Before we get into the essay, this week we’re hosting Nigel Eccles (founder of Fanduel, valued at $31B) for office hours to talk all things consumer / sports betting / crypto. Link here. Very pertinent to the essay.
Friday the 19th at 1PM PT. If you missed it subscribe to our substacks so you don’t miss the next one!
On to the essay.
Four years ago I walked away from a guaranteed promotion at McKinsey and a $300K private equity offer to go work in gaming for a third of the salary. I moved across the country from NYC to LA, leaving behind friends and family I'd spent my entire life with. That's called going all in.
I've been fascinated with poker since I was a kid, playing games with my parents at 12, grinding through late night college sessions, studying game theory optimal strategies and probability tables. But it wasn't until I'd been in VC for a while that I fully appreciated what poker really teaches us about life. See, in chess, the "correct" move is correct regardless of outcome. In poker you can play perfectly and still lose, or play like an absolute donkey and stack everyone at the table. That gaming job led to connections that got me into venture capital, which led me to building speedrun. Which by the way, is accepting applications!
For finance jobs like VC, poker is directly applicable. You're literally betting on incomplete information. But the real value comes from applying poker thinking to life itself. Chess assumes a controlled environment: perfect information, one opponent, predictable outcomes. Life is much messier. Life is multiple players with hidden cards, changing rules, and luck that can absolutely demolish skill in any given hand. Once you start seeing life through the poker lens, you realize most people are playing chess in a poker world. No wonder they're frustrated when the "right" moves don't pay off.
So let's talk about some lessons from poker, and I'll assume if you're reading this you understand the basic mechanics of No Limit Texas Hold'em.
Probability and Process
This is the most important lesson from poker: thinking in terms of probabilities rather than outcomes. Many systems are stochastic, not deterministic. You can do everything right and still get crushed by variance.
This is the shit happens law. Even with pocket Aces, you'll lose 15% of the time against random cards. But once I internalized this, I stopped torturing myself over "failed" decisions that were actually correct. This was the biggest mental shift I had to make in "real life" because up until college, you're basically playing chess. There's a fairly well-trodden path laid out where the route to victory is clear. Study hard, get good grades, go to a target school, land the prestigious job. Checkmate. Then what?
It also helps you make peace with the past. You stop playing results-oriented games ("I should have bought Bitcoin in 2013!") and start playing process games ("What's my framework for evaluating asymmetric bets?"). You stop letting bad outcomes invalidate good decisions. Focus on the process by which you made each decision. The outcome is just one sample from a distribution of possibilities.
Table Selection
Table selection might be the most underrated life skill. In poker, you can be the 6th best player in the world, but if you're sitting with the top 5, you're the sucker. There's an old saying: "If you can't spot the fish at the table, you are the fish."
That's why I watched so many quant friends pivot to crypto in 2017. They weren't suddenly smarter or better traders. They just realized that battling retail investors was way easier than competing with quant savants for basis points. Same skills, different table, dramatically better returns.
The hard part about table selection IRL is that choosing easier tables feels like admitting weakness. There's more social status in losing at the hard table than winning at the easy one. How many people stay at McKinsey getting absolutely crushed when they could be the star player at a mid-size company? On one hand, surrounding yourself with the best people makes you better. On the other hand, sometimes you need to be realistic. You’ll have to level up or find a different game.
Bankroll and Bet Sizing
Understand how much you're willing to risk and adjust based on your conviction and the situation. In life, the bankroll isn't just your bank account. It's your time and energy, your reputation and career capital, your relationships and mental health.
For me, I've tended to be too conservative with financial bets (classic loss aversion from a middle-class upbringing) and also too conservative with relationships (worried about getting hurt, so I hedge instead of committing). Some of my friends are the opposite, consistently “madly” in love. Or onto their next hair-brained business idea. We all have those friends. Know your tendencies and how they evolve over time.
By the way, your risk tolerance should scale with your various bankrolls, not stay fixed. The bet sizes you’re making at 25 should not be the same as when you’re 50.
