How I Manipulated The World's Richest Men: “They Lost $100 Million In One Night!” - Molly Bloom (Molly's Game)
嘉宾：Molly
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§01Transcript — part 1
He put a gun in my mouth, beat the hell out of me, and 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. Doug, the poker princess, the former waitress who took a small poker game run out of a dingy nightclub to the biggest underground poker game in the world. For Hollywood celebrities to millionaires. They literally made a Hollywood movie about it.
The game turned from legal to illegal. I had become the biggest game runner in New York City. Leo DiCaprio, Ben Affleck, Tobey Maguire, politicians. I was making $4 to $6 million a year. It was unbelievable. $250,000 buy-in. So I couldn't sit down unless I brought $250,000 to lose. That's right. And you saw someone lose $100 million in a night. 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.
The FBI gives you an ultimatum. They're going to give you millions if you snitch on the players in the game. I had 48 hours. What happens then? Molly, what do I need to understand about your earliest context to understand you? Going right in. I think it almost always starts with the family and childhood. And I am from a family of, you know, my two little brothers are incredible humans, but like the craziest overachievers you could ever imagine. Yeah.
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, you know, she was this. She insisted on kindness and integrity. So there's 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 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 skill set. But I knew that I had to be successful, and this is not hyperbolic. I literally did not want to 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.
I don't want to live. Did you mean that? 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 accomplishments. And my brothers had already started to make that happen. And I, Hmm. Why law? 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 started to kind of read books about the law and fiction a lot.
I mean, I loved stories. 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're fighting to save somebody who's innocent, the sort of high points... the aspirational points of what it would be like to be a lawyer in a movie or a book you're thinking about the glory yeah yeah for sure why do you think you cared so much about glory 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 then feel relief from that existential ache that followed me around my whole life, you know? So you You go off and try and pursue a career in law, at least that's what you think you're going to do. Yeah. You're going to go to Harvard, right? 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 energy and ambition it took to go do all these things. I just had, I had hit a wall and I think I was really questioning the conventionality of it all. I ended up like not applying to law schools and 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.
When you moved here, your father, again, bringing him back into the picture, he's a very ambitious person. How did he receive this news that you were coming to LA? Not happy about it. Not going to financially support it. Really disappointed. So you get here and he's no longer supporting you financially at all. So what do you do to make money? I mean, I got a job. I had to get a job the day I got here and I went to this restaurant in Beverly Hills.
went to, you know, got a job for a couple of days. It was terrible. And then I went to this other restaurant and kind of lied and said, because 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 of 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.
He said, but, you know, people seem 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. Oh, so it was the boss of the restaurant that offered you the job as the executive? Yes. They had a bunch of holdings. They had some real estate. They had some restaurants. They had a fund. So you became his EA, his PA. Yeah. And this led you to poker. Yes, he came in the office one day and he said, and there are always zany things sort of like thrown at me.
And he said, I need you to serve drinks at my poker game tomorrow night. And I tell this story because it's just so indicative of the naivete and where I was. I remember... Googling what kind of music do poker players like to listen to and what do they eat? And then I proceeded to make this incredibly embarrassing playlist with songs like The Gambler on it. You know, and got this cheese plate and showed up for this very fancy poker game 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 toby mcguire and leo dicaprio and then you know but 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 Quite a few people have come out, as you say, and said that they played in those games.
Yeah. I was watching a video earlier of even Dan Balzerian, I think, says. Yes, Dan played. He played in those games. Were those games legal or illegal? Legal to play in. Legal to play in. For sure. Legal... I, when I started running the games, I hired 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. So you start as a basically an assistant to the games that your boss is running.
These are secret games, right? Right. Very secretive. Very. And take me on the journey of what happens next. 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. But man, am I intrigued. You know, getting to be a – at 23 years old, getting to be a fly on the wall in this room where 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 have ever had access to and to learn from people at this age of 23 when I didn't know who I was or who I wanted to be.
