Most of Fatima's Bets Were Wrong — She Won Anyway

"I'm right maybe one time in five," Fatima Osei said, marker in hand, standing at the whiteboard in her firm's back office. "I just try to make sure that one time counts for enough." She was explaining a decade of returns to a newer colleague, late on a winter afternoon, the city already dark outside.

Most scoring systems reward consistency. But certain domains — investing above all — are not scored that way. A few decisions tower over everything else, and the rest barely register. The batting average is the wrong scorecard when a single hit can score more than a hundred ordinary ones. This is not a personality trait or a philosophy. It is arithmetic. Outcomes concentrate at the tail, which means frequent small errors cost almost nothing, and the rare correct large bet changes the whole account.

The venture portfolio assembled by Sequoia Capital illustrates this in documented form: returns across their funds have been driven by a tiny fraction of investments, with the majority returning little or nothing. The math of the tail is not hidden. It is openly discussed in investor letters. What the principle demands is the psychological tolerance to keep placing bets through a long run of unremarkable outcomes, trusting that the shape of the distribution eventually does its work.

Imagine Fatima's newer colleague now, a year later, holding two options. One is a familiar, low-stakes financial move. An index fund top-up, automatic, frictionless. The other is a concentrated decision requiring real research and real nerve: an illiquid position, a longer horizon, a larger figure than feels comfortable. The first is easy to justify. The second is where attention wants to flee. Both are on the table at the same moment, and the principle doesn't say which one is right. It says that treating them as equally important is the only certain mistake. One of these will matter in ten years. The other will not.

You do not need a perfect record. You need to stay present long enough, and composed enough, that when the consequential moment arrives you recognise it for what it is and do not flinch.