Never Sell a 30 Year Journey

There’s a funny little truth about startup investing that doesn’t get talked about enough: not all investors are the same.

When most people think of startup investors, they imagine big-name, patagonia-wearing, wintering at yellowstone club institutional investors—venture capital funds, growth equity, the whole alphabet soup. And that’s fair, because those are the ones who tend to make the headlines. But here’s the catch: institutional investors don’t just invest with their own money. They raise funds from limited partners (LPs)—pension funds, endowments, family offices—who expect to get their money back. Eventually.

Which means those funds come with a timer. Ten years, maybe twelve to fifteen if they stretch it. And when the buzzer goes off, they’re required to sell their stakes in your company, whether it’s the perfect time or not. Their LPs want liquidity.

Now, here’s the real problem: the biggest, most durable companies in the world don’t compound their greatness in 10 years. They take decades. We’re talking 30, sometimes 40 years of relentless compounding before the true value is unlocked. By definition, institutional timelines and founder timelines are misaligned.

And that’s where angels come in.

Unlike VCs, angel investors don’t have fund mandates. No timer. No forced liquidity. No clock ticking in the background while you’re still in year eight, sweating it out in your Series C. Angels can hold forever if they choose to. And angels who have done it for a while never have to turn on an entrepreneur - this company or the next, we can be there on the 30+ year journey.

Personally, one of my four core philosophies as an angel investor is this: never sell.

What I mean by that is simple: I will never sell my shares just because. I’ll only exit if the founder exits. My job as an angel is to back founders at their earliest, riskiest, most uncertain moments—and to stand by them for the long haul through whatever that brings. If that means I’ll still be holding shares in 30 years, so be it. If it means I die before I ever truly realize value in a handful of companies over my lifetime, that’s fine too.

Because the point isn’t to flip. It’s to align.

And this is what makes angels uniquely powerful partners for founders. Our incentives line up perfectly: we want the company to thrive for as long as possible, because that’s how we win together. There’s no artificial deadline forcing our hands.