Molly Bloom, a former Olympic skier turned poker entrepreneur, shares her wild journey from running high-stakes games for Hollywood’s elite to facing legal battles. She reveals how she made her games unique and managed notable players, including kicking Dan Bilzerian out. Molly reflects on the intense psychological lessons learned, including witnessing a staggering $100 million loss in one night. She discusses resilience, the importance of emotional intelligence, and her path to finding purpose after the tumultuous world of underground poker.
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The First Game
Molly Bloom's boss asked her to serve drinks at his poker game, which hosted A-list celebrities and high-stakes players.
This experience sparked her fascination with poker and the potential for financial gain.
volunteer_activism ADVICE
Effective Presence
Focus on making genuine connections with people by actively listening and showing curiosity.
Effective presence is about making people feel seen and understood, not just trying to influence them.
question_answer ANECDOTE
Taking the Leap
Molly Bloom planned her own poker game, upgrading the experience with a luxurious location and personalized service.
Her boss, initially angry, eventually expressed pride in her entrepreneurial move.
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In 'The Psychology of Money,' Morgan Housel delves into the psychological and emotional aspects of financial decisions. The book consists of 19 short stories that illustrate how personal history, worldview, emotions, and biases influence financial outcomes. Housel emphasizes the importance of behavior over knowledge in managing money, highlighting the power of compounding, the dangers of greed, and the pursuit of happiness beyond mere wealth accumulation. He advocates for a frugal lifestyle, long-term perspective, and a balanced approach to investing, stressing that financial success is more about mindset and discipline than about technical financial knowledge[2][3][4].
In this new episode Steven sits down with the author, entrepreneur and ‘Poker Princess’ Molly Bloom.
Molly 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
The Diary Of A CEO with Steven Bartlett 
