Consider the fact that his degrees are in fields that can be learned for free on the Internet and at the library. $100k in debt for History and English? Ridiculous!
You are missing the point. Face to face relationships are invaluable and are the most important part of a good education. In liberal arts, there aren't dozens of high-quality, responsible IRC chatrooms, say, devoted to the intricacies of Nietzsche like there are rooms devoted to a single programming framework.
No, I'm not. Face to face relationships don't cost $30k+ a year. You don't have to go to school to meet people. If you're going into debt just to meet people then something is deeply flawed.
You're still missing the point. :) Repeated face-to-face conversations with experts and other students (i.e. a classroom learning environment) is not the same as sitting alone, in the middle of nowhere, in front of a computer.
I think you all miss the point. It is not about how he spend the money (in this case an education perceived to be not worth its money by a majority of you) but what he did to save this money. You could spend it on your next start-up or get inspiration to pay off your own debt by changing your living standards.
This isn't the pre internet age, though. There are plenty of people with degrees and advanced degrees you can find on meetup.com to enjoy IRL discussions with on a certain topic.