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The Diary of a CEOThe Diary of a CEO

"He Put A Gun In My Mouth, Then Beat Me Up!" - Molly Bloom (Molly's Game)

A crazy story...with a dark, unbelievable, ending. Welcome to Molly's game. 00:00 Intro 02:01 The Pressure to Be a High-Achiever 04:55 I Was Chasing Glory 06:16 Finding My Way in LA 07:33 Becoming the PA of the Biggest Poker Game Organiser 10:01 Entering the Poker World & Its Secrets 12:18 The Psychological Strategy Behind Your Success 17:41 Playing the Manipulation Game 19:55 Running the World's Most Exclusive Poker Nights 24:47 He Wanted My Money Or Would Take My Poker Nights from Me 28:54 Do You Resent Him? 31:42 Taking Over the Poker Scene in NY 36:18 Someone Lost $100 Million, & It All Started a Bad Spiral... 42:41 I Compromised My Integrity 44:37 The Downfall: The Crashing Impact on My Health & Relationships 48:14 The Italian Mafia Put a Gun in My Mouth 54:53 The Terrifying Moment When the FBI Came After Me 58:25 Facing 10 Years in Prison 01:03:00 They Offered to Give Me Money if I Snitched 01:08:44 What Did You Learn from This Experience? 01:11:55 How My Story Became a Hollywood Success 01:20:37 Going Through IVF 9 Times 01:24:04 What's Your Advice for Being Successful? 01:27:54 What Are You Proud Of? 01:29:37 Last Guest’s Question You can purchase Molly’s memoir, ‘Molly’s Game’, here: https://amzn.to/47oDhDS Follow Molly: Instagram: https://bit.ly/3KKe0Lk Twitter: https://bit.ly/45tjBOe My new book! 'The 33 Laws Of Business & Life' pre order link: https://smarturl.it/DOACbook ....https://bit.ly/47vPoQf Join this channel to get access to perks: https://bit.ly/3Dpmgx5 Follow me: Instagram: http://bit.ly/3nIkGAZ Twitter: http://bit.ly/3ztHuHm Linkedin: https://bit.ly/41Fl95Q Telegram: http://bit.ly/3nJYxST Sponsors: Huel: https://g2ul0.app.link/G4RjcdKNKsb

Molly BloomguestSteven Bartletthost
Aug 17, 20231h 34mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:002:01

    Intro

    1. MB

      He put a gun in my mouth, beat the hell out of me, and he- he said, "If you tell anyone about this, I know where your family lives." For the first time in my life, I knew finally it was game over. I'm Molly Bloom.

    2. SB

      Dubbed The Poker Princess.

    3. MB

      The former waitress who-

    4. SB

      Took a small poker game run out of a dingy nightclub-

    5. NA

      To the biggest underground poker game-

    6. SB

      In the world. From Hollywood celebrities to millionaires.

    7. NA

      They literally made a Hollywood movie about it.

    8. SB

      The game turned from legal to illegal.

    9. MB

      I had become the biggest game runner in New York City. Leonardo DiCaprio, Ben Affleck, and Tobey Maguire, politicians. I was making $4 to $6 million a year. It was unbelievable. $250,000 buy-in.

    10. SB

      So I couldn't sit down unless I brought $250,000 to lose?

    11. MB

      That's right.

    12. SB

      And you saw someone lose $100 million in a night?

    13. MB

      Yes. This is where the science of how you make people feel became a really big tool, and I would memorize people's lives, the names of their kids, what they cared about, favorite food order, drink order. These things can absolutely be used for good, but I just became obsessed. What had been about trying to be an entrepreneur and be gutsy started to be exclusively about the money and the power, but I paid a huge price for it. I started to partner with people that were not the right people to partner with. In the middle of the night, I get arrested by 17 FBI agents, machine guns. They put me in handcuffs and they put this piece of paper in front of me that says, "The United States of America versus Molly Bloom."

    14. SB

      The FBI gives you an ultimatum. They were gonna give you millions if you snitched on the players in the game.

    15. MB

      I had 48 hours.

    16. SB

      What happens then? Before this episode starts, I have a small favor to ask from you. Two months ago, 74% of people that watch this channel didn't subscribe. We're now down to 69%. My goal is 50%. So if you've ever liked any of the videos we've posted, if you like this channel, can you do me a quick favor and hit the subscribe button? It helps this channel more than you know, and the bigger the channel gets, as you've seen, the bigger the guests get. Thank you and enjoy this episode. (instrumental music plays)

  2. 2:014:55

    The Pressure to Be a High-Achiever

    1. SB

      Molly, what do I need to understand about your earliest context to understand you?

    2. MB

      Going right in. (laughs) Um, I think it almost always starts with the family, uh, and childhood, and I am from, uh, a family of, you know, my two little brothers are incredible humans, but like, the craziest overachievers you could ever imagine. And then I have these two incredible parents who were very powerful influences in our lives. My dad stood on this platform of you cultivate discipline, and if you have a fear, you walk through it, and you learn how to suffer constructively for your dreams, for your goals. And then my mom, uh, you know, she was this... She insisted on kindness and integrity. So there was this whole ecosystem of extraordinary, and I didn't know how I fit into that at all, and I desperately wanted a seat at that table. And probably during the times that w- we were raised, there were these ideas of what success looked like and how you get there, and it was genius and talent and specific skillset, you know? But I knew that I had to be successful or... And this is not hyperbolic. I literally did not wanna live. I mean, I remember when I was applying to law school, I said to my dad, "If I don't get into an Ivy League law school, I don't know, like, ho... I don't wanna live." You know? And-

    3. SB

      Do you mean that?

    4. MB

      It's hard to know what you mean at 18 years old. But, in my mind, you need clear proof and evidence that you are extraordinary by these accomp- accomplishments, and my brothers had already started to make that happen. And I-

    5. SB

      Why law?

    6. MB

      Hmm?

    7. SB

      Why law?

    8. MB

      (laughs) Because one day at the dinner table, my dad said to me, "Do you like to argue and read a lot? Maybe you should go to law school." And then I, and then I started to kind of read books about the law and fiction a lot. I, I mean I was... I loved stories. Um, and- and then started to think about getting paid to argue for a living, and all the glory that could come from that if you're fighting for justice or you are, you know, fighting to save somebody who's innocent. You know, the- the sort of high points, the aspirational points of what it would be like to be a lawyer in a movie or a book.

    9. SB

      You're thinking about the glory?

    10. MB

      Yeah. Yeah. For sure.

  3. 4:556:16

    I Was Chasing Glory

    1. SB

      Why do you think you cared so much about glory?

    2. MB

      I don't think I cultivated much self-esteem. I don't think I knew who I was, and I don't think that I believed I was inherently worthy. I believed that I had to achieve something big, huge, extraordinary, worldly in order to... to then feel relief from that existential ache of... That I've... That- that followed me around my whole life, you know?

    3. SB

      So you- you go off and try and pursue a career in law, at least that's what you think you're gonna do?

    4. MB

      Yeah.

    5. SB

      You were gonna go to Harvard, right?

    6. MB

      Well, I wanted to go to Harvard. I didn't even end up going at all or even finishing my last semester and a half at school because I just couldn't... I couldn't muster the- the energy and ambition it took to go do all these things. I- I just had... I had hit a wall, and I think I was really questioning the conventionality of it all. So I ended up, like, not applying to law schools and then just saying, "I just need a year." And...... the closest place that was warm on the ocean from Colorado in a straight line was California. (laughs)

  4. 6:167:33

    Finding My Way in LA

    1. MB

    2. SB

      When you moved here, um, your father, a- again, bringing him back into the picture, he's a very ambitious person-

    3. MB

      Yes.

    4. SB

      How did he receive this news that you were-

    5. MB

      N-

    6. SB

      ... coming to LA?

    7. MB

      Not happy about it, not gonna financially support it. Really disappointed.

    8. SB

      So you get here and he's, he's no longer supporting you financially at all?

    9. MB

      Mm-hmm.

    10. SB

      So what'd you do to make money?

    11. MB

      I mean, I got a job. I had to get a job th- the day I got here, and I went to this restaurant in Beverly Hills. Went to, uh, you know, got a job for a couple days. It was terrible, and then I went to this other rest- um, I went to this other restaurant and kind of lied and said, 'cause no one else was hiring in this Beverly Hills area, and it was a fine dining establishment, and I lied and said that I had fine dining experience. I got fired a couple weeks later. My boss said, "You're the worst waitress we've ever seen, and you've ruined, like, thousands of dollars of bottles of wine trying to open them." (laughs) He said, "But, you know, people seem to, to take to you and you're a hard worker, so why don't you come work for our real estate development company as my executive assistant?"

