Building The Biggest Illegal Poker Ring In The World With "Molly's Game" Inspiration Molly Bloom

Molly Bloom (@immollybloom) is an inspirational keynote speaker, entrepreneur, podcaster and bestselling author of Molly’s Game. She is best known for her memoir, Molly’s Game, which was adapted into an award-winning film of the same name by Aaron Sorkin. Bloom’s memoir chronicles her journey from college student to LA waitress to building and operating the largest and most notorious private poker game in the world. Her games featured hundreds of millions of dollars and players like Leonardo DiCaprio, Tobey Maguire, A-Rod, Matt Damon and Ben Affleck. She joins Chris Van Vliet to talk about her amazing story, becoming a mother for the first time, how she built up her poker game in Los Angeles and New York, what she learned from it, the importance of resilience, her new podcast about Olympic scandals called "Torched" and much more!

I’m so curious, when you go to a party, how do you describe yourself?

“It’s like my least favorite question. It is so difficult to sum up and it’s hard to explain. I guess it depends on how in-depth we get into the conversation. If someone on an aeroplane asks ‘What do you do?’ I say I am a writer, because that was the last big thing that I did. I try to not go back into it because there is a lot to go into.”

Do you ask them if they have heard of Aaron Sorkin?

“Well it is such a convenient thing to say ‘Have you seen the movie Molly’s Game?’ But there is really no way to pull that off without sounding like a jerk. That is the efficient answer but I have not really found a way to say it without being pretentious.”

A lot of our life is about identity. For you, your early life was about being an athlete.

“Yeah that was my early identity. But then it turned into going to law school, and then it turned into running a poker game. But there were people that I was around where that [running a poker game] couldn’t be the answer. I would say that I was an events planner to my boyfriend’s family. But it would be nice if I could have a simple answer to these questions, but that is not the way that it has gone.”

Do you ever think about what life would be like if you didn’t get injured on the ski slopes?

“I try not to but it is unavoidable because it is the question that I get asked the most. ‘What would you do differently if you could?’ I get asked that almost every single time I am on stage. It is an impossible question.”

Everyone has a what-if moment? What was the dream when you decided to move to LA?

“Mine was so simple. I literally wanted to take a year off before law school and I wanted to be warm! When you are skiing, you spend your whole life freezing your butt off, I just wanted to go somewhere where it is warm all year.”

Going back to that first poker game, what did you think this would all become?

“So I knew that my boss was out with celebrities and billionaires, I had the sense that they would be a big deal. But I had no idea who was going to walk into the room and how that was going to feel. I went home and googled things like ‘What do poker players listen to? What do they eat?’ I had no idea that Leonardo DiCaprio and Tobey Maguire were going to be playing there. Beyond that there were politicians that were household names and other people that just have so much influence on the world. I had that moment of being mortified and out of my depth. But as the night went on, I was fascinated. It is a dream to be a fly on the wall in these rooms and have this kind of access. I have always been curious to learn about these things, having that access was so compelling.”

So taking this back, you were a server. You say in your book that you were a bad server but good at reading people?

“Oh gosh I was the worst server that my boss had ever seen. I got fired.”

How did that springboard into poker?

“My boss took pity on me and took me on as an executive assistant. I started working for them and he said that I would serve drinks at his poker game. I didn’t think it would change my life but it did. As it went on and I worked more poker games, I saw it as an incredible opportunity to network and to build this relationship and learn about entrepreneurship from the mouth of the masters. I was just intrigued and to be honest primed for a rebellion. I put everything into skiing and school, but it didn’t seem like it had gone anywhere. My brothers were doing big things and I was ready for a non-conventional path. I had given up my social life and was in the library on Saturday nights doing my homework. Seeing people betting $100,000 on a hand, it was very compelling.”

At what point did you start to realize that what you were doing was not necessarily above board?

“The first indication was that I had my money at one of the banks in Beverly Hills. One day they said that they are going to close my account, told me to empty it and that I am not allowed to come back.”

Where did that come from?

“It was a small town and I was depositing these cheques saying poker account. I guess they thought that I would be a liability to them. I had attorneys and I thought I was walking that line, but after that moment there was an indication that this was not above par.”

How long were you running these games from the very beginning to the very end?

“It was 8 or 9 years.”

I imagine when you do it for that long then you presume it is fine.

“Right. And you see people running the games at their own house, you just think that it is fine, it’s a poker game.”

Was it a huge surprise when it all came to a screeching halt?

“Yes and no. I was running the games in LA and then expanded to New York. I was then contacted by a family from the mob, and it made it clear where this was heading. The feds seized my assets and my account was -$9 million. I had been assaulted, threated and had a gun in my mouth when I refused to do business with the mob. In 2011 I just went away and the feds took all of my property. They said unless I could prove I was making it legally then they could keep it. I wasn’t making it illegally, but I wasn’t a target for the investigation. So I went away and for 2 years I tried to put my life back together. I finally moved back to LA and 7 days after I got arrested by 17 FBI agents holding guns. They then handed me a piece of paper saying ‘The United States of America vs. Molly Bloom.’

How much of a percentage of the movie would you say is in line with what happened?

“I would say 95%. I am shocked at how much Aaron actually stuck to the real events. Aaron made us all smarter and funnier than we are in real life, and some parts he did take creative liberties with. But the stories about the events and the players are all how it went down.”

What made you decide to write a book that ultimately would p*ss a lot of people off?

“My life was ruined. So I got arrested, but what the feds wanted was for me to be a confidential informant. They wanted me to wear a wire and to listen in on the politicians and the people from Wall St. I didn’t feel that was something that I could do and feel right about it. I felt like I made the choices, and I had to deal with that. Everyone thought that i was going to prison, but I had this great attorney who advised me on what to do during that year. I did community service and I went to rehab, drugs were a part of my story. We played it right and I didn’t have to go to jail. But there I was, 35 years old, no network and millions in debt. What do I do? I had to take control of the narrative and get my life back. Otherwise I am living in the mountains with my mom and my grandma, and that’s not an option.”

So how did Aaron Sorkin agree to make the movie?

“I had this shortlist of people who could make this work. Aaron was at the top of the list because he is my favorite writer. I relentlessly tried to get a meeting with him and watched all of his movies to see what would resonate with him. When you meet with someone, you can either resonate with someone or not. But he loved the story and decided to write it, direct it and make it his own.”

How did your life change when the movie came out?

“[before] I felt like I would walk into a room and people would whisper [about me]. Then it would be like ‘Oh my gosh that movie is great. It really paints you in a different picture.’ I then had a lot of opportunities come my way like being able to speak about hope and redemption. All these things I had been through now became this platform to share these inspirational messages.”

What was behind the decision to name Player X as Player X?

“Player X is a composite of multiple players. Aaron and I have no desire in taking anyone down or making them look terrible. This is a movie.”

I end every interview talking about gratitude. What are 3 things in your life that you are grateful for?

“My little girl, for you Chris and for my mom.”