A Bit of Optimism - Molly's Game with Molly Bloom

Episode Date: May 9, 2023

Molly Bloom’s life story is one-of-a-kind.  Her Olympic dreams were dashed, so she planned on going to law school. Instead, she wound up running a high-stakes poker game where hundreds of millions of dollars would change hands in a night.  Molly made a lot of money. Celebrities, mafias, and federal informants soon took an interest in her and her game.  Eventually, she lost everything and had no one to blame but herself.Her story later became the Academy Award nominated movie, Molly’s Game, and the lessons she learned from her extraordinary journey have tremendous value for the rest of us.This is… A Bit of Optimism.For more on Molly and her work, check out:twitter.com/immollybloom 

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

How she recognized that she made her own decisions, that she was responsible for the repercussions, and how she took total ownership of everything that happened. The rest of us could really learn a thing or two about what it means to take responsibility. This is a bit of optimism. Molly Bloom, I gather to tell you, I was so excited that you were willing to come and have a conversation because I've seen the movie Molly's Game. And I know you wrote the book

on the same topic and lived the life. And had I not known that it was real, I would have said the story is way too fantastic to have actually happened. What crazy mind could actually come up with this incredible work of fiction only to discover that it's 100% real, that this was your life. And of course, after seeing the movie, went down the rabbit hole of like Wikipedia-ing and reading all of the news stories

because I couldn't believe it actually happened. And it did. For the people who haven't seen this brilliant movie or read this brilliant book, and I know you do this a hundred times, I apologize. What is the thing that you did that I find completely insane? I also find it completely insane at this point

in my life. So when I tell the story, I'm like, did I really do that? So I was a pretty normal kid. I grew up in the small town in Colorado. My brothers and I loved mogul skiing. We are competitive mogul skiers. We started competing and wanted to go all the way. And I just had what I thought was this set path. I was going to ski for the US ski team, and then I was going to go to law school. And there was just no question, no deviation around that. That was my plan. And I got thrown a little curve ball. I got really bad scoliosis, had this crazy surgery in which they fused 11 of my vertebrae together and basically made my thoracic spine immovable. And I was a mogul skier, so that wasn't ideal. And everyone was just like, you're going to probably have to find a new hobby. But for me, it wasn't my hobby. So I got back on the mountain and I guess it was the first time in my life that I experienced

this ability we have to go against experts and parents. And maybe this is where it all started. Anyway, so I ultimately made the US ski team. I was really doing well. I was third overall in North America at this crazy, you know, one in a billion odds situation in which I was at the Olympic qualifier, skied over this little tiny piece of pine bough and my ski pre-released in the air and I crashed and ultimately made this decision that I was going to retire from skiing. And I had just taken the LSATs and I was, you know, ready to sort of pull

the trigger on that part of the journey. But for the first time in my life, I was so heartbroken and so just disjointed that I couldn't get it together. So I decided I was going to take a year off just to be young and be a kid. And I really just wanted to go somewhere warm because I'd been chasing winter my whole life. Because this is one thing that I don't think a lot of people maybe do realize. When you decide you want to be an Olympic athlete, that is your 24-7 job. I mean, you train, your relationships, you sacrifice, you miss birthdays, you miss Thanksgivings, you miss all this stuff because all you do is focus on the Olympics. And now that that is gone, you've missed out on childhood, basically.

Yeah. And it's- So now you want to go reclaim a little bit of youth. childhood basically. So now you want to go reclaim a little bit of youth. Yeah. See what it's like. So I went to Los Angeles and I got a million jobs and one of them was working at this real estate development company. And my boss told me one day, I'm going to have a poker game and I need you to serve drinks at it. And that was the rabbit hole. I just remember being 23 and a half years old and walking into this room and it was, yes, sure, there were A-list movie stars, but there were also politicians and the head of one of the biggest investment banks and somebody who had just brought their tech company public. I mean, this room was insane and it was so compelling to me. This was access to information and people were speaking so candidly. And then at the end of the night, I made like $3,000 for

refilling Diet Coke. So I was like- This is a good gig. This is a great gig. And I just became more and more fascinated with the world and the world of the world of high stakes gambling to some degree but more of this unconventional underground sort of masters of the universe setting like this is the kind of stuff where conspiracy theories come from which is that there's a small group of people controlling the world. Turns out you were in that room serving Diet Coke. Right. And I started to just really understand that I had this skill set that I wasn't aware of. And that was that it was an entrepreneurial skill set because I would see how things were done and I would see a way to do it better. And I was quick on my feet and I was a problem solver. And so I decided to start my own games with the intention

