M+E Daily

LOS ANGELES — Molly Bloom, the afternoon keynote Oct. 4 during the Hollywood Innovation & Technology Summit (HITS) Fall event, didn’t take long to set the tone with her presentation “How to Manage Risk and Create an Unforgettable User Experience.”

“You may be wondering why MESA brought a convicted felon up here to tell you how to manage risk,” she told the packed crowd of several hundred at the Skirball Center, giving them an idea of what was to come.

The author of the memoir “Molly’s Game” — in turn made into an award-winning film by Aaron Sorkin — built and operated the largest and most notorious private poker game in the world, handling hundreds of millions of dollars with players like Leonardo DiCaprio, Tobey Maguire and Ben Affleck.

But before that now-infamous weekly poker game, Bloom’s story began as a world-class skier, where she was a member of the U.S. Ski Team, ranked No. 3 in North America at the age of 21. And a freak accident while skiing ended that part of her life, setting everything else in motion.

“It wasn’t because I didn’t show up or didn’t work hard,” she said. “It was because I tripped on a stick.”

Moving to Beverly Hills, Bloom was quickly fired from her first waitressing job, but while she was “the worst waitress he had ever seen,” he restaurant boss took her on as a personal assistant instead, and had her serving drinks at his weekly, star-studded poker game. Even though she made $3,000 in one night, Bloom wasn’t there just to earn cash: she was watching and learning. “I discovered that the [movie stars there] were there because they didn’t want things anymore,” she said. “They wanted experiences.”

After building relationships with the stars, Bloom started her own poker game in the penthouse of the Four Seasons, and essentially stole all the players from her former boss’s game. It worked because she “focused on the experience,” learning what everyone who attended wanted, and catering to their needs. “Movies got made, hedge funds were born,” she laughed.

Eventually, Bloom began a new poker game in New York, one with a $250,000 buy-in, drawing in the Wall Street crowd. “If I was doing my job properly, I managed my risk expertly,” she said, speaking to how she guaranteed losses the table, a move that worked, at least for a while. Eventually, however, Italian mobsters, shady Russian businessmen and scam artists came into the circle. And that drew the attention of the FBI, who had finally caught on to Molly’s game.

Bloom’s game was taken down after she had her dealer take a “rake,” or a commission fee on the players at the table, which is illegal for non-licensed games. Even though she was facing a decade in prison, the judge took pity on Bloom, sending her home instead.

“I’m 33 years old, millions in debt, and a convicted felon,” Bloom said. “I needed a major rebrand. I looked at the wreckage and thought ‘What’s salvageable?’ The story.”

HITS Fall was sponsored by Amazon Web Services, Box, Microsoft Azure, Ooyala, TiVo, Cognizant, DXC Technology, Gracenote, LiveTiles, ThinkAnalytics, Wasabi, Aspera, EIDR, MicroStrategy, the Trusted Partner Network, human-I-T, Zaszou IT Consulting, OnPrem Solution Partners, and Bob Gold & Associates, and was produced by the Media & Entertainment Services Alliance (MESA), in association with the Content Delivery & Security Association (CDSA), the Hollywood IT Society (HITS), the Smart Content Council and Women in Technology Hollywood (WiTH).