Conversations with Tyler

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