always being, I'm going to do this for a couple of years. Then I'm going to go to law school because I'm a serious person and I want a serious life, but this is an opportunity to save some money and to make these incredible connections. I started making millions of dollars a year. Millions, millions of dollars. Yes. Millions of dollars a year. Just out of curiosity, how do you make the money when they're playing poker? That's a great question because I was really at this point and for many years, I was very set and determined to only do it if it was legal. And so I hired attorneys and they analyzed the federal statutes and they said, listen, as long as you're not taking a rake,

which is what they do in Vegas. What does a rake mean? A rake means when the players bet, the house takes a percentage of the pot. Because if you were taking a rake, then you'd be an unregulated casino, which is illegal. That's right. And so what happened was my game became the go-to game. It was all action. It was the stakes were high. You could sit next to the biggest movie stars and the biggest business people in the world. And there were nine seats and I was in charge of those seats.

And I was also in charge of how much credit was extended. So there was this unspoken rule that emerged that if you wanted your seat back the following week and if you wanted credit and you won at the game, you tip Molly. And so people were winning millions of dollars at these games. So you can imagine if they're tipping even just a percent,

a couple of percent over time, then it was incredibly lucrative and it was incredibly lucrative and it was incredibly exciting. I mean, how big are these pots that people are winning millions of dollars? Simon, I'll tell you that by the time I got to New York and I'm kind of skipping ahead, there were games in which people would win and lose a hundred million dollars in a night. What? It was just... I can't even fathom that. I couldn't either. And I can't now. It seems like a fever dream. That's generational wealth. For sure. That you lose or win in one

night. Right. Playing poker. Right. Okay. So we're skipping ahead. I recognize you were running a quote unquote legal game. Yes. So when did it become illegal? So I had this very naive, optimistic idea that I could be the one honorable, heart-centered person in the underground gambling world you know and it wouldn't get to me you know I would I would just be able to retain who I was and I ran the games for eight years and I would say six and a half years into it seven years into it and not overnight by inches I found myself looking in the mirror and not even knowing who I was anymore. I was raised in a household that really was about value-driven living,

not in a religious way, just moral courage and integrity and doing the right thing. And that drove me and that centered me for a while, but you have to know who I was hanging out with, the company I was keeping and the world that I was in. Everyone was trying to steal my game and screw me over and steal money from me and cheat. It was a world that was completely about worshiping money and the hustle and gamble. I got caught up and I started to make choices that were not aligned with this core center. And I lost the plot. I mean, where do we start? Before we talk about the moral sharp turn, I'm just curious, what was the reason your legal underground game where you made money by taking tips became illegal.

In LA, what I had was pretty sustainable. I was manageable. I had one big game I did once a week. When I went to New York, I built it out. I mean, I went all in. Like I had this huge game in which people were winning and losing $100 million a night. I had the mid stakes and the low stakes and the derivatives of Texas Hold'em. And I started to take risks on people. And I was the

bank by this point. So if somebody didn't pay their debts, I wrote the check. And that was what made my game so popular, one of the components. And I started to make some bad choices. And my debt sheet started to grow bigger and bigger. And I started to put people in seats that if they won, it was going to be okay. But if they lost, it wasn't, I was gambling on people. And so at some of these games where I had more exposure, I started taking a rake to cover my downside and to try to make good on this debt sheet. But I, you know, up until this point, I had a great thing going on because it was reputational suicide to stiff this game.

And there wasn't another game out there that was like it. So when I did my job well, and I had, I'm sure the statute of limitations has passed on this, and I'm not even sure if this is a crime, but like I had bank employees on my payroll. I had private investigators. I vetted people really well and got very good at it. And then I just got sloppy. Did you become like your gamblers? If you just play a nice game of poker,

you can win a little, you can lose a little, you know, it's like the rule of gambling. When I go to the casino is what would I pay for a night out? Because I'm not going to get that money back if I buy dinner or whatever or show. I'll gamble that and never lose it. That was my night out. Right. But you're having people who are literally spending more than they can afford to lose. Yeah.

