Six Big Bets

Summary

Six Big Bets Sunday December 14, 2025 [blog, startups] You don’t get to take unlimited big bets in a single lifetime. You get a small number of windows where risk tolerance, energy, capital, and conviction align. In The Black Swan Nassim Taleb frames this as asymmetric exposure to unlimited upside with limited downside. And startups are one of the clearest modern mechanisms for that kind of asymmetry. But what’s often missed is that these opportunities are finite. You can’t swing endlessly. Most of life is spent accumulating the resources—knowledge, capital, relationships—that make the next swing possible. What follows are six moments where those resources briefly line up. Age 18: Naïve Conviction At 18, ignorance is an asset. You don’t know what you don’t know, and that shields you from fear. You have time, energy, and a willingness to look foolish. This bet works disproportionately well for people with social or financial insulation from their family background because the downside is cushioned. Confidence and perseverance substitute for experience. You don’t necessarily understand all the markets, distribution, or incentives yet. But you have belief, speed, and obsession. You don’t need to be exactly right. You need to start. Examples Mark Zuckerberg (Facebook): built at 19 with no understanding of regulation, media, or power—and that ignorance enabled speed. Vitalik Buterin (Ethereum): early twenties, no fear of tackling foundational systems. Age 23: Facing Reality By your early twenties, you’ve had your first real exposure to how institutions work, usually through a job, or a failed first attempt. You now see the mismatch between incentives and outcomes. You still have energy, but now it’s paired with context. You start to notice obvious inefficiencies and think, “Why does it work this way?” This is often the first moment when external capital pays attention. Early traction here signals not just an idea, but founder trajectory. Examples Brian Chesky (Airbnb): p...