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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• Learn more about Conversations with Tyler and other Mercatus Center podcasts here.

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