Molly’s Game Uncensored: Mob Threats, FBI Raid & 100M Pots… And Still Won

Summary

Molly Bloom, the entrepreneur behind the world’s most exclusive high-stakes poker games and subject of the Aaron Sorkin film “Molly’s Game,” joins the All-In Podcast besties live in Las Vegas. She shares the complete story of how she built and lost a multi-million dollar poker empire, from her origins as a cocktail waitress earning $4,000 tips to running $250,000 buy-in games in New York where one player lost $100 million.

The conversation takes dark turns as Molly recounts being assaulted by the Italian mob who put a gun in her mouth demanding a cut of her business, only to be saved when 125 mobsters were arrested days later. She details her subsequent FBI raid, asset seizure, and prosecution by the Southern District of New York, where she famously refused to become a confidential informant against the billionaires, celebrities, and politicians in her games - a decision that cost her all her money but kept her out of prison.

Molly also shares insights on salesmanship, trust-building, and the psychology of high-stakes players, explaining the different archetypes she observed: the self-destructive ones on a “bullet train” of hedonic excess, the highly competitive who thrive on volatility, and those who genuinely love the mental and social aspects of the game. She reveals Toby Maguire was the best celebrity poker player, followed by Ben Affleck, and discusses how she ultimately pitched Aaron Sorkin while millions in debt and living with her mother - leading to the movie deal that helped her pay off the government just last summer.

Highlights

”I’ll tell you one thing, kid. I’ve never met someone so down in their luck and so full of themselves.”

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“I was like, ‘What am I doing? 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.’ And when I was done, he said, ‘Well, I’ll tell you one thing, kid. I’ve never met someone so down in their luck and so full of themselves.’” — Molly Bloom, 29:13

”This guy broke into my apartment and he put a gun in my mouth”

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“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 they didn’t just go away… this guy broke into my apartment and he put a gun in my mouth and he told me that 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.” — Molly Bloom, 19:11

”125 arrested in the biggest mob related takedown in New York City history”

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“I’m confused as to why I’m not hearing from them because about 3 or 4 days go by and I don’t hear anything. And then I get the New York Times and on the cover it says 125 arrested in the biggest mob related takedown in New York City history and I never heard from them again.” — Molly Bloom, 20:34

”There was like $10 million on the table during the financial crisis”

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“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. These were insane games. They were playing insane variations… ultimately someone lost $100 million.” — Molly Bloom, 17:49

”The United States of America versus Molly Bloom”

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“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.’” — Molly Bloom, 23:51

”I will always choose courage over comfort”

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“Do you still need to face fear in its face to feel like you’re doing what you want to do? Yeah. I don’t have this I think addiction to that anymore. But I will always choose courage over comfort. I pay a big interior price internally if I don’t.” — Molly Bloom, 31:14

Key Points

• Origin Story (3:32) - Molly was a US ski team hopeful who had an accident and moved to LA seeking warmth, ending up serving drinks at a high-stakes poker game
• First Game Experience (3:59) - She served A-list celebrities, investment bank heads, politicians, and tech executives, earning $4,000 in tips her first night
• Building the Business (4:38) - Over 8 months she learned poker language and forged alliances, recognizing the game was about community, storytelling, belonging, and escapism
• Taking Over the Game (5:55) - At 24, she started her own game, raised buy-ins from $10K to $50K, and ran the LA game for 4-5 years
• Losing the LA Game (6:39) - A famous player (widely speculated to be Toby Maguire) became obsessed with the game and pushed her out, wanting to angle shoot and take her earnings
• Shuffle Master Drama (8:07) - Toby Maguire charged $200 per use to rent his $17,000 shuffle master machine
• Moving to New York (9:29) - In 2008, driven by pride, she moved to NYC and built a $250,000 buy-in game
• NYC Game Scale (17:54) - The NYC game had $10 million on the table during the financial crisis; one player ultimately lost $100 million
• Russian Mob Connection (18:52) - Players from Brighton Beach running NYC’s biggest insurance fraud scheme with Russian mob ties joined the game
• Italian Mob Assault (19:17) - A man broke into her apartment, put a gun in her mouth, beat her, robbed her safe, and threatened her family
• Miraculous Escape (20:53) - Days later, 125 mobsters were arrested in NYC’s biggest mob takedown, and she never heard from them again
• Taking a Rake (21:32) - In the final 6 months, she started illegally taking a rake from pots, which attracted FBI attention
• FBI Raid (24:11) - 17 FBI agents with machine guns arrested her in the middle of the night, presenting “The United States of America versus Molly Bloom”
• Refusing to Cooperate (24:52) - The Southern District offered money and deferred prosecution if she’d become a CI targeting billionaires, politicians, and celebrities - she refused
• Aaron Sorkin Meeting (28:16) - While millions in debt and living with her mom, she relentlessly pursued Sorkin, who told her “I’ve never met someone so down in their luck and so full of themselves”
• Best Celebrity Players (33:51) - Toby Maguire was the best (tight, disciplined), Ben Affleck second best
• Sales Philosophy (34:49) - Focus on “affective presence” - disarming people and cultivating trust by working backwards from core human fears

