Chapter 42: Molly Bloom on poker princess privileges and pushing past pomposity
19/03/2026
0:00
54:54
Join me on the couch in Molly Bloom's hotel room at the Four Seasons in downtown Toronto.
Molly began her career as a world-class skier, but while training as a pre-teen was diagnosed with severe scoliosis. Her doctor told her she could never ski again, but even as a pre-teen Molly had incredible strength of mind and she ended up back on the slopes only a year after her surgery. By age 21, she was ranked #3 in North America. She then took off to LA and began running one of the most exclusive, high-stakes, underground poker games in the world, featuring players like Alex Rodriguez, Tobey Maguire, Leonardo DiCaprio, Ben Affleck, and was raking in millions of dollars per year.
Then what happened? The feds went after her! The mafia went after her! And there was a dramatic takedown. While awaiting sentencing, she wrote her life's story in her memoir, Molly's Game. That book became a bestseller and was turned into a movie written and directed by Aaron Sorkin, writer of The West Wing and The Social Network, starring Jessica Chastain (as Molly), Idris Elba, and Kevin Costner. Molly has been featured on Ellen, NPR, LA Times, VICE, and many more. But beneath the surface is a story that, as she says in this chapter, has never been shared before. There was a journey happening inside Molly that forced her to look at the downsides of her ambition and addictive personality. So get into something comfy, grab a seat between us, and let's talk about life altering public defeat, how a memoir transforms into an action-packed Hollywood feature, the liberty in losing everything, finding the 'monetizable asset' in your life, and Molly's 3 most formative books. Let's flip the page back to Chapter 42 now....
Molly began her career as a world-class skier, but while training as a pre-teen was diagnosed with severe scoliosis. Her doctor told her she could never ski again, but even as a pre-teen Molly had incredible strength of mind and she ended up back on the slopes only a year after her surgery. By age 21, she was ranked #3 in North America. She then took off to LA and began running one of the most exclusive, high-stakes, underground poker games in the world, featuring players like Alex Rodriguez, Tobey Maguire, Leonardo DiCaprio, Ben Affleck, and was raking in millions of dollars per year.
Then what happened? The feds went after her! The mafia went after her! And there was a dramatic takedown. While awaiting sentencing, she wrote her life's story in her memoir, Molly's Game. That book became a bestseller and was turned into a movie written and directed by Aaron Sorkin, writer of The West Wing and The Social Network, starring Jessica Chastain (as Molly), Idris Elba, and Kevin Costner. Molly has been featured on Ellen, NPR, LA Times, VICE, and many more. But beneath the surface is a story that, as she says in this chapter, has never been shared before. There was a journey happening inside Molly that forced her to look at the downsides of her ambition and addictive personality. So get into something comfy, grab a seat between us, and let's talk about life altering public defeat, how a memoir transforms into an action-packed Hollywood feature, the liberty in losing everything, finding the 'monetizable asset' in your life, and Molly's 3 most formative books. Let's flip the page back to Chapter 42 now....
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