  5. 7:3310:01

    Becoming the PA of the Biggest Poker Game Organiser

    1. MB

    2. SB

      Oh, so it was the boss of the restaurant that-

    3. MB

      Yes.

    4. SB

      ... offered you the job as the exec again?

    5. MB

      Yes. They, they had a bunch of holdings. They had some real estate. They had some restaurants.

    6. SB

      Right.

    7. MB

      They had a fund.

    8. SB

      So you became his EA, his PA?

    9. MB

      Yeah.

    10. SB

      And this led you to poker?

    11. MB

      Yes. He came in the office one day and he said... And they're always zany things to... It's sort of, like, thrown at me, and he said, um, "I need you to serve drinks at my poker game tomorrow night." And I, you know, I tell this story 'cause it's just so indicative of, of the naivete and where I was. I, I remember googling, "What kind of music do pic- poker players like to listen to and what do they eat?" And I proceeded to make this incredibly embarrassing playlist with songs like The Gambler on it, you know, and, uh, got this cheese plate, and showed up for this very fancy, uh, poker game in, in Hollywood with A-list celebrities. And, you know, there's some names that, of people that have already talked about being in the games and those are the names that I don't mind naming, just to give context. It was Ben Affleck and Tobey Maguire and Leo DiCaprio. And then, you know, but a- apart from the actors, it was also the head of some of the biggest investment banks in the world and the head of some of the biggest movie studios, and politicians who were household names, and people in the tech world that were about to take their companies public. I mean, it was... It was unbelievable.

    12. SB

      Quite a few people have c- come out, as you say, and said that they were... They played in those games.

    13. MB

      Yeah.

    14. SB

      I was watching a video earlier of, like, even Dan Bilzerian, I think, says-

    15. MB

      Yes. Dan played.

    16. SB

      He played in those games. Was- was- were those games legal or illegal?

    17. MB

      (sighs)

    18. SB

      'Cause-

    19. MB

      Legal to play in.

    20. SB

      Legal to play in.

    21. MB

      For sure. Legal... I- w- when I started running the games, I hired, uh, defense attorneys and had them analyze the federal statutes and to help me figure out a way to do it legally, because in the early days, I wouldn't have done it illegally. That was an evolution.

    22. SB

      So you start as a- basically an assistant to the games-

    23. MB

      Mm-hmm.

    24. SB

      ... that your boss is running. These are secret games,

  6. 10:0112:18

    Entering the Poker World & Its Secrets

    1. SB

      right?

    2. MB

      Right.

    3. SB

      Very secretive.

    4. MB

      Very.

    5. SB

      And take me on the journey of what happens next.

    6. MB

      Okay. So that first game, you know, I'm just shell-shocked, essentially, and also really mortified about the playlist and the cheese plate from Gelson's, you know. Um, but, but man am I intrigued. You know, getting to be a fl- at 23 years old, getting to be a fly on the wall in this room where the- these conversations are open and candid and you are... I'm like you. I've always been fascinated in psychology. I've always been an information data junkie. I love to learn. I love to observe. And so this was as compelling as it could be. And then I remember at the end of the night, because people were tipping with chips, it wasn't straight cash, I remember making $3,000 for refilling some drinks. And so two things became really apparent to me. One, this was incredible access to a network of people that I don't know if I would've ever had access to, and to learn from people at this age of 23 when I didn't know who I was or w- who I wanted to be. And number two, that there was something that happened when there was a token or a chip, was the, was the economic system that made people very liberal. 'Cause I'd worked as a wait- you know, I was, I was waitressing everywhere. I'd hustle my butt off for a couple hundred dollars a night. You know, all of a sudden, the chip is involved and it's not real money. So I just became obsessed and so I learned about poker. I wanted to learn the rules of the game, the vernacular. I, I didn't wanna seem like a novice. Um, and then I started to try to figure out, "How do I stay in this room?" And...This is where, one of the places where effective presence became a really big tool.

  7. 12:1817:41

    The Psychological Strategy Behind Your Success

    1. MB

    2. SB

      What's effective presence?

    3. MB

      Effective presence is the science of how you make people feel. Everybody has their own emotional footprint that they leave on the world, and, um, there are really marked things you can do to have either positive or negative effective presence, or neutral, which is also not great. Um, so I remember talking to my mom, and I remember saying, "You don't even understand how compelling this is," and "I don't, I want to stay in this room more than anything, but I don't know how I could ever (laughs) confer value in this room."

    4. SB

      Did you feel like you were gonna be kicked out of the room?

    5. MB

      I just felt like maybe I was disposable, like maybe they would just bring in an- another woman at some point to serve drinks or, you know, I just, I didn't, I just didn't want to be disposable. I wanted to find some reason to be... to be valuable in that room, to, you know, and- and to be able to come back. And I start, I was talking to my mom so much about everything that I hoped to gain and- and where my mind was going with this opportunity and, you know, then I said to her, "But Momma, I've no idea how to bring value to this room. These people have everything." And she said something that was really profound to me. She said, um, "You know, maybe instead of thinking about all the things you want to get, you could think about what you could give." And then she reminded me of that quote by Maya Angelou that everyone loves and loves to quote, which is, "People are going to forget what you said and what you did, but they're never gonna forget the way you made them feel." And I thought about that, and it's so true. And I guess I had this suspicion that these people with their power and their success and their access were different from the rest of us, that they believed that they were worthy, you know? That they didn't have- harbor that secret fear that they weren't good enough. And what I found, unequivocally, is that that wasn't true, and that many times someone at that level is even more convinced or needs even more validation. And so I started to try to understand how to make people feel important, seen, heard, remembered, how to establish trust, how to establish authentic connection, because something that I realized by observing these games is that everybody wanted something from these people. That was the nature of the relationship. And so if I could figure out how to establish a real connection... You know, there's- there's emotional intelligence, right, which usually has a focus on the outcome, how to win friends and influence people. Effective presence is more about being in the present with someone, focused on the connection, not the outcome. And this is truly what I focused on, um, for the first six to seven months, is just creating a real connection with people, observing them and f- and, you know, trying to train my mind to focus on, "What's unique about this person? What's truly unique about this person?" And then getting to a point where you're vulnerable enough to say, "God, I'm really fascinated by this thing that you do." You know, whether it's at the poker table or in business or just in life and- and focusing in on the details and- and really getting outside of yourself and becoming curious, becoming a great listener, which, by the way, you are an insanely great listener. (laughs)

    6. SB

      Oh, thank you. (laughs)

    7. MB

      Um, and I just have found, probably like you have, that there is such incredible value in that and that no matter how much somebody is celebrated or, um, you know, has- has, uh, a public following or whatever, it's so seldom that someone just sits down with them and listens, just gets in it with them.

    8. SB

      So funny. As you were saying that, I was just thinking about how much of a competitive advantage listening is.

    9. MB

      Yes.

    10. SB

      We think that the competitive advantage is had in speaking.

    11. MB

      Mm-hmm.

    12. SB

      But I've, if I've learned anything from doing this podcast, it's that to truly understand someone and then be able to, in this context, ask them a question, but in-

    13. MB

      Yeah.

    14. SB

      ... the world of business, to deliver them a solution to their problem, which is cl- getting a sale, to create the upper hand, you simply have to listen.

    15. MB

      Yes.

    16. SB

      And you have to listen for as long as you possibly can.

    17. MB

      Yes. (laughs)

    18. SB

      And this is what- what the great thing of what I've learned from doing this podcast but even from this conversation is-

    19. MB

      Mm-hmm.

    20. SB

      ... I'm- I'm... My next question is gonna be so much better for the fact that I listened to you-

    21. MB

      Right, and actively listened.

    22. SB

      ... and s- actively listened.

    23. MB

      Presently listened.

    24. SB

      Yeah.

    25. MB

      I think we walk around armored with our egos, and I think that true connection happens when somebody, when you're able to disarm somebody and they're able to disarm you and the egos slip away and it's just two people. So when you go in and you start listing off your accomplishments and painting yourself as this per-, you know, all of a sudden it's like competition up, ev- egos up, and- and then there's not true connection.

  8. 17:4119:55

    Playing the Manipulation Game

    1. MB

    2. SB

      You can't penetrate-

    3. MB

      No.

