Managing Partner at Dragonfly Capital. Effective Altruist. Airbnb, Earn.com (acquired by Coinbase) alum. Instructor @ Bradfield. Writer. Former poker pro. Donate 33% of my income to charity.
Some of you will remember that a while back I wrote a blog post detailing an e-book that I wanted to write. It was originally titled “To the Young Professional Poker Player,” and I meant for it to be the embodiment of the most valuable ideas that I never had a chance to communicate in my career as a teacher of poker. I intended to release it freely for anyone in the poker world to benefit from.
Well, I’ve retitled it – The Philosophy of Poker, and I’ve decided that I’m going to begin releasing it chapter by chapter in this blog. The whole thing isn’t finished yet, and all of the chapters that I’ll be posting are rough drafts that I’ll later edit when I put them together in the final version. I think releasing it this way is going to give me incentive to keep to a schedule and churn this thing out in a timely manner, and I’ll hopefully be able to keep up while concurrently taking summer classes.
This is certainly a departure from the normal character of content in my blogs (and I know many of you who follow my blog have likewise departed from the poker world), but I hope you will get some value out of it, or at least enjoy it nevertheless.
Without further ado:
You picked up this book because you want to improve your poker game.
I know all too well how that goes—I’ve been there myself. When I began poker, I was always hungry to find the little secrets the pros were using to win, believing they had to be hidden away somewhere. Within these pages, maybe you hope to find some clever ways to play hands, some sneaky bluffs that no one knows about, perhaps the secret to handling aggressive players or 3-bet pots.
So here you are. You want to learn the secrets of poker. And deep down, perhaps you hope that there is some hand, theory, or principle that will make you suddenly understand what you’ve been missing, some stepping stone that will lift you up into that great arena.
I know how that goes too. But with time and experience, one learns that in the end, there is no secret. There is no moment of revelation. The way is hard, rigorous, and disenchanting, as the way has ever been.
This book will not purport to teach you a shortcut to becoming good at poker. There is no shortage of books that try to teach such things. You can seek them out if you wish, but in the end you will find after you read through those books, you will be no better of a poker player than when you began. I’ve met and known hundreds of poker players during my time as a pro, and never have I met one whose game was transformed to a high level by reading a book. That’s not the way that poker works, and it’s not the way that learning happens. The aim of this book then is not to make you better at poker. But instead, it is to make you a better poker player.
What do I mean by this?
Someone once told me a long time ago, “nobody teaches us how to be poker players.” This is true. Certainly, we are taught strategy, how to read hands, how to size bets. But to be a poker player is more than that. Being a poker player is an isolating and confusing profession. You are immersed in one of the most backward and contradictory cultures the moment you sit down at a poker table.
I began the premise of this book with one fundamental question that I asked myself. If I could go back to 6 years ago, when I was just 16 years old, beginning my exploration into this game… what would I burn to tell him? What have I learned that he needs to know? What are the most valuable ideas that could equip him for the journey ahead? This is what I want to communicate in this book.
You will not be ready to learn all of the ideas and perspectives presented here. That’s okay. I wasn’t either the first time I heard them, and I heard them many times from many different people before they were ingrained in me. Chances are, it will take someone else, maybe a year or two down the road, perhaps a friend, an opponent, a stranger telling you the same thing before it finally reaches, and changes you. And who knows, some of these ideas may be wrong for you. That’s okay. It’s part of the process. But let this book be a step in your journey, and even if it does not change your beliefs or your perspective on the world or on poker—trust that it will help, whether you agree with it or not. Trust that it is part of the process.
Everything that I write, I write because I want you to enjoy and grow from your journey as a poker player. And I want to remind you that it is in fact a journey – anyone who treats is as less is disrespecting themselves.
What is poker to you? Is it a hobby? An interest? A passion? Is it your calling? Think carefully about this. This is where it all begins.