And number two, that there was something that happened when there was a token or a chip was that was the economic system that made people very liberal. Because I'd worked as a wait, you know, I was I was a 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 didn't want to seem like a novice. 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. What's effective presence? 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'm like, I'm like, I'm like, I'm like, I'm like, I'm like, I'm like, I'm I don't, I want to stay in this room more than anything, but I don't know how I could ever confer value in this room. Did you feel like you were going to be kicked out of the room? I just felt like maybe I was disposable. Like maybe they would just bring in 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 hope to gain and, and where my mind was going with this opportunity. And, you know, I said to her, but mom, I have 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 going to 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 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 information. 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 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 for the first six to seven months is just creating a real connection with people, observing them 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, whether it's at the poker table or in business or just in life and focusing in on the details and really... getting outside of yourself and becoming curious and becoming a great listener, which by the way, you are an insanely great listener.
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, you know, has experienced, has a public following or whatever, it's so seldom that someone just sits down with them and listens, just gets in it with them. So funny, as you were saying that, I was just thinking about how much of a competitive advantage listening is. We think that the competitive advantage is had in speaking.
But 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 the world of business, to deliver them a solution to their problem, which is getting a sale, to create the upper hand, you simply have to listen. Yes, absolutely. And you have to listen for as long as you possibly can. And this is what the great thing, what I've learned from doing this podcast, but even from this conversation is, I'm, my next question is going to be so much better for the fact that I listened to you.
Right, and actively listened. Actively listened. Presently listened. 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, you know, all of a sudden it's like competition up, egos up, and then there's not true connection.
You can't penetrate that kind of wall, can you? If you've both built two walls between yourselves because you're showing off. Right. You need the walls to come down to form the connection. Yeah. When people hear that, they go, you know, 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. Which, you know, the fine line between sales and persuasion and negotiation and manipulation, it's all there, you know.
Is this positive manipulation? So, yeah. 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 for me because I used to do that, right? I used to... 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 talking points so that I could instantly connect on something with you and show you that you and I are the same.
And I don't really do that anymore, although I don't hate that strategy. 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. to see versus if you kind of take a few breaths before you go into a room and you say this what I want to 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 in a greater way to humanity. And by the way, that can also include yourself, you know?
But I think it's about disconnecting from the outcome, disconnecting from the transaction and connecting as a human being. So how'd you get from being the waitress in these rooms serving drinks to running your own poker nights? This is a funny story. Okay. Couple months go by, right? And I'm like, I don't wanna serve drinks in these rooms. 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. And also, I'd sort of learned in those six to eight months that I was an entrepreneur. I was a problem solver. 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, 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, you know, I just bided my time and I tried to figure out how I was going to 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 going to be calling you. And by this point, I had really kind of gotten into, like, I had started to think about how I was going to build this game. I was keeping the books on everyone. I was recruiting players. You know, I really had, I was doing much more than just waitressing. And... I thought about it and I was like, I got to take my shot. I can't just go.
I can't just let him take this. 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, 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 out of this dungy basement, had it catered by, you know, the best restaurants in town, 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 really, as the games were on, I really like got into the science of scent science and temperature and humidity and food and all these things that elicit the feel good chemicals.
And so and then I invited everyone except for my boss. And at the end of the night, the game went really late. And then at five in the morning, I got this text message from my boss. And he said, get over here. To this day, I don't know why I went. I just went. And he made me go wait in this bedroom. And he made me wait for a long time. And I said to myself, he's going to kill me. I mean, I don't even know what's going to happen right now. Because he 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. I'm really worried about your soul. Like, you're not a nice person, you know? 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're going to 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. It's hard to know how to feel about that moment now, sitting here decades later. So from that moment when you host that first game, you upgrade everything. You upgrade the experience for your customers. Eventually, you set your sights on New York for a variety of different reasons. And you moved the games from being based in California and LA to being based in New York City. I lost the LA game. You lost it.
Someone took it from you. Yes. Karma. Yeah, totally. Not going to argue with that. Who took it from you? One of the most famous movie stars in the game. Leonardo DiCaprio. Someone took the games from you. A movie star said, I'm going to go do it at my house. Gave me an option first. You can either start making less money. So this is very interesting. There is this player in the game. Who you can't name. I won't name. But they're a big male movie star.
Making so much money. Okay. How much money are we talking? Like hundreds of millions? Yeah. Okay. 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 was no one better than he was. Dan Balzerian said that he was kicked out of the game because he was really good. Oh, well, listen. Dan showed up playing this kind of...
ruse that he was just this clueless trust fund kid okay and people bought it and i said 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 i wish you the best so you kicked down balzerian out of the game i had to He was too good. Yeah. Okay, so he was telling the truth.
