Category Archives: WordPress

The open source publishing platform I co-founded — development, releases, community, and the ecosystem.

EmDash Feedback

AI, WordPress

So, two other Matts at Cloudflare announced EmDash — the spiritual successor to WordPress that solves plugin security.

(Is it nominative determinism or a simulation glitch that everyone trying to terraform the web has some variation of “Matthew” in their name? I was in a call set up by Matthew Prince, talking to Matt Taylor and Matt Kane, with my right hand there, Matías.)

First, I’m going to tell you why this isn’t spiritually tied to WordPress at all, then why they haven’t solved plugin security, and finally offer some suggestions.

The Spirit of WordPress

WordPress exists to democratize publishing. That means we put it everywhere. You can run WordPress on a Raspberry Pi, on your phone, on your desktop, on a random web host in Indonesia charging 99 cents a month, and you can run it scaled up on AWS or across multiple datacenters.

The same code. When you download WordPress Playground you’re running the same code that’s being attacked a thousand times a second at WhiteHouse.gov. That’s what we mean when we say democratization.

It’s all built on open source and web standards. You can run it anywhere; there’s no lock-in.

That’s why we do what we do. It’s really hard. You can come after our users, but please don’t claim to be our spiritual successor without understanding our spirit.

The Spirit of EmDash

I think EmDash was created to sell more Cloudflare services. And that’s okay! It can kinda run on Netlify or Vercel, but good stuff works best on Cloudflare. This is where I’m going to stop and say, I really like Cloudflare! I think they’re one of the top engineering organizations on the planet; they run incredible infrastructure, and their public stock is one of the few I own. And I love that this is open source! That’s more important than anything. I will never belittle a fellow open source CMS; I only hate the proprietary ones.

If you want to adopt a CMS that will work seamlessly with Cloudflare and make it hard for you to ever switch vendors, EmDash is an incredible choice.

Claimed Plugin Security

In another example of them not understanding the spirit of WordPress, the fact that plugins can change every aspect of your WordPress experience is a feature, not a bug! And their sandboxing breaks down as soon as you look at what most WordPress plugins do.

I know we get a bad rep because there are 62k plugins with wildly variable engineering quality, and more every day, and when one installed on 0.01% of our user base has a vulnerability, a bunch of websites write breathless articles that get clicks saying “122,000 WordPress Sites Vulnerable!”

That, by the way, I think we’ll be able to fix in the next 18 months with AI. The plugin security only works on Cloudflare.

Critical Feedback

As I said, we had a call with Cloudflare on March 23rd, where they asked for feedback on this thing they built but didn’t tell us the name, said it would probably launch in their developer week towards the end of April, and some top colleagues and I offered to help. I wish I could say the things I’m saying in this blog post on that call, and if they had just shared the announcement post I could have, but in the spirit of open source here’s what I would have said:

  1. If they had said the name I would have asked if they had any other options because I have an amazing colleague named Emdash who is doing some of the most exciting stuff with WordPress and AI. (BTW I think our Em will have more impact on the web than this in five years.)
  2. I actually think the product is very solid, there’s some excellent engineering, migration tools, it’s very fast, and the Astro integration is nice.
  3. I’d be surprised if this doesn’t get tens of thousands of sites on it.
  4. The UI is in the uncanny valley of being sorta-WordPress sorta-not. I know it wasn’t a weekend vibecode project, but it has some of that smell. Stuff breaks at the edges.
  5. I think using TinyMCE is a regression, and they should adopt Gutenberg, which we licensed and created to be used by other CMSes. (Correction: They use Portable Text not TinyMCE, but same UI criticism applies.)
  6. The Skills are amazing, a brilliant strategy, and we need to do the same as soon as possible. I’ve been working on something similar and got some good ideas from their implementation.
  7. I’m not going to say which parts, but they copied a lot of things we’re planning to kill. Build from first principles. Make it better. Skate to where the puck is going.

There’s a new CMS every other day. And that’s great! I love building CMSes and I totally get why other people do, too.

