Why Nobody Cares About Newsletters Anymore

Why Nobody Cares About Newsletters Anymore

July 15, 2026 · 1h 5m

About this episode

Matt and Kolby discuss historic media disruptions and the current state of newsletters and AI.

In today's episode Matt and Kolby break down historic media disruptions—from cable TV's ESPN and CNN to Joe Rogan's $250M Spotify deal—pulling out what's working, what's being left on the table, and who actually has a real thesis on AI today, from The Rundown's $10M+ newsletter to HubSpot's media buying spree. Timestamps: 00:00 Intro: AI Anxiety and Plateauing Founders03:59 The Framework: How Founders Should Respond to AI05:14 Is This an AI Bubble? Cable TV's ESPN and CNN Bet08:35 Web 1.0: ...

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