Molly's Game with Molly Bloom

0:05Every now and then I get to meet a person who has a story that is more remarkable than any fictionalized version that any of us could come up with. Molly Bloom is one of those people. If you ever saw the movie or read the book Molly's Game, then you know what I'm talking about. She ran an illegal poker game in Los Angeles and New York, in which on some days people would win or lose a hundred million dollars. The mob got involved. She had a gun put in her mouth, federal prosecutors, hidden wiretaps. The story's absolutely insane. And her accounting of it is even more incredible. But the thing that inspired me was Molly's feeling of accountability.

0:50How she recognized that she made her own decisions, that she was responsible for the repercussions, and how she took total ownership of everything that happened. The rest of us could really learn a thing or two about what it means to take responsibility. This is a bit of optimism.

1:14Molly Bloom, I have to tell you, I was so excited that you were willing to come and have a conversation because I've seen the movie Molly's Game, and I know you wrote the book on the same topic and lived the life. And had I not known that it was real, I would have said, the story is way too fantastic to have actually happened. What crazy mind could actually come up with this incredible work of fiction only to discover that it's a hundred percent real, that this was your life. And of course, after seeing the movie, went down the rabbit hole of like Wikipedia and reading all of the news stories because I couldn't believe it actually happened.

1:51than it did for the people who haven't seen this brilliant movie or read this brilliant book. And I know you do this a hundred times. I apologize. What is the thing that you did that I find completely insane? I also find it completely insane at this point in my life. So when I tell the story, I'm like, did I really do that? So I was a pretty normal kid. I grew up in the small town in Colorado. My brothers and I loved mogul skiing. We are competitive mogul skiers. We started competing and wanted to go all the way. And I just had what I thought was this set path. I was going to ski for the U S ski team.

2:31And then I was going to go to law school. And there was just no question, no deviation around that. It was, that was my plan. And, you know, I got thrown a little curve ball. I got really bad scoliosis, had this crazy surgery in which they used 11 of my vertebrae together and basically made my thoracic spine immovable. and I was a mogul skier. So that wasn't ideal. And, you know, everyone was just like, you're going to probably have to find a new hobby. But for me, it wasn't my hobby. So I got back on the mountain and I guess it was the first time in my life that I experienced this ability we have to go against experts and parents.

3:12And maybe this is where it all started. Anyway, so I ultimately made the U.S. ski team. I was really doing well. I was third overall in North America at this crazy, you know, one in a billion odd situation in which I was at the Olympic qualifier, skied over this little tiny piece of pine bough and my ski pre-released in the air and I crashed and ultimately made this decision that I was going to retire from skiing. And I had just taken the LSATs and I was, you know, ready to sort of pull the trigger on that part of the journey. But for the first time in my life, I was so heartbroken and so just disjointed that I couldn't get it together.

3:53So I decided I was going to take a year off just to be young and be a kid. And I really just wanted to go somewhere warm because I'd been chasing winter my whole life. And because this is one thing that I don't think a lot of people, maybe they do realize when you decide you want to be an Olympic athlete, that is your 24 seven job. I mean, you train your relationships, you sacrifice, you miss birthdays, you miss Thanksgiving, you know, you miss all this stuff because all you do is focus on the Olympics. And now that that is gone, you've missed out on childhood basically. So now you want to go reclaim a little bit of youth.

4:25Yeah. See what it's like. So I went to Los Angeles and I got a million jobs. And one of them was working at this real estate development company. And my boss told me one day, I'm going to have a poker game and I need you to serve drinks at it. And that was the rabbit hole. I just remember being 23 and a half years old and walking into this room. And it was, yes, sure, there were A-list movie stars, but there were also politicians and the head of one of the biggest investment banks and somebody who just brought their tech company public. I mean, this room was insane. And it was so compelling to me.

