Even for High Rollers, the Best Part of Poker Isn’t Always in the Cards

Men don’t always make new friends easily beyond college. We have family, those university buddies and then colleagues. Maybe a group of neighborhood or gym guys you play pickup with. Chances are many of them are like you: They live in the same kind of house in a familiar part of town. Or you share professional interests, skills or educational backgrounds. Poker, however, is not like that. You have nothing more in common with the people around the table than… you all play poker. They could be a bunch of guys you might otherwise never sit down with. And that’s where the magic happens. In fact, one of the closest friendships of my life began during one of the most disastrous poker games I’ve ever played.

I was a weekend guest at a friend’s house in Ibiza, and several of us were playing with a $2,000 big blind. One of them, a guy named Dan whom I’d gotten to know a little through the poker community, was getting destroyed. I was the fish in this group—the bad player everyone wants to play against—but it was actually Dan who was losing a ridiculous amount of money. At one point he was down about a million euros.

More from Robb Report

Poker is an intensely social, jovial game—more like Pictionary than golf. Although golf is social, you’re out on a vast green expanse, and you have to keep quiet and maintain decorum. In poker, unless you’re playing professionally, it’s almost the opposite: You’re seated tightly together, usually sharing food and drink, telling stories and laughing and cracking jokes. Doing this for hours on end, you can’t help but get close to people. And no matter who you’re playing with, whether it’s a tech titan or an A-list actor, the poker table makes you equals: It’s just my wits against yours. Much of adult life is about serious stuff—work and family responsibilities—which can breed a certain wariness about people’s motives for being friendly, especially if you’ve amassed any wealth or influence. But the poker table creates the space for adults to be kids.

That night, I found out Dan was going through a painful breakup. His distress and distraction were showing in every hand, as he made one shocking move after another. No way was this just a run of bad luck: Nobody is supposed to lose that many buy-ins in that amount of time.

We’d already been playing for about six hours, so I was ready to go out and have fun with a group who were headed to an iconic nightclub called Pacha, where a cool DJ would be playing. I pulled Dan aside and said, “Just come with me and leave the game.” He clearly wasn’t having a good time at the table, and I thought he could use any nudge to quit. So I offered him a chunk of money just to leave. Stubborn idiot that he is, he turned me down, even after I doubled my offer. He thought he could dig himself out of his giant hole if he just kept playing.

He was wrong, of course, and never did recover his losses. But that’s the night we became legit friends: When someone sees you in a tough situation and reaches out to help you, well, you recognize that person as a real friend.

Sometime later, I was introduced to Dan’s dad, Paul. I was dialing for dollars, calling friends and friends of friends to raise money for a business deal, and he was one of the people I called. Paul didn’t give me the money; he didn’t want to invest in the deal because he said it wasn’t his thing. But he told me a great story of being in a similar spot, and it was just the pep talk I needed. I raised the equity just five calls later. And that one deal was worth more than all my poker winnings and losses combined.

You might think I’m saying that poker is beneficial for business, but I’m not. In fact, if you wear your salesman hat at a poker game, you won’t get invited back. My point is that, because of poker, Dan and I became close in ways neither of us could have planned. Even though we live in different cities, we talk all the time. We’ve since traveled to more than 20 countries together, gone sailing and, of course, enjoyed a lot more poker.

During a game, with its highs, lows and reversals of fortune over the course of a few hours, you see the real person opposite you, and they see the real you. All of life happens around that table. People witness you vulnerable, victorious, generous, withholding, sly and strategic. You see the crybabies and the grandstanders, the aw-shucks attitudes and the big egos, feel the sympathy and the “I’ve been theres.” It all comes out in poker. And it can build a genuine friendship if you let it.

Sign up for Robb Report's Newsletter. For the latest news, follow us on Facebook, Twitter, and Instagram.