Advertising's Risk Inside Conversational AI

This week on This Old Marketing, Joe and Robert unpack a trio of headlines that perfectly capture the optimism and overconfidence of the AI era.

First, Apple and Google announce a multi-year partnership on AI. Two of the most powerful companies on the planet, joining forces to shape the future of intelligence. What could possibly go wrong?

Then OpenAI confirms that advertising is coming to ChatGPT later this year. The honeymoon phase of AI is officially over, and the business model phase has arrived. Joe and Robert explore what ads inside conversational interfaces really mean for brands, creators, and trust.

Finally, Salesforce steps up to answer MrBeast's call for the "most amazing Super Bowl ad ever" for Super Bowl 2026. When enterprise software meets YouTube spectacle, expectations get set very high. And history suggests that rarely ends quietly.

Marketing Winners:

• Dos Equis, for proving that great brand storytelling and humor still cut through, even in an AI-flooded content world.

• Breeze Airways, for smart positioning and customer-centric marketing in an industry that desperately needs both.

Rants and Raves:

• The continued rise of AI-generated music hitting the charts, raising uncomfortable questions about creativity, authorship, and what "human" even means in popular culture.

• A rave for Viktor Frankl's Man's Search for Meaning, and why its lessons about purpose, suffering, and responsibility feel more relevant now than ever in a world optimized for convenience and automation.

As always, the episode ends where This Old Marketing lives best, at the intersection of technology, media, and the timeless human need for meaning, trust, and something real to hold onto.

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Get all the show notes: https://www.thisoldmarketing.com/

Get Joe's new book, Burn the Playbook, at http://www.joepulizzi.com/books/burn-the-playbook/ Subscribe to Joe's Newsletter at https://www.joepulizzi.com/signup/.

Get Robert Rose's new book, Valuable Friction, at https://robertrose.net/valuable-friction/ Subscribe to Robert's Newsletter at https://seventhbearlens.substack.com/

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This Old Marketing is part of the HubSpot Podcast Network: https://www.hubspot.com/podcastnetwork