I'm definitely a gambler, as exemplified by the massive risks I've taken.
— Molly Bloom
Every card player in Hollywood wanted to come to the games. Everyone's friends and their friends wanted to come to watch.
I grew up in a very high-achieving family. I have a brother who's a Harvard-educated cardiothoracic surgeon. My other brother is a two-time Olympian, fifth-round draft pick for the Philadelphia Eagles, and an entrepreneur and philanthropist.
My mom had put her house up to bail me out of jail!
I'm all about second chances.
I made a lot of mistakes.
It took me three and a half years to go from being sentenced in federal court to going to the Oscars.
When I was making the most money at the top of my game, driving Bentleys and all that, I felt so existentially empty.
The chemistry at a table is so important. You must start with a carefully balanced mix of personalities. If the balance is off, and the stakes are too big for some of the players, it kills the game. Too small, and everybody gets bored.
I believed that writing my story was my best shot to be able to pay my mom and my attorneys back and pull myself out of this massive crisis that I had put myself in.
I'm really kind of a behind-the-scenes person.
Because of athletics, I got real comfortable with risk at a young age.
I saw someone lose $100 million in one night. When you watch that, as an owner-operator of a game, you realize that these numbers are incredibly unsustainable, incredibly unhealthy. So, I was not happy about this loss. It brought me no joy or adrenaline.
Know when to fold. Pay attention to the signs. They're there.
Ideally, I would like to not be in the public eye.
I did a little soul searching to explore where I had gone wrong, why I made the decisions I did, how my definitions of success and ambition were off. I love a great new pair of shoes - I love to look at my bank account and see zeroes - but what is it attached to?
Even if there are people around to help you, you don't suffer with an audience; you don't triumph with an audience.
High stakes, low stakes, poor or rich - people will find a way to gamble.
Tobey Maguire was the worst tipper, the best player, and the absolute worst loser.
I've seen what power women have in unification, and I would love to create co-working spaces and networks for female entrepreneurs.
You're as sick as your secrets, and my whole life was a secret, so it's just... it's been really healing, and I've found a lot of inner peace by just owning everything and moving forward from there.
I lived across from a cornfield when I was growing up.
I built the most exclusive and decadent high-profile club for powerful men.
The human spirit is so resilient, and failure teaches you so much.
I made the choice to go into the world of underground poker.
Money is the great equalizer.
I think, before I had money, I believed that money would solve my problems, that it would give me power and I wouldn't have financial stress anymore, and it would completely change my life. And then, when I had money, it changed a lot of things, but it didn't change the way I felt inside at all.
I approach everything, including sobriety, with the same mentality I approached sports with. You're going to put in the time. You've got to suit up, show up, and keep your eyes on the win.
In sports, especially skiing, you have to be comfortable with risk. You have to have a relationship with fear, and it can't dominate the decision-making process.
I moved to Los Angeles. My parents were not on board with that, and so I had to get a lot of different jobs. One of them was working for a man in Hollywood who had a weekly poker game.
I logged into my bank accounts, and they were all seized, all frozen. So that was a pretty clear indication that I was in big trouble.
I would love to raise a fund or get some awesome empowered women together and put together an advisory board to get behind female entrepreneurs.
You're going up against the billionaire boys' club or trying to find your way into something you have no basis for, and it's bigger than anything you ever imagined - and then actually having that work. Having that risk pan out. It taught me to be very fearless - maybe too fearless in the end.
After I quit the U.S. Ski Team, there was a fair amount of, you know, grief that follows that, and I just wanted to take a year off. And I had a friend that lived in Los Angeles, said I could crash on his couch. And so I just kind of did the first really spontaneous thing I'd done in my young adult life.
When you're willing to play poker for two days and lose millions of dollars, it's no longer recreation. It's taking over.
I've always been very ambitious and very determined and very compassionate at the same time.
I think my gift lies in being a startup entrepreneur and creating environments and experiences.
I don't think anyone's private life stands up to public scrutiny.
I've been rich; I've been poor. I've been successful; I've been decimated. And the way I felt inside didn't change dramatically. It's less stressful to have money, that's for sure. But that doesn't mean I felt fulfilled. So I've learned to live in the smaller moments of life.
I'd spent life so terrified of failure that when it happened, it was very liberating.
I know for sure that you have to re-define power as power that comes from within. Success needs to be more comprehensive and attached to something with meaning.
You can tell a lot about a man's character by watching him win or lose money.
I was in the company of movie stars, important directors, and powerful business tycoons. I felt like Alice tumbling down the rabbit hole.
I think my dad really wanted me to survive the world. He knew as a psychologist how difficult the world is, and I think he wanted me to be tough.
I created a lot of drama and mess in my life.
I kept these games pretty intimate. You know, with this much money on the table, with this much risk, you wanted to make people feel safe. They don't want to feel like they're part of a spectator's sport - well, the winners do, but the losers do not.
My regular game in New York City was a $250,000 buy-in, no limit. So people were burning through that, a lot of times in the first 30 minutes.
This was 2008, you know. The economy was falling apart, spiraling. And I was hosting a game in New York, and there was $5 to $7 million on the table.
I had a full-time driver, or I would take my Bentley. I'd have big houses in the Hamptons for the summer, taking seaplanes or helicopters out. I did a lot of flying privately to Miami. A lot of shopping.
Getting the book published and the movie made was not an easy task. But it helped. Because even though it's a difficult life to explain, I lived it.
