Twenty Years at Automattic

When I started working at Automattic, it was just me and Matt, and two servers. A web server and a MySQL server. I knew the root password to WordPress.com. I needed it as I spent a lot of time tuning the MySQL server in those days, but I was thrilled when we got some real systems people on board like Barry. I have to admit to a certain sadness when I ran sudo and the password didn’t work, however.

When I started working at Automattic, many of my colleagues I work with now, were still in school. There was a time at the start of this year that my team had the first employee and the latest employee on it. I didn’t have any grey hair then, and well, I have some now, and I make jokes about the “old days” but there are quite a few of us boldermatticians.

I spent most of my time working in Vim, in an SSH session, but that’s changed to VS Code and Cursor in recent years. I tried the Vim extensions for those, but they never felt as good as the original.

Now, it’s the upstart AIs that are disrupting everything related to my job, but while it certainly feels like it’s making me a lot more productive, apparently it’s making me dumb too. Time will tell. Andrej Karpathy uses a number of analogies in this video at Y Combinator, but one thing that resonated with me was his comparing the state of AI to computing in the 60s. There were massive mainframes that people used thin clients (or punch cards!) to interact with them. In 2025, the AI is this brain in the cloud we talk to and ask questions of in a chat window. What’s it going to be like in another twenty years?

Anyway, I’m looking forward to seeing what happens in the next twenty years at Automattic!

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