We’re celebrating a fun anniversary at Automattic today, our 20th, with a fun look-back. Gosh, it’s been quite a journey, and it still feels like we’re just getting started in so many areas.

In 2005, being a remote-first company was anathema to investors and business leaders* at the time; it was a scarlet letter that combined with our embrace of Open Source and the relative inexperience got us some funny looks and a lot of skepticism. I will be forever grateful to the true contrarians who bet on Automattic in our earliest days.

Even when it was clearly working the first few years, there was always the dismissal of “that won’t scale” that loomed like a remote startup Great Filter. These days I hear from friends who run incubators or do seed investing that almost every company they look at taps into remote talent.

It makes me think about what uncommon things Automattic does today that will be standard in the coming decades. We do our best to balance idealism with pragmatism, because even if you are on the right side of history, being too early can be as bad as being wrong.

I can’t predict everything that will change over the coming decades, especially with AI making the next few years particularly hard to predict. Still, I do know a few things that won’t change: everything flows from our people, open source is still the most powerful idea of our generation, growth is the best feedback loop, and no matter how far away the goal is, the only way to get there is by putting one foot in front of another every day. People will always want fast, bug-free software; instant, omniscient customer service when they need it; and experiences so intuitive that they usually don’t. And once they’ve had a taste of freedom, it’s hard to return to their previous state. (For more, see our creed.)

Our industry is highly cyclical, and I feel fortunate to have gained the perspective of a few bubbles and crashes, along with all the emotions that go with them. It’s undeniable we’re in the very early days — the command-line times — of an AI era, and though it will probably have its own bubble and crash cycles, it feels as significant to me as anything since we started. It’s more important than ever that we fight for open source and the freedom-enhancing side of technology. I’m committed to doing whatever I can to democratize publishing, commerce, and messaging, but there are many other areas of the human experience to cover… pick one to work on! It’s hard and rewarding work.

When I was working on an early version of one of our internal stats systems, it was really important to me that it showed rolling windows of the last 24 hours (daily), 168 hours, 4 weeks, and of course yearly. The rolling was important so you could see the impact of your changes as soon as possible. Then I felt called to add another: decade.

Some thought it was silly at the time, and it’s true that it initially served mainly as a way to display the cumulative number. But I wanted every time someone looked at one of these stats pages that they were reminded that we’re building for the long term. Our users and customers deserve nothing less. And now we have some statistics with 20 years of history, it has some useful comparisons as well!

In Ten Years of Automattic, I wrote:

There’s a lot more to do, and I can’t wait to see what a “20 Years of Automattic” post says. I’m a lucky guy.

Now we know! I’m still a very lucky guy, and can’t wait to build, learn, and share alongside a talented crew of like-minded hackers, dreamers, and doers.

* I’ll note that pioneers like Bob Young (Red Hat), Stephen Wolfram (Wolfram Research), Jason Fried (37Signals), and Mårten Mickos (MySQL) were big inspirations. Also, the entire Open Source community and most projects operated at least partially this way, which is why it seemed so natural to us as a second-generation Open Source company.