Most people who leave Wall Street after twenty years either retire or find another way to make a lot of money. Chris Arnade chose to walk through cities most travelers never truly see. What emerged from this approach is a unique form of street-level sociology that has attracted a devoted following on Substack. Arnade's work suggests that our most sophisticated methods of understanding the world might be missing something essential that can only be discovered by moving slowly through space and letting strangers tell you, their stories.

Tyler and Chris discuss how Beijing and Shanghai reveal different forms of authoritarian control through urban design, why Seoul's functional dysfunction makes it more appealing than Tokyo's efficiency, favorite McDonald’s locations around the world, the dimensions for properly assessing a city’s walkability, what Chris packs for long urban jaunts, why he’s not interested in walking the countryside, what travel has taught him about people and culture, what makes the Faroe Islands and El Paso so special, where he has no desire to go, the good and bad of working on Wall Street, the role of pigeons and snapping turtles in his life, finding his 1,000 true fans on Substack, whether museums are interesting, what set him on this current journey, and more.

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

Recorded February 27th, 2025.

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Photo Credit: Bryan Jones

Any Austin has carved a unique niche for himself on YouTube: analyzing seemingly mundane or otherwise overlooked details in video games with the seriousness of an art critic examining Renaissance sculptures. With millions of viewers hanging on his every word about fluvial flows in Breath of the Wild or unemployment rates in the towns of Skyrim, Austin has become what Tyler calls "the very best in the world at the hermeneutics of infrastructure within video games." But Austin's deeper mission is teaching us to think analytically about everything we encounter, and to replace gaming culture's obsession with technical specs and comparative analysis with a deeper aesthetic appreciation that asks simply: what are we looking at, and what does it reveal?

Tyler and Austin explore the value of the YouTube algorithm, what he notices now about real-world infrastructure, whether he perceives glitches IRL, why AI-generated art is getting less interesting, how the value of historical context differs between artistic forms, an aesthetic abundance agenda for nuclear power, the trajectory of video game quality since the 80s, whether the pace of seminal game releases has slowed, the relative value of commentary to the games themselves, why virtual reality adds nothing meaningful to the gaming experience, what’s wrong with most video game analysis, what to eat in New Orleans, Tyler’s gaming history, and more.

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

Recorded March 7th, 2025.

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John Arnold built his fortune in energy trading by surrounding himself with smart people, maintaining emotional detachment, sensing market imbalances through first-principles analysis, and focusing with laser intensity on a single niche until he dominated it completely. Now he's applying that same analytical rigor to philanthropy, where he's discovered that changing human behavior for the long term proves far more challenging than predicting natural gas prices, and that the academic research meant to guide social policy is often riddled with perverse incentives and poor methodology.

Tyler and John discuss his shift from trading to philanthropy and more, including the specific traits that separate great traders from good ones, the tradeoffs of following an "inch wide, mile deep" trading philosophy, why he attended Vanderbilt, the talent culture at Enron, the growth in solar, the problem with Mexico’s energy system, where Canada’s energy exports will go, the hurdles to next-gen nuclear, how to fix America’s tripartite energy grid, how we’ll power new data centers, what’s best about living in Houston, his approach to collecting art, why trading’s easier than philanthropy, how he’d fix tax the US tax code and primary system, and what Arnold Ventures is focusing on next.

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Recorded April 28th, 2025.

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Get tickets to the CWT live show at 92NY with David Brooks!

Theodore Schwartz stands at the pinnacle of neurosurgical expertise. With over 500 published articles, 200 pieces of commentary, and 5 patents to his name—effectively producing a scholarly work every two weeks for three decades—Schwartz spent most of his career at Weill Cornell Medicine, where he pioneered new minimally-invasive surgical techniques and led the Epilepsy Research Laboratory, among many (many) other things. His recent book Gray Matters: A Biography of Brain Surgery offers readers an insider's view of one of medicine's most demanding specialties.

Tyler and Ted discuss how the training for a neurosurgeon could be shortened, the institutional factors preventing AI from helping more in neurosurgery, how to pick a good neurosurgeon, the physical and mental demands of the job, why so few women are currently in the field, whether the brain presents the ultimate bottleneck to radical life extension, why he thinks free will is an illusion, the success of deep brain stimulation as a treatment for neurological conditions, the promise of brain-computer interfaces, what studying epilepsy taught him about human behavior, the biggest bottleneck limiting progress in brain surgery, why he thinks Lee Harvey Oswald acted alone, the Ted Schwartz production function, the new company he’s starting, and much more.