Yeah. And yeah, for sure. So this Hollywood star that stole your game from you. So he was really obsessed with the game and he was obsessed with the money that he was making and being the biggest winner. And the truth is at the end of the year, the money that I was making by that point was millions. And he believed that was money that should be going into his pocket, even though by this point I was traveling the world recruiting players. I had a staff of 20 people.
I handled all the logistics. I handled credit extension collections. I was on the hook if someone didn't pay. I had a full business. I was paying my taxes. There was so much work and sweat equity, and I had branded the game in this incredible way. And I took notes every single game. Here are the areas that it works. Here it doesn't. Let me do some deeper research. And just really turning down cash and cars and free rolls from the pros to get a seat to protect the integrity of the game and paying the debts from my own bank account to make sure people got paid faster.
I mean, I wasn't serving drinks anymore. And so when he said to me, you're making too much money, you have the option of making less and I'll let you keep the game. Look, by this time, I had become a strategic thinker. I had really been able to get out of emotional decision making. But I do believe that there's a time and a place for emotional decision making. And so I knew that turning down that offer, there was a large, the odds where I was gonna lose the game, but I knew that accepting that offer meant no autonomy for me, no freedom and no dignity.
And you know- What was the offer, sorry? I would have to cap my salary and make it, and have him approve how much I'm making. What was he bringing to the table where you couldn't just kick him out? Was he bringing a lot of influence and celebrity power? Yeah, in this town? So he basically said to you, listen, you're making a lot of money. I'm bringing a lot to the table because 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. Yes. So he kind of wanted to make you his employee. Right. How do you feel about that? I never want to be anyone's employee ever again. But how do you feel about him? Because when you said it, you looked a bit pissed off, to be honest. Did I? A little bit. You looked a bit like there was still a little bit of maybe resentment to that moment. You know, I think that there's just conviction to that moment. Right. Because I think we live in a day and age where a lot of people try to... Not in a day and age.
It's reality that a lot of people 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 turning the offers down. So you said no, what happens then? Called me about a week later and with this almost jubilant laugh and tone was like, you're done. How could he ensure that you were done? He had colluded with the biggest... whale in the game, a whale in a gambling 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. So you lose the game? I lose the game. I was devastated. What's going through your mind at that moment I'm done. I'm never going to be able to make this much money again.
I'm never going to be, I'm going to have to go join some, you know, I'm going to have to go work for someone else. I'm not going to be able to be my own boss. I'm not going to live in this fascinating, adventurous underworld where I get to, you know, pull the strings and move the chess pieces. And I have to go join the real world where, I'm not extraordinary. You know, I'm just telling what's gone through my mind. Now, when I say these things, it's like, it is what it is.
So you eventually moved to New York. Yes. 30 years old at this point. I'm 31 at that point. Okay. Yeah. So, you know, 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 rooms 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, 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. But then I got angry and I had something to prove and there was just nothing that was going to stop me.
What made you angry? Feeling like I had been disposed of so effortlessly. Something that I, you know, something stolen from me that I had curated and built and, you know, said karma before. 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. I ran the games with ultimate integrity. You know, 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 going to build the biggest poker game in the world, like five times, ten times bigger than the game in L.A. And then I would go away. I decided after doing some research that I would do it in New York City because 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.
Secondly, it was 2008. So the economy and Wall Street had just been brought to its knees. In the most profound ways, it's probably the Depression. And thirdly, there were some pretty scary characters running games in New York who'd been doing it for 20 years. But, you know, it's testament to when you're obsessed with something. 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 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 where I could improve on that. I already knew I could bring the branding and the experience, which was meaningful. It truly was meaningful. 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're 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 having integrity. And then I... 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, if somebody stiffed, I would pay. What does a stiff mean? Meaning they lost money in the game and then didn't pay the debt. Okay. I don't understand that surely to get the chips they have to pay for them up front. No, when you run a weekly game, ultimately you establish a credit relationship with someone. Okay, right. Um, because otherwise, like, these people would have to bring $5 million in cash every week.
