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Strategy & The AI-Native Founder

How do founders use AI for strategy, decisions, and brutal feedback?

Founders treat AI less like a search engine and more like a smart colleague they can think out loud with: they paste in their strategy doc, pricing plan, or investor update and ask it to poke holes, list risks, and argue the other side before they commit. Because the default behavior of ChatGPT or Claude is to be agreeable, the trick is explicitly asking for criticism ('challenge my assumptions', 'tell me why this fails') and giving it real context about your business. Used this way, AI becomes a cheap, always-available second opinion that sharpens decisions instead of just producing text.

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4 resources.

Podcast

How to Use Claude Code as a Second Brain

Dan Shipper with Noah Brier (Every, AI & I) Sep 2025

A real operator demos turning Claude into a research and thinking assistant over 1,500 of his own notes, thinking-partner use at its most concrete (YouTube version linked in the post).

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