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It’s Cool to Be Human

AI companies are trying to be cool.

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.

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

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