In Conclusion

Some day, there may be a spiritual successor to WordPress that is even more open. When that happens, I hope we learn from it and grow together. [removed “out of your mouth” sentence, too spicy for Western palates.] I’ve mostly focused on this post on just the software, but WordPress is also so much about the community — the meetups, the WordCamps, the art, the college programs, the tattoos, the books… The closest thing I’ve seen to a spiritual successor isn’t another CMS, it’s been OpenClaw.

Thanks to colleague Batuhan İçöz for helping review this.

Taxonomist

AI, WordPress

I’m really excited to introduce a project I worked on with various AI agents the other night, which I think represents a new way we might build things in the future.

First, the problem: My WordPress site has 5,600+ posts going back decades, and I had some categories that were old and I didn’t really use anymore, and I wasn’t happy with the structure. Every time I made a new post, it irked me a little, and I had this long-standing itch to go back and clean up all my categories, but I knew it was going to be a slog.

Let me present Taxonomist, a new open-source tool you can run with one copy-and-paste command line that solves this problem. Here’s the idea:

  1. You run this code in your terminal, and it spins up a Claude Code instance that asks you for your URL.
  2. Then it takes that and figures out what type of site you have, which APIs are available, and starts downloading all your posts locally for analysis.
  3. Sub-agents analyze every post against your current categories and thinks about suggesting new ones.
  4. It previews all the changes.
  5. Tries a variety of ways to authenticate against your site and make all the changes.
  6. Logs everything locally, so anything is reversible later.

THIS IS VERY ALPHA. PROBABLY BUGGY. BE CAREFUL WITH IT. PATCHES WELCOME. MAYBE MAKE A BACKUP OF YOUR SITE BEFORE YOU CHANGE IT.

It kind of just worked. I ran it live against ma.tt and it cleaned up a ton of stuff pretty much exactly how I wanted. But there’s a lot of weird stuff happening here, so I don’t know quite what this is yet.

  1. It’s very non-deterministic! There is some pre-written code, and probably could be more, but a lot of the code is generated on the fly by your agent. This creates interesting bugs where people testing with less powerful models had some odd behavior.
  2. I kind of want a directory of these useful AI agents on WordPress.org, but also, there’s something a little strange about trusting a remote shell script to run on your machine.
  3. I tested this with Claude, but there’s no reason Codex couldn’t use the repo in the exact same way, and I’d love to improve the quick start script to start by detecting all the agents you have, asking which you’d like to use, and also which directory you’d like to work in. I think we could kill the cd taxonomist-main && claude "start" part of it.
  4. Because much of the code and commands are generated on the fly from prompts, it’s very resilient! I’ve seen people try it, and it ran into errors with libraries or whatever, but it just figured out how to work around them.
  5. I’d love it if, at the end of every session, there was a moment for self-reflection where the agent would take the repository and suggest upstream issues and PRs based on anything that went wrong. Then this could recursively self-improve very quickly.
  6. There are some obvious improvements to this, for example, doing this for tags. Sometimes it creates too many categories when you might only want 3-5 for your theme.
  7. One fun thing is a bunch of the work of this just uses public WordPress APIs, so you can run it against any site! I like using distributed.blog as a demo. It’ll still do all the fun downloading and analysis and everything, you just won’t be able to make changes.
  8. I now have a local cache of all my WordPress posts I can do other interesting things with, and that’s cool.
  9. The logging and reverting probably still has some bugs in it.
  10. You can riff with it along the way, so for example, it suggested I get rid of my Audrey category because it didn’t have enough posts, and I asked it to look at all the companies on Audrey.co website and categorize any posts that talk about them as Audrey, which created like 50 more.
  11. I want to check the GitHub repo for any updates before it starts, and maybe periodically, because it’s iterating and improving really fast.
  12. It’s not the default but the entire thing is way more pleasant if you run it with skip-permissions. So testing I usually run the one-liner, exit, resume with skip.
  13. You can see some of my prompt history in the Github but I apologize it’s not comprehensive, I also used Gemini and Codex with this and got lots of value from them.

