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.