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.

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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.

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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.

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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.

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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

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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.

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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

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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.

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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

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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.

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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

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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.

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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

Cass Sunstein is one of the most widely cited legal scholars of all time and among the most prolific writers working today. This year alone he has five books out, including Imperfect Oracle on the strengths and limits of AI and On Liberalism: In Defense of Freedom. In his second appearance on the show, he brings his characteristic intellectual range to exploring liberalism's present precariousness and AI's implications for law and speech.

Tyler and Cass discuss whether liberalism is self-undermining or simply vulnerable to illiberal forces, the tensions in how a liberal immigration regime would work, whether new generations of liberal thinkers are emerging, if Derek Parfit counts as a liberal, Mill's liberal wokeism, the allure of Mises' "cranky enthusiasm for freedom," whether the central claim of The Road to Serfdom holds up, how to blend indigenous rights with liberal thought, whether AIs should have First Amendment protections, the argument for establishing a right not to be manipulated, better remedies for low-grade libel, whether we should have trials run by AI, how Bob Dylan embodies liberal freedom, Cass' next book about animal rights, 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 10th, 2025.

This episode was made possible through the support of the John Templeton Foundation.

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Blake Scholl is one of the leading figures working to bring back civilian supersonic flight. As the founder and CEO of Boom Supersonic, he's building a new generation of supersonic aircraft and pushing for the policies needed to make commercial supersonic travel viable again. But he's equally as impressive as someone who thinks systematically about improving dysfunction—whether it's airport design, traffic congestion, or defense procurement—and sees creative solutions to problems everyone else has learned to accept.

Tyler and Blake discuss why airport terminals should be underground, why every road needs a toll, what's wrong with how we board planes, the contrasting cultures of Amazon and Groupon, why Concorde and Apollo were impressive tech demos but terrible products, what Ayn Rand understood about supersonic transport in 1957, what's wrong with aerospace manufacturing, his heuristic when confronting evident stupidity, his technique for mastering new domains, how LLMs are revolutionizing regulatory paperwork, and much more.

Recorded live at the Progress Conference, hosted by the Roots of Progress Institute. Special thanks to Big Think for the video production.

Read a full transcript enhanced with helpful links, or watch the full video on the new dedicated Conversations with Tyler channel.

Recorded October 18th, 2025.

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Photo Credit: Jeremi Rebecca