5:10This was access to information and people were speaking so candidly. And then at the end of the night, I made like$3 ,000 for refilling Diet Coke. So this is a good gig. This is a great gig. And I just became more and more fascinated with the world and the world of the world of high stakes gambling to some degree, but more of this unconventional underground sort sort of masters of the universe setting. Like this is the kind of stuff where conspiracy theories come from, which is that there's a small group of people controlling the world. Turns out you were in that room serving Diet Coke. Right.

5:51And I started to just really understand that I had this skill set that I wasn't aware of. And that was that it was an entrepreneurial skill set because I would see how things were done and I would see a way to do it better. And I was quick on my feet and I was a problem solver. And so I decided to start my own games with the intention always being, I'm going to do this for a couple of years. Then I'm going to go to law school because I'm a serious person and I want a serious life. But this is an opportunity to save some money and to make these incredible connections. I started making millions of dollars a year.

6:28Millions? Millions of dollars? Yes, millions of dollars a year. Just out of curiosity, how do you make the money when they're playing poker? That's a great question because I was really at this point and for many years, I was very set and determined to only do it if it was legal. And so I hired attorneys and they analyzed the federal statutes and they said, listen, as long as you're not taking a rake, which is what they do in Vegas. What does a rake mean? A rake means when the players bet, the house takes a percentage of the pot. Because if you were taking a rake, then you'd be an unregulated casino, which is illegal.

7:03That's right. And so what happened was my game became the go-to game. It was all action. The stakes were high. You could sit next to the biggest movie stars and the biggest business people in the world. And there were nine seats and I was in charge of those seats and I was also in charge of how much credit was extended. So there was this unspoken rule that emerged that if you wanted your seat back the following week, and if you wanted credit, and you won at the game, you tip Molly. And so, you know, people were winning millions of dollars at these games. So you can imagine if they're tipping even just a percent, a couple percent over time, then it was incredibly lucrative.

7:44And it was incredibly exciting. I mean, how big are these pots that people are winning millions of dollars? Simon, I'll tell you that by the time I got to New York and I'm kind of skipping ahead, there were games in which people would win and lose$100 million in a night. What? It was just... I can't even fathom that. I couldn't either. And I can't now. It seems like a fever dream. That's generational wealth. For sure. That you lose or win in one night. Right. Playing poker. Right. Okay. So we're skipping ahead. I recognize you were running a quote unquote legal game. So when did it become illegal?

8:30So I had this very naive, optimistic idea that I could be the one honorable, heart-centered person in the underground gambling world, you know, and it wouldn't get to me. You know, I would, I would just be able to retain who I was. And I ran the games for eight years and I would say six and a half years into it, seven years into it and not overnight by inches, I found myself looking in the mirror and not even knowing who I was anymore. I was raised in a household that really was about value-driven living, not in a religious way, just moral courage and integrity and doing the right thing. And that drove me and that centered me for a while.

9:22But you have to know who I was hanging out with, you know, the company I was keeping and the world that I was in. And everyone was trying to steal my game and screw me over and steal money from me and cheat. And it was a world that was like completely about worshiping money and the hustle and gamble. And I got caught up and I started to make choices that were not aligned with this core center. And I lost the plot. I mean, where do we start? Before we talk about the moral sharp turn, I'm just curious, what was the reason your legal underground game where you made money by taking tips became illegal?

10:06In LA, what I had was pretty sustainable. It was manageable. I had one big game I did once a week. When I went to New York, I built it out. I mean, I went all in. I had this huge game in which people were winning and losing$100 million a night. I had the mid stakes and the low stakes and the derivatives of Texas Hold 'em. And I started to take risks on people. And I was the bank by this point. So if somebody didn't pay their debts, I wrote the check. And that was what made my game so popular, one of the components. And I started to make some bad choices. And my debt sheet started to grow bigger and bigger.

10:45And I started to put people in seats that if they won, it was going to be okay. But if they lost, it wasn't. I was gambling on people. And so at some of these games where I had more exposure, I started taking a rake to cover my downside and to try to make good on this debt sheet. But I, you know, up until this point, I had a great thing going on because it was reputational suicide to stiff this game. And there wasn't another game out there that was like it. So when I did my job well, and I had, I'm sure the statute of limitations has passed on this, and I'm not even sure if this is a crime, but like I had bank employees on my payroll.

