For a Poker Player, Wall Street Was in the Cards

WESTPORT, Conn. — There is almost nothing on Vanessa Selbst’s tidy, unadorned desk on the second floor of this suburban office building that would suggest its occupant is the most successful female player in the history of professional poker except, perhaps, a neat stack of $5 bills to the left of her three monitors.

That is a collection she has taken from her colleagues at Bridgewater Associates, the hedge fund where Selbst has worked since last fall, for a gambling guessing game she has introduced to the office on the arguable premise that it somehow might help sharpen their strategic acuity.

For a 34-year-old whose nights and days used to be consumed by endless hours grinding at felt tables in casinos from Barcelona to Melbourne, it is evidence that she really can find action anywhere. “I do try to get people gambling as often as I can,” Selbst said, chuckling.

Her bosses at Bridgewater clearly do not mind; a faux-hawk-sporting poker champ with a Yale law degree probably makes perfect sense for a firm guided by Ray Dalio, Bridgewater’s chief executive, and his philosophy of assembling teams of disparate, iconoclastic people and seeing what happens.

“We hire botanists, we hire political science people, we hire Rhodes scholars, we hire athletes, we hire poker players,” said Kevin Brennan, Bridgewater’s head of investment analytics, where Selbst works as an investment associate. “We’re looking for people who are really, truly different.” (At a conference last year, Dalio, 68, who recently announced that he was planning to step back from day-to-day management of the firm, said joining Bridgewater was like going to a nudist camp for the first time.)

Selbst’s decision to shed her PokerStars hoodie and submit to a 9-to-5 routine in suburban Connecticut is, in many ways, just another surprising choice for a woman known for making unconventional calls.

After all, she first came to the notice of the wider poker world in 2006 for a disastrous bluff at her first final table of a World Series of Poker event in Las Vegas. (She went all in with a 5 and a 2 against, it turned out, a pair of aces.) She eventually won $101,000 and seventh place in that contest, but that bust gained her a reputation — bolstered later by several other awe-inspiringly successful or horrifically failed bluffs now central to her YouTube fame — as a reckless aggressor.

By the time she announced her retirement from pro poker in a New Year’s Eve 2017 post on Facebook, Selbst had won three World Series bracelets, netted $11.9 million in tournament winnings and spent a brief spell in 2015 as No. 1 in the Global Poker Index ranking. Only 65 other people have crossed the $10 million earnings threshold — and none are female or, as Selbst is, openly gay.

Not long ago, Selbst disparaged the notion of going into finance, telling The Financial Times that it was an option for “a lot of bored poker players.”

“I’m also anti-capitalist at heart,” she added, “so it doesn’t really fit in with my values, I guess.”

Now, she said in an interview, she sees it both as a more stable lifestyle as she and her wife expect their first child in October and as an intellectually stimulating challenge.

But even more than that, Selbst said, it’s a means to an end, that end being making as much money as she can as quickly as she can to help finance the progressive causes she supports. She has long been an active philanthropist; her charitable foundation, Venture Justice, for instance, pays for a two-year fellowship for a lawyer at the NAACP Legal Defense Fund through a program organized by Equal Justice Works. She has also raised $500,000 for the Urban Justice Center via an annual charity poker tournament and served for a time on that organization’s board. “Am I going and working with clients in prison? No, but at the end of the day, we’re investing money and we’re making money, and that’s important,” said Selbst, who earned her law degree in 2012 and worked part time in recent years for a police-misconduct litigation firm. “Hopefully, if I’m good at this and I do well, then that’s probably the most efficient way for me to support the causes that I care about.”

Selbst’s pivot also reflects her gimlet-eyed view of poker today.

In the early 2000s, she was among the flood of players inspired to play by the 1998 film “Rounders” and the out-of-nowhere $2.5 million World Series of Poker championship win in 2003 by a Tennessee accountant and online player, Chris Moneymaker. (Yes, his real name.) Curious, Selbst started playing online and built her account up to $150,000 by the time she graduated from Yale with a political science degree.