    4. SB

      ... that kind of wall, can you?

    5. MB

      No.

    6. SB

      If you've both built two walls between yourselves 'cause you're showing off.

    7. MB

      No. Right.

    8. SB

      You need the walls to come down-

    9. MB

      Right.

    10. SB

      ... to form the connection.

    11. MB

      Yeah.

    12. SB

      When people hear that, they go, you know, this- this idea of effective presence and understanding how to be kind of a different jigsaw-shaped piece to each individual to get the best out of them or what you want from them, people will say, "Oh, manipulation."

    13. MB

      Mm-hmm.

    14. SB

      Which, you know, the- the fine line between sales and persuasion-

    15. MB

      Mm-hmm.

    16. SB

      ... and negotiation and manipulation, it's all there.

    17. MB

      Mm-hmm.

    18. SB

      You know? Is this positive manipulation?

    19. MB

      So-Effective presence, EQ, active listening, all of these things that you learn can absolutely be used for good or they can be used for bad. But I think something that is different about at least the brand of effective presence that I value is it's about your experience connecting with a human being. It's not about form- 'cause I used to do that, right? I used to... The, the way I used to do things is I would do all my research on you and I'd come in here with a few, with a few talking points so that I could instantly connect on something with you and show you that you and I are, are the same. And I... I don't really do that anymore, although I don't hate that strategy. Um, but I think it just depends on how you use it. I think when you use it in a manipulative way, I think it's easier to see versus if you kind of take a few breaths before you go into a room and you say, "This mo-... What I wanna do here is to connect with someone, to have that human-to-human feeling, and, you know, to, to be of service in some way to a, a... in a greater way to humanity." And by the way, that can also include yourself, (laughs) you know.

    20. NA

      Mm-hmm.

    21. MB

      But I think it's about disconnecting from the outcome, disconnecting from the transaction, and connecting as a human being.

  9. 19:5524:47

    Running the World's Most Exclusive Poker Nights

    1. MB

    2. NA

      So how'd you get from being the waitress in these rooms serving drinks to running your own poker nights?

    3. MB

      This is a funny story. Okay, so couple months go by, right? And I'm like, "I don't wanna serve drinks in these rooms. I wanna, I wanna start my own games. I wanna own these rooms." You know, this was someone who felt powerless in the world. If I could control these nine seats, you know, this thing that has so much control over these people that are so powerful, that was compelling. The money was compelling. I had this whole idea of how I would design the experience. That was compelling. Um, and also, you know, I'd sort of learned in those six to eight months that, that I was an entrepreneur. I was a problem-solver. I could, I could think on my feet. I had metacognition. I could feel a certain way inside, terrified, nervous, scared, and still act with composure. These things that wouldn't quite present at a dinner table growing up with Jordan and Jeremy Bloom to culminate into an idea or, uh, you know, sort of like that seat. All of a sudden, I just started to feel in my flow, you know? And so... But I was very loyal to my boss, and he is an interesting character. He was slightly psychopathic. Uh, so I, I, you know, I just bided my time and I tried to figure out how I was gonna do this, and, and then he made it quite simple for me because he called me and he said, "You're focused too much on the game. I need you back in the office. I'm giving the game to someone else. Her name is da, da, da, da, da. She's gonna be calling you." And by this point, I had really kind of gotten into, like I had started to think about how I was gonna build this game. I had- I was keeping, um, the books on everyone. I was, uh, recruiting players. Uh, you know, I, I, I really had... I was doing much more than just waitressing, and I thought about it and I was like, "I gotta take my shot. I can't just go. I can't just let him take this. Like this is, this opportunity is too important for me." So I had developed friendships and alliances, and so I planned a game, and I moved it to a really luxurious location, and I hired a full staff of people and had them memorize everyone's favorite food order, drink order, uh, the names of their kids, what they cared about in life. Upgraded my playlist to a little Frank Sinatra maybe. I don't remember what it was, but it was better. Moved it out of this dingy basement, had it catered by, you know, the, the best restaurants in town, up, uh, you know, like the best liquors, Cuban cigars. I mean, I wanted people to walk into this room and feel like they were in Monaco or feel like they were James Bond for the night. And I, I really, as the games wore on, I, I really, like, got into the science of scent science, and temperature, and humidity, and, um, food, and all these things that elicit the feel-good chemicals. And so... And then I invited everyone except for my boss. (laughs)

    4. NA

      (laughs)

    5. MB

      And at the end of the night, it- the game went really late, and then at 5:00 in the morning, I got this text message from my boss and he said, "Get over here." Uh, to this day, I don't know why I went. I just went. And he made me go wait in this, like, bedroom, and he made me wait for a long time, and I, I, I thought, I said to myself, "He's gonna (laughs) kill me." I mean, I don't even know what's gonna happen right now 'cause he was a, was a terrifying individual and very powerful. And just to give you some context, when I started working for him, I used to always say to him, "I'm really worried about your soul." (laughs) Like, "You're not a nice person," you know? And, and I saw him in a business context. And then later when I got to know him better, I saw him with his family and he was very kind. But he used to say to me all the time-... you, you're gonna, you're gonna get trampled over. Like, you need to toughen up." And so, anyway, so he walks into the room and he has this terrifying look on his face and he looks at me and he goes, "I'm proud of you." It was like graduation day, for better or worse, you know. It's hard to know how to feel about that moment now, sitting here decades later.

  10. 24:4728:54

    He Wanted My Money Or Would Take My Poker Nights from Me

    1. MB

    2. SB

      So from that moment when you host that first game, you upgrade everything, you upgrade the experience for your customers.

    3. MB

      Mm-hmm.

    4. SB

      Um, eventually you set your sights on New York, but for a variety of different reasons, and you move the games from being based in California, in LA, to being based in New York City.

    5. MB

      I lost the LA game.

    6. SB

      You lost it?

    7. MB

      Yes.

    8. SB

      Someone took it from you?

    9. MB

      Yes.

    10. SB

      Hmm. Karma. (laughs)

    11. MB

      (laughs) Totally. Not gonna argue with that.

    12. SB

      Who, who took it from you?

    13. MB

      Uh, one of the most famous movie stars in the game.

    14. SB

      Leonardo DiCaprio? (laughs)

    15. MB

      (laughs) No.

    16. SB

      Uh, someone took the games from you, a movie star, said, "I'm gonna go do it at my house."

    17. MB

      Gave me an option first. Um, "You can either start making less money..." So, this is very interesting. There was this player in the game-

    18. SB

      Who you can't name.

    19. MB

      ... I, I won't name.

    20. SB

      Mm-hmm. But they're a big male f- movie star?

    21. MB

      Making so much money.

    22. SB

      Okay. How much money are we talking? Like, hundreds of millions?

    23. MB

      Yeah.

    24. SB

      Okay.

    25. MB

      But became, I would say, pathologically obsessed with this game and structuring the game so that he could win all the time. So, making sure that he was the best player in the game and that there were no other, uh, there was no one better than he was.

    26. SB

      Dan Bilzerian said that he was kicked out of the game because he was really good.

    27. MB

      Oh, well-

    28. SB

      And you started calling him back.

    29. MB

      ... listen. I, uh, Dan showed up playing this kind of ruse that he was just this clueless trust fund kid, okay? And people bought it. And I sat, I sat there watching him and I'm like, "This dude knows what he's doing." You know? And I, and I said, "Respect," right? Like, "You're hustling, I'm hustling, but you can't play in this game. You're gonna take everyone's money. You're bad for business."

    30. SB

      So-

  11. 28:5431:42

    Do You Resent Him?

    1. MB

    2. SB

      Why, what was he bringing to the table where you couldn't just kick him out? Was he bringing a lot of influence-

    3. MB

      Celebrity power, yeah.

    4. SB

      ... and celebrity power.

    5. MB

      Yeah. This, in this town?

    6. SB

      So, he, he was, he basically said to you, "Listen, you're making a lot of money. I'm, I'm bringing a lot to the table 'cause I'm bringing celebrities and contacts and legitimacy to this, so I'll put a cap on your earnings and I get the rest of what you're making, but I'll continue to do my part."

    7. MB

      Yes.

    8. SB

      So he kinda wanted to make you his employee?

    9. MB

      Right.

    10. SB

      How'd you feel about that?

    11. MB

      I never wanna be anyone's employee ever again.

    12. SB

      But how'd you feel about him?

