A video I’ve shared with friends recently is when Harry Mack ran into Ari, which was fun for me because they’re two of my favorite accounts to follow. Sorry I didn’t freestyle! I had to get back to do some work, which is why I got the monitor.
In other cool X/Twitter news, they launched an awesome feature today that lets you restrict replies not just to people you follow, but to people they follow as well. Nikita gave a hat tip to the conversation I had with Peter Levels / @levelsio.
If you host your WordPress on WordPress.com your AI agent can now manage your entire site, including updating posts or pages, making drafts, pretty much all the things you normally do with WordPress. Hook this up to your OpenClaw, Hermes, ChatGPT, Claude, Grok, whatever and have fun!
For the past few decades, WordPress was software you got from a cloud provider or web host, such as WordPress.com, Bluehost, Hostinger, or Pressable (the currently recommended WordPress hosts). You could self-host it on a Raspberry Pi or home server, but few people did.
The experience of downloading WordPress, as my Mom did, is that it unzips a bunch of PHP and various code files onto your desktop. Very confusing!
But now, thanks to incredible advances in WebAssembly (WASM), we can spin up a web server, a database (SQLite or MariaDB), and a full WordPress installation inside your browser in about 30 seconds. Instantly. No server needed. I introduced Playground at State of the Word in 2022.
These WordPress Playground containers are fully composable and atomic. You can track and roll back any change. Undo for everything. Stop thinking of WordPress as just on a web host and worrying about maintenance and management, and more as a self-contained unit of open source goodness, a fun little package where you own and control the code and data and can run it however you like.
How perfect is that for AI to work with? Playground makes WordPress local, fast, and trivial to spin up multiple instances, test code changes, and save them.
Next up, we’re going to add peer-to-peer sync, version control integration, and cloud publishing so other people can access it.
I believe this will take us from millions of WordPresses in the world to billions. Hosting isn’t going away; in fact, I think demand for cloud syncing will increase drastically as we radically open up what people can build on top of WordPress.
In an AI age where it’s trivial to spin up software from scratch, consumers will have to give much more thought to brands they trust to be in it for the long term. We’ve been relentlessly iterating on WordPress since 2003. I plan to work on it the rest of my life, and there’s a broad community of hundreds of thousands, if not millions, of people who make their living on top of WordPress.
On WordPress.com we offer 100-year plans and 100-year domains, and I believe we’re one of the few companies where that’s credible. It’s led by Zander Rose, who ran the Long Now Foundation (one of my favorite non-profits) from 1997 to 2023, a quarter century.
In core WordPress, we are obsessed with backwards compatibility. You can run plugins and themes written 20 years ago on today’s WordPress. I’ve stumbled on decade-old installs, and the built-in auto-upgrade took everything to the newest version.
In the next few years, there will be a Cambrian explosion of software and services. You’re going to have a lot of choices about where to put your most precious data and software. You should demand open source and bet on those who are clearly in it for the long-term.
Today, everyone gets a phone number and email when they grow up. That will expand in the future, everyone will have a domain and a WordPress. A part of the internet that you own.
Technology is best when it brings people together. Technology is best when it puts you in control, gives you ownership, digital autonomy, freedom, and liberty. That’s open source. It’s so exciting to see how AI is supercharging open source.
Now on the handle you’ll find a special surprise. Anyone recognize which WordCamp it’s from?
Ioanna and Hisashi run one of the coolest bars in the world; it’s been on my bucket list to visit. Hisashi is a big jazz fan, he even gifted me two records from a Japanese jazz pianist in Sapporo called Ryo Fukui.
I actually didn’t ski this trip despite the outfit because WordPress and Automattic had too much interesting stuff going on. So I’ll have to return to experience the famous snow of Niseko. And if you’re ever in the area, definitely make the trip to check out Bar Gyu! Maybe drop another WordPress sticker on the door.
Kudos to WP community member Matt Medeiros, who used AI to spin up a quick webapp to help his community track which streets had been plowed after that crazy snowstorm. Making local communities better is definitely part of the WordPresser ethos.
This year at Automattic has been intense. We kicked it off with two weeks of in-person AI enablement training, and there’s a great post about it now. I’ve been so impressed and inspired by my colleagues leaning in to learn and grow together in the most consequential time in software development in the past 40 years.
I want to start by thanking the Automattic board, and in particular General (Ret.) Ann Dunwoody, for encouraging me to step away from the endless work of being CEO of Automattic to focus on training and development. Ann, as one of this generation’s great leaders, did it herself before recommending it. She took the course shortly after becoming a four-star.
As I reflect on all the corporate training I’ve had, from the first class they made me take at CNET 22 years ago because my title had manager in it, to the workshops or intensive CEO things I’ve been lucky enough to be exposed to later, there’s one thing that really stands clear: You get out of any program what you put into it.
