Molly Bloom
Image Credit: Molly Bloom

In conversation with Molly Bloom

To talk with Molly Bloom is to talk with someone who was once a near-Olympic skier, suffered a traumatic, career-ending injury, moved alone to LA to have a break before starting law school, became a poker game runner featuring some the world’s most sought-after male celebrities, had that game collapse, moved to New York, started a new game, have it shut down by the FBI, and later be indicted in a money-laundering scheme. If it sounds like the plot beats of a breathless Hollywood movie – well, it was made into one by Aaron Sorkin, the West Wing creator.

The other side of that movie, though, finds Bloom, played by Jessica Chastain, navigating blistering silences and guilt. In our conversation, we discussed how #MeToo has changed Molly’s perspective on her time running games, how she found peace after having her life upturned, and her plans to move from making playgrounds for men to spaces of empowerment for women.

First of all – did you actually ever play poker?

[No], because most of the other game runners would play in their own games. When they had a bad night, they would manipulate the rake or not pay players on time. It just seemed like a big liability, so I stayed away and I didn’t play.

But two years ago, my friend who has a hedge fund had a bunch of women come over to play, and they’d been taking poker lessons for three or four weeks. They wanted me to play and I said, “I’ll play, but you’re all going to have to sign an NDA because I’m terrible, and everyone will expect me to be great.” Well, turns out, I’m actually not terrible.

I watched so many hands of poker, you know, and they thought I was just hustling them to take all their money. I was getting hands like you can’t believe. But it’s funny, because I don’t think it normally works that way. If I would have watched a bunch of mogul skiing for years, it’s not like I could just put on skis and be a great mogul skier. But I guess with games, and game strategy, it’s different. I still would get crushed by anybody who was good at poker.

I still would get crushed by anybody who was good at poker.

Since the accident happened that ended your career in skiing, have you skied again since?

Yeah, I love it – it’s just such a part of me. That’s where I can go and just disappear from the world. Like, put me in the middle of a snowstorm atop a mountain – nobody asking me for any favours. It’s just really a place where I find peace.

Your book came out before the MeToo movement took off. The film was produced before, but it came out after. How has that tidal wave of a cultural movement impacted your perception and how you feel about those experiences that you had organising poker games, and perhaps before that?

It’s interesting, because the film came out in that year that people were starting to have those conversations. I remember being in the room with a male studio head, and he said, “I can’t make a movie about a girl that runs an underground business, but doesn’t have a love interest – that’s an indie film. I can’t make that a big movie.” Things like that were not unfamiliar. When I first started running the games, the guys would flirt with me and hit on me and offer to buy me things at Barney’s. I was like, “No, thanks”.

When I started running the game, particularly when I became the bank, they lose a big hand, stomp out and say, “Don’t bother calling me, I’m not going to pay.” And I’d be like, “So the trip to Barney’s is off?” I saw and listened to conversations at the table. I heard things that as a woman I found to be… 

Concerning?

Concerning, disrespectful, and just sad in the lack of respect that I could tell that these people had; not all of them. I had to make a choice. Am I going to let this stop me, or hold me back in any way? Or am I going to look at this as part of the litany of obstacles and problems that come from starting a business? 

And I decided to do that. I decided to use strategy, and wits, and everything to work my way around it, while still believing in and supporting the larger movement. But I think that movements take time and they ebb and flow, and the women’s movement has really suffered some setbacks as of late. And I think that it’s very important to support [it]. But to not wait for it.

I remember being in the room with a male studio head, and he said, “I can’t make a movie about a girl that runs an underground business, but doesn’t have a love interest – that’s an indie film. I can’t make that a big movie.”

So building on that, I mean, obviously, lots of celebrities, public figures, politicians, businesspeople played at your games, and the tabloid press inevitably has an obsession with those sorts of things. You use the word business to talk about what you do, and you talk about entrepreneurship. Do you think those discussions cheapened the consideration of the fact that these were like highly meticulous environments that you created?

I think all of the conversations before I wrote my book were the low hanging fruit, and reduced me to a sexy girl in a sexy outfit. And that pissed me off the most. Because whether you like the business that I started or not, it was a real business. I became the bank. I did all of the marketing. I put up all the capital, I collected all of the debt with no official recourse. I figured out how to master the customer experience. I had 20 people working for me. I never stopped improving. I was paying my taxes. I had an S corp, and I was making $6 million a year. And I alone had to deal with every single issue; people trying to cheat in my game, people trying to steal my game, and people threatening me and, and I had to navigate it all by myself. So you can say whatever you want about me, but I was not standing in the corner in a sexy outfit. I think that I knew inherently that I had to get a different narrative out there if I ever wanted to have a career again. I basically needed my resume to be an Aaron Sorkin movie with that level of scale.

