The Viper Room’s Molly Bloom On What She Gained By Refusing To ‘Bark Like A Seal’

There are a lot of things Molly Bloom can do. The renowned athlete, entrepreneur, speaker and author has competed in the Olympic trials, had her life story inspire an Academy Award-nominated film and ran a multimillion-dollar poker game for some of the country’s most rich and powerful.

But one thing she refuses to do is bark like a seal for Spider-Man. 

In 2004, Bloom was working for a real estate developer in Los Angeles whom she described as “diabolical” in her 2014 book Molly’s Game and referred to as “Reardon.” He recruited her to work at the high-stakes poker game he was running out of the basement of the Viper Room nightclub with Spider-Man actor Tobey Maguire. Many prominent LA actors would attend. 

Eventually, Bloom was running her own high-stakes game with Maguire, until one day, everything changed. Maguire threatened to take the game away from Bloom — and the significant money she was making as a result — unless she agreed to “bark like a seal,” for him. She refused, and on this week’s Walker Webcast, she told Walker & Dunlop CEO Willy Walker why. 

“I've made a lot of decisions like that that have seemed to cost me a lot in the here and now but paid off later,” Bloom said. “The story you’re talking about was the culmination of a demand for compliance in a lot of different ways, in how I got paid, how I ran my business. He wanted to be the puppet master, and I couldn’t roll with that. I had to be my own woman.” 

Born in Colorado, Bloom has two younger brothers who she has affectionately called “tiny, evil, superhuman prodigies.” One of her brothers, Jeremy Bloom, was the No. 1 mogul skier in the world who went on to win three world championships and compete in two Olympics, while the other, Jordan, is a Harvard-educated cardiothoracic surgeon at Massachusetts General Hospital. 

Bloom told Walker that their success inspired her to figure out how she could get her own “seat at the table,” which led her to become a world-class skier before an injury ended her career. She moved to LA, where she got involved in the poker game and realized she had a talent for providing even the pickiest of A-list guests with a high level of personalized concierge service. 

“If you are able to see that human beings are human beings, and if you find a way to make people feel taken care of, seen, heard and remembered, that works across the board for everyone,” Bloom said. “What that involves is dropping your own ego and your own fear of ‘Who am I compared to these people?’ And to decide to just show up and be of service, there’s a lot of value there.” 

She moved to New York to start her own game out of a suite in the Four Seasons just before the Great Recession in 2008. As she describes it, she “became the bank,” so she would become “irreplaceable,” and never again have a game taken away from her. She began guaranteeing the money for the winners in an unofficial capacity, learned how to vet people and was making millions of dollars a year as a result. 

Up to a certain point, everything she was doing was technically legal. Eventually, however, she began “taking a rake,” which means taking a percentage of the pot at the end of the night. This is what put her in violation of federal law and led to her eventual arrest in 2013. 

She credits her lawyer, Jim Walden, with helping her get through the situation. Walden was willing to take her case despite the fact that the government had seized all of her funds and she couldn't pay him.

Bloom said Walden made her remember who she wanted to be and helped her realize that she never again would put her soul up for sale. Eventually, the prosecutors on her case asked her to wear a wire to gain information from the politicians, celebrities and billionaires she knew about the sports bets they were placing and other activities, in exchange for her money back and deferred prosecution. 

Bloom turned them down. 

“It didn’t feel right,” Bloom said. “The position I was in was 100% my fault, nobody tried to trick me into it. It wasn't like I didn't understand how things work, and it wasn't like I didn't have a lot of opportunities. So I just knew in my heart that I had to stand for the consequences of my own actions, and I was terrified of the outcome, terrified of jail, terrified of never making money again, but I knew I had to make that choice.” 

She pled guilty in May 2014, and while she expected to be sentenced to jail time, she instead was given a fine, probation and community service. 

In 2017, acclaimed writer and director Aaron Sorkin turned Molly’s Game into a film starring Jessica Chastain that was nominated for an Academy Award for best original screenplay. As Walker put it, Bloom went from walking toward a jail cell to walking on the red carpet at the Oscars. 

Today, Bloom is a public speaker who addresses groups on what she has learned through her experiences. She talks about the importance of believing in yourself and getting into a growth mindset to understand that, with the right amount of effort and optimism, you can change. She also speaks about the need to cultivate authentic relationships and have agency over one's own mind. 

“All those times where I felt like I was finished, I had to have this agency over my mind to shift out of the narrative, to shift out of that negative mindset and into something else,” Bloom said. 

On Oct. 12, Walker's guest will be Peter Linneman, renowned economist and founding principal of Linneman Associates. Register here. 

This article was produced in collaboration between Studio B and Walker & Dunlop. Bisnow news staff was not involved in the production of this content.

Studio B is Bisnow’s in-house content and design studio. To learn more about how Studio B can help your team, reach out to studio@bisnow.com.