The episode features Molly Bloom, entrepreneur, best-selling author, and subject of the film Molly's Game, discussing her experience running the world's most exclusive poker games in Los Angeles and New York.

Bloom shares how she built games with $250,000 buy-ins featuring A-list celebrities, tech executives, politicians, and investment bankers, creating what she describes as a "Trojan horse" for accessing power and capital.

The conversation covers her journey from college ski team member to poker game operator, the mob threats she faced, her arrest by the FBI, and her decision to refuse cooperation deals that would have implicated wealthy clients.

Host Jason Calacanis clarifies he was invited to but never played in Bloom's game, while the group discusses the psychology of high-stakes players, sales lessons from her experience, and her eventual comeback through writing and film.

From Ski Team to LA Poker: Building the Game

Bloom retired from the U.S. ski team after an accident and moved to LA at 23, taking a job with a real estate developer who ran a poker game at the Viper Room

The initial game featured A-list celebrities, the head of a major investment bank, a household-name politician, and tech executives, with someone counting out $4,000 in cash as tips

"I knew I didn't want to work for this guy anymore. 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" - Molly

After eight months of taking notes, Bloom started her own game at 24 years old, raising the buy-in from $10,000 to $50,000 and focusing on creating an experience where players felt like they were "in Monaco"

The Toby Maguire Shuffle Master Incident

Toby Maguire allegedly angle-shot the game and eventually took it over by claiming players wanted to play at a movie star's house rather than with Bloom

Maguire purchased a Shuffle Master machine for $17,000, then charged Bloom $200 each time she borrowed it to speed up the game, despite his wealth and mansion

"He said, 'I'm going to need $200 for this.' And I'm like, you're kidding, right? Like, I'm sitting there looking at his mansion" - Jason, recounting Bloom's story

The loss of the LA game in 2008 motivated Bloom to move to New York with the goal of building "the biggest poker game in the world"

New York Game: $250K Buy-ins and $10M Tables

Bloom established herself in New York by interviewing poker players about problems in existing games, discovering trust issues with game runners who played in their own games

The New York game featured a $250,000 buy-in, and during the first game in 2008, there was $10 million on the table while the president gave the State of the Union address about the economy on TV in the background

"They were playing insane variations of the game that ultimately someone lost $100 million" - Molly, describing the scale of the New York games

Bloom became the bank for these games, settling debts and providing an experience with no professional players, focusing on action and access to influential people

Trust, Collections, and Absorbing Losses

Bloom refused free rolls and straight cash from professional players who wanted to play, knowing it would compromise the game's integrity and trust

"I didn't take shortcuts, I just was trustworthy. And I invested in people and I developed relationships... instead of what can you do for me, what can I do for you?" - Molly

Players would exhibit extreme emotional reactions to losses regardless of net worth, with Bloom realizing "it's fear" driving behavior like flipping tables and refusing to pay

Bloom absorbed a $250,000 loss when a player who could afford to pay stiffed the game, writing the check herself to maintain trust and prevent the game from breaking permanently

"I had bank employees on my payroll, basically, because in LA, people drive a Lamborghini, they rent a house in the valley" - Molly, explaining her vetting process

Russian Mob Threat and Armed Robbery

Players from Brighton Beach with alleged ties to the Russian mob joined the game, later revealed to be running "the biggest insurance fraud scheme in New York City history"

The Italian mob or impersonators demanded a piece of Bloom's game, and when she refused, they sent someone who broke into her apartment and put a gun in her mouth

"He told me that I work for them. And that if I told anyone, law enforcement or anybody, that they had found out where my family lives in Colorado. And then he beat the hell out of me" - Molly

The assailant forced Bloom to empty her safe, taking cash, a gold bar, and irreplaceable items from her deceased grandmother, while threatening her family in Colorado

Bloom couldn't leave her apartment due to visible assault injuries and told no one, until reading the New York Times cover story about 125 arrests in "the biggest mob-related takedown in New York City history"

FBI Arrest and Refusing to Cooperate

The FBI placed a confidential informant in Bloom's game after listening to the Russians' phones, and she received a text from a dealer warning her not to come because the FBI was looking for her

When Bloom tried to book a flight home to Denver, her credit cards were declined because "the division of asset forfeiture had taken everything" - property lacks presumption of innocence

After two years of rebuilding her life in LA, 17 FBI agents with machine guns and high-beam lights raided her apartment in the middle of the night, giving her a day and a half to find a New York attorney while broke

The Southern District prosecutors offered to return all her money and give her a deferred prosecution if she became a confidential informant against "the billionaires and the politicians and the celebrities"

"This was my fault. I had near perfect information on the laws. I had all these opportunities... And so to turn around and drag these people who had families through this bullshit based on my decisions" - Molly, explaining why she refused

Publishers offered Bloom six or seven figures for a "celebrity hit piece" while she was broke living with her mom, but she turned it down to protect her former clients

Sentencing, Book Deal, and Aaron Sorkin

The judge was very disappointed in Bloom's life choices but acknowledged her life before poker, with character letters from professors and ski coaches helping her avoid prison

At 35 years old, Bloom was millions of dollars in debt and a convicted felon, deciding to write a book to address "the reputational harm, the financial" damage

"I think 10 people read it, and probably like eight of them were related to me" - Molly, describing her book's initial reception before pursuing Hollywood

Bloom targeted Aaron Sorkin, writer of A few good men, The Social Network, and Moneyball, describing him as "my favorite writer and also the highest paid screenwriter at the time"

After relentlessly pursuing a meeting, Sorkin told Bloom: "I'll tell you one thing, kid. I've never met someone so down on their luck and so full of themselves"

Sorkin made an offer and the film Molly's Game was produced, with Bloom using the money to pay down her government fine, finally finishing payments last summer

Psychology of High-Stakes Players

Bloom identified three types of players: those on a "self-destructive bullet train" with drugs and destroyed marriages, highly competitive people comfortable with volatility who maintain control, and those who enjoy the psychology of making high-level decisions with limited information

"Toby" was identified as the best celebrity poker player, with Jason confirming after 20 years of playing with him: "He's a grinder. He's tough... he was the only one in the game that was tight"

Ben Affleck was named as the second-best celebrity player, described as "definitely smart, definitely knows what he's doing" though performance depends on "where he is"

Bloom refused to name politicians or business people who played, maintaining her policy of only naming those who had publicly identified themselves as players

Sales Lessons: Effective Presence and Trust

Bloom teaches "effective presence" (affected with an A), focusing on subconscious dynamics by working backwards from core human fears: dying, being alone, public speaking, not belonging, not being worthy, and being stolen from

"When you start to think about what kind of emotional footprint am I leaving with these people... how can I disarm them and also cultivate trust at the same time? It takes a level of intentionality" - Molly

Instead of focusing on resume and pitch, Bloom advises thinking "How can I make this person feel like I'm with them? Like this isn't a zero-sum game"

Key practices include listening with full presence without constructing responses, asking open-ended questions, showing warmth and authenticity, and practicing "hard empathy" with people whose views or personalities you don't like

"Humans hate uncertainty. Without an edited brain... the brain thinks that uncertainty is a metabolically unsustainable state. So it equates uncertainty with fear" - Molly

Bloom emphasizes learning to relax with uncertainty and being "more curious than needing to try to have this illusion of control," which allows people to let go of priors and adapt