Play to Win: Meta-Skills in High Stakes Poker
On April 15th, 2011, my life fell apart. Black Friday: a day seared into the mind of every online poker player. That day, I logged online and the grim Department of Justice logo greeted me. While I slept, the Feds had shut down the PokerStars and FullTilt websites pending a bank fraud and money laundering investigation.
My stomach dropped. Half of my net worth sat wrapped up in red tape. I had no idea if I would ever see that money again. Even worse, my entire career as a professional player had changed course overnight.
Yesterday, I was a twenty-four-year-old millionaire steadily climbing online poker’s Top 20 All-Time Winners list. I was at the peak of my career: a predator sitting atop poker’s food chain. Today, I was unemployed, and my financial future uncertain. Life as I knew it changed forever.
I decided to walk away from poker, sell my possessions, and backpack around the world. So began the next act of my learning journey.
Years later, after the smoke from Black Friday cleared, I reemerged in the poker arena. My risk-taking muscles had atrophied, but now I was equipped with hidden strengths. This time, a wiser and more resilient version of myself sat at the online tables.
Along the way, I discovered an important truth: the most important skills for winning in poker are not about playing poker.
Life is the Product of Your Bets
Poker is a sandbox for life. It is a game of bets: making calculated decisions under conditions of uncertainty where the reward outweighs the associated risk. When professionals face off, poker is the farthest thing from gambling.
You might not think of yourself as a poker player, but we all think like poker players at our core.
Your life is the product of your bets. Successful bets compound on each other but a single poorly-placed bet can wipe you out completely. Our largest bets are obvious: home, partner, field of study, career, identity. But we’re constantly placing bets from the moment we get out of bed in the morning.
Every time we cross the street, we make a calculated bet that getting to the other side has enough utility to brave the odds of getting hit by a bus. Even perception is a bet. What we see and hear is our “best guess,” a synthesis of bottom-up sensory signals and top-down predictive models. Our bets are so ubiquitous and subconscious that they become invisible to us.
If you want to play to win as an investor, owner, competitor, or self-actualized human being, you must learn how to place winning bets.
I. Meta-Skills
Poker pros typically peak in their early twenties. It’s rare to see a player hold their own at the highest limits for longer than a year. Over the years, I’ve seen many players rise to stardom, only to rapidly fade out.
Today, I’m thirty-four years old. In online poker years, I’m considered old school. A dying breed. A dinosaur. And yet, I somehow manage to avoid extinction. Continuing to excel after so many years is nearly unheard of.
I’ve spent the last fifteen years studying poker’s dark matter: the hidden dimensions of the game that cannot be discovered by reading books or memorizing solutions. I’ve never considered myself one of the world’s best poker players. But I am one of the world’s most profitable.
In poker—as in life—I’ve learned that those making the most money are playing a different game.
Let’s call this the metagame. The game that transcends the conventional game. To win at the metagame, you need to develop meta-skills.
What is a meta-skill? A meta-skill is a higher-order skill that activates subjacent skills. Meta-skills act as skill multipliers, directly impacting your bottom line and overall performance.
Meta-skills exist within three dimensions of poker: Opportunities, Strategy, and Execution.
Opportunities: Increase your ability to play in lucrative games.
Strategy: Cultivate and protect your sources of relative advantage.
Execution: Perform well under pressure and maintain decision quality.
The formula for winning is multiplicative. Life is the product of your bets.
Winning is the product of your meta-skills.
Winning as Realization of Potential
Let’s say that each of these meta-skill dimensions exists on a 1 to 10 scale, where 1 = terrible and 10 = world-class. 1,000 points is a perfect score (10 x 10 x 10), so each player archetype is expressed as a percentage of a hypothetical perfect player.
Player 1 [The Expert]
Strategy = 10 [Incredibly talented player]
Opportunities = 2 [Playing in tough games]
Execution = 5 [Average execution]
Winning = 10 x 2 x 5 = 100 [Realizes 10% of potential]
Player 2 [The Shmoozer]
Strategy = 5 [Average strategic player]
Opportunities = 10 [Only plays in the bluest of oceans]
Execution = 5 [Average execution]
Winning = 5 x 10 x 5 = 250 [Realizes 25% of potential]
Player 3 [Yours Truly]
Strategy = 8 [Second-tier strategic player]
Opportunities = 8 [Makes access to good games a priority]
Execution = 8 [Optimizes performance, mostly plays A-Game]
Winning = 8 x 8 x 8 = 512 points [Realizes >50% of potential]
What’s the point? Let’s assume that all three of us are playing the same stakes. I’m willing to bet that The Schmoozer can double the winnings of a world-class strategic player. And that I can quintuple those winnings (5x!) by consistently playing at a reasonably high level in games with weaker players.
The multiplicative quality of meta-skills allows me to maintain my standing as one of the world’s biggest winners despite no longer being one of the world’s most skilled players.
This article is a distillation of everything I’ve learned playing over two million poker hands—at least, everything I can share without impacting my bottom line. I’m not quite ready to hand over the reins!
Soon, you will understand the lens by which an elite poker player views the world and makes decisions. Don’t worry, you do not need a poker background. These meta-skills can be applied to gain a competitive edge in any pursuit or profession. For a highly abstract and nuanced game that takes place almost entirely inside a player’s head, I’ve made this article as non-technical as possible.
