Walker Webcast: Molly’s playbook: Life lessons from the world’s most exclusive poker game


On today’s Walker Webcast, Willy is joined by entrepreneur, speaker, and author Molly Bloom, who first came to national attention running a high-stakes poker game in Los Angeles’ Viper Room. She turned her story into the 2014 memoir Molly's Game, which was adapted into an Academy Award-nominated film. Since then, she’s built up a prolific speaking career and now hosts a podcast, Torched, about “the heat of competition, the cost of greatness, and our universal love for sports—and their inherent drama.”

Molly starts off with her upbringing and how it affected her career trajectory. She grew up in Colorado, graduating from the University of Colorado and training to be an Olympic skier until she was injured during the qualifiers. Growing up with two successful and intelligent brothers, she says, inspired her to do something that would have an impact on the world.

She moved to LA and worked odd jobs, including for a “tyrannical” real estate investor. These experiences taught her how to deal with unfair treatment, push herself to learn new things, understand service, and have an unrelenting work ethic.

Most importantly, she says, she learned how to solve problems and build relationships through “listening authentically and asking questions.” This skill was invaluable in growing her poker game in Los Angeles and then New York. “Even among celebrities and the super wealthy, all humans just want to feel understood,” she says, adding that she began to base her own success on how other people felt in her presence.

Success brought about “a manic desire” to keep moving up—as did the “obvious sexism” she noticed in the game of poker. She used the hurt and anger to make herself even better. And as her earnings soared, she felt “less powerless and more like a true entrepreneur.”

After the government set this new precedent for criminalizing poker, they seized all of Molly’s assets and began building a case against her. (Her poker game was only considered a crime when she began taking a portion of the pot, Molly explains.) Two years later, 17 FBI agents with machine guns came to her door to arrest her.

Fortunately, she says, her lawyer, Jim Walden, recognized she needed a second chance. “In my most vulnerable times, he brought me back to a place of integrity and optimism.” For example, when the justice department urged her to wear a wire to capture evidence against other players, she “said no from a place of integrity.”

In May 2014, after pleading guilty to reduce charges, Molly was sentenced to one year of probation, a $200,000 fine, and 200 hours of community service. She was initially relieved at not being sent to jail—but then realized her entire network and career had been ruined and that she had to get strategic in her next move. The book and the film provided that second chance. So did sobriety. She tells Willy, “For me, being sober meant facing the reality of the choices I had made and how I needed to change.”

Today, Molly is a public speaker who spreads awareness on “the importance of believing in yourself, cultivating authentic relationships, and having a growth mindset.” She and Willy close out the conversation with her sharing what she sees for her next chapter.

Key Ideas

0:53 - Willy welcomes guest Molly Bloom
8:09 - Before poker: The early stage of Molly’s career
12:07 - Molly’s secrets to effective relationship building.
27:43 - Moving to a new market and clientele
34:05 - Moly explains the game of poker
35:18 - The emergence of the lawsuit
39:30 - The impact of Molly’s lawyer, Jim Walden
44:40 - Molly’s journey to sobriety
46:06 - Getting a film adaptation
49:12 – Lessons learned throughout all of this

Webcast Transcript

Willy Walker: Thank you, Susan. And good afternoon, everyone. It's a super, super great pleasure to have Molly join me today. I owe my friendship with Molly to our mutual friend Rick Sapkin. And so, I want to give a shout out to Rick, because without his introduction to Molly, I knew about Molly's Game, I knew about Molly's story, but I didn't know Molly. To have her on the Walker Webcast is a real pleasure and honor. So, Molly, let me do a quick intro and then we'll dive into my first question for you.

Molly Bloom is an American entrepreneur, speaker, and author of the 2014 memoir Molly's Game. She's a graduate of the University of Colorado, trained to be an Olympic skier and was injured during the Olympic qualifiers. In April of 2013, she was charged with running a high stakes poker game that originated in the Viper Room in Los Angeles, which attracted wealthy people, sports figures, and Hollywood celebrities. In May 2014, after pleading guilty to reduced charges, she was sentenced to a one-year probation, a $200,000 fine, and 200 hours of community service. A film adaptation of her book, Molly's Game, was released in 2017, starring Jessica Chastain and directed by Aaron Sorkin. The film received a 2018 Academy Award nomination for Best Adapted Screenplay. Molly has a podcast, Torched, which we will talk about today, as well as a prolific speaking career that takes her all over the world to speak to corporations, industry associations and YPO chapters.

So, Molly, we're going to bounce back and forth a little bit on your story and its lessons. But I got to start here. The game Molly's Game was your life's passion that you worked so hard to build and curate. Yet when Tobey Maguire asked you to bark like a seal for $1,000 or lose the game, you refused to do it. Why?

Molly Bloom: Oh, because that would have cost me my dignity. (Laughs)

Willy Walker: But I think about that, Molly, and I think about how much I mean, when you in the book, you talk extensively about you were this woman from Colorado invited into a situation that you knew wasn't normal and you saw the opportunity that it presented, and you grabbed it. And when you grabbed it, you grabbed it with all of your focus and all of your attention and every ounce of energy you possibly had. And you talk about how much it meant to you and how it was your path forward. And so, when I think about all you had invested in and all you'd put up with to keep it going, and then all of a sudden Toby says, “bark like a seal.” And you said, “No, I ain't going to do that.” It seemed like a relatively low price to pay to keep it going.

