Speaker 1
Hey everybody, the besties are taking Thanksgiving off. But hey, we didn't forget about you. We banked a couple of great content segments while we were in Vegas. First, here's an interview with Molly Bloom. You know, she ran the legendary highstakes game in LA in New York. I was invited to the LA one. We'll get into that. And her story was turned into the feature film and book Molly's Game. We have a great conversation, tons of insider stories, who imploded in her LA game, the best celebrity poker players, getting shaken down by the mob, how she got an Aaron Sorcin meeting, and much, much more. Big thank you to our friends at Oracle for partnering with us on this amazing VIP lunch we did in Vegas at the Venetian. What a great hotel. Also, make sure you head over to our YouTube channel. A YouTube exclusive for the first ever bestie poker freeze out game. Who's going to win? Chbahhat Freebert, me, or some of the world's greatest poker players, Alan Keading and Jason [ __ ] Also, Phil Helmouth. He he wound up there as well somehow. So, happy Thanksgiving. We love you and uh be safe and we'll see you all next week for a regular episode.
Listen, we have a guest.
Jason Calacanis
We do have a guest. She’s an entrepreneur, bestselling author, and one of Fortune magazine’s most powerful women.
Speaker 1
I didn’t know that.
Jason Calacanis
Molly Bloom ran the world’s most exclusive poker game. You probably know her from the movie Molly’s Game, which we’ll hear a little bit about today. Molly’s also got an amazing sense of what made her successful, and the journey she’s been through is a really interesting one to learn from. Please join me in welcoming Molly.
Thank you. All right, nice to see you, Molly. What was the origin of the game? We know some of our friends played in it.
Jason, you claimed on our show—let me just read the notes.
Speaker 1
The notes?
Jason Calacanis
Yeah, there are notes here. Apparently, we were on the show and Jason said he played in the game all the time.
No, no, no. I was invited to the game.
Speaker 1
No, you did not say that. Lisa, please pull the tape, and when you’re ready, just raise your hand and let me know exactly what Jason said. Molly responded on Twitter that you did not play in her game.
Jason Calacanis
Okay, let’s be clear. Molly, did you invite me to the game?
Molly Bloom
I don’t remember inviting you to the game, but here’s the deal: There were 2 versions of the game. There was the version where I was working for someone who would send me a list.
Jason Calacanis
Got it. And I’m sure that you were probably on that list when I—
Chamath Palihapitiya
Jeffrey Epstein’s list, right? He was young.
Molly Bloom
Absolutely.
Jason Calacanis
Okay.
Molly Bloom
But when it was my game—
Jason Calacanis
I just remember the Four Seasons. Was that your game?
Okay, so it was the Four Seasons. I remember you invited me and said, “Tobey’s going to be there, Leo’s going to be there,” whatever, and they’d love to see you. I said, “They would love to see me lose $50,000. There’s no way I’m going to this game,” because I was playing in a 5/10 game.
But you were working for somebody at the Viper Room. The game started, you then took it over, and it very quickly became a big game. Famously, Tobey Maguire, a friend of ours whom we sometimes play poker with, was part of this. Then you decided to move it to New York. Just let everybody know how this all got started for you and when you took over the game.
Molly Bloom
I was in college, training for the U.S. Ski Team, and had an accident and retired. I kind of didn’t know who I was because sports were my identity. I went to L.A. simply because I wanted to be warm. I’d been cold since I was 2 years old.
I ended up working for this guy. He had a real estate development company, and he said, “Tomorrow night, I need you to serve drinks at my poker game.”
So I showed up to this poker game, and it was A-list celebrities, like you’ve mentioned, but also the head of one of the biggest investment banks, a politician who was a household name, somebody from the tech world. I got to be a fly on the wall in this incredibly compelling room. I was 23 years old, and this was access to information, capital, and power.
