Craig Newmark on Institutional Maintenance, Giving Away Control, and the Internet We Were Promised (Live at 92NY)

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1. 

   E281 · 24 Jun 2026 · 50 min

   Joanne Paul on Thomas More and the Tudor World

   Joanne Paul is a historian at the University of Sussex, author, and a go-to Tudor expert on YouTube. She tells Tyler she's drawn to the 16th century because it sits between the medieval and the modern, and because its paths not taken are a way of asking whether our own world had to turn out this way. Her biography Thomas More: A Life takes its subject in that spirit, refusing to reduce More to either martyr or monster. Tyler and Joanne discuss how More influenced Erasmus, what to make of Utopia , why fear drove More's persecution of heretics, how Holbein's portraits of More and Cromwell…

2. 

   E280 · 17 Jun 2026 · 53 min

   Dave Baszucki on Roblox, Teen Entrepreneurs, and the Future of Play

   Dave Baszucki is co-founder and CEO of Roblox, the user-generated gaming platform where all the games are built by the community itself. With over 100 million daily active users and projected revenue bookings of $7 billion this year, it is one of the largest gaming economies in the world—and one that has made millionaires out of teenage developers in Argentina, South Korea, and everywhere in between. Tyler and Dave explore why Roblox decided early against prioritizing advertising revenue, why Dave thinks the main competition of Roblox is its own execution speed rather than Fortnite, whether…

3. 

   E279 · 10 Jun 2026 · 1 hr 1 min

   Katja Hoyer on Weimar, the GDR, and the German Character

   Katja Hoyer is a German-British historian who has made a career out of explaining Germany to the world—and, just as importantly, to Germans themselves. Born in East Germany in 1985 and now based in Britain, she has written acclaimed histories of the German Empire, the GDR, and most recently the Weimar Republic. Tyler and Katja discuss why communism made East Germans more loyal to the system while it bred dissidents in Poland and Hungary, how happy or unhappy life in the GDR actually was, Tyler's own bleak day-trip to East Berlin in 1984, the underrated literature of the GDR (Christa Wolf,…

4. 

   E278 · 27 May 2026 · 46 min

   Toby Wilkinson on Ptolemaic Egypt and the First Great Commercial Civilization

   Toby Wilkinson is one of the world's leading Egyptologists, whose books have ranged across the full sweep of pharaonic history. His latest, The Last Dynasty: Ancient Egypt from Alexander the Great to Cleopatra , covers the 300-year Ptolemaic period — stranger and more modern-feeling than the Egypt of the pyramids, built around commerce and cosmopolitanism rather than divine kingship, and home to the greatest concentration of scientific talent the ancient world ever saw. Tyler and Toby cover how Alexander took over the empire almost without a fight, why Alexandria became the Manhattan of the…

5. 

   E277 · 13 May 2026 · 56 min

   Bob Spitz on the Rolling Stones, Bruce Springsteen, and the Art of Biography

   Bob Spitz has written major biographies of the Beatles, Led Zeppelin, Bob Dylan, and now the Rolling Stones — but also, somehow, Ronald Reagan and Julia Child. In rock, his credentials were hard won: he started out hustling gigs for an unknown Bruce Springsteen for six years, moved on to handling Elton John's American business, and spent long enough in the world to find himself jamming with Paul McCartney and chatting with Bob Dylan on a stoop in the Village. The Reagan and Julia Child books are harder to explain, and perhaps that's the point—Spitz seems to do his best work when he has no…

6. 

   E275 · 15 Apr 2026 · 1 hr 1 min

   Kim Bowes on the Economic Lives of Rome's Ninety Percent

   Kim Bowes is an archaeologist at the University of Pennsylvania whose book, Surviving Rome: The Economic Lives of the Ninety Percent , Tyler calls perhaps his favorite economics book of 2025. By sifting through the material remains of Roman life — shoes, bricks, ceramics, and the like — she uncovers a picture of ordinary Romans who could evidently afford to buy multiple sets of colorful clothes, use gold coins for daily transactions, and eat peppercorns sourced from thousands of miles away. This vast web of commerce, she argues, both bound the empire together and provided the tax base that…

7. 

   E274 · 1 Apr 2026 · 1 hr

   Arthur Brooks on Reinvention, Religion, and the Science of Happiness

   Click here to find Tyler's new generative book, The Marginal Revolution: Rise and Decline, and the Pending AI Revolution ! Arthur Brooks reckons he's on the fourth leg of a spiral-shaped career: French horn player, economist, president of the American Enterprise Institute, and now Harvard professor and evangelist for the science of happiness. His new book, The Meaning of Your Life: Finding Purpose in an Age of Emptiness , argues that happiness isn't a feeling but a combination of enjoyment, satisfaction, and meaning — the macronutrients of happiness, he calls them — and that most of us are…

8. 

   E273 · 25 Mar 2026 · 1 hr 5 min

   Paul Gillingham on Why Mexico Stays Together

   Buy tickets for the live Conversations with Tyler recording with Craig Newmark at 92NY! Tyler calls Paul Gillingham's new book, Mexico: A 500-Year History , the single best introduction to the country's past—and one of the best nonfiction books of 2026. Paul brings both an outsider's eye and ground-level knowledge to Mexican history, having grown up in Cork — a place he'd argue gave him an instinctive feel for fierce local autonomy and land hunger —earning his doctorate on the Mexican Revolution under Alan Knight at Oxford, and doing his fieldwork in the pueblos of Guerrero. He and Tyler…

9. 

   E272 · 18 Mar 2026 · 49 min

   Harvey Mansfield on Machiavelli, Straussianism, and the Character of Liberal Democracy

   Buy tickets for the live Conversations with Tyler recording with Craig Newmark at 92NY! Few living scholars can claim to have shaped how we read Machiavelli as decisively as Harvey Mansfield. His new book, The Rise and Fall of Rational Control , argues that Machiavelli didn't just write about politics—he invented the intellectual machinery of the modern world, starting with the concept of "effectual truth," which Mansfield credits as the seed of modern empiricism. At 93, after 61 years of teaching at Harvard, Mansfield remains cheerfully unimpressed by most of contemporary philosophy,…

10. 

    E271 · 4 Mar 2026 · 59 min

    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 conviction that great literature is where ideas "walk and talk amongst the mess of the real world" in a way no other discipline can match. Tyler, who has called Henry's book Second Act "one of the very best books written on talent," sat down with him to compare readings of Measure for Measure and range across English literature more broadly. Tyler and Henry trade rival readings of the play,…