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.

What an exciting time to be alive. I was hipped to Deepseek by Andrej Kaparthy’s tweet the day after Christmas, it was clear then that something big had happened and that it was truly open source and open weights (not this fake Llama stuff). It’s been fun to see the rest of the world catch … Continue reading Boom & Deepseek →

It’s another year, I have ordered all the things and tested all the cables, there’s a little bit about tech and a little bit about life. Here’s what made the cut, now I’m going to be factoring in weight of everything as well. The flat-lay this year was taken at my sister Charleen’s house, where … Continue reading What’s in My Bag, 2025 →

Forty-one is a nice birthday because it doesn’t feel like too much pressure. For forty I did a big eclipse thing that ended up amazing, this year I’m replicating what I did a few years ago and celebrating in New York, Houston, and San Francisco. My birthday today has already been lovely. Saw the amazing … Continue reading Matt 4.1 →

I wrote over on WordPress.org about breaking the status quo with a Joost/Karim fork. It’s a perfect time as Automattic is re-focusing its work while the legal stuff is going on.

WordPress.com launched a new update to Studio this week, and we’re already seeing some buzz. Studio is our free and open source app for local WordPress development, enabling you to spin up unlimited WordPress sites on your personal computer. Through its newest feature, Studio Sync, you have complete freedom to: Studio is an excellent tool to have in your … Continue reading Studio Sync →

When Inc Magazine reached out to have David H. Freedman (website powered by WordPress) write a feature piece I was excited because though Inc wasn’t a magazine I have read much since I was a teenager, David seemed like a legit journalist who usually writes for better publications like The Atlantic. I opened up to … Continue reading Inc Hit Piece →

The talented Felix Arntz has given an incredible Christmas gift to the WordPress community with his fast, light, and accessible Snow Fall plugin, which is live on this site and you can install on yours. I hope everyone is having a happy holidays! Search for “snow fall” in your plugin dashboard and install his version, … Continue reading Falling Snow →

It’s a dream come true being here in Tokyo for State of the Word 2024. We’re going to be in an amazing venue that looks over the city. Most of WordPress and Automattic’s senior leadership is here, and we’ll also have several hundred folks from the local community and press. We’ve gotten so much inspiration … Continue reading State of the Word Tokyo →

My father attended University of Houston, and it’s where I went to college to study political science, I started WordPress when there, and then dropped out after two years to move to San Franisco. It was fun seeing UH Magazine feature an article about my journey from a University of Houston student to co-founding WordPress and leading … Continue reading UH Magazine, Revisting My Alma Mater →

This week, DrupalCon Singapore is bringing together an incredible community of Drupal platform creators, developers, and supporters.  Last year, I had the chance to share the stage with Dries Buytaert, the founder of Drupal, and the conversation stuck with me. It highlighted the profound impact we can have when communities like ours come together to … Continue reading DrupalCon Singapore →