The Biggest Bluff

Of course, it’s a long way between betting on your own opinions and judging someone else. When we err, we are much more tolerant than when we think someone else has gone astray. Think of the 2016 presidential election. Every media source had polls showing Hillary Clinton winning—and every media source was wrong. No one was on the receiving end of the subsequent ire more than Nate Silver. He had done such an accurate job forecasting past elections that he was practically pilloried for being so “wrong” this time around. But what exactly did Silver say? In his final poll, on November 8, 2016, he gave Clinton a 71 percent chance of winning—and Trump a 29 percent chance. Twenty-nine percent. That’s a whole lot of percent. That’s nearly a third. And yet most people saw the 71 and read it as certain. The complexity of the alternative is just too taxing to take into account every time we make a judgment. To the vast majority, 71 is synonymous with 100. Clinton is winning.

But what if you had to bet, given Silver’s estimates? Would you bet on a 71 percent certainty the same way as if it were 100 percent, place the same amount of money on each proposition? Or would you then realize that there was a more than notable margin of error? It turns out that the odds of Trump winning are roughly the same as the odds of flopping a pair in hold’em—and you only have to play once or twice to realize that the odds of flopping a pair are a far cry from zero.

Nate Silver is a poker player. In fact, once upon a time he made quite a tidy living playing online. And poker has taught him something fundamental about the nature of the world that most of us simply never bother to grasp. Poker is such a powerful window into probabilistic thinking not in spite of, but because of, the betting involved: the betting in poker isn’t incidental. It’s integral to the learning process. Our minds learn when we have a stake, a real stake, in the outcome of our learning. It’s why kids learn so much better—and remember what they’ve learned—if they know exactly how or when they’ll apply the knowledge. This is the partner element to learning probabilities from experience: not only do we understand what 29 percent feels like; we now retain that knowledge because if we don’t learn, it hurts us. If we keep betting the wrong amount, we will be punished. If we keep saying “I think I’m good here” without quantifying how often we’re actually good, we’ll lose all our money.

But in life, we normally do just that without a single thought. Why did I buy that stock? Another investor said it was good over lunch. Why did I sell that? Well, he shorted that one and that sounds right to me. We react emotionally rather than looking at the statistics: traders sell winning stocks to lock in the wins—it feels good, even though the numbers say that winners continue to go up in the short term; they hold on to losers to avoid locking in the losses—that would feel bad, even though the numbers say you should cut and run. In fact, numerous studies show that professional investors have a remarkable ability to ignore statistical information for their own gut and intuition—and that they’d often be better served not trading at all as a result.

“For a large majority of fund managers, the selection of stocks is more like rolling dice than like playing poker,” says Daniel Kahneman, the Nobel-winning economist. Not only do most funds underperform the market, but the correlation in year‑to‑year performance is incredibly low. Kahneman continues, “The successful funds in any given year are mostly lucky; they have a good roll of the dice. There is general agreement among researchers that nearly all stock pickers, whether they know it or not—and few of them do—are playing a game of chance.”

It’s a difficult lesson to internalize outside the poker table. Even people who seem like they suffer consequences, like stock traders, are often loath to admit that they were wrong in their certainties. Because the world is much messier than the poker table, it’s far easier to blame something else. It’s easy to have an illusion of skill when you’re not immediately called out on it through feedback. Poker rids you of the habit in a way nothing else quite does—and in so doing, it improves decisions far afield from the game itself.

When I’d just started dating my husband, he would often fact-check me mid-conversation. I’ve never invested anything in my life, but I did in the past have a habit of investing my statements with perhaps a bit more certainty than they warranted. “Are you sure?” he’d ask, endearingly. “I think I might want to check that.” And he would pull out his phone or a book to do just that. I got better, but I could never quite kick it. It wasn’t until I entered the world of poker that the process really sank in. I hadn’t been playing long before I found myself saying things like “Well, I’m about seventy-five percent sure.” I’d experienced the consequences of improper certainty a few too many times in my bank account—and knew that I had been the only one to blame for my bad play.

