Molly Bloom

I created a lot of drama and mess in my life.

When I was making the most money at the top of my game, driving Bentleys and all that, I felt so existentially empty.

I made the choice to go into the world of underground poker.

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 was in the company of movie stars, important directors, and powerful business tycoons. I felt like Alice tumbling down the rabbit hole.

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 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 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'm really kind of a behind-the-scenes person.

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.

Because of athletics, I got real comfortable with risk at a young age.

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.

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.

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.

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.

Know when to fold. Pay attention to the signs. They're there.

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.

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.

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.

High stakes, low stakes, poor or rich - people will find a way to gamble.

When you're willing to play poker for two days and lose millions of dollars, it's no longer recreation. It's taking over.

Every card player in Hollywood wanted to come to the games. Everyone's friends and their friends wanted to come to watch.

Tobey Maguire was the worst tipper, the best player, and the absolute worst loser.

I've always been very ambitious and very determined and very compassionate at the same time.

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.

I've seen what power women have in unification, and I would love to create co-working spaces and networks for female entrepreneurs.

My mom had put her house up to bail me out of jail!

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.

I don't think anyone's private life stands up to public scrutiny.

I lived across from a cornfield when I was growing up.

I made a lot of mistakes.

I built the most exclusive and decadent high-profile club for powerful men.

I have been hugely successful at times in my life, and I have also been in ruins. But the lessons I learned on the way up were just as valuable on the way down.

It took me three and a half years to go from being sentenced in federal court to going to the Oscars.

The human spirit is so resilient, and failure teaches you so much.

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 don't really miss the Hollywood lifestyle.

Tobey Maguire and I had a tough relationship - it was a tough working relationship. We butted heads, and ultimately, I lost the Los Angeles game because of differences with him. But then I moved to New York and built a bigger game, five times bigger, making more money, and that was pretty exciting.

I hang out with my grandma, go to sleep at 8:30, and that's it.

I was bankrolling the games, vetting the players, extending the credit. My life was really stressful.

I'm definitely a gambler, as exemplified by the massive risks I've taken.

I think my gift lies in being a startup entrepreneur and creating environments and experiences.

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 think everyone can relate to that fall from grace - having life change in an instant or having to stand for some of your bad choices, that feeling of 'Nothing is ever going to be good again.'

Being humble got me very far when I went to L.A., because it was in stark contrast to this town of people who were so cutthroat.

Ideally, I would like to not be in the public eye.

Money is the great equalizer.

I'd spent life so terrified of failure that when it happened, it was very liberating.

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.

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.