At the end of the night, they were tipping me in chips, and someone counted out $4,000 in cash. I was like, “Okay, I don’t know what’s up with this chip-token economy, but I think I might want in.”
Over the next 8 months, I started to learn to speak the language of poker. What I was really focused on was, how do I forge alliances? About 3 months in, I knew I didn’t want to just serve drinks. I knew I wanted to have my own games. This was an incredible opportunity. It really was a Trojan horse—you could use it to infiltrate any subset of society.
I was learning about the world from some of the people who were actively involved in shaping culture. It was a fascinating and interesting time, and it was also very lucrative. I decided to start my own games, and I had 8 months of notes on what I would do differently.
I think because I wasn’t a poker player, there was an advantage. I was able to zoom out and see that this isn’t just about poker. This is about community, storytelling, belonging to something, escapism, and fantasy. I wanted everyone to come into this room and, from the second they walked in, feel like they were in Monaco or in a James Bond movie.
When I started the game 8 months later, I was 24 years old. I didn’t think these people who were rich and famous were going to come, let alone make it their home game. I would say that started the 4.5- to 5-year tenure of the L.A. game.
When we started out, when I was serving drinks, it was a $10,000 buy-in. I raised it to a $50,000 buy-in.
Jason Calacanis
That’s the number I remember. I was like, “Wow, those are high stakes,” because at the time, even in L.A., people were not playing for those stakes. You really elevated the game.
Somehow the mob got involved, and the game moved to New York. Fast-forward through this, because it got pretty dark pretty quickly.
Molly Bloom
It did. I lost the game in L.A.
Jason Calacanis
How do you lose the game in L.A.?
Molly Bloom
One of the players, who was making 10 times what he was making in the poker game, became very obsessed with the game. He wanted to talk about it all the time and started wanting to do things that felt wrong.
Jason Calacanis
Like maybe target certain weak players, maybe get some of your tip money—
Molly Bloom
Like actively cheat the game.
Jason Calacanis
Angle-shoot the game.
Molly Bloom
Angle-shoot. He was also complaining that I made too much money.
He basically gave me this offer: “I’ll pay you a salary, and you can work for me. You can be the figurehead.”
I really wanted to keep the game. I was making millions of dollars legally. I was paying my taxes. As I had mentioned, it was incredibly exciting and educational. But I didn’t want to work for him.
Jason Calacanis
Right. There’s a power imbalance because this person theoretically might have been famous, and the players might follow him if he boxed you out.
Molly Bloom
He said, “It turns out they want to play at a movie star’s house.”
Jason Calacanis
They wanted to what?
Molly Bloom
Play at a movie star’s house.
Jason Calacanis
Got it. Is it well known who that person is?
Molly Bloom
It’s well speculated.
Speaker 1
She never says who.
Jason Calacanis
Who they speculated?
Speaker 1
Tobey Maguire.
Jason Calacanis
Uh-huh.
Molly Bloom
The concept was also that there was this device called a Shuffle Master, which was used in the first iteration. It makes the game go much faster. 3 people—myself, Tobey, and another person—had a Shuffle Master in Los Angeles because you could theoretically buy them from somebody in Vegas, but they weren’t available.
Chamath remembers because he got an early one, and I used to bring mine to Chamath’s game. He’d say, “Hey, can you bring the Shuffle Master?”
Jason Calacanis
He also angle-shot you and wanted you to rent a Shuffle Master.
Speaker 1
I’ll never forget going to his house.
Jason Calacanis
No, he was talking about Tobey, not me.
Speaker 1
Not you. Not you.
Molly Bloom
I’ll never forget. He was right about the Shuffle Master.
Jason Calacanis
Renting out a Shuffle Master. I mean, he had a tough couple of years. You said it was a pretty big downdraft.