And you are now becoming like them, which is you're now taking bets with the hope that you will hit it big on this player. But when they lose, you lost big. There's this ethical creep of greed. There's an ethical creep of greed. And I think there's also a piece of it that's addiction. And addiction to what? Well, in my case, I think it was the adrenaline. Most of the players that were playing at the level of losing $100 million, I think they were gambling addicts. And that at some point starts to get into your psyche and really made me question who I was and what I was doing in the world. Okay. And now we have to get to the conclusion of this part of your career,

which is it collapsed. Yeah. Do you know what I find fascinating about this? Like so many things, which is it could have been fine if you didn't get greedy. You were making, as you said, millions of dollars.

I was. In LA with your weekly game, which is still the game to be in. And if you were satisfied making millions doing a weekly game, we'd be talking about this game that you continue to run to this day, this multimillionaire, but greed, millions wasn't enough. No, no. And I also think there was a piece of it that was a bit self-destructive because I didn't like who I'd become. Anyway, so the thing blew up. It was multifactorial.

First, there were some Russian American businessmen that were playing in one of my games. She just made air quotes. And their stories checked out, but I knew in my gut that something was off. And it turns out they were running the biggest insurance fraud scheme in New York City history. And the feds were listening to their phones. And they would come and always paying cash. And then the second thing that happened was one of the players in L.A. who we nicknamed Bad Brad. He comes.

He's the worst poker player I've ever seen. And he doesn't get better. He doesn't seem to understand the simple rules of this game. And he would come and he would lose hundreds of thousands of dollars every night. At this point, I was like, Brad, I don't think you should play anymore. And he was like, no, no, I love it. These guys are my friends. Please don't take my seat away. So then it turns out Brad starts talking about his returns from his hedge fund. And everyone's like, oh, Bad Brad's a savant in trading. So they all start investing with him. So Bad Brad lost $5 million in the game.

He raised $30 million for his fund, which turns out to be a Ponzi scheme. So everyone thought they were hustling Bad Brad, but Bad Brad was hustling everyone. scheme. So everyone thought they were hustling bad Brad, but bad Brad was hustling everyone. And so not only did we have to pay back the 5 million, they all lost their investment. So that happens. Somebody's lawyer leaks the depot to the tabloids. So now it's on the radar. Then I had a run in with the Italian mob because, oh, by the way, and the Russians that were running that insurance fraud scheme had alleged ties to the Russian mob. But now we're talking about the Italian mob. You know, I was the biggest game runner in New York City.

And they came to me and said, you're going to have to give us a piece of your operation. And I tried to explain very logically why I couldn't go into business with them. And they didn't respect that. And they sent this guy to my apartment who put a gun in my mouth and beat me up and gave me this very terrifying message that if I told anyone and if I didn't acquiesce to their demand that they were going to hurt me and find my family in Colorado. And I didn't know what to do. I was so, for the first time in my life, just had no idea what to do. Didn't call the cops, didn't call my family. And then a week later, I hadn't heard from them. And I got the New York Times and on the cover, it said 125 arrested

in the biggest mob-related takedown in New York City history. So I never heard from them again. And then the last thing that happened was I started taking the rake. The feds had put a confidential informant in my games at this point because they were listening to- They found your crime by accident. Right. Exactly. Yes. And then later that year, one of my poker dealers texted me and said, the FBI is here looking for you. And I immediately started packing a bag for the airport, tried to buy a plane ticket from JFK to Denver. My credit card gets declined. My debit card gets declined. I log into my account and my account

balances reads negative 9,999,000. Oh my God. I make it home. The FBI doesn't apprehend me. My attorneys call the feds and they said, your property, unlike your person who doesn't have the presumption of innocence. And we believe on good authority, she's been making her money illegally. If she wants to come in and go on record and tell us how she's been making this money and more details about this interesting career she has we'd love to have that conversation i couldn't do that and the last thing my attorney said is do you want her to come in is she part of this investigation and they said no and if she is we'll let you know. And so that led to, I just went away. I moved in with my mom, you know, in the mountains of Colorado. And I felt

really sorry for myself and had to figure out a way, you know, this has been in the tabloids now. And there's all this, all these rumors. My network is destroyed. I, I need a job badly. I don't have a bank account. I don't have any money. Well, you do have a bank account. It's got negative $9,999,000. Yeah. So I would have to deposit $10 million in order for it to be a functional bank account. I had to do two really important things. I had to, first of all, look at this mess and own the fact that this was entirely my fault. And I had all the information on hand. I had all the opportunities in the world to do something that wasn't illegal.