So, not sure what this is, but please check it out, play with it, submit improvements or ideas, and think about what’s next. Might host a Zoom or something to brainstorm.

The final thing I say is that this was a very different process of writing software for me. Instead of staying at the computer the entire time, I found myself going away for a bit, napping and dreaming about the code, coming back with new ideas and riffing on them. Maybe I’ll return to my Uberman polyphasic sleep days? Nap-driven development?

BTW I have lots of thoughts and feedback for Emdash but I thought this was more interesting, will try to get that out later tonight. One preview: TinyMCE is a regression; they should use Gutenberg! We designed it for other CMSes and would be fun to have some common ground to jam on.

Community Antibodies

AI, Audrey, Design, Friends, Health, Music, WordPress

First, I want to say how great the jazz scene is in New York. I caught a little Latin at my go-to Guantanamera last night, but the band seemed to be phoning it in a bit, so I walked over to Dizzy’s and heard an amazing big band performance by the Diva all-women Jass Orchestra, they had Clint Holmes leading vocals and I got Frank Sinatra / Count Basie vibes, so great to see such a tight big band.

In WordPress, last week it was fun to see the company some call parasitic WP Engine acquire WPackagist. So a popular way to use WordPress with Composer, previously maintained by an awesome co-op agency in London, was now in the clutches of a company using its capital advantage to try to openwash its alleged bad behavior, probably in a process that wasn’t ideal for the sellers.

Four days later, an awesome independent organization roots.io released WP Composer (renamed to WP Packages, in OpenClaw fashion) with 17x faster cold resolves than WPackagist. Check out their comparison page.

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It’s beautiful to see how resilient and nimble the antibodies in the WordPress community are. Major hat tip to Ben Word.

In another type of antibody, Sid Sijbrandi, whom I previously talked about going into founder mode on his cancer, gave an incredible presentation at the Open AI Forum about how he ran a bunch of N-of-1 experiments and therapies to cure his terminal osteosarcoma. He’s also open-sourced 25TB of his data for cancer research. Incredible!

If you want to see the future of health care, give Sid’s presentation a watch.

Song Creation

Design, Music, Personal, Travel, Video, WordPress

I’m in New Orleans for the first time in 7 years for a beautiful wedding. My Mom’s side of the family emigrated here in the 1860s, and there’s a deep comfort in the art, traditions, and weirdness of Creole culture. Good music and food are ubiquitous.

I met up with WordPresser Blake Bertuccelli-Booth to catch a set by Jason Marsalis at Snug Harbor, featuring some great originals and surprising arrangements of Maroon 5’s “This Love” and the music from the Bejeweled Butterflies game. Great artists find inspiration everywhere.

Afterward, we went to see my friend Troy, aka Trombone Shorty, at his studio. (Troy and I met when we both received the Heinz Award in 2016.) He was with Silkk the Shocker and Reggie Nicholas Jr., working on beats and songs. Though I was there for just a short while, it was inspiring to see the act of musical creation.

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A few days ago, Ed Sheeran went on the new Benny Blanco / Lil Dicky / Kristin Podcast Friends Keep Secrets. I haven’t watched the entire episode, but the twenty minutes from about 1:09 to the end where Ed and Benny come up with a new song I’ve seen 4 times now, it’s magical. Check it out, it’s one of the coolest things you’ll see this week.

I’ve seen Ed Sheeran loop his songs live, but this act of creation is very special, and I love the dynamic between him and Benny. It reminds me of that magical moment in Peter Jackson’s Get Back documentary where you see Paul McCartney and the band come up with the idea for the classic song Get Back.

Selling Your Company

Essays, Review, WordPress

I would like to offer some free business advice to people who are considering selling something they’ve created.

First, if the buyer insists you don’t talk to any other bidders, you are being screwed. They only do this because they don’t want you to find the market-clearing price.

Do you think when Microsoft called LinkedIn and said, “We want to buy you for $26B,” they just replied, “Sure! That sounds good.”