You are on the journey of poker. But if you are at all like me—having begun it, all you can think about is the end of that journey. You want to become great. Perhaps you even want to be the best. You see, poker is a mountain, and you are standing at its foot. You want to conquer this mountain and it becomes all you can think about. You gaze up, and you see other climbers toiling their way up its side, and all the way near the peak, you can make out the shadows of those great ones who are near to the top.
You think to yourself—oh, that I could be up there! You start climbing, scrambling, kicking and scraping your way up this treacherous mountain with your eyes fixed on the peak, because that’s where you want to be in the end. Just as you play poker to become great, you climb to get to the top.
But that’s not how you climb a mountain.
The only way to climb a mountain, as any climber will tell you, is by looking where you are. By finding a rock to reach for, another for footing, and one by one, moment by moment, to climb. To climb, and to throw yourself into climbing. Looking up or down is irrelevant.
Climbing a mountain isn’t about the peak. It’s about climbing. And just the very same, the journey of poker isn’t about the end. It’s not about becoming great. It’s about the journey. It’s about poker.
So what does that all mean?
It means look where you are. Look where your next step is. Take stock. Grab hold, steady your footing, and lift yourself up. Enjoy it. One moment, one footing at a time.
Be patient. Be gentle. Let the answers come when you’re ready to receive them. But in the meantime, climb. Keep climbing, love the rock in front of you, and don’t stop until you’re ready to quit.
I wish you the best, and hope you will learn from what ever it is I have to teach you.
Let us begin with a question: what is poker?
You might say that poker is a card game, played between multiple players that involves cards and chips and positions and so on.
That’s all well and good, but we can delve deeper than that. Consider this question instead: how would you describe poker to a Martian? That is to say, how would you describe the structure of poker? Imagine you’re explaining poker to somebody who doesn’t know what cards are, or what a table is—after all, those things are only symbols. You could play poker without cards, as long as you have 52 distinct entities with four groups among them, etc.
A naïve understanding of poker is going to be fixated on the things that are on the surface of the game—the numbers on the cards, the suits, the felt table, the round chips. But all of those things are incidental; they are unnecessary to the structure of poker that underlies those things. You can have a game identical to poker that uses pebbles, or even markings written down on paper, so long as you have sufficient rules. What’s important is not the cards. What we want to learn is not what poker looks like, but the structure that governs what’s beneath the cards.
Now, if you were to think of a metaphor for the way poker works, what metaphor would you choose?
Chances are it would be something like a chess match. Perhaps a gunfight. There are a few more common ones. (Interestingly, a lot of them seem to have to do with war, which might say a lot about the way our minds work, but perhaps that’s inevitable for a competitive game.)
But let’s focus on the metaphor of poker as a chess match. What does it mean to think of poker that way? Well, it seems to explain a few things. Describing poker as a chess match suggests that poker is mechanistic. It suggests that despite all the apparent randomness and luck involved, that deep down it behaves deterministically—a game of pure skill.
To take the randomness out of poker is to take the mysticism out of it. Poker is commonly assumed to be the domain of gamblers, risk-takers, the intuitively-minded and swift of heart. But when we call poker a chess match, we turn those presumptions around. Instead, poker is meant to be analyzed, theorized about, dissected into its smallest possible chunks and then re-assimilated into a whole. It becomes the game of rationalists, mathematicians, and cold strategists.
It’s comforting to believe that, isn’t it? It’s comforting to believe that beneath all the chaos of whizzing cards and splashing chips, under all the downswings and bad beats, the tilt and the frustrations, that all the way down in the boiling heart of the thing, there is an equation or two that describes it all. That’s the idea, isn’t it? That if you had but the time and mathematical prowess, you could plug in some equation or execute some algorithm that would “solve” it all for you.
Of course, poker math is valuable. But let’s think deeply about this. What is the way that you—that everyone—sees poker, at the deepest level? Consult yourself. Do you really believe that’s how things work? Is learning poker the uncovering of a pristine, logical machine?
Is poker a chess match?
