I don’t get sick very often, but when it catches up to me it hits like a freight train. Just trying to keep all the plates spinning while operating at 10% capacity, been sleeping a ton. Today was in some ways better, some ways worse than yesterday. I try to avoid hospitals and emergency care, as you wind up in their system, so I’m trying to ride this one out at home. Had to cancel a bunch of travel and conferences and meetings I was looking forward to this week. Really makes you appreciate and be grateful for good health — it’s a baseline for everything else and I’m blessed with it 99% of the time.
Category Archives: Asides
WooCommerce 10.3 is out, just in time for Black Friday / Cyber Monday, with some nice improvements to the checkout experience, tracking cost of goods sold, and a new beta MCP server, “This new feature enables AI assistants like Claude, Cursor, VS Code, or any other MCP-compatible client to interact directly with WooCommerce stores through a standardized protocol, opening up new possibilities for AI-assisted store management and development workflows.” You can also help out in testing WordPress 6.9, which comes out on December 2nd.
If I’m slow on anything right now, I apologize. I’ve got some flu/Covid thing, so I’m operating at reduced capacity.
To Cut A Pineapple
Google has turned 25, which is wow, and they made a cute video about it:
Of course I tried to visit the original howtocutapineapple.com site, and unfortunately saw a database error connection. From Archive.org it looks like whoever had that domain made a nice WordPress site.
I have some “grand theories” of software engineering: I think there are two tribes of engineers that complexify things or simplify things, and they are in eternal conflict.
Complexify: Jamstack, headless, Contentstack, Contentful, DXP, DAM, micro-services.
Simplify: WordPress, Simplenote, Day One, djbdns, SQLite.
Not enough engineers have studied under the code of Daniel J. Bernstein.
Just last night I was re-watching Annie Hall to remember and honor Diane Keaton, and now the news that D’Angelo had passed. I’m writing this listening to Voodoo, one of the great albums of all time. That CD in my beater car in Houston was on constant rotation, the richness of the tracks— it’s an album you have to listen to in its entirety, it takes you on a journey, the way the tracks blend in to each other. Not ideal for the atomized world of songs being stand-alone.
D’Angelo was obviously a star, but one amazing thing about his bands is he brought so many people with him, so many amazing jazz musicians, including Roy Hargrove, Robert Glasper (HSPVA!), Chris Dave (HSPVA!), Kenny Garrett, Pino Palladino, Questlove… May his memory be a blessing.
Probably the most interesting thing on the internet today is Andrej Karpathy’s nanochat, “a minimal, from scratch, full-stack training/inference pipeline of a simple ChatGPT clone in a single, dependency-minimal codebase.” 8,000 lines of beautiful code, as Simon Willison notes. If you want to understand how LLMs work, study this. Andrej is a code poet.
In hacking news, Wired has an amazing article on intercepting geostationary satellite signals.
On Friday, we turned on something cool: every WordPress.com site now supports MCP. Right now this is read-only access to your site, because the S in MCP stands for Security, but you can already start to do some cool stuff with it.
Sorry everybody, my @photomatt on Twitter has been hacked, I’m trying to regain account access, but it is not currently in my control. Update: Thank you to the fine teams at X/Twitter and Nikita Bier, my account has been recovered. Just for future reference, I will never promote cryptocurrencies or similar investments. If you see anything from me or WordPress claiming that, be highly skeptical. Invest in open source, public stocks, and great companies like Automattic. 🙂
Tim & Pablos
Two of my favorite humans, Tim Ferriss and Pablos Holman, had a great interview together.
Pablos has a great new book out, and Audrey Capital is a happy LP in his Deep Future fund. Of my many hacker friends, Pablos is probably the most public.
I think some of the best writing about technology PR is this ten-year-old article by Aaron Zamost: What’s Your Hour in ‘Silicon Valley Time’? It describes the cycles that companies go through in public perception, and the beauty of revisiting it ten years later is that you can see which of the examples are still relevant, or the domains that 404. As someone who has been around this clock probably a dozen times now, I highly suggest this for anyone “going through it.” Some of the most powerful words in the English language: This too shall pass.
See also: The Zen fable or old Chinese poem of the old man who loses his horse.
Saturday Shares
A few links for you:
- From Kirschblütenboogie to Khruangbin (from Houston!), here’s a Saturday chill Spotify playlist I made for you to have good vibes this weekend. Perfect for sunsets. Hat tip: Daniel Gruneberg who first introduced me to Hermanos Gutiérrez.
- Open Infrastructure is Not Free: A Joint Statement on Sustainable Stewardship. “Billion-dollar ecosystems cannot stand on foundations built of goodwill and unpaid weekends.”
- Chat-based photo editing is one of the most magical uses of AI right now, and Google Photos just made it available to everybody.
- Did you know Automattic has an anti-glossary?
- It’s cool to see Vitalik Buterin come around to copyleft licenses.
- I’m going to re-link the Grit interview, some people are saying it is their favorite they’ve seen of me in years.
- BCG has an annoyingly-good rundown of The Art of Capital Allocation.
- The Linux Foundation thinks open source contributes $9 Trillion in global value. Really what we’re doing is sharing the technological phylogenetic branches for humanity’s progress.
- A great interview with Petter Törnberg on his paper about how social media might be structually dysfunctional. “Rather than bringing us together into one utopian public square and fostering a healthy exchange of ideas, these platforms too often create filter bubbles or echo chambers.”
- See Harry Mack meet Will Smith and Martin Lawrence.
Fun fact: this post has the ID of “150,000” in my wp_posts table.
Five Publications I’d Love on WordPress
When WordPress started in 2003, I never dreamed it would power over 40% of websites, nine times the number two CMS, but I wrote on a notecard a list of five publications I admired and respected so much I wanted them to run on WP someday. In the interest of sharing your dreams to help them come true, here they are:
And one bonus: Houston Chronicle. (Gotta root for the hometown.)
There has been uneven progress toward this over the years; we’ve gotten some of the NYT and all of the New Yorker at one point, only to have them revert under new CTOs. Also, there have been some unexpected huge wins, like when Vox Media retired its proprietary CMS Chorus and brought over amazing publications like The Verge and New York Magazine. For any projects related to these publications, including trials or micro-sites, I’d be happy to provide my feedback on architecture, design, and opportunities, and contribute Automattic and VIP resources wherever they could be helpful.
I believe the most crucial aspect to get right for these customers is real-time co-editing, which is on the Gutenberg roadmap and shipping soon. If I were writing this list today I might choose some different targets.
When my father passed unexpectedly, I was despondent. One thing I remember was the Amazon lovebomb I got from my high school girlfriend Sunaina Sondhi, five books to help me deal with the pain. Even a decade after we dated, books were her love language; in fact, she had given me my very first book about meditation when we were teenagers. I don’t recall what all the books were, but the two that really made a difference for me were Elisabeth Kübler-Ross’s and David Kessler’s posthumous book On Grief and Grieving, and the Tibetan Book of Living and Dying. Each allowed me to process and understand the emotions I was going through.
Every 6 Minutes
I’m at a dinner tonight and they have these old magazines on the table, including some old copies of WIRED, which, if you can imagine, as a kid in Houston in the 90s, was a portal to the amazing world of the internet and technology. I flipped through, and there is an entire web hosting classifieds section! Hiway Technologies wants you to know that every 6 minutes, someone hosts with Hiway.