§02Transcript — part 2
It's just not reasonable. It's not feasible. So tell me about the peak of your New York games then. So when you're at the peak, what does that look like? So I started this big game. It was. They're all just called Molly's game. Okay. 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. Say that again. Explain all of this to me like I'm a chimpanzee from that documentary you were talking about before we start recording.
So when you sit down to play at a poker game. There are a couple 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. So I couldn't sit down unless I brought $250,000 to lose. 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 at the start of the round.
Yeah. And there's a small blind and a big blind and it just goes around the table. 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 two 50. And I would have to decide in that moment, can they pay this? Are they good for the money? And so I would have to start to establish this relationship, this financial relationship with people based on trust a lot of times.
But there are a couple of things 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... And you couldn't just go to the police if they stiffed you, right?
No, there's no recourse unless you're willing to go to muscle. Mafia. Yeah. Organized crime. Why couldn't you go to the police? Because it's not illegal to stiff me or a game. It's illegal to stiff. You need a gambling license in order to have those types of privileges. So you can go to jail in Vegas for stiffing your gambling debt. But you can't go to jail for stiffing me. Okay. I gave you the money. It's a loan. So you're saying you saw someone lose $100 million in a night?
Yes. How did that happen? The game was playing huge. They were also playing backgammon. They were also betting sports. Obviously, I can't guarantee $100 million. So I'm out after a certain point. But and that was shortly before I got in trouble. But that game that I established, the combination of the big game in L.A. and the big game in New York sort of joined together and became a billionaire's game and people over a year's time would lose a billion dollars.
People were, I mean, there's rumors that a couple billionaires went broke playing in that game, fully broke. And this, here comes to a part of this story that is, I think, really important. I started to see something I could not unsee anymore, which was in the beginning, I just believed rich people could never lose their money, knew what they were doing. And that this was just their form of entertainment. And what I started to see is that a vast majority of the players in these games, particularly the big games, were gambling addicts.
Totally owned by the addiction of gambling. And I, at some point, had to decide whether I was okay with playing my part in that. And my answer by my actions was clearly yes, but I paid a huge price for it inside. And that sort of started to enable me to make other decisions that were not in line with my integrity. And that had a directly inverse proportional effect on how much I liked myself, how much I... my self-esteem, how much I believed in myself, the kind of person I started to be and what had been up until this point, about trying to be an entrepreneur and be gutsy and make money and, you know, sort of like source power, but do it in a way where I'm retaining who I am and integrity, started to be exclusively about the money and the power and the status.
And I started other games in the city, and I didn't care if somebody could afford it or not. And I was drinking a lot and I was taking a lot of, um, pharmaceutical pills like Adderall to stay up and Xanax to come down and, um, you know, just started to live this life of, of very little self analysis. You compromised your integrity. I did big time. How I'm 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, 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 draft, 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 push an activity that was ruining a lot of people's lives, That was an insult to my integrity.
That was getting out of alignment with who I am and what I care about in the world. What were you good at? So at that peak moment, when you do a skills order of why you were successful, what appears on that skills order? 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. Not a win-win. And all of these things, 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. Yeah. Right? 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 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? I was very depressed. Very disappointed with myself. and completely powerless over these forces. Money, 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 consistency and formulation of pharmaceuticals. They allowed me to be productive and not feel myself. Not feel the world. I was drinking a lot. Why didn't you want to feel the world?
What were you escaping from? Myself. What I was doing. The way that I was living... What was it you were so ashamed of about the way that you were living outside of the games? I had stopped really communicating, showing up for my family. At times didn't treat people that worked for me as well as I'd like to. I started to have... You know, New York 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 provide them with opportunity.
The truth is, is that I 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, 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. Those were the reasons. Were you in a relationship at this point?
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 the secret relationship, but I didn't want anyone to know because he was...
He didn't measure up to the persona that I was trying to sell, which was very hurtful to him. How did he know? I told him we can't tell anyone. Did you tell him why you can't tell anybody? He said it's bad for business. Is that what hurt him? You're just saying it was bad for business? Because if you said that to me and we're in a relationship, I think, okay, you don't want to complicate the dynamics. You don't want some people to know that someone you're involved with romantically is also kind of attached to the game, so.
