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The Diary of a CEOThe Diary of a CEO

"He Put A Gun In My Mouth, Then Beat Me Up!" - Molly Bloom (Molly's Game)

A crazy story...with a dark, unbelievable, ending. Welcome to Molly's game. 00:00 Intro 02:01 The Pressure to Be a High-Achiever 04:55 I Was Chasing Glory 06:16 Finding My Way in LA 07:33 Becoming the PA of the Biggest Poker Game Organiser 10:01 Entering the Poker World & Its Secrets 12:18 The Psychological Strategy Behind Your Success 17:41 Playing the Manipulation Game 19:55 Running the World's Most Exclusive Poker Nights 24:47 He Wanted My Money Or Would Take My Poker Nights from Me 28:54 Do You Resent Him? 31:42 Taking Over the Poker Scene in NY 36:18 Someone Lost $100 Million, & It All Started a Bad Spiral... 42:41 I Compromised My Integrity 44:37 The Downfall: The Crashing Impact on My Health & Relationships 48:14 The Italian Mafia Put a Gun in My Mouth 54:53 The Terrifying Moment When the FBI Came After Me 58:25 Facing 10 Years in Prison 01:03:00 They Offered to Give Me Money if I Snitched 01:08:44 What Did You Learn from This Experience? 01:11:55 How My Story Became a Hollywood Success 01:20:37 Going Through IVF 9 Times 01:24:04 What's Your Advice for Being Successful? 01:27:54 What Are You Proud Of? 01:29:37 Last Guest’s Question You can purchase Molly’s memoir, ‘Molly’s Game’, here: https://amzn.to/47oDhDS Follow Molly: Instagram: https://bit.ly/3KKe0Lk Twitter: https://bit.ly/45tjBOe My new book! 'The 33 Laws Of Business & Life' pre order link: https://smarturl.it/DOACbook ....https://bit.ly/47vPoQf Join this channel to get access to perks: https://bit.ly/3Dpmgx5 Follow me: Instagram: http://bit.ly/3nIkGAZ Twitter: http://bit.ly/3ztHuHm Linkedin: https://bit.ly/41Fl95Q Telegram: http://bit.ly/3nJYxST Sponsors: Huel: https://g2ul0.app.link/G4RjcdKNKsb

Molly BloomguestSteven Bartletthost
Aug 16, 20231h 34mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

From Underground Poker Queen To Felon: Molly Bloom Rebuilds Integrity

  1. Molly Bloom recounts her journey from Colorado overachiever to running the biggest high‑stakes underground poker games in Hollywood and New York, hosting billionaires, A‑list celebrities, and powerful financiers. She explains how skills like strategic thinking, emotional intelligence, and what she calls “effective presence” helped her build an ultra‑exclusive empire—and later enabled deep manipulation and ethical compromise. As addiction, organized crime, and federal investigations close in, she loses everything, refuses an FBI deal to betray her players, and narrowly avoids prison. The conversation closes with her rebuilding her life through sobriety, motherhood, a bestselling film adaptation, public speaking, and a renewed commitment to integrity, self‑worth, and teaching others about risk, purpose, and emotional mastery.

IDEAS WORTH REMEMBERING

5 ideas

Influence is built by how you make people feel, not what you say.

Bloom’s concept of “effective presence” centers on memorizing meaningful details (kids’ names, preferences, values) and deeply listening to people who are usually only treated as opportunities. Focusing on authentic connection over outcomes disarms egos and creates rare trust—even with the ultra‑powerful. The same skills can manipulate or heal, so the ethical intention behind them is decisive.

Strategic risk‑taking beats either timidity or impulsiveness over time.

Watching thousands of poker hands and long‑term player results, Bloom saw that those who took calculated, repeatable risks ultimately “won the game,” in poker and in business. Those who let past losses scare them off risk stagnated, while impulsive risk‑takers crashed. A healthy relationship with risk—learning when to bet big and when to fold—is central to long‑term success.

Chasing money and status at the expense of integrity erodes self‑respect fast.

Her games evolved from a clever legal hustle into morally corrosive operations feeding gambling addiction, partnering with the wrong people, and eventually taking illegal rake. As her actions diverged from her values, her self‑esteem collapsed, she numbed herself with alcohol and pharmaceuticals, and she began treating people instrumentally. She frames this as the core turning point: once integrity was compromised, every other bad decision got easier.

Ultra‑wealth and extreme success do not guarantee peace or happiness.

Behind the curtain of billionaires, studio heads, and Wall Street whales, Bloom mostly saw people dragged by obsession, unable to stop gambling, chasing more without ever having “enough.” She quotes the idea that true advantage is being able to say “I have enough,” noting that many of the richest people she met lacked basic contentment and emotional peace.

Owning your choices is often more powerful than taking the easy deal.

Facing up to ten years in prison and millions in asset forfeiture, Bloom was offered all her money back and a deferred prosecution if she became a confidential informant on her players. She refused, concluding that her predicament was 100% due to her own choices, and she would not ruin others’ lives to escape consequences. That decision became the hinge of her personal reconstruction around integrity.

WORDS WORTH SAVING

5 quotes

He put a gun in my mouth, beat the hell out of me, and he said, "If you tell anyone about this, I know where your family lives."

Molly Bloom

I believed that I had to achieve something big, huge, extraordinary, worldly in order to then feel relief from that existential ache.

Molly Bloom

Effective presence is the science of how you make people feel.

Molly Bloom

What had been about trying to be an entrepreneur and be gutsy started to be exclusively about the money and the power, but I paid a huge price for it.

Molly Bloom

This place that I was in was 100% my fault... and turning around and ruining the lives of people who had played in my game to get out of the trouble of my own choices did not feel in alignment with my true self.

Molly Bloom

Family background, overachievement, and the pursuit of gloryCreation and scaling of clandestine Hollywood and New York poker gamesEffective presence, emotional intelligence, and the ethics of influenceAddiction, moral compromise, and the psychological cost of powerOrganized crime, FBI investigation, and legal collapse of the operationRefusing to inform on players and choosing integrity under pressureRebuilding life via the book, film (Molly’s Game), speaking, and motherhood

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