Startups are poker, not chess

Many founders treat startups like chess—thinking there’s a perfect move if they just plan ahead. But startups aren’t chess, they’re poker.

In poker, uncertainty is the norm. You make decisions with incomplete information, weigh probabilities, and manage risk. The best founders do the same. But many fall into these three traps:

Mistake 1: Trying to Eliminate Risk

Some founders overanalyze, searching for the "right" decision as if one exists. But in startups, even great choices can lead to bad outcomes. The goal isn’t certainty—it’s making smart bets with the best available data.

Mistake 2: Betting the Farm Too Often

At the other extreme, some founders think bold bets are the only way forward. But great poker players don’t go all-in every hand. They make small, calculated bets, gather insights, and double down when the odds improve.

Mistake 3: Judging by Outcomes, Not Decision Quality

You can play a poker hand perfectly and still lose. The same goes for startups. Many founders (and investors) judge decisions based on results instead of the quality of thinking behind them. The best founders focus on making high-quality decisions, regardless of short-term wins or losses.

Play the Right Game

Startups are uncertain, messy, and full of unknowns. The best founders don’t seek perfect plans or take reckless swings—they manage risk, play the odds, and refine their strategy over time.

If you want to win, stop playing chess. Start playing poker.