Attention is generally counterproductive to a cash game player’s bottom line. So why speak up now? I believe that the modern approach to poker is headed towards an evolutionary dead-end. Let me explain how. Perhaps there are so-called “best practices” within your own field of play that have not stood the test of time and are no longer paying rent.
Enter the Game Theory (sub)Optimal Player
Cutty: “Game done changed.”
Slim Charles: “Game's the same, just got more fierce.”
~ The Wire (HBO)
Every tale of adventure needs a good villain. Technological progress will do nicely in this tale.
A machine-learning tornado has stormed through the poker world. Tools such as PioSOLVER can parse the entire decision tree of a poker hand, calculate the optimal strategy, and output the exact play a player should take in every situation. Needless to say, these tools have completely transformed the way the game is played.
Enter the Game Theory Optimal poker player, or GTO player for short. GTO is today’s dominant paradigm in poker. When players debate the merits of a particular poker play, the GTO solution is the gold standard by which all strategies are measured.
GTO play is a defensive strategy. If opponents realize you are making a specific play (i.e., betting, calling, or folding) too often, they can exploit you; GTO, on the other hand, converges on optimum frequencies that are balanced, making you theoretically unexploitable. This is called a Nash Equilibrium: a strategic outcome where your opponent has no incentive to deviate from their chosen strategy.
Imagine we’re playing rock-paper-scissors in Las Vegas. Perhaps the desert climate has primed you with rock-like concepts. If I realize you are selecting rock with a higher frequency, I counter by selecting paper with a higher frequency, gaining an edge. The GTO solution to rock-paper-scissors is to use a random number generator to select between the three options, each with a 33% frequency. This forces me to also randomize my selection with the same frequency. Any deviation from this equilibrium would cause me to lose money, and thus, you are unexploitable.
Thanks to the rise of GTO strategies, poker has transitioned from a game of intuitive feel to a game of detached quantitative analysis. Professional players hone their game by cranking out endless computer simulations and then memorizing the solutions. Their approach has become organized into a series of rigid, formal movements built from models. Today’s dominant paradigm is that the best way to defeat other humans is to try to turn yourself into a machine.
Memorized solutions create the illusion of knowledge. GTO players know the test answers, but fail to internalize the underlying principles required to generate those answers. It’s like knowing abstractly how to fish, but never having lined a rod before or hooked the bait yourself. This substitution of legible solutions for illegible understanding pervades our educational system. It’s all a race to the bottom.
I admit that this generation of players has a better handle on computer-based GTO strategies than I do. On paper, they have a clear advantage. They should win. But I continue to have superior results, year after year, despite playing “suboptimally” according to their models. Perhaps they aren’t so unexploitable after all.
Where their play is rigid, my play mimics guerilla warfare. Instead of playing defensively, my play is brazenly offensive. I’m constantly working to develop meta-skills that will never show up in their models. As poker is a complex system, my play is built upon dynamic systems-thinking rather than memorizing static solutions.
These players try to explain away my success as a result of luck and randomness. They say, Chris is incredibly lucky. One day, his luck will run out. He’s not qualified to play high-stakes. My response? Luck is lazy math.
It bears repeating: most people are playing the wrong game and are focused on the wrong skills. Those considered “the best” are almost never the ones winning the most.
I’m not here to be the best. I’m here to win. You should be, too.
In order to catch the big wave, you need to be in position before the wave comes.
II. Opportunities
“Every morning in Africa, a gazelle wakes up. It knows it must outrun the fastest lion or it will be killed.
Every morning in Africa, a lion wakes up. It knows it must run faster than the slowest gazelle, or it will starve.
It doesn’t matter whether you’re a lion or a gazelle—when the sun comes up, you’d better be running.”
~ African Proverb
Develop Relative Skill
Not much has changed since college. Life grades on a curve. However, the grade necessary to pass the test of survival is inflationary. The tide is continually rising and those who cannot keep pace will soon find their heads below water.
The best description I’ve seen for this phenomenon is the Red Queen Effect, named for the scene in Through the Looking Glass where Alice finds herself running faster and faster but staying in the same place. The effect states that in an ever-changing ecosystem, organisms must continually adapt and evolve, not only to gain an advantage, but to simply survive against opposing organisms that are also continually adapting and evolving.
To gain a relative evolutionary advantage, you can either race to adapt faster and faster or simply switch to a less competitive ecosystem. The latter is a more direct path to success. If you’re a little leaguer playing T-ball, you can be the league MVP every year.
Poker mimics life: relative standing is all that matters. Recreational players play for fun, rather than income, often making basic mistakes. Because they play less often and less seriously, recreationals take longer to improve their game. They are your meal ticket.
If you want to win, recognize that your absolute level of skill is much less important than where you choose to compete. When success demands superiority, if you are not the smartest in the room, you’re in the wrong room.
If skill is making the most of your opportunities, the meta-skill is to maximize your surface area of those opportunities. All poker players know the importance of game selection. However, GTO players don’t appreciate that it's the Most Important Thing.
