Behind the Poker Face

Fletcher student Cliff Goldkind knows when to hold 'em and when to fold 'em

Cliff Goldkind flings some cards into the air

A pair of sixes is a fairly mediocre hand to be dealt in a game of Texas hold ’em poker, yet it was exactly what Cliff Goldkind needed to win the $1500 No Limit Texas Hold ’em at the World Series of Poker last year. After 35 hours of play over three days in a field of 2,302 players, it came down to that one hand, and he brought home a pot worth . . . well, let’s just say he had something substantial to report on line 21 of his tax return.

Goldkind, 25, has helped support himself for several years by playing poker, in between (and sometimes while) earning a degree in managerial economics and strategy at the University of Washington at St. Louis, serving in the Israeli army and now studying development economics and international environment and resource policy at the Fletcher School.

And that, it seems, is one of the secrets of weathering the psychological highs and lows of the game: always having something else going on in your life.

“It is different when your sole job—the only thing you are doing all day—is playing poker, and so much of your identity and your self-worth rests on monetary wins and losses,” he says, explaining that he tries to take pleasure in whether he makes the right choices based on the probabilities, regardless of whether the cards actually fall in his favor.

Goldkind, who grew up in Maryland, learned to play poker with his friends in high school. Everyone put in $20, and maybe someone went home with some spending money. None of them was particularly good at it, says Goldkind, who notes his innate ability was probably above average, but he wasn’t a natural.

It wasn’t until he went to college that he met a friend who showed him some books on poker strategy. “We started studying [poker] together,” Goldkind says. “There were several layers to the game that I had never really considered.” (See “How to Think like a Poker Player” below.) 

At the same time, his economics classes were introducing him to game theory—in other words, how people interact with one another to achieve a goal, be it a business acquisition or a stack of chips. In economist-speak, poker is a zero-sum game (the more you win, the more someone else loses) with uncertain information (you don’t know what the other player holds, and you also don’t know what cards are going to come out later on in the hand).

“You should be thinking in a game-theoretic way for every decision you make in poker,” Goldkind advises.

Close to the Chest

Goldkind honed his skills by playing online at poker websites and later in live tournaments at casinos. He says he is not a numbers genius (some of his friends are better at straight math than he is) or blessed with an extraordinary memory like some top players, who can flip over 51 cards in a deck and name the one that is left. But he knows the odds, and experience has given him a good understanding of the average player and what decisions he is most likely to make. From there, Goldkind gathers data and adjusts his strategy.

“There is a lot of really quick information you can pick up from someone, even in the first hand—how they hold their chips, whether they count their chips quickly or slowly, whether they look nervous or not,” he says. A faux pas, such as putting chips into the pot with two motions instead of one (called a “string bet”), will also mark an amateur.

Even in online games, there are ways to read another player. The player’s home country, for example: continental Europeans usually play more aggressively than English or American players.

At the table, Goldkind himself can be aggressive (in a good way), and also very quiet, focused on one hand at a time. In the World Series tournament, Goldkind followed his usual routine of not looking at the payouts until the very end. “I had a general idea what they were, but it helped me to not look at them,” he says. When it was over, and his friends told him the number, he was appropriately freaked out.

Sharing Responsibility

At first, his father, a gastroenterologist, and his mother, a medical ethicist, weren’t sure what to make of his gambling. They understood that playing poker was different from pulling a lever on a slot machine. His mother just wanted him to be happy, but it took a while—and a detailed spreadsheet—for Goldkind to fully convince his father. “I would show him monthly earnings and kind of force him to see that over a large sample size, this was a profitable thing,” he says. It certainly blew out of the water the summer earnings he made at Baskin-Robbins.

“Probably the biggest thing for my dad was not the fear that I was going to lose money in the long run. It was that poker—and this was something that I already think about poker—adds no value to society,” Goldkind says. “It can improve your thinking; it is entertainment for some people; it has some other values, but it doesn’t help the world the way a lot of careers do.”

So while poker may be the way he makes money, and he might even call it a career, he doesn’t expect it to be his life’s work. His current plan, and part of what drew him to the Fletcher School, is to explore private equity and real estate development in developing countries.

“I grew up with the assumption that I wanted to equalize opportunities globally, to learn the best way to change global structures to give more opportunities to the poorest sectors of the population,” he says.

Already his career has taken some interesting turns, like the year and a half he spent in the Israeli infantry. Although he had never lived in Israel, he volunteered to serve because he wanted to support the country as a refuge for Jewish people around the world. “I have a responsibility to take part in the maintenance of that,” he says. While he is proud of his service, it was also trying. As someone who weighs decisions carefully, he disliked when what he thought was a poorly reasoned order came down the chain of command.

“Any highly bureaucratic system, and especially one where 18-year-olds are in positions of command, is going to make a lot of mistakes,” he says. “So that got frustrating.”

That School-Poker Balance

Balancing his poker career with graduate school has gone pretty smoothly. He played very little his first semester, and then traveled internationally to several tournaments during this past winter break, something he’ll likely do this summer as well. But being away from the table for long stretches takes its toll. “Your mind gets a little rusty,” he says. “It takes me a few days on any of the trips I’ve taken to really feel like I’m back in it and thinking well.”

He has been enjoying his classes at Fletcher, but along with any graduate school program comes the expectation that you need to dress up for interviews, network and meet the right people, something he is not terribly fond of. His most recent workplaces, after all, have had pretty strict dress codes of hoodies, baseball caps and sunglasses—and the less you tell other players about yourself, the better.

Then there is the problem of his résumé. He has some impressive internships to his credit, but having “professional poker player” as his most recent work experience raised some eyebrows. “I got a lot of advice to move that down,” he says. He did.

The real challenge will be finding a career he enjoys as much as poker. At a recent tournament in the Bahamas, he played about 80 hours a week—a pretty long work week in any job. At the end of each grueling day, “I was mentally tired,” he says, “but I didn’t want to not play the next day.”

Julie Flaherty can be reached at


How to Think like a Poker Player

Whether you consider it a game of chance or a game of skill, poker is very much a game of conditional probability. That means that with every move your opponent makes and every card that’s turned over, you must recalculate the odds. The best players can do this, but it can be hard. If you had what you thought was a good hand in the first round of betting, your gut might tell you to stick with it, even if a move by another player means the odds have changed.

The same thing often happens in real life, Cliff Goldkind says. People who have put time or money into something are often unable to make decisions without taking into account that cost or effort. For example, if you buy a non-refundable plane ticket, but something comes up later to make the trip less desirable, you’ll probably still go on the trip, even if there is a good chance it will make you miserable. Or a person who has spent a lot of money on a fancy meal is more likely to give the experience a positive review. “They are a lot more likely to say they enjoyed that, or that it was worth the money and go back again just to avoid cognitive dissonance,” the Goldkind says, referring to the uneasy feeling people get when their expectations don’t jibe with reality. “You don’t want to have made the wrong decisions.”

Of course, figuring out when the odds have changed can be tricky. Say a work colleague brings three cupcakes into the office. Although they all look alike on the outside, two, she says, have vanilla filling and one has chocolate. You want the chocolate. While you casually pull one of the cupcakes towards you to claim it, figuring you have a one-in-three shot, your colleague, who knows which is which, takes a bite of another, revealing that it is one of the vanilla ones. If you think like a good poker player, you should trade your first choice for the third cupcake, which now has a two-in-three probability of being the chocolate one.

If that seems counterintuitive to you, you are not alone. The human brain just doesn’t digest conditional probability very well.—JF


Back to Top