Molly Bloom: (Laughs) Well, it depends on, I guess, who you are and what's most important to you. And, you know, I think that I've made a lot of decisions like that that seem to cost me a lot in the here and now but paid off later. That story is a little bit more complicated. The story you're talking about was the culmination of basically a demand for compliance. And in a lot of different ways in how I got paid and how I ran my business, he wanted to be the puppet master, and I couldn't roll like that. I had to be my own woman. I had to run things in the way that I felt was right and true. And, you know, it seemed like a high cost at the time. But the cost of being his lackey would have been so much greater.

Willy Walker: So, let's back up for a second. Born in Colorado. Two younger brothers that you affectionately call “tiny, evil, superhuman prodigies.” So, talk for a moment about those two tiny, evil super prodigies and how they influenced what you ended up doing with your career so much.

Molly Bloom: Okay. So, the evil part is just a joke because they happen to be incredible humans. But let me just break it down for you. So, little brother Jeremy, number one in the world in mogul skiing at 18 years old, went on to win three world championships and compete in two Olympics, going into both Olympics as number one in the world. When he retired from his skiing career in Turin, after Turin, he went to the NFL Combine, got drafted in the fifth round of the Philadelphia Eagles. He was an Abercrombie model somewhere in the midst of these athletic careers, he started a charity at 21 years old, granting wishes for senior citizens in our community. And most recently, the kid that we thought was just an athlete founded a software company and sold it for a bunch of money. So that's little brother. Middle brother, Harvard educated cardiothoracic surgeon at Massachusetts General who has literally dedicated his life to saving children with congenital heart defects. And so, like this was my dinner table and their skill set presented so early on in these two categories that were very important and fundamental in my family, which were athletics and academics. And, you know, I spent my childhood just really reeling, thinking – what's my thing? You know, like, how do I get a seat at this table?

Willy Walker: So, one of the ways you got a seat at the table was to dress up as a duck fairy when you were five years old. I actually Molly, as an aside my CFO at Walker & Dunlop, Greg Florkowski, whose daughter wants to be a fairy unicorn for Halloween here and he told me that dinner two nights ago, and I said Molly Bloom was a duck fairy when she was five years old. It's awesome there are parallels here. Maybe you can steal part of her costume. But you read biographies about women who changed the world. And when I read that about you, yes, you had these two brothers who were incredibly talented, sort of seemingly out of the womb. And that was always a little bit of chipping at your heels, if you will, and finding your place. But you also always had the intention to change the world. I mean, reading biographies about women who impacted the world. That said that you had some interest in really making your mark.

Molly Bloom: No question. And I wanted to do it in a way that was good, pure, and kind. And I really credit my mom for that. One of the reasons why I read those biographies is because I came home from school and I said, “Mom, in my history classes, all we learn about are men.” And so, my mom went to the librarian at our school and arranged for me to be able to check out all these books, all these biographies about women who had impact. The other tenet that my mom is so passionate about is doing things with integrity and kindness and by keeping close that moral code. So, I really credit that intention to great parenting and then I took it out into the world and got a little distracted.

Willy Walker: We're going to get to the distraction piece. So, an extremely good student at the University of Colorado, I think you had a 3.98 GPA. You take the LSATs, the average LSAT acceptance score to Harvard Law School is I think a 68 and you got a 72.

Molly Bloom: Okay, hang on –I got to correct the record here. Sorkin inflated my LSAT score. (Laughs) I did well.

Willy Walker: I love that because we're going to talk about that a little bit. But there are very few things you and I have talked about before, but there are very few things that aren't reality in the movie. You mentioned to me that the crash and there's actually a perfect segue way to it. So, you said that they also hyped the cracks that you had at the Olympic trials, but you did have surgery on your back when you were 12 years old. You got two rods in your back, and you landed on it. That ended the skiing career. You head off to L.A. to quite honestly, just get warm and kind of get out of the cold and winter season. And you do a bunch of odd jobs running around waiting tables, this, and that. Then you start working for, per your words, “a diabolical, tyrannical real estate developer,” and you call him “Reardon” in your book. To anyone who's listening today, you can go find out what Reardon's real name is if you want to. And he's done a very good job of cleaning up his LinkedIn profile and thinking that he is as nice a guy as anyone you will ever meet. But if you read Molly's book and watch the movie, you will realize that Reardon is lacking a little bit as it relates to, let's just say he would have many H.R. violations if he were to work for Walker Dunlop. Let's just leave it at that.

Molly Bloom: I think that's fair.

Willy Walker: With all that said, Molly, as I listened to you and the lessons you learned from him, you learned how to put up with shit. You pushed yourself to learn new things. You watched him sell people on deals that they should have never invested in. And I sort of started to appreciate how much of a jerk he was because he actually made you an entrepreneur. He made you understand service. He demanded an unrelenting work ethic, and then he introduced you to the game, actually his game.