Seek Out Blue Oceans
GTO players tend to gravitate towards the largest online poker sites. The consistent, around-the-clock action combined with GTO players’ repeatable style enhances their sense of flow, allowing for longer and more frequent sessions. However, great minds tend to think alike and blood in the water tends to attract more sharks. Thus, these “red ocean” sites have the worst ratio of professional players to recreational players and the competition is the most cutthroat.
Inadvertently, GTO players have optimized for convenience over profit. I optimize for blue ocean opportunities, exploring for ecosystems that are much less competitive. I’d rather play at less convenient times against less talented players and gain a bigger return.
I split my play across several smaller sites that are geo-fenced, allowing only American players to play. Liquidity scales exponentially with the size of an ecosystem. Less liquidity means smaller player pools and reduced stakes. On my sites, the no-limit cash games are capped at 5/10NL or 10/20NL ($1k and $2k average buy-in, respectively), compared to the larger sites which can have action as high as 200/400NL ($40k average buy-in). Action on the smaller sites can be hit or miss. However, when games do run, they are lucrative. Best of all, I get to keep these blue oceans to myself.
Combining the sites together as a portfolio, I’m able to play as many simultaneous tables as professionals on the largest sites. Many of the toughest players are located outside of the US or have no desire to play smaller games with larger action elsewhere. These players are like bloated funds, no longer able to invest in small caps because they need to put too much money to work.
I am a no-limit hold ’em (NL) specialist because it is the most popular game, with the largest addressable market in the US. Many new players learn NL first and most tournaments are NL. I am looking for my wide blue oceans. However, in Europe and some parts of the US, pot-limit Omaha (PLO) is more popular at the higher stakes. Thus, I am proficient enough in PLO to play if I find a particularly lucrative game.
Professional poker players always follow the money. Whatever form of poker the recreational player wants to play becomes our new favorite form. When new forms emerge (e.g., Short-Deck NLH 6+, 5 Card PLO, mixed games) there is a race among professionals to master that form first. Initially, the bar for relative-skill advantages is lowered and there is a “boom” in recreational players looking for a change of pace. You don’t need to be the best to win, you just need to be the best in your game.
Play More Tables and Higher Stakes
A very underrated aspect of winning is position sizing. A poker player’s win rate is multiplied by the number of hands they play and the average size of the pots they win. Thus, the most direct path to increasing your earnings as a poker professional is to increase your table count and play in higher stakes games.
A typical live poker game in a casino deals 20–25 hands per hour. Obviously, you can only play one at a time. Online, I get dealt 80–100 hands per hour, per table. I play an average of twelve games simultaneously. However, because I am playing 50x as many hands per hour, I can have a much lower win rate and still come out way ahead.
Most casual observers would assume that the higher the stakes, the tougher the game. Counterintuitively, as I worked my way up the ranks, I discovered that my win rate got larger as the stakes got larger. This effect is due to selection bias. Few pros would put that much money at risk unless they smelled blood in the water. Thus, when a high stakes game appears, you can assume that it’s worth playing. While these games attract the toughest players, they can also attract “whales”—wealthy recreational players with blank checks.
The returns of a poker pro fall on a power-law distribution. Pros can make more in a single night than they did in all their previous weeks of grinding away. If you took away the top twenty-percent of my sessions, I am a break-even player.
An incredibly lucrative game will form unexpectedly. One potential issue: the game might exist at 10x your usual stake. The wise professional will have a standing agreement with an investor in place ahead of time, prepared for these unpredictable one-time opportunities.
In the West, we tend to think in terms of cause and effect. This modernistic interpretation of ourselves as masters of the universe gives us a comforting illusion of agency. We have a compulsive need for action as a means to seize control of our domain. A challenging notion: what if the right action is no action? Do you have the discipline to wait for the necessary conditions to emerge?
Most of the time spent surfing is actually spent paddling, waiting for the precise moment to act. In order to catch the big wave, you need to be in position before the wave comes. Once you catch the wave, allow the wave to be, and let the wave carry you wherever it goes. I never know exactly when a wave will come. But I’m always in position. Always paddling.
Speed Kills
Online poker sites make their money by taking a rake, or commission fee (~ 5%) out of the pot in each hand played. This makes online poker a “zero-sum, minus some” game. To win in poker, a player must not only beat opponents but also overcome the financial drain of the rake.
Professionals will not play a game composed of all pros because the relative edges are almost always lower than the house rake. This means that a typical six-handed poker game is composed of five professionals and one recreational player. The game only exists when a potential recreational player is present. Once the recreational player loses interest, the game disappears. When the recreational player comes back, poof! the game magically reappears.
Games naturally begin and end around recreational players as the catalyst. Like a hawk, I scan poker site lobbies and empty tables, attuned to the slightest rustle in the brush. If an unknown player sits, the remaining five seats will fill with pros within seconds. A faster speed-to-sit allows me to secure more seats in profitable games and to have a better relative position to the recreational players in those games.
Poker is a positional game. Not all seats are created equal. The action moves clockwise, and money tends to flow clockwise around the table.
