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

Speaker 1 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.

Speaker 1 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.

Speaker 1 And her story was turned into the feature of film and book, Molly's Game.

Speaker 1 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.

Speaker 1 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.

Speaker 1 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?

Speaker 1 Shamah Freebert, me, or some of the world's greatest poker players, Alan Keating and Jason Kuhn. Also, Phil Helmuth.
He wound up there as well somehow. So happy Thanksgiving.
We love you and

Speaker 1 be safe. And we'll see you all next week for a regular episode.

Speaker 2 Listen, we have a guest. We do have a guest.

Speaker 2 She's an entrepreneur, best-selling author, one of Fortune magazine's most powerful women.

Speaker 3 I didn't know that. Oh.

Speaker 2 Molly Bloom ran the world's most exclusive poker game. You probably know her from

Speaker 2 the movie Molly's Game, which we'll hear a little bit about today.

Speaker 2 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.

Speaker 2 So please join me in welcoming Molly.

Speaker 2 Thank you.

Speaker 4 Nice. Nice to see you, Molly.
Molly, what was the origin of the game? We know some of our friends played in it.

Speaker 2 Well, hold on a second. Jason, you claimed on our show, let me just read the notes.
The notes? Yeah, there are notes here.

Speaker 3 What did I say?

Speaker 2 So apparently, where's the thing that Jason said? We were on the show, and Jason said he played in the game all the time.

Speaker 4 No, no, no, no. What did you say? You said I was invited to the game.
No, you did not say that.

Speaker 2 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 fing game.

Speaker 3 Okay,

Speaker 3 let's be clear.

Speaker 4 Molly, did you invite me to the game?

Speaker 5 I don't remember inviting you to the game.

Speaker 5 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. Got it.

Speaker 5 And I'm sure that you were probably on that list when I was in the game.

Speaker 3 It was Jeffrey Epstein's list. Right.
He was young.

Speaker 3 Okay.

Speaker 4 But when it was my game, you know, I just remember the four seasons.

Speaker 3 Yeah.

Speaker 4 Was that your game?

Speaker 3 It was.

Speaker 4 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.

Speaker 4 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

Speaker 4 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.

Speaker 4 Famously, Toby Maguire, a friend of ours, we play poker with sometimes, was part of this.

Speaker 4 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.

Speaker 3 Okay.

Speaker 5 So I was in college, skamed 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.

Speaker 5 I'd been cold since I was two years old and ended up working for this guy.

Speaker 5 He had a real estate development company and he said, tomorrow night I need to serve drinks at my poker. my poker game.
Okay.

Speaker 5 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.

Speaker 5 And I get to be a fly on the wall in this incredibly compelling room. And also, you know, I'm in my, I'm 23 years old.
This is access to information, to capital, to power.

Speaker 5 And then at the end of the night, They were tipping me in chips and someone counted out $4,000 in cash.

Speaker 5 And I was like, okay, I I don't know what's up with this chip token economy but I think I might want in

Speaker 5 and over the next eight months

Speaker 5 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

Speaker 5 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.

Speaker 5 You could use it to infiltrate any subset of society.

Speaker 5 And I was learning about the world from some of the people who were

Speaker 5 actively involved in shaping culture. So it was a fascinating,

Speaker 5 interesting time, and it was also very lucrative.

Speaker 5 And so

Speaker 5 I decided to start my own games, and I had eight months of notes of... what I would do differently.

Speaker 5 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

Speaker 5 belonging to something and it's about escapism and fantasy. And so I really started to build on those topics and those,

Speaker 5 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.

Speaker 5 And so when I started the game eight months later,

Speaker 5 you know, I was 24 years old. I didn't think these people who are rich and famous

Speaker 5 were going going to come, let alone make it their home game. And so I would say that started the about four and a half, five-year tenure of the LA game.

Speaker 5 And when we started out, when I was serving drinks, it was a $10,000 buy-in.

Speaker 5 I raised it to a $50,000 buy-in.

Speaker 4 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. Oh, for sure.

Speaker 4 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.

Speaker 5 It did.

Speaker 5 So I lost the game in L.A.

Speaker 4 How do you lose the game in L.A.?

Speaker 3 Well,

Speaker 5 one of the players who was making 10x, but he was making in the poker game, became very obsessed with this game. and wanted to talk about it all the time,

Speaker 5 and then sort of to want to kind of do things that felt wrong.

