I had Claude analyze my writing business—here’s what it said

I uploaded my whole Substack zip file, my Metalabel backend, and my last four years of Quickbooks to Claude Code. Here's what it found.

This is The Ledger, a newsletter exclusively for paid subscribers at the collector tier and investors in my forthcoming book. Here, I share my process of building a media ecosystem and writing a book in public. It includes open access to my goals and financials and how I’m performing relative to those goals and financials.

This month I want to talk about a recent deep dive I did into the strategy of my business. Now that I have Claude Code installed on my computer, I dumped every possible data point into it—including my entire Substack zip file, the backend of my Metalabel account and WeFunder crowdfund, the members of my Slack channel, and my past four years in Quickbooks.

I asked Claude to analyze what was working, what was not working, and make an action plan for how to address the problems and grow beyond them. I had to go back and forth with it a bit to provide context, but I was ultimately impressed by its ability to make connections I would never have seen–like that subscribers from Italy were churning at a higher rate than other subscribers, which we were able to link to a cause.

Most of the actions on this list I’ll be working on behind the scenes and you won’t ever see the results. For instance, I already asked several writers I admire to recommend mine, and asked several others to unrecommend mine. That has already fixed some of the churn problems I was having. A lot of this I’m also ignoring or changing to suit my personality. For instance: I did create a drip email program, but I did not follow Claude’s recommended emails for it. I did start posting to Substack notes, but I have not posted anything resembling what Claude suggested I say there. Some of this is also just brainstorming: Possible ideas for the future of my business that I had it explore, but that I may or may not take.

If you’re interested in reading the rest, here’s Claude’s complete analysis: