I recently came across a few old business cards I designed back in 1999. The first ones were for my services as a saxophone player: A few notes: This was for my “design” business: I would also design business cards for friends, here’s one for my friend who was a percussionist and vibraphonist, Chase Jordan: 

Just got word that the court dismissed several of WP Engine and Silver Lake’s most serious claims — antitrust, monopolization, and extortion have been knocked out! These were by far the most significant and far-reaching allegations in the case and with today’s decision the case is narrowed significantly. This is a win not just for … Continue reading Legal Win →

It’s always fun to see someone pushing the limits of the web experience, as I reminisced about Flash and Dreamweaver the other day. The new website for Posthog is a delightful rabbit hole to explore, akin to a Meow Wolf, with meticulous care and craft applied to every corner of the product in a way … Continue reading PostHog →

When I studied economics, one of the concepts that struck me the most was the concept of externalities. This International Monetary Fund post explains it well. In short, externalities are costs or benefits of an economic activity that affect third parties who did not choose to incur them, leading to a divergence between private and … Continue reading Account for Externalities →

It’s been a busy (and tragic) week but one of the more interesting things to launch was the Really Simple Licensing standard. I have a lot of scars from the web standards wars, so I’m hesitant to dive back in, but this is from a lot of the early Web 2.0 people, as TechCrunch writes … Continue reading Really Simple Licensing →

I had a great chat with Matt Cromwell and Zack Katz on WP Product Talk today, mostly about the intersection of AI and WordPress, give it a watch!

It’s New Apple Stuff day, so the headlines are being dominated by that, but it’s worth taking a step back and paying homage to the site that has been the front page of tech news for two decades now, Techmeme. I’ve been a daily visitor since it started, and I appreciate how they pair the … Continue reading Techmeme 20 →

A few interesting reads or listens:

My sister Charleen sent me this meme with the note “Someone needs to draw you in there with your arm up 🤣🤣🤣” It’s a nice ode to the Dries essay on Maker/Taker problems. Well, thanks to the magic of AI, I asked the Nano Banana AI Studio to “make it so on the bottom one … Continue reading Maker Taker →

Chris Young, who is otherwise famous for being a co-author of the 2,438-page cookbook Modernist Cuisine or centrifuging steaks and drinking them, is one of the friends who, over the years, has told me I have to watch Breaking Bad, the TV show. When I was in Marrakech for a few weeks earlier this year, and it was a … Continue reading Breaking Ribs →

If my calendar is correct, one of the OG bloggers Anil Dash is turning 50 today! His blog, which I believe has been active since 1999, inspired me with how he effortlessly transitioned between his top-tier fandom of Prince and his thoughtful commentary on the nuances and second-order effects of what we were doing with blogging, micro-blogging, … Continue reading Happy Birthday Anil →

Simon Willison has vibe-coded 124 useful tools.

There are many levels to the excellent Scott Alexander satire of God, Iblis (Islamic word for devil), and Dwarkesh Patel, one of the best new podcasters of this era. There are people who have gone their whole lives without realizing that Twinkle Twinkle Little Star, Baa Baa Black Sheep, and the ABC Song are all … Continue reading God & Devil Debate HI →

You might be a WordPresser if… If you identified with two or more of these statements, I am afraid to inform you might be classified as a WordPresser. What did I miss?

The New Yorker is always good, but they’re having a bit of a victory lap as they celebrate their centennial. This article on the vaunted fact-checkers is such a delight, with so many in-jokes and back references it’s hard to keep track. When I started WordPress, I wrote down five publications that I hoped someday … Continue reading Fact Checkers →

I’m still buzzing from an incredible WordCamp US this week, from contributor day to the closing party the vibes were right and it was amazing to connect with fellow travelers in the journey towards creating a more free and open source internet. Before our open town hall Q&A I was able to make some fun … Continue reading Summer WordPress Update →

Pretty heads down at WordCamp US, which has had amazing energy and talks so far. I wanted to take a moment to note two things, first being a great essay from Dave Winer asking people to Think Different about WordPress. I’ve done this before — asked people to think differently about things, like public writing, … Continue reading Think Different →

The presentations for WordCamp US are just a few days away! We have some really exciting keynotes including Danny Sullivan from Google, John Maeda from Microsoft AI, and Adam Gazzaley (one of the top neuroscientists in the world) from UCSF. I think being in the room and able to meet the speakers and ask questions … Continue reading The Future of WordPress and AI at WCUS →

My good friend Tim Ferriss has launched a new card game with the Exploding Kittens folks, I just ordered it and you should do so too. It’s a lovely way to share an evening with a few friends.

Over the weekend, Automattic/Beeper had the pleasure of hosting and sponsoring the Build the Future MCP Hackathon in New York City organized by Adam Anzuoni, alongside Anthropic, Stainless, WorkOS, Smithery, and MongoDB. As someone deeply passionate about open-source technology and the potential of AI, I was thrilled to not only support this event but also … Continue reading MCP NYC Hackathon →

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.