In each hand, the player acting last, “in position,” exerts the most control on pot size and has a massive advantage. If I am sitting to the direct left of a recreational at a six-handed table, I will have a relative position on them in 83% of hands. This seat is perhaps worth twice as much as the seat on the recreational’s right. Multiply this out across a table or two every day and you can see how shaving one second off my speed-to-sit reaction time translates to tens of thousands of dollars over the course of a year.
Maximize Deal Flow
GTO players tend to see poker as an individual pursuit where the size of the pie is fixed. In this Hobbesian universe, everything is framed through a zero-sum lens. If everyone is a competitor, every interaction becomes a competition. Knowledge is hoarded and friendship appears to be a luxurious distraction.
Maturity teaches the timeless wisdom of the Tao Te Ching: the biggest winners don’t compete. In poker, your net worth is proportional to your network. Imagine yourself immersed in the flow of opportunities. Cultivating deal flow means both expanding your awareness of profitable games taking place and finding entry points to gain access to those games.
All venture capitalists know the names of potential unicorns. All players know about the most lucrative games. But knowledge does not mean access. Poker is a continual game of musical chairs, and only five professional players will manage to secure a seat at the recreational player’s table.
A winning player constantly looks for back doors. Why wait in line when you can befriend the bouncer? I’m always forming walled gardens for gathering and sharing deal flow with other professional players. This is the best way to discover new blue oceans, identify the best times to play, and get tipped off when a particularly good game is starting.
These walled gardens are also great places to share notes on other players. Because so few hands actually make it to showdown, it takes a long time to validate assumptions about how opponents are playing. Any additional perspective or triangulating is incredibly valuable. Best of all, by participating in these conversations, I keep myself out of the hivemind’s spotlight.
A likable player who also commands respect captures the most opportunities. Recreational players play for fun and tend to stick around longer (i.e., spend more) when they’re having fun. Somehow this fails to click for insecure pros who kill the vibe by complaining in the chat about bad luck and belittling poor play. No matter how brutal the beat or suboptimal the play, my response is always the same: “Nice hand.”
Finding a romantic partner means becoming the type of person that the partner wants to date. I attract recreationals by becoming the type of player they like to play. I can’t tell you how many players sit at my table because I made an effort to say hello.
Leverage Your Reputation
Your competition has a great deal of latitude on how hard they compete against you. You must encourage other professionals to stay out of your way.
Poker operates hierarchically and fear maintains your dominant position at the top of the food chain. There is generally a king-of-the-hill dynamic where one player “holds the table” and sits alone waiting for challengers. If you’re already seated, you never miss a seat when a new game starts. You’ll also get the first couple of hands with a recreational player “heads-up” (i.e., one-on-one), which is by far the most lucrative situation.
If you’re perceived as the leader, others will follow your lead. However, if opponents think you will back down, you will need to constantly fend them off from this prime position. These battles redirect your limited attention away from more lucrative tables. However, the first impression as a respected and feared player tends to persist. If you establish dominance in your initial encounter, you reap the rewards of an exemption from future Pyrrhic victories.
If other professional players actively dislike you, they will go out of their way to hurt your bottom line, even if it hurts theirs as well. If you’re respectful and collaborative towards other professionals, they will reciprocate in kind. If there’s a good game, you want other players to let you know. If there's a marginal spot, you want other players to let you have it.
This Goldilocks zone of opponent perception is a careful balance of fear and love. You’ll know you have succeeded when your opponents are confronted with the mental superposition of both loving to have you at their table and hating to get into hands with you.
Once you’ve maximized your opportunity set, it’s time to expand beyond conventional strategies. I define “strategy” as a plan or mode of thought designed to achieve your ends by maximizing your limited means under conditions of uncertainty.
Buckle up, we’re about to get philosophical.
The infinite game is fractal.
The gameplay appears self-similar across all levels but as soon as you agree to play by different rules, you’re no longer playing the same game.
III. Strategy
“He will win who knows when to fight and when not to fight. If he is superior in strength, evade him . . .
You can be sure in succeeding in your attacks if you only attack places which are undefended.”
~ Sun Tzu, The Art of War
The human brain, the earth's climate, psychology, economics, the internet—these represent only a few complex systems. [sidebar: everything is a system.] Systemic structures are often invisible until someone points them out.
Every complex system contains leverage points—places where a small shift in one component can produce big changes in the system's state. Change one piece of a complex system and you will see its other pieces begin to change and adjust. For example, when the U.S. Federal Reserve changes inflation targets, the discount rate for every corporation adjusts to match. This singular leverage point of discount rate determines thousands of future investments in new plants, product lines, or personnel.
Furthermore, poker is a complex adaptive system. Not only is a poker game composed of many independent actors, but each player is also adapting their response to the responses of other players. Every action we take causes a reaction from our opponents. These second-order effects (and third, fourth . . .) require a holistic approach to the game where winning moves often appear disguised as losing moves.
The Map Is Not the Territory
GTO players approach poker reductionistically, basing their strategy on static models rather than dynamic conditions. As the saying goes: all models are wrong, but some models are useful. I take this notion one step further: even a hypothetical model of perfect accuracy will be flawed, as it reflects an outdated snapshot of reality.
Static models exclude underlying structure—the conditions, incentives, paradigms, and constraints which led to the emergence of this moment’s particular permutation of reality. This deterministic structure is the solid container to which all liquid human behavior conforms.