    13. MB

      I-

    14. SB

      'Cause when you said it, you looked a bit pissed off, to be honest.

    15. MB

      Uh, (laughs) did I?

    16. SB

      A little bit. You looked a bit like there was still a little bit of maybe resentment to that moment.

    17. MB

      You know, I think that there's just conviction to that moment.

    18. SB

      Right.

    19. MB

      Of... 'Cause I think we live, uh, i- in a day and age where a lot of people try to, um... Not in a day and age, we, it's, it's reality that a lot of people, um, try to misuse power and I think it's really important to talk about, you know, sort of dignity in the face of that and, and, and turning the offers down. (laughs)

    20. SB

      So you said no. What happens then?

    21. MB

      Called me about a week later and with this almost jubilant laugh and tone was like, "Don't, you're done."

    22. SB

      How could he ensure that you were done?

    23. MB

      He had colluded with the biggest whale in the game. A whale in a gambling co- context, someone with a lot of money who's not very good, who's willing to lose a lot of money.... and this person had endless funds, and he had colluded with him to have the game at his house, and that was where the money was for everyone. And you asked me a question, how do I feel about this person? Um, here's my answer. This was a really long time ago. Um, and I've totally forgiven him.

    24. SB

      So you lose the game?

    25. MB

      I lose the game. I was devastated.

    26. SB

      W- what's going through your mind at that moment?

    27. MB

      I'm done. I'm never gonna be able to make this much money again. I'm never gonna be ... I'm gonna have to go join some, you know, I'm gonna have to go work for someone else. I'm not gonna be able to be my own boss. I'm not gonna live in this fascinating, adventurous underworld where I get to, you know, pull the strings and move the chess pieces, and, and, and I have to go join the real world, where I'm not extraordinary. (laughs) You know, I'm just telling you what's going through my mind. Now when I say these things, it's like, it is what it is,

  12. 31:4236:18

    Taking Over the Poker Scene in NY

    1. MB

      but ...

    2. SB

      So you eventually moved to New York?

    3. MB

      Yes.

    4. SB

      Um, 30 years old at this point?

    5. MB

      I'm 31 at that point.

    6. SB

      Okay.

    7. MB

      Yeah. Um, so, you know, I, I bet ... My parents said, "This is a great time for you to go back to school. You've saved all this money. You've learned all this, you know, you've gained all this information. You have this incredible network." And I said to them, "You're absolutely right, but I have something that I need to prove, to myself at least." Because the plan was never to run poker games for the rest of my life. I don't think that's something that's sustainable. The lifestyle was not conducive for raising a family. Um, late nights, cr- you know, crazy adrenaline. It was not something that I could imagine myself doing for the rest of my life. I knew I needed to walk away at some point. I knew I needed to parlay it into something that was less underground, less gray. But, you know, I have to tell you, there was something very thrilling about it. Um, but then I got angry and I had something to prove, and there was just nothing that was gonna stop me.

    8. SB

      What made you angry?

    9. MB

      Feeling like I had been disposed of so effortlessly. Something that I, you know, something stolen from me that I had c- curated and built and, you know, (laughs) you said karma before, and, and there is some truth to that. But I did everything justly, you know? I left money on the, my own money on the table to curate this incredible experience. Um, I, I ran the games with ultimate integrity. You know, I, I wasn't unkind to anybody. I just felt it was really unfair. And so also, I was embarrassed, you know? So, I decided I was gonna build the biggest poker game in the world, like 5 times, 10 times bigger than the game in LA, and then I would go away. And I decided after doing some research that I would do it in New York City 'cause it seemed like there are a lot of gamblers on Wall Street. There were many problems with my plan. First of all, I didn't really know anyone in New York City. It's ... That sort of like billionaire Wall Street world is not so easy to penetrate. Um, secondly, it was 2008, so the economy and Wall Street had just been brought to its knees in the most profound way since probably the Depression. And thirdly, there were some pretty scary characters running games in, in New York who'd been doing it for 20 years. But, you know, it's, it's testament to when, when the, you're obsessed with something, when, when the end, like you'll do anything, unfettered ambition, you'll do anything to get there. Things are possible, for better or worse. So, you know, I made moves, and I did research, and I interviewed poker players, and I found out who the right people were to talk to, and I found out what was wrong with the current system, what was wrong with the current games and, and where I could improve on that. I already knew I could, I already knew I could bring the branding and the experience, which was meaningful. It truly was meaningful. Um, but what I found is in these big games, in these New York games, a lot of the game runners were kind of running a Ponzi scheme. If they didn't get paid, they wouldn't pay out. They were playing in their own games, whether they were winning or losing would dictate the rake of that night, and the rake is the illegal tax that most of the game runners were taking. And so it was a matter of treating people fairly. It was a matter of being trustworthy and consistent and, um, having integrity. And, and then I ... And, you know, the biggest thing I could do to instill that trust and to have integrity and to eradicate the fear was to become the bank. I would now, MDB Inc. would now become the bank, guarantee the games, pay if there was, um, if somebody stiffed, I would

  13. 36:1842:41

    Someone Lost $100 Million, & It All Started a Bad Spiral...

    1. MB

      pay.

    2. SB

      What does stiffed mean?

    3. MB

      Meaning they lost money in the game and then didn't pay the debt.

    4. SB

      Okay. I don't understand that. Surely to get the chips, they have to pay th- for them upfront.

    5. MB

      No. When you run a weekly game, ultimately you establish a credit relationship with someone.

    6. SB

      Okay. Right.

    7. MB

      Um, because-... otherwise, like, these people would have to bring five million dollars in cash to, every week. It's just not reasonable. It's not feasible.

    8. SB

      So tell me about the peak of your New York games, then.

    9. MB

      Yeah.

    10. SB

      So, when you're at the peak, what does that look like?

    11. MB

      So I started this big game. (sighs) It was a-

    12. SB

      Called?

    13. MB

      They were always just called Molly's Game.

    14. SB

      Okay.

    15. MB

      Yeah. Um, so it was a $250,000 buy-in and then this was the game that someone would ultimately end up losing $100 million in one night in.

    16. SB

      Say that again.

    17. MB

      (laughs) Someone-

    18. SB

      Explain, explain all of this to me like I'm a chimpanzee from that documentary-

    19. MB

      Okay. All right.

    20. SB

      ... you were talking about before we started recording.

    21. MB

      So, when you sit down to play at a poker game, there are a couple n- numbers that matter. What's the buy-in? My LA game, the buy-in to sit down, and get chips, and get a chair was $50,000. It started out as 10, I raised it to 50. The New York game was $250,000.

    22. SB

      So I couldn't sit down unless I brought $250,000-

    23. MB

      That's right.

    24. SB

      ... to lose.

    25. MB

      That's right. Then the other relevant numbers are what are the blinds, meaning what do you have to bet, um, each round to, to, to, to play the game?

    26. SB

      To st- at the start of the rounds, you mean?

    27. MB

      Yeah, and there's a small blind and a big blind and it just goes around the table.

    28. SB

      Yeah.

    29. MB

      And- and so these games played so big, there was so much action, the blinds were so high, that, you know, that initial buy-in would be gone with some people in the first 20 minutes. So then they'd have to come to me and say, "I need another 250." And I would have to decide in that moment, can they pay this? Are they good for the money? Um, and so I would have to est- start to establish this relationship, this financial relationship with people, based on trust a lot of times. But there were a couple things that ke- that kept me safe. Number one, to stiff this game was social, reputational suicide. People would start to say, "Oh, they don't have money anymore." Number two, there wasn't a game like it where you could play with some of your biggest heroes. I mean, there was so much business that got done at these games. The things that I saw created, you know, it was mind-blowing. But also-

    30. SB

      And you couldn't just go to the police if they stiffed you, right?

  14. 42:4144:37

    I Compromised My Integrity

    1. MB

      not- I don't have judgments. Whether or not, like, you know, the... Sports betting just became legal. Sports betting, so many people in my indictment got indicted for sports betting. Now it's legal. Now if you live in New York or New Jersey, you can download an app, connect it to your bank account, watch a tennis game. Pretty much everything that happens in that game is a bettable moment. You can also do that with a Charles Schwab account. I harbor no judgment for DraftKings, whoever the companies are, the CEOs are. It matters who you are, right? For me, once I realized that what I was doing was using all my resources, all my skills, all my intelligence to do s- to, to push an activity that was ruining a lot of people's lives, that was a insult to my integrity. That, that was getting out of alignment with who I am and what I care about in the world.

