The audience at the Women of Influence Conference, currently underway in Denver, fell silent as Molly Bloom took the stage, eager to hear what she had to say. Bloom—a renowned entrepreneur, bestselling author, and one of Fortune’s Most Powerful Women—began by posing the question that defined her life: How do you come back from failure?
Bloom’s answer is rooted in personal experience. Years ago, her home had been raided by the FBI. The high-stakes poker empire she had meticulously built was seized, her fortune gone. That could have been the end of her story. But as she told the Women of Influence Conference audience, she drew on lessons from her past—especially from her father, who taught her resilience after she overcame a near career-ending back injury as a young mogul skier, ultimately becoming the third-ranked skier in North America.
Bloom’s keynote traced the journey that inspired “Molly’s Game,” the bestselling memoir-turned-Oscar-nominated film by Aaron Sorkin. She spoke candidly about ambition, spectacular downfall, and the difficult work of reinvention, championing courage, accountability, and—above all—betting on yourself.
She recounted her teenage years training for the Olympics as a member of the U.S. Ski Team. The dream was within reach until a devastating injury brought everything to an abrupt halt at just 19. That loss, she reflected, could have defined her. Instead, it forced her to look inward, to confront painful fears of public failure and inadequacy. “What if people saw me fall?” she remembered thinking. That fear was paralyzing, but ultimately, facing those doubts head-on became the foundation of her future resilience.
Addressing the crowd, Bloom explained, “There’s a part of us that can listen to those bad thoughts. And with practice, you can learn to dismiss them.”
Her path forward took an unexpected turn when she moved to Los Angeles in 2004. Working as a bartender, Bloom stumbled into organizing celebrity poker games in the infamous basement of The Viper Room nightclub. “I called my mom and said, ‘I don’t know how to matter in this room,’” she recalled. Her mother’s advice—don’t focus on what you can get, but what you can give—transformed her approach. Soon, Bloom was mastering the art of observation, solving problems proactively, and building real relationships.
In just six months, she began running her own games. By 2007, Bloom had founded Molly Bloom Inc., elevating private poker nights into high-profile, immersive events. “It wasn’t just about poker,” she told the conference. “It was about community, mythology, escapism.” She poured herself into every detail—locations, ambiance, the safety and comfort of her guests. “It’s the study of affective presence—the science of how you make people feel,” she explained.
Her empire continued to grow, and by 2008, she managed the most exclusive underground poker games in the world, expanding from Los Angeles to New York City. At her peak, she revealed, a single player lost $100 million in a single night.
Yet success came with a cost: Bloom admitted she began veering from her core values. “Until then, I really cared about people and had morals,” she confessed at the Women of Influence Conference. “Slowly, I started to make decisions that were off-center from my moral code.”
The consequences arrived in 2013, when she was arrested as part of a $100 million illegal gambling and money laundering operation. Choosing accountability, she pled guilty, accepted probation and community service, and forfeited $125,000. “The judge believed I had the ability to turn it around,” she said—and she did.
Today, Bloom seeks to inspire, especially women in business. On stage, she urged her listeners to cultivate self-belief and untether their value from public validation. “Stop looking for the evidence. Be full of yourself. You are enough. You are amazing. You deserve this,” she declared. She recounted having to repeat those very words to herself before meeting Aaron Sorkin to discuss her story.
Bloom reminded the audience that bravery isn’t innate—it’s earned. “I was an anxious kid,” she admitted, “but bravery can be developed.” Her fall was jaw-dropping, but her ascent was a testament to what’s possible after failure. “Sometimes,” she concluded, “there’s a liberation in starting over.”
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