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Recorded January 31st, 2025.

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Few understand both the promise and limitations of artificial general intelligence better than Jack Clark, co-founder of Anthropic. With a background in journalism and the humanities that sets him apart in Silicon Valley, Clark offers a refreshingly sober assessment of AI's economic impact—predicting growth of 3-5% rather than the 20-30% touted by techno-optimists—based on his firsthand experience of repeatedly underestimating AI progress while still recognizing the physical world's resistance to digital transformation.

In this conversation, Jack and Tyler explore which parts of the economy AGI will affect last, where AI will encounter the strongest legal obstacles, the prospect of AI teddy bears, what AI means for the economics of journalism, how competitive the LLM sector will become, why he’s relatively bearish on AI-fueled economic growth, how AI will change American cities, what we'll do with abundant compute, how the law should handle autonomous AI agents, whether we’re entering the age of manager nerds, AI consciousness, when we'll be able to speak directly to dolphins, AI and national sovereignty, how the UK and Singapore might position themselves as AI hubs, what Clark hopes to learn next, and much more.

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Recorded March 28th, 2025.

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Harvard economist Kenneth Rogoff approaches global finance with the same strategic foresight that made him a chess grandmaster. Author of the new book Our Dollar, Your Problem, Rogoff doesn't sugarcoat America's future: he foresees a significant inflation shock within a decade, far more severe than the post-COVID bout. When this second wave hits, he warns, "credibility's really going to be shot."

In this conversation, Ken and Tyler tackle international economic dynamics, unresolved macro puzzles, the state of chess, and more, including whether trade deficits are truly unsustainable, why China's investment-heavy growth model has reached its limits, how currency depreciation neutralizes tariff effects, Pakistan’s IMF bailouts, whether more Latin American countries should dollarize, Japan's deceptively peaceful economic decline, Europe's coming fiscal reckoning, how the US will eventually confront its ballooning debt, the puzzling absence of a recession during our recent disinflation, the potential of phasing out large denomination currency notes, the future relevance of stablecoins, whether America should start a CBDC, Argentina's chances under Milei, who will be the next dominant player in chess, hanging out with Bobby Fischer, drawing out against Magnus Carlsen, and how to save classical chess from excessive computer preparation.

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Recorded April 2nd, 2025.

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Chris Dixon believes we're at a pivotal inflection point in the internet's evolution. As a general partner at Andreessen Horowitz and author of Read Write Own, Chris believes the current internet, dominated by large platforms like YouTube and Spotify, has strayed far from its decentralized roots. He argues that the next era—powered by blockchain technology—can restore autonomy to creators, lower barriers for innovation, and shift economic power back to the network's edges.

Tyler and Chris discuss the economics of platform dominance, how blockchains merge protocol-based social benefits with corporate-style competitive advantages, the rise of stablecoins as a viable blockchain-based application, whether Bitcoin or AI-created currencies will dominate machine-to-machine payments, why Stack Overflow could be the first of many casualties in an AI-driven web, venture capital’s vulnerability to AI disruption, whether open-source AI could preserve national sovereignty, NFTs as digital property rights system for AIs, how Kant’s synthetic a priori, Kripke’s modal logic, and Heidegger’s Dasein sneak into Dixon’s term‑sheet thinking, and much more.

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Recorded March 26th, 2025.

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It’s Beatles day! In this deep dive into one of music's most legendary partnerships, Ian Leslie and Tyler unpack the complex relationship between John Lennon and Paul McCartney. Leslie, whose book John & Paul: A Love Story in Songs examines this creative pairing, reveals how their contrasting personalities—John's intuitive, sometimes chaotic approach and Paul's methodical perfectionism—created a unique creative alchemy that neither could fully replicate after the Beatles split.

They explore John's immediate songwriting brilliance versus Paul's gradual development, debate when the Beatles truly became the Beatles, dissect their best and worst covers, examine the nuances of their collaborative composition process, consider their many musical influences, challenge the sentiment in "Yesterday," evaluate unreleased tracks and post-Beatles reunions, contemplate what went wrong between John and Paul in 1969, assess their solo careers and collaborations with others, compare underrated McCartney and Lennon albums, and ultimately extract broader lessons about creative partnerships.

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Recorded March 4th, 2025.

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Photo Credits: Chris Floyd