Bootstrapping and selling four small SaaS products is awesome! It's also relatively unrelated to running a YC-type startup and certainly not a qualification that should have made them drop the rule that they don't usually fund solo founders.

It sounds to me like Richie just wants to keeping doing what he's done, which is great, but it's unsurprising that YC isn't interested in that. They don't want reliable small successes, they want occasional unicorns.

I would think the occasional unicorn would be more prevalent amongst a sea of small successes than just randomly, but not sure if anyone’s done the math in this

I actually doubt it. The strategy for building and releasing a successful screen recorder app or affiliate system (two of OP's businesses) is dramatically different from the strategy for launching a unicorn, starting with the problem you decide to solve.

When you're trying to launch a small success you pick a niche that is small enough that no one is competing there yet, then build for it while keeping your costs as low as possible. There's basically zero chance of that turning into a unicorn because you picked the wrong market and aren't investing enough money in it, but there's a relatively high chance that you'll get enough customers for a modest exit or lifestyle business.

A startup with a chance at becoming a unicorn needs to pick a market that is big enough to support a unicorn, which are exactly the markets to avoid if you're trying to start a small success. Then you have to execute completely differently, spending tons of money long before profit materializes in the hope that you'll build something awesome before you run out. If you try to take it slowly and are in a good market you'll be passed up by someone who ran.

Au contraire, it is very related. Every big success looked modest initially.

The “perhaps intellectually” comment might be a clue that there’s a specific reason here behind the scenes. Or maybe not, who knows… Having gone through a lot of pitching, I think a lot of VCs really do like to see 2 founders, one technical and one business. They often don’t love having both roles in one, and the reasons can range from legitimate to cynical, but either way it’s their money to invest I guess.

I will say that having success exiting doesn’t mean people can either afford to start a new one, nor that they should spend their own money doing it even if they can afford it. I spent too much of my own money on a startup, had a successful exit, and I definitely won’t do that again.

Guess YC has a standard recipe they like to use for startups. They probably seek people who fit their recipe.