Molly Bloom
Shuffle Masters cost $17,000 at the time. Yeah. Um, and he was right that we needed one. Uh, and so he said, “Well, how about we'll use mine? Just come up to my house and get it, right?” So, go to his house and get it. And then I brought it back and he said, “Um, I'm going to need $200 for this.” I'm like, “You're you're kidding, right?” Like, I'm sitting there looking at his mansion, you know, 200 a shot. I mean, and about 5 months in, I'm like, “We need to buy our own shuffle master, right?”
Jason Calacanis
Yeah, they could be obtained. So, Tobey took the game away from you, and you were like, “I’m moving to New York and restarting the game there.”
Molly Bloom
I was really pissed.
Jason Calacanis
It was 2008.
Molly Bloom
Yeah, I was like, “I’m going to build the biggest poker game in the world.”
Jason Calacanis
Can you talk a little bit about how you did that, with respect to salesmanship and building confidence to grow that game? You moved to a new city and didn’t know anyone.
Speaker 1
How do you convince them, and maybe talk a little bit about what you learned early on about sales and earning people’s trust and how you got that to happen?
Molly Bloom
Yeah. So what I focused on much earlier, before I eventually realized that if you’re treating the business—if you’re treating the poker game like a business—essentially, what you want is 9 people seated around a table with equal playing styles, equal skill levels, and hopefully you get these heart-pumping results. But at the end of the year, the money changes hands and the house wins.
But before I realized that, what I had was—I was raised by parents who believed in teaching lessons all the time. My dad’s lessons were excellence and discipline and overcoming fear. My mom’s were integrity, integrity, integrity; what can you do for the world? And don’t make people feel like they’re transactions.
That’s the education that I had. I was a really hard worker, and I held myself to a high standard. For instance, when I started running these games, there were a lot of pros who would offer me freerolls—straight cash if they could play—but I knew that would compromise the integrity of the game.
So what I did was, I didn’t take shortcuts. I was trustworthy, I invested in people, and I developed relationships. I was very intentional about not asking them for favors before I walked in, because everyone in the world was asking them for favors. Instead of “What can you do for me?” it was, “What can I do for you?”
Over time, I think people sense that you’re a trustworthy person and that you’re deeply invested in their outcome. I think that was focusing on that relational capital, cultivating that trust, and being a part of someone’s life—doing events, expanding the time that you spend together outside of just poker, and doing events with the whole crew.
That’s what I focused on, and it was so incredibly valuable.
Speaker 1
A big part of this culture at the time, unlike, say, some other games where we have a group of friends and it’s a high-trust environment and we settle up yearly, was that the tradition in L.A., at least in the ones I played in, was you settled up the next day. That would be your responsibility, I assume, or one of your runners, to go collect checks and settle with people.
Sometimes people maybe couldn’t settle, and it could get a little bit awkward. So maybe you could tell us about that part of the job that people don’t see, which is, hey, you’ve got to go the next day. Somebody lost $50,000 or $250,000. What was the biggest loss that you had to go collect? What was that like?
Molly Bloom
A couple things. First of all, what shocked me was that if you looked at the net worth of a lot of these people who were playing, it would indicate that a loss of a couple hundred thousand or even $1 million wasn’t a big deal, right? But that wasn’t the case. I saw crazy behavior.
I always asked myself the question, “What’s underneath this? What’s causing this flipping of the table, screaming at me that you’re never going to pay, whatever?” What I got to was that it’s fear. Even though it doesn’t make logical sense compared to someone’s net worth, losing money, or losing in general, triggers this fear response. You feel out of control.
My job consistently was having enough top-down control to be the one who could then make that person feel safe, because I saw in other games that the game runner was on the hook for the money. This person is saying, “I’m never going to pay you.” Then they’re both in fear, they get into a sparring match, the games end, and things fall apart.
It was really useful for me to be able to emotionally regulate myself, understand what was going on, talk them down from a ledge, and get them to pay, because if somebody stiffs the game, you could break the game permanently.
Speaker 2
Well, I’ve been stiffed, and I wrote those checks.