    2. SB

      What were you good at? So at that peak moment, when you do a skills audit of why you were successful-

    3. MB

      Mm-hmm.

    4. SB

      ... what appears on that skills audit?

    5. MB

      Very good at strategy. Seeing a problem, coming up with a solution. Setting a goal that has, you know, most of the time, pretty slight odds figuring out how to get there. So I'd become very good at strategy. I'd become, um, really good with people. I became so good at it that I became manipulative, and I was using those skills to manipulate people for my personal gain, period. It's not a win-win.

  15. 44:3748:14

    The Downfall: The Crashing Impact on My Health & Relationships

    1. SB

      And all of these things, the, the lifestyle that you'd chosen to live and the way you'd chosen to live it, you speak of the internal conflict this creates.

    2. MB

      Yeah.

    3. SB

      Right?

    4. MB

      Mm-hmm.

    5. SB

      Um, were you depressed at that point in your life? How was, if I was a fly on the wall when you were going home, what would I have seen? What would I, you know, if, if I was a fly on the wall that could feel what you're feeling, what would I have felt and what would I have seen?

    6. MB

      I was very depressed, very disappointed with myself. Um, and completely powerless over these forces. Money. At the, by this point, drugs. And when I say drugs, like I wasn't, I didn't like the inconsistency and the unreliability of street drugs. I liked the f- the consistency and formulation of, of, um, pharmaceuticals. They allowed me to be productive and not feel myself, not feel the world. Um, I was drinking a lot.

    7. SB

      Why didn't you wanna feel the world? What were you escaping from?

    8. MB

      Myself, what I was doing, the, the way that I was living.

    9. SB

      What was it you were so ashamed of about the way that you were living outside of the games?

    10. MB

      I had stopped really communicating, b- showing up for my family. At times, didn't treat people that worked for me a- as well as I'd like to. I started to have... you know, New York was a, was a trip. I had all these beautiful, interesting, compelling women that worked for me, and although I always wanted them, I always wanted to mentor them and, and provide them with opportunity, the truth is is that I j- made sure they made enough money so they stayed in that darkness with me. And I didn't hold myself to the same accountability that I would hold myself now to in a friendship. I pay them so much money, I don't have to show up for their birthday, right? It was a, it, I had, even if I didn't act like it, in my mind there was a hierarchy. So I had no authentic relationships, or very few. Um, those were the reasons.

    11. SB

      Were you in a relationship at this point?

    12. MB

      So I was in a relationship for most of the LA game, and that ended right around the same time that my game ended. And then I went to New York and had sort of a secret relationship. One of the big players' little brother, who kind of did my role in the beginning of handing out chips and everything, I found to be this deeply fascinating, brilliant, heart-centered person. And so we were in this secret rela- relationship, but I didn't want anyone to know 'cause he was... He didn't measure up to the, the persona that I was trying to sell, which was very hurtful to him.

    13. SB

      How did he know?

    14. MB

      I told him, "We can't tell anyone."

    15. SB

      Did you tell him why you can't tell anybody?

    16. MB

      I said, "It's bad for business."

    17. SB

      Is that what hurt him? You just saying it was bad for business? 'Cause if you said that to me and we were in a relationship, I'd think, okay, you, okay, you don't wanna com- uh, complicate the dynamics. You don't want some people to know that someone you're in- you're involved with romantically is also kind of attached to the game, so...

    18. MB

      Yeah, I mean, I think in the beginning it made sense, right? But down the road, I think it became very clear.

  16. 48:1454:53

    The Italian Mafia Put a Gun in My Mouth

    1. MB

      And we, we had conversations about it.

    2. SB

      Hmm. Some point, the, the mafia show up.

    3. MB

      Yeah. So here's the kind of, uh, levels and stages of the, the train wreck. So the first thing that happened was I r- I had just recruited these guys. They were Russian-American businessmen. They had the air of being Ivy League, seemed so legitimate. I had people vetted within an inch of their life. I used to hire the same people that vet politicians, for instance.To vet people. I had bank employees on my payroll to find out people's liquidity. I mean, it was a whole process, you know. It's a lot of money and big risk to bring some- a stranger into a room with important people. And their stories checked out, but there was something in my gut that told me it was off. And it turns out that they were running the biggest insurance fraud scheme in New York City history and they had alleged ties to the Russian mob. So then the feds start to pay attention to this $100 million poker game where people can show up with millions of dollars in cash and get a check, right? Pretty rife for, uh, corruption. Um, and interesting for them. The next thing that happened was I had a- yeah, I had a run-in with Italian organized crime. And I- I guess naively I thought that- I knew that gambling was always one of the ways that organized crime earns, but, you know, I was having the games at the Plaza Hotel with billionaires and players for the New York Yankees and I- I just believed that there was enough separation. But by this time, I had become the biggest game runner in New York City and they didn't care. They didn't care who my clients were. And they were really clear with me, uh, "You know, if you wanna continue to run these games, you're gonna have to give us a piece." And we all know... We've all seen that movie, right? And I tried to polite- I politely declined their offer and tried to explain to them in business terms why that wouldn't work for me and- and just went on my merry way and started to avoid their calls. And, uh, they didn't just go away and they sent this terrifying guy to my apartment and he put a gun in my mouth, which is something that you just never forget. And he beat the hell out of me and, um, took everything that was in my safe, including photographs, the- you know, couple things I had from my grandmother. And, you know, he said, "I think your answer will be different next time. And if you tell anyone about this, I know where your family lives in- in Colorado." And so a couple things here. First of all, if somebody comes into your apartment in the r- you know, in the real world, in real life, and puts a gun in your mouth and steals things from you and beats you up, cracks your ribs, you have somewhere to go. You call the police, you call your family, you call your friends. It was undeniable now that what I was doing was so deeply dangerous and underground and I was completely alone in it. I- I was too afraid to- to tell anyone. And so I'm trying to, like- and also, now I'm not just putting my own life in danger, right? Like I'm in, in way over my head and my family's at danger- in danger now. And I'm just... I mean, it is so heavy and so much. And for the first time in my life, I don't have any strategy. I don't... I have no idea what I'm gonna do. And then I got so lucky. Uh, you know, my only contact with the outside world was food delivery, um, and- and then- and The New York Times. And a couple days later, I got The New York Times and it said, "125 arrested in the biggest mob-related takedown in New York City history." And I never heard from them again. But, you know, disaster is a-comin'. (laughs) It's just... And the- the last thing that happened before the whole thing blows up was, um, you know, for most of my poker running career, I was- I was running these games legally, according to this playbook that had been written for me by- by my attorneys. And one of the biggest ones that differentiated me from a lot of the games in the city and LA was that I didn't take a rake. I didn't take a- a percentage of each pot. At the end of the game, you- winners tip, you know. I'm extending people millions of dollars. I'm in charge of the nine seats that people are- a lot of them are pathologically addicted to. At the end of the night, I- I got paid a lot of money. I was making four to $6 million a year. And, um-

    4. SB

      Just from tips?

    5. MB

      Yeah.

    6. SB

      So where- so where did that four to $6 million a year come from? From-

    7. MB

      The winners. So the winners would play in the game and if they won, you know, they would tip a percentage, 1 to 5% of their wins. Games were huge. And I was running multiple games around the city, paying my taxes. I have an event planning company. But, you know, I was a mess and I started to get reckless about who I was letting in the games and- and- and who I was letting play and my debt sheet started to get bigger and I started to take a rake. I started to partner with some people that, you know, were not necessarily the right people to partner with. And, um, and the- the feds had thrown a confidential informant in the games by that point, and he tracked that. And so around the end of that year, I got a text message from one of my employees at one of my games and they said, "The FBI's here looking for you. Don't come here." And so, um, you know, I- I knew finally it was game over.

  17. 54:5358:25

    The Terrifying Moment When the FBI Came After Me

    1. SB

      It was game over.

    2. MB

      Mm-hmm.

    3. SB

      And you realized that when you got that call saying, "The FBI are here-

    4. MB

      Yeah.

    5. SB

      ... looking for you."

    6. MB

      Yeah.

    7. SB

      How'd you feel at that moment when you hear ... Someone calls me and says, "The FBI are looking for me"?

