The Game Strategies That Shape Wall Street’s Sharpest Minds

Part 1 of 2: The Counterintuitive Lessons

We're told success in investing requires the right degree, the right connections, and countless hours grinding through spreadsheets. But some of the sharpest minds on Wall Street credit an entirely different education: games.

Not the office politics kind. I'm talking about poker, chess, crosswords, and even a werewolf murder mystery game played in a Singapore apartment. These aren't just hobbies - they're training grounds for the skills that separate good traders from great ones.

I recently came across a fascinating Bloomberg Markets investigation that profiled finance professionals and the games they're obsessed with. What struck me wasn't just the diversity of their pastimes, but how specific and transferable the lessons turned out to be. These insights were too good not to share, so I'm breaking them down into a two-part series.

Today, I'm covering the most counterintuitive principles - the ones that flip conventional wisdom on its head. Next week, we'll explore the meta-skills and mindset shifts that tie everything together.

Let's start with the lesson that challenges everything we think we know about taking smart risks.

Vanessa Selbst, once the world's highest-earning female poker player and now a trader at Jane Street, identifies the critical mistake amateurs make: waiting until they're sure they'll win.

Her contrarian wisdom? Bet whenever odds exceed 50% and size your wagers accordingly.

This isn't recklessness - it's mathematical precision applied to uncertainty. Selbst spent over a decade as a professional poker player, winning three World Series of Poker bracelets and earning roughly $12 million in tournaments. She learned that acting with incomplete information isn't a weakness; it's the entire game.

The parallel to markets - when evaluating an investment opportunity, Selbst doesn't wait for perfect information. She asks: Under what conditions does this pay off significantly, and what are the chances of that happening? That analysis happens quickly, and then she acts.

The insight cuts deeper than trading strategy. Most of us avoid decisions until we feel confident, mistaking certainty for competence. But in any field with moving variables - which is most of them - waiting for certainty means someone else already captured the opportunity.

Here's the part that feels wrong: Selbst insists that analyzing hands you won is just as important as studying ones you lost - if you won them poorly.

This flips conventional wisdom. We naturally dissect failures and celebrate wins. But a win might just mean you got lucky despite bad decision-making. If you don't examine how you won, you'll repeat the same mistakes, convinced they're strengths, until luck runs out.

Applied to investing, this means scrutinizing profitable positions to understand whether you made money because of skill or because the market happened to move your way. It's uncomfortable work - our egos resist it - but it's how pattern recognition develops.

Selbst describes this as building intuition through millions of hands. "You see certain traits, and you understand what they are, what they mean, how often they're likely to be something that you want to take the other side of or not." The skill isn't just knowing what worked; it's knowing why, and whether it'll work again.

Pete Muller runs PDT Partners, a hedge fund with over $10 billion in assets, guided by quantitative strategies. He's also a crossword constructor for the Washington Post, a singer-songwriter, and someone who once beat the North American Scrabble champion.

His approach to problems reveals something essential about maintaining a competitive edge: when things get too easy, make them harder.

Muller solves the Monday through Wednesday New York Times crosswords using only half the clues. He created his own version of the Times game Letter Boxed, which requires using all letters in just two words instead of any number. He calls it "Think Twice."

This isn't showing off - it's deliberate constraint as a training method. By artificially increasing difficulty, Muller forces his brain to find creative pathways it would otherwise ignore.

The finance application is subtle but powerful. When markets feel straightforward, that's often when we're most vulnerable. We stop questioning assumptions. We rely on patterns that worked before. Muller's approach suggests that intentionally challenging yourself during easy periods builds the neural flexibility needed when markets actually get hard.

When asked how much time he dedicates to various pursuits, Muller offers a perspective that reframes productivity entirely:

This contradicts the hustle culture narrative that equates hours worked with value created. Muller's insight suggests that the quality of mental engagement matters infinitely more than duration.

For knowledge workers, this is liberating and challenging. It means you can't simply grind your way to better outcomes. It requires cultivating the conditions for insight: the right problem, the right mental state, the right constraints. Five focused minutes beats fifteen distracted hours.

It also explains why many elite performers have seemingly unrelated hobbies. The crossword isn't a break from hedge fund management; it's training the same muscle - pattern recognition, creative problem-solving, seeing what others miss - through a different exercise.

Kerry Benn, a Bloomberg editor who competed on Jeopardy!, noticed something crucial about how contestants approach wagering. Most protect their winnings as if they're real dollars, even when they'd be better off treating them as points or play money.

Then came James Holzhauer, a professional sports gambler who routinely went all-in on Daily Doubles. His 32-game winning streak included setting a single-game record of $131,127. The crowd gasped at his bets, but his frame was different: he understood that in a game of incomplete information, aggressive bets when you have an edge maximize expected value.

Holzhauer's success changed Jeopardy! A strategy for players who followed. If one player takes chances, others must do the same to stay competitive.

Benn draws the Wall Street parallel explicitly: investors managing other people's money can take risks that would paralyze them if it were their own. If a position goes wrong, they adjust and try something else. If they're too cautious while others capture opportunities, they're out of a job.

This reveals an uncomfortable truth about risk perception. Our emotional relationship to money - whether it feels "real" or abstract - often matters more than the actual amount at stake. Reframing how you think about what you stand to lose or gain can completely alter your decision calculus.

Jane Street, a trading house with almost $7 billion in third-quarter revenue, invented a card game called Figgie to train new hires. The game simulates markets: four minutes of rapid buying and selling to maximize hand value, no playing order, just shouting offers.

Ross Rheingans-Yoo, who ran Figgie recruitment events during his five years at Jane Street, states the core lesson plainly:

New players grasp basic strategies within hours, compared to months for poker. The accelerated learning comes from the game's deliberate design: speed matters more than perfection.

This principle runs counter to academic training, where thoroughness is rewarded. In real markets—and most complex, fast-moving environments—waiting to gather all information means missing the opportunity entirely. A decent decision now typically beats a perfect decision later.

Jane Street built its fortune on the willingness to move fast when spotting opportunities. Figgie doesn't just teach trading mechanics; it rewires instincts about the relationship between speed and quality.

Next week in Part 2: We'll explore the deeper mindset shifts these games reveal - from the "best of five" strategy that prevents one loss from poisoning your next decision, to why your "superpower" might be the most boring skill you can imagine. Plus: what werewolves and chess grandmasters can teach you about when to pounce and when to pause.

One question to consider until then: Which of these principles challenges your current approach to decision-making the most? And what would change if you actually applied it?

See you next week.

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