By modeling the “optimal” approach to each individual situation, GTO players miss the forest for the trees. They improve the individual pieces of their game without considering how those pieces emerge to create the whole. As in all systems, local optimizations lead to local maxima. It’s tempting to keep walking uphill and mistake an eventual plateau for the top of a mountain.
As we know from physics, the simple act of observation alters the nature of that which we measure. GTO players finally learn how to play a hand perfectly, only to discover that all the variables have shifted due to second-order effects. The very act of grasping for perfection causes it to slip through their fingers like grains of sand. The model becomes perfectly optimized only at its point of greatest irrelevance.
As the game of poker continues to evolve at an exponential pace, the half-life of models is rapidly decaying. Yesterday’s best practice is today’s glaring leak. Intimate knowledge of computer-driven models forms a dependency that becomes a crutch. I’ve seen players leave thousands of dollars of value on the table because they were afraid to leave their comfort zone and deviate from a strategy they “knew” worked.
Even worse, an insensitivity to current conditions leads players to apply these static models in the wrong context. This lesson is captured within John Boyd’s OODA Loop, my primary mental model for rapid decision-making in a complex and dynamic landscape. In a closely-matched battle, the competitor who reorients faster to changing conditions wins an outsized percentage of the time.
I optimize for the flexibility to reorient to emergent but fleeting shifts in the field of play. With my flexible approach, I am able to “get inside my opponent’s loop.” My competition increasingly operates from an outdated model of reality.
Discern Signal from Noise
Every second, the eye sends ten million bits of information to the brain. As detailed by Tor Norretranders in The User Illusion, some believe that we only have the conscious capacity to handle twenty bits of information per second. That means 500,000x more bits enter the brain than our consciousness perceives and that what we experience as “conscious thought” is primarily the discarding of information. Our minds continuously sift to find the signal in an ocean of noise.
Friends who have watched me play a session of online poker express amazement at how I keep all of the details straight. I track dozens of opponents across 12+ games and multiple screens. It breaks down to one decision on average every 2–3 seconds. I’ve heard it described as a scene from Minority Report. They assume that I am following some sort of script.
Really, it’s all intuition. What we refer to as intuition is really the accumulation of internalized experience. My intuition is a highly-factored dataset informing what I must pay attention to, and most importantly, what I’m free to ignore.
Unknown players draw my attention first. My first objective, whenever I sit down at a poker table, is to converge on a player archetype for each opponent as soon as possible. Once I converge on an archetype (e.g., tight/loose, passive/aggressive), I have a baseline for their preferred methods of reasoning and can then predict their actions.
New players mean noisier interactions. You may have only a few hands to develop a read. But, if you know what to look for, there is an incredible amount you can extrapolate from seeing how a player acts in a single hand. Here are some good questions to ask yourself when facing a new opponent.
“What does the way they played that hand tell me about their…”
Criteria for which hands are playable?
Rationale for entering pots by raising vs. calling?
Tendencies towards passivity or aggressiveness?
Preferred lines with strong hands?
Perception of good bluffing opportunities?
Every trade contains a counterparty. There is always a human on the other side of the screen, even if you can’t see them. The computer offers a lossy translation interface by which to communicate with that other person. The German word fingerspitzengefühl best describes this phenomenon. Over time, I develop a “fingertip feel” for the ever-changing needs, wants, and desires of my opponents.
Humans are emotional decision-makers. The player who shows up on a particular day can deviate quite a bit from their typical playstyle. If you know a player well, your sensitivity to deviations in play allows you to capitalize by adjusting faster to new conditions. Subtle signals can reveal that your opponent is teetering towards their emotional edge and gearing up for a major blunder.
How to discern if a player has deviated from their baseline:
What is their objective for playing (it’s rarely monetary) on this particular day?
What is their current emotional lens?
Has their appetite for risk shifted?
If they go on “tilt,” do you know the catalyst?
If you can increase your baseline level of awareness, you can harvest your intuition on demand. As you approach a level of unconscious competence, these observations will become second-nature.
Narrative Games = Compounding Probabilities
Poker is a narrative game. The four streets in a poker hand (preflop, flop, turn, and river) follow the same four-act narrative structure as a novel or play.
Preflop: Characters established.
One aggressor initiating the action (the last player to raise preflop) and one or more defenders hooked along by this inciting incident.
Flop: Conflict and rising action.
With 60% of the total information revealed, all players now have viable five-card hands. The flop’s texture (suitedness, connectedness, high/low) determines how the rest of the hand will play out. Relative hand strengths have shifted dramatically.
Turn: Crisis and rising stakes.
The pot grows exponentially larger. Made hands become either incredibly vulnerable or lock to win. Remaining hands must turn into bluffs or you must release them.
River: Climax and resolution.
All information is known. Equities converge to 100% and 0%.
I never try to put my opponent on one specific hand. Instead, I systematically eliminate the hands that our opponent cannot have. This allows me to narrow down my opponent’s range of hands. A range is my opponent’s possibility set—all the hands they could have. Not all of the hands in my opponent’s range are equally likely, so I weigh each category of hand (e.g., top pair or better, weak pair, flush draw) in that range probabilistically. I wade in this stream of possible values, my mental qubits continuously Bayesian-updating the probabilities as my opponent’s narrative comes into focus.
