Happy Birthday Anil

Asides

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, web standards, interoperability, and much more. His writing is incisive and insightful. I see a core flame of empowering independents throughout his career that very much aligns with the philosophies I aspire to. Please follow him if you don’t already, and happy birthday Anil! It appears that I have linked to him 15 times on my blog before this post, and he has commented 17+ times, the first in 2005, so we have some history! Since I started drafting this he published his Five for Fifty birthday post.

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 the same tune […]

If they’re used to stories about surgeons getting completed with the string “man”, then that’s the direction their thoughts will always go… Also, how come God can’t make humans speak normally? Everything they say is full of these um dashes!

Which leads to a hat tip to Brian Gardner on the incredible McSweeney’s Em dash responding to the the AI allegations.

So next time you read something and think, “AI wrote this—it has a lot of em dashes,” ask yourself: Is it AI? Or is it just a poet trying to give you vertigo in four lines or fewer?

Are you a WordPresser?

Asides

You might be a WordPresser if…

  • You like to have freedom and control over all your software.
  • You don’t mind taking a bit more time to invest in tools that give you agency.
  • You like inserting little opportunities for joy in everyday interfaces.
  • You want future generations to grow up with a free and open web.
  • You like to tinker, hack, mod, customize, and share what you learn.
  • You are impeccable with your word.
  • You think software should have a little soul in it.
  • You love giving other people superpowers, teaching them not to need you anymore.
  • You appreciate a good plan but want to be able to color outside the lines, or completely reimagine the canvas altogether.
  • You think technology is best when it brings people together.
  • You get excited by updates.
  • You want your corner of the web to truly be yours, not generic or commoditized slop.
  • Your friends come to you to learn about new stuff.
  • You leave things better than you find them.
  • You fix things as you find them, it’s never someone else’s problem.
  • You know a single comment can light up someone’s day.
  • You’ve gotten out of the house to meet other people into WordPress.
  • There’s a Wapuu item or sticker somewhere in your life.
  • You “view source.”
  • You know the difference between owning your content and being a digital sharecropper.
  • You’ve drunkenly registered a domain, and have more domains than websites.
  • You’ve snuck an easter egg in a slug.
  • You have a Gravatar, and it’s also a museum of all your email identities over the years.
  • You think code can be poetry.

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 we’d make software so good they’d adopt it. The New Yorker is one of them. If you enjoy words that make your brain tingle, make sure to also follow Automattic’s publications, Longreads and Atavist.

Summer WordPress Update

WordCamp

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 announcements:

  • Traffic to WordPress.org is up, and we’ve brought the plugin queue from months to basically a few days.
  • Previewed Block Comments and the upcoming Command Palette feature in 6.9.
  • Shared some fun AI experiments, including Felix’s AI chatbot demo, Automattic’s new Telex block creator, and more.
  • Got to announce details for the next two flagships:
    • WordCamp Asia 2026: Mumbai, India, from April 9th to 11th.
    • WordCamp Europe 2026: Kraków, Poland. June 4th to 6th 2026.
    • WordCamp US 2026: Phoenix, Arizona, from August 16th to 19th. 😅

Give it a watch!

Think Different

WordPress

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, with blogging. In the 90s I was running around the Vallley trying to explain to everyone that blogging was going to change everything, all I got was blank stares from people who said “we don’t do that.” They of course eventually did do it. But at first the ideas seemed foreign, unreasonable.

And in light of the news of Typepad shutting down, note that WordPress has a Typepad importer. A big advantage of putting your content into an open source platform like WordPress with an active community, vs just static pages or something custom, is that you’re getting constant upgrades “for free” as we maintain and iterate on the software, enabling new APIs or things like allowing your AI to talk to your site.

WordPress is built by a community of people deeply passionate about backwards and forward compatibility, radical openness so it’s easy to get things in and out of it, and relentless iteration building for the long term. Despite literally billions of dollars spent trying to kill or crush WordPress, and frequent proclamations of its death, we keep trucking along and doing our darndest to make the web a bit more open and free every day. It’s a life mission of many people, including myself.

The Future of WordPress and AI at WCUS

WordCamp, WordPress

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 is even more valuable this year, as things are changing so quickly. If you know anyone in or near Portland, Oregon have them get a ticket! Here are all the other AI-related talks:

MCP NYC Hackathon

Events

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 to speak at it and serve as one of the judges. For those unfamiliar, MCP stands for Model Context Protocol and enables AI models to interact with multiple tools in a more efficient and structured manner, allowing developers to create sophisticated agents that can handle complex tasks. And it’s only 8 months old! The energy in the room was electric—hackers collaborating, iterating, and demoing groundbreaking projects in just a few hours. (I would love to see the results of a longer overnight or all-weekend hackathon.)

For a wrap-up of the winners, check out this great X/Twitter thread by Alex Reibman. The first-place winner, Levels AI, orchestrates different AI/ML models to solve specific business requirements without needing heavy manual coding or specialized teams. Essentially, it’s models creating more models—a meta-approach to AI that could streamline operations for companies of all sizes. Yusuf Olokoba said the name was inspired by Pieter Levels, which is pretty cool. I wanted to note one team in particular: BeepResearch, which used our early access Beeper API and local MCP.

Judging the entries was tough! People built so much cool stuff in a really short period of time. I always say technology is best when it brings people together, and this was a great example of that, and makes me very excited for Contributor Day at WordCamp US next week. (Which has such a stacked AI program as well.) Hopefully some people who enjoyed the office might consider getting 24/7 access.

