In this episode of The Bear Roars, Dan continues his conversation with Molly Bloom—bestselling author, entrepreneur, and the inspiration behind the Oscar-nominated film Molly’s Game.
If Part 1 explored Molly’s rise, Part 2 takes us deep into the chaos of her fall—and the remarkable resilience that followed. Molly recounts how her move to New York turned her games into a Wall Street phenomenon, with $250,000 buy-ins, billionaires, and the lure of unimaginable stakes. With success came darker forces: organized crime, violent threats, federal raids, and the collapse of everything she had built.
Molly reveals the pivotal choices she had to make—between protecting her players or saving herself, and between spiraling further or rebuilding her life from scratch. She opens up about discovering meditation, repairing her family relationships, and finding strength in integrity, even when prosecutors pressured her to betray others.
Dan and Molly also talk about how her story made its way to Hollywood, what it was like to work with Aaron Sorkin and Jessica Chastain, and how the film Molly’s Game gave her a second chance. Today, she reflects on her life as a speaker, author, and mother—and the lessons about risk, resilience, and redemption that continue to guide her.
Order Dan’s Book – Bandwidth: The Untold Story of Ambition, Deception, and Innovation that Shaped the Internet Age and Dot-Com Boom: dan-caruso.com/book
To nominate a founder or yourself as a future guest speaker, email: contact@loudbearproductions.com