Perhaps you believe that, distilled to its essence, poker is a rational mathematical machine, and that belief is comforting. You would not be alone in thinking this way. Most serious students of poker who have learned advanced concepts have come to believe this, although probably not one of them has ever been told this outright. It is one of those ideas that is embedded deep in the structure of the way we talk about poker; it is unconsciously absorbed, like an element that is inhaled through the air. Nobody knows how or where, but somehow it’s found its way into your mind, and it makes perfect sense. Poker is a machine. A chess match. A set of equations and matrices acting itself out, over and over again, every hand, forever—or as long as poker is played, anyway.
But the reality is that poker is not a chess match. Nor a gunfight, nor a machine, nor a battleground, nor any other such thing. In fact, poker is none of the things that you imagine it to be.
Poker simply is. It is in defiance of you, and it will always be. Through your lifetime as a poker player, poker will take many different forms for you. You will formulate it consciously or unconsciously; you will imagine new shapes, metaphors, axioms, and laws of mechanics. Things will seem to work a different way; you will find new rules and laws and equations. They will keep changing and changing. And yet, poker is always the same.
I hear you say—of course poker is the same. I know poker is the same!
Ah, but you don’t! Think about it this way—first, a definition. Everybody who is a poker player has in their mind what I will call a poker schema. A schema can be defined simply as “the way you think things work.” When you are in a hand faced with a decision, or when you are trying to understand why a play or a match went right or wrong, what you consult is the set of all assumptions and intuitions you have about how poker works. Perhaps about why checkraising certain boards is bad, about what hands are too weak to valuebet, and so on—but a great deal more than that. Your schema includes all the notions you have about how the game works and what it’s like. About the way matches evolve, about what it looks like to lose or win, what variance feels like. It even includes all of the language you use to describe to use poker when you’re analyzing it from afar.
In short, your schema is the way you think poker works; it’s your internal mental model. But this schema is not static. It’s constantly changing. Every time you learn something new about the game, your schema is altered slightly. Sometimes it’s added to, or sometimes tweaked in some spot or another, and so on. Of course, your schema is not always changed correctly. You sometimes mislearn things—you might learn a lesson where there is none, or where there is a lesson you might learn the wrong one. This is inevitable in a game that involves random and imperfect feedback.
So your schema is fluid. It is constantly changing and shifting, and not always in the right way. There is a chaos beneath it too.
Now, all that being said, I must concede: you are not entirely wrong to imagine poker as a chess match. There is a sense in which it is; the realest sense perhaps, but an incomplete sense nevertheless.
Beneath all the madness, poker is a chess match. It is logical and obeys fixed rules and mathematical constructs. But we don’t have access to that. We don’t know the chess match, and we probably never will. The only thing we have access to is how we experience poker, which is always mediated through our schema. For us, the schema is poker.
There is an old but poignant story that serves well here. It’s said that a long time ago, there was a king who purchased a rare and exotic animal, an elephant, from a far away land. He summoned five blind men who’d never heard of this creature, and he asked each man what an elephant was. The first man grabbed the tail, and said “an elephant is like a rope.” The second man grabbed a leg and said “an elephant is like a tree trunk,” and so on, each man coming up with his idea from his limited perception. This is what a schema is. It is how our experiences and perceptions congeal into a singular idea of what the thing is. Of course an elephant is none of the things the men described, and it is even more than the sum of all their perceptions.
In a way, we are the blind men groping at the limbs of poker. We graze against it again and again, even over hundreds of thousands of hands, but our schema is all we can make of it. It’s the only access we’ll ever have. The utter truth is inaccessible to us; all we know is what presents itself, what we have had the luck of running our fingers over, and the picture that we’ve stitched together from our experiences.
What I mean more concretely is this—every time you try to formulate a match, or try to analyze a situation, you will be wrong. You might still win, make the right adjustment, even the right read, but you’ll still be slightly wrong. Wrong about what, that will depend, but the fact is that reality will be shaped differently from the one that your schema describes. It has been and will always be. Since the day you started playing poker you had some schema of how the game worked, and ever since then without fail it has changed, day after day after day, and it will change again. Even the best players in the world sometimes play matches that challenge their schema of poker.
