Molly Bloom, nicknamed the ‘Poker Princess’, is a former Olympic skier, and at 21 years old was ranked No. 3 in North America in moguls. After an accident, she left skiing and took a years sabbatical from the University of Colorado - Boulder to move to LA in 2004. Initially bartending, she began to run poker games in The Viper Room. These games attracted A-list celebrities such as Leonardo DiCaprio, Tobey Maguire, and Ben Affleck, playing for millions of dollars. In 2013, she was arrested for taking part in underground poker games and faced 10 years in prison, but was eventually sentenced to 1 year of probation. In 2014, she released her memoir ‘Molly’s Game’ which was made into an award winning film of the same name in 2017.



In this conversation Molly and Steven discuss topics, such as:


 How her upbringing was based around competition and achievement
 Why she was obsessed with achieving glory from a young age
  Moving to LA and finding her way into running poker games
  How she started running illegal poker games and made them different from others
  The psychological lessons she learned from watching poker games
  How she made herself indispensable to the game and its players
  What it took to run the world's most exclusive poker nights
  Having her poker game and income taken from her
  Learning to pivot quickly from failure to success
  Seeing someone lose $100 million in one night
  Kicking Dan Bilzerian out of her poker game
  How she was making $4-6 million a year from tips
  The mafia showing up at her door
  What she was able to learn from listening to the elite players of her game
  How she had access to the world’s most powerful people
  Becoming addicted to drinking and drugs
  Her legal troubles with the FBI and facing 10 years in prison
  Why she refused to snitch to the authorities for millions of dollars
  The lessons she has learned coming out of the world of poker
  Being comfortable with risk and the necessity of taking risks in life
  How she was able to sell her story into a Hollywood movie





You can purchase Molly’s memoir, ‘Molly’s Game’, here: https://bit.ly/3OvOLxq



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He put a gun in my mouth, beat the hell out of me, and he said, if you tell anyone about this, I know where your family lives.

For the first time in my life, I knew finally it was game over.

The former waitress who Took a small poker game, run out of a dingy nightclub.

For Hollywood celebrities to millionaires.

They literally made a Hollywood movie about it.

I had become the biggest game runner in New York City.

Leo DiCaprio, Ben Affleck, and Tobey Maguire, politicians, I was making $4 to $6 million a year.

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

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

This is where the science of how you make people feel became a really big tool And I would memorize people's lives the names of their kids what they cared about they were food order drink order these things can absolutely Be used for good But I just became obsessed What had been about trying to be an entrepreneur and be gutsy started to be exclusively about the money and the power.

I started to partner with people that were not the right people to partner with.

In the middle of the night, I get arrested by 17 FBI agents, machine guns.

They put me in handcuffs and they put this piece of paper in front of me that says the United States of America versus Molly Bloom.

They were going to give you millions if you snitched on the players in the game.

About 75% of people that listen to this podcast on audio platforms, Spotify and Apple, haven't yet hit the follow button.

If I could ask a favour from you, if you've ever enjoyed this podcast, please could you just go and hit that follow button on your app.

It helps the show more than I could possibly say.

And the bigger the show gets, the better the guests get.

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

I think it almost always starts with the family in childhood.

And I am from a family of, you know, my 2 little brothers are incredible humans, but like the craziest overachievers you could ever imagine.

And then I have these 2 incredible parents who were very powerful influences in our lives.

My dad stood on this platform of you cultivate discipline and if you have a fear, you walk through it and you learn how to suffer constructively for your dreams, for your goals.

And then my mom, she was this, she insisted on kindness and integrity.

So there's this whole ecosystem of extraordinary.

And I didn't know how I fit into that at all.

And I desperately wanted a seat at that table.

And probably during the times that we were raised, there are these ideas of what success looked like and how you get there.

And it was genius and talent and specific skillset.

But I knew that I had to be successful and this is not hyperbolic, I literally did not want to live.

I mean, I remember when I was applying to law school, I said to my dad, if I don't get into an Ivy League law school, I don't know like how, I don't wanna live, you know?

It's hard to know what you mean at 18 years old, But in my mind, you need clear proof and evidence that you are extraordinary by these accomplishments.

And my brothers had already started to make that happen.

Because 1 day at the dinner table, my dad said to me,

And then I started to kind of read books about the law and fiction a lot.

And then started to think about getting paid to argue for a living and all the glory that could come from that if you're fighting for justice or you're fighting to save somebody who's innocent, the sort of high points, the aspirational points of what it would be like to be a lawyer in a movie or a book.

Why do you think you cared so much about glory?

I don't think I cultivated much self-esteem.

And I don't think that I believed I was inherently worthy.

I believed that I had to achieve something big, huge, extraordinary, worldly, in order to then feel relief from that existential ache that followed me around my whole life.

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

I didn't even end up going at all or even finishing my last semester and a half at school because I just couldn't, I couldn't muster the energy and ambition it took to go do all these things.

And I think I was really questioning the conventionality of it all.

I ended up like not applying to law schools and just saying, I just need a year.

