Tyler and Y Combinator co-founder Paul Graham sat down at his home in the English countryside to discuss what areas of talent judgment his co-founder and wife Jessica Livingston is better at, whether young founders have gotten rarer, whether he still takes a dim view of solo founders, how to 2x ambition in the developed world, on the minute past which a Y Combinator interviewer is unlikely to change their mind, what YC learned after rejecting companies, how he got over his fear of flying, Florentine history, why almost all good artists are underrated, what's gone wrong in art, why new homes and neighborhoods are ugly, why he wants to visit the Dark Ages, why he's optimistic about Britain and San Fransisco, the challenges of regulating AI, whether we're underinvesting in high-cost interruption activities, walking, soundproofing, fame, and more.

Read a full transcript enhanced with helpful links.

Recorded July 15th, 2023.

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Photo credit: Dave Thomas

Tyler sat down at Comedy Cellar with owner Noam Dworman to talk about the ever-changing stand-up comedy scene, including the perfect room temperature for stand-up, whether comedy can still shock us, the effect on YouTube and TikTok, the transformation of jokes into bits, the importance of tight seating, why he doesn’t charge higher prices for his shows, the differences between the LA and NYC scenes, whether good looks are an obstacle to success, the oldest comic act he still finds funny, how comedians have changed since he started running the Comedy Cellar in 2003, and what government regulations drive him crazy. They also talk about how 9/11 got Noam into trouble, his early career in music, the most underrated guitarist, why live music is dead in NYC, and what his plans are for expansion.

Read a full transcript enhanced with helpful links, or watch the full video. 

Recorded March 15th, 2023.

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David Bentley Hart is an American writer, philosopher, religious scholar, critic, and theologian who has authored over 1,000 essays and 19 books, including a very well-known translation of the New Testament and several volumes of fiction.

In this conversation, Tyler and David discuss ways in which Orthodox Christianity is not so millenarian, how theological patience shapes the polities of Orthodox Christian nations, how Heidegger deepened his understanding of Christian Orthodoxy, who played left field for the Baltimore Orioles in 1970, the simplest way to explain how Orthodoxy diverges from Catholicism, the future of the American Orthodox Church, what he thinks of the Book of Mormon, whether theological arguments are ultimately based on reason or faith, what he makes of reincarnation and near-death experiences, gnosticism in movies and TV, why he dislikes Sarah Ruden’s translation of the New Testament, the most difficult word to translate, a tally of the 15+ languages he knows, what he’ll work on next, and more.

Read a full transcript enhanced with helpful links, or watch the full video. 

Recorded March 23rd, 2023.

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In his second appearance, Reid Hoffman joined Tyler to talk everything AI: the optimal liability regime for LLMs, whether there’ll be autonomous money-making bots, which agency should regulate AI, how AI will affect the media ecosystem and the communication of ideas, what percentage of the American population will eschew it, how gaming will evolve, whether AI’s future will be open-source or proprietary, the binding constraint preventing the next big step in AI, which philosopher has risen in importance thanks to AI, what he’d ask a dolphin, what LLMs have taught him about friendship, how higher education will change, and more. They also discuss Sam Altman’s overlooked skill, the biggest cultural problem in America, the most underrated tech scene, and what he’ll do next.

Read a full transcript enhanced with helpful links, or watch the full video.  Reid's podcast Possible is back this summer with a three-part miniseries called “AI and The Personal,” which launched on June 21st. Featured guests use AI, hardware, software and their own creativity to better people's daily lives. Subscribe to get the series.

Recorded May 9th, 2023.

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Photo credit: David Yellen

Noam Chomsky joins Tyler to discuss why Noam and Wilhelm von Humboldt have similar views on language and liberty, good and bad evolutionary approaches to language, what he thinks Stephen Wolfram gets wrong about LLMs, whether he’s optimistic about the future, what he thinks of Thomas Schelling, the legacy of the 1960s-era left libertarians, the development trajectories of Nicaragua and Cuba, why he still answers every email, what he’s been most wrong about, and more.

Read a full transcript enhanced with helpful links, or watch the full video. 

Recorded February 27th, 2023

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Photo credit: Duncan Rawlinson - Duncan.co

Peter Singer is one of the world’s most influential living philosophers, whose ideas have motivated millions of people to change how they eat, how they give, and how they interact with each other and the natural world.

Peter joined Tyler to discuss whether utilitarianism is only tractable at the margin, how Peter thinks about the meat-eater problem, why he might side with aliens over humans, at what margins he would police nature, the utilitarian approach to secularism and abortion, what he’s learned producing the Journal of Controversial Ideas, what he’d change about the current Effective Altruism movement, where Derek Parfit went wrong, to what extent we should respect the wishes of the dead, why professional philosophy is so boring, his advice on how to enjoy our lives, what he’ll be doing after retiring from teaching, and more.