And here I was. And then, you know, I had to try to figure out how to come back from this. So two years go by. Oh, my goodness. You think you like, okay, I fucked up. I got to get out of jail free card. Literally. I'm going to put my life back together and never make this mistake again. Two years go by. I got sober because as you can imagine in that world, I was in the substances and alcohol and pills and everything were, were a big part of it. Substances and alcohol and pills and everything were a big part of it.

I got sober. I got, you know, started meditating. I looked at the whole mess. I took responsibility for it. I got a job. I moved back to LA. And seven days later in the middle of the night, I got arrested by 17 FBI agents with machine guns and high beam flashlights. And they put me in handcuffs and

they put this piece of paper in front of me that said the United States of America versus Molly Bloom. And I had a day and a half to get to New York City to find an attorney that's going to represent me in this, the fight of my life. I don't have a dime. And I had eight meetings with attorneys the day before the arraignment. And this is a terrifying indictment. This is a Russian mob indictment. 95% of the people that are indicted, I've never heard of in my life, including some guy who lives in Moscow, who's known as the Vor, which is like the godfather of Russian organized crime. I mean, life does not make sense. There's no way to grasp it. And I finally found

this attorney. His name's Jim Walden. He was at Gibson Dunn at the time. And he was like, you need help. What you do in the next couple of weeks is going to determine the rest of your life and I'm going to help you. And I basically had to give him an IOU for the retainer. And we started working together and the the prosecutors wanted a meeting and this is he afforded you credit he did he gave me credit he thought i was oh the oh the irony all right exactly i paid him back every cent um so i start working with jim and the prosecutors want a meeting. And this is the Southern District of New York.

This is a very big prosecutorial office. And they really wanted me to become a confidential informant. And they weren't interested in the mobsters or the Russians. They were interested in celebrities, in the hedge fund managers, and in the politicians. And things that they wanted to know, i didn't know any epsteins or or weinsteins i didn't know people that were doing really terrible things i knew people that were maybe like betting sports or you know doing some sort of like shady hedonistic stuff but i I didn't know, in my opinion, I wasn't going to be making the world a better place by becoming a confidential informant in

this case. All I was going to do was shirk the responsibility of the consequences of my actions and destroy the lives of other people, many of whom I knew their kids, you know, and I knew their wives. Did any of them come to your aid? I mean, you'd looked after them. Some of them you'd extended credit and they were quote unquote, your friends. Did a single one of them call you up and say, can I give you some money? Are you okay? Did they even call you up and say, are you okay? No, but again, you know, I mean, they don't owe you anything, right? They don't owe me anything. I didn't ask for anything. And I wasn't, you know, it wasn't the Peace Corps. It was on the underground gambling road.

And you weren't friends. No. Would I have hung out with them if I wasn't making millions of dollars by their gambling? 99% no shot. So I turned the offer down and I waited to get sentenced. And we all thought I was going to go to federal prison. And my life was, again, a total disaster. And my father and I weren't speaking. All of a sudden, you find moral high ground where, so what? Let a couple of celebrities and politicians get investigated by the feds and be humiliated and so you can stay out of jail. Why didn't you take that deal?

I think most reasonable people would have taken that deal to stay out of jail. So it wasn't for them. It was because I had this experience of what it feels like when I acted not in alignment with what I believe in and who I am. And I hated myself and I didn't want to fight for myself anymore. And this almost delusional confidence that I'd always had was gone. Was it less moral high ground and more giving up? No, because I had been in that place and I'd come out of that place. I had done all this work. I had a very strong sense of pride that these were my choices and I was going to stand for them.

You actually were willing to take accountability. I was. I needed to take accountability. Okay. There's a piece of it that's moral and there's a piece of it that's also strategic. I want a life after this. Yeah, but you could have stayed out of jail. This was my thought. And Jim Walden wanted to correct me every time. But I was like, listen,

if I spend two years in a federal prison, I'll learn a language. Whatever. I can get through it. Get into shape. Yeah. I will make sense of the time there. And I am good at making money, so I'll just make more money. The other one seemed like an unknowable, unendable life sentence. How long and to what degree are the feds going to use me and destroy my life? It was something awful, but finite versus something less awful, but forever. And something that gave me, and this has always been important to me, and you can ask my family because I would open my mouth no matter how much trouble I got in, and I always got in trouble. I have to have agency. Like, I have to feel that I have some sort of internal power.

