For my first 5 years of angel investing, I ranked everything. Founders, market, traction, team. But when I looked back on the data, it was all noise. So instead of fancy quantitative systems, I get much more personal mileage from a few simple heuristics today.
One of my favorites is to ask myself: how am I going to feel when the competition arrives?
I've tried other frameworks. Peter Thiel wants to invest in monopolies. Jason Lemkin from SaaStr says he invests in CEOs who are better than him. As the sort-of CEO of a little company for a few years, that one doesn't really work for me. A lot of what passes for wisdom here is moderately helpful at best, pseudoscientific cliché at worst. When something is called part art or science, I think they mean the science isn’t that good. Or they misunderstand the meaning of science. For me, I’d say my science of evaluating founders is a work in progress.
But one thing I know for certain is that if a founder has a high-quality, earned insight into a market opportunity, there will be many other startups funded to target the same market in the next 6-12 months. Sequoia, Kleiner, and Andreessen are likely each going to back one, and some of them will attract great talent.
In short, the competition is coming. And if I’m wrong about that, it just means the market wasn't there.
Now, I've had angel investments in companies where someone came to the market, and I started to worry. I've been in that category more than I'd like. And then I've had others–like BillionToOne or SendCutSend or Baseten–where competitors start to flood the market, and I couldn’t wait to watch them take each one behind the woodshed. I wasn’t a Bulls fan in the 90s, but that’s probably what it felt like.
The reason I don’t worry is always the same: they’re amazing at execution and they’re building great businesses that will compound for a long time. Oguzhan and @jimbelosic and @tuhinone are all maniacs in this department. And because they know what great looks like here, they’ve built teams full of people similarly gifted at executing on a mission.
After years of rankings that were nothing more than noise, the difference between “Oh boy…” and “This is going to be fun” is what I've come to trust.
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