Poker princess parlays life story into key business lessons

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.

‘You have to cultivate an authentic curiosity about who people are, what drives them, what motivates them, what brightens their day…knowing your customer is about being a good person and a good friend.’ Molly Bloom

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.

You’ve worked for and with A-listers, business titans and Masters of the Universe types. What have you learned from that experience about what makes a great leader?

I’ve learned that being kind is really important, both to the people who work for you and to people who are customers. Kindness goes a long way. I have a mantra of be fierce, but be kind. I’m all about an assertive and ambitious leadership strategy, but I think kindness has to play a part.

Doing a lot of work on yourself is another way to be a great leader. You have to have a self-effacing life. For me that looks like mediation in the morning and an inventory at night, where I’m looking at my behaviors during the day: where was I in fear, where was I resentful, where do I owe an apology?

Caring about people around you, mentioning people, is another way to practice great leadership. Making your life and your business about something bigger than yourself is another way I stay healthy.

You talk and write about how a good entrepreneur has to live near or in survival mode to succeed. Why?

As entrepreneur, you kind of always live in survival mode to some degree. When my life fell apart, or I blew my life up, it was the most extreme case of survival mode. It was at another level. But I learned a lot from being in that place. I learned that if you want to be as successful as you can be, you have to check the ego.

I learned that you also have to forget about fear and do whatever you can to quiet the nonsense that lives in your head, that doubt and fear and ego and greed. You have to tap into what’s a priority, what’s important. I was dealing with and juggling so many things, the DOJ, the IRS, the criminal indictment, and I had to navigate how to pay my lawyer. I only had a limited amount of bandwidth to deal with all this. So I had to make this choice to not give credence or oxygen to the stuff that doesn’t matter.

That was a great place to learn from because so much of our life is consumed with giving attention, or oxygen, to things that just don’t play out. So I think survival  mode is a really streamlined, efficient and clarified mode.

How do you block out the noise now?

The most profound tool for me I have ever come upon is mediation. A daily meditation practice has enabled me to quiet the chatter and to not get engaged with the stuff that doesn’t matter, the stuff that’s so inefficient and can ultimately take you down.

I learned how to mediate with an app, Headspace, which is a cleaner, concise way of training the mind. In sports, if you a want to train a muscle group, you train that  muscle group. I don’t think we give enough attention to training our mind, to make it do we want it to do, as opposed to kind of ruling us. Now I don’t use any apps. I just sit for 20 minutes, everyday. I focus on breath and try to detach from any thoughts, emotions and fears going on, and focus on getting to a neutral mind.

Your 20s and 30s were defined by taking big risks, usually quickly. What have you done to shift the way you think about taking risks?

I don’t make choices by myself anymore. I have a panel. It ranges from my parents to my sponsor in AA to people who I respect in business. I got into trouble being a soloist, so now it’s really important to run things through not only a panel, but a matrix, and that matrix is a moral code. I need to look at things like is this moving the needle forward in a way I can be proud of? Is this honest? Is this unselfish? There’s a community matrix and moral matrix. That keeps me rooted.

I don’t believe in letting fear sideline you. I think 99.9% of the time fear is a manifestation of your mind. There are times where fear is merited, to send you a signal, and its important to recognize that, and that’s when it’s important to run it by other people who could help you out.

What advice do you have for entrepreneurs who make little and big decisions everyday?

I’m a big believer in creating some solitude for yourself. Again, for me, that’s morning meditation. It gives me a place to sit with things without running from them, without changing them, to see the truth. I run it by my group of trusted advisors. I don’t make decisions unilaterally anymore.

I used to make decisions on my own and have proven to myself in the past that left to my own devices, I can become psychotically ambitious, success at any cost. And that was a dangerous place. I also don’t rush decisions. If it’s a big choice, I get there.