Mentions

Companies

• Oracle (0:42) - Sponsor of the VIP lunch event in Vegas at the Venetian
• Fortune Magazine (1:21) - Named Molly one of their most powerful women
• FBI (22:56) - Investigated and arrested Molly after placing a confidential informant in her game
• Southern District of New York (24:52) - The federal district that prosecuted her case
• Philadelphia Eagles (15:31) - Drafted Molly’s brother in the fifth round after his Olympic skiing career
• X Games (15:46) - Molly’s brother is now CEO

Products & Technologies

• Shuffle Master (8:07) - $17,000 card shuffling device that speeds up poker games; only three existed in LA at the time

People

• Molly Bloom (0:14) - Subject of the interview, ran legendary high-stakes poker games in LA and New York
• Toby Maguire (3:16) - Actor and poker player who allegedly took over Molly’s LA game; best celebrity poker player according to Molly
• Aaron Sorkin (0:36) - Screenwriter of A Few Good Men, Social Network, Moneyball who wrote and directed Molly’s Game
• Ben Affleck (34:15) - Second best celebrity poker player; “definitely smart, depends on where he is in his life”
• Kevin Costner (15:57) - Played Molly’s father in the movie, making her “instantly the favorite kid”
• Leonardo DiCaprio (2:57) - Mentioned as someone who played in the games (“Leo’s going to be there”)
• Phil Hellmuth (1:06) - Professional poker player mentioned as appearing at the bestie poker game
• Alan Keating (1:02) - Poker player participating in the bestie poker freeze out
• Preet Bharara (25:36) - Former US Attorney for Southern District, mentioned for going after online poker

Surprising Quotes

“I’ll tell you one thing, kid. I’ve never met someone so down in their luck and so full of themselves.” — Aaron Sorkin to Molly Bloom, 29:25

“This guy broke into my apartment and he put a gun in my mouth… and he told me that 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.” — Molly Bloom on the mob assault, 19:34

“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.” — Molly Bloom on NYC games during the financial crisis, 17:57

“I had bank employees on my payroll basically because in LA people drive a Lamborghini, they rent a house in the valley.” — Molly Bloom on vetting players, 14:35

“I will always choose courage over comfort. I pay a big interior price internally if I don’t.” — Molly Bloom on facing fear, 31:32

Transcript

0:00 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 in 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.

0:26 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 at the Venetian. What a great hotel.

0:49 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, Friedberg, me, or some of the world’s greatest poker players, Alan Keating and Jason. 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.

1:15 Listen, we have a guest. We do have a guest. She’s an entrepreneur, bestselling author, one of Fortune magazine’s most powerful women. I didn’t know that. 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.

1:48 All right. Nice to see you, Molly. Molly, what was the origin of the game? We know some of our friends played in it. Well, hold on a second. Jason, you claimed on our show, let me just read the notes. The notes? Um, yeah, there are notes here. What did I say? Apparently, where’s the thing that Jason said? We were on the show and Jason said he played in the game all the time. No, no, no, no. I was invited to the game.

2:14 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 game. Okay, let’s be clear. Molly, did you invite me to the game? 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.

2:41 Got it. And I’m sure that you were probably on that list. Jeffrey Epstein’s list, right? He was young. Absolutely. Okay. But when it was my game, you know, I just remember the Four Seasons. Was that your game? 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.

3:03 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 Toby 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 like how this all got started for you and when you took over the game.

3:32 Okay. So I was in college, game 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 to serve drinks at my poker game.”

3:59 Okay. And so I show up to this poker game and it, 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.

4:24 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.”

4:38 And 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 about 3 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.

5:11 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. 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.

5:41 And so I really started to build on those topics and 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 8 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. And so I would say that started about 4 and a half, five year tenure of the LA game.

6:12 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. 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. And you really elevated the game.

6:32 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. So I lost the game in LA. How do you lose the game in LA?

6:48 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, wanted to and then sort of wanted to kind of do things that felt wrong. Okay. Like maybe target certain weak players, maybe get some of your tip money, like actively cheat the game. Yeah. Angle shoot. And also was complaining that I made too much money.

