When I ask Thiel what, beyond work, gives him pleasure, he cringes slightly and says, "You know, it ends up being, um . . . it ends up being a lot of, uh . . . a lot of time, uh . . . it's mostly, uh, pretty basic, simple social things. Hanging out with friends, having good dinner conversation . . . sort of doing outdoor-hike-type stuff. It's not . . . it tends not to be . . . I don't really have any crazy hobbies. It's nothing that, um . . . it's nothing that, uh . . . nothing that insane or exciting." This may be true, but gossip items about Thiel's partying suggest a healthy dose of excitement. In June, the New York Daily News reported that firefighters were called to his apartment to rescue a group of partiers from a stuck elevator. The "full-on rager," according to the paper, featured a "not-so-hot shirtless bartender," and a source was quoted bemoaning the disappearance of the servers in "assless chaps" that had once enlivened Thiel's parties. One of the guests at the party, who prefers to remain anonymous, confirmed the majority of the account, disputing only the detail about assless chaps. "He used to have servers wearing nothing but aprons," the attendee corrected, adding, "Peter works hard, but he likes to play hard, too." (Thiel declined to comment on the event.)
All this plays into a widespread perception that Thiel is a hive of contradictions. When I ask him about that perception, he says, "I guess I'm comfortable not fitting into any precise category, and I'm not sure the existing categories all perfectly make sense."
If the seasteading movement goes forward as planned, Thiel won't be one of its early citizens. For one thing, he's not overly fond of boats, although maybe, as Friedman says, "he just needs to be on a large enough structure." Thiel characterizes his interest as "theoretical." But whether Thiel himself heads offshore or not, there's a whole lot of passion underlying that theoretical interest. Thiel put forth his views on the subject in a 2009 essay for the Cato Institute, in which he flatly declared, "I no longer believe that freedom and democracy are compatible." He went on: "The great task for libertarians is to find an escape from politics in all its forms," with the critical question being "how to escape not via politics but beyond it. Because there are no truly free places left in our world, I suspect that the mode for escape must involve some sort of new and hitherto untried process that leads us to some undiscovered country."
Until a libertarian colony can be established in outer space—Thiel is bullish on that idea, too, though he thinks the technology needs at least a half-century to develop—seasteading will have to suffice. "[It's] not just possible, or desirable," he said in an address at the 2009 Seasteading Institute Conference, "but actually necessary."
"Peter is a pretty holistic person, in his beliefs and philosophy, and you can even see that today in some of the crazy things he's doing," says Book, who finds the seasteading concept "appealing," while cautioning, "It's all well and good until someone drops a bomb on you." Thomas, the former Valleywag editor, doesn't believe Thiel should be defined by seasteading. "He puts his money into a lot of odd things," he says. "I doubt he thinks it's the future, but rather a future. Are a lot of these ideas wacky by conventional standards? Oh, yeah. But he's saying the world is better if we try this wacky stuff."
"The things that I think I'm right about," Thiel once told Wired, "other people are in some sense not even wrong about, because they're not thinking about them." And that's an advantage that Thiel intends to exploit. "There are quite a lot of people who think it's not possible," he told a crowd of true believers at the Seasteading Institute Conference in 2009. "That's a good thing. We don't need to really worry about those people very much, because since they don't think it's possible they won't take us very seriously. And they will not actually try to stop us until it's too late."