In 2004, Molly Bloom moved to Los Angeles, initially working as a bartender. She was recruited by Darin Feinstein, co-owner of The Viper Room, to host high-stakes poker games in the club’s basement, which were requested by actor Tobey Maguire. By 2007, Bloom registered her own business, Molly Bloom Inc., catering to poker events. As games shifted to upscale venues like the Peninsula Beverly Hills, bets reached millions, and her events attracted celebrities, earning her the nickname "Poker Princess."
Molly Bloom ran exclusive, high-stakes poker games in New York, attracting celebrities and high-profile players to venues like the Plaza Hotel’s penthouse. Known players included people like Leonardo DiCaprio, Alec Gores, Macaulay Culkin, Matt Damon, Ben Affleck, Alex Rodriguez, Nelly, Mary Kate Olsen, Ashley Olsen, Phil Ivey, Rick Salomon and Andy Beal.