Speaker 3 Okay.

Speaker 5 Okay.

Speaker 4 Like maybe target certain weak players, maybe

Speaker 4 get some of your tip money.

Speaker 7 Like actively cheat the game.

Speaker 4 Angle shoot the game. Angle shoot.

Speaker 5 And also was complaining that I made too much money.

Speaker 7 Got it.

Speaker 5 And basically gave me this offer. I'll pay you a salary and you can work from you can be the figurehead.
Uh-huh.

Speaker 5 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.

Speaker 6 But

Speaker 5 I didn't want to be under, I didn't want to work for him.

Speaker 3 Right.

Speaker 4 There's a power imbalance because this person theoretically might have been famous.

Speaker 3 Super famous.

Speaker 4 And the players might follow them if they boxed you out.

Speaker 5 Yeah, he said,

Speaker 5 turns out they want to play at a movie star's house.

Speaker 3 Ah. They want to do what?

Speaker 5 Play at a movie star's house.

Speaker 4 Got it.

Speaker 7 And is it well known who that person is?

Speaker 4 It's well known. She speculated.
She never says.

Speaker 2 Who they speculate, J. Cal?

Speaker 4 Toby Maguire.

Speaker 4 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.

Speaker 4 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.

Speaker 4 And Schmoth remembers because he got an early one. And I used to bring mine to Schmat's game.
He'd say, hey, can you bring the Shuffle Master?

Speaker 4 He also angle shot you and wanted you to rent a Shuffle Master.

Speaker 5 I'll never forget going to his house.

Speaker 7 No, he, Toby, not me.

Speaker 3 Not you. Not you.
Not you.

Speaker 5 Yeah, I'll never forget. So he was right.

Speaker 3 Jamal's renting out a shuffle master.

Speaker 3 I mean, he had a tough couple of years. You said, there was a pretty big downdraft.

Speaker 5 So shufflemasters cost $17,000 at the time. Yeah.

Speaker 5 And he was right that we needed one.

Speaker 5 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.

Speaker 5 And then I brought it back and he said um i'm gonna need two hundred dollars for this

Speaker 5 i'm like you're 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

Speaker 7 yeah they can be obtained so you get the game taken away from you the game moves to new york sorry so toby toby takes the game away and you're like somebody takes the game away somebody likes the game away right and so you're like i'm moving to new york and restarting the game there

Speaker 3 well

Speaker 3 i

Speaker 5 was really pissed. And I,

Speaker 5 you know, and I, it was 2008.

Speaker 5 So, yeah, I was like, I'm going to build the biggest poker game in the world.

Speaker 2 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 move to a new city, you don't know anyone.

Speaker 2 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.

Speaker 5 Yeah.

Speaker 5 So,

Speaker 5 what I focused on much much earlier than

Speaker 5 you know, eventually I realized that if you're if you're treating the business, if you're treating the pilgrim like a business, essentially what you want is you want nine people seated around a table with equal playing styles, equal

Speaker 5 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,

Speaker 5 I was raised by parents who

Speaker 5 were very,

Speaker 5 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?

Speaker 5 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.

Speaker 5 So, for instance, 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.

Speaker 5 So what I did is I didn't take shortcuts, I just was trustworthy. And I invested in people and I,

Speaker 5 you know, I developed relationships and I was very intentional about

Speaker 5 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?

Speaker 5 And over time, you know,

Speaker 5 I think people sense that you're a trustworthy person and that you are really deeply invested in

Speaker 3 their outcome.

Speaker 5 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.

Speaker 5 doing events, you know, expanding the time that you spend together outside of just poker and, you know, doing events with

Speaker 5 the whole crew. And

Speaker 5 so that's what I focused on. And that

Speaker 5 was so incredibly valuable.

Speaker 4 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.

Speaker 4 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

Speaker 5 what shocked me was if you looked at the net worth at a lot of these people that were playing,

Speaker 5 it would indicate that a loss of a couple hundred thousand or even a million wasn't a big deal, right?

Speaker 5 But that's that wasn't the case.

Speaker 3 I saw crazy behavior.

Speaker 5 And

Speaker 5 what 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?

Speaker 5 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.

Speaker 5 Even though it doesn't 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.

Speaker 5 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.

Speaker 5 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.