And the closest place that was warm on the ocean from Colorado in a straight line was California.

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

How did he receive this news that you were not coming to LA?

Not gonna financially support it Really disappointed so

you get here and he's he's no longer supporting you financially at all.

I mean, I got a job, I had to get a job the day I got here.

And I went to this restaurant in Beverly Hills, went to, you know, got a job for a couple days, it was terrible.

And then I went to this other restaurant and kind of lied and said, cause no 1 else was hiring in this Beverly Hills area.

And I lied and said that I had fine dining experience.

My boss said, you're the worst waitress we've ever seen and you've ruined like thousands of dollars of bottles of wine trying to open them.

He said, but you know, people seem to take to you and you're a hard worker.

So why don't you come work for our real estate development company as my executive assistant.

Oh, so it was the boss of the restaurant that offered you the job as the executive?

They had some real estate, they had some restaurants, they had a fund.

Yes, he came in the office 1 day and he said, and they're always zany things to sort of like thrown at me.

And he said, I need you to serve drinks at my poker game tomorrow night.

And I tell this story because it's just so indicative of the naivete and where I was, I remember Googling what kind of music do poker players like to listen to and what do they eat?

And then I proceeded to make this incredibly embarrassing playlist with songs like the gambler on it, you know, and got this cheese plate and showed up for this very fancy poker game in Hollywood with A-list celebrities.

And, you know, there's some names that of people that have already talked about being in the games and those are the names that I don't mind naming just to give context.

It was Ben Affleck and Tobey Maguire and Leo DiCaprio.

And then, you know, but apart from the actors, it was also the head of some of the biggest investment banks in the world, and the head of some of the biggest movie studios, and politicians who were household names, and people in the tech world that were about to take their companies public I mean it was It was unbelievable

Quite a few people have come out as you say and said that they were they played in those games

I was watching a video earlier even Dan Bozarian.

he played in those games Was was Were those games legal or illegal?

Legal, I, When I started running the games, I hired defense attorneys and had them analyze the federal statutes and to help me figure out a way to do it legally because in the early days, I wouldn't have done it illegally.

So you start as a, basically an assistant to the games that your boss is running.

And take me on the journey of what happens next.

Okay, so that first game, you know, I'm just shell shocked essentially, and also really mortified about the playlist and the cheese plate from Gelson's, you know?

Getting to be a, at 23 years old, getting to be a fly on the wall in this room where these conversations are open and candid and you are, I'm like you, I've always been fascinated in psychology.

I've always been an information data junkie.

And so this was as compelling as it could be.

And then I remember at the end of the night, because people were tipping with chips, it wasn't straight cash.

I remember making $3, 000 for refilling some drinks.

And so 2 things became really apparent to me.

1, this was incredible access to a network of people that I don't know if I would have ever had access to.

And to learn from people at this age of 23 when I didn't know who I was or who I wanted to be.

And number 2, that there was something that happened when there was a token or a chip, was the economic system that made people very liberal.

I'd hustle my butt off for a couple hundred dollars a night.

You know, all of a sudden the chip is involved and it's not real money.

I wanted to learn the rules of the game, the vernacular.

And then I started to try to figure out how do I stay in this room?

And this is where 1 of the places where effective presence became a really big tool.

Effective presence is the science of how you make people feel.

Everybody has their own emotional footprint that they leave on the world.

And there are really marked things you can do to have either positive or negative effective presence, or neutral, which is also not great.

So I remember talking to my mom and I remember saying, you don't even understand how compelling this is.

And I don't, I want to stay in this room more than anything, but I don't know how I could ever confer value in this room.

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

Like maybe they would just bring in another woman at some point to serve drinks.

Or, you know, I just, I didn't, I just didn't want to be disposable.

I wanted to find some reason to be, to be valuable in that room to, you know, and to be able to come back.

And I start, I was talking to my mom so much about everything that I hope to gain and where my mind was going with this opportunity.

And you know, I said to her, but mom, I have no idea how to bring value to this room.

And she said something that was really profound to me.

She said, maybe instead of thinking about all the things you want to get, you could think about what you could give.

And then she reminded me of that quote by Maya Angelou that everyone loves and loves to quote, which is people are going to forget what you said and what you did, but they're never going to forget the way you made them feel.

And I thought about that, and it's so true.

And I guess I had this suspicion that these people, with their power and their success and their access were different from the rest of us, that they believed that they were worthy, that they didn't harbor that secret fear that they weren't good enough.

And what I found unequivocally is that that wasn't true, and that many times someone at that level is even more convinced or needs even more validation.

And so I started to try to understand how to make people feel important, seen, heard, remembered, how to establish trust, how to establish authentic connection.

Because something that I realized by observing these games is that everybody wanted something from these people.

And so if I could figure out how to establish a real connection, there's emotional intelligence, which usually has a focus on the outcome, how to win friends and influence people.

Affective presence is more about being in the present with someone focused on the connection, not the outcome.

