. The prosecutors wanted a meeting with me. Uh, this was the Southern District. And um, they really wanted me to become a, a CI. They weren't interested in the Russians or the Italians. They were interested in the billionaires and the politicians and the celebrities.

• 25:02Jason Calacanis?

  Who were for poker specifically.

• 25:04Speaker 03

  Yeah. Let me be really clear. There was no Epstein in my game.

• 25:07Jason Calacanis?

  Right.

• 25:07Speaker 03

  Right. Um, so they said if, you know, if you're

• 25:11Chamath Palihapitiya?

  They wanted you to be a rat against rich people, politicians and famous people.

• 25:15Speaker 03

  Yes.

• 25:16Chamath Palihapitiya?

  And what did you, what did they think you were gonna overhear? Like murder plots or like, like what? Like what were you gonna be able to tell them? Business deals?

• 25:25Speaker 03

  I could have given them leads.

• 25:27Jason Calacanis?

  Cause you overhear things.

• 25:29Chamath Palihapitiya?

  All kinds of stuff.

• 25:29Speaker 03

  Yeah.

• 25:30Chamath Palihapitiya?

  Crime.

• 25:30Speaker 03

  For sure.

• 25:31Chamath Palihapitiya?

  Wow.

• 25:33Speaker 03

  Um, now.

• 25:34Jason Calacanis?

  Is this Preet Bharara who was running the Southern District? Cause he, he's also famous for getting rid of online poker. He had a, he's a pretty by the books guy.

• 25:44Speaker 03

  For sure.

• 25:44Jason Calacanis?

  Yeah.

• 25:45Speaker 03

  Yeah.

• 25:45Jason Calacanis?

  And the Southern District of all districts is known for being the most hardcore.

• 25:50Speaker 03

  And politically ambitious and

• 25:53Jason Calacanis?

  Sure. Right.

• 25:54Speaker 03

  Um, and they said

• 25:56Chamath Palihapitiya?

  So did you, did you go to jail?

• 25:58Speaker 03

  I didn't. So they said, if you're willing to give, you know, if you're willing to work with us, we'll give you all your money back. We'll give you a deferred prosecution, which will keep you out of prison. And I had like 48 hours to make this call. And you know, where I got to it was like, this was my fault. Um, I, uh, I had near perfect information on the laws. I had all these opportunities. I had loyal clientele. I'd found this loophole and I was the one that decided to make this choice. And so to turn around and drag these people who had families through this bullshit. Um, based on my own bad decisions, like just didn't feel like something that I wanted to live with.

• 26:41Speaker 03

  So I turned down that offer and I waited to get sentenced and we all thought I was going to prison.

• 26:48Speaker 03

  And I got a judge who was very disappointed in my life choices. But, but basically said, you know, you had a life before this. And I had character letters from professors and ski coaches. And I had, um, a lot of people show up for me that had made better decisions than I had in life. And so he fined me a lot and, but I didn't go to jail. But, you know, then I was 35 years old, millions of dollars in debt, a convicted felon. The tabloids are telling this really reductive tale, like where, how do you come back from that? You know? And so I decided, well, there's a story here.

• 27:26Speaker 03

  And if I can monetize that, maybe that can address the reputational harm, the financial. I mean, I'm millions of dollars in debt. And, um, and so I wrote a book and, uh, waited for my life to change. And I think 10 people read it and probably like eight of them were related to me.

• 27:48Speaker 03

  But it was still my, it was still my only idea and I still kind of believed in it in my, in my gut. So I just made a short list of the most successful filmmakers in Hollywood. And I was like, why not, you know, why not just go for it? Um, but they needed to be brave because there was also a ton of people, as you can imagine. Yes. Even though I'd fallen on the sword, but legally, even though I hadn't implicated people in the book, they don't want exposure and I get that. Um, so Aaron Sorkin wrote A Few Good Men, Social Network, Moneyball. And he was my favorite writer and also the highest paid screenwriter at the time, which if you're gambling, which we always are, right? Good bet. Anyway, getting to him wasn't easy.

• 28:29Speaker 03

  I finally got to him and I just remember before I walked in, I was like, what am I doing?

• 28:36Speaker 03

  Millions of dollars in debt, my book sold 10 copies, like I live with my mom.

• 28:41Speaker 03

  And this is the highest paid screenwriter in the world, you know?

• 28:44Jason Calacanis?

  So you got a meeting with him?

• 28:45Speaker 03

  I did.

• 28:46Jason Calacanis?

  And you had sent him the book, obviously.

• 28:48Speaker 03

  So, somebody that I bothered relentlessly.

• 28:52Jason Calacanis?

  Right, so just to put the sales hat on again, like, the relentless pursuit of the sale.

• 28:58Speaker 03

  Yeah.

• 28:58Jason Calacanis?

  You were like all over this guy even though you weren't making... and you just kept going.

