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

0:00Hey, 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.

0:37Big thank you to our friends at Oracle for partnering with us on this amazing VIP lunch we did in Vegas 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 going to win? Chamath, Freebert, 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. Listen, we have a guest. We do have a guest. She's an entrepreneur, bestselling author, one of Fortune Magazine's most powerful women.

1:21I didn't know that. Oh, very. 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.

1:44Thank 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. Hold on a second. Jason, you claimed on our show, let me just read the notes. The notes? Yeah, there are notes here. What did I say now? 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 no no no no what did you say I was invited to the game no you did not say that Lisa please pull the tape no 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 game okay let's be clear Molly did you invite me to the game I don't remember inviting you to the game.

2:31But 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. Got it. And I'm sure that you were probably on that list. It was Jeffrey Epstein's list, right? Absolutely. Okay. But when it was my game, you know. I just remember the Four Seasons. Yeah. Was that your game? It was. Okay, so it was the Four Seasons. I remember you invited me and you said, Toby's going to be there. Leo's going to 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.

3:06But 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, 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. Okay. So I was in college, skiing for the US skate 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 two years old. And ended up working for this guy.

3:49He had a real estate development company, and he said, tomorrow night I need to serve drinks at my poker game. Okay. And so I show up to this poker game, and 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, 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.

4:34And over the next eight months, 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.

5:22And 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 and we're going to come, let alone make it their home game.

6:02And 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. um i raised it to a 50 thousand dollar buy-in and um that's the number i remember and i was like wow those are high stakes because at the time even in la yeah people were not playing in those stakes for sure 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 it did um so i lost the game in How do you lose the game in LA? 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.

6:55And then sort of to want to kind of do things that felt wrong. Okay. Okay. Like maybe target certain weak players, maybe get some of your tip money. like actively cheat the game yeah um angle shoot the game angle shoot and and also was complaining that i made too much money got it um and basically gave me this offer i'll pay you a salary and you can work from you can be the figurehead uh-huh 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.

7:40Right. There's a power imbalance because this person theoretically might have been famous. Super famous. And the players might follow them if they boxed you out. Yeah, he said, turns out they want to play at a movie star's house. Ah. They want to what? Play at a movie star's house. Got it. And is it well known who that person is? It's well speculated. She never says. Who they speculated, J.K.L.? toby mcguire and he i the uh concept also was uh 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 right from somebody in vegas theoretically but they weren't available and chmoth remembers because he got an early one and i used to bring mine to chmoth's game he'd say hey can you bring the the shuffle master he also angle shot you and wanted you to rent a shuffle master i'll never forget going to his house no he toby not me not you not you um yeah i'll never forget so he he was right tomorrow's renting out a shuffle master i mean he had a tough couple years you said there was a pretty big down draft so shuffle masters cost 17 000 at the time yeah um and he was right that we needed one it was uh 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.

8:58And then I brought it back and he said, I'm going to need$200 for this. And 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. Right. Yeah, they can be obtained. So you get the game taken away from you. The game moves to New York. Sorry, so Toby takes the game away. Somebody takes the game away. Right. And so you're like, I'm moving to New York and restarting the game there? Well, I was really pissed. And I, you know, and I, it was 2008. So, yeah, I was like, I'm going to build the biggest poker game in the world.

9:39Can 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 learned early on about sales sales and earning people's trust and how you got that to happen. Yeah. So what I focused on much earlier than, you know, eventually I realized that 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 levels.

10:19and 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 very, they believed in teaching lessons all the time. And my dad's was excellence and discipline and overcoming fear. 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 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.

11:07But 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, 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, expanding the time that you spend together outside of just poker and doing events with the whole crew.

12:03And so that's what I focused on. And that was so incredibly valuable. 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, etc. 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 got to 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 a couple things first of all what shocked me was if you looked at the net worth that 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?

13:06But that wasn't the case. I saw crazy behavior. And what I realized kind of like, because I would ask myself the question, what's underneath this? You know, 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.

13:47Because 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. so it was really useful for me to just be able to emotionally regulate myself and understand what was going on 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 well i've been stiffed and i wrote those checks really what's the biggest you got stiffed for 250 250 and the person could afford to pay it for sure and they stiffed you for sure and then you've got to come out of pocket for that and make good.

14:27That's hard. But it teaches you to do a really good job on the vetting. 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? 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? 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?

15:07And do you think you selected yourself into this environment because it feels like heliskiing? 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. at world champ at 16. Then he went on to, after the Turin Olympics, get drafted fifth round of the Philadelphia Eagles. He was an Abercrombie model. 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.

15:51So... Which one do your parents love most? Well, they loved them more, but then Costner played my dad in a movie, so I became instantly the favorite kid. So they eventually loved you. Eventually, but it took a lot. It did, yeah. 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 it like exciting experience to look at something be afraid of it and then do it like run a big game that was that was out for 250k and then you decide hey that was the behavior you were trained on early on I think it was a byproduct of social in the face and jump into it Yeah.

16:45And that's a pretty great feeling, right? Totally. And a bit of pride. You wanted to restart the game. And so you had that pride. Big time pride. So take us to the game, moving to New York, and the mob getting involved, you getting beat up, getting pinched, and this whole thing going sideways. Okay. So move to New York. To your question, really started interviewing poker players. what's the problem in the current system? Because there's 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 had a bad night, the rake would be higher.

17:26Da-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 could sit next to somebody who's going to change your life in business and then there's no pros and it's all action. This is how I'm going to do it. 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 was in the background on the television giving the State of the Union on the economy and there was like$10 million on the table.