Molly Bloom: Yeah. You know this character that we call Reardon, when I started working for him mid-twenties, who had been too smart for his own good, had raised a bunch of money. (This was pre-2008) and to be honest Reardon has grown. And in a very interesting turn of events was one of the only people loyal to me when everything fell apart. You know so I think in those days, he was a psychopath. There's no way around it. But you're right. I think the most important thing I learned from him is he would figure it out. If there's a problem. He would solve it. There's an industry he didn't understand, he became a student of it. There was no sort of barrier to entry that he didn't surmount in a very short amount of time. And that was so instrumental for me to learn to be that level of problem solver and to look at things as like, this looks like a closed door, but I'm going to figure out how to open it no matter what. And, you know, that was huge.

Willy Walker: Well, as I think about that, Molly and I think about the way that you managed the game. Here are these stars who seemingly have agents and all sorts of people who can do things for them. But one of the things that I was so interested in is when they would text you at the table and try to get a read on who some guest was, you knew everything about that guest. When they wanted a table at a fancy restaurant, which I presumably would think they could have anyone kind of call it, you figured out how to get it, get it quickly, get it perfectly, except for etc. And it was that sort of concierge service that you provided beyond the attractive women to serve drinks and knowing what their favorite drink was and having a nice cheese plate. But it was that 1 to 1 relationship you built with some of these A-list stars that really made you the glue on the game. Is that a fair assessment?

Molly Bloom: I think that's absolutely a fair assessment and, you know, in the early days, I was just serving drinks at this game and these people were so prolific. And I assumed like you assumed – they don't need me. What kind of value can I confer in this room? And I think it's this really important lesson that human beings are human beings, and if you figure out ways to make their life easier, to solve problems that you're not asked to solve, just show up for people and not walk into a room thinking, “Okay, what can I gain right now?” And flip that to “What can I give?” That's my challenge. How can I upgrade this experience? How can I cultivate this authentic relationship? How can I actually get invested in this person as a human being and in their life? And even those people at the top echelon and I'm not just talking about A-list actors. I'm talking about the heads of some of the biggest investment banks in the world, some of the most well-known politicians, and people in the tech world. I only named the people that had been named in the press or that had named themself. But there's a whole other universe that was represented at those games. To be able to start to see that human beings are human beings and if you find a way to make people feel taken care of, seen, heard, remembered – that works across the board for everyone. And what that involves a lot is dropping your own ego and your own fear of who am I compared to these people? And thinking about it like, I'm just going to show up, you know, I'm just going to show up for them and be of service. And that was of tremendous value there.

Willy Walker: They also placed a lot of trust in you without having reason to do it, and I don't say that in a critical way. All I'm trying to say is you were new to them. You were someone who was introduced to them through Reardon. And yet immediately you're texting with them. You got their cell phone numbers. I mean, you talk about the discussions that you didn't have with your family and your friends about what you were doing and how hard that was because you wanted to sit there and say, I'm texting with Leonardo DiCaprio and telling the world, and yet you didn't. That was a really mature thing to do at the time, but many people would have failed on that test. What was it that made you realize that if you told the world about what we were doing, it was going to end pretty quickly?

Molly Bloom: I think from my early sports career, I had an ability to get a handle of myself, emotions, impulses, to not only be disciplined in the world, but to be disciplined internally and that helped a lot. Also, something I realized when I started with these games is I have this ability to be strategic, to think about the long game, to run the tape forward and to make choices that are aligned with the greater outcome. And I think that, in a way, also comes from sports and how much mental discipline you have to have.

Willy Walker: There's one line in the book that just talks about this customer service focus, because I think this is so applicable from what you did with the game to anyone in the business world. And you say, “You can't place enough value on someone being seen, heard or remembered.” You're working with people in this game who are all seen more than almost anyone else on the face of the planet. They're Hollywood stars. They're on screens all over the place. But you identified how to identify with them 1 to 1, how to make them feel, seen, heard, and remembered. I mean, any tricks in all of that other than just texting and thinking about what they like to do? Was there anything that was unique in the way that you made them feel seen, heard, remembered?

Molly Bloom: Yeah, I did a lot of listening. And that listening seems to be an art that is disappearing in a conversation. So often people seem to listen, but they're kind of computing what they're going to say next or how they're going to sound smart and it's not authentic, interested listening. Another thing that I did is I would take notes on my conversations with people so that the following week or the following day I could check in. You know, we were talking about this yesterday in progress. Whether it's a deal that they're working on, a relationship issue that they're having. Two things that come to mind. First of all, to assume that people who are seen often, that satiates it. It's almost the inverse. It's like a drug they need. They want it more. And so, there's really no cap on how much people want to sort of feel special. And it's not this, like, cryptic, malicious thing. I mean, if you look at how human beings are designed and their core fears after the first three, which are death, suffocation, and imprisonment, the next two are all about not feeling worthy, not feeling good enough, and addressing that on this level and understanding that is so important. And then the other thing is, even though a lot of these people have all these people interested in their life or seeing them, there's often this underlying thing of “but I'm just doing this so that I can gain something” and learning how to sort of submit that. Of course, that was my play, too. I'm not telling you that I was the Mother Teresa of the gambling world. It doesn't work but starting to just be a real human being and be like, okay, so I want to win. But I'm going to take it personally whether or not these people feel good in my presence. You know, I'm going to take their experience personally. That's going to be part of my personal win. And so, to start to do work on yourself where you're not so transactional and your outcome of success is not just the dollar amount, but really like the effect you're having in the world. And I think that that's a buildup of skill. I think empathy. I think character. I think all of these things are a buildable skill. And I think that over time, if you don't build it authentically, you'll get found out.