Speaker 5 Then they're both in fear, then they get into the sparring match games and things fall apart.

Speaker 4 So it was

Speaker 5 useful for me to just be able to emotionally regulate myself and understand

Speaker 5 what was going on.

Speaker 4 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.

Speaker 5 Well, I've been stiffed and I wrote those checks.

Speaker 4 Really? What's the biggest you got stiffed for?

Speaker 3 $250.

Speaker 4 $250. And the person could afford to pay it.

Speaker 5 For sure.

Speaker 4 And they stiffed you. For sure.
And then you've got to come out of pocket for that and make good.

Speaker 3 Yeah. Yeah, that's hard.
Yeah.

Speaker 5 But it teaches you to do a really good job on the on the vetting.

Speaker 3 Yes.

Speaker 5 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?

Speaker 3 Yeah.

Speaker 2 So Molly, can you just talk about,

Speaker 2 you talked earlier with us when we were playing poker or during lunch about

Speaker 2 someone said, I think, what sort of stuff are you into?

Speaker 3 Yeah.

Speaker 2 And you said, I'm really into like adrenaline stuff, like adrenaline sports, right? And you're like competitive skier and so on.

Speaker 2 But this feels like that sort of high-stakes environment that you put yourself in. Where did that come from?

Speaker 2 And do you think you selected yourself into this environment because it feels like hella skiing?

Speaker 5 I think, first of all,

Speaker 5 I come from a really competitive family.

Speaker 5 One brother

Speaker 5 went to the Olympics twice, was a world champion in mogul skiing at world champ at 16.

Speaker 5 Then he went on to, after the Turin Olympics, get drafted fifth round of the Philadelphia Eagles.

Speaker 3 He was an Abercrombie model.

Speaker 5 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.

Speaker 5 And then my other brother is Harvard-educated cardiothoracic surgeon at MassGen.

Speaker 4 Which one do your parents love most?

Speaker 5 Well, they loved them more, but then Costner played my dad in a movie, so I became instantly the favorite kid.

Speaker 3 So they eventually loved you.

Speaker 5 Eventually, but it took a, I mean, 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.

Speaker 5 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.

Speaker 5 And so something started to happen, I think, in those early years where it was like this

Speaker 5 very

Speaker 5 exciting experience to look at something, be afraid of it, and then do it.

Speaker 4 Like, run a big game. That one goes out for 250K, and then you decide, hey.

Speaker 2 But that was the behavior you were trained on early on.

Speaker 5 I think it was a byproduct of socialization.

Speaker 2 Steer in the face and jump into it. Yeah.

Speaker 5 And that's a pretty great feeling, right?

Speaker 3 Totally.

Speaker 4 And a bit of pride. You wanted to restart the game.
And so you had that pride. Big time pride.

Speaker 4 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.

Speaker 5 Okay, so

Speaker 5 moved to New York.

Speaker 5 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.

Speaker 5 And what I found was that there is a problem with trust. A lot of times...

Speaker 5 game runners are playing their own games.

Speaker 5 If they did had a bad night, the rake would be higher. Da-da-da-da-da.
I wasn't taking a rake.

Speaker 5 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

Speaker 5 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.

Speaker 5 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.

Speaker 5 It was 2008, and I remember the first game. The president was in the background on the television, like giving the state of the union on the economy, and there was like $10 million on the table.

Speaker 5 These were

Speaker 5 insane games. They were playing insane variations of and you love the thrill.

Speaker 2 You feel the thrill.

Speaker 3 I did, yeah.

Speaker 5 I mean, this was the game that, like, ultimately, someone lost 100 million.

Speaker 3 So,

Speaker 5 so, yeah, so again,

Speaker 5 that definitely made noise even by Kuhn standards.

Speaker 5 And yeah, so, and then I just decided, you know, because I told my parents, listen, because they're like, please go back to school, you know, please finish your, like, go to school.

Speaker 3 You knew what you were doing. Yeah.

Speaker 5 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.

Speaker 5 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.

Speaker 5 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 in my poker game.

Speaker 5 The next thing that happened was

Speaker 5 the Italian mob or impersonators of the Italian mob

Speaker 5 came to me and said, you know,

Speaker 5 we want a piece of your game. And I turned them down.
And then they didn't just go away.

