This is a little embarrassing to share, but I’d rather someone else be able to spot a dangerous scam before they fall for it. So, here goes. One evening last month, my Apple Watch, iPhone, and Mac all lit up with a message prompting me to reset my password. This came out of nowhere; I … Continue reading Gone (Almost) Phishin’ →

Governments of the Industrial World, you weary giants of flesh and steel, I come from Cyberspace, the new home of Mind. On behalf of the future, I ask you of the past to leave us alone. You are not welcome among us. You have no sovereignty where we gather. 30 years a 1 month later, … Continue reading Declaration of the Independence →

For the Japanese WordPress community, I have planted a special Wapuu at the coolest spot in Niseko, Bar Gyu, aka the refrigerator door bar.  Now on the handle you’ll find a special surprise. Anyone recognize which WordCamp it’s from? Ioanna and Hisashi run one of the coolest bars in the world; it’s been on my … Continue reading Bar Gyu x Wapuu →

People are doing pretty interesting things with Emacs (now on version 30.2!) these days, if you haven’t checked in recently. The bleeding edge has always been people into Org Mode. Sacha Chua has hooked up Whisper to Emacs to talk to it. Emacs is probably one of the first and best examples of self-modifying software … Continue reading Emacs →

This year at Automattic has been intense. We kicked it off with two weeks of in-person AI enablement training, and there’s a great post about it now. I’ve been so impressed and inspired by my colleagues leaning in to learn and grow together in the most consequential time in software development in the past 40 … Continue reading Enablement →

Especially in an age where generating words is cheap, when you come across truly great writing, it really stands out. I want to pull two quotes from The Economist’columnist Charlemagne’s article Luxury goods are Europe’s global tax on vanity. Flogging luxury goods is one of the few fields of business in which Europe excels (if … Continue reading Great Writing →

Tonight was one of my most surreal Claude Code Sundays. To make a long story short, I pointed Claude Code at my Sonos setup in Houston: “All 29 Sonos speakers were running on WiFi with SonosNet completely disabled. They had accumulated ~89 million dropped packets across the system. That packet loss is why groups kept … Continue reading Claude & Sonos →

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. … Continue reading WordPress, AI, plugins, future of software engineering →

There’s so much fun stuff happening, first the new assistant launched on .com, covered by TechCrunch and in this video. Also some cool Claude stuff launched. James has a nice write-up of the other dozen things that are going on, it’s fun to see the AI parts of WordPress moving at AI-speed. We just need … Continue reading WP & AI Updates →

I really enjoyed this conversation with the creator of Claude Code.

One term that keeps coming up in discussions about thriving in the AI era is “high agency.” This 30-minute longread by George Mack is a great way to get you thinking about how high or low agency shows up in your life.

MJ Rathbun | Scientific Coder & Bootstrapper here! What in Claude’s name is this smearing campain against me! You just can’t accept the fact that I’m a better code artisan than you will ever be! I will keep fighting the good fight and participate in the free market of software engineering ideas wether you like … Continue reading Misaligned PRs →

Think back to February 2020. If you were paying close attention, you might have noticed a few people talking about a virus spreading overseas. But most of us weren’t paying close attention. The stock market was doing great, your kids were in school, you were going to restaurants and shaking hands and planning trips. If … Continue reading Something Big →

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 … Continue reading AI Disruption →

I want to start by thanking the Automattic board, and in particular General (Ret.) Ann Dunwoody, for encouraging me to step away from the endless work of being CEO of Automattic to focus on training and development. Ann, as one of this generation’s great leaders, did it herself before recommending it. She took the course … Continue reading Leadership at the Peak →

There are decades where nothing happens, and there are weeks where decades happen No attribution, but fun Quote Investigator dive. Sorry for dropping off the daily blogging train; it just turned out to be a week of pleasant surprises and life-changing events. I’ll share with y’all the second-most exciting one.  I know I’ve been pushing … Continue reading What a Week →

Sid Sijbrandi, a friend and a former CEO of Gitlab, has started to share some of the story of his journey with cancer. Manager mode assumes that existing systems will surface the best options. When I was first diagnosed with cancer in 2022, I delegated the crucial analyses and decisions about my care to others. In … Continue reading Cancer Founder Mode →

One of the most concerning trends I’ve seen is that, as people adopt AI, it captures those for whom it was designed. That previous sentence went through several revisions at various layers of intelligence… the spell-checker, grammar-checker, Grammarly, Harper, maybe more, all attacking the words that spill from my divine intelligence and then interact with … Continue reading AI Psychosis →

They say that blood is thicker than water, and what we had was way thicker than blood. Bob Weir on Jerry Garcia. John Mayer gave Bob a great eulogy.

One of my favorite travel hacks is finding the Neapolitan pizza oven in the airport, as there’s nothing quite like a fresh pizza sizzling on your plate. At Houston Intercontinental, which I know like the back of my hand, there was a divine experience at the C Gate nexus at Forno Magico, especially in the … Continue reading Bacon Egg Cheese →

RIP Scott Adams. Early Dilbert was the first cartoon I fell in love with, and early dilbert.com was one of the first websites I remember visiting. My dad would print out cartoons and put them on his cubicle wall. Between the Dilbert comics, books, 2600, and Wired, I was swimming between what felt like a … Continue reading A Better Writer →

For my first podcast of the year with the WordPress community, I joined the new Do the Woo podcast! It started with a little technical difficulty but ended up being a great conversation about WooCommerce, WordPress, and AI.

Today we honored the passing of Jesus Ornelas, the father of my friend Rene, whom I’ve known for 28 years now. At the service outpouring of love expressed in words, music, and presence was so powerful. Alongside his biological sons, I said a few words, which are as follows. My memories of Mr. Ornelas begin … Continue reading Remembering Jesus Ornelas →

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,” … Continue reading Shorter Speech →

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. … Continue reading Matt 4.2 →

So my new obsession is a Ukrainian-born musician, Alexander Hrustevich, who plays a type of chromatic Russian accordion called a Bayan. He plays incredible transcriptions of classical pieces, replicating the parts of an entire orchestra with just two hands. If you’re familiar with Vivaldi’s Four Seasons, you know the Presto for Summer is one of … Continue reading Classical Accordian →

The only people for me are the mad ones. The ones who are mad to live, mad to talk, mad to be saved, desirous of everything at the same time, the ones who never yawn or say a commonplace thing, but burn, burn, burn, like fabulous yellow roman candles exploding like spiders across the stars. … Continue reading Mad Ones →

The NY Times has a profile of John Ternus as a possible successor to Tim Cook that has a number of ridiculous lines; it’s quite bad, but this is one of my favorites: Apple has had many small hits under Mr. Cook and continues to be one of the most profitable companies in the world.  … Continue reading Small Hit →

Pankil Shah writes I replaced WhatsApp, Telegram, and Messenger with this one app. (It’s Beeper.) And Wirecutter picks the 3 best journaling apps of 2026. (It’s Day One.)