He's teamed up with Professor Charles Murray to make some fine points. I will of course make the points in my own way.
Higher education must be overpriced. The cost is rising several times faster than inflation. What is most of the money for? Needless amenities, bloated and self-indulgent administrations, and overpriced tenured professors.
A really bad way to start out in life is saddled with debts. Your options are limited, and you, of course, lack the freedom to take entrepreneurial risks. You're pretty much stuck with getting the highest paying job you can, that is, join the mediocre herd in some corporation or such.
If college is primarily about liberal education (or philosophy, literature, and such), then too many people are going. According to Murray, most people just don't have the IQs to think both abstractly and precisely enough to appreciate the finer points of language and logic. The so-called liberal education or "general education" students now receive is a kind of senseless torture. And the efforts to "engage" the average guy is dumbing down such education in a way that makes it equally boring to the few who could benefit from it.
If education, in most cases, is about learning technical skills, to prepare people for the kinds of work available to most people in a high-tech, middle-class democracy, then why pay big money to study at a brick-and-mortar university? The person majoring in exercise science or public relations or beverage management or even elementary education could pick up what's needed in a couple of years. And most of what is needed, in such cases, could be delivered online.
It's difficult to say that, in most cases, the "residential experience" is actually good for students these days in terms of developing personal responsibility and the other features of moral virtue. The dorms are "state of nature," and lots of safe yet otherwise irresponsible sex is going on in a way that it just can't in real life. This is especially corrupting for both men and women in different ways at most liberal arts colleges. The gender imbalance makes men vain and silly (or vainer and sillier) and women are stuck with the rigors of the artificially competitive marketplace. Classes are too easy; nobody flunks out anymore. Students are catered to like consumers. They don't have to do much for themselves—like cooking or cleaning. (Most of this is not true of my school at all, but we're better than most.)
Not only that: Students aren't becoming in any sense literate in ways that would benefit them as citizens, parents, and so forth. We've punted for the most part on cultural literacy and civic literacy and theological literacy and even personal finance literacy.
It's always been the case that many genuine geniuses haven't gotten much out of school. (Steve Jobs!) And those who are, in my opinion, the very best and deepest American authors of the 20th century—such as Walker Percy or Flannery O'Connor or Shelby Foote or William Faulkner—didn't learn how to read and write in college. Percy majored in medicine, O'Connor boring, textbook sociology, and Foote and Faulkner dropped out. That's surely why Thiel is giving fellowships for such people to drop out. (Actually, that's not why he's giving them; he's creating the impression that the highest human type is the entrepreneur.)
Certainly professors have become too risk-averse and careerist, saddling themselves for no good reason with autonomy-sucks such as measurable learning outcomes and student evaluations. Professors, more than ever, are stuck with being agreeable and productive in depressingly conventional ways. One piece of good news is that they may be less absent minded; the bad news is that college is becoming progressively more technical and less philosophic or genuinely liberating.
In order to facilitate discussion, I'll leave the case in the other direction mostly for later. But one thing now: What makes Thiel more interesting than even Steve Jobs is his serious interest in the philosopher Leo Strauss, one of the most impressive thinkers of the 20th century.
What interests Thiel about Strauss—who flourished in the very rigorous and aristocratic German educational system and received an old-fashioned German doctorate—is his candid and deep exploration of what's required for genuine human liberation. (A whole separate, pro-American post could be written on why Strauss was, nonetheless, a misfit in the German university system but flourished in ours.)
So Thiel says that the Straussian issue is the libertarian issue. But, for Strauss, liberation doesn't mean freedom to "do your own thing." It depends on a huge amount of education. Thiel is a pretty competent amateur Straussian, but his liberation level might be called fairly low from a certain view. He hasn't acquired, for example, the language skills, as far as I can tell, required to read the premodern texts—Plato, Aristotle, and such—with the care required to liberate himself from modern prejudices.
Libertarianism is a prejudice that's especially strong these days. It's true enough that Jobs dropped out of college and invented lots of amazing "i" stuff. But he wasn't liberated the way a theoretical physicist is, and just about all of those physicists needed the discipline of a Ph.D. program to know what's really going on—naturally speaking.
The lack of such liberation may be one reason Thiel sometimes seems suckered by the promises of transhumanism. Hardly any Straussians are.
For Strauss, there's the still the higher kind of liberation of Socrates. (Who admittedly didn't have a Ph.D and didn't publish.) But Socrates was no libertarian. He reminded us in most memorable and amusing ways of the self-indulgent and pretentious view of freedom that animates every permissive democracy (such as ours). That view of freedom is ugly in its self-forgetfulness, in its denial of the necessity that provides the foundation for human nobility and even philosophy.
In general: Genuine liberation requires a huge amount of conventional discipline. And in addition to the habituation that comes from a society that takes tradition and tough-minded virtue seriously, there's the need for genuinely higher liberation, which, in the West, has usually found its home in universities. Our colleges and universities may be failing us, but that doesn't mean we don't need them.
Someone might also talk about Thiel's division of human beings into the "mob" and the liberated, which he learned from misunderstanding Strauss and Plato in a certain way.