I hope he's not valuing his PTO based on the salary he's getting.
I'm a 24 year old with no college degree and I currently cost about $800 per day on contract. (Not hypothetical, billing at that rate right now.) I'd rather make twice as much money consulting, pick my own damn healthcare plan, go to whatever conferences I want without asking^H^H^H^H^H^Hbegging, and stash that much more money towards runway.
I just left a YC company myself. I would only work for a YC company because it was time for me to learn, it no longer is.
It's time for me to earn, so I'll contract until I get a business rolling.
If you approach working at a YC company like a piker, you're going to be disappointed. It's an opportunity to build up a network and learn how startups work so that you can eventually do your own thing. (IMHO anyway)
Employee equity is consistently pathetic. Not worth it.
It also doesn't seem like he's asking for what he wants. Does he not know how to negotiate? Tell the YC founders what you want.
People are really bad at getting what they want unless it's offered to them on a silver platter.
Edit: The whole post, frankly, seems like an advertisement for his irrationality with regards to the expected value of perks.