Willy Walker: So, in the second game, you and the dealer decided to split your tips, and I think it totaled $15,000. So, you walked home with $7,500. And in the book you write, “I realized I had endless stamina when it came to making money.” And there's a period there Molly, as I read the book, that reminded me a lot of Julia Roberts in Pretty Woman of running around Hollywood and trying on dresses and all sorts, just as I listen to you talk about walking into Barney’s to buy a dress and paying with cash and the woman who's selling you the dress thinks that you are a prostitute and you're like, I'm not a prostitute. I didn't make this money by selling my body. I made this money doing other things and just take my cash and not my credit card. It just reminded me so much of that scene and I listened to you, and it was almost as if you were manic at that time in the sense that there was just this opportunity in front of you that seemed so incredible, and you just bought into it so fully. Did anything bring you back to Earth at that time?

Molly Bloom: Interesting question. I think your read on it is absolutely correct. I think there was this manic desire to figure it out, to stay in these rooms and ultimately to own these rooms. And it wasn't just the money, although the money was huge. What the money meant was that I don't have to be powerless anymore. And that was the genesis behind it. And that was the drive. I had novel moments of buying expensive dresses and even buying a Bentley at 25 or whatever. But what it really was for me was I don't have to feel powerless. I have my thing, and now I know I'm an entrepreneur. And it started to fill that hole created in childhood. Feeling like nothing or a nobody or not knowing what I was going to do or what I was going to be. And so, I think that was the mania. I got brought to Earth many times. The first time was when Rearden said after 6 to 8 months of hosting the games and starting to think through how I could upgrade the experience and how to cultivate these relationships and then Reardon took the game for me.

Willy Walker: So, Reardon took the game from you. I have already told the Tobey Maguire story as it relates to bark like a seal. So, you decide to move to New York, and it's important to keep in mind where the economy was, because this all started in the early 2000 when the economy was going along, and you moved to New York just before the GFC, so the world was shifting quite a bit. But you go into great detail talking about the fact that not only was the clientele distinct, the game was distinct to where you were in your life was distinct. You say in the book “This time I wasn't going to be replaceable. I became the bank.” Explain for our listeners what changed between L.A. and the way you ran the games in L.A. and when you went to New York, which made it so that you had been displaced, you lost the game. And as a result, you kind of look to how you end up owning the game rather than being a player in the game when you go to New York, so to talk that through and where that ended up crossing the line.

Molly Bloom: Yeah. So, the first time I lost the game was when Reardon took the game in L.A. and then I staged a coup. I had my own game.

Willy Walker: With Tobey's help, right?

Molly Bloom: With Tobey's help, yep. Because, by that time, I had made some pretty strong allies. So, I took the game from Reardon or started my own game, however you want to look at it and did really well. And then six years later, I was by all means guaranteeing the game. There was one time when someone stiffed and we kind of chopped it up, the dealer and I then we paid for it, but I wasn't in an official capacity bankrolling the game. It was kind of like if someone stiffs, then the game will chop it up. But I had become really good at vetting people and knowing who to extend credit to and collecting on that credit. And, you know, I developed the skill. And so, when Tobey took my game in L.A., this would've been a great time to go back to school or to parlay this into something that was scalable, that was less in the gray. That was always the plan. My plan was not to be a game runner forever, but my plan was to learn from these people, save a bunch of money, which I did. I saved millions of dollars. I was making millions of dollars a year and then parlayed it into some career that is scalable, that I could tell my parents about, that was more legitimate. But when Tobey took the game in the way that he did, I didn't want to go out like that. And so, I was like, I'm going to build the biggest poker game in the world. I'm going to do it in New York City, do it on Wall Street. And like you said, it was 2008. So. You know, it's sort of a tough road.

Willy Walker: One is you're quick in the book to say, “The best way to get over feeling like a loser is to become a winner.” And you very clearly put it out there. It's sort of I mean, there was a little bit of vindictiveness in that I'm going to move to New York and reconstitute this game.

Molly Bloom: Oh, yeah. I have something to prove for sure.

Willy Walker: The other piece to it is just before you became the bank, Molly, you state in the book that it was crossing over and banking the game was what broke federal law. But just curious, the actual game is in L.A. of taking over a suite at the Four Seasons and having a private poker game, is that 100% legal? As long as you aren't banking the game?