Poker is a game of deceptive storytelling. With every expression, pause, and action, you and your opponent are both telling stories about your hands. The actions taken must make sense at each and every point in the hand. If I am trying to bluff the river, the range of hands I am representing has to line up with everything I did at every earlier street. Similarly, if the story my opponent is telling is incoherent, I know I’m being deceived. In general, your strategic aim is to determine what your opponent is trying to get you to do (call or fold) and disappoint them by doing the opposite.
Beginners tend to approach each street in a vacuum, independent from the others. They fail to take into account the accumulating information gathered on earlier streets. In cognitive science, this is known as the conjunction fallacy, or the Linda problem:
Linda is 31 years old, single, outspoken, and very bright. She majored in philosophy. As a student, she worried about issues of discrimination and social justice, and also participated in anti-nuclear demonstrations.
Which is more probable?
Linda is a bank teller.
Linda is a bank teller and is active in the feminist movement.
Most respondents select #2, even though the probability of two events occurring together (in "conjunction") is always less than or equal to the probability of either one occurring alone.
Poker works in the same way. Limiting down our opponent’s hand range is a function of compounding probabilities. We update our opponents’ ranges given the new information we receive on each street. Thus, all players’ ranges get smaller as hands approach the river. The climax of any poker hand flows logically from the decisions made on previous streets.
Beginners tend to overweigh the absolute strength of their hand rather than considering their opponent’s perception of their hand strength. If your opponent thinks you have a strong hand and yet goes all-in, you should fold. If your opponent does not expect you to call and yet goes all-in, you should surprise him.
Exploit Information Asymmetries
In any bet, whoever has the most information has the edge. Your edge is proportional to the magnitude of this information asymmetry. There are two ways to create information asymmetries: proprietary sources of information or a superior analysis of that information.
Three types of information asymmetries exist in poker:
Situational
A superior understanding of a particular poker situation, such as four-bet pots, monotone flops, or river check-raises
Population-Level
A superior knowledge of the poker population as a whole—a well-defined archetype of how a player plays across all situations within a particular ecosystem
Opponent-Specific
Understanding an opponent’s tendencies (both strategic and psychological) better than that opponent understands your tendencies
What makes information asymmetries so powerful? Pattern recognition. All decision-making is essentially a prediction of the future. My superior analysis off the tables tells me what patterns to watch out for when I’m on the table. Like Wayne Gretsky, I skate to where the puck is going.
Years ago, when third-party data-mining tools were available, they were my biggest expense. I acquired every single hand played across the online poker universe and tore the data apart using analytical software. By studying my opponents off the tables, I surfaced situations where specific opponents had consistent and exploitable tendencies.
This software was widely available, but most players failed to utilize it to its full advantage, settling for out-of-the-box solutions. Creating custom statistics allowed me to get hyper-specific in my analysis. The more variables I can account for, the more actionable the intelligence.
A rare situation may only occur once in 1,000 or even 10,000 hands. However, this means that these situations are rarely studied, and often an opponent will take the same action 90%+ of the time without even realizing it. Since I can alter the base rate probability of these situations (see: Centrality), these long-tail situations aggregate into fat-tail profits.
Centrality: Always Play at Home
In 1996, Garry Kasparov faced off against Deep Blue, a supercomputer fed with a database of every chess game ever played. This created the ultimate information asymmetry—perfect information and perfect recall. Clearly, if Kasparov played a conventional style, he would play at a large disadvantage. What did Kasparov do to counter this? He developed new opening sequences that had never appeared before in ranked games. Escaping the known database put Kasparov back in the driver’s seat, navigating positions where he had a greater familiarity than Deep Blue.
This anecdote illustrates the concept of centrality. A key principle in all competition is to steer opponents toward situations where you have a comparative advantage. Take the field of play to where your opponent feels least comfortable. Once you recognize a weak area in your opponent's game, repeatedly force them into that situation. If your opponent can’t hit a backhand, hit it to his backhand every time.
Centrality is a measure of how common a situation is. Any situation which is highly central is easier to play. Through repeated exposure, players understand the situational dynamics really well. However, if a situation is non-central, players have less experience to draw from and are more likely to make mistakes. I deeply study these non-central situations and force their recurrence by nudging hands towards these parts of the game tree, thus magnifying my edge.
GTO players know how to play the most central situations extremely well. If you remain within the known database of “correct moves,” they will generally make very few mistakes. However, this strength also becomes a crutch that can be exploited. Because GTO players know the standard lines so well, they find themselves lost when forced to deviate from their preferred style of play.
Like Kasparov, you can shift the field of play to disorient your opponent. Consider an NBA basketball game. The home team has a massive edge which increases along with the stakes. The home team in an NBA playoff game wins 65% of the time. If you develop the meta-skill of centrality, you always enjoy the home-court advantage.
Feints Within Feints (Within Feints . . . )
The air gets thinner at the top of the ladder. In high-stakes poker, you play against the same dozen professional players every day. This makes poker an “iterated game.” In iterated games, players must take into account the impact of their current actions on the future actions of other players.
