Not to mention he got the Thiel Fellowship. That right there would make a good majority of undergrads drop out (I would at least). Thiel Fellowship is basically security in the valley because of the network it gives.
Isn't the whole point of the Thiel Fellowship to pay kids to drop out? Thiel is trying to prove some point about academia, but, as you say, it stacks the deck because the fellowship includes a lot of the connections and foot-in-the-door help that its recipients would otherwise get in university.