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How I Turn Highlights Into Revenue: The Strategic Power of Readwise + ChatGPT | by Simon Theakston | The Startup | May, 2025

softbliss by softbliss
May 7, 2025
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How I Turn Highlights Into Revenue: The Strategic Power of Readwise + ChatGPT | by Simon Theakston | The Startup | May, 2025
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Simon Theakston

Photo by Mauro Lima on Unsplash

“Wait… you remembered that quote from three months ago?”

That’s the kind of message I get from clients all the time now.

But no — it’s not my memory. It’s ChatGPT. More specifically, it’s what happens when you combine Readwise, audience avatars, and a CSV file full of curated insights. The result? A strategic writing system that turns buried knowledge into bottom-line impact.

In this article, I’ll walk you through the exact setup I use, why it works so well, and how it helps me deliver smarter, faster content for clients who expect more than just words on a page.

What I Do: Freelance Strategic Writing for Agencies and Tech Brands

Let’s start with the basics.

I’m a freelance strategic writer. My clients are founders, agency owners, and marketers who want to say something meaningful — but don’t have the time, clarity, or confidence to shape those thoughts into content that cuts through.

I write LinkedIn posts, lead magnets, white papers, and thought leadership content that speaks to their ideal customer with precision. But to do that, I need more than a writing brief — I need context, strategy, and a steady flow of…

Tags: ChatGPTHighlightsPowerReadwiseRevenueSimonStartupStrategicTheakstonturn
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