Molly Bloom: So, it actually wasn't banking the game that put me in violation of the federal statute because I wasn't charging interest on the money I would extend or anything, I was just covering. The factor was taking a rake, taking a percentage of the pot. And up until this point, yes, I was doing it legally, both in L.A. and in New York in the early days, because I had an event planning company. I produced these events and then there was this unwritten rule, unspoken rule in these games that if you wanted credit, if you wanted your seat next week, you take care of Molly. And so, people are winning and losing ridiculous numbers. $20 million, a $100 million, these kinds of numbers. And the winners would tip. And that kept me out of the fray or out of the felony. In New York, I started taking a rake. And that's what broke me down. But, you know when I got to New York, it was just this daunting environment. I didn't really know anyone I knew about this mythical game. Mostly hedge fund guys that played for ridiculous numbers, but, you know, trying to break into their little club and that game seemed impossible. And there were a couple of game runners who had run the games in New York City for 20 years and had all these contacts. And so, I looked at this, what seemed like a very oversaturated market, very closed system, and a very terrible time in financial history. And I just thought, I'm going to figure out where the holes are. And so, I just started, I got to the people that were playing that huge game. But I also interviewed a ton of poker players in New York City, and I said, “What's the problem with the market? What's the problem with the industry?” And what I found time and time again is that these people would risk of a lot of money. They would sit down and play these games. And a lot of time these gamers, even though they're taking a big rake and making a big percentage, they would only pay if they got paid. So, it's kind of a Ponzi scheme. And so, it clicked. If I become the bank, if I have this ultra-safe game on top of everything else, that's sort of like if someone walks in the room and they can feel like James Bond for the night and they can do business deals at the table and they know it's completely safe and secure monetarily. This is going to disrupt this industry. This is the way that I can innovate, and I can take over and that's what I did. And that became, you know, within a couple of months, I was running New York City poker.

Willy Walker: I'm fascinated by the fact that when you started at this, Reardon was your boss, and he was it was his game. Then you created your own game having known the people around you and having some of the biggest names in Hollywood know you and you sort of to some degree have Tobey as your partner. Now, all of a sudden, you've gone to New York all on your own. You don't have a partner. And not only is it a new city, but it’s also new clientele. But you're a one-horse band. I mean, you are out there on your own. And as I read the book, I just sort of thought, how did you think that you'd be able to survive on your own? The amount of chutzpah, the amount of confidence in yourself that you had to have. And it actually reminds you of Aaron Sorkin when you went to pitch him on the movie, he said, I've never seen someone so down on their life, their luck with so much overconfidence in themselves. On that, Molly, I mean, honestly, you move across the country, a whole new market, whole new clientele, and you go do it on your own. That’s fascinating.

Molly Bloom: That was so important for me to do, because otherwise I would have always thought that I got this thing handed to me and yes, I capitalize on an opportunity and what have you. But to go to New York City, probably the toughest city in the world. And to go into this underground environment by myself as a young woman and do this was so crazy. So stupid in a lot of ways. But really so important.

Willy Walker: For a moment on that, not only doing it alone, but being the only woman in the room. You study the history of women who made a mark on the world. You'd had success out in L.A.. But, you say – no women ever played in your game. This was a testosterone-driven, male monopoly on this world. Talk for a moment about what you learned. You say in the book, Molly, that there were some people who, when you were serving them drinks, they'd engage with you, and they were very nice and sociable. But the moment that you started running the game, they couldn't talk to you anymore. I mean, how did you deal with that abject sexism?

Molly Bloom: Yeah, so I didn't let it stop me. I saw it happening. It was uncomfortable. Sometimes it hurts my feelings, look I'm still in my twenties and I just didn't let it stop me. I found ways around it. I found ways to make yourself the best at what you do. You don't buy into it, and then you just get into solution mode at every turn. It just becomes another problem.
Starting a business, running a business, starting a family – all these are problems. You know, it's just problem after problem and how well you navigate those problems, those obstacles. I've found that ultimately determines whether or not your outcomes are good. And so, I just used the hurt or the anger or the humiliation as fuel to get better, to make myself better, to make myself more formidable. And I just kind of powered through it. That was how I handled it. And I just want to make one point here, if I would have let pros in the game, there would have been women that played. But at this time, my game was the $250,000 buy-in and it's like women are probably too smart to risk $250,000 on a Tuesday night poker game.

Willy Walker: But I've heard you say that not letting pros in was one of the keys to the success of it because it made it an amateur game. And people like Bradley Ruderman could come in and lose $5 million at the table, even though you later found out what it was behind Bradley's game on why he was willing to lose $5 million. It wasn't that he was willing to lose $5 million and was making money on the other side of it. But we'll talk about Bradley in two seconds. But on it, what was interesting was you got new entrants by going to Vegas, talking to people, and saying, send me your players. But was there a prerequisite that you weren't looking for any pros? You were looking just for amateurs?

Molly Bloom: I was looking just for amateurs. What I found really early on is that in order for this game to sustain, you want people of very equal playing styles and skill level, because then you have these huge outcomes at the end of the night. But I was keeping numbers on everyone at the end of the year mostly that the money is just changing hands. So, if I would have let pros, then they would have sucked all the money out of the game. The game would have been over. And in the beginning, throughout my whole career, I had pros offering me the sun, moon, and stars, three rolls on their money, meaning I don't have to risk anything, and if they win, I win. Straight cash. Like all kinds of things. And you know, that's just one of those important things you have to think about in the short term this seems like a really great deal. Long term, this is the death of my game.

Willy Walker: One thing that I thought was interesting. Annie Duke has a new book out called Quit. In it she did a study as it relates to pros versus amateurs in Texas Hold 'Em and the typical pro they'll play 25% of the time, they'll fold 75% of the time. Whereas the typical amateur plays over 50% of the hands dealt to him or her, which I thought was really interesting that the pros can look at the cards that are dealt to them and they will typically three out of four times just fold right at that point. Whereas the amateurs always sort of have this hope that they're going to have a workout and they'll keep playing it.