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

Take the deal. You ignore the better advice. But this is actually the right choice. So one out of three. Well, it's less one out of three what i think is curious is what was it about your gut that was different the third time of ignoring here's the answer to your fascinating and i think very intelligent question and no one's ever asked me this and i've never really thought about it this way but the answer to me is really clear. I grew up in this family with two brothers who were so successful right off the bat, and

their success was so defined. My younger brother was number one in the world in mogul skiing at 16 years old. He went on to have a prolific college football career and Olympic career in skiing. And then he got drafted fifth round of the Philadelphia Eagles after the Turin Olympics. He won, you know, multiple world championships. He was like an Abercrombie model during these years. Please tell me he's an asshole. I wish, but he started a charity in our hometown for like granting wishes for senior citizens because he was worried about them oh i hate him and most recently this kid who we just thought was a really good athlete like

started and sold a software company all right so this is little brother just a prodigy model like empath okay and charming and lovely and all the generous and kind and ethical and then my middle brother's even worse. He's a Harvard educated cardiothoracic surgeon at Massachusetts General who's dedicated his life to helping children with congenital heart defects. And here I was at 35, like millions of dollars in debt of social pride, convicted felon,

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

I love this. Yours is such an exaggerated case of what it means to live a life in constant competition, trying to outdo others, whether it's high school friends or your brothers, your goal is to beat them in whatever arbitrary metric you choose, fame or fortune or whatever else, anything else, the times that you kept doing that, the ski decision, the expansion of your business decision, ultimately it crashes because it is for all the wrong reasons. But when you just sort of resign yourself to the fact that I'm not going to be the richest, the best looking, the smartest, I'm not going to be the most successful, but I'm going to live a life that I enjoy. All of a sudden, the joy goes up, the stable and legal success shows up. I love this

lesson that the only competition is yourself. Unquestionably. And the calculus of it, the components of it are so different than what you think they should be. The things that really give you joy and the things that really make you a complete person and give you peace and contentment look nothing like I thought what they look like. We have to tie up a loose end before we talk about what happened next. So you decided not to cop a plea. Right. And you decided to roll the dice, no pun intended. How did it end out? I got really lucky. I got a judge who was 41 years old, Obama appointed, super disappointed in my life choices. He gave me a full dissertation on that, but basically didn't put me in jail.

a full dissertation on that, but basically didn't put me in jail. And a big part of this was the guidance that Jim Walden gave me. He said, we are going to move with integrity. He had an incredible reputation with the government. He was a former federal prosecutor who went after the five crime families. He knew how to tell an authentic story of somebody who felt bad and was changing their life. And he also leveraged his reputation. And so, you know, I'd love to sit here and say like, oh, well, the judge just saw so much potential in me. I think a lot of it had to do with Jim Walden. The reputational halo that you got when he decided to take your case. That's right.

And I had some great character letters from some great people. when he decided to take your case. That's right. And I had some great character letters from some great people. And, you know, I had real material evidence that I was changing my life. Whereas a lot of the people in my indictment were going and sitting courtside at the Knicks and where, you know, like just hiring really aggressive defense attorneys that were a lot of money. And this particular judge was like, you're an asshole, you know, like, no. And so in a lot of ways, I lucked into it with Jim. He was the only attorney that would take my case, but he was the right one. When did this all come to conclusion then? So I was sentenced in 2014. There's this moment, you lose your legs because even though I was like, oh, I'll go to prison, make the most of it, whatever like when you're looking down the barrel of losing your

freedom there's just almost nothing like it and so you know this this immense moment of relief and then like okay but now what i'm millions of dollars in debt i'm convicted and so i went home and i tried to get and one thing that i derived from running these games and being in this world is you know i got very good you know, I got very good at strategy and I got very good at rationality. And so I went home and I spent a lot of time in the mountains walking, thinking, what is the way out? And what I kept coming back to over and over is like, it's the story, you know, this is a unique story. But I was up against a lot because there were so many powerful people that were so afraid of their secrets being revealed. They were trying to run interference

on a book deal. And certainly after that book got published and I took it to Hollywood, but I had so many meetings and people were so interested in the room. And then it was just like crickets or they would pass. And finally, I just, you know, I got someone to be really honest with me. And they were like, there are so many people that are shutting this project down. And so it was kind of back to the drawing board. And I got very clear on something that there is a short list in Hollywood of people that are so powerful. They don't have to play politics. It's the Shonda Rhimes.