That personal accountability, without the possibility of deflecting onto someone else, is key. One specific class of lawyer, in fact, actually fares far better at probabilistic thinking than financial professionals whose jobs are more explicitly tied to probabilities: the lawyers who take cases for a percentage of the eventual settlement. You have a far higher personal stake in calibrating correctly, and so you learn to do just that. Likewise, meteorologists and horse-race handicappers: their calibration of risk is accurate because they not only deal explicitly in percentages but have immediate feedback on their performance—and no one else to blame if their estimate is incorrect.

Outside the realm of games, accurate probabilistic thinking is a rare skill. Dan Harrington, one of the greats of the poker world, left poker some years ago to start a real estate business that has performed very well. He told me the story of one hire that hadn’t gone according to plan. He’d seemed nice and qualified, but his judgment ended up leaving something to be desired; it wasn’t nearly as sharp as it had seemed during the interview process. There was a key difference between him and other employees: he had a traditional finance background; the others were connections from the poker and backgammon worlds. “My partner said to me, ‘Dan, in the future if we hire a nonprofessional gambler, just give me a swift kick in the ass,’” Dan remembers. “The successful hires understood equity and they understood the decision tree matrix that that involves, and they don’t get involved in it personally. And that comes from gambling. It’s invaluable for life.” They never hired someone who hadn’t spent some time in the world of gaming ever again.

I’d wager it’s no coincidence that the father of probability—the first person who we know of to go beyond a vision of chance as some sort of unknowable goddess, or otherwise in the purview of the supernatural—was a gambler. Girolamo Cardano was a doctor, a mathematician, a philosopher. He was part of the group responsible for the advent of higher algebra and was known for his thought-provoking prose (Shakespeare, it seems, was a fan, and it has been claimed that Cardano’s Consolation was the book originally held by Hamlet in the “To be or not to be?” scene). He also made much of his money through gambling—but gambling in a way that was foreign to his contemporaries.

Cardano had little patience for the prevailing divination methods of the day. Astrologers may claim to see the future in the stars, but, Cardano wrote, “I have never seen an astrologer who was lucky at gambling, nor were those lucky who took their advice.” Likewise, geomancy, which he called “an unstable vanity and dangerous.” (I had to look up the meaning of “geomancy.” It is divination from markings on the ground or soil.) In 1526 this was quite the outlier opinion. Remember, we’re talking about a time when people were sometimes burned to death for saying that the earth wasn’t the center of the universe. Astrology seemed like cutting-edge science.

Trusting in luck as a vague sort of higher power, Cardano realized, was a losing enterprise. It was pointless to try to divine whether there was a god or spirit or other guiding force at play. He offered another way: prediction through probabilities. He remembers the moment he realized he could make certain plays based on specific frequencies being in his favor. He’d lost a lot of money to a man who had lured him into a game with marked cards. In contemplating how to regain his belongings (he’d also lost many of his clothes and personal effects), a more mathematically minded approach came to him. He not only won back his opponent’s ill-gotten bounty but published his thoughts in the first known book on probability, The Book on Games of Chance. (It was published in 1663, long after his death.)

It just so happens that, in musing on the ways to calculate dice throws and card distributions, Cardano also wrote a description of what many take to be the earliest form of poker, primero. It wasn’t played with a full deck, and the rules of betting were somewhat convoluted, but the essence was similar to the games we have now: some cards private, some in common, and a complex interplay between representing the hand you may or may not have and interpreting the signals of your fellow card players. Primero traveled across Europe, variably termed primiera, la prime, and eventually pochen, a German name derived from the verb “to bluff.” The French took pochen and made it poqué—and soon, the game would morph into a new form.

No one knows quite when it made its way across the ocean, but it seems to have taken root, as so many national pastimes, in the muggy heat of a boring summer. It was 1803, and some Frenchmen in Louisiana had grown listless aboard a slow-moving steamship bound for New Orleans. They started up a game of poqué, which would soon spread gradually by steamboat throughout the new country, eventually becoming poker. And in a sense the theory of probability traveled apace with the game.

