Uploaded July 2021 | Updated September 2026, 1 hour ago
Welcome to The Quest Season 2: Episode 11 with Molly Bloom: the star of Oscar-nominated movie 'Molly's Game' shares her real-life story from Olympic hopeful to running Hollywood’s top underground poker game.
Molly Bloom started out as a freestyle skier, but somehow found her way into Hollywood through a poker game. Molly had to give up on her Olympic aspirations after sustaining a serious back injury in 2002. During a gap year before law school, she moved to LA and ended up running one of the biggest high-stake poker games in the world (first in LA, then later in New York). Her clientele came from Hollywood’s top 1%, including Tobey Maguire, Leonardo DiCaprio, and Matt Damon. If you've watched the Oscar-nominated movie Molly's Game, you know what happened next: she got robbed at gunpoint and raided by FBI. They seized all her assets, and she became a convicted felon.
0:00 Intro
1:13 From skiing, a gap year in LA to poker
5:06 ‘I had a lot to prove’
14:12 Losing it all after making $5M a year
26:00 Making ‘Molly’s Game’, addiction and the inner game
34:19 Getting adrenaline from elsewhere
42:06 The ayahuasca story
51:07 Life after the movie
56:15 Reconnecting with family and meditating
1:05:57 Quest Fellow Q&A: Serena
THE QUEST POD:
🎧 Join Twitch co-founder, Justin Kan (aka your favorite founder's favorite founder), on a quest to discover the human stories behind icons in tech, business, sports, music, and beyond. Let’s F**king Grow.
SUBSCRIBE TO THE QUEST MEDIA ► @FractalRadio
SUBSCRIBE TO MY ADVICE AND LIFE STORIES ► @JustinKanTV
LISTEN TO THE QUEST POD ON APPLE POD/SPOTIFY:
🔴 Apple: podcasts.apple.com/podcast/the-quest-with-justin-kan/id1533022759
🟢 Spotify: open.spotify.com/show/7zLH9PYMRqjkvfgjGa4iHo
FOLLOW ME ON:
🕊Twitter: twitter.com/justinkan
📂 LinkedIn: linkedin.com/in/justinkan
📸 Instagram: instagram.com/justinkan
🤳 TikTok: tiktok.com/@justinkan
READ ABOUT THE QUEST POD IN PRINT:
👉 https://thequest.media
#MollyBloom #TheQuestPod #JustinKan
Welcome to The Quest Season 2: Episode 11 with Molly Bloom: the star of Oscar-nominated movie 'Molly's Game' shares her real-life story from Olympic hopeful to running Hollywood’s top underground poker game.
Molly Bloom started out as a freestyle skier, but somehow found her way into Hollywood through a poker game. Molly had to give up on her Olympic aspirations after sustaining a serious back injury in 2002. During a gap year before law school, she moved to LA and ended up running one of the biggest high-stake poker games in the world (first in LA, then later in New York). Her clientele came from Hollywood’s top 1%, including Tobey Maguire, Leonardo DiCaprio, and Matt Damon. If you've watched the Oscar-nominated movie Molly's Game, you know what happened next: she got robbed at gunpoint and raided by FBI. They seized all her assets, and she became a convicted felon.
0:00 Intro
1:13 From skiing, a gap year in LA to poker
5:06 ‘I had a lot to prove’
14:12 Losing it all after making $5M a year
26:00 Making ‘Molly’s Game’, addiction and the inner game
34:19 Getting adrenaline from elsewhere
42:06 The ayahuasca story
51:07 Life after the movie
56:15 Reconnecting with family and meditating
1:05:57 Quest Fellow Q&A: Serena
THE QUEST POD:
🎧 Join Twitch co-founder, Justin Kan (aka your favorite founder's favorite founder), on a quest to discover the human stories behind icons in tech, business, sports, music, and beyond. Let’s F**king Grow.
SUBSCRIBE TO THE QUEST MEDIA ► @FractalRadio
SUBSCRIBE TO MY ADVICE AND LIFE STORIES ► @JustinKanTV
LISTEN TO THE QUEST POD ON APPLE POD/SPOTIFY:
🔴 Apple: podcasts.apple.com/podcast/the-quest-with-justin-kan/id1533022759
🟢 Spotify: open.spotify.com/show/7zLH9PYMRqjkvfgjGa4iHo
FOLLOW ME ON:
🕊Twitter: twitter.com/justinkan
📂 LinkedIn: linkedin.com/in/justinkan
📸 Instagram: instagram.com/justinkan
🤳 TikTok: tiktok.com/@justinkan
READ ABOUT THE QUEST POD IN PRINT:
👉 https://thequest.media
#MollyBloom #TheQuestPod #JustinKan