Let’s say you’re attempting a bluff. How will your opponent respond if you get caught? Will they become suspicious and thus more likely to call next time? Or will they expect you to become trigger-shy and thus be more likely to give you credit? In iterated games, second-order effects dominate your decision-making. Before I make any move, I anticipate and account for all of the opponent’s future adjustments.
This means that I must intentionally throw battles in order to better position myself to win the overall war. Like warfare, most strategies operate within the fog. Losing plays often look like winning plays (and vice versa).
A key flaw of the GTO approach is that it fails to account for these adjustments which can close future windows of opportunity. Plays that are correct within the vacuum of a single hand will lose money in the long run after opponents adjust. My goal is to continually steal my opponent’s pie without them ever realizing they left the window unlocked.
Poker forums are full of aspirant players analyzing hands played at the highest stakes. Observers hope to glean insights from this single data point on the “correct” way to play. It’s harder to imagine a less effective way to improve your game.
Any poker play can only be interpreted as a part of a sequence of adjustments. The static snapshot of a single hand lacks the necessary context (i.e. history between the players, current table dynamics) necessary for deconstructive analysis.
Professional players have one clear Achilles heel: predictability. If I know I’m playing against another professional, I can eliminate many possibilities right off the bat as plays that no professional would make. Thus, I can quickly converge upon a narrow range of hands. This is how hero calls (and folds) are made.
Every visible tactic offers an opportunity for strategic deception. For example, when the hand number ends in a certain digit (10% chance), I try to make my opponent fold no matter what. By deliberately injecting deceptive elements into my game, I throw my opponents off track.
The less predictable you become, the less often others will try to predict you.
Spoiler alert: no.
IV. Execution
"The primary thing when you take a sword in your hands is your intention to cut the enemy, whatever the means.
Whenever you parry, hit, spring, strike or touch the enemy's cutting sword, you must cut the enemy in the same movement. It is essential to attain this.
If you think only of hitting, springing, striking or touching the enemy, you will not be able to actually cut him."
~ Miyamoto Musashi, The Book of Five Rings
The third meta-skill framework is execution. Superior execution boils down to the quality and consistency of your decision-making. The best diet is a diet you stick to. The best strategy is the one you execute consistently. Remember: it’s not the quality of your A-game, but how often you can play it.
A machine playing poker would certainly play with a strong executional advantage. The machine offers consistency in abstraction, and consistency is a necessary part of optimal execution. However, what a machine can predict abstractly varies from what a human can execute in reality.
Humans are not perfect executors, so any strategy which depends upon perfect execution is doomed to fail. GTO players myopically focus on perfecting their strategy and fail to realize how seldom they can execute it reliably.
Separate Decisions from Results
To improve your decision-making, focus on your process rather than the results. When I discuss hands with other professional players, it is forbidden to say who won the hand. Instead, we limit our discussion to examining each decision point within the hand and the factors weighted most heavily in those decisions.
Results offer utility to the extent that they cast light on invalidated assumptions. If your opponent has a hand at showdown which falls within the expected range, that tells you very little. However, if your opponent shows you a hand outside of your expected range, it reveals that you missed something critical in your analysis.
Unfortunately, society hard-wires results-oriented thinking. We grow up believing the lie that the results validate or invalidate our actions. Not dying when you jump off the cliff doesn’t make jumping off the cliff the right choice. We anchor to outcomes when instead we should focus on improving our process of decision-making.
Separating your decisions from your outcomes allows you to rise above them. Harnessing this meta-skill means cultivating a stoic outlook toward results. Most players have fragile mindsets, fragile emotions, and fragile decision-making processes. Their mental states shatter with the slightest touch of variance. They start to believe a narrative of themselves as victims, creating a self-fulfilling prophecy.
Over the long run, everyone experiences the same fluctuations of luck. Remember, relative standing matters most of all. I don’t need to play perfectly when I’m running poorly—I need to avoid sinking down to a loser’s level. Losers use variance as an excuse for poor results while winners smile in the face of a new challenge. This transmutes variance from a threat into another source of advantage.
Don’t Watch the Scoreboard
Poker is a wicked decision-making environment with extremely noisy short-term results. It’s very common to play well and have poor results or to play poorly and have great results. The scoreboard can be an unreliable indicator of how well someone is playing.
When you’re playing the long game, the results of any given day, month or quarter do not matter. Recurring reporting periods (e.g., “We had a great Q2”) cause short-term diversions from our long-term objective of capital appreciation. The shorter the time horizon, the worse our decision-making. Thus, execution improves as we move away from these arbitrary periods of evaluation.
Play every single hand as if you are starting back at $0. Treat every street as an opportunity to make the perfect decision.
In trading, the best practice is to ride your winners and cut your losers early. Humans tend to do the exact opposite. When we’re losing, our tendency is to take on more risk and attempt to restore narrative equilibrium by “getting back to even.” When we’re winning, the bias is to become risk-averse and attempt to secure a win. In poker, players with a weak mental game play many short winning sessions where they leave expected value on the table, punctuated with occasional 24-hour losing binges.
