Henry Oliver on Measure for Measure, Late Bloomers, and the Smartest Writers in English
Sign up for the Chicago CWT Listener Meetup. Henry Oliver is the preeminent literary critic for non-literary nerds. His Substack, The Common Reader, has thousands of subscribers drawn in by Henry's co...
4 Mar 59min
Andrew Ross Sorkin on Market Bubbles, Banking Rules, and the Real Lessons of 1929
Andrew Ross Sorkin sees the crash of 1929 as a tale of excessive leverage and irrational speculation, but Tyler wonders: maybe those sky-high 1929 prices were actually justified given America's remark...
4 Feb 56min
Diarmaid MacCulloch on Christianity, Sex, and Unsettling Settled Facts
Tyler considers Diarmaid MacCulloch one of those rare historians whose entire body of work rewards reading. This work includes his award-winning Cranmer biography, his sweeping histories of Christiani...
21 Jan 59min
Brendan Foody on Teaching AI and the Future of Knowledge Work
At 22, Brendan Foody is both the youngest Conversations with Tyler guest ever and the youngest unicorn founder on record. His company Mercor hires the experts who train frontier AI models—from poets g...
7 Jan 1h 1min
Conversations with Tyler 2025 Retrospective
Help us keep the conversations going in 2026. Donate to Conversations with Tyler today. On this special year-in-review episode, Tyler and producer Jeff Holmes look back on the past year on CWT and mo...
23 Des 202559min
Alison Gopnik on Childhood Learning, AI as a Cultural Technology, and Rethinking Nature vs. Nurture
Help us keep the conversations going in 2026. Donate to Conversations with Tyler today. Alison Gopnik is both a psychologist and philosopher at Berkeley, studying how children construct theories of t...
17 Des 20251h 1min
Gaurav Kapadia on New York City, Investing, and Contemporary Art
Help us keep the conversations going in 2026. Donate to Conversations with Tyler today. Gaurav Kapadia has deliberately avoided publicity throughout his career in investing, which makes this conversa...
10 Des 202559min