And this is truly what I focused on for the first 6 to 7 months is just creating a real connection with people, observing them and you know trying to train my mind to focus on what's unique about this person.

What's truly unique about this person and then getting to a point where you're vulnerable enough to say, God, I'm really fascinated by this thing that you do you know, whether it's at the poker table or in business or just in life and focusing in on the details and really getting outside of yourself and becoming curious and becoming a great listener, which by the way, you are an insanely great listener.

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

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

We think that the competitive advantages had in speaking, but if I've learned anything from doing this podcast, it's that to truly understand someone and then be able to, in this context, ask them a question, but in the world of business, to deliver them a solution to their problem, which is getting a sale, To create the upper hand, you simply have to listen.

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

And this is what the great thing of what I've learned from doing this podcast, but even from this conversation is, my next question is gonna be so much better for the fact that I listened to you.

I think we walk around armored with our egos.

And I think that true connection happens when somebody, when you're able to disarm somebody and they're able to disarm you and the egos slip away and it's just 2 people.

So when you go in and you start listing off your accomplishments and painting yourself as this, you know, all of a sudden it's like competition up, he goes up, and then there's not true connection.

You can't penetrate that kind of wall, can you?

both built 2 walls between yourselves because you're showing off.

When people hear that, they go, this idea of effective presence and understanding how to be kind of a different jigsaw shaped piece to each individual to get the best out of them or what you want from them, people will say, oh, manipulation, which the fine line between sales and persuasion and negotiation and manipulation, it's all there, you know.

So effective presence, EQ, active listening, all of these things that you learn can absolutely be used for good or they can be used for bad.

But I think something that is different about at least the brand of effective presence that I value is it's about your experience connecting with a human being.

It's not about, because I used to do that, right?

The way I used to do things is I would do all my research on you and I'd come in here with a few talking points so that I could instantly connect on something with you and show you that you and I are the same.

And I don't really do that anymore, although I don't hate that strategy.

But I think it just depends on how you use it.

I think when you use it in a manipulative way, I think it's easier to see.

Versus if you kind of take a few breaths before you go into a room and you say, this, what I wanna do here is to connect with someone, to have that human to human feeling, and to be of service in some way to a, in a greater way to humanity.

And by the way, that can also include yourself, you know?

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

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

And I'm like, I don't want to serve drinks in these rooms.

This was someone who felt powerless in the world.

If I could control these 9 seats, this thing that has so much control over these people that are so powerful, that was compelling.

I had this whole idea of how I would design the experience.

And also, I'd sort of learned in those 6 to 8 months that I was an entrepreneur, I was a problem solver, I could think on my feet, I had metacognition, I could feel a certain way inside, terrified, nervous, scared, and still act with composure.

These things that wouldn't quite present at a dinner table growing up with Jordan and Jeremy Bloom to culminate into an idea or You know sort of like that seat all of a sudden.

I just started to feel in my flow, you know and so but I was very loyal to my boss.

So I, you know, I just bided my time and I tried to figure out how I was gonna do this.

And then he made it quite simple for me because he called me and he said, you're focused too much on the game.

And by this point, I had really kind of gotten into, like I had started to think about how I was gonna build this game.

I was doing much more than just waitressing.

And I thought about it and I was like, I gotta take my shot.

Like this opportunity is too important for me.

So I had developed friendships and alliances.

And so I planned a game and I moved it to a really luxurious location.

And I hired a full staff of people and had them memorize everyone's favorite food order, drink order, the names of their kids, what they cared about in life, upgraded my playlist to a little Frank Sinatra maybe, I don't remember what it was, but it was better.

Moved out of this dungy basement, had it catered by the best restaurants in town, up, you know, like the best liquors, Cuban cigars.

I mean, I wanted people to walk into this room and feel like they were in Monaco or feel like they were James Bond for the night.

And I really, as the games were on, I really like got into the science of scent science and temperature and humidity and food and all these things that elicit the feel good chemicals.

And so, and then I invited everyone except for my boss.

And at the end of the night, The game went really late.

And then at 5 in the morning, I got this text message from my boss.

And I said to myself, he's gonna kill me.

I mean, I don't even know what's gonna happen right now.

Because he was a terrifying individual and very powerful.

And Just to give you some context, when I started working for him, I used to always say to him, I'm really worried about your soul.

And then later, when I got to know him better, I saw him with his family and he was very kind.

But he used to say to me all the time, you're gonna get trampled over.

And so anyway, so he walks into the room and he has this terrifying look on his face and he looks at me and he goes, I'm proud of you.

It was like graduation day for better or worse.

It's hard to know how to feel about that moment now sitting here decades later.

So from that moment, when you host that first game, you upgrade everything.

You upgrade the experience for your customers.

Eventually you set your sights on New York, but for a variety of different reasons.

And you move the games from being based in California and LA to being based in New York city.

See all The Diary Of A CEO with Steven Bartlett transcripts on Applepodcasts

How I Manipulated The World's Richest Men: “They Lost $100 Million In One Night!” - Molly Bloom (Molly's Game)