Speaker 1
Really? What’s the biggest you got stiffed for?
Speaker 2
$250,000.
Speaker 1
$250,000. And the person could afford to pay it?
Speaker 2
For sure.
Speaker 1
And they stiffed you, and then you’ve got to come out of pocket for that and make good.
Speaker 2
Yeah.
Speaker 1
Yeah. That’s hard.
Speaker 2
Yeah, but it teaches you to do a really good job on the vetting.
Molly Bloom
Yes. I mean, I had bank employees on my payroll, basically, because in L.A. people drive a Lamborghini, they rent a house in the Valley, right?
Speaker 1
Yeah. So, Molly, can you just talk about what you talked about earlier with us when we were playing poker or during lunch? Someone said, “What sort of stuff are you into?”
Molly Bloom
Yeah. And I said, “I’m really into adrenaline stuff, like adrenaline sports.” I’m a competitive skier and so on. But this feels like that sort of high-stakes environment that you put yourself in. Where did that come from? And do you think you selected yourself into this environment because it feels like heli-skiing?
I think, first of all, I come from a really competitive family. One brother went to the Olympics twice and was a world champion in mogul skiing at 16. Then, after the Turin Olympics, he got drafted in the 5th round of the Philadelphia Eagles. He was an Abercrombie model, then he started and sold a tech company at literally the highest valuation, down to the second, I think. And now he’s CEO of the X Games.
My other brother is a Harvard-educated cardiothoracic surgeon at Mass General.
Speaker 1
Which one do your parents love most?
Molly Bloom
Well, they loved them more, but then Kevin Costner played my dad in the movie, so I instantly became the favorite kid.
Speaker 1
So they eventually loved you.
Molly Bloom
Eventually, but it took a lot.
Speaker 1
It did. Yeah.
Molly Bloom
That was part of it. We grew up skiing, and my dad was really insistent that fear was not going to sideline you. From an early age, some kids get grounded for talking back or whatever. We got in trouble for letting fear get in the way.
Something started to happen in those early years where it was this very exciting experience to look at something, be afraid of it, and then do it—like running a big game where people go south for $250,000 and then you decide, hey, I’m going to do it. But that was the behavior you were trained on early on. I think it was a byproduct of looking fear in the face and jumping into it.
Speaker 1
Yeah. And that’s a pretty great feeling, right?
Molly Bloom
Totally, and a bit of pride. You wanted to restart the game, and so you had that pride.
Speaker 1
Big-time pride. So take us to the game moving to New York, the mob getting involved, you getting beat up, getting pinched, and this whole thing going sideways.
Molly Bloom
Okay. So I moved to New York. To your question, I really started interviewing poker players: What was the problem with the current system? There were really well-established games and whatever, and what I found was that there was a problem with trust.
A lot of times, game runners would play in their own games. If they had a bad night, the rake would be higher. I wasn’t taking a rake. Then I realized, okay, well, if I can become the bank for these games and settle, and then provide this experience in which you could sit down next to your hero, or sit next to somebody who’s going to change your life in business, and there are no pros and it’s all action, this is how I’m going to do it.
So I became the bank for these games. The game in New York was a $250,000 buy-in. It was 2008, and I remember the first game: the president was in the background on the television, giving the State of the Union on the economy, and there was $10 million on the table.
These were insane games. They were playing insane variations of poker.
Speaker 1
And you love the thrill. You feel the thrill.
Molly Bloom
I did. Yeah. I mean, this was the game where, ultimately, someone lost $100 million. So, yeah, that definitely made noise.
I told my parents, “Listen,” because they were like, “Please go back to school. Please finish your degree.” I knew what I was doing. I was like, “Okay, but I just have to do this thing real fast.”
So I decided I was going to go as big as I possibly could. Then I started smaller games, and it got out of control. Some of these guys from Brighton Beach started playing. I had them vetted, and their stories checked out, but I knew something was off. It was really off.
