Insight

"Most of my picks were wrong"

Gene·Monday, October 19, 2026 Edition

THE LINE AT THE BAR

"Most of my picks were wrong," said the man at the end of the bar, and he was grinning when he said it. Kwame Asante, a logistics manager from outside Cincinnati, was explaining to no one in particular how he'd come out well on a stretch of investments he'd started in his late thirties. His glass was half-empty and he looked genuinely unbothered by the admission.

Outcomes in finance, and in most things that compound, don't distribute evenly across decisions. They pile up in a few places. Most of the bets don't pay. The game is whether you're still at the table when the one that does finally arrives. The danger isn't losing often — it's losing so badly on one swing that you can't participate in the recovery. Frequency is the wrong measure. What accumulates is magnitude, and magnitude is rare by nature.

Most of the bets don't pay. The game is whether you're still at the table when the one that does finally arrives.

The venture capital industry makes this visible without intending to. A fund might back twenty companies and watch fifteen return little or nothing. The math still works if one of the remaining five returns forty times the investment. Sequoia's early position in Google is the version of this that got written about — one holding that outweighed years of ordinary results across the portfolio. The structure isn't luck or genius. It's what the distribution actually looks like when you let it run long enough.

BEFORE YOU PULL BACK

Say you're sitting with a decision about whether to stay in something that's gone sideways. An investment that's down, a position that looks embarrassing compared to where you bought in. The hour before you move matters. The question isn't whether you've been wrong so far. It's whether the original reason you entered has actually changed, or whether you're just tired of feeling like you've been wrong. Kwame, for what it's worth, held through two periods where he looked foolish. He wasn't certain. He just hadn't seen a reason to leave.

Being right most of the time is a fine way to feel competent. It is a surprisingly inefficient way to build anything. The wins that change the shape of a life don't come on schedule, and they rarely come to people who needed to be right every step of the way to keep going.

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Try This

Write down your three most consequential financial decisions from the last five years — not the most frequent, the most consequential. Notice how few of them are responsible for most of your current position, positive or negative.

How?

Key Facts

*Most financial outcomes are shaped by a handful of decisions, not the average of all of them — protecting your access to those moments matters more than avoiding small losses.

*Being wrong frequently is not the same as being wrong consequentially; the size of the outcome, not the frequency, is what accumulates over time.

*Before a hard financial decision, ask what you would need to believe about the upside, not just the probability of being right — that shifts the frame from score-keeping to sizing.