Understanding Conversations with Tyler

I’m catching up on podcasts I’ve missed from the past few months. In the Conversations with Tyler 2021 Retrospective, producer Jeff Holmes challenged long-time listeners to put together a guide to understanding the podcast for new listeners. CWT is one of my favorite podcasts and one of only three podcasts that I’ve attended a live taping of. I want more people to listen to it, so here is my guide.

  1. This is the conversation Tyler wants to have, not the conversation you want him to have. Tyler used to say this at the beginning of early episodes, but has dropped it from recent ones. View episodes as a curious person exploring their own interests rather than someone trying to give a well-rounded introduction to their guests.
  2. Tyler wants to learn as much as he can as quickly as he can. Time is scarce. Tyler does a lot of prep work for each episode, including consuming most, if not all, of a guest’s published work, so he tends to jump right in without wasting time explaining the context.
  3. One of Tyler’s goals with the podcast is to teach people to ask better questions. He models this in each episode and chooses his questions carefully.
  4. A major theme in Tyler’s questions is: How well do our current models explain the world and where do they fall short? He applies this at all levels from big picture macro trends to micro interactions of songbirds.
  5. Reading Marginal Revolution is helpful for gaining context about Tyler’s interests and how he approaches topics. Reading MR will help you understand CWT and vice versa. Not necessary, but certainly helpful.
  6. What’s up with Overrated vs Underrated segment? I see this as Cowen both wanting to understand the world better and to learn what makes each guest who they are (see 7). Whenever something is not correctly rated, there is a mystery to uncover. And this segment is rapid fire and fun!
  7. What about the [Guest name] Production Function segment? Context matters. In this segment Tyler asks questions to gain context about the guest to help us understand where they come from, what drives them, what paths they took that lead them to where they are now, and how they work.
  8. Transcripts of each show are available at conversationswithtyler.com. Use them! Sometimes the questions are rapid fire and I don’t catch something a guest mentions, so I’ll either pause and rewind or pull up the transcript and take a note. That is one of the benefits of the podcast medium: Pausing and replaying is built-in and expected, and links are available in the notes section of most popular podcast players.
  9. How I like to listen to the show: I listen while I’m doing auto-pilot tasks like laundry or dishes so that I can focus on the conversation. I often pause the episode and jot down a few phrases to research further, books to buy, music to listen to, and movies to watch after I’m done listening.

Two other guides from CWT listeners:


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