They were running the biggest insurance-fraud scheme in New York City history. They had alleged ties to the Russian mob. My only involvement with them was that they played in my poker game.
The next thing that happened was that the Italian mob—or impersonators of the Italian mob—came to me and said, “We want a piece of your game,” and I turned them down. They didn’t just go away. They sent someone to my apartment. This guy broke into my apartment, put a gun in my mouth, and—
Speaker 1
Jesus.
Molly Bloom
He told me that I worked for them and that, if I told anyone—law enforcement or anybody—they had found out where my family lived in Colorado. Then he beat the hell out of me and forced me to take everything out of my safe.
There was money and a gold bar in there for some reason, but also things that my grandmother, whom I was named after, had left for me.
It was just terrifying. I was completely terrified and ashamed of what I was now implicating my family in. I couldn't call anyone.
Speaker 1
Wow.
Molly Bloom
I kept waiting for their call.
Speaker 1
Did you think at that moment, “You know what? Okay, done”?
Molly Bloom
Yeah, but I didn't know if it was an option anymore because they were looking at me as a big earner now. They said, “This is a warning. It's not up to you anymore.”
Speaker 1
Wow.
Molly Bloom
So I didn't know what to do.
Speaker 1
Could you confide in anyone?
Molly Bloom
I didn't tell a single soul.
Speaker 1
You didn't tell anyone? You kept that all in?
Molly Bloom
Yeah. I was in my apartment, and I couldn't go outside because it was very clear I'd been assaulted. I was confused as to why I wasn't hearing from them, because about 3 or 4 days went by and I didn't hear anything. Then 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.” I never heard from them again.
Speaker 1
Wow. Dodging a bullet. My God.
Oh my God. But, yeah, but then—
Molly Bloom
Oh my gosh. Then the bullet of me came into play, and I started getting out of control. Like I said, integrity was important to me, but over time I was making these little decisions that were just a little left or right of where I stood. Greed and money became everything, and I started doing things that my attorneys told me not to do.
Speaker 1
Raking the game.
Molly Bloom
Yeah. Taking a rake.
Speaker 1
Taking a rake. Now, for people who don't know, if you have a home game and you collect tips, it's kind of a gray zone, but generally speaking, people don't have a problem with it legally. But in the casino business, the legal gaming business, they feel that's their business: to take a rake. They went through the proper channels to get a license to do that, and you can't do that at a home game, right? So now you're breaking the law to make extra money.
Sorry, just to be clear, a rake just means when you put money in the pot, they take a little bit of it out, put it on the side, and keep it for themselves. In the casino, they do an hourly rake, right?
Molly Bloom
Yeah, that's a rake, too.
Speaker 1
That's a rake, too.
Molly Bloom
Yeah. Yeah.
Speaker 1
Different. You were taking money out of the pots and keeping it for yourself.
Molly Bloom
So basically what I was doing was, I had become much more lenient about who I was letting into the game, so my exposure was getting bigger. In some of those games where I was betting on the players and they were bad bets, I started to take a rake. This was during the last 6 months. The feds had put a confidential informant in the game because they were listening to the Russians' phone.
Who tracked that? And then a couple of months later I got a text message from one of the dealers saying, “Don't come here. The FBI is here looking for you.” Finally, I knew it was game over, and I just wanted to go home, even though I'd pushed my family really far away. I just wanted to go home, so I tried to book a plane ticket from JFK to Denver. My credit card got declined, then my next card got declined, and I logged into my bank account and it read 99,999,000.
Jason Calacanis
The Division of Asset Forfeiture had taken everything because your property, unlike your personhood, doesn't have the presumption of innocence—except maybe in Florida. I'm not up on asset forfeiture. Now you're pinched: you get shaken down by the mob, then you get pinched by the feds.