• 29:03Speaker 03

  Yeah, and I had met with other screenwriters and they were kind of a big deal and I was like, "No, no, no", and my brother was like, "You can't keep passing like you live with our mom."

• 29:11Jason Calacanis?

  What did he say when you get in the room?

• 29:13Speaker 03

  So, I told him my story.

• 29:17Speaker 03

  And I think like my legs were shaking but like I had this game face on, you know? And when I was done, he said, "Well, I'll tell you one thing, kid. I've never met someone so down on their luck and so full of themselves."

• 29:29Jason Calacanis?

  Wow, it's a good character study, yeah.

• 29:30Speaker 03

  Yeah, and then, you know.

• 29:34Jason Calacanis?

  They made an offer?

• 29:35Speaker 03

  Yep.

• 29:36Jason Calacanis?

  And then the... The rest is history. And then you use that money to pay down this fine you got?

• 29:41Speaker 03

  I did.

• 29:42Jason Calacanis?

  And...

• 29:43Speaker 03

  I just finally finished paying off the government last summer.

• 29:46Jason Calacanis?

  Wow, congratulations.

• 29:48Speaker 03

  I love my legal advice.

• 29:50Jason Calacanis?

  And I guess, you know, just to ask you the hard question, which you kind of answered. I was always wondering, like, how does one make the decision to write this tell-all book? And the fallout from that book, I remember in L.A., people talking about the book coming out, the books coming out, the books coming... everybody was really scared about it. You didn't put people's names in it, you specifically chose to, you know, make it...

• 30:13Speaker 03

  I put their name in it if they had talked about playing in the games.

• 30:17Jason Calacanis?

  Right.

• 30:17Speaker 03

  If they themselves, you know...

• 30:19Jason Calacanis?

  So you took some steps there, but you did make a decision, all these people who put you in business, etc., to basically turn on them and to basically tell their story. But there was no non-disclosure, you hadn't made any agreements to not talk about it.

• 30:34Speaker 03

  Well, I didn't turn on them, I actually supported them at every turn.

• 30:39Jason Calacanis?

  Well, I'm just saying like-

• 30:40Speaker 03

  I could have gotten a lot of money back and a deferred prosecution.

• 30:43Jason Calacanis?

  Okay, yes, in that case, yeah.

• 30:45Speaker 03

  And then the publishers were willing to pay me six, seven figures for a celebrity hit piece. I was broke, living with my mom. Again, I turned that down.

• 30:52Jason Calacanis?

  Got it.

• 30:53Speaker 03

  And I chose to work with a screenwriter that was absolutely clear and willing to contract it, that we aren't ruining any lives.

• 31:00Jason Calacanis?

  Great.

• 31:01David Friedberg?

  Do you still-

• 31:02Jason Calacanis?

  And the fallout from that, just so you know, is everybody in the, who had games, all the dealers, everybody involved, had to sign non-disclosures for the next-

• 31:10Speaker 03

  Probably smart.

• 31:11Jason Calacanis?

  Probably smart, yeah.

• 31:12David Friedberg?

  Do you still need to face fear in its face to feel like you're doing what you want to do?

• 31:19Jason Calacanis?

  Yeah.

• 31:21Speaker 03

  Um, I don't have this, I think, addiction to that anymore. Um, but I don't, I don't ever, I will always choose courage over comfort. I pay a big interior price internally if I don't. But it's not like this thing where I need that, you know, that, that adrenaline hit to make me feel alive. I like it. I pick my spots now. I have a three and a half year old daughter, so I knew before I brought a kid into the world, I wanted, I needed to do a lot of work on myself.

• 31:59Jason Calacanis?

  Right.

• 32:00Speaker 03

  Um, so that I could be the kind of-

• 32:02Jason Calacanis?

  You learned a lot about yourself.

• 32:05Speaker 03

  Yeah, too much.

• 32:06Jason Calacanis?

  I wonder what you could tell us about the nature of the men who are obsessed with playing this game and playing it at these stakes and the camaraderie, the competition and the chaos. What have you learned about the nature of these men?

• 32:23Speaker 03

  Well, again, I think, I don't like to, there's a couple different archetypes, okay?

• 32:30Jason Calacanis?

  Tell us.

• 32:31Speaker 03

  So there- There are the ones that are there on a self-destructive bullet train. So it's not just high stakes poker, right?

• 32:44Chamath Palihapitiya?

  Yeah.

• 32:44Speaker 03

  It's putting their marriage in bad places in very egregious and ways. There's drugs, there's, you know, it's, it's, it's the hedonic treadmill gone crazy.

• 32:58Chamath Palihapitiya?

  Got it.

• 32:59Speaker 03

  No more control over themselves, living for that next fix.

• 33:04Speaker 03

  Then there are just the highly competitive people who are very comfortable with volatility. In fact, prefer volatility and chaos, but still have some semblance of control over themselves.

• 33:19Speaker 03

  And, you know, and then I think there are people that play because they love the game. Because they like the aspects of it that make it an incredible game. They like the psychology, they like the making, you know, seeing the results of making high level decisions with very limited information. They like the mental

• 33:41Chamath Palihapitiya?

