I Took a Helicopter to a Secret Billionaire's Poker Game

We're playing high stakes poker at a deca billionaire's house.

So I get this invitation, go out to New York, play with these hyper, successful business types. A poker game out in the Hamptons. Of course, I say yes. You. You never know where it's going to end up. So I rush to the airport, get on this plane. We end up landing a bit late, thinking Uber there, but we don't have any time. There was no other option. We had to rent a helicopter to get there. We're headed from the airport to the landing pad. It's going to be a first time in Hamptons, ever. A lot of New York City. I love the city, but I've never been out this way. Yeah, the whole city is insane, right? I hear gambling is going to pick up in Dubai once that casino goes up. I'm imagining we'll hear some crazy stories about the gambling out there. We're going to change in the parking lot. No, I just know I don't want to be in these airport clothes. And everything's closed, so we're gonna have to make a mad dash at it. And they go find a corner to change it. We'll see what happens. See you, Tom. The takeaway was we didn't know what we were walking into, but I think now we do. I walk into this Hamptons estate, led downstairs to the poker game, and right away I recognize three or four faces. Some real titans of business and finance, people you'd recognize. Sometimes in situations like this, I'll just go all in, over and over again. Especially at the beginning. No, not this one. Now I'm just getting them all in. So in my mind, there's obvious parallels between how someone handles themselves in a poker game and in the business world. So I'm using my chips, my stack to figure that out. I'm down all this money, an absurd amount for the game, and I ended up pulling myself back to even and a winner by the end of the night. I had a great time. This is exactly what I want to be doing. I think there might be some business that could be done between me and someone else. And maybe that was the reason I was asked to come out. I think that conversation is going to happen today over golf. I just got to do a little research so that I know what I'm talking about. I got to go get some cash. Because it's golf, you need cash. I'm eating this as fast as I can and getting the Uber and get out of here. How about I could give you 100 cash and you take him back to, like, a free hotel.

I'm sorry.

How you guys doing? Good.

How are you?

We played golf today with a friend of ours and this guy today. What a superstar.

I came in hot.

We get to the ninth hole, and we're playing the Bryson DeChambeau Challenge, where four of you start at the red stones of the golf course. We're not doing well. We're not doing well. We're three under. He hits a ball from 135 yards, super high up in the air, right? We're walking up to the green, and I'm like, oh, my God. My ball's long, my friend's ball's short, and the caddy walks over, and I'm like, I don't see Keating's ball. I think it's possible in a way.

That is for real.

Keating, you.

You.

Where did you make that from? How many yards? 115 yards. We were coming up the hill. We were bummed out because we thought we were a long ways away. Keating knocked it in the hole. He shot an albatross. I've golfed my whole life. I've never seen anybody hit it in the hole on a par five on second shot.

What I.

What I learned today, like, I need to work on. Gonna head back to the hotel and try to see what we can do. So. Yeah, thanks so much.

All right, my brother.

Chat with you tonight? Yeah, I'll send you a text tonight.

All right, guys, thank you. Maybe I'll see you later.

You know, people ask, like, what do you do for a living? This is. These are the moments that I really look for. It's like the conversation we had today, like, gets me really excited. You know, you've seen me play, like, several million dollar pots, and I don't even watch the board roll out. He calls 2.4 million, and he calls $1.2 million. Keating has just won 2.2 million. And here I am in New York, and I'm shocked. So it's a big deal. This is unbelievable. So a lot of the guys are going out to see 50 Cent, which is, like, pretty awesome, honestly. You know, I'm just gonna keep my creative energies going. So let them go have fun and see if I can do a little work now between, you know, tonight and tomorrow. If you're always thinking, look what you get out of something. I don't think you're gonna really necessarily go far. You know, you start with, like, what can I give? And I figure the other part gets figured out. Does it work every time? No, but that's okay, you know, it's just an attitude or an approach. I think it's the right one.

I don't know.

Maybe I'll stay in here tonight. So here we are in the city. I'm on my way to meet Emile Hirsch, a friend of mine that you may know from many movies. And he's the lead in Dead Money, this new poker movie that I had the pleasure of helping him prepare for. I love that he takes these obscure, unique characters. He's really into it. So excited to hear about it all. I just wanted to talk about Dead Money, that whole situation. How are you feeling?