    8. MB

      Terrified. I want my mom and I want my dad, and I wanna go back in time. I don't wanna do any of this. Don't even know how to process this. And then, couple of hours later, it got even worse. I got, um, you know, I went back to my apartment and the whole time, I mean, it's like you're in a movie, you're, uh, looking around every corner, is, are they gonna be there to apprehend me? And, um, I packed a bag and grabbed my dog and, you know, tried to book a plane ticket to, uh, Denver from JFK. And my credit card got declined, which was strange, and then my debit card got declined, which was really strange. And I logged into my accounts and the account balance read -$9,999,099 in all of my accounts.

    9. SB

      Why?

    10. MB

      Because the feds had seized every single penny, and then some.

    11. SB

      So what happens then? Did you manage to get outta New York?

    12. MB

      I did. I managed to get outta New York, I got home to Colorado. I'm at my mom's house. My attorneys are talking to the feds and they said, basically, in, in this country, you, as a person, have the presumption of innocence, but your property does not. So someone can't just come get you unless it was under some of those, like, after 9/11 or whatever, but-

    13. SB

      Mm-hmm.

    14. MB

      ... you know, let, let, let's just keep it simple. Someone can't, can't just get you, throw you into jail, say that you're guilty. You have the right to a trial. With your money, with your property, it's different. There's a division of the government called Asset Forfeiture that can just take it, and then you have to go into legal proceedings to try to get it back. And so basically what that would involve is me going on record, talking about this game and telling how I made this money, which, for the most part, I'd made it legally, but, you know, the past several months, I hadn't, and it would be an admission on record of a crime. So I couldn't, I couldn't do that. And at this point, they said, well, she, we're not interested in her as, you know, we're, we're not pursuing anything criminally against her and, and if we are, we'll let her know. So I just went ... I just (sighs) I just went home.

    15. SB

      What do your parents think of you when you come home at this point?

    16. MB

      I don't even know what they think of me. I think they're extremely worried. I think that my dad had been writing me handwritten letters every year telling me that what I was doing was going to end badly, pleading with me to do something different. Um, so I think my dad was angry. Um, my mom's just scared. And I think they're also relieved, right? Like, they were s- you know, they knew that what I was doing was dangerous. They knew it was, I was up late at night running around with large sums of cash. I mean, they had many sleepless nights.

  18. 58:251:03:00

    Facing 10 Years in Prison

    1. SB

      At some point, the FBI gives you an ultimatum regarding becoming a snitch.

    2. MB

      Oh, okay. So, it took two years. For those two years, I moved in with my mom, I got sober. I-

    3. SB

      At 35 years old?

    4. MB

      No. I'm not 35 yet. I'm ...

    5. SB

      33.

    6. MB

      33. Um, got sober. Trekked to Machu Picchu, did some soul, deep soul searching, um, finally got a job, moved back to Los Angeles. Seven days later, this is two years later, okay? I don't think anything's coming. I have rehabilitated (laughs) myself, you know, and I'd been living with my mom and my grandma in the mountains of Colorado. (sighs) So I move back to LA. Seven days later, in the middle of the night, I get arrested by 17 FBI agents, machine guns, high beam flashlights. They put me in handcuffs and they put this piece of paper in front of me that says, "The United States of America versus Molly Bloom." I'm thrown into this wild indictment. I'm looking at real time in prison.

    7. SB

      How much?

    8. MB

      The press release said 90 years. I think, realistically, it was more like 10. Um, but, um, you know, I have a day and a half to get to New York City to find an attorney that's gonna represent me in the fight of my life and I don't have a dollar. My dad and I aren't speaking.

    9. SB

      Why?

    10. MB

      Because he got mad at me and I got mad at him. (laughs) Because the, the age-old unexplored resentments and rife, you know, came to a head. This is my biggest fear, right? Failing this spectacularly in front of the world. The tabloids are covering it. So, I had a day and a half to get to New York City to find an attorney and, you know, I don't have a dollar. My mom just put her house up to bail me outta jail. My dad's, and I aren't speaking. So, my best friend, you know, loaned me a little money, but I'm sitting down with people who are quoting three to $6 million. And 250 to even look at it. And so I have, uh, like, eight meetings that day before the ind- indictment, or before the arraignment. And seven out of the eight-... all said, you know, "Maya, I really wish you the best but without a retainer, I can't represent you." And then I met Jim Walden, who, uh, was at a very prestigious law firm and kinda, like, listened to my story, looked at my mom (laughs) and said, "I'm gonna help you." And Jim and I started working together and I'll never forget something he said to me. You know, I went in and I said, "Look, I don't have the money to fight this, so ... but I can't do 10 years, you know, and I, I, I have to have a life after this, so what is our strategy and what is our angle?" And he said, "You know what? Integrity is gonna be our strategy and our angle." And I'm just sitting across from Jim Walden who is nothing but integrity, who is this attorney who has spent his life fighting the good fight, who continues to fight the good fight, who spent the first part of his career in the Eastern District of New York fearlessly going after the five crime families, who's looking at my indictment and saying, "This is bullshit." Right? And, um, and taking on this case and, and fighting for me because no one else would. And he's talking about integrity, and I just had this moment of like ... it all hit me, you know? Who I wanted to be, h- how far I had come from that and for what, and, uh, I made a decision in that room that day that I could never ever abandon myself again in that way. I could never abandon the things that I knew to be true to my, to who I am. And, and one of those is, is, is integrity and doing what I believe to be the right thing. And, you know, a couple weeks later, the prosecutors wanted a meeting and they really wanted me to be a confidential informant.

    11. SB

      Snitch?

    12. MB

      Yeah. And, you know, Jim believes this is the whole reason that they brought the indictment.

  19. 1:03:001:08:44

    They Offered to Give Me Money if I Snitched

    1. MB

    2. SB

      So that you would snitch on the players in the game and-

    3. MB

      Yeah. And they didn't care about the mobsters or the people running the insurance fraud scheme. I think they already had what they needed on those. They cared about inside information that I could potentially provide them with on the billionaires, the bankers, the celebrities, the politicians. And I, you know, you spend enough time with people, you do get that inside information. Now, I wanna be really clear about something. If there was someone in my game that was doing really ba- like if Epstein was in my game and I knew that he was trafficking children or whatever (laughs) , like, I would have given that information freely and before this. But what I knew ...

    4. SB

      Was Epstein in your games?

    5. MB

      No.

    6. SB

      Is that not who it was? (laughs)

    7. MB

      No, no, no. I'm saying if there was-

    8. SB

      If there was Epste-

    9. MB

      ... a character like-

    10. SB

      I got you.

    11. MB

      ... him.

    12. SB

      Fine.

    13. MB

      Right? I would have never protected someone like him.

    14. SB

      Mm-hmm.

    15. MB

      But the things that they were interested in, to me, who's booking sports? It's about to become legal in two areas in New York and New Jersey. You're gonna drag somebody's family through the mud and I'm gonna be the, you know, your, your, your accomplice with that?

    16. SB

      Did they offer to restore your bank accounts if you snitched?

    17. MB

      They offered to give me all my money back.

    18. SB

      Which was how much money?

    19. MB

      Millions.

    20. SB

      So they were gonna give you millions if you snitched?

    21. MB

      Yeah. And also they were gonna give me a deferred prosecution which would have kept, you know, sort of given me a guarantee that I would stay outta jail. And I went home and I, you know, I had a very short amount of time to, to make this choice, something like 48 hours, and here's where I got to with it. This place that I was in was a 100% my fault. Like, I did all of this. I had near perfect information about the law, I had great parents, I had college education almost completed. I had all the opportunities in the world, and I had chosen this and I had chosen this path. And I had to own that, you know? And turning around and ruining the lives of people who had played in my game, who'd made me very wealthy, many of them I saw their kids grow up, to get out of the trouble of my own choices did not feel in alignment with my true self.

    22. SB

      So you ultimately get sentenced?

