Meet the best poker players in Silicon Valley

Every month, some of Silicon Valley’s biggest power players meet at the Palo Alto home of Chamath Palihapitiya, an early Facebook executive who now runs his own venture capital firm Social+Capital.

The guest list reads like a who’s who of Silicon Valley’s true elites: from Yammer founder David Sacks, SurveyMonkey’s Dave Goldberg and Inside.com’s Jason Calacanis to professional athletes and poker players, including the World Series of Poker champion Phil Hellmuth.

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But this isn’t for some networking or investment opportunity of a hot startup. They meet for something much more fun: a game of poker.

“It was meant to basically put together 9 or 10 of the most competitive people in Silicon Valley and play poker,” Palihapitiya, who’s been hosting home poker nights for a few years now, told Business Insider. “Once you get this competitive group of people together on the same table, it’s super fun.”

The level of play is far beyond regular amateur tables. For example, Palihapitiya, who often walks off with the most chips, has played in some of the highest stake poker tournaments, including the World Series of Poker, where he finished 101st out of more than 7,000 contestants in 2011.

In fact, according to Hellmuth, a 12-time world champion in Texas Hold’em, the skill level is so high that he was only able to hit break-even in the first three years he played there. “In general, great businessmen are great poker players. There’s a reason these guys made so much money in the real world. Those skills translate to poker,” Hellmuth tells us.

“In general, great businessmen are great poker players. There’s a reason these guys made so much money in the real world. Those skills translate to poker,” Phil Hellmuth says.

Once the game starts, the intensity could easily turn up in a matter of seconds. They play for hours, well past 2AM on some occasions. And while the stakes remain relatively modest, $10,000 bluffs do happen in the most heated moments.

But Palihapitiya says the cash part of the game is mostly irrelevant. It’s rather about the thrill of playing and winning against highly competitive people, and just trying to master every nuance of a game that, he says, “you can learn so easily, but never master.”

Poker has relatively simple rules. In traditional Texas Hold’em poker, each player is first dealt a set of two cards, which are not shown to others, and then a shared pile of five cards on the table. The first three of the five shared cards are dealt at once, and after a round of betting, the fourth card is shown. The fifth card is uncovered after another round of betting.

But, in between each round of betting, there’s intense strategy and mind-games involved that requires a lot of intellect and discipline throughout the game.

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That’s what makes poker such a complex — and fascinating — game, Palihapitiya says. There’s a chance of overcoming a poor hand, if you play it smart. Or you could lose everything with a single mistake, just when you thought you were going to win a big hand.

In that sense, Palihapitiya says, there’s a certain element of poker that almost “mirrors life and running a startup.” It’s why so many entrepreneurs love the game. He sums up the similarities in six distinct points:

Overcoming adversity:

Depending on how you play each round of betting, you could completely change the outcome of the game — regardless of what cards you are dealt at first. It’s just like being born into terrible circumstances in life but finding ways to overcome that and succeed. Palihapitiya relates to it personally, as he is a classic “rags-to-riches” story, having grown up on welfare as an immigrant in Canada to become one of the most successful tech entrepreneurs around. “That’s a characteristic of this game that very few games have,” he says.

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Learning from mistakes:

You make plenty of mistakes in poker. The point is learning from those mistakes and fixing it in the future. “When you misplay your cards and lose a big hand, it’s an unbelievable moment of learning,” Palihapitiya says. It’s one thing not to repeat the same mistake, but it’s also important to know when you win by sheer luck. “Sometimes you just do something and it completely works, and you think to yourself, ‘I must be really good.’ The takeaway should be the exact opposite — you may have just gotten really lucky,” Palihapitiya says.

Knowing how to fake it:

Pretending like you have a strong hand, or “bluffing,” is a huge part of poker; all good players know how and when to use it properly. Palihapitiya says he doesn’t even look at his hand 90% of the time before placing his first bet. Similarly, in startups, it’s important to act confident at all times and believe in your product/vision, as he says, “In a startup, you have to fake it ’till you make it.” This is the same point Salesforce.com’s Marc Benioff says in his book, “Behind the Cloud”: “You have to act confident, even when you’re not.”

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Being a “good loser”:

There are moments in poker when you lose big just when you thought you were going to win. It often causes huge emotional tilt and impacts your subsequent decision-making power. “If you can’t keep a clear head, you’re going to start making worse decisions and those decisions will compound,” Palihapitiya says. “Poker’s great because it teaches you how to be mentally disciplined in the face of adversity.”

Getting a better read of people:

The best poker players have an exceptional ability to sense others’ emotional energy. They can read how people feel or think by just looking at their reactions to certain moves or body gestures. Palihapitiya says that ability can help you in everyday life, too, as you become “more emotionally attuned to the people around you.” In other words, you can start understanding others better, coaching people better, and even negotiating better.

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Making quick decisions and taking risks:

An average person’s life spans 80 to 90 years. Most startups are on a five-to-seven-year trajectory. A single round of poker, however, happens in a matter of just a few minutes. “Every hand in poker is a microcosm of that entire struggle (of life or a startup),” Palihapitiya says. You have to make quick decisions — and take risks — in a short period of time, with very limited information, and those decisions could have a huge impact on the outcome of the game. It’s why good poker players know how to make the right decisions quickly and take risks when needed.

Palihapitiya, who at age 26 was the youngest VP in AOL’s history, says he doesn’t have enough time to play poker as much as he used to anymore. But he still tries to tell others how great the game is through charity events, which many of his Silicon Valley friends join in together. For example, he donated all of his winnings from the World Series of Poker to the Boys and Girls Club, while he’s been hosting a number of different charity poker games that generate roughly $6 million a year.

“It’s really not about trying to make money – it’s about ‘Can you beat this guy?” Palihapitiya says. “Poker’s just a fascinating game of skill that’s exceptionally difficult to master. It really helps you disambiguate a lot of skills.”

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This story originally appeared on Business Insider. Copyright 2014