I just wanted to follow up something you said about affective presence. My understanding of it is that you act as the facilitator in environments that you’re placed in. This might be a difficult question to ask but did you, or how did you, navigate feelings of manipulation or conflict, given the fact that these men were ultimately dropping hundreds of thousands, or millions of dollars, at your game?

I talk about the moment that I started to understand, because they were so much bigger than I was when I started. I thought that rich people didn’t lose their money, and I thought they knew what to do. I thought they were in control. They were just playing this game, and they knew what they were doing. I was young, they were older, they were successful.

In LA, I think that was probably mostly true. But when I got to New York, and I expanded so much, you lose $100 million in one night. That’s degeneracy on a crazy level. I don’t care how much money you have.

I’d become quite good at persuasion – affective presence. But I guess it was balanced by, I also have your back, and I am committed to doing right, by you. When I saw that most of these people were addicts, when I saw that their lives were unmanageable, that they would stay up sometimes for three days playing, I had a choice to make, whether I was going to say, “This isn’t for me anymore, this isn’t aligned with who I want to be”, or “it’s too far”, or stay in and be all in, and use all the skills I had learned.

I think that I knew inherently that I had to get a different narrative out there if I ever wanted to have a career again. I basically needed my resume to be an Aaron Sorkin movie with that level of scale.

I call it affective presence when your empathy for the other person is as important as your outcome. I call it manipulation when it’s a zero sum game. And I learned how to manipulate, and it didn’t take much manipulation. A drug dealer doesn’t really need to manipulate a coke addict to buy his coke, right? All he has to do is provide it. Maybe loaning the money.

And I started to realise that I was the reason a guy was causing harm, but I kept going. And the reason that I kept going is because I thought, even though I had recreated it in New York, I thought the whole thing was a fluke. I didn’t think that I could leave the poker world and do as well somewhere else. And I thought it meant that I’d have to go work for some asshole boss, and be back to that powerless [state of] wondering how I’m going to pay the next bill. I didn’t get what I had done is I turned myself into an entrepreneur that could be successful in other ways. I had this binary of, if I leave this, I go back to being a regular person.

Watching the movie, it struck me that you go from being a character that kind of gets thrust into situations, someone who has agency in a sense, but doesn’t really take full control of what they’re doing. But by the end, you are conscious of everything. You’re finishing [Idris Elba’s character’s] sentences. 

Here’s the funny thing about that. Jim Walden is my attorney. He’s an absolutely extraordinary human being who fights for justice in a real way. He was a former federal prosecutor who went after the five crime families fearlessly. He takes care of whistleblowers. He started his own firm. And the first time I walked into his office, so after I got put in jail, after I got arrested in LA, I had a day and a half to get to New York City because the indictment originated in the New York scene and I had to find an attorney that’s going to represent me.

And I started to realise that I was the reason a guy was causing harm, but I kept going.

The press release says I’m looking at six years in prison. I haven’t run a game for two years, I have no money. My mom just put up her house. So I got like eight names, and I had eight meetings that day with big, fancy law firms. Every single attorney said,”If I’m going to do this, I need to earn $50,000 to even read the indictment.”. And I was like, “please ask around about me, I pay my debts”. And then Jim Walden was the last person that we spoke to. And he read the indictment, and he was like, “I know that prosecutor, this is bullshit. And I’m going to help you. And we’ll worry about the money [later]”.

If you get to know Sorkin’s movies really well, you will find that he always writes himself into his movies. When he first heard about this, he was like, this girl, she goes on 2020, she writes a book, she named some names, she just wants to be famous, I don’t want anything to do with this. But he was asked by a friend as a personal favour. And so he went, and I told him my story. Later, he started emailing me and asking me certain questions, kind of like the questions that Charlie Jaffey asks in the courtroom. And he starts to understand first from the meeting, second from the further research in the emails, that this is a different story than he thought. These are his words, not mine – this is a rare person who will do the right thing, even if it means the wrong thing gets her a lot, which is ultimately what made him want to write the movie. 

One of my favourite things about that movie is that he has such a sense of rhythm. In those poker scenes at the start, it is really noticeable. You have this intense music in the background, and then it cuts to this absolute, blistering silence – you can hear horns honk in New York City. How was it navigating this feeling that you went from constant stimulation of running pit poker – you talked about suffering with addiction, and then navigating this feeling of nothingness, this feeling that something has gone terribly, terribly wrong.

It was so dark for a while that I just slept. And then I was living at my mom’s house. She said, “You gotta get up, you got to go outside, you got to get some fresh air”, which is always her solution to every problem. But fresh air does help.

