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All-In with Chamath, Jason, Sacks & Friedberg

Molly's Game Uncensored: The Truth Behind the World's Most Infamous Poker Game

26 Nov 2025

38 min duration
6757 words
5 speakers
26 Nov 2025
Description

(0:00) Molly Bloom joins the besties live in Las Vegas! (1:48) Did Jason actually play in "Molly's Game"? (3:23) Molly's background, starting the game, getting strong-armed by a famous actor, getting stiffed for $250K and losing the game (16:54) Moving the game to NYC, mob involvement, legal troubles, writing her memoir and making the movie (31:10) Best celebrity poker players, high-stakes poker archetypes, and more (34:31) Sales coaching advice Thanks to Oracle! Join Oracle AI Experience to discover how Oracle is your partner for accelerating your AI journey. https://www.oracle.com/artificial-intelligence/ai-experience/?source=:ex:sn:::::AllIn&SC=:ex:sn:::::AllIn&pcode= Follow Molly: https://x.com/ImMollyBloom Follow the besties: https://x.com/chamath https://x.com/Jason https://x.com/DavidSacks https://x.com/friedberg Follow on X: https://x.com/theallinpod Follow on Instagram: https://www.instagram.com/theallinpod Follow on TikTok: https://www.tiktok.com/@theallinpod Follow on LinkedIn: https://www.linkedin.com/company/allinpod Intro Music Credit: https://rb.gy/tppkzl https://x.com/yung_spielburg Intro Video Credit: https://x.com/TheZachEffect

Audio
Topics Discussed
Transcription

Chapter 1: What led Molly Bloom to start her infamous poker game?

0.031 - 24.621 Chamath Palihapitiya

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 high stakes 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.

0

24.601 - 47.723 Chamath Palihapitiya

We have a great conversation, tons of insider stories, who imploded in our LA game, the best celebrity poker players, getting shaken down by the mob, how she got an Aaron Sorkin 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.

0

47.703 - 67.584 Chamath Palihapitiya

Also, make sure you head over to our YouTube channel, a YouTube exclusive for the first ever Bestie Poker Freezeout game. Who's going to win? Chamath, Freebird, me, or some of the world's greatest poker players, Alan Keating and Jason Kuhn. Also, Phil Hellmuth. He wound up there as well somehow. So, happy Thanksgiving.

0

Chapter 2: How did celebrity involvement shape the dynamics of the game?

67.804 - 74.031 Chamath Palihapitiya

We love you. And be safe. And we'll see you all next week for a regular episode.

0

74.095 - 91.723 Jason Calacanis

Listen, we have a guest. We do have a guest. She's an entrepreneur, best-selling author, one of Fortune Magazine's most powerful women. I didn't know that. 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.

0

91.863 - 100.997 Jason Calacanis

But Molly's also, I think, got an amazing sense of what made her successful and the journey she's been through, I think, is a really interesting one to learn from. So please join me in welcoming Molly.

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107.002 - 114.178 Chamath Palihapitiya

Nice to see you, Molly. Molly, what was the origin of the game? We know some of our friends played in it.

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115.762 - 116.383 Jason Calacanis

Hold on a second.

Chapter 3: What challenges did Molly face while running her poker games?

116.463 - 135.02 Jason Calacanis

Jason, you claimed on our show, let me just read the notes. The notes? Yeah, there are notes here. What did I say now? So apparently, where's the thing that Jason said? We were on the show and Jason said he played in the game all the time and... No, no, no, no. What did you say? I said I was invited to the game. No, you did not say that. Lisa, please pull the tape.

0

135.521 - 145.217 Jason Calacanis

And when you're ready, just raise your hand and let me know exactly what Jason said. And then Molly responded on Twitter that you did not play in my f***ing game.

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145.618 - 147.842 Chamath Palihapitiya

Okay, let's be clear. Molly, did you invite me to the game?

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149.206 - 152.051 Molly Bloom

I don't remember inviting you to the game.

0

Chapter 4: How did the mob become involved in Molly's poker game?

152.071 - 159.122 Molly Bloom

But here's the deal. So there were two versions of the game. There was the version where I was working for someone who would send me a list.

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159.363 - 159.663 Jason Calacanis

Got it.

0

159.783 - 162.347 Molly Bloom

And I'm sure that you were probably on that list. I was a fish at the time.

0

162.388 - 166.354 Jason Calacanis

It was Jeffrey Epstein's list, right? Absolutely.

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166.79 - 167.451 Molly Bloom

Okay.