It's the Spielbergs. It's the Sorkins. These people, if they take on a project, not only gets made, they don't have to play politics. It's the Shonda Rhimes, it's the Spielbergs, it's the Sorkins. These people, if they take on a project, not only gets made, they don't have to pander to these people. And so at the top of the list for me was Aaron, partially because he is and was my favorite writer, partially because he's the highest paid screenwriter in America, which tells you something about his batting average. I mean, I needed this to work because the book didn't first round. It did not work.

It did not change my life. It did not give me opportunities. I didn't even out earn my advance, which wasn't even much. So I decided that I needed to get an audience with Aaron Sorkin. And most people laughed me out of their office and ridiculed me and stuff. But Ken Hertz, who I know you know, Ken Hurts sent Aaron the book. And I remember flying to LA, I was living with my mom and I was on the outside, such a low point in my life, but so assured on the inside because I had lost everything and was fearless. And I remember telling him my story and he said that he had

the greatest line after I told him my story. He was like, well, I'll tell you one thing, kid. I've never met someone so down on their luck and so full of themselves. And I can assure you, I was not full of myself. I just wasn't going to quit until I got there. It became like this game, you know, and I had chosen to be optimistic and I had chosen to believe in the impossible. And it happened. Aaron wrote the movie. And how much of what he perceived as arrogance or extreme self-confidence, if we're generous. How much

of it was real and how much of it was because you got really good at projecting that for years of doing just that? Walking into that meeting with Aaron Sorkin, did I think in a million years he was going to write this movie? No. But I was going to give it my best shot. And my legs were shaking under the table and I never thought I'd hear from him again. And it was 10% real in that I believe that humans deserve a second chance and 90% posturing for sure. What are you doing now? So I had a kid.

I have a daughter 13 months ago. Congratulations. Thank you. That's a whole thing. Wonderful, hard, scary, the most vulnerable I've ever been. And I'm- That's saying something. Yeah. And I'm a single working mom. I'm on the speaking circuit a lot because it allows me to work on these other things I'm working on. I'm writing a book with my dad actually on effective presence, which is, it's the science of how you make people feel. Oh, interesting.

Which has, if I look back on my life and I look at what's the most teachable through line that has brought me to success and capacity, It's really focusing on the science of how you make people feel because emotions are the driver for decision-making. I mean, I'm itching to interrupt you and ask the question. It's obvious here, you know, which is how did you make these Hollywood A-listers, these hedge fund managers, these politicians who they themselves have healthy egos, especially when they're winning at a poker table. How did you make them feel? What was different about your room and how you made them feel versus a pickup game at somebody's basement?

When I first went to those games, I found myself walking in and being like, trying to prove myself, right? I'm smart. I'm athletic. I was never going to be the smartest or most talented person in that room. And then I was clear on a shift of like, you shouldn't go in there and try to sell yourself. You should go in there and try to make people feel seen, heard, or remembered, solve problems for people that you weren't asked to solve, invest in their experience, both financially and emotionally, Do a lot of active listening. Authentically look for the unique parts of people and learn how to have dialogue around that. Give me an example. We can leave the names out. Here's a great example of how my game was

different. There is always a moment where someone loses an amount of money that they're so uncomfortable with that they're going to say to you, and I'm not fucking paying that. Okay. And what happens with other game runners is that they get scared and they get defensive and they, and they said, well, F you, you're going to pay it like whatever. And what I was able to recognize is that when someone says that to you, they're in fear. Money is so connected to survival. And so my job then is to address the fear, not my own, to have this ability to overcome myself in this moment, but to help make them feel safe. Just a super easy shift is instead of going in and talking about yourself all the time, just asking questions, trying to

find out what makes this person tick and how you can provide value in their life or in their experience. I used to have pregame quizzes with the people that worked the games with me, and we would cover people's names, the names of their kids, the things they care about, the initiatives they're working on, some follow-up from conversations from the last week, their favorite drink order, their favorite food order. A little goes a long way. What I find so interesting is what you're running is a great customer service business. For sure. Will Gadara came on here a previous episode.