As a poker player, you doubtless want to think of yourself as a student of logic and mathematics. You imagine rationality to be the mortar with which you build your glorious fortress of poker. For this, you can be forgiven. But in your imaginations about the game, you are not wrong to say that poker is governed by mathematics and logic. But you are not.
Poker is played by humans. It is experienced and learned by humans. You are not a rational machine. The movements of your brain are not a chess match.
Despite all of that, however, I am not saying that mathematics and logic will get you nowhere, and I don’t mean to suggest that you abandon them.
Build your fortress. You have to, even if the only materials you have are the sticks and mud around you. That’s the path you’ve chosen, after all. Go on building. But know that your fortress will collapse, again and again. Know that your strongest and most steadfast reasoning will fall someday. That’s just the way your brain works. At best, you are a creature that only approximates logic and rationality. But so it is; the building must go on.
In the end, you must erect your idol to logic and reason. You have no other choice. Cast your golden calf. The god you pray to is false, but you have no choice but to build him a monument and pray to him. After all, you must have something to destroy when you come down from the mountain—which you will. You will be your own prophet, and your own heretic, again and again.
That is the journey.
Do you agree to it? Do you want to be a poker player? Then this is your path, the only one. Live and flourish in your falsehood! Look it in the eye and love it. This is the only truth: you will be wrong, always wrong. But you must keep being wrong, and keep whittling away at that wrongness, forever. That is the path. That is the climb. That is the mountain.
It is from this point that we begin and everything originates. This turn is essential. Once you understand this, you can understand the philosophy of poker.
What does this turn tell us?
You can derive many things from it, but this is the most important fruit: it teaches us that we are fallible. Well, you might say to yourself: of course I am fallible. I know that already. Everybody’s fallible.
But what I am referring to is something stronger than that. I mean more than some watered-down platitude like “everybody makes mistakes,” by which we imply some occasional errors in calculation, volatility of execution, of emotion, or whatever. Those things exist, but if that’s all you are looking for, you will miss the vastness of your predicament.
What I want to teach you instead is mistrust. Yes, mistrust. An uncommon virtue, but one you must learn. Learn to mistrust yourself. Mistrust your brain, mistrust your logic, mistrust your math, your confidence and your beliefs and your stories and your life itself. Cast doubt over it all, imbue everything with a shadow longer than the thing itself. Become the sun. The power of the sun is not in the brightness it casts, but in the shadows it reveals.
In more actionable terms—self-doubt is the most important ability for a student of poker. But self-doubt not in the sense of being timid, or wishy-washy. Those traits have no place in a poker player. What one must have is a confident self-doubt, a powerful mistrust the parts of oneself that ought not to be trusted.
You might ask: well, what parts of yourself are you supposed to mistrust?
I will get to that soon enough. But first, we must focus on the fundamentals. You cannot build a fortress until you build a foundation, after all. But in exploring this foundation, what I won’t be doing is looking at the individual pieces of wood that go into building it. That is, I won’t be coming up with stock hands to analyze or enumerating preflop opening frequencies. All of that is secondary, and ultimately derivative. What I will do instead is focus is on the question of how one constructs a poker game on the whole: what I call holistic poker theory.
Hey guys, My summer classes have just begun. I’m taking a full load in the summer since my goal is to graduate by the end of the year, so my schedule has been really intense. Basically, I’m waking up at 7am every morning, writing in the library in the morning for a few hours on my book, going to class from 11-5PM, then coming home to eat dinner, work out,...
Hey everyone, Sorry for being slow to update this blog. It’s somewhat lame of me, I know, but I’ve been tremendously busy this last month. I was slogging through finals and finally finished this first semester, was working through the month of free mental coaching, and a slew of other things in my personal life – I started working with Habitat for Humanity (it’s a volunteer construction gig, which is...