People vs Algorithms · Oct 10, 2025 · 53:17
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This week, we talk about Anthropic’s humanist branding, the fading idea of cool in a fractured culture, and why Gen Z’s nostalgia for the analog world might be the real rebellion. Plus: Anonymous Banker joins to break down why the math behind Paramount buying The Free Press for $150 million includes “free severance” as it will push out many CBS News workers.
* Troy Young’s People vs Algorithms newsletter
* Brian Morrissey’s The Rebooting newsletter
* Alex Schleifer’s Human Computer
* Follow Alex, Brian and Troy on Twitter
Chapters:
* 00:00 Open
* 00:29 Welcome
* 00:58 Listener Feedback
* 07:32 Milan Aesthetics
* 11:46 Taste vs Slop
* 21:51 Gen Z Nostalgia
* 27:28 Claude’s “Brand Residency”
* 29:23 Can AI be cool?
* 36:45 The Free Press Deal
* 48:21 Good Product
* 52:25 Outro
Episodes: People vs Algorithms