11:23I had private investigators. I vetted people really well and got very good at it. And then I just got sloppy. Did you become like your gamblers? If you just play a nice game of poker, you can win a little, you can lose a little, you know, it's like the rule of gambling. When I go to the casino is what would I pay for a night out? Cause I'm not going to get that money back. If I buy dinner or whatever or a show. I'll gamble that. And if I lose it, that was my night out. But you're having people who are literally spending more than they can afford to lose. And you are now becoming like them, which is you're now taking bets with the hope that you will hit it big on this player.

12:04But when they lose, you lost big. There's this ethical creep of greed. There's an ethical creep of greed. And I think there's also a piece of it that's addiction. and addiction to what well in my case i think it was the adrenaline most of the players that were playing at the level of losing a hundred million dollars i think they were gambling addicts and that at some point starts to get into your psyche and really made me question who I was and what I was doing in the world. Okay. And now we have to get to the conclusion of this part of your career, which is it collapsed. Yeah. Do you know what I find fascinating about this?

12:51Like so many things, which is it could have been fine if you didn't get greedy. You were making, as you said, millions of dollars in LA with your weekly game, which is still the game to be in. And if you were satisfied making millions doing a weekly game, we'd be talking about this game that you continue to run to this day, this multimillionaire, but greed. Millions wasn't enough. No, no. And I also think there was a piece of it that was a bit self-destructive because I didn't like who I'd become. Anyway, so the thing blew up. It was multifactorial. First, there were some Russian-American businessmen that were playing in one of my games.

13:35She just made air quotes.

13:39and their stories checked out but i i knew in my gut that something was off yeah and it turns out they were running the biggest insurance fraud scheme in new york city history and the feds were listening to their phones and they would come and always paying cash you know it was and then the second thing that happened was one of the players in la who we nicknamed bad brad he comes he's the worst poker player I've ever seen. And he doesn't get better. He doesn't seem to understand the simple rules of this game. And he would come and he would lose hundreds of thousands of dollars every night. At this point, I was like, Brad, I don't think you should play anymore.

14:17And he was like, no, no, I love it. These guys are my friends. Please don't take my seat away. So then it turns out Brad starts talking about his returns from his hedge fund. And everyone's like, oh, Bad Brad's a savant in trading. So they all start investing with him. So Bad Brad lost $5 million in the game. He raised$30 million for his fund, which turns out to be a Ponzi scheme. So everyone thought they were hustling Bad Brad, but Bad Brad was hustling everyone. And so not only did we have to pay back the 5 million, they all lost their investment. So that happens. Somebody's lawyer leaks the depot to the tabloids.

14:57So now it's on the radar. Then I had a run in with the Italian mob because, oh, by the way, and the Russians that were running that insurance fraud scheme had alleged ties to the Russian mob. But now we're talking about the Italian mob. I was the biggest game runner in New York City. And they came to me and said, you're going to have to give us a piece of your operation. And I tried to explain very logically why I couldn't go into business with them. And they didn't respect that. And they sent this guy to my apartment who put a gun in my mouth and beat me up and gave me this very terrifying message that if I told anyone and if I didn't acquiesce to their demand that they were going to hurt me and find my family in Colorado.

15:46And I didn't know what to do. I was so, for the first time in my life, just had no idea what to do. Didn't call the cops, didn't call my family. And then a week later, I hadn't heard from them. And I got the New York Times. And on the cover, it said 125 arrested in the biggest mob-related takedown in New York City history. So I never heard from them again. And then the last thing that happened was I started taking the rake. The feds had put a confidential informant in my games at this point because they are listening to - They found your crime by accident. Right. Exactly. Yes. And then later that year, one of my poker dealers texted me and said, the FBI is here looking for you.