I also just want to take a beat and say how amazing it is that I’m blogging this, on a United flight from Houston to San Francisco I’ve taken a million times, on a plane 36,000 feet in the air and technology is amazing. I can’t wait until United has Starlink!

Also last week the WordPress AI team shipped its MCP adapter!

WP.com Simplification

Automattic, WordPress, WordPress.com

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. (It was initially called MU, for multi-user, but we had to change it because someone squatted the name WPMU and built a business on top that was confusing users with commercial products. Such is my curse.) It revolutionized the hosting industry in a number of ways, including acclimating customers to per-site pricing instead of unlimited domains and raising the bar for what a host would manage for users so they didn’t have to worry. It has also provided a highly secure base login, which allows us to offer popular SaaS services, such as statistics and anti-spam, to all WordPress users, regardless of where they’re hosted.

At higher-priced plans you’d get access to not just a curated set of plugins and themes but the ability to install anything you like from the ecosystem, which invisibly switches your account to WP.cloud in the backend that supports unlimited plugins and themes and custom code, in a way that’s still multi-datacenter and maintenance-free. This has been very successful and works great for a ton of customers, but it still puts an asterisk when you recommend WordPress.com to someone because they’d need to be on one of the higher-priced plans to get an experience of WordPress with custom plugins and themes.

For the first time ever we’re running a summer special where every single paid account gets that full WP.cloud experience with full customization and control. It’s a test we’re running until August 25th. It’s WordPress, without the asterisk, without limits, implemented in a way that’s intuitive and safe for novice users, while also being extremely powerful for developers. If you haven’t checked out WP.com in a while, it’s a great deal starting at just $4 per month. I’m curious to see the results of how this goes. We also have a number of more radical things I’m eager to try out! It’s a great time to reimagine what you’re doing from the ground up and question your longest-held beliefs, as AI has really put people in a more experimental and open mindset.

Beeper and Automattic 20

Automattic

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 Automattic, so it was a good opportunity to tell that side of our story a bit. Here’s the video from the event:

And if you’ve ever wanted to get better control over your instant messages, regardless of what network they may be on, definitely check out Beeper. I find it especially useful on desktop, like a Superhuman for messaging.

Back on The Verge

Automattic, Press, WordPress

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 of Clay as a personal CRM and Beeper as the super-human messaging app that puts control in the hands of users, Newspack, the future of websites, the obligatory coverage of the alleged WP Engine trademark violations and their subsequent preemptive suit, and much more. Please give it a listen! They chose the title “Why Automattic CEO Matt Mullenweg went to war over WordPress.”

Speaking of Beeper, we’re going to do a fun event for the next-gen version that’s launching on July 16 in New York City in NoHo. I’ll be there along with Beeper CEO Kishan Bagaria and some of the best and brightest in New York’s tech and creative class. If you’re a Beeper early adopter (or would like to be) and want to attend, leave a comment! We’ve held back some invites for cool folks like readers of ma.tt. 🙂 It’s like getting on board with WordPress in 2004.

Alpha School Insider

Education

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 has been making the rounds and getting shared more, and that’s Alpha School and “2-hour Learning” powered by AI, a parent’s perspective on Alpha School, a set of “AI-powered” schools in Texas and Florida.

It’s worth reading the entire essay, but I wanted to excerpt a few points I found interesting:

After twelve months I’m persuaded that Alpha is doing something remarkable—but that almost everyone, including Alpha’s own copywriting team, is describing it wrong:

  • It isn’t genuine two‑hour learning: most kids start school at 8:30am, start working on the “two-hour platform” sometime between 9am-930am and are occupied with academics until noon-1230pm. They also blend in “surges” from time to time to squeeze in more hours on the platform.
  • It isn’t AI in the way we have been thinking about it since the “Attention is all you need” paper. There is no “generative AI” powered by OpenAI, Gemini or Claude in the platform the kids use – it is closer to “turbocharged spreadsheet checklist with a spaced‑repetition algorithm”
  • It definitely isn’t teacher‑free: Teachers have been rebranded “guides”, and while their workload is different than a traditional school, they are very important – and both the quantity and quality are much higher than traditional schools.
  • The bundle matters: it’s not just the learning platform on its own. A big part of the product’s success is how the school has set up student incentives and the culture they have built to make everything work together

…Yet the core claim survives: Since they started in October my children have been marching through and mastering material roughly three times faster than their age‑matched peers (and their own speed prior to the program).

One of the surprises doesn’t come until Part 4 of the essay:

Incentives

People REALLY don’t like the idea of incentivizing kids to learn.

Roland Fryer, who has done extensive work on what works in incentivizing students, quotes a 2010 Gallup poll that found that only 23% of American parents support the “idea of school districts paying small amount of money to students to, for example, read books, attend school or to get good grades” (76% opposed the idea with only 1% undecided).

There are not many things that 76% of Americans agree on. Only 69% of Americans believe another Civil War would be a bad thing. Only 78% agree that American independence from Britain was the right choice. People REALLY don’t like paying kids to read books.

I hope that gives you enough of a hook to read the entire essay, it was quite good and provocative to many assumptions I’ve had about education.

Automattic Twenty

Automattic

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.

Alfred-like Shortcuts in Spotlight

Apple, WordPress

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.

Play With Clay

Automattic

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.

The Five Layers of Sharing Thoughts and Ideas

WordPress

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.