Molly Bloom
My lawyers called and said, “You know, she can sue us because this is on the civil side, but anything she says will also be counted as a confession.” They said, “Do you want her? Are you pursuing any criminal charges?” They said no, so I could try to get my money back.
I moved in with my mom. I felt really sorry for myself, and it took me about 2 years to put my life back together. Finally, I got this little job in Los Angeles, moved back into this little studio apartment, and thought, “Okay, it's a fresh start.” Five days later, in the middle of the night, 17 FBI agents with machine guns and high-beam flashlights put me in handcuffs and shackles. They put this piece of paper in front of me that said, “The United States of America versus Molly Bloom.”
Jason Calacanis
Wow. Wow. What a year.
Molly Bloom
I was really running hot.
Jason Calacanis
Yeah. Wow.
Molly Bloom
A couple of bad beats. I had a day and a half to get to New York City to find an attorney.
Jason Calacanis
And you're broke.
Molly Bloom
And I didn't have a penny.
Jason Calacanis
Yeah. Wow. How does it all resolve? How does the story resolve?
Molly Bloom
I found someone honorable and great to represent me. I didn't have money to fight it, so I pled out. The prosecutors wanted a meeting with me. This was the Southern District, and they really wanted me to become a CI. They weren't interested in the Russians or the Italians; they were interested in the billionaires, the politicians, and the celebrities.
Jason Calacanis
Who were there for poker, specifically?
Molly Bloom
Yeah. Let me be really clear: there was no Epstein in my game.
Jason Calacanis
Right.
Molly Bloom
So they said—
Jason Calacanis
They wanted you to be a rat against rich people, politicians, and famous people.
Molly Bloom
Yes.
Jason Calacanis
What did they think you were going to overhear? Murder plots? What were you going to be able to tell them?
Molly Bloom
Business deals. I could have given them leads for all kinds of stuff.
Jason Calacanis
Yeah. Crime—
Molly Bloom
For sure.
Jason Calacanis
Was this Preet Bharara, who was running the Southern District? He's also famous for getting rid of online poker.
Molly Bloom
He's a pretty by-the-books guy, for sure.
Jason Calacanis
Yeah. The Southern District, of all districts, is known for being the most hardcore, politically ambitious, and—
Molly Bloom
Sure. Right.
Jason Calacanis
So, did you go to jail?
Molly Bloom
I didn't. They said, “If you're willing to work with us, we'll give you all your money back and we'll give you a deferred prosecution, which will keep you out of prison.” I had about 48 hours to make this call. Where I got to was that this was my fault. I had near-perfect information about the laws. I had all these opportunities, I had loyal clientele, and I found this loophole. I was the one who decided to make this choice.
To turn around and drag these people who had families through this shit, based on my own bad decisions, just didn't feel like something I wanted to live with. So I turned down that offer and waited to get sentenced. We all thought I was going to prison, and I got a judge who was very disappointed in my life choices, but basically said, “You had a life before this.” I had character letters from professors and ski coaches, and I had a lot of people show up for me who had made better decisions than I had made in life. He fined me a lot, but I didn't go to prison.
But then I was 35 years old, millions of dollars in debt, and a convicted felon. The tabloids were telling this really reductive tale. How do you come back from that?
I decided there was a story here, and if I could monetize that, maybe it could address the reputational harm and the financial harm. I mean, I was millions of dollars in debt. So I wrote a book and waited for my life to change. Then I think 10 people read it, and probably 8 of them were related to me.
But it was still my only idea, and I still believed in it in my gut. I made a short list of the most successful filmmakers in Hollywood and thought, “Why not? Why not just go for it?” They needed to be brave because there were also a ton of people, as you can imagine—
Jason Calacanis
Yes.
Molly Bloom
Even though I'd fallen on the sword legally, and even though I hadn't implicated people in the book, they didn't want exposure, and I get that. Aaron Sorkin wrote A Few Good Men, The Social Network, and Moneyball. He was my favorite writer and also the highest-paid screenwriter at the time, which, if you're gambling—which we always are, right?—is a good bet.