  Yes.

• 33:42Speaker 03

  And, and, and social thrill of it.

• 33:44Chamath Palihapitiya?

  The camaraderie and the competitiveness. Who's the best celebrity poker player? All the years that you saw in these games, who is the best?

• 33:53Speaker 03

  Toby.

• 33:54Chamath Palihapitiya?

  Toby.

• 33:54Speaker 03

  Yeah.

• 33:54Chamath Palihapitiya?

  And who is the second best? He wants you to say Chamath, but we were going to carve him out because he's not a celebrity. Look, I've played with Toby for 20 years, I would have said Toby too. I think he's exceptional. He's a grinder, he's tough.

• 34:04Speaker 03

  Yeah, he's tough. He, I mean, he, um, he was the only one in the game that was tight.

• 34:10Chamath Palihapitiya?

  Yeah.

• 34:11Speaker 03

  Um, I guess second would be Ben.

• 34:14Chamath Palihapitiya?

  Yeah, Affleck's a good player.

• 34:16Speaker 03

  Yeah. He, he's definitely smart, definitely knows what he's doing. It depends on where he is in his life.

• 34:20Chamath Palihapitiya?

  Yes. Yes. Politician wise, can you say or no?

• 34:24Speaker 03

  I haven't named any of the politicians because they haven't been named.

• 34:27Chamath Palihapitiya?

  Yeah, okay. Business people?

• 34:29Speaker 03

  Once again.

• 34:31Chamath Palihapitiya?

  They haven't named themselves, so we'll leave them unnamed.

• 34:33David Friedberg?

  And Molly, you were telling us before that you do some kind of Speaking work around sales, this is where I'm so interested in this like, what are the things you tell people when you do those events? What is the big takeaway from your experience?

• 34:47Speaker 03

  So a lot of people, so there's this small body of science called effective presence, effective with an A, and it really focuses on more of the subconscious, what's going on subconsciously. So if you work backwards from core human fears, which I think is always a really good thing to do. After dying, being alone in public speaking, you know, it's like, what are people most afraid of? They're afraid of not belonging, not being worthy, people stealing money from them, et cetera. And so when you start to think about what, what kind of emotional footprint am I leaving with these people? Like, you know, like, how can I disarm them and also cultivate trust at the same time?

• 35:32Speaker 03

  It takes a level of intentionality. And so I think what a lot of us do is we walk into a room and we're thinking, what are my, what's my resume? What are my soundbites? What's my pitch? Instead of thinking, how can I make this person feel like I'm with them? Like, this isn't a zero-sum game. And so there are just a couple of things that you could do. I mean, listening is a huge one. To listen with full presence, to not listen while you're constructing your response, but just ask open-ended questions, go down this road with someone. To, you know, have some warmth about you and some, you know, like, be affirming, but also be authentic.

• 36:15Speaker 03

  And, and to practice the hard empathy. Like, the easy empathy is people you relate to, people that have a similar experience to you. The hard empathy is sitting down and having conversations with people whose views you don't like, whose personality you don't particularly like, and trying to figure out or get to a place where you can understand them.

• 36:40David Friedberg?

  Yeah.

• 36:41Speaker 03

  And so...

• 36:42David Friedberg?

  Making that effort.

• 36:43Speaker 03

  Yeah, making that effort. And, and, you know, it's interesting. Humans hate uncertainty. Without an edited brain, and I mean edited by doing that work and meditation, whatever your mind training tool is, the brain thinks that uncertainty is a metabolically unsustainable state. So it equates uncertainty with fear. So how can you start to give people that sense of certainty? And also, how can you become aware of it in yourself? Because if you know that you hate uncertainty and then what you do is forage, forage, forage for some subjective truth and then cling to it.

• 37:24David Friedberg?

  Right.

• 37:25Speaker 03

  That's a big handicap, you know? And so to start to do work on relaxing with uncertainty and being more curious than needing to, you know, try to have this illusion of control. You know, there's a lot of things that aren't so obvious or instinctual.

• 37:42David Friedberg?

  Totally.

• 37:43Speaker 03

  In the art of impact and connection.

• 37:47David Friedberg?

  It can also force you to let go of priors.

• 37:49Speaker 03

  Right.

• 37:50David Friedberg?

  Which allows you to adapt and evolve.

• 37:53Speaker 03

  I mean, being able to adapt.

• 37:55David Friedberg?

  Yeah.

• 37:56Speaker 03

  And being able to court change and even, you know, reframe it as like, this is exciting or this is interesting.

• 38:01Jason Calacanis?

  What an incredible life you've had, ladies and gentlemen. Let's thank Molly for joining us.

• 38:06David Friedberg?

  Thank you, Molly.

• 38:07Jason Calacanis?

  And let's thank also Oracle, thank you for hosting. And my lord, we're gonna have a great weekend.