On Conversations with Tyler
An attempt at a contextual guide / unified theory of an excellent podcast
Conversations with Tyler sounds different from any other podcast because it’s led by someone who doesn’t listen to many podcasts. Tyler’s view is that audio is an inefficient medium for absorbing information. While his interviews compress as much information as possible, that’s not the point—to understand why CwT exists, you have to consider what comparative advantage (beyond ease of multi-tasking) audio can have over text.
One way of describing CwT’s purpose is this: to see whether and how experts surmount their own clichés. The more expertise someone has in their field, the harder their clichés are to notice. Their clichés may even be wholly original—the expert’s unique patterns of thought may lead them to interesting insights, but they are patterns of thought nonetheless. When experts present their insights in writing, they don’t have to depart from these patterns. In this regard, conversation has an advantage. Unfortunately, most interview podcasts, by asking predictable questions, allow experts to simply recite spoken versions of what they’ve already written—the insight becomes further clichéd by these repetitions. CwT tries to challenge experts into stepping outside these patterns.
This is why, as Tyler points out, he never asks “what the book is about.” Easy questions allow guests to travel down their usual path-dependent answers. Nor does he ask the typical “hardball” questions—experts have an equally standardized response for their harshest criticism. Instead, Tyler asks convoluted, unexpected, esoteric questions, especially to lead off the interview, to get guests out of their comfort zone.
Tyler also asks questions outside the guest’s field of expertise. Partly this is about mapping out some of the more random byways that trickled into the expert’s patterns of thought. Partly this is to see whether experts apply full intellectual effort to objects outside their direct interest (some do, some don’t). I think Tyler is curious about how big a factor generalized curiosity is to person’s success.
Experts have a stake in having answers, so at the margin they will tackle more answerable questions. Tyler often asks his guest the less-answerable questions in their domain of expertise.
Tyler will read and ask about things his guests wrote a long time ago, even their undergraduate papers. People’s memories of their intellectual development are often patchy; it’s easy to assume that we were then who we are now, especially when we’re at our intellectual peak. Confronting guests with how they thought in the past is one way of getting them to reassess how they think in the present.
Guests sometimes either do not understand or try to evade the essence of Tyler’s questions, whether by repeating something they said before, or answering a slightly different question. Paying attention to these deflections teaches you arguably the most important meta-lesson of the whole podcast: how to spot a carefully considered answer to a difficult question.
CwT’s ambience is civil, but intentionally somewhat hostile to social niceties. Tyler speaks in long, complete sentences, without filler words, in an unusual cadence. He does not banter, and he rarely laughs. When a guest says they’re nervous about being on CwT, he does not comfort them. The point is not to cow his guests, but simply to not give them easy access to the tools with which they smooth over the vulnerabilities and imprecisions of their thought process. The best guests are not vulnerable in the usual sense of telling deeply personal stories, but they are intellectually vulnerable.
Treat listener questions, especially the ones from audience members in the pre-pandemic live shows, as a yardstick. How interesting do you find them, compared to Tyler’s? How good are the answers they elicit? How do you account for the difference?
Think of Tyler as one of our foremost experts on intellectual clichés. Given the breadth and depth of his engagement with various fields, and especially in economics, culture, and history, he is uniquely capable of identifying whether a given argument (analytical or creative) is original or not. When you answer an important question, ask yourself: would I be satisfied with this answer if I gave it on CwT?