Tyler considers Winnie and Nelson: Portrait of a Marriage one of the best books of the last decade, and its author Jonny Steinberg one of the most underrated writers and thinkers—in North America, at least. Steinberg's particular genius lies in getting uncomfortably close to difficult truths through immersive research—spending 350 hours in police ride-alongs, years studying prison gangs and their century-old oral histories, following a Somali refugee's journey across East Africa—and then rendering what he finds with a novelist's emotional insight. 

Tyler and Jonny discuss why South African police only feel comfortable responding to domestic violence calls, how to fix policing, the ghettoization of crime, how prison gangs regulate behavior through century-old rituals, how apartheid led to mass incarceration and how it manifested in prisons,  why Nelson Mandela never really knew his wife Winnie and the many masks they each wore, what went wrong with the ANC, why the judiciary maintained its independence but not its quality, whether Tyler should buy land in Durban, the art scene in Johannesburg, how COVID gave statism a new lease on life, why the best South African novels may still be ahead, his forthcoming biography of Cecil Rhodes, why English families weren't foolish to move to Rhodesia in the 1920s, where to take an ideal two-week trip around South Africa, and more.

Read a full transcript enhanced with helpful links, or watch the full video on the new dedicated Conversations with Tyler channel.

Recorded September 29th, 2025.

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Timestamps:

• 00:00:40 – Policing and crime in South Africa
• 00:11:15 – Prison culture 
• 00:22:04 – Nelson and Winnie Mandela's marriage
• 00:24:47 – Was Winnie Mandela just a bad person?
• 00:29:20 – Nelson Mandela's masks
• 00:32:04 – Mandela's legacy and the ANC
• 00:36:51 – Reasons for optimism in South Africa
• 00:50:58 – His forthcoming biography of Cecil Rhodes
• 00:55:15 – Where to visit in South Africa

George Selgin has spent over four decades thinking about money, banking, and economic history, and Tyler has known him for nearly all of it. Selgin's new book False Dawn: The New Deal and the Promise of Recovery, 1933–1947 examines what the New Deal actually accomplished—and failed to accomplish—in confronting the Great Depression. 

Tyler and George discuss the surprising lack of fiscal and monetary stimulus in the New Deal, whether revaluing gold was really the best path to economic reflation, how much Glass-Steagall and other individual parts of the New Deal mattered, Keynes' "very sound" advice to Roosevelt, why Hayek's analysis fell short, whether America would've done better with a more concentrated banking sector, how well the quantity theory of money holds up, his vision for a "night watchman" Fed, how many countries should dollarize, whether stablecoins should be allowed to pay interest, his stake in a fractional-reserve Andalusian donkey ownership scheme, why his Spanish vocabulary is particularly strong on plumbing, his ambivalence about the eurozone, what really got America out of the Great Depression, and more.

Read a full transcript enhanced with helpful links, or watch the full video on the new dedicated Conversations with Tyler channel.

Recorded September 26th, 2025.

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Photo Credit: Richie Downs

John Amaechi is a former NBA forward/center who became a chartered scientist, professor of leadership at Exeter Business School, and New York Times bestselling author. His newest book, It's Not Magic: The Ordinary Skills of Exceptional Leaders, argues that leadership isn't bestowed or innate, it's earned through deliberate skill development.

Tyler and John discuss whether business culture is defined by the worst behavior tolerated, what rituals leadership requires, the quality of leadership in college basketball and consulting, why Doc Rivers started some practices at midnight, his childhood identification with the Hunchback of Notre Dame and retreat into science fiction, whether Yoda was actually a terrible leader, why he turned down $17 million from the Lakers, how mental blocks destroyed his shooting and how he overcame them, what he learned from Jerry Sloan's cruelty versus Karl Malone's commitment, what percentage of NBA players truly love the game, the experience of being gay in the NBA and why so few male athletes come out, when London peaked, why he loved Scottsdale but had to leave, the physical toll of professional play, the career prospects for 2nd tier players, what distinguishes him from other psychologists, why personality testing is "absolute bollocks," what he 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 September 15th, 2025.

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Steven Pinker returns to Conversations with Tyler with an argument that common knowledge—those infinite loops of "I know that you know that I know"—is the hidden infrastructure that enables human coordination, from accepting paper money to toppling dictators. But Tyler wonders: if most real-world coordination works fine without recursively looping (a glance at a traffic circle), if these models break down with the slightest change in assumptions, and if anonymous internet posters are making correct but uncomfortable truths common knowledge when society might function better with noble lies, is Pinker's theory really capturing how coordination works—and might we actually need less common knowledge, not more?

Tyler and Steven probe these dimensions of common knowledge—Schelling points, differential knowledge, benign hypocrisies like  a whisky bottle in a paper bag—before testing whether rational people can actually agree (spoiler: they can't converge on Hitchcock rankings despite Aumann's theorem), whether liberal enlightenment will reignite and why, what stirring liberal thinkers exist under the age 55, why only a quarter of Harvard students deserve A's, how large language models implicitly use linguistic insights while ignoring linguistic theory, his favorite track on Rubber Soul, what he'll 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 September 12th, 2025.

