The Biggest Bluff

Those two setups create rather different dynamics. Cash games are War and Peace. You’re a thousand pages in and still no closer to finding out how the battle resolved itself. You can try to flip ahead, but events will unfold at whatever pace they choose. Tournaments are far more Shakespearean in nature. You’ve barely hit act three and half the cast is already dead. If you want an overview of life at warp speed, tournament poker is the way to go. That’s what I choose.

After spending the several months following my von Neumann revelation poring over books on poker, watching videos of the best pros playing and listening to the commentary, I began to genuinely wonder if, in poker, I could finally find a way to overcome my all-too-human inability to disentangle chance from skill in the morass of daily life, and instead learn to master it. Could poker help my husband figure out his next career move, and when it was right to just start playing again as opposed to waiting for the perfect cards? Could it help me think through when to give up with the medical consultations, or how to deal with the fallout of the bills in planning our financial future? Could it help my mother leverage an unfavorable table environment, so to speak, in her favor? Could it help me plan my own career moves in a way that would maximize my wins and minimize the losses? I decided to try my hand at finding out.

WHICH BRINGS US BACK to my meeting with Erik Seidel, for whom the challenge of poker is slightly different. For over three decades, he has led the poker world. He holds eight WSOP bracelets (only five players in the tournament’s history have more) and a World Poker Tour title. He is in the Poker Hall of Fame, one of just thirty-two living members. He boasts the fourth-highest tournament career winnings in the entire history of the game (for many years he was number one), and is fourth in the number of times he cashed in the WSOP (114). Over the years, he has spent fifteen weeks ranked first in the Global Poker Index, and many consider him the GOAT—the greatest of all time.

Why on earth would a professional poker player—the professional poker player—agree to let a random journalist follow him around like an overeager toddler, asking the most basic questions about how the world works? He doesn’t care for fame, so I can’t play the journalism card all that well. He doesn’t like to share his tactics. He’s notoriously reticent.

“I wouldn’t actually be in the book, would I?” Erik asks back at the West Village bistro as I lay out my proposal. He shifts around on the bench and hunches over a little more, as if deflecting attention from his presence as much as he possibly can.

“Well …” This isn’t going quite as anticipated.

“I don’t know if I can take anything on. You know I’ve never coached anyone. And my travel schedule …”

I cut him off. This is going nowhere fast. “I may not know how many cards are in a deck—”

“Wait, you’re serious?” He cuts me off. His eyebrows have shot up. At least I’ve managed to surprise him.

“Absolutely. I’m not going to be the typical student.”

What I do have, I continue, is my background.

“I have a PhD in psychology. I studied decision making—the sort of stuff you do every day, but from a theoretical perspective.”

“A psychologist. Now that’s interesting. That could be really helpful in poker.” He leans over the table, lanky elbows framing his egg-white omelet. “I think you’re approaching it from the area of most value, especially of most differentiated value. All the other guys are very math-based, very data-based. This area is way more open. Actually, of the great players, the ones who are some of the most exploitable are the ones who are really into math.”

“Oh, good.” I’m happy to have struck a chord after the false start. “I haven’t done any math since high school,” I admit.

“My math skills are not particularly great, either, and that’s not unusual,” Erik says, putting me at ease. “It doesn’t hurt, but it’s no barrier to playing well. The basic math is so basic that a six-year-old could do it.”

I’m relieved. But I should probably omit the part where I tell him that I usually count on my fingers.

“It’s all about thinking well. The real question is, can good thinking and hard work get you there? And I think it can,” Erik says. In a way it’s good, he goes on, that I’m an outsider. I can bring fresh eyes, perspective—and some of the skills players don’t typically have. I might not have the narrow expertise of knowing what a “range” is or why I’d want one that’s polarized or merged, but I do have the broad expertise of knowing how to learn, how to think, how people work. In Range, David Epstein reflects on the nature of the outsider: “Switchers are winners,” he writes. Perhaps, as a switcher, I’ll be able to get beyond the myopia that often comes with an insider’s perspective, bring what psychologist Jonathan Baron calls “active open-mindedness.” Not all experience is created equal, of course, but mine might be particularly well suited here.

