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.

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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

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Donald S. Lopez Jr. is among the foremost scholars of Buddhism, whose work consistently distinguishes Buddhist reality from Western fantasy. A professor at the University of Michigan and author of numerous essential books on Buddhist thought and practice, he's spent decades studying Sanskrit and Tibetan texts, including a formative year spent living in a Tibetan monastery in India. His latest book, The Buddha: Biography of a Myth, tackles the formidable challenge of understanding what we can actually know about the historical Buddha.

Tyler and Donald discuss the Buddha's 32 bodily marks, whether he died of dysentery, what sets the limits of the Buddha's omniscience, the theological puzzle of sacred power in an atheistic religion, Buddhism's elaborate system of hells and hungry ghosts, how 19th-century European atheists invented the "peaceful" Buddhism we know today, whether the axial age theory holds up, what happened to the Buddha's son Rahula, Buddhism's global decline, the evidently effective succession process for Dalai Lamas, how a guy from New Jersey created the Tibetan Book of the Dead, what makes Zen Buddhism theologically unique, why Thailand is the wealthiest Buddhist country, where to go on a three-week Buddhist pilgrimage, how Donald became a scholar of Buddhism after abandoning his plans to study Shakespeare, his dream of translating Buddhist stories into new dramatic forms, 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 6th, 2025.

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