167.471 - 172.861 Chamath Palihapitiya

But when it was my game, you know... I just remember the Four Seasons. Yeah. Was that your game?

172.881 - 173.141 Molly Bloom

It was.

173.522 - 179.974 Chamath Palihapitiya

Okay, so it was the Four Seasons. I remember you invited me and you said, Toby's going to be there, Leo's going to be there, whatever, and they'd love to see you.

Chapter 5: What lessons did Molly learn from losing the game in LA?

180.094 - 203.068 Chamath Palihapitiya

And 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, friend of ours, we play poker with sometimes, was part of this. And then you decided to move it to New York.

0

203.088 - 208.255 Chamath Palihapitiya

Just let everybody know how this all got started for you and when you took over the game.

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208.454 - 236.385 Molly Bloom

Okay, so I was in college, skiing for the U.S. ski team, had an accident and retired and kind of didn't know who I was because sports were my identity. Went to L.A. simply because I wanted to be warm. I'd been cold since I was two years old and 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. Okay.

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236.365 - 249.382 Molly Bloom

And so I show up to this poker game, and, you know, it's 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.

0

Chapter 6: How did Molly rebuild her poker empire in New York?

249.402 - 273.657 Molly Bloom

And I get to be a fly on the wall in this incredibly compelling room. And also, you know, I'm 23 years old. This is access to information, to capital, to power. And then at the end of the night, They were tipping me in chips and someone counted out $4,000 in cash and I was like, okay, I don't know what's up with this chip token economy, but I think I might want in.

0

274.639 - 297.275 Molly Bloom

And over the next eight months, I started to learn to speak the language of poker. But really what I was focused on is how do I forge alliances? Because I knew that I would say about three 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. I mean, it really was a Trojan horse.

0

297.295 - 313.757 Molly Bloom

You could use it to infiltrate any subset of society. And I was learning about the world from some of the people who were actively involved in shaping culture. So it was a fascinating, interesting time, and it was also very lucrative.

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Chapter 7: What was the turning point that led to Molly's legal troubles?

314.311 - 336.521 Molly Bloom

And so I decided to start my own games, and I had eight months of notes of what I would do differently. And I think because I wasn't a poker player, there was an advantage, because I was able to zoom out and see this isn't just about poker, this is about community, it's about storytelling, it's about belonging to something, and it's about escapism and fantasy.

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336.861 - 356.832 Molly Bloom

And so I really started to build on those topics and those... I wanted everyone to come into this room and from the second they walked into this room, feel like they were in Monaco or in a James Bond movie. And so when I started the game, eight months later, You know, I was 24 years old.

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356.852 - 379.148 Molly Bloom

I didn't think these people who are rich and famous and we're going to come, let alone make it their their home game. And so I would say that started the about four and a half, five year tenure of the L.A. game. And when we started out, when I was serving drinks, it was a ten thousand dollar buy in. I raised it to a fifty thousand dollar buy in.

0

379.702 - 387.395 Chamath Palihapitiya

Yeah, that's the number I remember, and I was like, wow, those are high stakes. Because at the time, even in LA, people were not playing in those stakes.

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387.415 - 387.716 Molly Bloom

No, for sure.

387.736 - 388.978 Chamath Palihapitiya

And you really elevated the game.

Chapter 8: How did Molly's experiences influence her approach to sales and coaching?

389.619 - 396.571 Chamath Palihapitiya

Somehow, the mob got involved, and the game moved to New York. Fast forward to this, because this got pretty dark pretty quick.

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397.132 - 399.255 Molly Bloom

It did. So I lost the game in LA.

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399.736 - 401.639 Chamath Palihapitiya

How do you lose the game in LA?

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402.22 - 421.234 Molly Bloom

Well... One of the players who was making 10x what he was making in the poker game became very obsessed with this game and wanted to talk about it all the time, and then started to want to kind of do things that felt wrong.

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421.265 - 428.578 Chamath Palihapitiya

Okay. Okay. Like maybe target certain weak players, maybe get some of your tip money.

428.598 - 429.84 David Sacks

Like actively cheat the game?

430.821 - 436.852 Molly Bloom

Yeah. Angle shoot the game? Angle shoot. And also was complaining that I made too much money.

437.413 - 437.673 Chamath Palihapitiya

Got it.

438.895 - 460.805 Molly Bloom

And basically gave me this offer, I'll pay you a salary and you can work for me, you can be the figurehead. And I really wanted to keep the game. I was making millions of dollars legally. I was paying my taxes. I was, you know, like I had mentioned, it was incredibly exciting and educational. But I didn't want to be under, I didn't want to work for him.

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