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The one question you should NEVER ask ChatGPT

Why AI is making founders more isolated, more delusional, and worse at the one thing that actually matters: judgment.

A founder in a peer group gets asked: “How does someone build trust with you?”

His answer: “Me and ChatGPT are working on that.”

That’s where this episode starts.

Brooke Sherwood joins The Founder Hotline for the first time. We met at a retreat in Germany, and we haven’t stopped arguing about AI since.

This one gets into: why building with AI feels like progress but isn’t. The ADHD trap of instant dopamine through shipping things nobody asked for. What happens when AI takes all the easy work and your entire day becomes hard decisions. And why I stopped going to AI first and started calling my co-founder Dennis instead.

The deal at the end: next time you want to prompt a decision, call someone instead.

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