I’ve been doing angel investing for about 10 years.

I’ve probably made close to 100 investments.

But, after a few years of doing it, I came to realize it was almost impossible for me to make money at it.

🧵

Not for the reasons you may think: I have great deal flow, I have the experience to judge the quality of the team, to evaluate their tech, and to know if they were going to be adequately capitalized.

Instead, it was the type of companies I was interested in: early ones. The ones that hadn’t yet found product-market fit. The ones that didn’t yet have a repeatable scalable business model.

What I realized with these companies is that it was almost impossible to predict in advance which ones would succeed and which would fail.

In other words, it was equivalent to trying to pick which number would come up In roulette.

So… I changed my philosophy. My criteria would no longer be “who do I think is most likely to be successful” (since I didn’t think I could tell).

But rather, “who do I want to help take their shot”.

I decided it was better to invest in entrepreneurs that I thought would be the most interesting (and fun) to watch from the bleachers as they tried to turn their crazy ideas into realities.

And that, as they say, has made all the difference.

Because now, with each of my investments I hold out no great hope I'll ever see that money again, and even less see a financial windfall.

It will be more akin to the way I’m sure my mother felt when she made that first investment into Netflix.

“We’ll I’m pretty sure he's never going to make this idea work,” I’m sure she said to herself, “but I can’t wait to see him try”.