Yeah, I mean, I think in the beginning it made sense, right? But down the road, I think it became very clear. And we had conversations about it. Some point the mafia show up. So here's the kind of levels and stages of the train wreck. So the first thing that happened was 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 corruption. And interesting for them. The next thing that happened was I had a run in with Italian organized crime. And 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 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. You know, if you want to continue to run these games, you're going to have to give us a piece. And we all know, we've all seen that movie, right? And I politely declined their offer and tried to explain to them in business terms why that wouldn't work for me.
And I just went on my merry way and started to avoid their calls. And 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 took everything that was in my safe, including photographs. You know, a couple of 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 Colorado.
Oh. And so a couple things here. First of all, if somebody comes into your apartment 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 that And I was completely alone in it. I was too afraid 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 way over my head. And my family's 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 going to do. And then I got so lucky. You know, my only contact with the outside world was food delivery and the New York Times. And a couple of days later, I got the New York Times and it said 125 arrested and the biggest mob-related takedown in New York City history.
And I never heard from them again. But you know. Disaster is a coming. It's just. And the last thing that happened before the whole thing blows up was, 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 L.A. was that I didn't take a rake. you winner's 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 six million dollars a year and um just from tips yeah so where where did that four to six million dollars a year come from from The winners.
So the winners would play in the game, and if they won, you know, they would tip a percentage, one 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 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 is here looking for you. Don't come here. And so, you know, I knew finally it was game over. It was game over. Hmm. And you realize that when you got that call saying the FBI are here looking for you. How do you feel at that moment when you hear someone calls me and says the FBI looking for me?
Terrified. I want my mom and I want my dad and I want to go back in time. I'm going to do any of this. Don't even know how to process this. And then a couple 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 or looking around every corner. Are they going to be there to apprehend me? And, um. packed a bag and grabbed my dog and, you know, tried to book a plane ticket to 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 negative $9,999,099 in all of my accounts. Why? Because the feds had seized every single penny. And then some. So what happens then? Did you manage to get out of New York? I did. I managed to get out of 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 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, you know, let's just keep it simple. Someone 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, we're not interested in her as, you know, we're not pursuing anything criminally against her. And if we are, we'll let her know.
So I just went, I just went home. What do your parents think of you when you come home at this point? 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. So I think my dad was angry. My mom's just scared. And I think they're also relieved, right? Like they were, you know, they knew that what I was doing was dangerous.
They knew it was dangerous. I was up late at night running around with large sums of cash. I mean, they had many sleepless nights. At some point, the FBI gives you an ultimatum regarding becoming a snitch. Oh, OK. So it took two years. For those two years, I moved in with my mom. I got sober. I 35 years old. No, I'm not 35 yet. I'm 33. Got sober. Trekked to Machu Picchu, did some deep soul searching, 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 myself, you know, and I've been living with my mom and my grandma in the mountains of Colorado. So I moved back to L.A. 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. How much? The press release said 90 years. I think realistically it was more like 10. But, you know, I have a day and a half to get to New York City to find an attorney that's going to represent me in the fight of my life and I don't have a dollar. My dad and I aren't speaking. Why? Because he got mad at me and I got mad at him. Because 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 out of jail. My dad 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 six million dollars. And 250 to even look at it.
And so I have like eight meetings that day before the 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 was at a very prestigious law firm and kind of like listened to my story, looked at my mom and said, I'm going to 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. And 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 going to be our strategy and our angle. 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 taking on this case 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, how far I had come from that, and for what. And 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 who I am. And one of those is integrity and doing what I believe to be the right thing.
And a couple weeks later, the prosecutors wanted a meeting and they really wanted me to be a confidential informant. Snitch. Yeah. And Jim believes this is the whole reason that they brought the indictment. So that you would snitch on the players in the game and... 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 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 bad, like if Epstein was in my game and I knew that he was trafficking children or whatever, like I would have given that information freely and before this. But what I knew... Was Epstein in your games? No. I thought you were saying. No, no. I'm saying if there was a character like him, right?
I would have never protected someone like him. But the things that they were interested in, to me, who's booking sports. It's about to become legal in two years in New York and New Jersey. You're going to drag somebody's family through the mud and I'm going to be, you know, your accomplice with that. Did they offer to restore your bank accounts if you snitched? They offered to give me all my money back. Which was how much money? Millions. So they were going to give you millions if you snitched?
