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 range across five centuries of Mexican history, from why Mexico held together after independence when every other post-colonial superstate collapsed, to why Yucatán is now one of the safest places on earth, what two leaders from Oaxaca tell us about Mexican politics, how Mexico avoided the military coups that plagued the rest of Latin America, what Cárdenas's land reform actually achieved versus what it promised, whether the ejido system held Mexico back, why Mexico worried too much about land and not enough about human capital, how Mexico's fertility rate fell below America's, why Guerrero has been violent for two centuries, why the new judicial reforms are a disaster, where to find the best food in Mexico and Manhattan, what a cache of illicit Mexican silver sitting on a ship in the English Channel has to do with his next book, and more.
Read a full transcript enhanced with helpful links, or watch the full video on the new dedicated Conversations with Tyler channel.
Recorded February 27th, 2026.
Other ways to connect
Timestamps:
00:00:00 - Intro
00:01:30 - Post-Independence Mexico
00:05:18 - Peace in Yucatán
00:6:54 - Quintana Roo
00:08:24 - Mexican Infrastructure
00:10:26 - Oaxaca
00:13:54 - Great Food Outside Cities
00:16:39 - Leaders from Coahuila
00:17:50 - Military Rule and Civil War in Mexico
00:21:47 - The Cárdenas Regime
00:24:03 - The Ejido System
00:25:49 - Human Capital
00:40:59 - Doing Mexican History as a Brit
00:42:43 - Guerrero
00:48:37 - Michoacán Violence
00:50:44 - Monterrey
00:52:40 - Judicial Reforms
00:54:44 - The Best Mexican Film, Music, and Novel
00:59:42 - The Best Trip Around Mexico
01:04:05 - Outro
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, convinced that the great books are self-sustaining, and that irony is what separates serious philosophy from the rest.
Tyler and Harvey discuss how Machiavelli's concept of fact was brand new, why his longest chapter is a how-to guide for conspiracy, whether America's 20th-century wars refute the conspiratorial worldview, Trump as a Shakespearean vulgarian who is in some ways more democratic than the rest of us, why Bronze Age Pervert should not be taken as a model for Straussianism, the time he tried to introduce Nietzsche to Quine, why Rawls needed more Locke, what it was like to hear Churchill speak at Margate in 1953, whether great books are still being written, how his students have and haven't changed over 61 years of teaching, the eclipse rather than decline of manliness, and what Aristotle got right about old age and much more.
Read a full transcript enhanced with helpful links, or watch the full video on the new dedicated Conversations with Tyler channel.
Recorded January 22nd, 2026.
This episode was made possible through the support of the John Templeton Foundation.
Other ways to connect
Timestamps:
00:00:00 - Bumper
00:00:36 - Intro
00:01:20 - Machiavelli's "Effectual Truth"
00:05:56 - Conspiracy Theories
00:12:39 - The Vulgarity of Democracy
00:16:35 - The Future of Straussianism
00:34:30 - Why the Supply of Great Books has Dried Up
00:37:56 - Rational Control vs. Spontaneous Order
00:40:25 - Winston Churchill
00:43:30 - Students at Harvard
00:46:05 - Manliness
00:47:34 - Death and Politics
00:48:56 - Outro
Image Credit: Erin Clark via Getty Images
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, debate whether Isabella secretly seduces Angelo, argue over whether the Duke's proposal is closer to liberation or enslavement, trace the play's connections to The Merchant of Venice and The Rape of Lucrece, assess the parallels to James I, weigh whether it's a Girardian play (Oliver: emphatically not), and parse exactly what Isabella means when she says "I did yield to him," before turning to the best way to consume Shakespeare, what Jane Austen took from Adam Smith, why Swift may be the most practically intelligent writer in English, how advertising really works and why most of it doesn't, which works in English literature are under- and overrated, what makes someone a late bloomer, whether fiction will deal seriously with religion again, whether Ayn Rand's villains are more relevant now than ever, and much more.
Read a full transcript enhanced with helpful links, or watch the full video on the new dedicated Conversations with Tyler channel.
Recorded January 12th, 2026.
This episode was made possible through the support of the John Templeton Foundation.