Erik is especially intrigued by my language ability.

“You can speak how many languages?” he asks.

“Well, only two completely fluently, English and Russian. But I’ve been fluent in French and Spanish in the past, and pretty good in Italian,” I continue. “I used to take Persian, but I’ve really forgotten all of it.”

“I think that’s going to be really helpful,” Erik says. “Do you know Phil Ivey?”

I nod. He’s one of the only poker names that is on my radar.

“There was an argument for him being the best at all of these different poker games at one point,” he explains. I can think of each game like a different language that needs to be mastered. “And what’s extra fascinating about that to me is that his sister is a linguist. And she speaks fifteen languages or something.”

I’m impressed. My abilities look meager in comparison.

“How many people do you get that have that kind of a brain or interests?” Erik continues. “It seems as if Phil and his sister have a very similar brain that functions in a way that they pick up languages in some incredible way. It’s nice to hear that you do have obviously some abilities to pick up languages quickly or to adapt to different languages, because that’s essentially what the challenge is.”

It makes a certain amount of sense. In many ways, poker does resemble language learning. After all, there is a new grammar, a new vocabulary, a new way of relating to the world. But there is one big difference that I can see. Humans have built‑in language-learning ability. Some are better at it than others, true, but we all learn our native language fairly effortlessly—the brain seems to come equipped with a road map for discerning meaning out of sounds and figuring out rules without ever being taught them explicitly. Not so poker: no matter how psychologically you want to play, much of the game is about statistics. You need to understand odds, how good your hand is, how good it is relative to others’, how likely it is to improve, and so on. Each of these requires a certain amount of statistical calculation. How well I’ll fare there is another story.

“You know, psychology really is the most fascinating part of the game,” Erik says, interrupting my thought process. “What specifically about decision making did you study? Like Kahneman?”

“Actually, my graduate adviser was Walter Mischel—you know, the marshmallow guy?”

“Oh wow. That’s exciting. Self-control is huge in the game.”

So Mr. Seidel knows the marshmallow guy, too. I seem to have picked well.

“I figured it might be,” I reply. “I mean, I’ve obviously never played. But here’s what I can tell you: I’m willing to bet I’ve read more about all of this than anyone else at the poker table. I’ve done studies on stress and decision making. Emotional stuff. Time pressure stuff. All sorts of things that I think are going to be super relevant. And—and …” I’m on a roll and don’t want him to interrupt. I need him to agree to take me on. “Look at this paper I found.” I fish out my ace in the hole—a paper I’ve tracked down on poker tells that, as far as I know, never made it out of academia. And it’s based on a WSOP final table analysis. The real deal.

Erik reads carefully. He’s all concentration. And then he starts laughing.

“Wow. OK. Just don’t show this to anyone else.”

I promise him I won’t. And with that, a partnership is born.

I HAVE A RARE opportunity here: hardly ever do we have a chance to learn an entirely new skill, to immerse ourselves in novicedom, not only with the guidance of the best expert in the world but in an area, where the skill-chance continuum is so balanced, so redolent of life, as poker. Erik Seidel doesn’t actually care about whether I win any given game. He just wants to see how far we can go—how far psychology, people reading, and emotional nuance can get me. If you are starting from scratch, can a deep understanding of the human mind win out over the mathematics and statistical wunderkinds of the poker table? In a way, it’s as much a test of life philosophy as anything else. The qualitative side of things versus the measurable. The human versus the algorithmic. I will be on one extreme of a dynamic that is at the center of a paradigm shift in this country. And the ultimate test will be the World Series Main Event. The tournament has never in its history had a female champion—and only one woman has ever made the final table. Erik isn’t just training me to play. He’s training me to win: that’s how much he believes that this way of doing things can ultimately succeed. And I will do everything I can to make the journey count.

