It's also worth noting that Tyler is an uncommonly good interviewer, largely because he asks very good, and unique, questions (see https://conversationswithtyler.com/). I suspect these two skills are related.
Agreed, and he asks unique questions not only because he's got an unusual turn of mind, but because he does (or seems to do) an enormous amount of prep work for each interview. Some of my favorite moments on that show are when he asks a subject something related to an old blog post they wrote on a personal topic, or a paper they contributed to as a grad student, and they're like "wait, you know about that?"
I think it's even better the other way around: he has a knack for coming up with counter-intuitive explanations, or re-framing problems or issues in a way that is illuminating or goes against conventional wisdom. Like about healthcare for example.
Could you expand on (or link to) that healthcare re-framing? Thanks!
He does but it’s only partly due to his omnivorous interests and mostly due to the fact that he does a boatload of research on the interviewee, so there’s hard work involved too. (he reveals this in a meta episode)
The episode with John McWhorter is my favorite example of this - McWhorter is audibly delighted by Cowen's questions about linguistics.