Yeah. And also, they were going to give me a deferred prosecution, which would have kept, you know, sort of given me a guarantee that I would stay out of jail. And I went home and I, you know, I had a very short amount of time to make this choice, something like 48 hours. And here's where I got to with it. This place that I was in was 100% my fault. I did all of this. I had near perfect information about the law. I had great parents. I had a 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, 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. So you ultimately get sentenced? 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 going to 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 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 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 going to lose your freedom, you don't realize that, how big it is until that happens, you know, and probably would have been even bigger if we went the other way. But I mean, I felt like I, I mean, 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's a heart surgeon. He's in residency. He just graduated Harvard. My other brother just got inducted into the 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 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. You know, one of the things I always talk to my friends about is as you become more and more successful, you get to see behind other curtains. I call it, you know, it's like a. Totally. Yeah, like it's a curtain 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 set of ways. And you go, what the fuck? You guys have been back here doing this stuff all the time. So I can so, that so resonates. Playing all these money games that I didn't even know existed. Like you do this and you trade this and you do this and you flip this and you go, what the fuck? I was like, I was earning like minimum wage over here. And you billionaires around here just like doing billion dollar things with these little games that I didn't even know existed.
And that's what I've come to learn in my life is like, I got to see behind a lot of curtains and I was like, oh fuck, I can do, I can earn this much money without doing any work or you can do like this. What are those things that you came to learn about when you got to see behind the curtain? A couple things. First of all, I thought behind that curtain, I was going to find the most contented, generous, non-petty, like extraordinary people. And that's not what I saw for the most part.
There were exceptions. I just saw people who were kind of like unwilling to fail. Because? I don't know. Because they're obsessed with money. I mean, you know, it was just drive a lot of times. Or being dragged. Or being dragged. Right. Was it more being dragged than drive? Or was it more drive than dragged? I.e., could they stop if they wanted? You know, were they in control of their obsessions? Dragged. In those settings. Hmm. That's what I've tend to tend to find.
Yeah. I met a lot of billionaires and I with the odd exception. I'm like, damn, unhappy. Yeah. I can't stop. Yeah. Have you ever read that book? The psychology of money? Yeah. Yeah. Don't you love that story in there? I love it. I don't know what story in particular you're talking about. Remember when Joseph Heller is at the house of the billionaire and someone walks up and says, Heller, 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, why could that possibly be enough? Boom. 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, not that I'm a mom. But I chase it in healthier ways, you know? Heli skiing, whatever it is, climbing mountains.
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. What else did you see behind that curtain? So you saw a lot of dissatisfaction with life? Yeah. I saw a much bigger world than I knew existed. And a much more malleable world. That's super key, that malleable point.
Yeah, I thought like the walls were a lot more solid. In life, generally? Yeah. But you realize success is something that we can all bend, control, manipulate. I think all is a pretty powerful word. I think if we are willing to do the work that it entails on ourselves, yes, I think success, money, abundance is much more available than I originally thought. Is that because you see very ordinary people achieving very extraordinary results? And then once you see how they're doing it, you go, ah, okay.
Yes. Precisely. That's also what I feel. Yeah. That's cool. 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. or not ends, but you know, begins again. So I'm walking around the mountains. I'm thinking to myself, like, what's the way out? And I just realized there's a unique story here. We've seen this version of a story. It just usually has a male star, right?
Like the Wolf of Wall Street or something. Right, right, right, right. And 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 there was a lot of publishers that wanted to give me a lot of money for a celebrity takedown 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 got my own press and everything.
And I waited to, you know, I released the book and I waited for my life to change. And I think like 100 people read the book or something. Really? Maybe a little more than 100, but not enough to even earn back my advance, which wasn't that big. 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 can see it. I'm going to have to bring in the big guns. And I said to myself, 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 short list of people who really come, who really are successful, who are the A-list here, you know? And it was like Shonda Rhimes, Steven Spielberg, 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 the billionaires making calls saying, like, don't make this Molly Bloom movie.