I remember walking outside and my mom lives in the mountains at 8000 feet. It was this beautiful day. And there were those mountains that I had grown up on. And I said, “I gotta figure this out. If not for me, for them.” Because they didn’t know how to help me. This was way bigger than they knew what to do.

The first thing I had to do was to figure out how to get my head right. I was deeply depressed. This doesn’t sound that dangerous, but it is dangerous for me. So bored. Boredom is a catalyst for bad things; it’s one of the most uncomfortable feelings for me. I remember when I woke up from surgery [after a skiing accident]. My first thought was, “this is going to be so boring”.

I felt dirty, and like no one would ever want to be my friend, or be my partner. It was almost a permanent stain.

I was anxious, and I was filled with shame. I felt dirty, and like no one would ever want to be my friend, or be my partner. It was almost a permanent stain. So I started doing a lot of reading – psychology, neuroscience, spirituality. What kept coming up,  over and over and over, [was] meditation, which really upset me because how boring does meditation sound? It’s like the ultimate exercise of boredom, right?

So I started a meditation practice. I started with one minute, the first day, and I started to build on it. I also was working the 12 step-program, so I had a combination of sitting with someone who was very kind. But in this woman, she lives the truth. She’s not some overwrought spiritual woman who’s sitting there with beads flowing down. She’s just a Puerto Rican from the Bronx, who was a bad alcoholic, who decided to change her life. And she is so practical about it. 

If I told her every bad thing I’ve ever done in my whole life, she said she’d heard worse. And then we looked at all the resentments that I was holding, and there was a process on how to let go. We looked at every person that I’d ever done harm to. I made appointments, even if it meant I had to fly across the country to say sorry, if they’d let me.

What happened, I would say, over the next six to eight weeks, is when my mind started to tell me stories. Or when I started to have thoughts of how much I hated myself, or how I was so depressed, I was able to disconnect from that thought and bring myself to the present moment and dismiss it and watch it as it became transient. Through that process, I was able to get intimate with the mistakes that I had made and do the best I could to make them right. To look fearlessly at the parts of my personality that I needed to change, and stop living in the past. That was the healing. That was how I got to a place of, I can’t even get out of my bed to brush my teeth because I’m so depressed and so dead, to falling in love with life again even though I don’t have any money, everyone hates me, and the tabloids. You don’t have to go to Tibet. You can do it in your living room. That’s when I started to understand what real power is.

You don’t have to go to Tibet. You can do it in your living room. That’s when I started to understand what real power is.

Can you tell me a bit more about what exactly your plans are like for a women’s empowerment platforms, and what are the life lessons and goals young women should have focus on?

I’m a strategist, and I have some odd life experiences. I spent the last couple years thinking about how to combine all of these and create something that will really have impact. And I am very sure about a couple of things.

I’m very sure that self help doesn’t work. I’m very sure that making changes within a community, where that is the culture, is extremely effective, and much more powerful. I believe that mentorship can change your life, and mentoring can change your life. I also believe that it’s hard to get good high level information about solutions to problems we encounter as women. What it looks like right now is the title, The Smart Girl’s Guide to Everything, starting with a podcast. Every week, we’ll have something that is in the effort for you to find your true power.

I don’t care how you want to use it – I mean, as long as you’re not gonna use it for crime. If the girl or woman that just wants to find and marry a really rich guy and you stay at home – great, this will work for you. Your current strategy of sending naked selfies and not knowing who you are and not knowing anything about the world – that’s not going to work for you. This is for every woman. You want to marry a rich guy, or be the President of the United States – this is for you to find your power.

This is for every woman. You want to marry a rich guy, or be the President of the United States – this is for you to find your power.

So say you have a podcast about financial literacy. We talk about investing in public markets, which everyone should do, even if they have $200 […] then, on the app, you can choose to be part of the Action Programme. So on Wednesday, everybody opens a Charles Schwab account. On Thursday, you put $10 into this index, until there’s action items that create impact. Everything from financial literacy, to understanding power dynamics and relationships, to beauty, health, and wellness, but not the bullshit, actually peer reviewed science. From the podcast, and the things that people are interested in, you start to see the community develop, and the community supports each other. There’s community engagement throughout it.

The last piece of it is the mentor piece. I’ve talked to so many successful women and they always say, “I want to mentor, but it’s too much work”. I mentor a lot, and it is – you have to create a curriculum, then manage how much people can get to you or not get to you. And so now what we have is high level information that translates into a course of action that actually makes the idea like a reality. You have access to really successful women who have made it to places that you want to go – you get to build your network like that.

This conversation was edited for concision and clarity. It took place at the Oxford Union.