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

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David Commins, author of the new book Saudi Arabia: A Modern History, brings decades of scholarship and firsthand experience to explain the kingdom's unlikely rise. Tyler and David discuss why Wahhabism was essential for Saudi state-building, the treatment of Shiites in the Eastern Province and whether discrimination has truly ended, why the Saudi state emerged from its poorer and least cosmopolitan regions, the lasting significance of the 1979 Grand Mosque seizure by millenarian extremists, what's kept Gulf states stable, the differing motivations behind Saudi sports investments, the disappointing performance of King Abdullah University of Science and Technology despite its $10 billion endowment, the main barrier to improving its k-12 education, how Yemen became the region's outlier of instability and whether Saudi Arabia learned from its mistakes there, the Houthis' unclear strategic goals, the prospects for the kingdom's post-oil future, the topic of David's next book, and more.

Read a full transcript enhanced with helpful links, or watch the full video on the new dedicated Conversations with Tyler channel.

Recorded August 22nd, 2025.

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

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Seamus Murphy is an Irish photographer and filmmaker who has spent decades documenting life in some of the world's most challenging places—from Taliban-controlled Afghanistan to Nigeria's Boko Haram territories. Having left recession-era Ireland in the 1980s to teach himself photography in American darkrooms, Murphy has become that rare artist who moves seamlessly between conflict zones and recording studios, creating books of Afghan women's poetry while directing music videos that anticipated Brexit.

Tyler and Seamus discuss the optimistic case for Afghanistan, his biggest fear when visiting any conflict zone, how photography has shaped perceptions of Afghanistan, why Russia reminded him of pre-Celtic Tiger Ireland, how the Catholic Church's influence collapsed so suddenly in Ireland, why he left Ireland in the 1980s, what shapes Americans impression of Ireland, living part-time in Kolkata and what the future holds for that "slightly dying" but culturally vibrant city, his near-death encounters with Boko Haram in Nigeria, the visual similarities between Michigan and Russia, working with PJ Harvey on Let England Shake and their travels to Kosovo and Afghanistan together, his upcoming film about an Afghan family he's documented for thirty years, and more.

Read a full transcript enhanced with helpful links, or watch the full video on the new dedicated Conversations with Tyler channel.

Recorded August 21st, 2025.

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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

In his third appearance on Conversations with Tyler, Nate Silver looks back at past predictions, weighs how academic ideas such as expected utility theory fare in practice, and examines the world of sports through the lens of risk and prediction.

Tyler and Nate dive into expected utility theory and random Nash equilibria in poker, whether Silver's tell-reading abilities transfer to real-world situations like NBA games, why academic writing has disappointed him, his move from atheism to agnosticism, the meta-rationality of risk-taking, electoral systems and their flaws, 2028 presidential candidates,  why he thinks superforecasters will continue to outperform AI for the next decade, why more athletes haven't come out as gay, redesigning the NBA, what mentors he needs now, the cultural and psychological peculiarities of Bay area intellectual communities, why Canada can't win a Stanley Cup, the politics of immigration in Europe and America, what he'll work on 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 July 23rd, 2025.

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Annie Jacobsen has a favorite word for America's nuclear doctrine: madness. It's madness that any single person has six minutes to decide the fate of civilization, madness that we've built weapons capable of ending the world in 72 minutes, and madness that everything hangs by the thread of deterrence. But to Tyler, life is "a lot of different kinds of madness," and the real question is simply getting the least harmful form available to us. It's a conversation sparked by her latest book Nuclear War: A Scenario, which Tyler calls one of his favorites from last year—and which is compelling enough that Denis Villeneuve is turning it into a screenplay.

Tyler and Annie explore whether we should be more afraid of nuclear weapons or if fear itself raises the risks, who should advise presidents during the six-minute decision window, whether moving toward disarmament makes us safer or more vulnerable, what Thomas Schelling really meant about nuclear war and rational actors, the probability that America would retaliate after a nuclear attack, the chances of intercepting a single incoming ICBM, why missile defense systems can't replicate Israel's Iron Dome success, how Pakistan-India nuclear tensions could escalate, why she's surprised domestic drone attacks haven't happened yet, her reporting on JFK assassination mysteries and deathbed phone calls, her views on UFOs and the dark human experiments at Area 51, what motivates intelligence community operators, her encounters with Uri Geller and CIA psychic research, what she's working on 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 May 19th, 2025.

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Helen Castor is a British historian and BBC broadcaster who left Cambridge because she wanted to write narrative history focused on individuals rather than the analytical style typical of academia. As someone interested in individual psychology and the functioning of power, Castor finds medieval England offers the perfect setting because its sophisticated power structures exist in "bare bones" without the "great apparatus of state," bringing individual power plays into sharper relief. Her latest book, The Eagle and the Hart, exemplifies this approach by examining Richard II and Henry IV as individuals whose personal choices became constitutional precedents that echo through English history.

Tyler and Helen explore what English government could and couldn't do in the 14th century, why landed nobles obeyed the king, why parliament chose to fund wars with France, whether England could have won the Hundred Years' War, the constitutional precedents set by Henry IV's deposition of Richard II, how Shakespeare's Richard II scandalized Elizabethan audiences, Richard's superb artistic taste versus Henry's lack, why Chaucer suddenly becomes possible in this period, whether Richard II's fatal trip to Ireland was like Captain Kirk beaming down to a hostile planet, how historians continue to discover new evidence about the period, how Shakespeare's Henriad influences our historical understanding, Castor's most successful work habits, what she finds fascinating about Asimov's I, Robot, the subject of her next book, and more.

Read a full transcript enhanced with helpful links, or watch the full video on the new dedicated Conversations with Tyler channel.

Recorded April 2nd, 2025.

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Photo Credit: Stuart Simpson