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.

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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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