Cardano lamented one thing, though. Understanding probability wasn’t enough to tame the luck factor. Unless you cheated—and he spent quite some time describing how that would be possible, with crooked dice and marked cards—you had no way of winning consistently. His findings “contribute a great deal to understanding but hardly anything to practical play,” he reflected. Not entirely true, but you can see the sentiment: if you want to improve your odds, understand probabilities; if you want a sure thing, rig the deck.

Poker isn’t just about calibrating the strength of your beliefs. It’s also about becoming comfortable with the fact that there’s no such thing as a sure thing—ever. You will never have all the information you want, and you will have to act all the same. Leave your certainty at the door.

BABA ANYA IS NOT convinced. Poker may teach you that nothing is certain, but she is still positive I’m going over to the dark side. I realize that nothing I say will change her mind. She waves away all my talk of skill with a dismissive hand. She has more arguments in mind.

“But this isn’t serious,” she says. Skill or no skill, there is one other element of this whole thing that bothers her. “It’s only a game. How can you be serious about a game?” She wants me to be a professor—now that’s serious business. A real job. A skilled job.

Until it isn’t. The more I think about it, the more I start doubting just how much of a gamble-free endeavor it could be. Imagine me going down the academic path. What did I choose to study? Social psychology. Ah, but neuroscience is having a moment. I may have followed my interest, but not the job market. With whom did I study? Good luck to me getting a job in any psychology department where the Big Five personality traits are still big—I studied with Walter Mischel, and he and the Big Five are not on speaking terms. What about academic publications? Who might get assigned to review my manuscript—someone with a sympathetic ear or someone who thought my research was so much hogwash? I’m not going to get kicked out of a poker tournament for choosing a style of play that goes counter to the strategy of the bigwigs of the day and may challenge their ascendance. But if I were to go against the head of a department or hiring committee—or even one of the celebrity hotshot professors? Bye-bye, job prospects.

In many ways, poker is the skilled endeavor. The job market is the gamble. How did my job talk go? Where did I go to college? To grad school? Did I rub someone the wrong way in an interview? These details, all subject to a big dose of chance, can make or break me. At the table, I play how I play. And I rise or fall on my own merits.

“BUT WHY COULDN’T YOU have maybe played chess instead?” My grandmother talking again. “Now that’s a respectable game.”

I let out a final sigh. How I wish I could take her on a walk to Washington Square Park so she can see the actual chess players. Between the hustle and the side hustle, it’s some of the most intense betting I’ve ever witnessed. “I feel a connection to these people,” Erik tells me once, during a walk in Washington Square. “Because they’re games players. They hang out, play chess, sometimes backgammon. They get it.”

But I’m out of energy. I don’t dive into my lecture about chess being a game of perfect information and life being a game of uncertainty. And I don’t mention Washington Square. I’ll just have to get on with it and hope to prove myself along the way.

The Art of Losing

New York, Fall 2017

“If you can make one heap of all your winnings

And risk it on one turn of pitch and toss,

And lose, and start again at your beginnings

And never breathe a word about your loss …”

RUDYARD KIPLING, “IF—,” 1943

I wake up bleary-eyed, my tail decidedly un‑bushy, to the sound of the harp alarm on my phone. It was chosen to be less jarring than the alternatives; instead, it makes me hate harps with unhealthy fervor. It’s six in the morning—not a time a self-employed writer usually sees unless she has stayed up all night writing. But I need to get from Brooklyn to the Upper West Side by eight. Erik, it turns out, is an early bird. Eight was the compromise time, not the opening bid.

The lesson begins, as all New York lessons must, with lox and bagels. We’re sitting at the Fairway Market Café, and Erik is eager to hear about my progress, which has, thus far, been admittedly theoretical.

“How was the meeting with Dan?” he asks.