For me, this isn’t just a test of a philosophy—though that is central. It’s also personal. I don’t want to let Erik down. His faith is, in part, confidence in my ability and his approach, but is also an expression of boundless generosity: to his friends and the people he trusts or respects, Erik is the most giving person I have encountered in a long time. He isn’t just giving me his time. He is giving me his trust, his energy, his mind, his reputation. All I can think is, I better not fuck this up.

IT WAS SUPPOSED TO be a year. It became a new life. From novice, I turned champion. From amateur, I went pro. And all along the way, I watched with a mix of wonder and pride as my life changed for the better. This book is the result of that journey. It is not an exhaustive exploration of the game, how to play it, how to win at it, how to excel. It is no guide. That has been covered by experts far greater than I. It is a picking up of von Neumann’s challenge: poker as a lens into the most difficult and important life decisions we have to make, an exploration of chance and skill in life—and an attempt to learn to navigate it and optimize it to the best of our potential.

What I will offer throughout is insight into decision making far removed from poker, a translation of what I’m learning in the casino to the decisions I make on a daily basis—and the crucial decisions that I make only rarely, but that carry particular import. From managing emotion, to reading other people, to cutting your losses and maximizing your gains, to psyching yourself up into the best version of yourself so that you can not only catch the bluffs of others but bluff successfully yourself, poker is endlessly applicable and revelatory. The mixture of chance and skill at the table is a mirror to that same mixture in our daily lives—and a way of learning to play within those parameters in superior fashion. Poker teaches you how and when you can take true control—and how you can deal with the elements of pure luck—in a way no other environment I’ve encountered has quite been able to do. What’s more, in an age of omnipresent distraction, poker reminds us just how critical close observation and presence are to achievement and success. How important it is to immerse yourself and to learn new things, truly. As Erik told me that first day, lesson one: pay attention. This book isn’t about how to play poker. It’s about how to play the world.

The Birth of a Gambler

Boston, Fall 2016

“If we consider games of chance immoral, then every pursuit of human industry is immoral; for there is not a single one that is not subject to chance, not one wherein you do not risk a loss for the chance of some gain.”

THOMAS JEFFERSON, “THOUGHTS ON LOTTERIES,” 1826

You are going to be a gambler?”

That’s my grandmother Baba Anya speaking. My other grandmother, my last living grandparent. I’ve come to Boston for a family visit, nearly bouncing with excitement at my new project, and she is not impressed. To call her lukewarm would be the understatement of the hour. She has a way of setting her jaw that makes it jut out like it’s about to slice through stone. The chiseled expression of a conquering hero atop a pedestaled horse. A conquering hero—or an angry general. I can feel the full brunt of grandmotherly disappointment gather on my shoulders. She’s almost (though not quite) come to forgive me for not wanting kids after over a decade of my persistent explanations, but this—this is a new low. If you think you know the kind of disappointment a five-foot-some-odd ninety-two-year-old is capable of, think again. She was a Soviet-era schoolteacher. She’s had more practice than an army drill sergeant.

She shakes her head.

“Masha,” she says—my Russian nickname. “Masha.” The word is laden with so much sadness, so much regret for the life I’m about to throw away. In a single word, she has managed to convey that I’m on the brink of ruin, about to make a decision so momentously bad that it is beyond comprehension.

I can see the visions of Dostoyevsky’s gambler dancing through Baba Anya’s head, throwing away his life in the fictional Roulettenburg. Dostoyevsky knew of what he wrote. On a trip to Baden-Baden with his twenty-two-year-old lover, Polina Suslova, he developed a passion for roulette and “lost absolutely everything.” That didn’t stop him from wanting more: even though the game would eventually lead to the end of his affair, the near-end of his second marriage, and financial ruin, the tables held an irresistible draw. “I go to the bottom line in everything,” he wrote in one of his letters, “and throughout my entire life, I have crossed this bottom line.”