Other ways to connect
Timestamps:
00:00:00 - Intro
00:01:40 - What Shakespeare is really saying in Measure for Measure
00:29:17 - The best way to consume Shakespeare
00:32:26 - Jane Austen, Adam Smith, and Jonathan Swift
00:39:29 - Advertising that works
00:44:37 - Things that are under- and overrated in literature
00:51:24 - Late bloomers
00:58:36 - Outro
Image Credit: Sam Alburger
When Tyler called Joe Studwell's How Asia Works "perhaps my favorite economics book of the year" back in 2013, he wasn't alone: it became one of the most influential treatments of industrial policy ever written. Now Studwell has turned his attention to Africa with How Africa Works. Tyler calls it excellent, extremely well-researched, and essential reading, but does Studwell's optimism about the continent hold up under scrutiny?
Tyler and Joe explore whether population density actually solves development, which African countries are likely to achieve stable growth, whether Africa has a manufacturing future, why state infrastructure projects decay while farmer-led irrigation thrives, what progress looks like in education and public health, whether charter cities or special economic zones can work, and how permanent Africa's colonial borders really are. After testing Joe's optimism about Africa, Tyler shifts back to Asia: what Japan and South Korea will do about depopulation, why industrial policy worked in East Asia but failed in India and Brazil, what went wrong in Thailand, and what Joe will tackle next.
Read a full transcript enhanced with helpful links, or watch the full video on the new dedicated Conversations with Tyler channel.
Recorded January 23rd, 2026.
Other ways to connect
Image Credit: Nick J.B. Moore
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 remarkable century ahead. Maybe the real problem was the "Negative Nellies" who panicked afterward rather than the speculators everyone blamed. For that matter, isn't 2008 looking less and less like a bubble with each passing year?
Tyler and Andrew debate whether those 1929 stock prices were justified, what Fed and policy choices might have prevented the Depression, whether Glass-Steagall was built on a flawed premises, what surprised Andrew most about the 1920s beyond the crash itself, how business leaders then would compare to today's CEOs, whether US banks should consolidate, how Andrew would reform US banking regulation, what to make of narrow banking proposals and stablecoins, whether retail investors should get access to private equity and venture capital, why sports gambling and new financial regulations won't make us much safer, how Andrew broke into the New York Times at age 18, how he manages his information diet, what he learned co-creating Billions, what he plans on learning about next, and more.
Read a full transcript enhanced with helpful links, or watch the full video on the new dedicated Conversations with Tyler channel.
Recorded October 30th, 2025.
Other ways to connect
Image Credit: Mike Cohen
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 Christianity and the Reformation, and his latest on sex and the church, which demonstrates what MacCulloch calls the historian's true vocation: unsettling settled facts to keep humanity sane.
Tyler and Diarmaid explore whether monotheism correlates with monogamy, Christianity's early instinct towards egalitarianism, what the Eucharistic revolution reveals about the cathedral building boom, the role of Mary in Christianity and Islam, where Michel Foucault went wrong on sexuality, the significance of the clerical family replacing the celibate monk, why Elizabeth I—not Henry VIII—mattered most for the English Reformation, why English Renaissance music began so brilliantly but then needed to start importing Germans, whether Christianity needs hell to survive, what MacCulloch plans to do next, and more.
Read a full transcript enhanced with helpful links, or watch the full video on the new dedicated Conversations with Tyler channel.
Recorded October 29th, 2025.
This episode was made possible through the support of the John Templeton Foundation.
Other ways to connect
Image Credit: Barry Jones
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 grading verse to economists building evaluation frameworks—and has become one of the fastest-growing startups in history.
Tyler and Brendan discuss why Mercor pays poets $150 an hour, why AI labs need rubrics more than raw text, whether we should enshrine the aesthetic standards of past eras rather than current ones, how quickly models are improving at economically valuable tasks, how long until AI can stump Cass Sunstein, the coming shift toward knowledge workers building RL environments instead of doing repetitive analysis, how to interview without falling for vibes, why nepotism might make a comeback as AI optimizes everyone's cover letters, scaling the Thiel Fellowship 100,000X, what his 8th-grade donut empire taught him about driving out competition, the link between dyslexia and entrepreneurship, dining out and dating in San Francisco, Mercor's next steps, and more.
