It’s a Strange Feeling When a Small Check Beats the Company You Built

Last week I wrote about the “reverse effort paradox” I’ve seen from the investor’s seat. The idea that sometimes a venture fund’s biggest winners come from those that required the least effort.

But founders can experience a version of this too. A couple of small checks they wrote ended up worth more than a decade of their own hard work as a founder.

My own start-up, Brontes, was expensive to build, hard, and dilutive. Late nights, plenty of “will we make it” days. I wouldn’t trade it.

After the sale, and before Founder Collective existed, my partners and friends pulled me into a couple of small checks, including Opower and Olo. One decision I made while making dinner.

Alex, Dan and Noah did the hard work on those companies. Olo started in 2005 and went public in 2021, sixteen years of someone else’s late nights. Opower went public too. Its a weird feeling when you make great returns for such little effort vs. the slog of building yourself.

It can make investing look easy, and building a fool’s errand. And of course, I’ve seen the reverse where founders strike out in angel investing, only to focus on building. But its a very odd feeling when your daily grind is financially small compared to a fifteen minute decision.

When I was building Brontes, angel investing never crossed my mind. We met plenty of other entrepreneurs, but we were heads down. I didn’t have the liquidity, and honestly I’m not sure I’d have thought it was a good idea. You had one bet and it was the company.

It’s so different now. More of the founders I meet angel invest while they build. One worked their tail off for years on a company that didn’t make it. Somewhere along the way they wrote a small check into what’s become one of the breakout companies of this cycle, and that check may well be worth more today than anything their own company returned.

Founders who angel invest: has a small check ever out-earned your own company? How do you think about that?