    23. MB

      I get sentenced. I get a judge that's very disappointed with me and, um, but ultimately a pretty reasonable guy who said, "Listen, you were running poker games and it seems like you've done a lot to change your life. I'm not, I'm not gonna sentence you to prison." Which it's hard to adequately express to you how big that moment is because you can do all ... You know, I, I used to say to Jim all the time, "Whatever! I'll go to federal prison, I'll learn a new language, I'll mentor some women." And he's like, "That's not what it's like in the prison system." You know? People are dangerous and a lot of the guards are dangerous and women get raped. It's not, it's not a country club. And in my mind, I was just like, "I can handle it, I can handle it, I can handle it." But in that moment when you get sentenced to not go to prison and you're not, you're not gonna lose your freedom, um, you don't realize how big it is until that happens. You know? And probably would have been even bigger if it went the other way, but, I mean, I felt like (exhales) I, I'm in a... I lost my feet, you know? And, oh, man, you know, here, here we are going to dinner after the sentencing and there's my best friend Allie who stuck with me through everything and my family and even my old boss came. And I'm looking around the table and everyone's living their lives, having kids. My brother has a heart sur- he's in residency.He just graduated Harvard. My other brother just got inducted into Colorado Sports Hall of Fame. And I'm just sitting there and I'm like, "Here I am, the family felon." You know, I'm 30, now I'm 35 years old. Millions of dollars in debt. A convicted felon. A social pariah to some degree. Like, I'm all in for, for a comeback, but how does that even happen? Where do you go from here? So, I just remember going back and walking the mountains, you know? Going back, moving in with my mom, walking the mountains, walking, meditating, trying to figure out what is the way out here.

    24. SB

      You know, one of the things I always, I always talk to my friends about is as you become more and more successful, you get to see behind other curtains.

    25. MB

      Mm-hmm.

    26. SB

      I call it, you know, it's like a-

    27. MB

      Totally.

    28. SB

      ... yeah, like you, it's a curtain that you didn't even know was there and you meet this other group of people and you find out that they're making money in this other-

    29. MB

      Yeah.

    30. SB

      ... set of ways. And you go, "What the fuck?"

  20. 1:08:441:11:55

    What Did You Learn from This Experience?

    1. MB

      like extraordinary people, and that's not what I saw for the most part. There are exceptions. Um, I just saw people who were kind of like unwilling to fail. Um-

    2. SB

      Because?

    3. MB

      I don't know, 'cause they're obsessed with money. Uh, I mean, you know, it was just drive a lot of, a lot of times.

    4. SB

      Or being dragged.

    5. MB

      Or being dragged, right.

    6. SB

      Was it more being dragged than drive? Or was it more drive than dragged? I.e. could they, could they stop if they wanted? You know, could they, were they in control of their obsessions?

    7. MB

      Dragged in that, in those settings.

    8. SB

      Hmm. That's what I've tend to, tend to find.

    9. MB

      Yeah.

    10. SB

      I met a lot of billionaires and I, with the odd exception, I'm like, "Damn, unhappy."

    11. MB

      Yeah.

    12. SB

      They can't stop.

    13. MB

      Yeah. Do you, have you ever read that book The Psychology of Money?

    14. SB

      Yeah, yeah.

    15. MB

      Don't you love that story in there?

    16. SB

      I love it. Um, I don't know what st- story in particular you're talking about, but...

    17. MB

      Don- remember when, uh, Joseph Heller's at the house of the, of the, uh, billionaire? And someone walks up and says, "Heller, like this guy just made in one day what your gross sales were for Catch 22 or whatever." And Heller just goes, "Yeah, but I have something he'll never have." He goes, "What could that possibly be?" "Enough." Boom.

    18. SB

      Hmm.

    19. MB

      That's peace. Most of these people that I knew do not have peace. And peace should not be underrated. Peace, contentment, the ability to find joy in small moments. And then have the big moments. I am all for adrenaline. I still chase it. I have to chase it less now that I'm a mom. (laughs)

    20. SB

      (laughs)

    21. MB

      But I chase it in healthier ways, you know? Heli-skiing, whatever it is, climbing mountains. Um, but to sit, lay your head down at the end of the day and be able to say, "I know who I am." And there may be times where I lose sight of that, but I have a process for that. And, you know, I've made these living amends to these people I love so much.

    22. SB

      What else did you see behind that curtain?

    23. MB

      Um-

    24. SB

      So you saw a lot of dissatisfaction with life?

    25. MB

      Yeah. Um, I saw a much bigger world than I knew existed. And a much more malleable world.

    26. SB

      That's super key, that, that malleability point.

    27. MB

      Yeah, yeah. I thought like the walls were a lot more solid.

    28. SB

      In life, generally?

    29. MB

      Yeah.

    30. SB

      But you realize success is something that we can all bend, control, manipulate?

  21. 1:11:551:20:37

    How My Story Became a Hollywood Success

    1. MB

      thought.

    2. SB

      Is that because you see very ordinary people achieving very extraordinary results and you, and then once you see how they're doing it, you go, "Oh, okay"?

    3. MB

      Yes. Precisely.

    4. SB

      Hmm. That's also what I feel.

    5. MB

      Yeah.

    6. SB

      You know?

    7. MB

      That's cool. I've, I haven't thought about that and that's really cool. I like that. And this next, the way that my story ends really kind of speaks to that. Um, or not ends, but you know-

    8. SB

      (laughs) That chapter.

    9. MB

      ... begins again. (laughs)

    10. SB

      Yeah.

    11. MB

      Um, so I'm walking around the mountains, I'm thinking to myself like, "What's the way out?" And I just realize, there's a unique story here. We've seen this version of a story, it just usually has a male star, right?

    12. SB

      Like The Wolf of Wall Street or something.

    13. MB

      Right, right, right, right. And, um, so I'm like, "I'll write this book and it'll sell so well and my life will change," you know? And I went to New York Publishing and, uh, there was a lot of publishers that wanted to give me a lot of money for a celebrity take-down book.... and I wasn't willing to do that, so I got rejected a lot. But I just kept... You know, I was just persistent and I got this book deal. I hi- I got m- my own press and everything, and I waited to... For this... You know, I, uh, released the book and I, I waited for my life to change. And I think like 100 people read the book or something.

    14. SB

      Really?

    15. MB

      Maybe, maybe a little more than 100 but n- not enough to even earn back my advance which wasn't that big. (smacks lips) And then I said to myself, "I still believe in this story. I still believe that the story is the way out. I just believe it. I could see it. I'm gonna have to bring in the big guns." And I said to myself, "I need to get, I need to go speak to one of the most powerful filmmakers in Hollywood." I had a bunch of meetings, and I was like, "It can't be something small. It has to be something big." And so I made this shortlist of people who really come, who really are successful, who are, who, who are the A-list here, you know. And it was like Shonda Rhimes, Steven Spielberg, um, you know, Aaron Sorkin. And there was another component that this person had to have, another feature to their personality. They had to be fearless because there were so many people, as you can imagine, in the political world, in Hollywood, in, um, you know, billionaires making calls saying like, "Don't make this Mo- Molly Bloom movie," because they don't wanna take the risk at all. Even though I'm... You know, I, I went to bat for them. They don't wanna take the risk at all that they could be portrayed in this movie. Anyway, so I, you know, I, I loved The West Wing and I loved Social Network and I loved the characters that... and, and the sort of like message and humanity that comes out from his writing. So, I was like, "I need a meeting with him."

    16. SB

      With who?

    17. MB

      Aaron Sorkin. And he happens to also be the highest paid screenwriter in Hollywood. So, he's a good bet, right? (laughs) Uh, that number doesn't come from th- thin air. So, most people f- laughed me out of their office. They're like, "Your book sold 10 copies." You know, like, "This... It was in the press a couple years ago. Aaron Sorkin's never gonna look at this." And, um, I just kept with it. I was just persistent 'cause I had seen, (laughs) you know.

    18. SB

      As you'd seen...

    19. MB

      I'd seen how people get successful.

    20. SB

      Which was?

    21. MB

      Persistence. Of course, you have to have a good product. Of c- of course, you had to have a good story. I believed in the story. But I got rejected so many times, you know. So finally, I get this meeting with Aaron, and I remember trying to p- mentally prepare for it. (exhales) Living with my mom, you know. I'm by all societal measures the classic loser, (laughs) you know what I mean? Like, I'm like living in my mom's basement. I have no money. I don't have all, any of the trappings of, of the world and the success world, you know. But I said to myself, "You walk in there with humility of lessons learned, but you walk in there like you are wor-, like you're worthwhile," you know.

    22. SB

      Isn't there some famous quote that he said about how you were the most confident down-and-out person he'd ever met?

    23. MB

      Oh, yeah. So and I was like... When, when, when I was done telling him my story, he said, um, "I will tell you one thing. I've never met someone so down on their luck and so full of themselves."

    24. SB

      So down on their luck and so full of themselves?

    25. MB

      (laughs) I certainly was not full of myself but... (laughs)

    26. SB

      (laughs) That's what you were giving. (laughs)

    27. MB

      That's what I was giving. (laughs)

    28. SB

      And, yeah, I mean the TL;DR of that is he, he takes it on.

