I have plenty of investments that I wish I'd never made. But the model is to lose money on a lot of investment... — Sam Altman

I have plenty of investments that I wish I'd never made. But the model is to lose money on a lot of investments and then make 1,000X or 10,000X on an investment.

Author: Sam Altman

Insight: Most of us are taught to avoid failure at all costs—to be careful, calculated, to minimize losses. But this quote flips that completely: the path to real wealth or success might actually require losing money regularly. Sam Altman is describing what venture capitalists know intuitively but what feels counterintuitive to most people: sometimes you have to make bad bets to find the extraordinary one. The thing that makes this unsettling is how it challenges our everyday instinct to be "right." We want a track record of good decisions. We want to feel smart. But if you're only ever investing in sure things, you're probably missing the transformative opportunities—the ones that sound crazy before they work. This applies beyond literal money too. If you're never willing to look foolish at work, pursue a weird passion project, or risk a conversation that might go nowhere, you're essentially optimizing for comfort instead of growth. The hidden part here is that this mindset only works if you have the runway to absorb those losses. That's the real inequality buried in this quote. But even within whatever constraints you face, the principle holds: sometimes you have to be okay with being wrong several times to get one thing spectacularly right.