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.

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

Recorded April 28th, 2025.

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