This is the fate I can clearly see written all over my grandmother’s face. A Harvard education and this, this, is what I’m choosing to do?

“Masha,” she repeats. “You are going to be a gambler?”

My grandmother’s reaction may be extreme—nothing is quite as personal as your grandchildren heading out to ruin on your watch; you have to throw your body in the breach—but it is far from atypical. In the coming months, I’ll be accused of being responsible for a society-wide “sin slide” for advocating for poker as a teaching tool. I’ll be called a moral degenerate by strangers. A group of highly intelligent people at a retreat will tell me playing poker is all well and good, but how do I feel about encouraging people—children even!—to lie?

The world of poker is laden with misconceptions. And first among them is the very one I’m seeing from a stricken Baba Anya: equating poker with gambling. I’d been ready to go, gearing up to get started. To my mind, the journey was well motivated as it was: of course people would understand that poker was an important way to learn about decision making. I mean, think of von Neumann! Let’s get to the tables! But looking at Baba Anya, I realize that the battle for support—and the justification for poker as not just a learning tool, but as one of the best tools there is for making decisions that have nothing to do with the game itself—is going to take a bit more fighting. I’m going to be explaining this over and over, so I may as well get it right.

POKER, TO THE UNTRAINED eye, is easy. Just like everyone who meets me seems to have “a book in them,” which they’ll write just as soon as they get a chance—everyone can use words, after all—so everyone who meets Erik thinks they are just a hop away from becoming a poker pro or, at the very least, a badass poker bro. Most of us underestimate the skill involved. It just seems so simple: get good cards and rake in the dough. Or bluff everyone blind and rake in the dough once more. Either way, you’re raking it in. It seems like every time I talk to Erik he has a new story of a bartender or server or Uber driver who recognizes him and offers up the wisdom that he could play just as well; he’s just never gotten the chance to do so. That “lucky break” simply hasn’t manifested itself. But maybe if Erik just stakes him for that big game …

And poker does have an element of chance, to be sure—but what doesn’t? Are poker professionals “gamblers” any more than the man signing away his life on a professional football contract, who may or may not be injured the next week, or find himself summarily dropped from the team in a year because he failed to live up to his promise? We judge the poker player for gambling; we respect the stockbroker for doing the same thing with far less information. In some ways, poker players gamble less than most. After all, even if they lose an arm, they can still play.

But the misperception is ingrained in the popular mind for one simple reason. Unlike, say, Go or chess, poker involves betting. And betting involves money. And as soon as that enters the picture, you might as well be playing craps or baccarat—games that truly are gambling. And so I tell my grandmother the words that I’ve come to repeat so often they are like my own private mantra: in poker, you can win with the worst hand and you can lose with the best hand. In every other game in a casino—and in games of perfect information like chess and Go—you simply must have the best of it to win. No other way is possible. And that, in a nutshell, is why poker is a skilled endeavor rather than a gambling one.

Imagine two players at a table. The cards are dealt. Each player must look at her cards and decide whether or not the cards on their own are good enough to bet. If she wishes to play, she must at minimum “call” the big blind—that is, place as much into the pot as the highest bet that already exists. She may also choose to fold (throw out her cards and sit this hand out) or raise (bet more than the big blind). But who knows what factors she’s using to make her decision? Maybe she has a premium hand. Maybe she has a mediocre hand but thinks she can outplay her opponent and so chooses to engage anyway. Maybe she has observed that the other player views her as conservative because she doesn’t play many hands, and she’s taking advantage of that image by opening up with worse cards than normal. Or maybe she’s just bored out of her mind. Her reasoning, like her cards, is known only to her.