Molly Bloom: Yeah. And I think in my game it was probably more like 80-90% that they were playing.

Willy Walker: They keep playing because they have so much money, I guess. Talk for a moment on that, Molly, there's something now called Game Theory Optimal. Let's talk about poker, because there are a lot of people listening who either play it or don't know a whole lot about it. But what's Game Theory Optimal because it seems like that's the new thing going on in poker these days.

Molly Bloom: Yeah, it's basically just using the data, what you know about the stats and probabilities and odds and playing that. Poker has this the old school poker like stigma, these like cowboys/cowgirls come in and they're like, you know, on their gut instinct and their ability to read people. That's how they're winning the game. And the people lose when they overprivileged their gut instinct or, sort of like their alleged ability to read. And the people that are winning are playing the numbers. You know, they're playing the odds there. There's a perfect way to play the game. And, you know, there's quants and all this stuff. And that's how people are playing now.

Willy Walker: So, I mentioned Bradley Ruderman, who is a hedge fund guy who set up a Ponzi scheme. He gets nailed by the Feds in the process of the Feds coming after him. He basically squeals on the game, tells them all. And that was one of the reasons why a number of the names in the early game were published, because they were published in that lawsuit. And you were very clear in only putting those names in your book and not putting the names of the unnamed out of that lawsuit there. But the Feds now are coming after you, as I said, in the lead in they throw the book at you. The movie starts with the Feds coming in and basically 17 FBI agents putting up against the wall with bright lights in your eyes and semi-automatic machine guns. One of the things that they brought against you, Molly, was allegations of sports betting. And I find it very interesting that part of the allegations in the suit against you were about sports betting, which is now legal in I don't know whether it's all 50 states, but sports betting is ubiquitous everywhere and we're seeing it in the world. You have a great episode of your podcast talking about sport betting, but I was interested, you were a pretty active sports bettor while you were running the game, is that not right?

Molly Bloom: I never booked bets. I was never a bookie. I knew that that was very clearly a felony. But I knew all the sharp action, meaning I knew these handicappers and these people who studied the games and I had access to great information so I would bet on the games. Yeah.

Willy Walker: So, there are two 19 numbers that have a lot of significance to you and your brother. One of them is 1955, which I see the significance to you, and the other one is 19.8, which has great significance to your brother Jeremy. You want to explain to our listeners why 1955 and 19.8 have significance to you and your brother.

Molly Bloom: Okay. So, correct me if I'm wrong, because you listened to this sooner than I did. 19.8 is a stipulation in the NCAA charter, right? So, Jeremy played for the University of Colorado, and was having a really prolific college career. You know, the first time he touched the ball, he ran it for 80 yards for a touchdown, packed stadium. And this was as a freshman. But he was also skiing competitively, which is a very expensive sport, and wanted to be able to accept his endorsements. The NCAA says no. So, he actually takes it to court. The judge in his case was a huge Jeremy Bloom fan, but an even bigger University of Colorado fan and wanted to rule in favor of Jeremy. But there is this stipulation in the NCAA charter 19.8 that said, if they find Jeremy guilty, then they can invalidate the whole season of winning for University of Colorado. So, the judge had to rule against Jeremy.

Willy Walker: Correct. The judge wanted to rule for Jeremy and thought the case against him was terrible. But they couldn't take the risk that if the University of Colorado went to a bowl. Right, they could take everything away from them. And so, as a result of 19.8, he sided with the NCAA.

Molly Bloom: Yeah.

Willy Walker: 1955?

Molly Bloom: 1955 is a federal statute running an illegal gambling business. Now, the interesting thing about 1955 is it is supposed to be only used to indict people who run games of chance. Blackjack, roulette. You know, there's a little skill, but not really. I mean, it's a roll of the dice, the turn of the hand. While poker, you could make a really strong argument is a game of skill. People are playing each other. The pros that are winning the World Series are generally there at the final table every year. And so, for years, for decades, poker was never included in this charge. Right before I got indicted, the government challenged a case in the Eastern District of New York. A new precedent was set. And so here we are.

Willy Walker: So, you've got the case coming in against you by the Feds and you go get Jim Walden, who at that time was at Gibson Dunn, to be your lawyer. Although the name actor and all that and the movie is Aaron Sorkinized not exactly the way it was. You did go get one of the very best lawyers in the country to defend you and Jim took you on basically out of the goodness of his heart. One of the things I thought in doing a little bit of research on Jim that was so interesting is that Jim also represented Grigory Rodchenkov, who's the guy who called the Russians on their doping. And if any of you watched the movie Icarus, Icarus is all about Grigory and Jim was his attorney, which I thought was fascinating. But you say, Molly, that your mom cries every time that she hears Jim Walden's name mentioned because she just thinks the world of him. Talk for a moment about why Jim was so good as your attorney.