7:17 Got it. And basically gave me this offer. I’ll pay you a salary and you can work for me. You can be the figurehead. And I really wanted to keep the game. I was making millions of dollars legally. I was paying my taxes. It was incredibly exciting and educational. But I didn’t want to be under - I didn’t want to work for him.

7:42 Right. There’s a power imbalance because this person theoretically might have been 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. They wanted 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. JKL. Toby Maguire. Uh-huh.

8:06 And 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 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.

8:31 I’ll never forget going to his house. No, Toby. Not me. Not you. Not you. Um, yeah. I’ll never forget. So, he was right. Renting out a shuffle master. I mean, he had a tough couple years. You said it was a pretty big downdraft.

8:47 So, shuffle masters cost $17,000 at the time. Yeah. 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 going to 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 5 months in, I’m like, “We need to buy our own shuffle master.”

9:17 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 and you’re like - Somebody takes the game away, right? And so, you’re like, “I’m moving to New York and restarting the game there.”

9:29 Well, I was really pissed and it was 2008, so yeah, I was like, I’m going to build the biggest poker game in the world. Can we 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 and earning people’s trust and how you got that to happen?

10:03 Yeah. So what I focused on much much earlier than - you know eventually I realized that 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 and hopefully you get these heart-pumping results but at the end of the year the money changes hands and the house wins.

10:33 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.

10:56 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 developed relationships and I was very intentional about before I walk in, 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?

11:37 And over time, I think people sense that you’re a trustworthy person and that you are really deeply invested in their outcome and I think 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 doing events with the whole crew and so that’s what I focused on and that was so incredibly valuable.

12:11 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 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.

12:41 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?

12:54 A couple things. First of all, what shocked me was if you looked at the net worth of 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. And when I realized, kind of like - because I always would ask myself the question, what’s underneath this? You know, what is what’s causing this flipping of the table, screaming at me that you’re never going to pay, you know, whatever.

13:30 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.

14:04 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, you could break the game permanently.

14:15 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 and then you’ve got to come out of pocket for that and make good. Yeah. That’s hard. Yeah. But it teaches you to do a really good job on the vetting. Yes. 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.

14:44 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? Yeah. 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?

15:15 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 16. Then he went on to after the Turin Olympics get drafted fifth round by the Philadelphia Eagles. 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 Mass General.

15:53 So which one do your parents love most? Well, they loved them more, but then Costner played my dad in the movie, so I became instantly the favorite kid. So they eventually loved you. Eventually, but it took a lot. It did. Yeah.

16:06 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 whatever. We got in trouble for letting fear get in the way. And so something started to happen, I think, in those early years where it was like this very exciting experience to look at something, be afraid of it, and then do it.

16:35 Like run a big game where people go south for 250k and then you decide, hey - but that was the behavior you were trained on early on. I think it was a byproduct of social - fear in the face and jump into it. Yeah. And 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.

16:58 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.

17:08 Okay. So moved to New York to your question - really started interviewing poker players. What’s the problem in the current system? Because there are really well established games and whatever. And what I found was that there was a problem with trust. A lot of times game runners would play in their own games. If they had a bad night the rake would be higher. 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 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.

17:49 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. These were insane games. They were playing insane variations.

18:16 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 yeah, that definitely made noise.

18:32 And yeah so then I just decided - because I told my parents listen - they’re like please go back to school, you know, please finish your - I knew what you were doing. Yeah. And I was like okay but I just have to do this thing real fast. So, 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 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.

19:11 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. And they sent someone to my apartment and this guy broke into my apartment and he put a gun in my mouth - Jesus - and he told me that 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 - 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.

20:04 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. Wow. 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’d said, “This is a warning. It’s not up to you anymore.” Wow.

20:34 So, I didn’t know what to do. Like, literally for the first time - you couldn’t confide in anyone. I didn’t tell a single soul. You didn’t tell - You kept that all in. 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 from them because about 3 or 4 days go by and I don’t hear anything from them.

20:54 And then I get the New York Times and on the cover it says 125 arrested in the biggest mob related takedown in New York City history and I never heard from them again. Wow. Dodging a bullet. My god. Oh my god. But yeah, but then - Oh my gosh.

21:11 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 integrity was an important thing to me but over time I was making these little decisions that were just a little left or right of where I stood and you know greed, money became everything and so I started doing things that my attorneys told me not to do.

21:35 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, right? And so now you’re breaking the law, right? To make extra money.

22:03 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. In the casino, they do an hourly rake, right? Yeah, that’s a rake, too. That’s a rake, too. Yeah. Yeah. Different. You were taking money out of the pots, keeping them for yourself.

22:19 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.

22:49 Who tracked that and then a couple months later I got a text message from one of the dealers and 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’d pushed my family really far away. 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 logged into my - 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.

