Conversations with Tyler – Détails, épisodes et analyse

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

David Brooks returns to the show with a stark diagnosis of American culture. Having evolved from a Democratic socialist to a neoconservative to what he now calls "the rightward edge of the leftward tendency," Brooks argues that America's core problems aren't economic but sociological—rooted in the destruction of our "secure base" of family, community, and moral order that once gave people existential security.

Tyler and David cover why young people are simultaneously the most rejected and most productive generation, smartphones and sex, the persuasiveness of AI vs novels, the loss of audacity, what made William F. Buckley and Milton Friedman great mentors, why academics should embrace the epistemology of the interview, the evolving status of neoconservatism, what Trump gets right, whether only war or mass movements can revive the American psyche, what will end the fertility crisis, the subject of his book, listener questions, 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 July 22nd, 2025.

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

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Photo Credit: Vladimir Kolesnikov/Michael Priest Photography

Mary Gaitskill's knack for writing about the social and physical world with unapologetic clarity has led to her style being described both as "cold and brutal" and "tender and compassionate." Tyler considers her works The Mare, Veronica, and Lost Cat to be some of the best and most insightful American fiction in recent times. And lately she's taken to writing essays on Substack, where she frankly analyzes "subjects that are vexing everybody," including incels, Depp v. Heard, and political fiction.

She joined Tyler to discuss the reasons some people seem to choose to be unhappy, why she writes about oddballs, the fragility of personality, how she's developed her natural knack for describing the physical world, why we're better off just accepting that people are horrible, her advice for troubled teenagers, why she wouldn't clone a lost cat, the benefits and drawbacks of writing online, what she's learned from writing a Substack, what gets lost in Kubrick's adaptation of Lolita, the not-so-subtle eroticism of Victorian novels, the ground rules for writing about other people, how creative writing programs are harming (some) writers, what she learned about men when working as a stripper, how her views of sexual permissiveness have changed since the '90s, how college students have changed over time, what she learned working at The Strand bookstore, and more.

Read a full transcript enhanced with helpful links.

Recorded September 26th, 2022

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Reza Aslan doesn't mind being called a pantheist. In his own "roundabout spiritual journey" and study of the world's religions, which has led him to write books on Islam, the life of Jesus Christ, God, and most recently an American martyr in Persia, he has come to believe the Sufi notion that religion is just a shell one must break through to truly understand God—and that if God is anything at all, then all is God.

He joined Tyler to discuss Shi'a and Christian notions of martyrdom, the heroism of Howard Baskerville, the differences between Sunni and Shi'a Islam, esoteric vs. exoteric expressions of religion, how mystical movements arise more organically than religion, the conflicts over Imams in the Islamic world, how his upbringing as an Iranian immigrant shaped his view of religion, his roundabout spiritual journey, the synthesis of Spinoza and Sufism, the origins of Wahhabism, the relationship (or lackthereof) between religion and political philosophy, the sad repetition of history in Iran, his favorite Iranian movie, and more.

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

Recorded October 12th, 2022

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A leading expert in foreign policy, Walter Russell Mead believes his lack of a PhD—and interest in actually going places—has helped him avoid academic silos and institutional groupthink that's rendered the field ineffective for decades. Mead's latest book, which explores the American-Israeli relationship, is characteristically wide-ranging and multidisciplinary, resulting in
"less a history of U.S.-Israel policy than a sweeping and masterfully told history of U.S. foreign policy in general", according to a New York Times review.

He joined Tyler to discuss how the decline of American religiosity has influenced US foreign policy, which American presidents best and least understood the Middle East, the shrewd reasons Stalin supported Israel, the Saudi secret to political stability, the fate of Pakistan, the most likely scenario for China moving on Taiwan, the gun pointed at the head of German business, the US's "murderous fetishization of ideology over reality" in Sub-Saharan Africa, the inherent weakness in having a foreign policy establishment dominated by academics, what he learned from attending the Groton School, and much more.

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

Recorded August 31st, 2022

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When looking at the U.S. labor market, Byron Auguste sees too many job seekers screened out based on shallow signals like a bachelor's degree, and too few 'screened in' by directly demonstrating the skills needed for the job at hand. To close those opportunity gaps in the American workforce, Byron co-founded and runs Opportunity@Work, which played a key role in Maryland's decision in early 2022 to drop four-year degree requirements for thousands of state jobs in favor of recruiting from those identified as being Skilled Through Alternate Routes, or STARs.

He joined Tyler to discuss workforce training in the digital economy, re-evaluating college degree requirements in recruitment, why IQ is overrated and conscientiousness is underrated, the major opportunity gap in on-the-job training, what people miss about the German apprenticeship model, the best novel about finding a job, what's gone wrong with American men, why we need signal pluralism for higher education admission, why he's wary of AI for predicting labor outcomes, what happened when Maryland rolled back degree requirements for state jobs, the incentive problems in higher education, and more.

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

Recorded September 6th, 2022

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Vaughn Smith is fluent in eight languages but with a beginner's grasp of at least thirty-six (and counting). His talents are so remarkable that the Washington Post did a feature story on him and neuroscientists at MIT requested he do a brain scan for them. But for Vaughn his language skills aren't about attracting attention or monetary gain. "Language is a key to someone's culture, to someone's world," he explains. Whether it's watching a client's face light up when he speaks to them in their native tongue or showing Indigenous children in rural Mexico that their language is valuable and worth preserving, Vaughn views his gifts as a way of connecting with other people.

He joined Tyler to discuss how he began learning languages, the best languages for expressing humor, why he curses in Slovak, why he considers Finnish more romantic than Portugese, what makes Hungarian so difficult to learn, the best way to teach people new languages, how to combat language loss, why he'd like rural Mexicans to have more pride in their culture and way of life, his time as a roadie for a punk rock van, the most rewarding job he's had, why he wants to visit Finland, how enjoying films from different eras is similar to learning new languages, the future of English, and more.

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

Recorded May 26th, 2022

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How can one identify and predict talent? On a search to answer this question and others like it, Tyler Cowen joined venture capitalist and entrepreneur Daniel Gross to explore the art and science of finding talent in their new book Talent: How to Identify Energizers, Creatives, and Winners Around the World. In a panel discussion hosted by Shruti Rajagopalan, Cowen and Gross discuss the applications of their new book, particularly how lifestyle characteristics can indicate an individual is capable of great creativity and talent.

Daniel and Tyler also discuss undervalued talents and skills, what talents they look for in the start-up and investment world, why there is no good chocolate ice cream to be found in San Francisco, what their exercise preferences indicate about their personalities, how they approach identifying talent in different countries and industries, how immigration impacts entrepreneurialism, the short-comings to Zoom interviews, what a messy desk reveals about a person, and more.

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

Recorded June 29th, 2022

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Photo credit: Drew Bird Photo

As a little girl, Cynthia Haven loved reading classic works of literature. At sixteen, she began her career as a reporter. And years later, those two interests converged as they led her to interview and write books about three writers and thinkers whom she also came to call mentors: René Girard, Czeslaw Milosz, and Joseph Brodsky. 

Cynthia joined Tyler to discuss what she's gleaned from each of the three, including what traits they have in common, why her biography of Girard had to come from outside academia, Milosz's reaction to the Berkley Free Speech Movement, Girard's greatest talent—and flaw—as a thinker, whether Brodsky will fall down the memory hole, why he was so terrible on Ukraine, why Cynthia's early career was much like The Devil Wears Prada, the failings of Twitter, and more.

Read a full transcript enhanced with helpful links.

Recorded May 18th, 2022

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