Seems like a lot of the things he finds funny are because he's a suit, and has always been a suit. He always gets modded up by the former reddit/current YC news community, and I've never figured out why, since normally the same people seem to be anti-suit.
I thought most of them were funny too. Startups are basically comedies, or at least seem so in retrospect. One thing I've learned from YC is that practically all startups are broken in some way, no matter what face they show to the world. And novel kinds of breakage are the basis of humor.
I've been seriously waiting for a Scrubs-style primetime comedy on startups and/or Silicon Valley-esque entrepreneur culture. Maybe one of these days, I'll get a pilot-writer and pitch the idea to a network...