Peter Thiel's contrarian thought exercise

Mr. Thiel shows, again and again, how he likes to “flip around” issues to see if conventional wisdom is wrong, a technique he calls Pyrrhonian skepticism.

“Maybe I do always have this background program running where I’m trying to think of, ‘O.K., what’s the opposite of what you’re saying?’ and then I’ll try that,” he says. “It works surprisingly often.” He has even wondered if his most famous investment, Facebook, contributes to herd mentality.

When I remark that President Obama had eight years without any ethical shadiness, Mr. Thiel flips it, noting: “But there’s a point where no corruption can be a bad thing. It can mean that things are too boring.”

When I ask if he is concerned about conflicts of interest, either for himself or the Trump children, who sat in on the tech meeting, he flips that one, too: “I don’t want to dismiss ethical concerns here, but I worry that ‘conflict of interest’ gets overly weaponized in our politics. I think in many cases, when there’s a conflict of interest, it’s an indication that someone understands something way better than if there’s no conflict of interest. If there’s no conflict of interest, it’s often because you’re just not interested.”

When I ask if Mr. Trump is “casting” cabinet members based on looks, Mr. Thiel challenges me: “You’re assuming that Trump thinks they matter too much. And maybe everyone else thinks they matter too little. Do you want America’s leading diplomat to look like a diplomat? Do you want the secretary of defense to look like a tough general, so maybe we don’t have to go on offense and we can stay on defense? I don’t know.”

Maureen Dowd, NYT interview with Peter Thiel