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Cortex

184: Writing the Newsletter Tech Executives Read, with Ben Thompson

October 21, 2026 • 1h 6m

Summary

⏱️ 14 min read

Overview

Ben Thompson, creator of Stratechery, discusses his 13-year journey building one of tech's most influential publications as a one-person operation. He shares his complete workflow for producing daily updates, weekly articles, podcasts, and CEO interviews, while maintaining creative control through his own publishing platform, Passport. Ben opens up about the challenges of writing daily, the importance of protecting creative focus, and why AI has fundamentally changed how he builds tools for his work.

The Evolution of AI-Powered Workflows

Ben reveals a significant shift in how he approaches software and productivity tools. Rather than subscribing to pre-built apps, he and his team now use AI to create custom solutions for specific workflow problems. This represents a fundamental change in how creators will work in the future—building personalized tools rather than adapting to generic software. Ben discusses how this trend will impact software companies as their best customers increasingly build their own solutions.

  • AI coding tools like Claude and ChatGPT have enabled creating custom apps for specific workflow needs
  • Previously would pay for expensive software, but now increasingly just builds custom solutions
  • Great software that solves problems may increasingly never be released publicly
  • Must explicitly tell AI tools there are no privacy concerns when building on private networks
" I'm making incredible apps, not that they're incredible technically, but they are tailor fit to solve specific problems that we have, which by definition makes it the best possible app. "
" I was previously the best customer for software developers because I would buy expensive software, I would gladly pay a subscription whatever might be if that software solved my needs and I'm increasingly just not a customer for new software because I'm just going to make it myself. "

The Philosophy Behind Stratechery

Ben explains his core philosophy for Stratechery: it's fundamentally a journal of his attempts to understand the technology industry, not a publication shaped by audience demands. This approach has been crucial to avoiding burnout while producing over 200 updates per year. He emphasizes that the moment creators start catering to their audience rather than their own interests, they begin to burn out. This audience-independence has allowed Stratechery to maintain quality and influence for over a decade.

  • Stratechery is fundamentally a blog, with email as the easiest delivery mechanism for readers
  • Writes what's interesting and important to him, not what audience wants—avoiding audience capture
  • Goal is to trigger readers to think, even if they disagree, strengthening their own understanding
  • Started with limited free content so paid subscriptions felt like getting more, not being taxed
" The moment I start catering to them or letting that influence what I write about or my views, like audience capture is obviously a real thing. And not only would that be bad in terms of the content that I do, but it would be bad for me. And that's when you start burning out is when you do stuff that it's not for you it's for someone else. "
" I am selling an ongoing trigger to make you think. I'll say what I think, I'll try to lay it out very logically. If I get it wrong, I'll come back and not just say I got it wrong, but also say this is the thought process that led me to this conclusion and here's where I messed up. "

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