Speaker 5 And they sent someone to my apartment And

Speaker 5 this guy broke in my apartment and he put a gun in my mouth.

Speaker 5 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.

Speaker 5 And then he beat the hell out of me and forced me to, like, you know, you.

Speaker 5 took everything out of my safe and there was money and there was a gold bar in there for some reason but also um 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

Speaker 5 for what I was now implicating my family in and I couldn't call anyone and wow I kept waiting for their did you think at that moment to just stop and just say you know what okay done

Speaker 5 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 they'd said this is a warning It's not up to you anymore.

Speaker 3 Wow.

Speaker 5 So I didn't know what to do, like, literally, for the last time.

Speaker 2 Were you confident in anyone?

Speaker 5 I didn't tell a single soul.

Speaker 2 You kept that all in? Yeah.

Speaker 5 And I'm in my apartment. I can't go outside because it's very clear I've been assaulted.

Speaker 5 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.

Speaker 5 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.

Speaker 4 Dodging the bullet,

Speaker 3 but yeah, but then

Speaker 5 the bullet of me came into play. And, you know, so then I just started getting out of control.

Speaker 5 And like I said, like, you know, integrity was an important thing to me, but over time, I was making these little decisions. They were just a little left or right of

Speaker 5 where I stood. And, you know, greed,

Speaker 5 money, it became everything. And so I started doing things that

Speaker 5 my attorneys told me not to do.

Speaker 4 Raking the game?

Speaker 5 Yeah, taking a rake.

Speaker 4 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.

Speaker 4 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.

Speaker 4 And you can't do that at a home game.

Speaker 4 And so now you are breaking the law

Speaker 4 to make extra money.

Speaker 7 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.

Speaker 3 And like a scene, they do an hourly rake, right? Yeah, that's a rake too. That's a rake too.
Yeah.

Speaker 4 Different ways.

Speaker 7 You were taking money out of the pots, keeping them for yourself.

Speaker 5 So basically, what I was doing was I had become much more lenient about who I was letting in the game.

Speaker 5 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 break.
This was the last six months.

Speaker 5 The feds had put a confidential informant in the game because they were listening to the Russian phone

Speaker 5 who tracked that.

Speaker 5 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.

Speaker 5 And I just wanted to go home, even though I pushed my family really far away. Like, I just wanted to go home.
So I tried to book a plane ticket from

Speaker 5 JFK to Denver, and my credit card got declined. And then my next card got declined, and I logged into my bank account, and it read negative $9,999,000.

Speaker 5 The division of asset

Speaker 5 forfeiture

Speaker 5 had taken everything. Because your property, unlike your personhood, doesn't have the presumption of innocence, except for maybe in Florida.

Speaker 3 Wow. I'm not up on the asset for sure.
So now you're pinched.

Speaker 4 You get shaken down by the mob, then you get pinched by the feds.

Speaker 5 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?

Speaker 5 Are you pursuing any criminal charges? They said, no.

Speaker 5 I

Speaker 5 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,

Speaker 5 moved moved back into this little studio apartment. And I thought, okay, it's a fresh start, you know.

Speaker 5 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.

Speaker 3 Wow.

Speaker 3 What a year.

Speaker 3 I was really running hot. Yeah.
Wow.

Speaker 4 A couple of bad beats.

Speaker 5 So I had a day and a half to get to New York City to find an attorney.

Speaker 3 And you're broke. And I don't have a penny.
Yeah. Wow.

Speaker 3 How does it all resolve?

Speaker 4 How does the story resolve?

Speaker 5 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.

Speaker 5 And 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.

Speaker 4 Who were for poker, specifically?

Speaker 3 Yeah, let me be really clear.

Speaker 5 There was no Epstein in my game.

Speaker 3 Right. Right.

Speaker 5 So they said if, you know, if you...

Speaker 7 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?

Speaker 3 Like murder plots?

Speaker 7 Or like, like, what, like, what were you going to be able to tell them? Business deals?

Speaker 5 I could have given them leads.

Speaker 3 Could you overhear

Speaker 3 all kinds of stuff? Yeah. Crime.

Speaker 5 For sure.

Speaker 3 Wow.

Speaker 4 Is this Preet Barara, who is running the Southern District? Because he's also famous for getting rid of online poker.

Speaker 4 He's a pretty by the books guy.

Speaker 3 For sure.

