Urbanist, architect, and professor Vishaan Chakrabarti joins us to explain how the f*** cities got so expensive — and, while we’re at it, ugly. Vishaan is both a doer and a thinker — he’s the founder and creative director of Practice for Architecture and Urbanism as well as a writer of books, talker of TEDs, and a collaborator of journalists (see: "Not Your Car"). In this conversation, we dig into the affordability crisis, why Progressives keep running cities into the ground, and what we need to do to have better cities — and lives.

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On the agenda:

-Prelude [0:00-7:05]

-The Uncertainty Newsletter! [7:06-8:29]

-A History of Housing: The Arms Race and Race [8:30-22:27]

-Bubblegum, shoestring, and vicious circles [22:28-27:31]

-The many ramifications of Reagan [27:32-34:28]

-When cities became safe and sexy [34:29-43:48]

-Progressive cities' misguided policies [43:49-47:49]

-The absurdity and cruelty of San Francisco (see: Nellie Bowles’ “How SF Became a Failed City”) [47:50-52:53]

-The aftermath of Jane Jacobs [52:54-1:00:40]

-Community engagement conundrums [1:00:41-1:11:48]

-On gentrification, cars, and future urbanites [1:11:49-1:20:37]

-The national vs. the urbanist conversation [1:20:38-1:26:14]

-NYC vs. SF [1:26:15-1:36:01]

-Why are cities so depressing? [1:36:02-1:44:34]

-Blindspots [1:44:35-1:47:22]

Uncertain Things is hosted and produced by Adaam James Levin-Areddy and Vanessa M. Quirk. For more doomsday rumination, subscribe to: uncertain.substack.com.