2026-02-12 06:34:07
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 someone told you they were stockpiling toilet paper you would have thought they’d been spending too much time on a weird corner of the internet. Then, over the course of about three weeks, the entire world changed. Your office closed, your kids came home, and life rearranged itself into something you wouldn’t have believed if you’d described it to yourself a month earlier.
Matt Shumer has written the post about this AI inflection point I wanted to write and send to friends, so I’m just gonna link to his and suggest that you read it. Hat tip: Toni.
The only thing I’d add is that there will be more demand for some of these things being automated, and tremendous consumer surplus created, so I think my view is a bit rosier than the tone this leaves you with.
2026-02-11 08:36:03
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.
2026-02-10 15:06:42
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 shortly after becoming a four-star.
The course was Leadership at the Peak from the Center for Creative Leadership, a nonprofit founded in 1970 by the family that invented Vicks VapoRub.
As I reflect on all the corporate training I’ve had, from the first class they made me take at CNET 22 years ago because my title had manager in it, to the workshops or intensive CEO things I’ve been lucky enough to be exposed to later, there’s one thing that really stands clear: You get out of any program what you put into it.
If you come in skeptical, distracted, or resentful, even if golden information is being dropped, it will bounce off you like water on a duck. You have to put yourself in a state of mind of extreme openness and enthusiasm, and take an earnest try at what the facilitators have designed and planned, no matter how cheesy, corny, obvious, or silly it might seem. Remember, their intention is for you to get something out of this, and they’ve done it before.
Holding that state of openness is also a catalyst for the teacher; they light up when students are willing to trust the process, and they’ll give you their very best. I originally titled this post “Complete Surrender” because that extreme statement helps me step out of the part of my mind that is always trying to challenge authority, remix conventions, or think I’m cleverer than others.
These programs are usually expensive, not just in dollars but in time you have to clear from other commitments, so don’t squander it by staying in your default modes of checking work, news, etc. Create a space for yourself to reflect, learn, and grow. It’s rare and precious.
The caveat, of course, is to choose your teachers well. CCL has been doing this since the 70s; they’ve figured a few things out. They’re Lindy. All of these programs change and evolve over time; they’re not carved in stone, but it’s particularly interesting to see what survives when something has been going on for a long time.
I’m also not religious about these things. I think of them as mental models that are new arrows in your quiver. You can use them as is, or, even better, mix them with something else you’ve learned to create something more useful and personalized to your context. The more you have, the more sturdy your latticework of understanding is, and the more robust your information framework will be when you encounter something novel.
There’s also some luck in the group; a bad apple can throw off the week for everyone. My cohort had people from a variety of industries like healthcare, paper products, car rentals, and business process outsourcing from all around the world, including Egypt, Brazil, Saudi Arabia, and all across the US. It would have been easy for people to be guarded, but everyone really leaned in. I think we had so little network overlap that people felt more comfortable opening up. And, of course, it was endlessly fascinating to learn about the challenges across vastly different industries, as well as the universal commonalities that arise whenever you try to vector a group of humans towards a common goal.
One of the inspirations I drew from Ann’s book, A Higher Standard, was the extent to which the Army invests in training and development, sometimes sending people to programs for years before they move into a new role. They’re always thinking about the next generation.
A big theme for me in 2026 is learning: Last month at Automattic, we did our first two-week in-person AI Enablement intensive at our Noho Space, and the feedback was incredible. On the WordPress side, this year we’ll have thousands of college students enroll in our new WordPress Credits program to earn credits toward their degrees. The number of cities where WP meetups are held is on track to double; it’s clear people are hungry for opportunities to learn and grow.
People have been asking my takeaways from the course, and it’s been hard to summarize, but I came away with big lessons on how my comfortable and improvisational presentation style can come off as not having a solid plan or being prepared, the importance of exercise and nutrition to have the energy you need as a leader, and the importance of being on time and what that signals to others. Great feedback is a gift and a mirror, allowing you to see things you might miss about how you show up to others. In the course, we made plans, and since then, I’ve been experimenting with integrating these learnings and others into my day-to-day. I feel like it’s really had an impact.
So in closing, when you’re a busy executive, there’s never a good time to step away for a week, but I highly encourage every leader to at least once a year invest in themselves and let your colleagues and loved ones know that for a few days you’ll be really focused on a departure from your quotidian day-to-day and work on growth. It’s hard but worth it.
2026-01-27 16:53:16
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 you all to learn the AI coding stuff as deeply as possible, and I have been doing some myself, my favorite a few years ago, a script to count when we had too many words in a presentation slide, but I knew Claude Code was something different and better.
However, I fell into the trap of bookmarking and downloading tens of hours of Claude Code tutorials and not installing the thing itself. And work has been busy! My colleague Dave Martin was hosting an internal livestream. I joined late, then had to leave because an important call came in. I decided to forget it all, throwing caution to the wind, and just install Claude Code and play with it without reading anything.
The next 24-36 hours are a bit of a blur. I haven’t locked into a multi-day coding session fueled by energy drinks, sugar, and cheesy carbs since my early 20s! There were some interruptions for previous commitments, but I basically became addicted to the feeling of that steep learning curve. Every minor annoyance or workflow became an opportunity to create new software in languages I’d never touched before.
It also really rewired my brain, even in how I talk. (Found myself saying “thinking” after a colleague’s question. 
) I’m thinking about problems in a much more structured manner now, how to divide and chunk tasks, and provide appropriate context and skills. I really do feel like my brain is being terraformed a bit.
So far I’ve written scripts or apps for grabbing daily summaries from my calendar, spinning up new projects and syncing them with Github, switching between Brave tabs better, an app to search and launch Brave tabs quickly…
Did you know that macOS Preview regressed and no longer lets you export a single page of a PDF as an image? I have an app that does that. What do I do with it? Do I open source it? Am I a Mac App developer now? Do I want to support this for other people forever? Should I even put it in source control? Or publish a set of tests and prompts, as Drew Brenig did with whenwords.
It’s a strange and wonderful time to be a lover of software and computers. A little bit of code goes a long way. I’m at a CCL leadership training this week so offline during the days and exhausted at night but I gotta keep all those little bots running.
2026-01-21 14:14:30
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 late 2024, when my cancer reappeared and my doctors told me I had exhausted the standard of care and there were no trials for my situation, I realized that assumption might, quite literally, kill me. Founder Mode was my only option.
Founder Mode meant going deep on every diagnostic and treatment option. It meant assembling a team of physicians and scientists to work from first principles to understand what was possible beyond standard protocols. Together, we paved new roads to access the very cutting edge of science and technology. Today, thanks to the efforts of many people around the world and the support of my wife Karen, I currently have no evidence of disease.
Sid was already very inspiring before this journey, and this is especially impressive. Elliot Hershberg has the full story and analysis, including some predictions for the future of cancer treatment.
2026-01-20 12:26:33
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 yours.
Anthropic has published a really interesting essay and paper, The assistant axis: situating and stabilizing the character of large language models. You need infoguards to protect your mind.
Sam Altman was prescient in 2023 when he said,
i expect ai to be capable of superhuman persuasion well before it is superhuman at general intelligence, which may lead to some very strange outcomes
Some very smart and talented friends are going down rabbit holes that don’t have good ends. My world is small; when you extrapolate this out to the 800M+ MAUs of ChatGPT, there’s probably a lot of weird stuff happening out there. We live in the most interesting times.
