What AI Is Doing to Your Brand - A Conversation with Cat Holt

From AI Ready Podcast with Harrison Painter by Harrison Painter

February 18, 2026 · 1h 1m · Episode 88

About this episode

Cat Holt discusses the impact of AI on branding and the importance of brand strategy in the modern landscape.

AI is already inside your brand whether you planned for it or not. Cat Holt has spent 26 years watching brands get this wrong — and she's here to break down exactly what's happening and what leaders need to do about it. Cat is the strategic architect behind the Dr. Rick for Progressive Insurance campaign and the Founder of Coologee, a brand strategy firm helping companies navigate AI, disruption, and identity. In this conversation, we get into what brand actually means and why it is not the same thing as marketing or advertising. We talk about what happens when a founder's personal brand overtakes the company, why OpenAI's brand seems to operate above the normal rules of reputation, and what Bud Light and Cracker Barrel teach us about the cost of getting brand evolution wrong. Cat walks through the origin of the Dr. Rick campaign — the real insight behind it, why executives were scared to run it, and how it started as a small Facebook test before becoming Progressive's highest-performing campaign a decade later. Then we get into AI directly: how it is being embedded into brand identity whether companies want it or not, the IP and creative ownership conversation nobody is having…

People in this episode

Guest: Cat Holt

Topics covered

AI
branding
marketing
advertising
brand strategy

Keywords

Dr. Rick
Progressive Insurance
Coologee
brand identity
creative ownership

Mentioned in this episode

Products: Bud Light, Cracker Barrel, Progressive Insurance