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