He certainly started that way; his Common Lisp stuff is interesting, although I don't usually agree that it's the best approach. But as far as I know, the only technical thing he's done since selling Viaweb is ... this forum. You apply to YC for money and for contacts---exactly what dealmakers do.
I think "Hackers & Painters" was after ViaWeb as well, a book I'd consider technical. I'm sure there are more technical things he been doing since ViaWeb also.
I think the idea is that some people are naturally dealmakers, and the whole idea of YC was technical-minded people taking over the job that would normally be done by social-minded people and doing it better.
Same with artists; the ones who became famous or at least successful in their lifetime were good at making deals. And self-promotion. The ones who could not fit in socially, not so much.