16:30And I immediately started packing a bag for the airport, tried to buy a plane ticket from JFK to Denver. My credit card gets declined. My debit card gets declined. I log into my account and my account balances, reads negative 9 ,999 ,999. Oh my God. you know i make it home the fbi doesn't apprehend me my attorneys call the feds and they said your property unlike your personhood doesn't have the presumption of innocence and we believe on good authority she's been making her money illegally if she wants to come in and go on record and tell us how she's been making this money and more details about this interesting career she has we'd love to have that conversation i couldn't do that and the last thing my attorney said is, do you want her to come in?

17:19Is she part of this investigation? And they said, no. And if she is, we'll let you know. And so that led to, I just went away. I moved in with my mom, you know, in the mountains of Colorado. And I felt really sorry for myself and had to figure out a way, you know, this has been in the tabloids now and there's all this, all these rumors. My network is destroyed. I, I need a job badly. I don't have a bank account. I don't have any money. Well, you do have a bank account. It's got negative$9 ,999 ,000. Yeah. So I would have to deposit$10 million in order for it to be a functional bank account. I had to do two really important things.

17:59I had to, first of all, look at this mess and own the fact that this was entirely my fault. And I had all the information on hand. I had all the opportunities in the world to do something that wasn't illegal. And here I was. And then, you know, I had to try to figure out how to come back from this. So two years go by. Oh my goodness. You think you like, okay, I fucked up. I got to get out of jail free card. Literally. I'm going to put my life back together and never make this mistake again. Two years go by. I got sober because as you can imagine in that world, I was in the substances and alcohol and pills and everything were, were a big part of it.

18:44I got sober. I got, you know, started meditating. I looked at the whole mess. I took responsibility for it. I got a job. I moved back to LA and seven days later in the middle of the night, I got arrested by 17, 17 FBI agents with machine guns and high beam flashlights and they put me in handcuffs and they put this piece of paper in front of me that said the United States of America versus Molly Bloom. And I had a day and a half to get to New York City to find an attorney that's going to represent me in this, the fight of my life. I don't have a dime. And, you know, I had eight meetings with attorneys the day before the arraignment.

19:26And this is a terrifying indictment. This is a Russian mob indictment. 95 % of the people that are indicted, I've never heard of in my life, including some guy who lives in Moscow, who's known as the Vore, which is like the godfather of Russian organized crime. I mean, life does not make sense. There's no way to grasp it. And I finally found this attorney. His name's Jim Walden. He was at Gibson Dunn at the time. And he was like, you need help. What you do in the next couple of weeks is going to determine the rest of your life and I'm going going to help you. And I basically had to give him an IOU for the retainer.

20:02And we started working together and the prosecutors wanted a meeting. And this is - He afforded you credit. He did. He gave me credit. He thought I was - Oh, the irony. Right. Exactly. I paid him back every cent. So I start working with Jim and the prosecutors want a meeting. and this is the southern district of new york this is you know a very big prosecutorial office and and they really wanted me to become a confidential informant and they weren't interested in the mobsters or the russians they were interested in celebrities in the hedge fund managers and in the politicians and things that they wanted to know i didn't know any epsteins or Weinsteins.

20:51I didn't know people that were doing really terrible things. I knew people that were maybe betting sports or doing some sort of shady, hedonistic stuff, but I didn't know, in my opinion, I wasn't going to be making the world a better place by becoming a confidential informant in this case. All I was going to do was shirk the responsibility of the consequences of my actions and destroy the lives of other people, many of whom I knew their kids, you know, and I knew their wives. Did any of them come to your aid? I mean, you'd looked after them, some of them you'd extended credit and they were quote unquote, your friends.

21:33Did a single one of them call you up and say, can I give you some money? Are you okay? Did they even call you up and say, are you okay? No, but again, you know, I mean, they don't owe you anything, right? They don't owe me anything. I didn't ask for anything. And I wasn't, you know, it wasn't the Peace Corps. It was on the underground gambling road. And you weren't friends. No. Would I have hung out with them if I wasn't making millions of dollars by their gambling? 99 % no shot. So I turned the offer down and I waited to get sentenced. And we all thought I was going to go to federal prison. And my life was, again, a total disaster.

