An agentic CMS, because it had to happen
I set out to cancel Squarespace. I ended up replacing it with Claude.
We can’t understand things fully until we’ve tried them ourselves in a scenario that counts.
Every now and then, I do a review of my digital subscriptions to see if they still make sense. This round I noticed I had a Squarespace subscription and a static hosting subscription running at the same time for my personal website. Back when I chose Squarespace, the convenience of not having to code a website myself was definitely what attracted me. This was a time when responsive websites, cross-browser compatibility, and just adding content yourself was a big timesuck. The cost reflects the benefit they had. Or had, anyway.
I decided to see if I could code my own website using modern AI tools. Completely custom, and a lot cheaper to host since I could use my static hosting subscription.
I landed on Astro, a framework that builds static websites from component templates. I used a mix of Claude Code and Copilot in VS Code to build everything. The reason was simple: I quickly run out of Claude usage when I’m not quite done with a project. Copilot has metered usage, and it’s cheaper too.
Turns out the current generation of LLMs are robust coding partners for this kind of work. They helped me understand Astro, set it up on my computer, create a proper Github repo, everything. I had a working version in about 30 minutes.
Not everything is static though…
I wanted my website to reflect my latest Substack articles, but since Astro renders static HTML, that wasn’t possible at runtime. What is possible is a script that pulls in my Substack feed and converts it into Astro template format.
So I set everything up on a Mac mini I have at home. Every day at 3am, a script runs that pulls the latest Substack feed, puts it in the code, builds the website, and deploys the new bits. A fully automated, up-to-date static website.
A few years ago, this would have required developers to build a platform for public use. Now I could do it myself.
Why not build this for my wife too?
I wasn’t done. My wife’s personal website was also on Squarespace, so I thought: why not build her one too? She designed the new site in Canva. Using screenshots and some careful prompting, I built another Astro site for her.
Then the problem became clear. I’d created a dependency: she’d need to understand VS Code and Astro templates to make changes. That wasn’t the way.
So I came up with an idea. The Claude desktop app has a feature called Dispatch that lets you send tasks from your phone to a Claude instance running on another machine. I changed the build script to work with Claude Dispatch directly.
Now my wife can send website updates as prompts from her phone. Claude evaluates the site and makes the changes. Once done, it deploys the site live! A full-fledged agentic CMS: it doesn’t just change content, it can also change form. Of course I don’t trust Claude completely, so I also built in a Github-based rollback system in case something goes wrong. All of it built into a Claude Skill that’s triggerable through asking.
So what?
People keep asking what LLMs are good for beyond chat and working on files. In this project, Claude replaced both the design and CMS capabilities that Squarespace provides. The experience is simpler and more personal.
This was too easy to build. I suspect we’ll start seeing more AI-enabled content management systems in the near future. We’ve already seen the start of it with Framer AI and Squarespace AI build flows.
Will they be cheaper though? I suspect not: convenience has always been what we pay for, not the technology underpinning it.
What’s next
I’ve already had my next idea. What if we build a site that watched its own analytics and proposed updates based on how people actually behaved on it? A website that automatically iterates on itself, quietly, in the background?
Probably a few more weekends and a lot more tokens away. But everything seems possible now. Let’s prototype it!