Dan is Dan Harrington, or Action Dan as he’s often called with a wink, for his seemingly conservative playing style. He and Erik go way back, to the days when Erik still played backgammon and the Mayfair Club was still a private poker club in New York where many of the future greats cut their teeth. It was 1979, and Erik had come up to Boston, across the river from Harrington’s hometown, for a backgammon tournament. Dan had been around the backgammon scene for some time; Erik was the newcomer, “this nineteen-year-old whiz kid,” Dan recalls. They made it to the end of the tournament: it was down to the old stalwart and the young whiz.

Dan won. “I played well,” he tells me, “and Erik just said, ‘Who the hell are you? I never heard of you before.’ Because he’s from New York, and New Yorkers have this attitude that nothing exists outside of New York.”

Erik figured out who the hell Dan was, Dan became interested in poker, and six years later they met a second time, at the Mayfair. It was the start of a lifelong friendship. Dan is now retired from the poker world—“I got too old,” he says. “This is a young person’s game, believe it or not. A miracle is someone like Erik. The fact that he continues to do this at this age is just absolutely astounding. I did it at his age, but it was a much weaker field.” But his accomplishments include the one thing everyone covets, the title of World Series of Poker Main Event champion. He can also boast a record four Main Event final tables, including a third-place finish in the year made famous by an accountant, Chris Moneymaker, winning the top prize and starting the modern poker boom, the so‑called Moneymaker effect.

Finding a good mentor is crucial to learning any new skill—and one of the things the best mentors do well is know when to delegate. It’s been decades since Erik opened David Sklansky’s The Theory of Poker, the book that first propelled him into the poker world when he picked it up on a whim in a used-book shop. And he isn’t used to taking on students, let alone those who know nothing about the game. So for the basics, he’d sent me to the person who wrote the textbook—literally. Harrington on Hold’em is a classic. Erik may not have given the basics much thought since Sklansky, but Dan Harrington had distilled them for thousands. And luckily for me, he happened to be in New York.

“I think it went really well,” I tell Erik. “I learned how to beat roulette.”

DAN AND I MEET at the Midtown hotel where he’s staying on his visit from the West Coast. I’m not sure what to expect but am pleased when he greets me wearing a white baseball cap—in all the photos I’ve seen of him, he has on one hat or another. I’ve read his books and can’t quite believe he’s willing to go through the nitty-gritty of poker with me.

We bond immediately as we head to the café for some breakfast. We both grew up without much money, it turns out. I tell him how lucky I am that my parents are supportive of this latest adventure, cheering me on despite the financial risks, but confide that my grandmother has slightly different views.

And he tells me that those views may never change, no matter what I do. He recalls the moment he told his mother he won the World Series of Poker. “Well, what do you think, Mom? I won a million dollars. I’m world champion of poker!” he remembers telling her. And she replies, “Oh, that’s great, Danny. You know, we have a cousin, Pádraig Harrington. He’s a golfer, and he just won eighty thousand dollars over in the Spanish Open.” Dan persists. “Mom, I won a million dollars. I’m world champion.” And she has one answer. “Listen, Danny, he’s doing well on the European tour.”

“So what do you want to know?” he asks me, between sips on a morning coffee.

Everything, I tell him. I want to know everything.

I’m expecting a lesson in beating the odds, in calculations, in the power of position and optimal strategy. And I do get some of that—but what I mostly get instead is a crash session on the importance of failure.

“Look, you’ve read my books,” Dan says. And I have. It was the first step in Erik’s lesson plan for me, what he called the foundational element of my journey. Before I did anything else, I went out and bought copies of Dan’s books—and read them, pen in hand, cover to cover. Let me tell you, my margin notes would make a literature grad student pale with envy. I’ve meticulously gone through each section, highlighting, underlining, filling up pages with marginalia. I may not have known how many cards are in a deck until a few weeks ago, but this I was born for.