The most important decision you make as a poker player is when to quit. It’s important to have a stop-loss, where you stop playing if you lose a certain amount in a session. My stop-loss is ten initial buy-ins. However, I never penalize myself for quitting early if I don’t feel like playing.
If I’m not able to play my A-Game, I’m probably not a winning player at this moment. If I’m not winning, I'm better off not playing. Live to fight another day.
There are also rare occasions where I’m both playing well and luck is on my side. These ten to twenty days a year are hard to predict but that’s when I make the bulk of my profits. On these glorious days, I clear my calendar and carry on as long as I can keep my eyes open.
Install Guardrails
In theory, it’s easy to fold your bad hands for hours on end, patiently waiting for a better spot to get involved. However, as the saying goes, “idle hands are the devil’s work.” When too much time has passed since our last profitable opportunity, we start justifying reasons to get involved. Most losing players suffer more from a lack of discipline than a lack of ability.
In investing and life, one poor decision has the power to destroy the value accumulated from many good decisions. Thus, we improve our average decision quality by raising the floor—eliminating the bottom 10% of your decision-making. Use guardrails to limit the damage when your psychological capital is low.
Portfolio managers I work with develop a pre-trade checklist they run through before entering or exiting a position, making sure they look at all the angles. A decision journal can also act as a guardrail. It forces you to explain the assumptions underlying your decision as well as present the opposite case—why would it make sense not to do this trade?
In order to learn from decisions, it’s important to do a session post-mortem to capture lessons learned and opportunities for improvement or further study.
Post-mortem prompts:
Given the information I had at the time, what could I have done to make a better decision?
What could I have known that would have changed my decision?
The more often you examine the assumptions underlying your decision-making, the less tuition you pay from repeatedly making the same mistakes.
Guardrails are an incredible meta-skill: I only play when I have the advantage. Other players dilute their advantage by playing when they don’t have one.
Raise the Floor on Performance
Your life away from the arena supports (or hinders) success within the arena. Energy, focus, discipline, feedback loops, and mental health all play integral roles to sustain high performance.
I recommend following a pre-session routine before sitting down to play. My longer poker sessions can last ten hours (~5,000 decisions) without a break, and it’s rarely clear what to expect at the outset. Thus, I always set aside a few minutes for mental and physical preparation. This helps me sustain high performance levels throughout a long session.
My pre-session routine:
Check to make sure I have everything I need on hand: water, almonds (easily eaten, calorically-dense), extra sweatshirt.
Have a full playlist chosen with potential variations in beats-per-minute in case I need to up/downshift my level of adrenaline. Music works as an emotional cheat code, inducing time dilation by enhancing my sense of flow.
Close all unnecessary loops. Eliminate distractions: no phone, block messaging and social media, no unnecessary browser tabs. Capture anything top of mind (to-dos, ideas, etc) to maximize available mental bandwidth.
Prepare my body and mind. I do a short stretching routine to counter hours of sitting and eliminate energy leaks and take some deep breaths to center myself in the present moment and gain access to metacognition.
Visualize my plan for the session. Any particular part of my game that I’d like to work on? What went right/wrong last session that I should prime my perception for? At what time does the level of action typically peak?
Open the tables currently running. Review any notes on my opponents. Where are my sources of advantage?
Some players let aspects of their lives outside the game hinder their ability to make good decisions within the game. I call these aspects “lifestyle leaks.” If you invite sources of stress, distraction, or moral ambiguity into your life, you will distort your levels of conviction and concentration.
For example, imagine a player who has a fight with his girlfriend and acts out his frustrations on the table. Or take my roommate, who once lost six figures in an evening of flipping coins and then had to drop down in limits and rebuild his bankroll from scratch. Or any use of alcohol, caffeine, or other substances. I love late nights out as much as the next guy, but when it comes to poker, my body is a temple. I don’t even want to know how much money I’ve cost myself with poor decisions which trace back to saying yes to dessert.
Lifestyle leaks can take a hidden (or not so hidden) toll on your trajectory as a player. Put bluntly, your profits are a reflection of whether or not your life is in order.
Winners do not fall for the myth of perfection. Practice stoicism by focusing on what you can control. Maximizing your ability to execute requires separating your decision-making from your results, installing guardrails, and raising the floor of your performance. Better to maintain consistency in your execution than crumble in the face of imperfection.
Playing to Win
What about you? Are you playing to win?
Or are you still playing the same game as everyone else?
Achieving outlier outcomes in any competitive field requires an approach that is both contrarian and correct. Don’t operate from the same paradigms as the rest of the herd; generate your own from first principles.
The first step to thinking outside the box is to realize that the box is completely self-created.
There is no box.
It always takes a village and a massive piece like this is no exception.
Special thanks to:
Marianna Phillips for being my co-writer. This article simply would not exist without her. Very grateful for her thankless efforts to clarify and shape these ideas into an intelligible form with an actual thesis.
Natasha Conti, Ken Friedman, and Tom White for patiently editing.
Sasha Chapin, Donza Worden, Garrett Adelstein, Jorge Phillips, Nick Drage, Leo Polovets, Nick deWilde, Devanshi Jain, Charlene Wang, Pranav Mutatakar, Lyle McKeany, Drew Stegmaier, and Nivy Jayasekar for feedback and encouragement on earlier drafts.