Molly Bloom’s life story — at only 41 — has already been through a Colorado-sized mountain of ups and downs.

For a time, she was the tabloid-press anointed Poker Princess. The Loveland, Colo. native and onetime competitive skier ran underground poker games on both coasts in her 20s, where A-list celebrities like Alex Rodriguez, Matt Damon and Leonardo DiCaprio were players.

Then, in what she later called greed and “more and more disease, there was never enough,” her poker life collapsed. She was beat up by a mafia henchman, caught up with the Russian mob and, eventually, arrested in a $100 million sports gambling ring and money laundering case. She was sentenced to a year of probation, a $200,000 fine and 200 hours of community service.
By 2013 this was Bloom’s life: she was nearly broke, hooked on drugs and alcohol, and desperate for another chance.

She found it.

First, in herself, when she wrote a book about her experiences, “Molly’s Game: The True Story of the 26-Year-Old Woman Behind the Most Exclusive, High-Stakes Underground Poker Game in the World.” Later, she met Oscar-winning screenwriter Aaron Sorkin, and the movie he wrote and directed with her assistance, Molly’s Game, released in 2017, gave Bloom another and bigger chance to reset her life. (When Bloom met Sorkin, after weeks of cajoling to get in the door with the renowned writer, he listened to her story, Bloom recalls, and then quipped: “Never have I met someone so down on their luck and so full of themselves.”)

Now a national speaker and entrepreneur, Bloom recently brought her story of rise, fall and redemption — and tips on exceptional customer service, taking risks and leadership — to Sarasota. The event, presented by the Gulf Coast CEO Forum and the Lakewood Ranch Business Alliance, was titled Bet on Yourself and You’ll Always Win: Overcoming Setbacks. “Courage isn’t about fear,” says Bloom. “It’s about doing it anyway.”

In an interview with the Business Observer after the event, Bloom talked about her career, lessons and what she’s up to next, including developing a behavior modification smartphone app, writing another book and creating two TV shows. Edited excerpts:

What did your poker days teach you about delivering top-notch customer service?

I’ve always had an inherent curiosity about people – maybe it comes from having a psychologist father. You have to cultivate an authentic curiosity about who people are, what drives them, what motivates them, what brightens their day. We tend to complicate things too much, and knowing your customer is about being a good person and being a good friend.

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