On November 5th at our Noho office the legendary John Borthwick (investor in Twitter, Tumblr, Buzzfeed, Digg, Venmo…) and I will have a conversation on the future of the Open Web and human-centered AI. Please join us!

If you like rabbit holes, a wonderful way to spend your Sunday is in the writing of Zach Holman, an early engineer at Github and Gitlab. All are good, but a particular favorite of mine is UTC is enough for everyone …right? You don’t need to code to appreciate that time is a construct, that … Continue reading Time Zones →

The Atlantic November issue is lovely, focused on the American Revolution. I particularly enjoyed: So pick up a copy as you pass through an airport or by a newstand. I consider it a very worthwhile subscription. It might be better to read in print or through Apple News+ as their website a bit broken for … Continue reading November Atlantic →

It’s a bit of Automattic lore, but although I founded the company in June 2005, CNET asked me to stay on for a few more months to finish out some projects, which I did. Our HR systems have me as the second employee, after Donncha O Caoimh (still at the company!) So today is my … Continue reading Automattic 20 & Counter-claims →

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, … Continue reading Under the Weather →

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 … Continue reading New Woo →

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.

Make no little plans. They have no magic to stir men’s blood and probably themselves will not be realized. Make big plans; aim high in hope and work, remembering that a noble, logical diagram once recorded will never die, but long after we are gone will be a living thing, asserting itself with ever-growing insistency. … Continue reading Make No Little Plans →

Since reading the Four Hour Workweek and Tim Ferriss I’ve been a bit of a bio-hacker, always trying weird and new stuff. Today was a new one! I did therapeutic plasma exchange (TPE), also known as plasmapheresis, which supposedly gives you all the benefits of parabiosis without, you know, needing to be a vampire or … Continue reading Albumin →

Howdy and bonjour! First, thank you so much, merci beaucoup,  for having me at your WordCamp. I love the spirit of local communities gathering and helping each other learn and grow together. I wasn’t planning to speak; I was just going to attend this WordCamp, but since the organizers have given me a bit of … Continue reading WordCamp Canada →

There are a few writers who I follow religiously, and one is Matt Levine of Bloomberg’s Money Stuff. For business and finance it’s one of the smartest and funniest things you can read. Yesterday, I think for the first time, he mentioned WordPress! In the context of his quote on this great X thread about … Continue reading On Money Stuff →

Some days, like this morning when I almost missed my flight to WordCamp Canada in Ottawa, I’m so overwhelmed with the maelstrom of ideas and sparks of creation that it feels like waves crashing against a dam. There are so many ways I can imagine new software, new products, new ways for the world to … Continue reading The Curse of the Muse →

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 … Continue reading D’Angelo & Diane →

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 … Continue reading Nanochat & MCP →

If you appreciate golf at all, the story of how Tiger Woods won the U.S. Open at Pebble Beach without knowing he was down to his last golf ball because of arcane rules is pretty interesting.

I’ve been trying to find time in my calendar to attend more WordCamps as I love meeting WordPressers all over the world. The stars aligned, and I’ll be swinging by WordCamp Canada next week. They’ve put together an amazing program, including open web pioneer and inventor Dave Winer, so I’m looking forward to checking out … Continue reading In Canada →

Sorry everybody, my @photomatt on Twitter has been hacked, I’m trying to regain account access, but it is not currently in my control.

I’d like to introduce you to Jeremy Kranz. With his career as an investor at Intel Capital, then GIC, which is the sovereign wealth fund of Singapore rumored to manage over $700B, to now running his own fund Sentinel Global, he has had a front-row seat to investments in industry changing companies such as ByteDance … Continue reading Jeremy Kranz and Sentinel →

I was reminded today of the profound marketing influence of Kathy Sierra, who was a pretty prolific blogger and speaker back in the day. I would summarize her thesis as such: Your best marketing and communication should talk about how you make your users awesome, not how you’re awesome. If you’d like to check out … Continue reading Kathy Sierra →

One of the cooler companies I’ve seen in a while is LumaField, which does industrial CT scanning, as they describe it. Industrial X-ray CT (Computed Tomography) works on the same basic principle as medical CT, taking hundreds of X-ray images from different angles to capture the internal and external structure of objects in three dimensions. … Continue reading Battery Scan →

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.

Beeper has a fun set of September updates, adding support for Google Voice, LinkedIn now runs on-device, typing indicators for Google Messages and Instagram, full Telegram custom emoji support, and more.

I have two interesting interviews to share with you today, the first is Lex Friedman interviewing Pavel Durov, the founder of Telegram. I started using and advocating for Telegram back in 2015, and Audrey Capital was part of their aborted fundraise in 2018. As a software craftsperson, I’ve always had tremendous respect for the team … Continue reading Telegram and Weird Al →

Tonight there was a lovely event at TinkerTendo by Ramen Frey and Karin Johnson of Good People Dinners, this one honoring David Gelles’ new book, Dirtbag Billionaire: How Yvon Chouinard Built Patagonia, Made a Fortune, and Gave It All Away. I’m a huge fan of Yvon Chouinard and really enjoyed his book Let My People … Continue reading Greenwashing →

One of the things I hate most on the internet, and part of the reason I started WordPress, was to fight linkrot. Ever since 1998, when Tim Berners-Lee wrote “Cool URIs Don’t Change,” I’ve been obsessed with content management and ensuring that links don’t break. (BTW, TBL, a pioneer of creating the World Wide Web, … Continue reading Linkrot →

It’s so exciting to see what the creative minds like Nick Hamze or Tammie Lister are doing with Automattic’s AI vibe coding tool, Telex. Tammie is doing a Blocktober, a block every day this month of October, you should follow along.

Sometimes the battle for open source and freedom can take on very prosaic and practical terms, but the wins can benefit everybody. To give an example: In Beeper we need more memory for showing notifications, because we support end-to-end encryption for networks like Signal, but Apple’s default was to only give 15 megabytes — barely … Continue reading Fight For Open →

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 … Continue reading What’s Your Time? →

I want to dedicate my blog post today to my dear friend and brother, Om Malik, whose birthday it is. Om is a multi-hyphenate, but at his core, he’s a writer, someone who looks at the world and parses it down for others, a seeker who appreciates the spark of creation before most others. Om … Continue reading Om 59 →