When Molly Bloom, a former member of the U.S. Ski Team, graduated college she moved to Los Angeles and began working for a real estate developer. He introduced her to the world of exclusive, high-stakes underground poker games and her life took a surprise turn.
She made $3,000 in tips the first night and was hooked. She built a business bringing in millions per year from the deep pockets of the celebrities, business moguls and dubious characters who gathered at her table. She was eventually snared by the FBI and convicted of running an illegal gambling operation, losing everything but keeping her freedom.
Her story appears in her 2014 memoir, Molly’s Game, and a 2017 movie of the same name written and directed by Aaron Sorkin.
This week, Bloom, a speaker and entrepreneur, chatted with Inman about her thoughts on the movie and her experience with real estate, and she gave a preview of her comments for the upcoming Inman Connect Las Vegas event — where she’ll be speaking during the general session Wednesday morning.
Her talk is called “Make Every Customer Feel Like a High Roller.”
What follows is a version of that conversation that has been lightly edited for length and clarity.
Inman: What did you think of the movie? Did you think it portrayed you pretty accurately?
Bloom: If anything it definitely made me smarter and funnier, so I was down with that. (laughs)
The truth is that I worked very closely with Aaron [Sorkin] for eight months during the script writing process. The first time I saw the movie at the premiere in Toronto, it was like watching my life flash before my eyes. Truly, it was like watching my life story on a big screen with 2,000 people.
What did that feel like?
Terrifying, surreal. It was one of those events in your life that it took many, many months to wrap your head around, and you just sort of had to hang on for the ride.
But I was very honored by the story that Aaron told. I felt like he really stuck to the facts. I like the way that he told the story. I don’t think he made the characters too perfect, which I wasn’t.
And I think that he did a big service to the genre because as women we don’t get to see very many movies where it’s about our professional endeavor or our winnings and failings, and there’s no discussion of a relationship.
So I really liked that he didn’t superfluously throw in a relationship into a story that just wasn’t really about relationships. I liked everything about the movie.
It was kind of refreshing that there wasn’t a love interest thrown in there.
Right, just like “we got to put one in here because romance, you know?” It wasn’t a romantic story.
It was basically a story about a business.
After watching the movie, my immediate question was, ‘Well, what happened next?’
Where the movie left off was that I had just been sentenced. Here I was 35 years old, a convicted felon, millions of dollars in debt, reputation destroyed, network debilitated. That’s about the point where I said to myself, “This can’t be how it ends. I need a second chance.”
I really thought that the best shot for that was to tell my story. And then to hopefully convince someone like Aaron Sorkin to tell my story on a big screen. I think our stories can be a very, very powerful vehicle for reinvention and for connection, etc.
I finished the book, and I really wanted to meet Aaron Sorkin. He was one of my favorite writers in Hollywood. I believe that he writes with a lot of humanity and intelligence. And trust me, I sat in a lot of meetings in which that was not the storyline that people were immediately gravitating to.
A lot of people were kind of being like, “Oh, Sex in the City of gambling,” or like “The Female Wolf of Wall Street.”
So I really wanted to meet Aaron. I went around to Hollywood, asking anyone that would listen to me, if possibly, I could meet Aaron, and I got a meeting with him, got to tell him my story, and he signed on to the project. That changed my life.
How did you start giving these talks?
After the movie came out, a lot of people were reaching out to me. I didn’t have an agency. I wasn’t set up for these things, and so people were just contacting me. And then I gave it a try, and I really enjoyed it.
I think the first time I ever spoke was in front of like 4,000 people, and it was terrifying.
But I found a lot of meaning and value in talking about my story and being able to share this message of reinvention and redemption. In the last year, I’ve really kind of prioritized it as well as some other things I’m working on.
In the movie, when you go to Los Angeles, you start working for a real estate developer and that’s how you got into poker. Was that your first experience in real estate?
It was. Absolutely. It was quite different then. This was pre-2008. I certainly saw, firsthand, the sort of craziness of the real estate market in Los Angeles at that time and how these people that I was working for were just getting more and more and more and more money. It was just mind-blowing to me.
In a YouTube video of another talk you gave you describe the developer you worked for as ‘tyrannical.’ Was he the type of personality you encountered? Or was he sort of unique unto himself when you were working in real estate?
He was unique to himself in that this guy would have never survived an HR department, and he would have never survived a legitimate company’s oversight.
Since then, I’ve met real, legitimate real estate developers that are just some of the smartest, most sophisticated people. He was a lunatic. But he was very smart, and he was very good at making deals.
As a woman, coming into the world, I want to make sure everyone’s happy with me, you know? Coming from that place. It was almost a good balancing act to watch someone who didn’t care at all if everyone was OK.
That’s not who I wanted to be ever, but it kind of introduced this concept to me that in business and in negotiations I don’t need to make sure every single person is perfectly satisfied and happy. I can be assertive and represent my side.
Now, I never wanted to emulate him because he was like a warlord, but I learned something from watching him negotiate and do these deals. Because this guy would walk into an office, and there is no reason why anyone should ever give him money, and he always got it.
Negotiation is a big deal in real estate. Do you think the negotiation skills you learned with him and with poker would help in a real estate deal?