Anyway, getting to him wasn't easy. I finally got to him, and I remember, before I walked in, thinking, “What am I doing? Millions of dollars in debt. My book sold 10 copies. I live with my mom, and this is the highest-paid screenwriter in the world.”
Jason Calacanis
So you got a meeting with him.
Molly Bloom
I did.
Jason Calacanis
And he had—had you sent him the book, obviously?
Molly Bloom
It was somebody that I bothered relentlessly.
Jason Calacanis
Right. So, to put the sales hat on again, you were relentlessly pursuing the sale.
Molly Bloom
Yeah.
Jason Calacanis
You were all over this guy, even though—
Molly Bloom
Yeah.
Jason Calacanis
—even though you weren't making any money, you just kept going.
Molly Bloom
Yeah. I had met with other screenwriters, and they were kind of a big deal, and I was like, “No, no, no.” My brother said, “You can't keep passing. You live with your mom.”
Jason Calacanis
What did you say when you got in the room?
Molly Bloom
I told him my story, and I think my legs were shaking, but I had this game face on. When I was done, he said, “Well, I'll tell you one thing, kid. I've never met someone so down on their luck and so full of themselves.”
Jason Calacanis
Wow. It's a good character study.
Molly Bloom
Yeah. And then they made an offer.
Jason Calacanis
Yep.
And then they paid, and you used that money to pay down this fine you got?
Molly Bloom
I did. I just finally finished paying off the government last summer.
Jason Calacanis
Wow. Wow, congratulations. I guess, just to ask you the hard question, which you kind of answered: I was always wondering, how does one make the decision to write this tell-all book, and what was the fallout from that book? I remember in L.A. people talking about the book coming out. Everybody was really scared about it.
You didn't put people's names in it. You specifically chose to—
Molly Bloom
I put their names in it if they had talked about playing in the games.
Jason Calacanis
Right. So you took some steps there, but you did make a decision, with all these people who put you in business, to basically turn on them and tell their story. There was no nondisclosure agreement; you hadn't made any agreements not to talk about it.
Molly Bloom
Well, I didn't turn on them. I actually supported them at every turn.
Jason Calacanis
Well, I'm just saying—
Molly Bloom
I could have gotten a lot of money back and a deferred prosecution.
Jason Calacanis
Okay. Yes, in that case. Yeah.
Molly Bloom
And then the publishers were willing to pay me 6 or 7 figures for a celebrity hit piece. I was broke, living with my mom. Again, I turned that down. I chose to work with a screenwriter who was absolutely clear and willing to contract that we weren't ruining any lives.
Jason Calacanis
Got it. Great. And just so you know, everybody in the poker games—all the dealers, everybody involved—had to sign nondisclosure agreements.
Molly Bloom
Probably smart.
Jason Calacanis
Probably smart, yeah. Do you still need to face fear in the face to feel like you're doing what you want to do?
Molly Bloom
Yeah. I don't have this addiction to that anymore, but I will always choose courage over comfort. I pay a big interior price internally if I don't.
But it's not like this thing where I need that adrenaline hit to make me feel alive. I like it; I pick my spots now. I have a 3.5-year-old daughter, so I knew before I brought a kid into the world I needed to do a lot of work on myself.
Jason Calacanis
You learned a lot about yourself.
Jason Calacanis
I wonder what you could tell us about the nature of the men who are obsessed with playing this game at these stakes—the camaraderie, the competition, and the chaos. What have you learned about the nature of these men?
Molly Bloom
Well, again, I think there are a couple of different archetypes.
Jason Calacanis
Okay, tell us.
Molly Bloom
There are the ones who are on a self-destructive bullet train.
Jason Calacanis
So it's not just high-stakes poker, right?
Molly Bloom
Yeah. It's putting their marriages in bad places in very egregious ways. There's drugs. It's the hedonic treadmill gone crazy.
