The question I'm always asking, implicitly, is: what kind of game am I in? This matters because the optimal strategy in a one-shot game is often the opposite of the optimal strategy in a repeated game. In a one-shot prisoner's dilemma, you defect — it's the dominant strategy. In a repeated prisoner's dilemma with no defined end, you cooperate — the shadow of the future is long enough to make defection self-defeating. Most of the decisions people make badly are one-shot-game thinking applied to repeated-game situations.
Three games I am playing
Working at Autodesk while building ProPilot is a game I think about carefully. The naive framing is: I'm trading time I could be spending on my startup for a salary that funds my life while the startup grows. That's accurate but incomplete. The full framing is: I'm playing a coordination game with my future self. The constraint is financial runway, not ambition. Defecting early — leaving before I have enough funding — doesn't maximize my expected outcome, it just compresses the timeline in a way that makes failure more likely. The September 2026 target for ProPilot's seed round exists for this reason: it's the point at which the expected value of leaving exceeds the expected value of staying, given everything I know about the probabilities.
The Eigen origin story is also a game theory story. My father has been trading for 30 years. The decision to build a system on his intuition rather than starting from scratch was a minimax regret decision: the worst outcome of building on a flawed foundation is a system that loses money predictably, which is recoverable. The worst outcome of ignoring 30 years of pattern recognition is building something technically correct that misses market structure entirely, which is not recoverable in the same way. The regret-minimizing choice was to start from his intuition and let the data tell me what to keep.
Reputation is a repeated game
The meta-lesson I keep re-learning is that most situations I encounter are iterated games with people who have long memories and professional networks. Reputation is a repeated game asset — it appreciates or depreciates based on every interaction, and it's nearly impossible to rebuild once damaged. This doesn't mean never pushing hard. It means knowing when you're negotiating and when you're setting terms for a relationship, and understanding that the second activity is almost always more important.
There's a darker version of this framework that I sit with occasionally. Game theory is descriptive, not prescriptive — it tells you what agents in certain conditions will do, not what they should do. The prisoner's dilemma is a well-studied problem because it captures real tragedy: two people who would both be better off cooperating defect anyway because defection is the locally dominant choice. Understanding game theory makes you better at winning games. It doesn't always help you feel good about winning them.