Every six minutes, so they were doing 240 signups a day. 100,000 sites! Last month WordPress.com created a new site about every 3 seconds. Hiway was founded by Scott Adams, same name but not the Dilbert guy or the game designer, who apparently played football in Florida and the company “was sold in 1999 for $352 million. Adams was 35.”
There was also this guy, who has a website, but do you?

United Starlink
I’m on my first United flight with Starlink, and wow! I ran a fast.com test and got 110 mbps down and 38 mbps up, which is insane. 28ms ping times. While flying! When you think of all of the engineering and technology coming together to let me blog this it’s really incredible.
Update 2025-09-16: United actually responded to my tweet about this. 😂
Andrew Chen has a great post on retention.
Weekend YouTubes
One of my favorite YouTubers is Charles Cornell (WordPress-powered!), who creates great videos that break down the music theory of various things you’ve heard, such as this adorable one featuring SNES soundtracks or The Legend of Zelda: Breath of the Wild. I first came across him reacting to Jacob Collier in 2020. Once I got super-into Severance, his breakdown of the spooky music is great. It’s also interesting to see that the YouTube community is going through its own version of fair use and copyright, trademark, etc., enforcement, which he discusses here.
Sam Altman is always interesting to follow, and it’s interesting to contrast this great interview he did with David Perell on writing with this very direct and awkward one with Tucker Carlson. I have immense respect for anyone who enters the arena and engages directly with journalists or critics, rather than hiding behind PR agents or lawyers. Given the current blood feud, it’s fun to go back eight years and see Sam Altman interview Elon Musk, long before any of the AI stuff blew up they were both terribly prescient.
Ray Dalio is always a gem and he went on Diary of a CEO. Theo Browne has a good take on what it means to vibe code. Kishan Bagaria discusses how Beeper is going to reach 100 million users. The story of how Atlassian took a non-traditional enterprise path with Jay Simons is great. Not a YouTube, but don’t miss Bret Taylor on The Verge. Check out Adam D’Angelo at South Park Commons.
And finally, I’ll say that YouTube Premium, which turns off all the ads, is probably one of the highest value subscriptions you can have. Many of these are essentially like podcasts, and from a product perspective, I think we need to figure out how to sync and allow seamless movement between watching, listening, or reading transcripts in Pocket Casts (Automattic’s open-source podcasting app). We support video podcasts, but there’s no good way yet to have a Whispersync-like experience between video, audio, and a transcript.
Old Business Cards
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:
- I went mostly by “Matthew” then.
- At some point I decided to remove the home address and say that I was available to play not just alto saxophone but baritone, tenor, and soprano as well.
- The number was the home shared house number, not a cell phone.
- The email was an email address the entire family shared, under my dad’s name.
- HAL-PC was an amazing non-profit local to Houston that stood for the “Houston Area League of PC users.” There was a pretty reasonable annual membership fee, and they hosted a monthly general meeting which had hundreds of attendees, always with a presentation or two and a raffle giveaway at the end. They were a dial-up ISP and BBS/newsgroup host. I volunteered for them by going in on Saturdays where they had a room people could bring their broken computers to and get free tech support, and by hosting a SIG, or special-interest group, around PalmOS called HPUG, the Houston Palm Users Group. This was a big part of the inspiration for WordCamps.
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:

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 about.
As it happens, James LePage of Automattic has spun up a WordPress plugin for it, so that was fast. Now the thing to figure out is distribution and adoption.
PostHog
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 that is both fun and playful. They even have their own version of pineapple on pizza.

What I want to enable with WordPress is the ability with thousands of plugins and themes for people to have unique, funky experiences like this on their website, while still providing a content structure that’s legible for interoperability and hacking. Major kudos to Cory Watilo and James Hawkins for coming up with this.