After graduation, she worked as a management consultant in the New York office of McKinsey & Co., but the cards kept calling her back.

“I was playing poker for one-third the amount of time and making three times as much money,” said Selbst, who splits her time between the Brooklyn home she shares with her wife and a Westport residence near the Bridgewater offices. “I was like, ‘OK, I’ve got to give this a shot.'”

For elite poker players, it was a golden age. Selbst found it easy to reliably haul in $500,000 in profit annually — and often a lot more. More recently, though, an industry of instructional videos and books on how to win has fueled a steep rise in good players even as the available money has remained the same.

“You have no job security, no health insurance. You’re traveling constantly. You have no stability in terms of your life,” Selbst explained. “And there are huge swings because if more people now have a chance to win, it’s very easy to have a losing year.” The lifestyle was also hard on her wife, Miranda Selbst, who oversees a joint venture between the United Federation of Teachers and the New York City Department of Education to improve learning at low-achieving elementary schools.

“A lot of poker spouses are put in the awkward position of having to give up their passions to just support this other person,” Miranda Selbst, 37, said. “It’s very hard to explain to your friends at home who have 9-to-5 jobs and think you are on vacation all the time. People don’t really know how lonely and boring that can feel.”

Vanessa Selbst was introduced to Bridgewater by a pro-poker friend, Galen Hall, who left the circuit in 2011 to earn an MBA at Stanford before the hedge firm hired him. As Selbst expressed frustrations with both poker and her ability to effectuate more good in the world, Hall urged her to visit Bridgewater.

Selbst was impressed to learn that Bridgewater — which has $160 billion under management from more than 300 pension funds, sovereign wealth funds and other institutional investors — makes its money for clients not by trading individual stocks but by betting on shifts in a wide range of macroeconomic international data. As her Twitter profile now slyly alludes — “I used to gamble and wake up late; now I gamble and wake up early” — her poker skills could apply.

“If something’s undervalued, does that mean you want to buy? Well, maybe, but if you buy it, how’s it going to go up? Who are the other people who are going to buy? What are they thinking about? What’s their motivations?” she said, offering an analysis that could fit either an investment or a poker hand. “You have to be thinking about who the other players are and what they’re going to do.” For now, Selbst is far too junior at Bridgewater to have a pivotal role in big decisions. She admitted, too, to having struggled through the firm’s intensive nine-month crash course on economics and the company’s trading philosophy. Her poker success relied largely on exploiting a personal image of being intimidating and terse; at Bridgewater, she discovered, she must be approachable and collaborative.

“It was really hard initially, and I wasn’t doing well at all, so it was less about wanting to be the star and more just not being used to doing poorly at something,” she said. “My defensive mechanism kicked in, and so then people were like, ‘You’re really defensive.'”

At Bridgewater, she said, she has learned to tame that, but her more obstinate persona re-emerged this month when she was mocked for busting on a wild bluff the first day of the World Series of Poker’s $10,000 buy-in No-Limit Hold ‘Em Main Event in Las Vegas. (Despite her retirement, Selbst intends to play in occasional high-profile tournaments.)

She slapped back angrily on Twitter in a series of middle-of-the-night replies capped by this: “I wish I could just ignore people’s tweets but this irks me so much. Everyone who posted here is epitomizing exactly what is wrong with poker these days.”

The next afternoon, Selbst was more amiable as she cheered on Hall, her Bridgewater colleague, as he finished first and won $888,888 in a different World Series event.

Hall, 32, pointed to Selbst’s counterintuitive play the day before in explaining why she will do well in her new job.

“Here’s somebody who has won a ton of poker tournaments, so obviously she knows what the standard play is, but she does something different and you say, ‘Oh, you’re an idiot,’ instead of taking five seconds to think about what this hyper-intelligent, hyper-successful person is doing,” he said of her critics. “At Bridgewater, what’s really valuable is people who can think extremely independently.”

Selbst expressed relief “that this is not my life anymore.”

“It’s a very insular world,” she said of poker. “It’s fun to come back and play and see people, but it’s also really nice to know I have somewhere else to get back to.”