Read a full transcript enhanced with helpful links, or watch the full video on the new dedicated Conversations with Tyler channel.
Recorded October 16th, 2025.
Other ways to connect
Timestamps
00:00:00 - Hiring poets to teach AI
00:05:29 - Measuring real-world AI progress
00:13:25 - Why rubrics are the new oil
00:18:44 - Enshrining taste in LLMs
00:22:38 - Turning society into one giant RL machine
00:26:37 - When AI will stump experts
00:30:46 - AI and employment
00:35:05 - Why vibes-based hiring fails
00:39:55 - Solving labor market matching problems
00:45:01 - Scaling the Thiel Fellowship
00:48:11 - A hypothetical gap year
00:50:31 - Donuts, debates, and dyslexia
00:56:15 - Dating and dining out
00:59:01 - Mercor's next steps
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 more, including covering the most popular and underrated episodes, why single-subject deep dives made for some of the best conversations this year, the biggest AI surprises and how LLMs changed the show's production function, what happened with the Magnus Carlsen episode, listener questions on everything from hotel selection to AI x-risk discourse, Tyler's serene acknowledgment that uncontrollable laughter is something he has neither experienced nor desires, reviewing his pop culture picks from 2015, and a dispatch from Muscat, Oman.
Read a full transcript enhanced with helpful links, or watch the full video on the new dedicated Conversations with Tyler channel.
Recorded November 5th and December 15th, 2025.
Other ways to connect
Timestamps
00:00:00 - Favorite episodes of the year
00:12:08 - AI's impact on the show
00:15:05 - The lost Magnus episode
00:17:13 - Tyler's #1 hotel amenity
00:18:40 - Tyler's growing influence and thoughts on tariffs
00:21:15 - AI x-risk discourse
00:26:22 – Copying Tyler's interview style
00:28:50 - Tyler's lack of joy
00:32:55 - How well ChatGPT answers as Tyler
00:35:15 - Tyler's 2015 movie picks
00:40:44 - Tyler's 2015 book picks
00:45:00 - Tyler's 2015 music picks
00:48:16 - Most popular episodes and thoughts on Oman
Photo Credit: Kevin Trimmer
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 the world from limited data. Her central insight is that babies learn like scientists, running experiments and updating beliefs based on evidence. But Tyler wonders: are scientists actually good learners? It's a question that leads them into a wide-ranging conversation about what we've been systematically underestimating in young minds, what's wrong with simple nature-versus-nurture frameworks, and whether AI represents genuine intelligence or just a very sophisticated library.
Tyler and Alison cover how children systematically experiment on the world and what study she'd run with $100 million, why babies are more conscious than adults and what consciousness even means, episodic memory and aphantasia, whether Freud got anything right about childhood and what's held up best from Piaget, how we should teach young children versus school-age kids, how AI should change K-12 education and Gopnik's case that it's a cultural technology rather than intelligence, whether the enterprise of twin studies makes sense and why she sees nature versus nurture as the wrong framework entirely, autism and ADHD as diagnostic categories, whether the success of her siblings belies her skepticism about genetic inheritance, her new project on the economics and philosophy of caregiving, and more.
Read a full transcript enhanced with helpful links, or watch the full video on the new dedicated Conversations with Tyler channel.
Recorded October 30th, 2025.
Other ways to connect
Timestamps
00:00:00 - How children—and scientists—learn
00:14:35 - Consciousness, episodic memories, and aphantasia
00:23:06 - Freud's and Piaget's theories about childhood
00:27:49 - Twin studies and nature vs. nurture
00:39:33 - Teaching strategies for younger vs. older children
00:44:07 - AI's ability to generate novel insights
00:53:57 - What Autism and ADHD diagnoses do and don't reveal
00:58:02 - The success of the Gopnik siblings
Photo Credit: Rod Searcey
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 conversation a rare window into how he thinks. He now runs XN, a firm built around concentrated bets on a small number of companies with long holding periods. However, his education in judgment began much earlier, in a two-family house in Flushing that his parents converted into a four-family house. It was there where a young Gaurav served as de facto landlord, collecting rent and negotiating late payments at age 10. That grounding now expresses itself across an unusual range of domains: Tyler invited him on the show not just as an investor, but as someone with a rare ability to judge quality in cities, talent, art, and more with equal fluency.