Speaker 4 Yeah. Yeah.
And the Southern District, of all districts, is known for being the most hardcore.

Speaker 5 And

Speaker 5 politically ambitious.

Speaker 5 Sure, right.

Speaker 3 Right.

Speaker 7 And they said. So did you go to jail?

Speaker 3 I didn't.

Speaker 5 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.

Speaker 5 And I had like 48 hours to make this call.

Speaker 5 And, you know, where I got to it was like,

Speaker 5 this was my fault.

Speaker 5 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.

Speaker 5 And so to turn around and drag these people who had families through this bullshit

Speaker 5 based on my

Speaker 5 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.

Speaker 5 And I got a judge who was very disappointed in my life choices.

Speaker 5 But basically said, you know, you had a life before this. And I had character letters from professors and ski coaches.
And I had

Speaker 5 a lot of people show up for me that had made better decisions that I had in life. And so he fined me a lot.

Speaker 5 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.

Speaker 5 Like, where, how do you come back from that? You know?

Speaker 5 And so I decided,

Speaker 5 Well, there's a story here. And if I can monetize that, maybe

Speaker 5 that can address the reputational harm the financial I mean I'm millions of dollars in debt and

Speaker 5 and so I wrote a book and

Speaker 5 waited for my life to change and then I think ten people read it and probably like eight of them were related to me

Speaker 5 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 shortlist of the most successful filmmakers in Hollywood and I was like why not You know, why not just go for it?

Speaker 5 But they needed to be brave because there was also a ton of people, as you can imagine. Yes.

Speaker 5 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.

Speaker 5 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?

Speaker 5 It's a good bet.

Speaker 5 Anyway, getting to him wasn't easy. I finally got to him.

Speaker 5 And I just remember before I walked in, I was like, what am I doing? I've

Speaker 5 millions of dollars in debt. My book sold 10 copies.
Like, I live with my mom.

Speaker 5 And this is the highest paid screenwriter in the world, you know.

Speaker 2 So you got a meeting with him. I did.
And he had, you had sent him the book, obviously. So

Speaker 5 somebody that I bothered like relentlessly. Right.

Speaker 2 So you're just to put the sales hat on again. Yeah.
Like the relentless pursuit of the sale. Yeah.
You were like all over this guy, even though you weren't making, and you just kept going.

Speaker 5 Yeah. And

Speaker 5 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. You live with me.

Speaker 4 What does he say when you get in the room?

Speaker 5 So I told him my story.

Speaker 5 And I think

Speaker 5 my legs were shaking, but I had this game face on.

Speaker 5 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.

Speaker 4 Wow. It's a good character study, yeah.

Speaker 3 Yeah.

Speaker 3 And then, you know.

Speaker 4 They made an offer. Yep.
And then the rest of it history, and then you used that money to pay down this fine you got? I did. And

Speaker 5 I just finally finished paying off the government last summer.

Speaker 3 Wow. Congratulations.

Speaker 3 I don't have any doubts.

Speaker 4 And I guess, you know,

Speaker 4 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?

Speaker 4 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 out. Everybody was really scared about it.

Speaker 4 You didn't put people's names in it. You specifically chose to, you know, make it.

Speaker 5 They put their name in it

Speaker 5 if they had talked about playing in the games. Right.
If they've themselves, you know.

Speaker 4 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.

Speaker 4 But there was no non-disclosure. You hadn't made any agreements to not talk about it.

Speaker 3 Well, I didn't turn on them.

Speaker 5 I actually supported them at every turn.

Speaker 5 Well, I'm just saying, like, I could have gotten a lot of money back and a deferred prosecution.

Speaker 4 Okay, yes, in that case, yeah.

Speaker 5 And then the publishers were willing to pay me six, seven figures for a celebrity hit piece.

Speaker 3 I was broke living with my mom.

Speaker 5 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.

Speaker 3 Great. And

Speaker 4 the few still matches you know is everybody who had games, all the dealers, everybody involved had to sign non-disclosures for the next.

Speaker 3 Probably smart. Probably smart, yeah.

Speaker 2 Do you still need to face fear in its face to feel like you're

Speaker 2 doing what you want to do? Yeah.

Speaker 5 I don't have this, I think, addiction to that anymore.

Speaker 5 But I don't, I don't ever,

Speaker 5 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,

Speaker 5 that

Speaker 5 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,

Speaker 5 I needed to do a lot of work on myself

Speaker 5 so that I could be the kind of thing.