Read a full transcript enhanced with helpful links, or watch the full video. 

Recorded May 25th, 2023

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Photo credit: Katarzyna de Lazari-Radek

On good days, Seth Godin thinks about all the progress we’re making on climate change. On bad days, he thinks about the problem of racing bibs. Though pieces of paper safety-pinned to runners’ chests seem obviously outdated, the bibs persist, highlighting how difficult it can be to change a culture for the better. And yet Seth also persists to improve the culture around marketing and work, giving hundreds of talks, writing daily blog posts, and publishing 21 best-sellers. His latest, The Song of Significance, explains why workplace culture has gotten so bad and what leaders can do to make it better.

Seth joined Tyler to discuss why direct marketing works at all, the marketing success of Trader Joe’s vs Whole Foods, why you can’t reverse engineer Taylor Swift’s success, how Seth would fix baseball, the brilliant marketing in ChatGPT’s design, the most underrated American visual artist, the problem with online education, approaching public talks as a team process, what makes him a good cook, his updated advice for aspiring young authors, how growing up in Buffalo shaped him, what he’ll work on next, and more.

Read a full transcript enhanced with helpful links, or watch the full video. 

Recorded May 23rd, 2023

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Photo credit: Darius Bashar and Archangel

What’s more intense than leading the IMF during a financial crisis? For Simon Johnson, it was co-authoring a book with fellow economist (and past guest) Daron Acemoglu. Written in six months, their book Power and Progress: Our Thousand-Year Struggle Over Technology and Prosperity, argues that widespread prosperity is not the natural consequence of technological progress, but instead only happens when there is a conscious effort to bend the direction and gains from technological advances away from the elite. 

Tyler and Simon discuss the ideas in the book and on Simon’s earlier work on finance and banking, including at what size a US bank is small enough to fail, the future of deposit insurance, when we’ll see a central bank digital currency, his top proposal for reforming the IMF, how quickly the Industrial Revolution led to widespread prosperity, whether AI will boost wages, how he changed his mind on the Middle Ages, the key difference in outlook between him and Daron, how he thinks institutions affect growth, how to fix northern England's economic climate, whether the UK should join NAFTA, improving science policy, the Simon Johnson production function, whether MBAs are overrated, the importance of communication, and more.

Read a full transcript enhanced with helpful links, or watch the full video. 

Recorded March 21st, 2023

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Photo credit: MIT

As the founding executive editor of Wired magazine and the author of several acclaimed books on technology and culture, Kevin Kelly has long been known for his visionary ideas and insights. But his latest work, Excellent Advice for Living takes a different approach, drawing on his own experience and wisdom to offer practical tips and advice for navigating life's challenges.

Naturally then, Kevin and Tyler start this conversation on advice: what kinds of advice Kevin was afraid to give, his worst advice, how to get better at following advice, and whether people who ask for advice really want it in the first place. Then they move on to the best places to see traditional cultures in Asia, the one thing in Kevin’s travel kit he can’t be without, his favorite part of India, why he’s so excited about brain-computer interfaces, how AI will change religion, what the Amish can teach us about tech adoption, the most underrated documentary, his initial entry point into tech, why he’s impressed by the way Jeff Bezos handles power, the last thing he's changed his mind about, how growing up in Westfield, New Jersey affected him, his next project called the Hundred Year Desirable Future, and more.

Read a full transcript enhanced with helpful links, or watch the full video. 

Recorded April 27th, 2023

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Anna Keay is a historian who specializes in the cultural heritage of Great Britain. As the director of the Landmark Trust, she has overseen the restoration of numerous historical buildings and monuments, while also serving as a prolific author and commentator on the country's architectural and artistic traditions. Her book, The Restless Republic: Britain Without a Crown, was one of Tyler’s top picks for 2022.

Tyler sat down with Anna to discuss the most plausible scenario where England could’ve remained a republic in the 17th century, what Robert Boyle learned from Sir William Petty, why some monarchs build palaces and others don’t, how renting from the Landmark Trust compares to Airbnb, how her job changes her views on wealth taxes, why neighborhood architecture has declined, how she’d handle the UK’s housing shortage, why giving back the Koh-i-Noor would cause more problems than it solves, why British houses have so little storage, the hardest part about living in an 800-year-old house, her favorite John Fowles book, why we should do more to preserve the Scottish Enlightenment, and more.

Read a full transcript enhanced with helpful links, or watch the full video. 

Recorded February 23rd, 2023

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