If you come in skeptical, distracted, or resentful, even if golden information is being dropped, it will bounce off you like water on a duck. You have to put yourself in a state of mind of extreme openness and enthusiasm, and take an earnest try at what the facilitators have designed and planned, no matter how cheesy, corny, obvious, or silly it might seem. Remember, their intention is for you to get something out of this, and they’ve done it before.
Holding that state of openness is also a catalyst for the teacher; they light up when students are willing to trust the process, and they’ll give you their very best. I originally titled this post “Complete Surrender” because that extreme statement helps me step out of the part of my mind that is always trying to challenge authority, remix conventions, or think I’m cleverer than others.
These programs are usually expensive, not just in dollars but in time you have to clear from other commitments, so don’t squander it by staying in your default modes of checking work, news, etc. Create a space for yourself to reflect, learn, and grow. It’s rare and precious.
The caveat, of course, is to choose your teachers well. CCL has been doing this since the 70s; they’ve figured a few things out. They’re Lindy. All of these programs change and evolve over time; they’re not carved in stone, but it’s particularly interesting to see what survives when something has been going on for a long time.
I’m also not religious about these things. I think of them as mental models that are new arrows in your quiver. You can use them as is, or, even better, mix them with something else you’ve learned to create something more useful and personalized to your context. The more you have, the more sturdy your latticework of understanding is, and the more robust your information framework will be when you encounter something novel.
There’s also some luck in the group; a bad apple can throw off the week for everyone. My cohort had people from a variety of industries like healthcare, paper products, car rentals, and business process outsourcing from all around the world, including Egypt, Brazil, Saudi Arabia, and all across the US. It would have been easy for people to be guarded, but everyone really leaned in. I think we had so little network overlap that people felt more comfortable opening up. And, of course, it was endlessly fascinating to learn about the challenges across vastly different industries, as well as the universal commonalities that arise whenever you try to vector a group of humans towards a common goal.
One of the inspirations I drew from Ann’s book, A Higher Standard, was the extent to which the Army invests in training and development, sometimes sending people to programs for years before they move into a new role. They’re always thinking about the next generation.
A big theme for me in 2026 is learning: Last month at Automattic, we did our first two-week in-person AI Enablement intensive at our Noho Space, and the feedback was incredible. On the WordPress side, this year we’ll have thousands of college students enroll in our new WordPress Credits program to earn credits toward their degrees. The number of cities where WP meetups are held is on track to double; it’s clear people are hungry for opportunities to learn and grow.
People have been asking my takeaways from the course, and it’s been hard to summarize, but I came away with big lessons on how my comfortable and improvisational presentation style can come off as not having a solid plan or being prepared, the importance of exercise and nutrition to have the energy you need as a leader, and the importance of being on time and what that signals to others. Great feedback is a gift and a mirror, allowing you to see things you might miss about how you show up to others. In the course, we made plans, and since then, I’ve been experimenting with integrating these learnings and others into my day-to-day. I feel like it’s really had an impact.
So in closing, when you’re a busy executive, there’s never a good time to step away for a week, but I highly encourage every leader to at least once a year invest in themselves and let your colleagues and loved ones know that for a few days you’ll be really focused on a departure from your quotidian day-to-day and work on growth. It’s hard but worth it.
Stephen was doing the remote CEO thing decades before I imagined Automattic. He spoke at Automattic’s Grand Meetup in 2019 and one of my favorite memories was seeing him at the silent disco after-party. We also did an episode of the Distributed podcast together.
Since he started engaging more deeply earlier this year, I’ve gotten a lot of joy from seeing him interact with teams across the company, asking questions in an incisive, inquisitive way that helps break down problems. We just finished up several hours of a deep dive into our board topics with several hundred Automatticans participating.
Tonight was a lot of threads connecting for me. At Automattic’s Noho Space we hosted an event for Martin Scorsese’s new documentary about Pope Francis, called Aldeas. There was a point in my life when I wanted to become a priest, and I had been inspired by meeting a Franciscan seminary student. I took it very seriously and considered that as a path for my life, but some combination of jazz and girls made me realize that the priesthood was not my destiny.
The jazz led to building websites for Houston jazz musicians, which led to coding, which led to WordPress, which after a lot of twists and turns led to Automattic acquiring Tumblr. One of Tumblr’s greatest memes was Goncharov, directed by Martin Scorsese. The only reason Automattic, as a distributed company, has an office in NYC is because of the Tumblr acquisition. The office is filled with art from Tumblr artists so I had the very surreal experience of talking after Martin Scorsese, who at 83 is sharp as a tack and a gifted speaker, a few feet away from a Goncharov poster about how my Catholic upbringing led me down the path of starting WordPress, and how Pope Francis’ life inspired the WordPress Jubilee and reflection. Full circle.
