Fair to say I was gobsmacked by the news late yesterday that Automattic's board had put their CEO, Matt Mullenweg, on paid leave. I've read lots of stuff about it, in news articles and in a Hacker News thread. And a lot of posts on Twitter by Matt, and the replies. #
It's a very unusual situation in my experience in tech. Matt was able to raise a lot of money for Automattic, so he has maintained a controlling interest in the company, even though it has raised hundreds of millions of dollars. I left my own startup, voluntarily, when I was a little older than Matt, and I didn't return. I never wanted to be the CEO of a tech company, and I expect that being the CEO wasn't really a good fit for Matt either. A CEO's job is very different from being a developer and idea guy which Matt clearly sees himself as. #
Something has got to give, either you're a good CEO and the product languishes, or you focus on the product, and the company is unmanaged. In the cause of WordPress, I'd say it suffered in both areas. When I saw a chart of Matt's direct reports, I immediately saw a problem -- it was very long, iirc 60 people? No one can manage and guide that many people. Most of those people probably never get to talk one-on-one with the boss. #
For me, even when I was CEO, I wanted to spend all day working on new software and working with five or six other devs doing the same. Digging back into the past with Frontier these last weeks has reminded me both how good that can be, and how utterly frustrating -- when the people you're working with don't understand the mission. It's not their fault, it's the visionary's job to explain it so they can understand, and that takes time. These days Claude is filling in for all that, and doing a fantastic but at times incredibly frustrating job trying to give me what I'm asking for, while not understanding what I'm asking for. But we move through those disconnects quickly now, compared to how it was a couple of weeks ago. We have the source of truth that we didn't have the last time around, in the 90s, we have the C source code of the kernel, the product we built in the 90s. And Claude is the easiest to manage, so far I only think I detect an ego, it never seems to resent me criticizing its work, sometimes in ALL CAPS with strong language. :-)#
My wish for WordPress, in all its forms and shapes, is that it broaden its focus. I want a WordPress Lite, I implemented it, and it's sitting here ready to do a good deed for all the parties concerned esp the web and web developers. Maybe someone there will now have the time and be empowered to build out the product line beyond the narrow focus it has now. It doesn't matter what percentage of the web is WordPress, if it isn't going anywhere. The web needs help, and right now WordPress is pretty much asleep in regard to what's going on now in the web. And it could do so much to help the web get back on its feet. It should be a public resource as much as a profit machine for a few companies.#
One thing that opened my eyes about what Matt and Automattic are, was his story about how he and Om got together. "All roads lead to Om." What a great line, and based on the story, so true. A lot of things clicked for me then. I remember what a phenomenon Matt was when he arrived in California about 25 years ago? Very good looking young man, polite, quiet and rumored to get Web 2.0 better than anyone. This kind of thing happens in tech, and if you know everyone as Om did, and was liked by everyone, you could manage to hit the ball out of the park, investment-wise, and he did. Click click click. I had the individual facts but had no idea how they were strung together. I played a similar role at times in Silicon Valley, on both sides, as a bright young dude who "gets it" and as the gray beard who recognized the charm of a young new face and helped create a big money reality around it. There is a lot of snake oil in tech, before and even more now, and this one has had a long run, 2.5 decades, but it needs a new direction, because the money people aren't buying the magic any longer. That's probably imho really what Matt's firing is all about. #
I actually have more to say about this, but I have to get back to my programming work. If you have a comment, here's a good place to post it. #
Last update: Thursday September 10, 2026; 1:26 PM EDT.
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