Variance and Time Frame
Here's where life diverges from poker in a beautiful way. In poker, variance is symmetric. You can only win what's in the pot. In life, variance is asymmetric. The right job, right investment, or right relationship can return 1000x. This means you should actually seek more variance in life than in poker, not less. You want to maximize your exposure to positive black swans. But only if you can survive long enough for the odds to play out.
That's why it's important to figure out what you want to do earlier, even if it's just directionally correct. Pivots are totally fine and happen all the time, but each pivot means starting the compounding clock over. Even for myself, I'm still hunting for my real 1000x, trusting in myself and the game to eventually deal me the nuts.
Reads and Ranges
In poker, you're not trying to guess the exact hand your opponent has. You're putting them on a range of possible hands and narrowing it based on their actions. Life works exactly the same way. People aren't single data points; they're probability distributions across multiple dimensions. Your coworker isn't "trustworthy" or "untrustworthy." They're 90% reliable on small things, 60% on confidential information, 30% when they’re under pressure.
Everyone has a range. The mistake I see is binary thinking. Someone disappoints us once, we write them off forever. Someone helps us once, we trust them with everything. That's like putting someone on pocket aces because they raised pre-flop. You need way more data points.
In negotiations, relationships, and hiring, you should constantly update your range estimates (or "update your priors" as they say in Silicon Valley). What hands could they be playing given their actions? That candidate who negotiated super aggressively: confidence or desperation? That investor who's suddenly responsive after ghosting you: FOMO or new information? Read the range, not the exact hand. You'll never have perfect information, but you can narrow the possibilities with every action.
Imperfect Information
Unlike chess where every piece is visible, poker forces you to make decisions with incomplete data. This mirrors basically every important decision you'll ever make. You'll never have perfect information about that job offer, that cross-country move, that key hire.
The key is getting comfortable making high-stakes decisions with 70% of the information rather than waiting for 95%. Because by the time you have 95%, the opportunity is gone. The startup has already scaled, the person has moved on, the market has priced everything in.
Analysis paralysis is just another form of folding every hand. Yes, you never lose when you fold. You also never win. The players who succeed aren't the ones with perfect information. They're the ones who make better decisions with imperfect information.
I've started using this heuristic: once I have enough information to make a decision that's 70% likely to be right, I pull the trigger or fold. Waiting longer is just anxiety management, not risk management.
Bluffing
The threat of the bluff is often more powerful than the bluff itself. If people know you never bluff, they'll run you over. If they know you always bluff, then they'll call you down light. The optimal strategy is to bluff just enough that they have to respect it.
In life, this translates to strategic ambiguity. Sometimes it's better to let people wonder about your capabilities rather than proving them. Sometimes you need to project strength when weak (interviewing while unemployed). Sometimes weakness when strong (negotiating when you have leverage but want a long-term relationship).
The key is being intentional about what you reveal. Your capacity to bluff is an asset. Don't waste it on small pots. Save it for the moments when strategic ambiguity can change the entire trajectory of the game.
Position and Timing
In poker, acting last is a massive advantage. You see everyone else's moves before making yours. Position is so powerful that professionals will play mediocre hands in position and fold premium hands out of position.
Life rewards position too, but people rarely think about it. The second company in a space learns from the pioneer's mistakes. The last person to make an offer in a negotiation knows everyone else's range. Sometimes there's a first-mover advantage, but often the real edge comes from moving last.
But position isn't just about acting last. The nuance is that it's about controlling when you act. Sometimes you want to lead out and define the game. Sometimes you want to check and see what develops. The power is in choosing. Let others reveal information, make mistakes, show their ranges. Then make your move.
Tilt and Emotional Control
Some of your best decisions will come right after your worst beats. Can you maintain process-focused thinking when you're down 50% of your bankroll? When you just got fired? When a relationship implodes? Most people can't. They revenge-trade, rebound-date, panic-accept the next offer that comes along.
Reading Marcus Aurelius helped me develop a framework: when I feel the tilt coming, I stop playing. Not forever, just until I can evaluate decisions based on expected value rather than emotional recovery. The best players know when they're not playing their A-game.
Counterintuitively, your worst beats often create your best opportunities. Everyone else is on tilt too. Markets overcorrect. People overreact. If you can stay rational when others are emotional, you have an enormous edge. The goal is to recognize when emotion is driving your decisions and have the discipline to step away from the table until it isn't.