I absolutely think that being at the poker games and also watching people make choices about economics based on the hand that they have and the people that they’re playing at the table taught me a whole heck of a lot about negotiations, about deal making, about how to play your cards metaphorically.
Is that by observing how people behaved? Or what their thought process was? Can you elaborate on that?
Watching people play the game, for sure. Getting to know the players, and then picking their brain after. So that was … like poker as a metaphor for life. But there was also … a lot of real estate people in games, [and] hearing about the deals that they were doing and the land grabs and construction and the permit process and paying debt service and being capitalized enough to see a project through and not being over-leveraged.
I got all this education from some of the biggest developers in the world. Of course everybody at the table was wealthy, and they all collected homes, so I also learned a lot about just their own purchase of personal real estate.
Have you had any real estate experiences yourself since then?
No, but I really am hoping to in a year or two (laughs). I made this giant financial mess for myself. Getting in trouble is very expensive. The Feds seized my assets in 2011, and the IRS assigned taxes to those assets, to that income, which means I had to pay millions of dollars that I didn’t have because they took it.
So that compounded with restitution and legal bills and everything, I’ve been buried for quite some time, but I’m actually starting to be in a place where it’s a real possibility that I could buy property and have a real life.
Are you hoping to buy a home somewhere soon?
Yeah, I gotta figure out where we’re going to land. My fiance is a neuroscientist, and we’re in Baltimore right now, and I’m just really hoping this is not where we stay. I’ll know in a year. So after that year, wherever we go, I’m done renting, girl. (laughs)
I’m done. I’ve been renting my whole life. And I know the math on it. Because I sat in those rooms, I know the math on it.
Right, you must be thinking of those numbers all the time, every time you pay your rent.
All the time. It kills me.
So there was one mention of real estate in the movie at the very beginning, and it was about your mom putting up her house after you were arrested. Did she get to keep her house?
Yes, she did.
So that all worked out?
Yeah. Thank God. It all worked out.
Do you know what you’ll be covering in your session at Connect?
I think we’ll be talking about the story, and then we’ll be talking about the greater themes that are agnostic to details.
What it means to be in business and to stage a customer experience and building a brand that you can really feel authentically proud to market and getting real good with the uncertainty of things and being able to ride out turbulence.
I think these are the greater themes that connect all of us. You don’t have to have run a $100 million dollar poker game. It’s all the same stuff as far as the economics of a business, how fast things are changing and how much we need to reinvent to be on top of our game.
Right now it looks like the title of your talk is going to be ‘Make Every Customer Feel Like A High Roller.’ Are you going to talk about customer service?
Yeah, I’m going to talk about customer service and customer experience. I ran the game with some of the most privileged, wealthy [people] in the world, so you can imagine that customer experience is absolutely everything.
People had elevated expectations.
When people go to your session, what kind of takeaways do want them to have?
A couple things. I would love to share some insights, some very unorthodox, but I think very relevant experience based around customer experience. I’d like to impart a message of leaning into whatever makes you unique, whatever you’re bringing to the table, and not conforming to the table.
The fact that I was able to be so successful in my world that I didn’t come in and try to think about it like another poker game.
I came in knowing that I knew nothing about this, but I knew about relationships. I knew about experiences. I knew about community. I knew about telling a good story. And those are the things I focused on, and that’s what defined my brand.
Another message that I really want to convey is to not let fear of failure keep you on the bench. I have been somewhat of a professional at failing in life and each time I’ve been able to come back stronger.
The only thing that you need is just to make that decision that no matter what happens you’re going to get back up. It’s really that simple. It’s not always easy.
In the movie, when you were fired, you could have just walked away and done something else, but instead you took the plunge and decided to start running your own games. That was pretty brave. Where do you think that came from?
I never thought it would work. I remember planning that whole thing and going, “You know what, if I have to walk away from this, it’s going to not be because I was afraid to try … I have to try this.”
Such an incredible opportunity for the business, for the network, to have power with powerful people. I was very, very sure that it was a giant opportunity, and I wasn’t just going to walk away. But I never thought it would work.
It was really me … as a 23-year-old kid going up against the billionaire boys club and asking them to forgo one of their members and let me go and operate this game, which I knew pretty little about. So I didn’t think it would work.
The odds were very much stacked against me. [It worked] because I created that night, the night of my coup, such an incredible experience.
[In my family], we just weren’t allowed to let fear own us. It’s not like I didn’t get scared, I’m scared all the time. I was just taught that courage is not the absence of fear; it’s doing it anyway. It was really a huge gift because when you start teaching yourself to walk through fear, you start to really expand your opportunities.
Now, you could argue I took it too far … but that was also part of the education.
What are your hopes for the next 12 months? What will you be working on?
I’m working on having a baby. I just got engaged, and we want to start family. My fiance and I are building a company together.
[We’re] building an app right now that helps people engage in a daily program of action to change their lives and connect them to a community of people who are doing the same thing for each other, taken loosely from our experience in AA.
Does your company have a name yet?
We haven’t thought of a name yet. I’m hoping it’ll come to me.
Anything you’d like to add that you want our readers to know before they see you on stage?
No, just that I’m super excited to see everyone and hopefully do some Q&A and get to know some people in the audience, hear their stories.
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