Because they don't want to take the risk at all. Even though I'm, you know, I went to bat for them. They don't want to take the risk at all that they could be portrayed in this movie. Anyway, so, you know, I loved the West Wing. And I loved Social Network. And I loved the characters and the sort of, like, message and humanity that comes out from his writing. So I was like, I need a meeting with him. With him. Aaron Sorkin. And he happens to also be the highest paid screenwriter in Hollywood.
§03Transcript — part 3
So he's a good bet, right? That number doesn't come from thin air. So most people 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 going to look at this. And I just kept with it. I was just persistent because I had seen, you know. As you'd seen. I'd seen how people get successful. Which was? Persistence. Of course you have to have a good product.
Of course you have 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 mentally prepare for it. living with my mom, you know, I'm by all societal measures, the classic loser. 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 worth, like you're worthwhile, you know?
Isn't there some famous quote that he said about how you were the most confident down and out person he'd ever met? Oh, yeah. So when I was like, when I was done telling him my story, he said, we'll tell you one thing, I've never met someone so down on their luck and so full of themselves. So down on their luck and so full of themselves. I certainly was not full of myself, but... That's what you were giving. That's what I was giving. And yeah, I mean, the TLDR of that is he takes it on.
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. Also, I had... done a lot of really good negotiating on my part, on the money part. They wanted to give me nothing up front and promise me back end. And I had done enough research to know that that wasn't ever going to happen. The back end in Hollywood is notoriously.
When you say you did well, what do you mean? Give me something. How can I gauge that? So I can just tell you that I got 15 times what someone normally would have gotten in my position. And your position was? A book that didn't really sell. You were the owner of the IP, I guess. Yeah. Life rights. A life rights deal. Like if that book had become a bestseller and it already had a built-in audience and I had a million followers on Instagram and, you know, there was this compelling package.
Sure. So how well did that movie do? It did extremely well. I mean, 50 million people saw it. Do you have an idea of numbers of like value? Do they give you a value? Because I know they say opening box office was X. Like lifetime value? Yeah. They don't because you have a back end. They give you a sort of convoluted back end number. But everyone made money on the movie. And it got nominated for awards. And I'll never forget... getting the bank wire again.
And it takes a really long time. You know, you don't just get paid up front, you get like 50 grand. And then you get the rest of it three years later, four years later, whenever the movie gets made. And it was a rocky road to make the movie because it was all set up at Sony. Everything was going smoothly. It had this big budget, like big movie studio budget. And then Kim Jong-un. got pissed about the interview. Remember the Seth Rogen movie? And he hacked Sony Studios and the chairwoman was Amy Pascal.
And she was the one that really believed in the movie and she had to step down. And then the new chairperson wasn't that passionate. And so then we had to set it up kind of like at festivals. So, you know, nothing's ever a smooth ride. So you get a big check from this movie. I do. But I'm still I still owe millions. Not not today sitting here, but at that point. So I had to figure out. What is what's the next move? And. I remember the first time I didn't even think about speaking, you know, like a speaking career or anything.
Um, I just remember the first time I got hired to speak, it was in front of thousands of people for Google and I had never spoken publicly. And I think I just got on that stage and just blacked out. It was so awful and I was so bad at it, but the money was compelling. the adventure was compelling. And so, you know, it allows me now to make a really great income and then also work on the other things I'm working on, which is a podcast in the community called The Smart Girl's Guide to Everything.
It's basically using the strategy, the access, the network, the resources that I've been able to accumulate in my life and applying it to real life. And then I'm writing a book on effective presence and I have a one-and-a-half-year-old at home. Which wasn't a straight ride, right? No. I read that you had IVF nine times. Nine times. People don't understand the pain of having IVF even once and then not going to plan. Yeah. To have it nine times. Yeah.
It's the mental anguish. You know, it was interesting for me, 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 going to be good. You have a lot of eggs, you're young, you know, whatever. And I, cause 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.
In my case, what I realized is doing three rounds of an egg freezing procedure would have probably given me a much better shot. The technology is getting better, but eggs are 80% water. So freezing and thawing 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, it worked. And I'm so happy I didn't miss it. That was a special moment. 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, 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 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 is changed in you that will never be the same. Terrifying. Fiona comes to you when she's 18 years old. She says, Mom, I would like to be a success. What advice have you got for me, Mom? What do you say to Fiona? Well, we're gonna be having this conversation well before she's 18. I want to help her cultivate her passions, her talents.