The other player observes the action and reacts accordingly: if she bets big, she may have a great hand—or be bluffing with a bad one. If she simply calls, is it because her hand is mediocre, or because she’s a generally passive player, or because she wants to do what’s known as “slow playing”—masking an excellent hand by playing it in a restrained fashion, as Johnny Chan did in that 1988 WSOP matchup with Erik Seidel? Each decision throws off signals, and the good player must learn to read them. It’s a constant back-and-forth interpretive dance: How do I react to you? How do you react to me? More often than not, it’s not the best hand that wins. It’s the best player. This nuance, this back-and-forth: this is why von Neumann saw the answer to military strategy in the cards. Not because everyone is a gambler, but because to be a winning player, you have to have superior skill, in a very human sense.

Indeed, when the economist Ingo Fiedler analyzed hundreds of thousands of hands played on several online poker sites over a six-month period, he found that the actual best hand won, on average, only 12 percent of the time and that less than a third of hands went to showdown (meaning that players were skillful enough to persuade others to let go of their cards prior to the end of the hand). In mid-stakes games, with blinds of 1/2 and 5/10, there were some players who were consistent winners, and as stakes went to nosebleed—50/100 and up—the variability in skill went down significantly. That is, the higher the amount of money for which people played, the greater their actual skill edge. When Chicago economists Steven Levitt and Thomas Miles looked at live play and compared the ROI, or return on investment, for two groups of players at the 2010 WSOP, they found that recreational players lost, on average, over 15 percent of their buy-ins (roughly $400), while professionals won over 30 percent (roughly $1,200). They write, “The observed differences in ROIs are highly statistically significant and far larger in magnitude than those observed in financial markets where fees charged by the money managers viewed as being most talented can run as high as three percent of assets under management and thirty percent of annual returns.” Success in poker, in other words, implies far more skill than success in that far more respectable profession, investing.

Of course, the rationale goes much deeper. Betting—that bête noire that seems to be such a stumbling block for even rational minds when you try to explain the skilled nature of poker—is actually at the heart of what makes it superior to almost any other game of skill: betting on uncertainty is one of the best ways of understanding it. And it is one of the best ways of conquering the pitfalls of our decision processes in just about any endeavor. It doesn’t take a gambler to understand why. In his Critique of Pure Reason, the German philosopher Immanuel Kant proposes betting as an antidote to one of the great ills of society: false confidence bred from an ignorance of the probabilistic nature of the world, from a desire to see black and white where we should rightly see gray. From a misplaced faith in certainty, the fact that to our minds, 99 percent, even 90 percent, basically means 100 percent—even though it doesn’t, not really. Kant offers the example of a doctor asked to make a diagnosis. The doctor reaches a verdict on the patient’s malady to the best of his knowledge—but that conclusion isn’t necessarily correct. It’s just the best he can do given the information he has and his experience in this particular area. But will he tell the patient he’s unsure? Maybe. But more likely, if his certainty reaches a specific threshold—a different one for different doctors, to be sure—he will just state his diagnosis as fact.

But what if he had to bet on it? “It frequently happens that a man delivers his opinions with such boldness and assurance that he appears to be under no apprehension as to the possibility of his being in error,” Kant writes. “The offer of a bet startles him, and makes him pause.” Now that he has something real at stake, he has to reevaluate just how sure of a sure thing his opinion really is. “Sometimes it turns out that his persuasion may be valued at a ducat, but not at ten,” Kant continues. “If it is proposed to stake ten, he immediately becomes aware of the possibility of his being mistaken.”

And what if the bet is even higher? Suddenly, we have a corrective for many of the follies of human reason. “If we imagine to ourselves that we have to stake the happiness of our whole life on the truth of any proposition, our judgment drops its air of triumph, we take the alarm, and discover the actual strength of our belief,” says Kant. Would you bet your entire net worth on an opinion that you’ve just spent hours confidently offering on social media, broaching no possibility of being mistaken? Would you bet your marriage? Your health? Even our deep convictions suddenly seem a lot less certain when put in that light.