The Newsletter Operator’s ThinkWithAI Playbook

Turning AI into a Strategic Thought Partner for Growth and Monetization

Growing and monetizing a newsletter isn’t just about writing.

It’s about making the right decisions at every stage, from audience growth to pricing to automation.

But most operators rely on trial and error, following generic advice instead of figuring out what works for their specific situation.

This ThinkWithAI Playbook is different.

Each prompt is designed to act as a thought partner, not a script.

Instead of giving you surface-level tips, it helps you pressure test ideas, challenge assumptions, and refine your strategy so you’re always making the highest-leverage moves.