I want to teach her. about her mind and the ways that I've had to learn, how to manage that mind, how to manage fear, how to manage the internal critic. I want to teach her to sit with hard emotions, not to run from them, to figure out what they can teach us. I want to teach her to go into the shadows, the parts of ourselves that we don't want to look at and look at it. Don't wait until you get beat up by the mob, federally indicted, you know, like addicted to drugs and alcohol to finally go into those shadows to look at the demons that you haven't dealt with.
All these things that I learned through. the trials and tribulations of my life. I want to teach her at a young age. I want to teach her that her worth is not dictated by the things that she produced, but she is inherently worthy. At the same time, she will not be happy unless she has purpose in life. I believe that to be true. 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 don't care if that purpose is stay at home mom or president of the United States. Will you teach her anything that you learn specifically from being in those rooms with the billionaires, athletes, politicians? Absolutely. I'll teach her about risk. What will you teach her about risk? 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.
As in their business choices? The choices they're making in the game and then in their greater life. A lot of times when people lose, they become... 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 won. didn't. But people that took calculated risks over time and didn't let a past failure or an external condition stand in that way won the game.
I think a healthy relationship with risk is super important. I think 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 rational mind and being able to toggle between the two in an intentional and 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.
The person that sits before me today you know, been on a journey to say the least, lived many, many lives in many different chapters. What are you most proud of about yourself now? When you reflect on the person you are versus the person you were, what are some of the things you're most proud of about yourself? I'm, I'm proud that when I, that, that I stay self-aware and when I believe that I'm wrong or believe that I'm, Behaving in a way that is not aligned with who and what I want to 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. Is there anything you're not proud of? From my past or in the present? In the present. Yeah. I mean, there are little things that I'm working on, but I wouldn't say that I'm not proud of them because I think having grace for yourself and learning how to forgive yourself and treat yourself with compassion is a huge...
is something that I had to learn as a survival skill back in those dark days, but something that I continue to practice. 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. Molly, we have a closing tradition on this podcast where the last guest leaves a question for the next guest, not knowing who they're going to 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? Um... Okay, that's a great question and a hard question. And 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.
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. Are you there now? Like, are you at the point now where you know your self-worth isn't going to come from glory? Not 100%, but I'm like 90%. Do you think we ever overcome these desires to seek these things? Because 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 an oven. It's like, if you think about anything that you bake, you can't unbake the thing. Like you can't unbake a cake. You know, there's lots of things you can like, you know, separate using various chemical processes. I love that, yeah. I think maybe if you're willing to go live a monastic life and just meditate all day and like not live in the real world, even then, I know that for me, anytime I think I have something completely figured out, something fixed, something else will happen in life and it'll crop up.
So that's why I think it's so important to have a process for how you deal with these things. And I think anybody that says, I did this work on myself and now I'm fine, isn't being fully truthful. I agree. I completely agree. And I think that's the most honest answer to give. And I also think it's the true answer. It's the answer that all the psychologists and psychologists and psychiatrists that I sit here with tell me as well. It's the answer I've seen in my life that it's more about management than it is about taking our traumas or our hardwiring to zero, which...
And I think that's important to say because people that are struggling with the same recurring patterns in their life hear that and go, thank God it's not just me. Yeah. You know, because they'll beat themselves up when the therapy doesn't work or the podcast they listen to doesn't change them. Right. Or like when staring at the sun and sitting in an ice cube bath doesn't fix their like. They're still toxic after their ice bath. You know what I mean?
And they're like, fuck, they want a refund. Molly, thank you so much. Thank you so much. Thank you for your wisdom, your honesty. You don't have to be so honest. And in particular, the amount of life lessons you've been able to draw from this experience, I think is of tremendous value. So it's no surprise you're a speaker. I'd bet extensively on your podcast being a huge success as well. And I'm really excited about this book because I really do think that effective presence is clearly one of your absolute, you know, dominant skills.
Just from meeting you today as well, when the minute you said that and explained it, I was like, oh yeah, I get it. So, and that's an unbelievably powerful skill because all we face in this world is other people. Yeah. And so knowing how to get the best from those people in whatever context that might be is ultimately the superpower that anyone could possess.