He wrote a book called Unreasonable Hospitality. He was the founder of Eleven Madison Park. And he just talks about how he became the best restaurant in the world by the things you're talking about, listening, making people seen, heard, and understood and offering this unreasonable hospitality. And that's what you did. Yeah. And the same way he became the best restaurant in the world, you became the best poker game

in the world by offering unreasonable hospitality. What you're running is a great business. Right. Well, until it wasn't. Well, I mean, it was, it was a multi-million dollar business because the tips you were getting were based not on the ambiance. The tips that you were getting were because of how you made people feel. Right. And you were running a good business until you got greedy.

Yeah. And that extends to decisions you make when they're not in front of you too. For instance, And that extends to decisions you make when they're not in front of you too. Like for instance, pros wanted to play in my game constantly and they were offering me so much money and a free roll and all these things. And if you truly care about your customer, you're not going to make that choice. You're going to have their back even when they're not in front of you. I think there has to be some continuity there. People have to know that they can depend on you and that they feel safe of you. I think there has to be some continuity there. People have to know that they can depend on you and that they feel safe with you and that you think that they're worth it,

worthwhile. I mean, after the fear of death and being alone, worthiness is like every human's fear, whether or not they're worthy. And it doesn't get like realized as people get more famous or more rich, the hole seems to get deeper. So there's this misconception that those people have their buckets filled and they absolutely do not. Did you live a life where like, you don't want to go through that again, but you're glad it happened? Most days. There are days where I have serious regrets. And most of the time, there's two buckets there. One, since becoming a parent, I have serious regrets from what I put my family through. And the other one is not parlaying it into something really cool and sustainable.

And, you know, because it was a huge cleanup job. It was seven to 10 years of my life. You know, I had to allocate all my creativity, all my time, all my energy to putting this back together when I could have done something else and something that I would have really liked. But most days, I don't play that game. Most days, I'm like, God, Molly, if you don't wake up and pinch yourself in gratitude every effing day for how this turned out for you, then you'll never be happy. Did you actually learn your lesson?

Do you find yourself, when we talk about competing against your brothers, have those demons been exercised? I don't think demons are ever fully exercised. I think you have to stay in a practice. I think the human brain can fall very easily into these lower thoughts, these lower natures. And for me, I have to stay in some sort of practice to keep myself above it. And if I don't, I will fall right into it. I love that moral, which is that the demons are outside the gate for all of us, right? And if you're not, as you said, spending every day living in integrity, if you're not spending every day pursuing a cause higher than simply short-term gain, that it's like water's ability to find any crack. The demons will find a way in. And once they get a grip, whether slow or quickly, like your experience happened, it will unravel. And that's why I think we need to get away from this idea of let's just be so punitive to human beings when they mess up or when they fall into this sort of the way that the

unedited brain is. And let's start to impart different ideas. And that's why I love so many of your talks and your books about this, because you hear it and you're like, oh yeah, that feels so right. But people aren't talking about it. They're just assuming that we should know this. I don't think we just know it. I think we need people to talk about it. And I think we need to impart strategies which enable us to overcome the lower nature, to overcome the jealous mind, the egoic mind, the self-pity, whatever these very sort of like real parts of the human condition are

to rise above it. That's one of the reasons that I was very excited to talk to you because I feel like you are a voice for that. You are out there talking about this almost way to force evolution of human beings into something kinder and more compassionate and more aligned with what actually feels good and is right. Well, thank you very much. Those are kind words. I think what's interesting is it's actually very, very hard to be human. We are cursed with a thinking brain. For sure. And all the things about being human, like all of our emotions and how we manage those emotions, how we manage relationships, like we suck at relationships. We suck at friendship. We suck

at marriages. On balance, we're really not very good at being human. And there's a great irony that with all these gifts that we have for being able to think and our ability to rationalize, we actually have to learn and practice to be good humans. Without a doubt. And I think that that needs to be normalized. And I'm super grateful that I learned that because otherwise you're in this loop where you fuck up and you're bad at being a human and then you get mad at yourself and you feel guilty and you feel like you're not worth anything. And it's not easy and it takes practice and it takes work and it takes instruction. And for me, like a meditation practice is a critical component because I have to get to this place where all these things can go on in my head, jealousy, self-loathing,

greed, fear. And I have to be able to somehow sit above that and make other choices. What advice do you give to young people now? First of all, I just want to teach them the things that I have learned that have enabled me to live a different existence. And one of them is to engage in some sort of practice where you start to be able to manage your mind. Because these kids right now, if you look at their stats, it's dire out there, the amount of anxiety and depression and disconnection. And so getting to a place where you start to understand how to facilitate a healthy mind and how to not listen to your thoughts all the time and not listen to what's going on and