Stack the Deck
The final lesson breaks poker's cardinal rule: in life, you can stack the deck. Moving to SF for tech or NYC for finance is literally rigging the game. Being in college to find a partner is maximizing your hands dealt. Building in public is marking the cards.
But once you see life as poker, not chess, you realize something. Chess has a correct answer. There's always an objectively best move. Poker doesn't. Poker is about playing your hand optimally given your bankroll, your position, and your read on the table.
This means there's no universal playbook for life. The optimal strategy for you might be terrible for me. And that's liberating. Stop playing chess, searching for the "right" move. Start playing poker. Make the best decision you can with incomplete information, size your bets appropriately, and trust the process over enough hands.
Because in the end, life rewards those who understand the game they're actually playing.
And it's not chess.
If you liked this essay then go read Annie Duke’s canonical work, Thinking in Bets!
Speaking as both a skilled chess player (2400+ online blitz) and winning live 2/5 NLHE player, and one who completely agrees with the overall message of this article, I'm surprised that I also disagree with quite a lot of points.
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First, there's a lot of good points that I agree with:
>> "Chess assumes a controlled environment: perfect information, one opponent, predictable outcomes. Life is much messier."
>> "This is the most important lesson from poker: thinking in terms of probabilities rather than outcomes. Many systems are stochastic, not deterministic. You can do everything right and still get crushed by variance."
>> "Table selection might be the most underrated life skill... The hard part about table selection IRL is that choosing easier tables feels like admitting weakness."
>> "Unlike chess where every piece is visible, poker forces you to make decisions with incomplete data. This mirrors basically every important decision you'll ever make... The key is getting comfortable making high-stakes decisions with 70% of the information rather than waiting for 95%. Because by the time you have 95%, the opportunity is gone."
>> Can you maintain process-focused thinking when you're down 50% of your bankroll? When you just got fired? When a relationship implodes? Most people can't. They revenge-trade, rebound-date, panic-accept the next offer that comes along."
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BUT there's also a lot of very weak points that I disagree with:
>> "See, in chess, the "correct" move is correct regardless of outcome. In poker you can play perfectly and still lose, or play like an absolute donkey and stack everyone at the table."
This is pretty confusing tbh. In chess, the "correct" move will lead to the correct outcome. The way computers solve for the best moves is to work backwards from the resulting game states that these moves lead to. It's actually poker where the "correct" move is correct regardless of the outcome, because the element of luck divorces results from decisions. So, I think I get what you're trying to say, but this way of putting it is pretty convoluted.
>> "Here's where life diverges from poker in a beautiful way. In poker, variance is symmetric. You can only win what's in the pot. In life, variance is asymmetric. The right job, right investment, or right relationship can return 1000x. This means you should actually seek more variance in life than in poker, not less."
This is an extremely bold claim presented with essentially no argument. What about the downside risks? In poker you can only lose the chips in front of you- in life you can lose everything. It would be far more accurate to say that the distribution of outcomes in real life has fat tails, and so you should seek variance while limited the downside tails. But this has now become "try to find free optionality", which is pretty obvious concept and not exactly a lesson from poker or chess.
>> "But once you see life as poker, not chess, you realize something. Chess has a correct answer. There's always an objectively best move. Poker doesn't. Poker is about playing your hand optimally given your bankroll, your position, and your read on the table."
I'm not really sure what this is trying to get at. Optimizing an equation with numerous constraints is still finding the objective best move- and that's what poker players try to do. Most of the article is about how to take the lessons from poker to try to make the best choices given imperfect information. A better conclusion would be "chess makes decisions with perfect information- poker doesn't."
>> Side note- the AI image at the start probably shouldn't have the player holding the deck of cards and definitely shouldn't have both numbers on the 9 of clubs facing the same way.
As a statistician, I find the poker life analogy misleading.
In poker, the expected value is strictly constrained: every hand played is governed by fixed probabilities, and the game is ultimately zero-sum, one player’s gain is another’s loss.
Life, by contrast, is neither zero-sum nor bound to a closed system. Collaboration, innovation, and compounding effects mean outcomes can be positive-sum, where everyone benefits simultaneously.