23:30 Not - I’m not up on the asset. Now you’re pinched. You get shaken down by the mob. Then you get pinched by the feds. So the feds - 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.

23:51 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, 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.”

24:23 Wow. Wow. What a year. I was really running hot. Yeah. Wow. 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.

24:38 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.

25:11 So they said if you know if you’re - they wanted you to be a rat against rich people, politicians, and famous people. Yes. And what did they think you were going to overhear like murder plots or like what were you going to be able to tell them? Business deals. I could have given them leads for all kinds of stuff. Yeah. Crime for sure. Wow.

25:36 Was this Preet Bharara who was running the Southern District because he’s also famous for getting rid of online poker. He had a - He’s a pretty by the books guy for sure. Yeah. And the Southern District of all districts is known for being the most hardcore and politically ambitious. Sure. Right. All right.

25:56 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 and 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.

26:18 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 based on my own bad decisions just didn’t feel like something that I wanted to live with.

26:44 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 but I didn’t go to prison.

27:14 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 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 then I think 10 people read it and probably like eight of them were related to me.

27:51 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, you know, why not just go for it. 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 legally, even though I hadn’t implicated people in the book, they don’t want exposure and I get that.

28:16 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? It’s a 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? 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.

28:45 So, you got a meeting with him. I did. And he had - you had sent him the book obviously. So, somebody that I bothered relentlessly. Right. So, you’re just to put the sales hat on again like the relentless 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 - 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 your mom.”

29:13 What did you say when you get in the room? 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 in their luck and so full of themselves.” Wow. It’s good character study. Yeah.

29:34 And then, you know, they made an offer. Yep. And then they paid and then you used that money to pay down this fine you got. I did. And I just finally finished paying off the government last summer. Wow. Wow. Congratulations.

29:54 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 LA people talking about the book coming out. The book’s coming out. The book’s coming. Everybody 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? So if they themselves, you know.

30:22 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.

30:36 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. Okay. 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 that we aren’t ruining any lives.

31:03 Great. And the fact 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.

31:14 Do you still need to face fear in its face to feel like you’re doing what you want to do? Yeah. I don’t have this I think addiction to that anymore. 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 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 needed to do a lot of work on myself right - so that I could be the kind of - you learned a lot about yourself.

32:08 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.

32:26 Well, again, I think I don’t like to - there’s a couple different archetypes. Okay, tell us. So, there are the ones that are there on a self-destructive bullet train. So, it’s not just high stakes poker, right? Yeah. It’s putting their marriage in bad places in very egregious ways. There’s drugs. There’s, you know, it’s the hedonic treadmill gone crazy. Got it. No more control over themselves, living for that next fix.

33:07 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. 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 making, you know, seeing the results of making high-level decisions with very limited information. They like the mental and social thrill of it, the camaraderie and the competition.

33:51 Who’s the best celebrity poker player in all the years that you saw in these games? Who is the best? Toby. Yeah. And who is the second best? He wants you to say Chamath, but we were going to carve him out because he’s not - Look, I played with Toby for 20 years. I would have said Toby, too. I think he’s exceptional. He’s a grinder. He’s tough. Yeah, he’s tough. He - I mean he was the only one in the game that was tight. Yeah.

34:14 I guess second would be Ben. Yeah. Affleck’s a good player. Yeah. He’s definitely smart. Definitely knows what he’s doing. It depends on where he is in his life. Yes.

34:24 Politician wise, can you say or no? I haven’t named any of the politicians because they haven’t been named. Yeah. Okay. Business people. Once again, they haven’t named themselves, so we’ll leave them unnamed.

34:34 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?

34:49 So a lot of people - So there’s this small body of science called affective presence - affective with an A - and it really focuses on more of 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, 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, etc.

35:20 And so when you start to think about what kind of emotional footprint am I leaving with these people, how can I disarm them and also cultivate trust at the same time - 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’s my resume, what are my sound bites, 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.

35:54 And so, there are just a couple 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 have some warmth about you, be affirming. But also be authentic. And to practice the hard empathy.

36:30 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, you know? Yeah. And so making that effort.

36:45 Yeah. Making that effort 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.

37:11 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 for some subjective truth and then cling to it, right? 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 try to have this illusion of control. There’s a lot of things that aren’t so obvious or instinctual.

37:46 Totally. In the art of impact and connection. It can also force you to let go of priors, right? Which allows you to adapt and evolve. And I mean, being able to adapt and being able to court change and even, you know, reframe it as like this is exciting or this is interesting.

38:03 What an incredible life you’ve had, ladies and gentlemen. Let’s thank Molly for joining us. Thank you, Molly. Thank you so much. And let’s thank also Oracle. Thank you for hosting. And my lord, we’re - I’m going all in.