be able to have some agency over that, I think is always the first place I start. be able to have some agency over that, I think is always the first place I start. The second place I go to is this practice of being able to sit with hard emotions and hard feelings and A, not act on them right away and B, not catastrophize them and just know that this is going to pass. Because when I was young and I would feel something big, I would be like, I have to change this. I have to success, money, whatever it is. I have to throw something at this to change it. And what I learned as I got older and as I suffered many consequences for trying to escape the way that I felt inside is that you can engage in this very powerful, very courageous practice of just sitting with it. Another thing that I want to tell them is that you can engage in this very powerful, very courageous practice of just sitting with it.

Another thing that I want to tell them is that there's this misconception, especially when you're young, that you get one shot. That is not the truth. You're willing to grow and get better. You get as many shots as you're willing to take. And finally, that life and growth and transcendence is about starting to get outside of yourself and starting to make your life about the greater whole, the greater good. There's never been a time that I was sicker than when I was completely self-absorbed and selfish and thinking about myself all day and thinking about how I should win at the cost of other people. That was the sickest. I couldn't even be with myself. I had to use drugs or alcohol or success.

It's just, it's a human sickness. And so, you know, starting to engage and I'm all about the action, right? Like everyone, words are pretty, but sitting down to meditate, having an inventory practice where you look at who you were during the day and how you could improve that and where you're going to go from there. Where's the action? So starting to engage in actions that make your life about not just self. Molly, I could talk to you for hours. Yeah, I could talk to you. I have so many questions. I mean, we have time for one. One? Only one?

Okay, so what do you think the thing that you have done that has most changed culture has been? Like, is there a statement? Is there a concept? Is there... Because you really did change the conversation. I tend not to live on past accomplishments, though I can be proud of things. I'm always like, all right, what's next? Good. Now what's next? But if I do look backwards, I think the thing that I'm proudest of as an accomplishment is that I've contributed to the English language, which is the concept of why is now a noun. I can read an article in the Wall Street

Journal, for example, and somebody who doesn't know me, doesn't know my work, hasn't read a book or seen a talk will say the problem with this company is they don't know their why. And that is a noun. That's huge. That's so cool. And I smile because I'm not given credit. I don't care. I'm proud of the fact. And if I go back to early on in my career, when I started defining the golden circle and I started defining the concept of why, I never put TM on the corner of it. Everybody has their idea and they instantly put a TM and a trademark. Well, the problem with the trademark is then you're the only one that can do it and talk about it and share it. It's not an accident that the word and the concept joined the vernacular. It's because I wanted it to, because I enjoy it. I enjoy reading the

article and smiling. That's the joy I derive because my happy place is actually behind the scenes. I like working in the shadows. I'm a backstage person. I've never been much of the desire to be on a screen or on a stage. So it's ironic that my career is on, you know, in the front of the proscenium because my happy place is backstage. So many people are trying to do what you have done, but it's kind of like the concept of the philosopher King, right? Like the philosopher King never wanted to be King, but they authentically cared about something else that qualified them to get there. And so I think it's your deep passion for the authentic shift and not your own glory, which kind of circles

it back to what your point was about my third good choice and two other ones that were rooted more in the shallows. Here's what I've learned. Competing against others, like our family, our friends, our coworkers, competing against them is a fool's errand because there's no such thing as beating them. Ultimately, what it'll lead you to, as you discovered the hard way, is that you find yourself on a treadmill that you have to make things bigger and bigger and bigger at your own self-destruction and sometimes the destruction of those around you. But always your own self-destruction. And the idea of trusting your gut when there's an ethical compass versus trusting your gut because you seek more fame or glory is a big difference. Big difference. Huge. And I walk away with those lessons and I'm very grateful for that. Thank you. Well, thank you for pointing those out to me too,

Well, thank you for pointing those out to me, too, because I will probably think about this a lot and use it in my speech. But I'll credit you. No, no, not necessary. Unnecessary. Molly, you're great. Thank you so much. Thank you so much, Simon. If you enjoyed this podcast and would like to hear more please subscribe wherever you like to listen to podcasts and if you'd like to learn more about the topic you just heard please check out

the optimism library at simonsenic.com where you can get access to more than 35 undemanded classes about leadership culture purpose and more until then. Until then, take care of yourself, take care of each other.