Molly Bloom was on the U.S. National Ski Team before moving to L.A. and becoming a poker hostess.
Molly’s Game, based on the New York Times bestselling book of the same name, is a film set for release on Christmas day. The movie paints a picture of what the world of high-stakes underground poker looks like. Molly’s Game stars Jessica Chastain, Idris Elba, Kevin Costner, and Michael Cera. So far, Molly’s Game has 94% on Rotten Tomatoes.
The movie is based off of Molly Bloom’s memoir, “Molly’s Game: From Hollywood’s Elite to Wall Street’s Billionaire Boys Club, My High-Stakes Adventure in the World of Underground Poker”. Her book described how a multi-year underground high roller game of poker.
When it was released, tabloids and mainstream news publication touted the book, because of Molly Bloom’s insight into how well-known A-list celebrities act when cameras are not rolling.
The Poker Princess
Molly Bloom, who some of the celebrity poker players named “The Poker Princess”, started out as a timid high-stakes Poker game hostess, but eventually hosted a high-stakes cash game of poker for A-list celebrities and millionaires. How did she get to be such a powerful head in such an exclusive game?
Recently, Molly Bloom spoke to a room full of entrepreneurial businesswomen at Fortune’s Most Powerful Women Next Gen Summit in Laguna Niguel, California. Discussing her many lessons learned while running a poker game for rich, powerful men, Molly Bloom shared the lessons she learned after reaching such a rapid high and sudden low. Eventually, Molly was prosecuted for her role in the poker ring, which might have involved $100 million.
Molly Bloom’s family is a group of high achievers. While one brother is a two-time Olympian, the other is a Harvard surgeon. And Molly herself once was an Olympic-class skier. Among the Bloom kids, the level of success was high and expectation to reach it was unforgiving.
Fortune Magazine Interview
In an interview with Fortune’s Pattie Sellers, Bloom said, “The motivations I had for being successful were somewhat dysfunctional. Literally if you weren’t the best in the world in my family, it wasn’t impressive. I was looking for this thing that was going to make me feel fulfilled inside.”
Molly Bloom did not build the exclusive poker game herself. She was hired as an assistant to a restauranteur who had a big secret. He organized and bankrolled a high-stakes underground poker ring.
Eventually, the restauranteur gave Molly tremendous responsibility in keeping the operation going. She became the face of the operation, handling some of the biggest stars in the United States.
High-Stakes Underground Poker Game
Molly’s games included clientele well-known Hollywood actors, including Leonardo DiCaprio, Ben Affleck, and Tobey Maguire. One of Boom’s regular games in New York had a $250,000 buy-in, attracting Wall Street financiers and then resulted to evenings where players would leave millions of dollars rich, or poorer.
Bloom added, “I finally had that thing. And I think that’s what led to the compulsiveness to chasing it so far down the line.”
Molly Bloom in Real Life
It wasn’t always so easy for the suddenly popular Molly Bloom. But the choices she made initially helped her to build her empire. Bloom never played in the games, but instead, she fulfilled the roll of the bank or “the house”, something akin to a junket operator in Macau.
Bloom said, “I was bankrolling the games, vetting the players, extending the credit. My life was really stressful. I didn’t have the traditional resource to collect on debts and I’m certainly not going to be violent about it.”
Bloom even paid taxes on her underground poker business. She said, “In 2009, my tax returns showed over $4 million. Sometimes those tips were really big. One night, I saw someone lose $100 million.”
The majority of Blooms returns weren’t from the game itself, but from the many lucrative tips for extending credit to players who couldn’t pay out. That money had to be guaranteed in order for Molly’s Game to maintain it’s a-list player list. So, in the end, Bloom’s boss had to guarantee the winnings, while organizing the game.
Enter: Russian Mobsters
After several years, the business crashed quickly. The list of Hollywood’s popular A-List players disappeared. Replacing them were Russian mobsters. She was often stiffed for money from players. The stress of the job began to wear her down, and she soon became addicted to drugs.
Her biggest downfall was in the last seven to eight months of Bloom’s high-stakes games, when she “crossed that little gray line” and began taking a percentage of the pot.
When asked whether it was ambition, greed, or naïvité that did her in, Bloom said, “I think it was all those things. I was in way too deep, trying to hang on to this thing that had established and legitimized me.”
The Russian mob ties brought an inevitable FBI investigation. The government seized Bloom’s funds during the FBI investigation of her activities. In the ensuing prosecution, Molly also had to sell off some of her many luxuries to help cover lawyer’s fees. She also had to serve a year of probation for crimes she committed while working for the underground poker ring.
Molly Bloom’s Arrest and Trial
In the end, Bloom lost every dollar she had made. She gained an experience of a lifetime, though. Her role as the bank helped learn what her value as a businesswoman is — and the power that she can have using those skills. Molly Bloom came out so much more than the timid hostess she was when she began.
At the time, Molly Bloom went from a twenty-something looking for herself to a person of power and authority. She told Fortune, “I was no longer this object of desire. I was someone who let them have their money to play the game—or didn’t.”
When asked what her next project would be, Molly said, “I would love to raise a fund or get some awesome empowered women together and put together an advisory board to get behind female entrepreneurs. I am definitely more of a behind-the-scenes person, though. Ideally, I would like to not be in the public eye.”
Bloom said she has no regrets. She hopes that she can take her underground dealings and shift them into more of a traditional career choice. Molly’s confident she has the skills to contribute to a legit business enterprise.