If you’re very lucky, you get to work with a bank like Qatalyst, which says, “That’s a lovely offer, let’s see who else would be interested.”

Ask yourself why someone wants to buy you? Who else might have the same motivations? That begins a process in which a wide array of parties review the deal.

If you don’t have the connections or a bank to help you, just email the CEOs of other companies that might be interested. Say: “XYZ wants to buy me for $Y dollars. Is that something you’d also be interested in?”

Now you’re creating a market.

Remember that you’re doing this for the first time, and on the other side of the table, they’ve done dozens of deals.

It really pains me to see WordPress-adjacent companies get taken advantage of by sophisticated financial and corpdev players who strong-arm them into not shopping their deal.

A confident buyer doesn’t care if you talk to others because they know they can offer you the best deal, which usually combines money with what happens to the business after it’s sold. This is the magic of Berkshire Hathaway.

Warren Buffett doesn’t care if you talk to other bidders; in fact, he wants you to, so you see why he’s the better outcome for your business if you want to sell it.

It’s tempting to want to celebrate every time a creator sells something. Say it’s good for the community. But if they didn’t sell it through a fair process, it’s more likely they were taken advantage of, and that saddens me.

For public companies, failing to follow the process I describe above can constitute a breach of your fiduciary duty to shareholders and expose you to legal action. But there aren’t any such rules for private entities, which is why they get rolled over so often.

WordPress Everywhere

Automattic, Essays, Open Source, WordPress

As we announced and TechCrunch covered, my.wordpress.net has soft-launched.

What this means is you need to fundamentally shift how you think about WordPress.

From the beginning, WordPress has always been open source, giving you freedom, liberty, autonomy, and digital sovereignty. Open source is the most powerful idea of our generation.

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.

You can even use it to cross-publish apps to the web, desktop, and iOS, like Blocknotes did in 2023. You can get the latest Blocknotes at Blocknotes.org. One codebase, multiple platforms.

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.

At Automattic, for better and worse, unlike Google, we almost never shut things down. We obsess about maintaining or redirecting permalinks. We make it easy not just to get your data in, but take it out too. We build businesses that lower churn not by locking you in (Wix famously has no export) but by making it easy for you to leave. If you love somebody, set them free.

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.

Join the WordPress community. It’s fun! We have cookies that don’t track you. 😉

Bar Gyu x Wapuu

Automattic, Events, Gallery, Travel, WordPress


For the Japanese WordPress community, I have planted a special Wapuu at the coolest spot in Niseko, Bar Gyu, aka the refrigerator door bar. 

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Now on the handle you’ll find a special surprise. Anyone recognize which WordCamp it’s from?

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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.

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I can’t wait to play these in San Francisco, where I have a Shindo Laboratory vinyl setup. (Pics from visiting Shindo Labs in 2009.) Some more snaps from the town since I haven’t done much PhotoMatting in a while.

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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.

Five items:

WordPress, AI, plugins, future of software engineering

AI, Open Source, WordPress

Yesterday I was on the WP-Tonic podcast, and my colleague Adrian Laboş did a great summary of the key points, which I’ll share here:

AI security audit wave incoming: Expect AI tools to flood WordPress core and the 70,000+ plugin ecosystem with both improvements and newly discovered security vulnerabilities, requiring infrastructure to triage at scale.

Avoid vibe-coding compliance surfaces: For payments, fraud, and regulated commerce flows, prioritize battle-tested WooCommerce and vetted extensions over bespoke AI-generated code.

Reposition plugins around durable differentiation: If AI collapses “nice-to-have” features (e.g., basic image manipulation), shift value to workflow ownership, integrations, compliance, performance, and support.

Agencies gain leverage, not obsolescence: AI tools give motivated technical people 10-100x capability increases, meaning agencies can serve existing clients far better rather than being replaced by DIY site builders.

Sell outcomes, not hours, as an agency: Client expectations will compress delivery timelines; adapt pricing to value-based packaging and use AI internally to raise throughput and QA coverage.

