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We start with a goofy TV-spotting trivia question and end up mapping the ways ads and AI both learn how to push our buttons. Along the way, we compare the AI tools we actually use, the ones we might pay for, and a negotiation trick that makes people talk more than you do.
• spotting Flo from Progressive and Mel from Flight of the Conchords on Mad Men
• why insurance commercials feel like shared universes
• breaking down Progressive characters like Dr. Rick and the “passive progressive” bit
• choosing a paid AI assistant for everyday life: Claude vs ChatGPT vs Gemini vs Copilot
• how bundles like Google One change the cost equation
• AI video avatars and the weird line between fun and creepy
• creativity vs logic and why AI flattery feels manipulative
• Chris Voss mirroring technique and why repeating words works
• the worry about news bubbles, no shared truth, and an Orwell-style slide
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