WordPress.com offers two modes of WP: WordPress and WordPress MS. For free and lower-priced accounts it runs a version of WordPress called WordPress MS, or WordPress Multisite, which is designed for super-efficient multi-tenant usage, which is what has allowed it to introduce hundreds of millions of people to WordPress and run at a huge scale. … Continue reading WP.com Simplification →

One of the projects that has been going very well within Automattic is Newspack, a vertical WordPress distribution tailored for publishers. Here’s the story of the Haitian Times:

To announce and celebrate the incredible engineering achievement of the Beeper team launching local bridges and their premium model we hosted a fun event in Automattic’s space in NYC. The app side of Automattic does some amazing work, and the applications themselves are pretty well known and reviewed, but many don’t know they’re part of … Continue reading Beeper and Automattic 20 →

In honor of Automattic’s 20th anniversary, and also since it’s been a few years, I joined Nilay Patel the editor-in-chief of The Verge on their Decoder Podcast. We talked about Tumblr and the Fediverse, how Automattic thinks about Ecosystem and Cosmos sides of the business, Automattic’s re-organization into cross-business functional teams and leadership, the vision … Continue reading Back on The Verge →

Scott Alexander, of Slate Star Codex / Astral Codex Ten fame, ran an Everything-Except-Book Review Contest 2025 in February. The prompt: “Submit an ACX-length post reviewing something, anything, except a book.” The submissions were collected anonymously in a giant 450-page Google Doc. I don’t think the winners have been chosen yet, but there is one essay that … Continue reading Alpha School Insider →

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 … Continue reading Automattic Twenty →

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 … Continue reading Alfred-like Shortcuts in Spotlight →

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 … Continue reading Play With Clay →

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 … Continue reading The Five Layers of Sharing Thoughts and Ideas →

A really beautiful interview.

It’s a busy speaking season! I just spoke at the Intelligent Change summit, and will be at SaaStock in Austin on May 14, Brilliant Minds in Stockholm, and WordCamp EU in Basel, Switzerland, on June 7.

It looks like the code that the newly announced Figma Sites is producing isn’t the best. There are some cool Figma-to-WordPress workflows; I hope Sites gets more people exploring those options.

Gravatar has always been about giving people control over their identity online. One avatar, one profile, synced across the web, verified connections, with a fully open API. Gravatar is a true open identity layer for the internet, and now for AI.  For developers, we’ve rolled out mobile SDKs and a revamped REST API that lets … Continue reading Remember Gravatar? →

I’ve checked off a bucket list item: I’m attending a Berkshire Hathaway shareholder meeting. It’s really an event! Thousands flock to Omaha, Nebraska, for the legendary Q&A sessions with Warren Buffett and shareholder deals. They’ve made it quite the circus, with every Berkshire Hathaway company having a booth of some sort, and typically selling their … Continue reading Berkshire Hathaway Meeting →

I know there’s been a lot of frustration directed at me specifically. Some of it, I believe, is misplaced—but I also understand where it’s coming from. The passing of Pope Francis has deeply impacted me. While I still disagree with the Church on many issues, he was the Pope who broke the mold in so … Continue reading Reflecting →

I’ve been blogging now for approximately 8,465 days since my first post on Movable Type. My colleague Dan Luu helped me compile some of the “greatest hits” from the archives of ma.tt, perhaps some posts will stir some memories for you as well: Where Did WordCamps Come From? (2023) A look back at how Foo … Continue reading Greatest Hits →

WordPress 6.8 Cecil is out, and it’s a great release. It’s unbelievable that it’s already been downloaded over 6 million times as I write this. That feeling never gets old. It’s a funny time in WordPress because there are a lot of really interesting open questions: Some of these broad changes are mixed. At one … Continue reading 6.8 →

The long-anticipated “Big Sky” AI site builder on WordPress.com went live today. It combines several models and can create logos, site designs, typography, color schemes, and content. It’s an entirely new way to interact with and edit a brand-new or existing WordPress site. This AI agent will make WordPress accessible to an entirely new generation … Continue reading AI Site Builder →

I was interviewed by Inc magazine for almost two hours where we covered a lot of great topics for entrepreneurs but almost none of it made it into the weird hit piece they published, however since both the journalist and I had recording of the interview I’ve decided to adapt some parts of it into … Continue reading Automattic Operating System →

It’s so funny that my random re-engagement with Radiohead re-emergence coincides with them doing a new entity that might mean something. I did a poll on Twitter and people preferred OK Computer to Kid A 78%!

With the world changing so quickly, it’s hard to find alpha, but the best way is by following the brightest thinkers. This CNBC interview with Ray Dalio and Marc Benioff is good, but it’s way better if you go to the livestream about 25 minutes in and see the full discussion without the editing. You … Continue reading Dalio & Benioff in Singaore →

One thing you’ll see on every host that offers WordPress is claims about how secure they are, however they don’t put their money where their mouth is. When you dig deeper, if your site actually gets hacked they’ll hit you with remediation fees that can go from hundreds to thousands of dollars. They may try … Continue reading Real WordPress Security →

One of my must-read newsletters for the past several years has been Lenny’s Newsletter, probably best known for its writing on growth and product management, which really means it covered everything you need to create a great company. It expanded into a really well-done podcast; Lenny has always had a knack for finding the best … Continue reading On Lenny’s Podcast →

It’s been fantastic being in the Philippines for this year’s WordCamp Asia. We have attendees from 71 countries, over 1,800 tickets sold, and contributor day had over 700 people! It’s an interesting contrast to US and EU WordCamps as well in that the audience is definitely a lot younger, and there’s very little interest in … Continue reading WordCamp Asia and Kumbh Mela →

In high school when 5% of your class doesn’t like you it’s like 3-5 people. Running a company of 1,700+ when 5% doesn’t like you, that’s 85 people! That fills a room. 150k followers and 5% don’t like you now you have a small stadium of 7,500 people. It’s still 5%.

“You didn’t just come up with a cool hash table,” he remembers telling Krapivin. “You’ve actually completely wiped out a 40-year-old conjecture!” There’s a delightful article on an undergraduate discovering an optimization in a very basic computer science principle.

I’ve been really enjoying the book Creativity Inc by Ed Catmull of Pixar, it was recommended to me by my colleague Dave Martin a while back and I finally got around to it. There’s an interesting story in it where George Lucas has asked him to develop a film editing system that was digital. While … Continue reading Ed Catmull on Change →

You may not have heard of Logan Bartlett, but he’s one of the most hilarious people on Twitter and does a really interesting podcast. (He had a cool episode with Marc Benioff recently.) We sat down for a discussion on managing through crisis, open source and AI, employee liquidity, future of WordPress, and more. You … Continue reading On Logan Bartlett Show →

I had a great chat with Sam Parr and Shaan Puri on their podcast, My First Million.