Design for agentic usability: Strengthen APIs, WP-CLI, and machine-friendly interfaces so personal agents can safely operate WordPress tasks without brittle UI automation.

WordPress Playground enables AI verification: Spinning up fully containerized WordPress instances in 20-45 seconds inside browsers allows AI to test code across 20+ environments simultaneously, fundamentally changing plugin compatibility testing.

Benchmark AI outputs against WordPress-specific evals: Adopt WordPress block, plugin, and site-generation evaluations to catch “small file” failures (readme, headers, packaging) that break deployments.

Prioritize compatibility testing by real-world co-install patterns: Reduce factorial plugin-combination risk by sampling tests based on which plugins are commonly used together and automating those paths.

Plugin directory needs editorial curation: With submissions accelerating toward 100,000+ plugins, WordPress will introduce editorial spotlights on newer plugins with excellent code/design to balance discoverability with marketplace openness.

Improve plugin discoverability without freezing innovation: Curate “trusted” and “high quality” signals while preserving pathways for new entrants to earn distribution through measurable excellence.

Plan for uneven economic diffusion: Even with today’s models, enterprise adoption lags consumer usage; build internal enablement and governance now so teams can scale impact as tooling matures.

Learning to learn beats domain expertise: When advising students/parents, the most future-proof skills are curiosity-driven learning, command of language, and study of classics/philosophy/ethics rather than specific technical domains.

WordPress 7.0 promises AI integration: The upcoming release will feature “lots of fun AI stuff” and represents one of the most exciting technology years in Matt’s career since starting in the industry.

I had no idea that today Anthropic would release their security thing that does exactly what I said.

The best thing you’ll read about AI engineering today is Chris Lattner’s take on Claude’s C compiler implementation. To steal Techmeme’s headline: “Claude’s C Compiler shows AI elevates the role of human judgment and vision; it’s a milestone, but closely mirrors LLVM/GCC, and hard codes things to pass tests.” The entire post is important, but this paragraph is particuluarly profound:

As writing code is becoming easier, designing software becomes more important than ever. As custom software becomes cheaper to create, the real challenge becomes choosing the right problems and managing the resulting complexity. I also see big open questions about who is going to maintain all this software.

To bring this back to WordPress: While I was in another meeting today, Claude Code with Opus 4.6 completed a cleanroom implementation of the ACF plugin in about 45 minutes. It was about to go off and implement all the pro features, but I stopped it because it would be a tremendous waste of tokens. The entire point of open source is collaborating on a shared goal rather than reinventing the wheel every time.

We’ve seen a slow version of this play out over the past decade, where every single web host that offers WordPress also spun up some sort of proprietary website or ecommerce builder. Bless their hearts. None has caused Shopify any lost nights of sleep. With countless person-years of development and who knows how many tens or hundreds of millions of dollars spent, I think we can now safely say that all of these efforts have had at most a marginal impact on their businesses, while the benefits of WordPress have continued to compound.

The thought experiment of whether those same resources had been used to make WordPress better is left as an exercise for the reader.

It does mean that competition is fiercer. You have to differentiate yourself on performance, customer service, reliability, design—things that are hard, but that’s capitalism.

It’s really important that in the plugin directory, we figure out how to make it easier for people to collaborate and build things together, rather than make a thousand versions of the same thing.

Two interesting posts today, first is Nick Hamze, who ponders the case on his delightfully avant-garde site for how WordPress fits in when everything is coded up on a whim, Nobody Rips Out the Plumbing.

Separately, I was delighted to see that legendary investor Brad Feld has hooked up Claude Code to post to his WordPress site, which hammers in Nick’s point that when you can use these tools on top of existing infrastructure, you get a much stronger foundation than imagining everything from scratch.

One of the great WordPress blogs is Quote Investigator. In their investigation into the original source of “If I had more time, I would have written a shorter letter,” I came across this great variation from Woodrow Wilson on the amount of time he spent preparing speeches.

“That depends on the length of the speech,” answered the President. “If it is a ten-minute speech it takes me all of two weeks to prepare it; if it is a half-hour speech it takes me a week; if I can talk as long as I want to it requires no preparation at all. I am ready now.”

