2025-06-21 10:59:54
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.
2025-06-19 00:55:25
I’ve been testing the developer previews of all the new Apple 26 operating systems, which I don’t recommend this early in the cycle, but I like to live dangerously. I’ve quickly become accustomed to Liquid Glass. The iPad windowing enhancements do make it feel more like a real computer, but I usually run things in full-screen mode. My favorite thing to play with so far has been the new Spotlight (what pops up when you press Command + Space) and related shortcuts.
I loved Alfred, I tried Raycast, but a general life goal this year is to simplify wherever I can, so I’ve been exploring the enhancements in the new Spotlight.
What I’ve found the most useful in the past is Alfred’s Open URL Action, which basically lets you type something like “gm united reservation” and it translates that into opening a Gmail search in your browser, with “united reservation” put in the URL in the right place to run a search.
The Shortcuts app in MacOS and iOS is amazing, which I’ve always known, but I haven’t played with it much. This was my chance! After a bit of tinkering, I got it to pop up an input form and then run the search. I Googled a lot to see if it could take input from the Spotlight search bar and every place said no, I’m not sure if this is new in MacOS 26 or not but I found the button that makes it work. It’s not as smooth as Alfred, but it’s pretty decent. I’m going to share a screenshot that shows my Gmail search shortcut that takes input from Spotlight — the key breakthrough was clicking the (i) menu on the right and finding the checkbox for “Receive Input from Search.”
I gave it a “gm” hotkey, pressed enter, and you get this in Spotlight.
Tada! Not as nice as Alfred but it gets the job done. My other shortcuts that people might find useful are LI for LinkedIn search, PY is Perplexity, YT for searching the history of YouTube videos I’ve watched, and AM for searching my Amazon order history. (Because I’m usually trying to find a link for something I’m recommending, or re-order an item.) Here are the search URLs for everything I’ve mentioned:
If you dug this, did you know WordPress also has a cool popup shortcut feature? In 2023, we introduced the Command Palette in the Gutenberg block editor and site editor. To access it on Mac, you press Command + k. I’d like to bring it to every admin page so it can function more like Spotlight or Raycast for WordPress.
2025-06-13 02:37:46
Happy to announce that the amazing Clay.earth product and team is joining Automattic. If you haven’t tried the app out yet, here’s a quick video to give you a taste.
TechCrunch has covered the broader strategy pretty well: One of the top requests we’ve heard from Beeper beta testers is they want to tie in more context, like a personal CRM, and some even requested Clay by name. We’ll keep the apps separate, as Clay also has some interesting team uses, but they will complement and integrate with each other as part of our all-in-one messaging strategy.
We share a vision to integrate Clay’s technology, which manages over 140 million relationships, as a layer across many of our products and experiences at Automattic. I’m excited to work with the founders, Matt and Zach, to bring this vision to life. I’ve always felt the missing primitive in WordPress’ content management data architecture was a scalable concept of a Person and Relationships outside of our user table.
Here’s the beautiful announcement on the Clay site and on Automattic’s.
2025-05-28 08:55:00
I’ve been thinking a lot about mimetic formation, how a thought becomes an idea, and how that idea gestates and evolves as it’s progressively shared in wider and wider circles.
During a recent product review of Day One, I was struck by how central the app is to my perspective on humans, relationships, and what we share. There are several layers to it, ranging from your innermost thoughts to what you share with the world. Each layer has its own context, challenges, and possibilities, and Automattic offers technology and products tailored to each.
1. Layer one is your internal thoughts. Your consciousness, what exists only in your mind, or what I like to call meatspace. This space is yours and yours alone. This generative space is at the core of human creativity and existence.
2. Layer two is triggered as soon as you put something into a medium, like writing it down. It’s everything that leaves your head, but is just reserved for you. In the past, we only had physical journals. Today, we have Day One as our strongest product in this space, but many people also have a private WordPress installation just for themselves. There are so many tools out there that help you create! Colors, brushes, canvases. Harper, for example, helps you write better — think of it as an open-source Grammarly, right now just in a few limited contexts, but in the future everywhere you write.
3. Layer three is you and someone else. This is everything you share with one other person, which is an incredibly sacred act. Shared journals on Day One, messaging on Beeper, DMs, private blogs with your best friend. A shared Google doc. This is its own special space. It has an intimacy and privacy that is core to the human experience. This is also phase 3 of Gutenberg, which is all about real-time co-editing and collaboration. This layer is the one I’m most excited about expanding in 2025 and 2026.
4. Layer four is sharing within a finite group. N+1. It’s a space of collaboration and brainstorming with families, tribes, and teams. P2, Linear, Github, group chats, and cozy communities. You lose some of the intimacy of layer three but gain more group intelligence.
5. Finally, we have the fifth layer. This is the public layer, where I have spent a lot of my time at Automattic. It is an extremely competitive space of social media and blogs: WordPress, WordPress.com, and Tumblr. Once you publish publicly, you open yourself up to the beauty and chaos of the wider world. The best reason to blog is comments, the people who find you and add to your thoughts, who you never would have imagined. This is a crucible, but makes your own writing and thinking so much better, it’s worth the mishegoss. 
This has been kicking around in my head and at layer four for a while. Thanks to Kelly Hoffman for helping me get this to layer five.
P.S. Happy 22nd birthday to WordPress! Very excited about the new AI team on .org.
2025-05-14 00:29:51
It’s a busy speaking season! I just spoke at the Intelligent Change summit, and will be at SaaStock in Austin on May 14, SXSW London, on June 4, Brilliant Minds in Stockholm, and WordCamp EU in Basel, Switzerland, on June 7.
