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.

Automattic in 2006, when my luggage was delayed and I was wearing a British Airways tshirt.

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!

We’re out of water

That’s not really an announcement you want to hear from the pilot of your flight, but that’s what happened on my flight from Athens to Amsterdam recently.

A photo from the window of a KLM flight. The wing is clearly visible and the KLM logo is etched on the end. The plane is flying above the clouds with a clear blue sky above and a hazy horizon.

The pilot came on the intercom and informed his passengers there was no water to flush the toilets or wash hands. He said that’s the first time he’s had to make such an announcement. The flight had been delayed an hour at Athens, and then we spent 25 minutes on the ground while the congested air over Europe cleared. So I’m surprised someone forgot to fill the water tank.

Water bottles were provided, but I think everyone was glad to get to Amsterdam, even if several people missed their connection due to delays. Thankfully, the flight to Cork was late in the evening, and I had time to make it to gate D6. The airport was mostly closed down with only a few shops open, and passport control was backwards which was odd but worked well enough to get us to our destination. The police there were friendly and efficient.

I have to say, one thing I love about KLM is their free WiFi that allows messaging on WhatsApp, Messenger and other apps. It was great to message my family and friends while flying. It’s something that will make me choose KLM for a connection if all other things are equal. The flight to Cork didn’t have it, but the outgoing flight a week earlier did.

I was watching Top Gun: Maverick on my phone, downloaded on the Netflix client, and it looked like my flight would land before the film ended.

Screenshot from Top Gun Maverick showing the text "Hang on. We gotta get low."
Tom Cruise is flying a fighter jet while the world turns around him.

It was a late flight, the lights switched off in the cabin. I was staring at the action on my phone, with headphones hiding the drone of the aircraft. I was glued to the action on my phone, totally absorbed in it. Maverick shouts at his passenger, “Hang on. We gotta get low.” during a dogfight. A moment later, I feel my flight touching down on the runway at Cork Airport, and I look up in mild panic. Talk about immersion. Thanks, KLM! Perfect timing!