So true.

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Matt 4.2

Audrey, Birthday, WordPress

It’s that time of the year again for a new version release. Forty-two is a fun number, of course, famous from The Hitchhiker’s Guide to the Galaxy.

I’m in Miami, where I’m attending a conference by Richard Saul Wurman. I decided that it would be a great way to fill my brain on my birthday. Since New Year’s, I’ve been in warm climates and had lots of dips in the ocean. Had a small birthday dinner a few days ago and my friends surprised me with a beautiful “HappyBdayMattic” cake.

This last year was particularly challenging, especially at the beginning. However, it just kept getting better, and particularly WordCamp US in August was inspiring. The warmth and support of the WordPress community pulled me out of the funk I had been in. It was also when I kicked off the habit of daily blogging, which led to 2025 being the highest number of words (34.7k) I’ve posted since 2004! I traveled 209k miles, about a third lower than last year, spending longer stretches in 45 cities and 16 countries.

One of my biggest lessons of the year was learning how to ask for help. I’m usually the person others come to, and I carry a lot of responsibility on my shoulders from my friends and loved ones, and for the companies and communities I’m lucky enough to be part of. I’ve had some bad experiences asking for help in the past, as well. Now, how I see it is that it might not always work, but if you don’t ask for help, you also don’t give people the chance to step up. This year, the support of several friends got me through some really tough spots.

A joy of this year was seeing my godchildren grow up, close friends starting families, and the Audrey Scholars program. There’s a Walt Disney quote I just found out about that I love: “I do not make films primarily for children. I make them for the child in all of us, whether we be six or sixty.” Kids can’t help but remind you how important it is to maintain that childlike sense of curiosity.

A random new thing I’ve adopted this year is coconut water. I’ve been trying to hydrate with electrolytes, especially first thing in the morning, and it’s a great natural source of minerals.

My main goals this year are to keep up daily writing, post some of my archive photos, finally visit Rome and bring my family, swim more, and be the best leader for Automattic and the WordPress community through the incredible changes and opportunities of the AI era.

Even though I have several decades of history now, I find myself looking forward far more than back. Great words to live by I just learned from Jeffrey Katzenberg, apparently originally from Doug Ivester.

Never let your memories be greater than your dreams.

That said, it is a funny time to revisit my original version-number birthday post, 2.2, which is exactly 20 years old now.

I wish everyone a wonderful 2026!

All birthday posts: 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42.

Wolfram Automattica

Automattic, Podcast, WordPress
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It’s exciting to announce that Stephen Wolfram has joined as a special advisor to Automattic.

I promise this is not just because he is such an incredible blogger, using WordPress, natch.

If you don’t know about Stephen Wolfram, his about page is not a bad place to start, but far more interesting is his 2019 essay on Seeking the Productive Life, which includes a setup for hiking outdoors while typing on a laptop.

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.

Automattic has been blessed with amazing directors over the years. Currently, our board is Susan Decker, General Ann Dunwoody, Toni Schneider, and me.

Apple iWeb

Video, WordPress

The new X/Twitter algorithim is hard to predict, but I’ve had one go viral with over a million views now, a quote-tweet of a cool demo video of Apple’s website builder from 2009, with themes and blog support and everything. Interesting to compare its interface to Gutenberg and WordPress today.

For the video to play on the webpage, you have to visit in Safari.

The colors here have now gone blue for winter, and snow has started, thanks to the excellent Snow Fall plugin. I also wanted to congratulate Wealthfront on their IPO. Many on their team have been friends or advisors over the years, from David Fortunato responding to my email about their WordPress blog being on an old version when they launched, to the amazing Adam Nash who teaches CS 007 Personal Finance for Engineers at Stanford, and he now runs the awesome Daffy donor-advised tax fund startup. I was an early customer, and even on their homepage as a testimonial in 2011, Audrey Capital has been an investor since 2013 and if you sign up with this link we both get 5k extra managed for free.