I spent part of my professional life playing poker for a living. A few of the lessons stuck, and I still use them in product leadership and when working with startups.
The biggest one: you can make the right decision and still lose.
You can put your money in with the best hand and watch the river complete some ridiculous draw. Same thing in business. You can correctly identify a real customer problem, build the right solution, and still watch the launch fail because of timing, competition, or pure bad luck.
The reverse is also true. Terrible decisions sometimes produce great results.
The real danger is judging the decision by how it turned out.
1. Separate decision quality from outcome quality
Poker players call it resulting: deciding whether a decision was good based purely on the result. It’s just as common in business.
A feature ships and adoption explodes. We congratulate ourselves on the strategy. A launch flops. We start questioning everything. But a successful launch doesn’t automatically mean the reasoning was sound, and a failed one doesn’t prove it wasn’t.
What matters is what you knew at the time, what assumptions you made, and whether the decision was reasonable given the information available.
Outcomes are still useful. They’re feedback. They help you update your thinking. But there’s a difference between learning from an outcome and letting it rewrite the quality of the original decision.
Good decision-making is a process. Winning is an outcome. You need the first if you want better odds of the second.
2. Expected value beats emotional hope
At the table, you don’t put chips in just because you want to win the hand. You look at the pot odds, your equity, the range of hands the other player could have, and the cost of continuing.
Sometimes the correct move is to fold a hand that still has a chance of winning. Not because you’re scared of risk, but because the price is too high relative to the expected return.
In business, we struggle with the equivalent. We keep chasing a prospect because we’ve already spent time on the conversation. We build a custom feature because a potential customer said it might lead to a deal. We keep funding a roadmap item because we’ve already sunk months into it.
Instead of asking “Does this still make sense?” we keep asking “We’ve come this far. It has to work.”
That’s hope dressed up as strategy.
A cleaner approach is to look at the expected return against the full cost: engineering time, opportunity cost, sales effort, and the actual probability of getting the outcome you want. Sunk costs are gone. The only decision that matters is what to do with the resources you still have.
Knowing when to fold is as important as knowing when to commit.
3. Protect your bankroll. Protect your runway.
Professional poker isn’t just about making +EV decisions. It’s about surviving the variance that comes with them. Even strong players go through long losing streaks. If you’re playing stakes that are too high for your bankroll, a run of bad luck can put you out of the game before your edge has a chance to show up.
And once you start chasing losses or making emotional decisions, a temporary downswing can become permanent.
Startups face the same constraint. Cash runway determines how many experiments you can run, how long you can learn, and how many mistakes you can afford.
That’s why I look carefully at the structure of an engagement, not just the headline number. A tightly scoped diagnostic or execution sprint with clear deliverables is often a better bet than an open-ended engagement with fuzzy returns.
The point isn’t to avoid risk. Without risk, there’s no upside. It’s to take risks you can survive, and to avoid letting one bad bet destroy your ability to make the next one.
Survival isn’t the same as success. But without survival, you never get the chance to succeed.
4. Make decisions before you have all the information
In poker, you never know the exact cards your opponent holds. You work with ranges, probabilities, the board, and the information their actions give you. You update as the hand progresses.
You don’t wait for certainty. If you did, the blinds would eventually eat your stack.
Building products is the same. Customer interviews are imperfect. Market signals are noisy. Competitors move in unpredictable ways. Even paying customers often can’t clearly explain what they need or why they behave the way they do.
Waiting for complete certainty isn’t rigour. A lot of the time, it’s just paralysis wearing a diligence costume.
The answer isn’t to charge ahead on the first signal either. It’s to make the best decision you can with the evidence you have, be clear about what would change your mind, and design the next step to generate more information.
That might mean shipping a smaller experiment instead of a full solution, testing willingness to pay before building another feature, or killing a hypothesis when the evidence stops supporting it.
The goal isn’t to eliminate uncertainty before you act. It’s to make the uncertainty manageable.
So what does it mean to trust the process?
It doesn’t mean believing things will eventually work out if you just keep going.
Sometimes the process says persist. Sometimes it says change course. Sometimes it says walk away.
It means making the best decision you can with the evidence available, understanding the risks, protecting your ability to keep playing, and updating your beliefs as new information arrives.
Even then, you won’t win every time. That’s not a flaw in the process. It’s the nature of making decisions under uncertainty.
In poker, you make the best bet you can. The next card is out of your control.
In product and business, you do the same with customers, markets, and technology.
The goal isn’t to guarantee the outcome. It’s to make better bets, survive the variance, and learn fast enough to improve the next one.
You don’t get to choose the river card. You do get to choose whether you’re making a good bet. Similarly, you can’t control the market’s response. You can control what you’re willing to bet on it.