18:07these were insane games they were playing insane variations and you love the thrill you feel the thrill yeah I did yeah I mean this was the game that like ultimately someone lost 100 million so um so yeah so again um that definitely made noise even by coon standards

18:33and yeah so and then i just decided you know i because i told my parents listen because they're like please go back to school you know please finish your like go to what you were doing yeah and i was like okay but i just have to do this thing real fast so i i decided i was going to go as big as i possibly can and then i started smaller games and it got out of control and some of these guys from brighton beach started playing and i had them vetted but there's and 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.

19:03They 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 the Italian mob, or impersonators of the Italian mob, came to me and said, you know, 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 this guy broke broke in my apartment and he put a gun in my mouth and he jesus 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 I 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.

20:02And, 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 I kept waiting for their call. Did you think at that moment to just stop and just say, you know what? Okay, done. Yeah, but I didn't know if it was an option anymore. Right. Because they were looking at me as a big earner now, and they said, this is a warning. It's not up to you anymore. Wow. So I didn't know what to do, like literally. Did you confide in anyone? I didn't tell a single soul. You kept that all in? Yeah. And I'm in my apartment.

20:41I 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. Oh my God. Wow. Dodging a bullet. Oh my gosh. But yeah. Oh my gosh. Then the bullet of me came into play. And, you know, so then 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.

21:19They were just a little left or right of where I stood and greed, money, it became everything. And so I started doing things that my attorneys told me not to do. Raking the game? Yeah, taking a rake. 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.

21:57And so now you're breaking the law to make extra money. 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. Or you pay an hourly rake, right? Yeah, that's a rake too. That's a rake too. Yeah, different ways to rake. You were taking money out of the pots keeping them for yourself? 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.

22:34This was the last six months. The feds had put a confidential informant in the game because they were listening to the Russian's phone, who tracked that. And then a couple 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 just wanted to go home, even though I pushed my family really far away. I just wanted to go home. 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 um the division of asset forfeiture had taken everything because your property unlike your personhood doesn't have the presumption of innocence except for maybe in Florida not wow I'm not up on the asset so now you're pinched you get shaken down by the mob then you get pinched by the feds 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.

23:42They 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. It 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, 17 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. Wow. What a year.

24:23I was really running hot. Yeah. Wow. A couple of bad beats. So I had a day and a half to get to New York City to find an attorney. and you're broke and I don't have a penny yeah wow so how does it all resolve how does the story resolve 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 this was the southern district and they really wanted me to become a CI they weren't interested in the Russians or the Italians they were interested in the billionaires and the politicians and the celebrities who were for poker specifically yeah let me be really clear there was no epstein in my game right right um so they said if you know they wanted you to be a rat against rich people politicians and famous people yes and what did you what did they think you were going to overhear like murder plots or like like what like what were you going to be able to tell them business deals i could have given them leads because you overhear for all kinds of stuff.

25:30Yeah. Crime. For sure. Wow. Wow. Now - Is this Preet Bharara, who was running the Southern District? Because he's also famous for getting rid of online poker. Yeah. He's a pretty by-the-books guy. For sure. Yeah. Yeah. And the Southern District, of all districts, is known for being the most hardcore. And politically ambitious. Sure. Right. And they said - So did you go to jail? 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.

26:10And, you know, where I got to it was like, this was my fault. I had near perfect information on the laws. I had all these opportunities. I had loyal clientele. I 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, based on my own bad decisions, like just didn't feel like something that I wanted to live with. So I turned down that offer and I waited to get sentenced and we all thought I was going to prison. And I got a judge who was very disappointed in my life choices, but basically said, you know, you had a life before this and I had character letters from professors and ski coaches and I had 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?

27:21And so I decided, well, there's a story here. 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 so I wrote a book and waited for my life to change. And I think 10 people read it and probably like eight of them were related to me. But it was still my only idea, and I still kind of believed in it in my gut. So I just made a short list of the most successful filmmakers in Hollywood, and I was like, why not? Why not just go for it? But they needed to be brave because there was also a ton of people, as you can imagine.

28:06Yes. 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 I finally got to him and I just remember before I walked in I was like what am I doing I've millions of dollars in debt my book sold 10 copies like i live with my mom and this is the highest paid screenwriter in the world you know so you got a meeting with him i did and he had you had sent him the book obviously so somebody that i bothered like relentlessly right so you're just to put the sales hat on again yeah like the relentless like pursuit of the sale yeah you were like all over this guy even though yeah you weren't making and you just kept going yeah and i and i you know i had met with other screenwriters and they were kind of a big deal and I was like no no no and my brother's like you can't keep passing like you live with what does he say when you get in the room um so I told him my story and I think like my legs were shaking but like I had this game face on you know yeah 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 wow it's a good character study yeah yeah um and then you know they made an offer yep and then the rest is made and then you use that money to pay down this uh fine you got i did and i just finally finished paying off the government last summer wow congratulations and i guess you know the 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 And the fallout from that book, I remember in LA, people talking about the book coming out, the books coming out, the books coming out.

30:07Everybody was really scared about it. You didn't put people's names in it. You specifically chose to, you know, make it. I put their name in it if they had talked about playing in the games. Right. If they themselves, you know. So you took some steps there, but you did make a decision, all these people who put you in business, et cetera, 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. Well, I didn't turn on them. I actually supported them at every turn. Well, I'm just saying like - I could have gotten a lot of money back and a deferred prosecution.

30:43Okay. Yes. In that case. Yeah. 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. Got it. And I chose to work with a screenwriter that was absolutely clear and willing to contract it that we aren't ruining any lives. Great. And the follow-up from that, just so you know, is everybody who had games, all the dealers, everybody involved had to sign non-disclosures for the next... Probably smart. Probably smart, yeah. Do you still need to face fear in its face to feel like you're doing what you want to do?