Yesterday I had the great honor and privilege of attending a colleague’s 70th birthday party. You may not have heard his name before, but Kinsey Wilson has been at the center of shaping journalism with a movie-worthy career that started at the bottom as a crime reporter in Chicago, and has taken him to the highest echelons at NPR, the New York Times, and, most recently, we’ve been lucky to have him at Automattic.
Kinsey brings a journalistic curiosity and passion for finding truth, paired with a deep optimism and creativity for seeing around the corner for how technology can transform how we consume and produce media.
While his Wikipedia page or biography provides appetizers to some of what he’s done, Kinsey has led such a rich and beautiful life that any attempt to summarize it ends up being criminally reductive. The best you can hope for is to give a taste of his person through vignettes.
A beautiful snippet from the montage of accolades at his birthday was how Kinsey was someone you’d follow into battle. I’ve learned so much from seeing the empathy, candor, and integrity he brings to every team he leads, which engenders an incredible loyalty I’ve rarely seen in my career. When he left NPR, 62 colleagues made an “Infinite Kinsey” website of accolades.
That sort of thing is rare, and it’s been an honor and a privilege to work alongside him to democratize publishing.
One of those colleagues, Elise Hu, introduced us while he was at the New York Times and while my intention when I first met him was to get more WordPress at the Times, my imagination was sparked by thinking of how he could bring his experience to help shape WordPress and Automattic, hence my pivot into recruiting him.
Kinsey’s impact on journalism (and podcasting!) at NPR and New York Times is easy to understand, but less well-known is how he came into Automattic and got deep into understanding WordPress and seeing it as a platform that could enable the newsrooms and journalists to accomplish their mission in a more efficient way with the project he leads, Newspack.
Newspack and its team’s close relationship to customers invents solutions on top of WordPress that delight its users and percolate and influence everything we do at Automattic. They’re one of the teams that sets the bar for others in the company.
I’ll try not to be too tech-bro optimist and say that 70 is the new 40, but I look forward to seeing the ripples that you have on the future of publishing for many years to come.
The story of what Bending Spoons has built is very impressive, and I’m a customer of theirs through Evernote, WordPress uses Meetup a ton. I think Automattic’s Noho office used to belong to Meetup. They’ve built an incredible engineering and product culture that can terraform technology stacks into something much more efficient. I think their acquisitions of Vimeo and AOL are brilliant. This interview with Luca Ferrari on Invest Like The Best goes into their story and unique culture. I also always love a good Matrix reference. 🙂
I just got off stage from the great dev/ai/nyc event with John Borthwick, we had a wide-ranging discussion that we’ll post online soon. We had hundreds of people in the room and hundreds on the waitlist… the energy in NYC is electric!
This week, the Automattic Creed received its first-ever update, which I’ll describe as a minor point upgrade. This is the sentence before and after.
I am in a marathon, not a sprint, 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.
Is now.
I am in a marathon, not a sprint; no matter how far away the goal is, the only way to get there is to put one foot in front of the other every day.
As I wrote earlier in our internal P2s, “Always great to bury a gerund.” And now we have a semicolon! It’s all quite exciting. For the backstory, please read Why Your Company Should Have a Creed. I said in 2011 “I’m sure that it will evolve in the future” but I didn’t expect it to be 14 years before the first revision.
Internally at Automattic we’ve debated updating the Creed in dozens of conversations and blog posts, usually in the context of adding a sentence, which I still hope will happen in a future version. But this is a minor update. We’ll see when Creed 2.0 happens.
The private Automattic intranet is one of the most delightful things about working there, which you may consider as well.
When a linked page disappears, the plugin helps preserve your user experience by redirecting visitors to a reliable archived version. It also works proactively by archiving your own posts every time they’re updated, creating a consistent backup of your content’s history.
I’ve been doing this manually on my old archives, fixing broken links and tending the garden. But we can make it all automatic. 🙂
It’s a bit of Automattic lore, but although I founded the company in June 2005, CNET asked me to stay on for a few more months to finish out some projects, which I did. Our HR systems have me as the second employee, after Donncha O Caoimh (still at the company!) So today is my 20th anniversary at Automattic! It’s 20 years since I started hacking on Akismet, our first product, and on WordPress.com.
The team gave me a sweet surprise! I’ve been fighting for the open web for 20 years, and hope to do it for at least 20 more. There’s a lot of exciting behind-the-scenes stuff happening inside Automattic that also made this day special, but one significant thing is public.
I don’t think WP Engine employees or investors were aware of the gaslighting they did, hopefully some of this is enlightening. And there’s a lot more discovery to go!