Tyler and Gaurav discuss how Queens has thrived without new infrastructure, what he'd change as "dictator" of Flushing, whether Robert Moses should rise or fall in status, who's the most underrated NYC mayor, what's needed to attract better mayoral candidates, the weirdest place in NYC, why he initially turned down opportunities in investment banking for consulting, bonding with Rishi Sunak over railroads, XN's investment philosophy, maintaining founder energy in investment firms and how he hires to prevent complacency, AI's impact on investing, the differences between New York and London finance, the most common fundraising mistake art museums make, why he collects only American artists within 20 years of his own age, what makes Kara Walker and Rashid Johnson and Salman Toor special, whether buying art makes you a better investor, his new magazine Totei celebrating craft and craftsmanship, and much more.
Read a full transcript enhanced with helpful links, or watch the full video on the new dedicated Conversations with Tyler channel.
Recorded October 8th, 2025.
Other ways to connect
Timestamps
00:00:00 - Intro
00:01:32 - Queens and NYC's geography
00:08:36 - New York City mayors and electoral politics
00:13:22 - Building a career in investing
00:18:50 - XN's investment philosophy
00:24:35 - Maintaining founder energy in investment firms
00:30:45 - The sociology of finance in NYC, London, and UAE
00:32:21 - How AI is reshaping investing
00:36:53 - Museum operations
00:42:21 - Favorite artists
00:50:39 - Tastes in art and how the canon will evolve
00:57:22 - Totei, a new venture
Help us keep the conversations going in 2026. Donate to Conversations with Tyler today.
Dan Wang argues that China is a nation of engineers while America is a nation of lawyers, and this distinction explains everything from subway construction to pandemic response to why Chinese citizens will never have yards with dogs. His prescription: America should become 20% more engineering-minded to fix its broken infrastructure, while China needs to be 50% more lawyerly so the Communist Party can stop strangling individual rights and the creative impulses of its people. But would a more lawyerly China constrain state power, or just create new tools for oppression? And aren't the American suburbs actually sterling achievements where the infrastructure works quite well?
Tyler and Dan debate whether American infrastructure is actually broken or just differently optimized, why health care spending should reach 35% of GDP, how lawyerly influences shaped East Asian development differently than China, China's lack of a liberal tradition and why it won't democratize like South Korea or Taiwan did, its economic dysfunction despite its manufacturing superstars, Chinese pragmatism and bureaucratic incentives, a 10-day itinerary for Yunnan, James C. Scott's work on Zomia, whether Beijing or Shanghai is the better city, Liu Cixin and why volume one of The Three-Body Problem is the best, why contemporary Chinese music and film have declined under Xi, Chinese marriage markets and what it's like to be elderly in China, the Dan Wang production function, why Stendhal is his favorite novelist and Rossini's Comte Ory moves him, what Dan wants to learn next, whether LLMs will make Tyler's hyper-specific podcast questions obsolete, what flavor of drama their conversation turned out to be, and more.
Read a full transcript enhanced with helpful links, or watch the full video on the new dedicated Conversations with Tyler channel.
Recorded October 31st, 2025.
Other ways to connect
Timestamps 00:00:00 - American infrastructure and suburban life 00:05:18 - American vs. Chinese infrastructure buildouts... 00:12:25 - And health care investment 00:17:52 - Chinese suburbs 00:20:10 - The existing lawyerly influence in East Asia 00:25:12 - China's lack of a liberal tradition 00:29:35 - Why China's won't democratize 00:33:49 - China's economic disfunction 00:38:44 - China's expansionism 00:41:55 - Chinese pragmatism and bureaucratic incentives 00:46:50 - Chinese cities and regional culture 00:59:44 - James C. Scott, Zomia, and elite culture 01:06:27 - A 10-day Yunnan itinerary 01:11:57 - On Chinese arts, literature, and cultural expression 01:18:23 - The Dan Wang production function 01:30:34 - Tyler's grand strategy, or lack thereof