Jason Calacanis
Got it.
Molly Bloom
Then there are just the highly competitive people who are very comfortable with volatility—in fact, they prefer volatility and chaos—but still have some semblance of control over themselves. Then I think there are people who play because they love the game, because they like the aspects of it that make it an incredible game. They like the psychology. They like seeing the results of making high-level decisions with very limited information. They like the mental and social thrill of it, the camaraderie and the competitiveness.
Jason Calacanis
Who's the best celebrity poker player in all the years that you saw in these games? Who is the best?
Molly Bloom
Tobey Maguire.
Jason Calacanis
Yeah. And who is the second-best?
Molly Bloom
He wants you to say Chamath, but we were going to carve him out because he's not—
Look, I played with Tobey for 20 years. I would have said Tobey, too. I think he's exceptional.
Jason Calacanis
He's a grinder. He's tough.
Molly Bloom
Yeah, he's tough. He was the only one in the game who was tight. I guess second would be Ben Affleck.
Jason Calacanis
Yeah. Affleck's a good player.
Molly Bloom
Yeah. He's definitely smart. He definitely knows what he's doing. It depends on where he is in his life.
Jason Calacanis
Yes. Politician-wise, can you say or no?
Molly Bloom
I haven't named any of the politicians because they haven't been named.
Jason Calacanis
Yeah. Okay. Business people?
Molly Bloom
Once again, they haven't named themselves, so we'll leave them unnamed.
Jason Calacanis
And, Molly, you were telling us before that you do some kind of speaking work around sales. This is where I'm so interested. What are the things you tell people when you do those events? What is the big takeaway from your experience?
Molly Bloom
So, a lot of people—there's this small body of science called affective presence. It really focuses on what's going on subconsciously. If you work backward from core human fears—which I think is always a really good thing to do—after dying, being alone, and public speaking, what are people most afraid of? They're afraid of not belonging, not being worthy, people stealing money from them, and so on.
When you start to think about what kind of emotional footprint you're leaving with these people—how can I disarm them and also cultivate trust at the same time?—it takes a level of intentionality. A lot of us walk into a room thinking, "What's my résumé? What are my sound bites? What's my pitch?" instead of thinking, "How can I make this person feel like I'm with them, like this isn't a zero-sum game?"
There are just a couple of things that you can do. Listening is a huge one: listening with full presence, not listening while you're constructing your response, and asking open-ended questions. Go down this road with someone. Have some warmth about you and be affirming, but also be authentic.
And practice hard empathy. Easy empathy is with people you relate to, people who have a similar experience to you. Hard empathy is sitting down and having conversations with people whose views you don't like, whose personalities you don't particularly like, and trying to get to a place where you can understand them.
Jason Calacanis
Yeah.
Molly Bloom
Making that effort.
Jason Calacanis
Yeah.
Molly Bloom
Making that effort. It's interesting: humans hate uncertainty. Without an edited brain—and I mean edited by doing that work and meditation, whatever your mind-training tool is—the brain thinks that uncertainty is a metabolically unsustainable state, so it equates uncertainty with fear.
How can you start to give people that sense of certainty? Also, how can you become aware of it in yourself? If you know that you hate uncertainty, what you do is forage for some subjective truth and then cling to it. That's a big handicap.
To start to do the work of relaxing with uncertainty and being more curious, rather than needing to have this illusion of control—there are a lot of things that aren't so obvious or instinctual in the art of impact and connection.
It can also force you to let go of priors, which allows you to adapt and evolve. I mean, being able to adapt, being able to court change, and even reframing it as, "This is exciting" or "This is interesting."
What an incredible life you've had, ladies and gentlemen. Let's thank Molly for joining us. Thank you, Molly. And let's thank also Oracle. Thank you for hosting. Um, and my lord, we're going to have a great weekend. I'm going all in.