Molly Bloom: You know, it was interesting because after they set the new precedent, what happened was the government seized my assets. So, I talk about logging in to my bank account and seeing a balance of negative $9 million. And I go back home, I move in with my mom thinking it's all over and I'm trying to put my life back together in the mountains of Colorado. It was two years later that the government sent 17 FBI agents with machine guns and arrested me. They'd been building a case against me, and it was as big of a shock to me as anything in my life because I hadn't run a game for two years and my attorney said, if you want her, she's here, just tell us. We'll come in. So, at this point, I'm living in a you know, you have a day and a half to get to New York City. I'm having a hard time grasping the reality, you know, and I'm in this arraignment with a whole slew of really serious Russian organized crime individuals who are sitting in the audience on this side, and their wives and girlfriends are sitting on their side. And I'm just like, what is happening in my life? And my mom's there. And we're both just shell shocked. And we have eight meetings with attorneys. Seven out of eight of them said, if you don't have a retainer, which I didn't, I didn't have a cent. Government took all my money. My mom puts up her house to bail me out of jail. We're not going to represent you. And Jim Walden met with us and said, “You need a chance. You need a shot. And I'm going to go to Gibson and I'm going to say, look, we'll figure out the money.” I started working with Jim and I remember going into his office and saying, “Okay, Walden. What's our strategy and what's our angle?” (Laughs) Tough girl gambling background. And he's like, “Molly, integrity is going to be our strategy and our angle.” And it was that simple to him. That's who he is, and he is the human being that in my most vulnerable time, probably my most moldable time brought me back home and made me remember who I wanted to be no matter what. And having someone like Jim fight for you and instruct you and influence you in that way was so incredible and instrumental. And I just knew this is who I wanted to be, I wanted to be Jim Walden. I made this deal with myself. Never again. My soul will never be for sale again. It will be these principles and these morals that I follow, that I cling to, I will conduct myself with integrity no matter what. And that's why a couple of weeks later, when the prosecutors wanted that meeting and they didn't care about the mobsters and they didn't care about the gangsters, which, I had run-ins with that was scary and terrible and everything. They wanted me to wear a wire and try to get information from the politicians, from the billionaires, from the celebrities on things like: are they betting sport? You know, like things that I didn't really believe in my heart of hearts were creating harm in society. So, their deal was, we'll give you all your money back. We'll give you a deferred prosecution, but you need to help us take down these people. And, it didn't, it didn't feel right. You know, and it felt like the position I was in was 100% my fault. Nobody tried to trick me into it. It wasn't like I didn't understand how things worked and it wasn't like I didn't have a lot of opportunities. I have a great family. I had tons of opportunities and so I just knew in my heart that I had to stand for the consequences of my own actions. And I was terrified of the outcome. Terrified of jail. Terrified of not ever having money again. But you know. I just knew that I had to make that choice.

Willy Walker: Was it that time that you decided you'd also give up and go dry? Where was it that of you focusing on your own personal health that came into that? Was it in that moment of clarity as it relates to your ethics and what you would and wouldn't do as it relates to the Justice Department? Or was it before that?

Molly Bloom: No. There were a couple of times. And it's something that I consistently sort of look at and evaluate. When I was running the games in New York, when I started to become this person that prioritized money and greed over integrity and started to make these choices. I started to use a lot of substances. At first it was just to be able to stay up and everything and brought for the games was like Adderall. And then I started to drink a lot and I started to not like myself as much. And, you know, it's just this whole thing. And so when the Feds seized my assets. I got sober. I needed to be clear. And I also at that time really had a problem. After I had fixed my life completely, from the outside. Then I got sober again. And that's a different sort of there's a different genesis or different reason for that. Basically, getting sober, what it meant to me was no more crutches. You have to face the full weight of your reality, of the things that you've done, of who you've been. Of how you need to change. Of the consequences of living this way. You have to face it fully, no out. And that was basically the reason for getting sober.

Willy Walker: So you write the book and then you get Aaron Sorkin, who has said previously when you went to meet with him and you worked really hard to get the meeting with Aaron, I have to say, and one of the things that's really evident, Molly, is you have an incredible ability to identify talent. And when you identify what you want, you go after with unrelenting effort and focus. And so, you know, you went around Hollywood trying to find someone to make your movie, but you kept saying, Aaron Sorkin's a person that I need to meet with. And you finally got your meeting with him, and you finally convinced him to do it. He turned it into an incredible movie. But as you say, you went from walking down the red carpet to a jail cell, to walking on the red carpet at the Oscars. I mean, what an incredible turn of events over a very short period of time from facing real jail time to having an understanding judge who didn't sentence you to any time in prison, to then turning around and having your story made into a movie that was a wild success.

Molly Bloom: Yeah. You know, after sentencing, I of course, when he said that he wasn’t going to sentence me to jail, like I lost my feet, like it's impossible to articulate how terrifying it is to anticipate losing your freedom. And when I didn't have to go to prison, I was incredibly, incredibly relieved. But then there was this moment a couple days, weeks later. I'm 35 years old. I'm millions of dollars in debt. I'm a convicted felon. I'm a social pariah. I have the tabloids telling this tale. Nobody wants to take my phone call. My network is decimated. And I can't stay here. You know I can't stay this ruined, like I don't want to miss life. I don't want to miss having a family. I don't want to miss it and so I had to get really strategic. And I thought, okay, there's a story here, but there was a lot to navigate. The publishers only wanted this incredible take on celebrity takedown piece, which I wasn't willing to write. So, I wrote a book and got a small book deal with it, and it didn't move the needle. And then I got to Hollywood and people loved the story, but they were all so terrified of the billionaires, the A-list celebrities, the politicians who were trying as hard as they could to bury the story. And so, I had to just get really strategic. And what I did is I made this short list of people in Hollywood who don't have to play politics. It's the Spielberg. It's Shonda Rhimes. It's Aaron Sorkin. And Aaron has always been my favorite writer. And so, I just wanted my shot with him. I just wanted to have a shot. And thankfully, luckily he wrote the movie, and it did well. And I got that second chance.

