That's true, but he's also risking his reputation (and his paycheck) if he doesn't shop around for later stage investors for his companies. This kind of thing

That's true, but he's also risking his reputation (and his paycheck) if he doesn't shop around for later stage investors for his companies. This kind of thing is his job, it's what Y Combinator exists to do. When one of his companies looks like it's going to be successful, he has to do this kind of stuff to actually get a return out of it. Which, again, isn't to denigrate him at all. He's obviously very good at what he does and deserves a lot of respect for it.