22:09And my father and I weren't speaking. Wait, wait, wait. Back up a second. Molly Bloom running an illegal gambling ring interloping with the mob even if it wasn't by choice all of a sudden you find moral high ground where so what let a couple of celebrities and politicians get investigated by the feds and be humiliated and so you can stay out of jail like why didn't you take that deal I think most reasonable people would have taken that deal to stay out of jail so it wasn't for them it was because I had this experience of what it feels like when I acted not in alignment with what I believe in and who I am.

22:46And I hated myself and I didn't want to fight for myself anymore. And this like almost delusional confidence that I'd always had was gone. Was it less moral high ground and more giving up? No, because I had been in that place and I'd come out of that place. I had done all this work. I had a very strong sense of pride that these were my choices and I was going to stand for them. You actually were willing to take accountability. I was. I needed to take accountability. Okay. There's a piece of it that's moral and there's a piece of it that's also strategic. I want a life after this. Yeah, but you could have stayed out of jail.

23:25This was my thought. And Jim Walden wanted to correct me every time. But I was like, listen, if I spend two years in a federal prison, I'll learn a language, whatever. I can get through it. Get into shape. Like I will make sense of the time there and I am good at making money. So I'll just make more money. The other one seemed like an unknowable, unendable life sentence. How long and to what degree are the feds going to use me and destroy my life? It was something awful, but finite versus something less awful, but forever. And something that gave me, and this has always been important to me. And you can ask my family because I would open my mouth no matter how much trouble I got in.

24:09And I always got in trouble. I have to have agency. Like I have to feel that I have some sort of internal power. You know what I find interesting is everybody told you stop skiing. You didn't listen to people who knew more than you. And you broke your back. You destroyed your skiing career. Then you go into something that was very profitable, but greed got the better of you. And I'm sure people told you, don't do it. Just stick with what you've got. You got a good thing going. Don't ruin a good thing. And you ignored the better advice and the whole thing crashed in on you. And now everybody's telling you, take the deal, take the deal.

24:54You're an idiot. Take the deal. You ignore the better advice, but this is actually the right choice. So, one out of three. Well, it's less one out of three. What I think is curious is, what was it about your gut that was different the third time of ignoring? Here's the answer to your fascinating and I think very intelligent question. And no one's ever asked me this, and I've never really thought about it this way, but the answer to me is really clear. I grew up in this family with two brothers who were so successful right off the bat, and their success was so defined. My younger brother was number one in the world in mogul skiing at 16 years old.

25:35He went on to have a prolific college football career and Olympic career in skiing. And then he got drafted fifth round of the Philadelphia Eagles after the Turin Olympics. He won, you know, multiple world championships. He was like an Abercrombie model during these years. Please tell me he's an asshole. I wish, but he started a charity in our hometown. 21 for like granting wishes for senior citizens because he was worried about them oh i hate him and most recently this kid who we just thought was a really good athlete like started and sold a software company all right so this is little brother just a prodigy model like empath okay and charming and lovely and all the generous and kind and ethical oh and then my middle brother's even worse he's a harvard educated cardiothoracic surgeon at Massachusetts general who's dedicated his life to helping children with congenital heart defects.

26:34And here I was at 35, like millions of dollars in debt of social pariah, convicted felon, like the family felon, you know. But to get back to your question, I felt in the shadow of my brothers and I was going to go and do something and be something no matter what. And my biggest fear was that I wouldn't and then and I would fail and then I failed so spectacularly and there was such a moment of liberation about that failure because it was like okay like literally I'm the family felon and look at these two you know sports hall of fame Harvard med school like I'm not even in the running anymore so great and then that gave me the freedom to really start to become who I was without this rage to sit at the table with my brothers.