    29. MB

      He drops what he's doing. He takes it on. He decides to make it his directorial debut, as well as writing it. The movie comes out. It's nominated for every award, BAFTAs, Oscars, Golden Globes. Um, also, I had done a lot of really good negotiating on my part, on the money part. They wanted to give me nothing upfront and promised me backend, and I'd done enough research to know that that wasn't ever gonna happen. The backend in Hollywood is notoriously, um...

    30. SB

      When you say you did well, what do you mean? Give me something, some... 'Cause how can I gauge that?

  22. 1:20:371:24:04

    Going Through IVF 9 Times

    1. MB

    2. SB

      You, I read that you had IVF nine times.

    3. MB

      Nine times.

    4. SB

      People don't understand the pain of having IVF even once and then it not going to plan.

    5. MB

      Yeah.

    6. SB

      But to have it nine times-

    7. MB

      Yeah. It's, it's the, it's the mental anguish. You know, it was interesting for me 'cause, and I think this is important to talk about, and I'm glad you brought this up. So, I froze my eggs at 36. Um, and I was told, "You're gonna be good. You have a lot of eggs, you're young," you know, whatever. And I, 'cause, and my point is here is, I, I think it's a big money-making industry and I think they oversell the technology and it's not to say don't do it, but to do your own research.

    8. SB

      Mm-hmm.

    9. MB

      In my case, what I realized is doing three rounds of an egg freezing procedure would've probably given me a, a much better shot. The technology's getting better, but eggs are 80% water. So, freezing and thawing is, is kind of tricky. Anyway, so I thought I had purchased this insurance policy on my fertility and then when I met Fiona's dad, I was 41 and I said, "Okay, great. Let's thaw out these magical eggs." And none of them worked and I was 41 and my fertility metrics, basically the doctor said, "I'll give you a 4% chance of making this happen." And nine rounds later, um, it worked. And I'm so happy I didn't miss it.

    10. SB

      But that was a special moment.

    11. MB

      Oh. Also terrifying. Terrifying moment. The most vulnerable you'll ever be in your entire life. Up until the point that Fiona was born, I thought to myself, I believed, I went through life believing, p- particularly after everything that I had just been through, there's nothing I can't handle. And then you have a baby and you realize losing this, this little life is something that I don't think I can handle. And of course there are people that do, and they do it with grace, but you just know in that moment that there is something that would, that has changed in you that will never be the same. Terrifying.

    12. SB

      (paper rustles) Ladies and gentlemen, I'm interrupting this broadcast with a very special announcement. Two years ago, I started writing a book based on everything I've learned from doing this podcast and meeting all of the incredible people that I've had the privilege of meeting. But also from my career in business, from running my marketing businesses, my software business, my investment fund, and everything else that I've been doing in business and life. And from this, I've created a brand new book called The Diary of a CEO: The 33 Laws for Business and Life. If you want to build something great, or become great yourself like the guests that I've sat here and interviewed, I ask you please, please, please read these 33 laws. The book I always should have written. If you like this podcast, this book is for you, and it is available now in the description of this podcast below. And every single day until it's out later this month, one person that pre-orders it, that takes a picture of their pre-order, uploads it to their story on Instagram or social media and tags me will win a gold version of this book signed by me. And there's only 33 copies of those available. So, pre-order it now, tag me on social media when you do, and 33 of you are gonna win a very sp- very special book.

  23. 1:24:041:27:54

    What's Your Advice for Being Successful?

    1. SB

      (paper rustles) Fiona comes to you when she's 18 years old. She says, "Mom, I would like to be a success."

    2. MB

      Mm-hmm.

    3. SB

      What advice have you got for me, Mom? What do you say to Fiona?

    4. MB

      Well, we're gonna be having this conversation well before she's 18. I wanna, I wanna help her cultivate her passions, her talents. I wanna teach her about her mind and the ways that I've had to learn, um, how to manage that mind, how to manage fear, how to manage the internal critic. Um, I want to teach her to sit with hard emotions, not to run with, re- run from them, to figure out what they can teach us. I wanna teach her to go into the shadows, the parts of ourselves that we don't wanna look at, and look at it. Don't wait until you get beat up by the mob, federally indicted, you know, like, drug, addicted to drugs and alcohol to finally go into those shadows to look at the demons that you haven't dealt with. Um, all these things that I learned through-... the trials and tribulations of my life, I wanna teach her at a young age. I wanna teach her that her worth is not dictated by the things that she produced, but she is inherently worthy. At the same time, it is... She will not be happy unless she has purpose in life. I believe that to be true. I, I don't know who said it, but it was very succinctly said, "To love and to work." You know? I believe that people need a reason to get up in the morning, to go into the world and feel purpose. I, I don't care if that purpose is stay-at-home mom or President of the United States.

    5. SB

      Will you teach her anything that you learned specifically from being in those rooms with the billionaires, athletes, politicians?

    6. MB

      Absolutely. I'll teach her about risk.

    7. SB

      What will you teach her about risk?

    8. MB

      You know, I've seen thousands of hands of winning and losing poker and I've kept spreadsheets, Excel spreadsheets, on people for years. And I've then watched the choices they make and how they get to the numbers that I look at the end of the year. And what-

    9. SB

      As in their business choices or...

    10. MB

      The p- the choices they're making in the game, and then in their greater life. A lot of times when people lose, they become, hmm, unwilling to take another big risk. And if you aren't willing to take risks in life, over time, you will lose the game. The people that took calculated risks, over time, won. People that took impulsive risks, didn't. But people that took calculated risks over time and didn't let a past failure or, uh, an external condition stand in that way, won the game. I think a healthy relationship with risk is super important. I think, um, being able to stay composed when there's chaos inside, chaos outside is incredibly important in those rooms. I think being able to know when to use your emotional mind to make choices and know when to use your int- your rational mind and being able to toggle between the two in an intentional and, and, uh, smart way, is super important. And I think ego and greed is the reason that I've seen so many lives come undone, including my own.

  24. 1:27:541:29:37

    What Are You Proud Of?

    1. SB

      The person that sits before me today, you know, been on a journey-

    2. MB

      (laughs)

    3. SB

      ... to say the least. Lived many, many lives and many different chapters. Um, what are you most proud of about yourself now? When you reflect on the person you are versus the person you were, what, what are, what are some of the things you're most proud of about yourself?

    4. MB

      I'm, I'm proud that when I, (microphone rustles) that I, that I stay self-aware. And when I believe that I'm wrong or believe that I'm behaving in a way that is, is not aligned with who and what I wanna be in the world, that I'm willing to either say sorry or do that work really deeply, relentlessly do that work to change. I'm willing that... I mean, I'm proud that I just continued to... I'm proud that I stayed open.

    5. SB

      Is there anything you're not proud of?

    6. MB

      From my past or in the present?

    7. SB

      In the present.

    8. MB

      Yeah, I mean, there are little things that I'm working on, but I wouldn't say that I'm not proud of, of them because I think having grace for yourself and learning how to forgive yourself and, and treat yourself with compassion is a hu-... Is, is something that I had to learn as a survival skill back in those dark days, um, but something that I continue to practice. Uh, the only times that I'm not proud of myself are if I'm staring straight into something that I know that I'm totally ignoring that's causing harm in the world, to myself, to other people.

  25. 1:29:371:31:15

    Last Guest’s Question

    1. SB

      Molly, we have a closing tradition on this podcast where the les- last guest leaves a question for the next guest, not knowing who they're gonna leave the question for. And the question left for you is, what is the message you needed to hear when you were younger that you didn't hear? And who was the best person to say it that didn't say it?

    2. MB

      Um, okay, that's a great question and a hard question. And I think, I think the answer is stop searching for the evidence that you're worthwhile, that you're good enough and just start to believe it. And I think the person to say it to me is me. I think I was my own worst critic. Um, you know, we all have certain challenges in our life, but I think at some point taking responsibility for your own shit is the most important thing a human being can do.

    3. SB

      Are you there now? Like are you there at the point now where you know your self-worth is, isn't gonna come from glory?

    4. MB

      Not 100%, but I'm like 90.

    5. SB

      Do you think, do you think we ever overcome these desires to, to seek, you know, these things? 'Cause they, they feel to be so hardwired in us, especially if they come at a formative age from people that are important to us, like our parents or the context we're raised in, it's almost like a, an oven. It's like if you think about anything that you bake-

Episode duration: 1:34:28

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