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.)

The best part about blogging is the comments, and after I posted “I wish that when you use Find My to find your iPhone, it would also flash the flashlight, which would be great for finding it in a bag or a dark room.” Michael Wender and David Artiss jumped in that it’s already there! … Continue reading Find My Update →

I wish that when you use Find My to find your iPhone, it would also flash the flashlight, which would be great for finding it in a bag or a dark room. 

Anything that annoys you is teaching you patience. Anyone who abandons you is teaching you how to stand up onyour own two feet. Anything that angers you is teaching you forgiveness and compassion. Anything that has power over you is teaching you how to take your power back. Anything you hate is teaching you unconditional … Continue reading Jackson Kiddard →

They’re both long reads, but worthwhile.

I rang in the new year with an unexpected trip to St. Barts that ended up with friends. I made a resolution in 2025 to watch more films. It’s an art form I have many friends in and when we have hung out I realized how shallow my understanding of the canon of film was. … Continue reading Happy New Year →

The writer Aadil Pickle has a great profile of one of my favorite hackers, “Training the Idea Muscle” on Riley Walz. Riley epitomizes the term “high agency,” and I’ve been continually impressed with his ability to rapidly code novel ideas and interfaces on top of public or reverse-engineered data. He’s a hacker, artist, and provocateur. … Continue reading Riley Watz →

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 … Continue reading Wolfram Automattica →

If you haven’t seen it, The Thinking Game documentary is excellent, and available for free on YouTube. You have to buy it, but the Kanye documentary In Whose Name is also pretty fascinating. (I first blogged about Kanye in 2007, discussing PHP’s botched version 4 to 5 upgrade.)

One of Carl Jung’s famous quotes is to “Beware unearned wisdom.” Sometimes it’s brought up in the context of psychedelics. From LSD and the Mind of the Universe by Christopher Bache: Psychedelics give us temporary access to realities beyond our pay grade, allowing us to experience things beyond our normal capacity. It’s all too easy … Continue reading Beware Unearned Wisdom →

Cloudflare released their Radar report for 2025, one fun stat was they analyzed the top 5,000 domains, and it had some interesting results for website technologies. Open Source tech came in at 47% for WordPress and 4.7% for Drupal, which wins the majority! Then in proprietary there was Adobe at 16%, Contentful at 8%, Shopify … Continue reading Cloudflare CMS Stats →

The Wall Street Journal has a fun article about the Nex Playground, The Hottest Toy of the Year Is Made by a Tech Startup You’ve Never Heard Of. I think this is the first time one of Audrey Capital’s companies (we invested when it was the Homecourt app) is the hot Christmas item. Here’s it … Continue reading Nex Playground →

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 … Continue reading Apple iWeb →

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 … Continue reading Winter Fun →

Tonight was a lot of threads connecting for me. At Automattic’s Noho Space we hosted an event for Martin Scorsese’s new documentary about Pope Francis, called Aldeas. There was a point in my life when I wanted to become a priest, and I had been inspired by meeting a Franciscan seminary student. I took it … Continue reading Aldeas →