Erik has never taught anyone before, and his own early experience is not particularly applicable to me—I don’t have any current plans to stop everything and start spending all my time at the modern equivalent of the Mayfair Club, butting heads with the best players in the world for days on end. What’s more, the world of poker has changed a great deal since he came up. For one thing, there’s online poker, which means you can get more experience in less time than ever before. For another, there are powerful computer algorithms that help you work out strategies and run millions of simulations in seconds to answer strategic questions that used to be approached by the brunt of sheer repetition and experience. Dan’s books are the closest thing he can think of as a primer to everything—a way of setting up the basis of my journey without overwhelming me from the beginning.

“At least I think they’ll be OK for you,” he says at first. “Let me know how it’s going. If it’s too hard, we’ll think of something else.”

Through the waning days of summer and into the early fall, the margin notes are my life raft. They are the only thing I have that is concrete—and my only sign that I am learning anything at all. Erik has been clear from the beginning: certain markers have to be met before I can move forward in my poker journey. If I’m to work with him, I can’t skip steps. First I read and watch—read Harrington, watch streams with real hands being played by the best players. (“Sign up for Run It Once,” he tells me early on. I find out it’s a coaching site, and when I start looking at the library of available topics, I suddenly feel very, very lost and very, very small and very, very silly. What was I even thinking? What in the world is a merged three-betting range and why does turn bet sizing on three-flush boards merit multiple hours of conversation?) Then we discuss—I ask questions and Erik determines that I have enough of a theoretical basis to get started playing without completely losing my shirt. Then I begin to play for real—online, for tiny stakes, but for real money, to see how I do in putting the lessons into practice. Play money simply won’t cut it. Plenty of people who kill at Monopoly would make terrible real estate agents. Only after I start consistently winning money online will I get to do the thing I thought I’d be doing right away: going to Vegas to play in real life—somehow, online doesn’t feel like real life even though the money is real enough—in real casinos, at real tables, with real chips. (I’ve already bought my very own chip set in preparation. I’ve seen the videos, after all, and everyone knows how to do that thing where you mix two stacks of chips into one with your hand. Riffling, I find out it’s called. The first time I try it, the chips fly all over the room in a flurry of red and green. I quickly find a YouTube tutorial and start to practice. “Maybe focus on learning to play first,” my husband gently suggests when he happens upon me devoting a little too much attention to my new dexterity challenge.)

Even from Vegas, it’s still a long road to the WSOP. The Main Event is a $10,000 buy‑in. That’s high stakes for an amateur who knows nothing. If I’m not prepared, it will be the rough equivalent of taking the bills and using them as kindling for a really lovely bonfire. A beautiful experience of warmth and color, quickly followed by ash and a slightly unpleasant odor of smoldering wet coals in the air. Erik is nothing if not responsible. And he takes his role as mentor quite seriously. If I want him to be my coach, I have to agree that he will not be letting me anywhere near a $10,000 tournament, book or no book, if he doesn’t feel I at least have an outside chance at success. For that to happen, I have to get to the point where I’m consistently cashing in lower-stakes tournaments, working my way up from the smallest to the bigger ones.

It’s already September. The Main Event will be in July. That’s ten months—a bit under a year. And I’m not even to the point of having played a single hand in an actual game, live or online. So I’m holding on tight to those Harrington books. If I read them closely enough, I’m hoping, they’ll provide enough of a boost that the rest will go quickly and smoothly. It doesn’t bode well that it’s taken me far longer to get through them than I’d planned—it’s a new language for me, just as Erik told me it would be—but I remain the endless optimist. At least when I have a book deadline to hit.

And so before I ever met Dan in the flesh, I not only read his books. I reread his books. I dissected his books. Erik and I have spent multiple sessions, over multiple weeks, going through my notes and questions one by one to develop a working base of how to play. These haven’t been your traditional lessons. We don’t sit and review. There are no lesson plans. There are no specific topics to cover or goals to hit. Instead, we walk. Erik is a big walker. Ever since he got a Fitbit, some years ago, he has been religious in hitting his daily step count, and as I will learn, walking is a big part of his routine, come rain or shine, in New York or Vegas or anywhere else in the world, whether he’s in between playing or in the middle of a tournament. It’s not just for exercise. It’s his way of thinking, his way of reflecting, his way of relating, his way of learning.