I feel good. I mean, we put, you know, our hearts and souls of the movie. And Josh Wilcox, the writer, was an actual poker pro, you know, Grindr, who was at Hustler for hours and hours and hours, you know, a day. And so there's a certain amount of authenticity to the. To the movie before we even shot the film. I mean, I remember coming out to Vegas with. With you and playing at your game, you know, and like, you know, at one point, I mean, I think the first day I lost like six figures playing the game. I mean, it was like, you know, and before that, I had never even gambled more than like, you know, $500. It was really crazy. And it really helped put me in the mindset.

Everyone who's in poker loves poker. They want good poker movies. They're dying for good poker movies. How do you think people will look at this movie, you know, in a few years time?

The director did a great job. Luke Wildpost and the screenwriter, Josh was great. And the whole cast, so many great actors, and they all delivered. And, you know, the other reason why I think it's going to be really well regarded is because I saw it and it's awesome. You know, that's the main reason I

met another actor on your movie, Conlan. He was on the same scenes. The golf scene.

Yeah, yeah, yeah, he was great.

I wanted to support him, and I put a little money into, like, an independent film that they're making. Yeah, they invited us over to the studio to come watch. It could give us like a special viewing. So down to go do that? Yeah, let's go. Yeah. All right, cool. All right, we'll pack up here and head over there.

All right. I like the way you die.

Sorry. Yeah. Hey.

Hey.

What's your name?

I big fan.

S here.

S cool. Glad to meet you. Are you here for play or. We're going to go watch a screening for, like, an independent film. Oh, wow. Okay. Yeah, so we're just kind of hanging out with some friends. Awesome.

Great to meet you.

Yeah.

Good luck getting recognized on the street of New York right now. I'll have to give him that 10 bucks later.

I feel like I'm happy that I'm kind of going in a little bit blind. We've talked about it, but like, yeah, it's gonna be a.

It's better that way.

Yeah, I think so.

You know, you get a better experience.

Well, to be fair, the whole point was to support you and there's no interpretation of what's gonna happen. I'm just happy that.

No, I really appreciate that.

Yeah, I am, I am. Yeah, It's a world of me, so.

I think you're gonna be proud. He's gonna love it.

Trust me, Brother.

So long.

Happy. Senior.

Good to see you. Fantastic. How are you?

Good.

How you doing? Very good, Very good.

Congrats on finishing your project.

Thank you, man. I couldn't have done it without you.

We're excited.

Thank you for believing in me. Hi, how are you?

You should see my heart rate. I'm at like 140 people.

Really? Because I'm in the room. Thank you again for helping us make this happen, Alan. Really appreciate it.

Appreciate it. Excited. I've never had this experience. I was so into it. I've never been like, so invested in a 25 minute film. I was like, oh, man, I got exactly what I was meant to feel. So fast. Right? I'm hyped up too. Maybe I could be an actor.

Alan, I hope you're satisfied. I hope you know, dude, I have

no idea it would be that good. You talk so much about him.

I'm like, all right, well, I tried to tell you. I don't, I don't lie. There's not many people I hype up.

There are no refunds.

Alan.

No, Alan. We've only met for like frickin two hours. This guy was like, yeah, he wasn't so sure. You know, it's not easy.

What do I know? I don't know anything about movies.

He doesn't know.

I don't know anything about movies. Acting is way out of my comfort zone. Recap. That. That short film was shocking. I loved it. It's intense. Got my heart raced. I mean, I think we all like. You heard the reactions in the theater. It was really cool. It's been a fun New York trip. Happy we did this. Yeah. So we're on the flight home. So overall on the trip, what did we do? We made some new friends, found some adventure and went to places we hadn't been before, got to talk about some new ideas and. And get some balls rolling on some different projects that could go somewhere. I'm really happy with the whole thing. It's been unique to share it with you guys because used to kind of being in my own lane and not expressing myself or recapping things, but it's a little more fun having everyone come along. Yeah, I'm really happy. So I hope you enjoyed it, too. I don't know what you guys want to see and what you enjoyed. Let me know what you want to know more about, what you want to see more of. I'll be scanning the messages and using that as feedback, and we'll keep going.

I wonder if after this, people will still be asking, what does Alan do for a living?

This.