Speaker 4 You learned a lot about yourself.

Speaker 3 Yeah, too.

Speaker 4 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.

Speaker 4 What have you learned about the nature of these men?

Speaker 5 Well, again, I think

Speaker 5 I don't like to.

Speaker 5 There's a couple different archetypes, okay?

Speaker 3 Tell us.

Speaker 3 So

Speaker 5 there are the ones that are there on a

Speaker 5 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 and

Speaker 5 ways. There's drugs.
There's, you know, it's, it's... It's the hedonic treadmill gone crazy.

Speaker 5 No more control over themselves, living for that next fix.

Speaker 5 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.

Speaker 5 And,

Speaker 5 you know, and then I think there are people that play

Speaker 5 because they love the game,

Speaker 5 because they like the aspects of it that make it an incredible game. They like the psychology.
They like the

Speaker 5 making, you know, seeing the results of making high-level decisions with very limited information. They like the mental

Speaker 5 and social thrill of it.

Speaker 3 The camaraderie and the competitiveness.

Speaker 7 Who's the best celebrity poker player

Speaker 7 in all the years that you saw in these games? Who is the best? Toby. Toby.
Yep. And who is the second best?

Speaker 4 He wants you to say Chamoff, but we would have carved him out because he's not a celebrity.

Speaker 7 Look, I've played with Toby for 20 years. I would have said Toby, too.
I think he's exceptional.

Speaker 3 He's a grinder. He's tough.

Speaker 5 Yeah, he's tough. I mean,

Speaker 5 he was the only one in the game that was tight. Yeah.

Speaker 5 I guess second would be Ben.

Speaker 3 Yeah.

Speaker 7 Affleck's a good player. Yeah.

Speaker 5 He's definitely smart, definitely knows what he's doing. It depends on where he is in his life.

Speaker 3 Yes, yes.

Speaker 7 Politician-wise, can you say, or no?

Speaker 5 I haven't named any of the politicians because they haven't been named.

Speaker 4 Yeah. Okay.

Speaker 7 Business people?

Speaker 4 once again, they haven't named themselves, so we'll leave them unnamed.

Speaker 2 Molly, you were telling us before that you do some kind of

Speaker 2 speaking work around sales. This is where I'm so interested in this.

Speaker 2 What are the things you tell people when you do those events? What is the big takeaway from your experience?

Speaker 5 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,

Speaker 5 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

Speaker 5 what are people most afraid of they're afraid of um not belonging not uh being worthy people stealing money from them etc and so when you start to think about what

Speaker 5 what kind of emotional footprint am I leaving with these people? Like,

Speaker 5 you know, like, 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,

Speaker 5 what's my resume? What are my sound bites? What's my pitch? Instead of thinking,

Speaker 5 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 things that you could do.

Speaker 5 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

Speaker 5 to you know have some warmth about you and some

Speaker 5 you know like be affirming but also be authentic

Speaker 5 and

Speaker 5 and

Speaker 5 to practice the hard empathy like the easy empathy is people you relate to people that have a similar experience to you.

Speaker 5 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.

Speaker 3 Making that effort.

Speaker 5 Yeah, making that effort. And

Speaker 5 it's interesting,

Speaker 5 humans hate uncertainty.

Speaker 5 Without an edited brain, and I mean edited by doing that work and meditation,

Speaker 5 whatever your mind training tool is,

Speaker 5 the brain thinks that uncertainty is a metabolically unsustainable state. So it equates uncertainty with fear.

Speaker 5 So how can you start to give people that sense of certainty?

Speaker 5 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,

Speaker 5 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.

Speaker 5 You know, there's a lot of things that aren't so obvious or instinctual

Speaker 5 in the art of impact and connection.

Speaker 2 It can also force you to let go of priors,

Speaker 2 which allows you to adapt and evolve.

Speaker 5 I mean, being able to adapt and being able to court change and even reframe it as like, this is exciting or this is interesting.

Speaker 4 What an incredible life you've had, ladies and gentlemen. Let's thank Molly for joining us.

Speaker 3 Thank you, Molly. Thank you so much.

Speaker 4 And Mitch Nipe also, Orato, thank you for hosting.

Speaker 2 And my lord, we're going to have a great weekend.