Rebooting the blog, 2026 edition

This site has run on WordPress in one form or another since the mid-2000s. Twenty-ish years, maybe six of them with any real attention. The pattern was always the same: a burst of posts, a redesign I was briefly proud of, then a year of silence while the plugins quietly went stale and the update notifications piled up like unopened mail. I wasn't running a blog. I was running a museum with bad security.

So this year I rebuilt it. Not another redesign — a reboot, with different rules.

The site has a job now. For years this was a junk drawer: conference recaps, half-arguments, posts written because I felt guilty about not posting. The new version exists to support the things I'm actually building — the guides, the tools for founders, the newsletter. If a page doesn't serve one of those, it doesn't get to live here. That test killed more old content than I expected, and I don't miss any of it.

Tighter beats bigger. I went through two decades of archives and kept maybe a tenth. The rest was cruft: dead embeds, hot takes about companies that no longer exist, posts that existed to feed an algorithm that has since died twice. Trimming it felt less like deleting and more like finally cleaning out the garage.

AI changed the math on maintenance. This is the part I didn't see coming. The reason the old site rotted wasn't laziness, exactly — it was friction. Every update meant logging into an admin panel I dreaded, fighting a theme I no longer understood. Now I talk to the site. I draft a post by talking through the idea, generate three angles on the fly and keep the one that survives, fix a redirect or restructure a section in the same conversation. The gap between "I should write that down" and it being live used to be a week. Now it's the length of a walk.

That last one matters more than the stack. Every previous reboot failed because maintenance cost more than I was willing to pay. This is the first version of the site that's cheaper to update than to ignore.

If your own site has been rotting on WordPress since the Obama administration: the tools finally caught up. It took a weekend. You don't need much.