Willy Walker: Very much so. So now you do a lot of speaking, as I said at the top, you run around and as Aaron Sorkin says, having listened to you, “she gives the audience the goosebumps experience.” And when you speak to groups, you talk about the playbook. What's Molly's playbook as it relates to what you learned from your career. And quite honestly, I was thinking about how you built a multimillion-dollar business as a sole practitioner. No marketing, no CRM system. You barely didn't even have a bank account. I mean, you want to talk about a unicorn business. You almost didn't even have a bank account and you built a multibillion-dollar business. But what's the Molly playbook as it relates to takeaways on how people ought to think about their careers?

Molly Bloom: The first thing that I talk about is when I was 12 years old, and I got that diagnosis of scoliosis and the doctors told me that my ski career was over. It was the first time in my life that I realized that I have to take responsibility for my own life, and I have to figure out how to be my own champion, my own coach, and to believe in myself. Because if I'm going to wait around for the world to believe in me or give me permission, it's never going to happen. So, it was cultivating that sort of belief in myself, then it's a growth mindset. It's believing that with the right amount of effort and optimism and ability to stay uncomfortable in the learning process, that you can change your intelligence, your abilities, the outcomes of your life. Starting to understand how to build real relationships. I'm not where I am right now without relationships and learning how to cultivate those authentic relationships. Learning how people work, being able to put what you need to the side to focus on the humanity of it all is super important. Being able to manage your own mind — this is for me the biggest. All those times where I felt like I was finished, I had to have this agency over my mind to shift out of the narrative, to shift out of that negative mindset and into something else. And for that reason, a meditation practice, I think, is the most profound productivity, resilience, powerful practice a person can have because it teaches you how to start observing the noise. Observing negativity, observing fear, observing doubt, and sitting above it and then being able to exert that agency to choose a different way to pivot, to get back in the game, you know? And so, like this ability to manage your own mind, manage your emotions, it's just huge. Finding the right people. It's in everything. I had to have this like cervical fusion and I'm applying to Hopkins, to be like the guy that does the NFL, because I don't want to mess around. And so, I just shoot for that level of partnership in everything that you do, I think makes a huge difference.

And then the last piece is that it is really hard to maintain high character in this world. It's not something that we should assume is a foregone conclusion. I think it takes work and I think it is the ultimate long game. And so, I have a practice that I instituted after this whole thing where at the end of the day, I look at how I showed up, I look at who I want to be and how I showed up in the world. And that ranges from Did I procrastinate? Did I hit my goals? But it also is: Was I honest today? Was I completely selfish or was I trying to give of myself? And I just do this really quick checklist. And I find out what I need to work on. And I use that as a way to maintain integrity, and to keep my character on point. And that has been tremendously valuable and in the times that I wasn't doing it, tremendously harmful.

Willy Walker: So, at the end of one of the speeches that I watched, you were talking to people about creating a vision and what your future looks like and then executing on it. So, as you now look at this next chapter, what's Molly execute on next? Beyond being a great mom to Fiona.

Molly Bloom: Thank you. Yeah, I had a kid seven months ago, and that wasn't easy either. But it's not easy when she got here. But it's the most rewarding thing ever. I really believe in the power of gamification. I watched some of the world's most powerful, connected people who could do anything in the world, sit around and play cards with each other for thousands of hours. When you strip away the gamification, you have people just doing simple math with each other. And so, to wrap something in gamification and hold the attention of these people is so powerful. And so, my long-term plan is to figure out ways to use gamification to help kids learn things that are traditionally hard to learn, to help maybe adults learn about cognitive bias. That's always been my dream. And I'm getting to a point where I think I'm closer to being able to develop that. And so that's the long term. Short term, I have another book coming out. I have a Netflix documentary and a new podcast and an app that sort of connects people and helps to put into place a lot of these learnings.

Willy Walker: Anyone wants to hear more about Molly on gamification. Her most recent episode on the Torched webcast talks a lot about that. There's also a fascinating one in there on a poker player who was breaking the rules by somehow tapping into RFID technology.

Molly Bloom: It’s crazy!

Willy Walker: It's a fascinating story if anyone wants to listen to it. And then another one where she brings on her brother, Jeremy, to talk about the NCAA and Mills and how the world of sponsorship has changed so much. And it is I will tell you, Molly, just it's bittersweet to hear the price that Jeremy paid because of the old NCAA rules and then to see now the NCAA moving and changing, just like we're seeing organizations like the PGA have to change as well.

Molly Bloom: Yeah, I agree.

Willy Walker: You've been amazingly generous with your time. I hope you enjoy the rest of your time away from Denver, and I look forward to seeing you back home. My thanks again to our mutual friend Rick for putting the two of us in touch with each other.

Molly Bloom: Absolutely.

Willy Walker: And thank you so much for sharing today.

Molly Bloom: Thanks for a great conversation.

Willy Walker: It's been great. I'll see you soon. Thanks, everyone, for joining us today. Have a great day.

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