WordPress, Taylor Swift, Super Bowl, oh my

There has been quite a bit of buzz in the WordPress community because during the Grammys red carpet Taylor Swift’s website went down and this is what everyone saw:

Hey there! That looks familiar. What a beautiful WordPress logo! (Hat tip: Alexa Scordato for telling me about this.) The website also had some ups and downs, we haven’t been able to get in touch with anyone on Taylor’s tech team, but if you’re there, we’re standing by and happy to spin up your site on wp.cloud so it can handle any amount of traffic.

This gets even more interesting, because for the first time in my life, after having orbited around the Super Bowl for decades*, I am attending in person. Thanks to the graciousness of my friend and advisor Jason Hoffman, I’ll be in an owner’s suite, wearing a WordPress t-shirt, possibly not too far from Taylor, watching the game. Look for me on TV! I know she loves Tumblr so I’ll have with me a little gift bag of Tumblr swag just in case I meet her.

* How have I been orbiting around the Super Bowl? Even though I don’t follow sports, I’m obsessed with the Super Bowl, and typically host watch parties every year. I love seeing the pinnacle of American achievement. The Super Bowl centers around a number of interesting stories in my life, such as when I was in high school and very poor the Super Bowl was in Houston, and they made McNuggets really cheap, so I ate 104 McNuggets in one sitting. (Sweet and sour sauce, natch.) At that infamous Justin Timberlake / Janet Jackson moment, they needed extras on the field to be their audience and my high school girlfriend was one of the kids in the audience when it happened. There’s so many more stories I could tell!

Thoughts on Tech Employment

The Washington Post writes The U.S. economy is booming. So why are tech companies laying off workers? This article has some good data, but I think misses the point with sub-heads like “Shine has come off the tech industry.” Really? How is that reflected in their stock prices?

I think a few things are happening.

First, tech companies are typically best at adopting new technology, which leads to productivity gains.

AI may be an obvious example of this, though for all its hype it hasn’t had a huge impact on most companies yet. I agree with Sam Altman when he says there may someday be a billion-dollar company run by one person who is able to highly leverage future AI agents to automate most traditional roles at a company. That said, I think there are advantages to teams including allowing people to go on vacation or take time off, and provide business continuity and succession, so literally one-person is probably an exaggeration. We don’t need AI to see very small teams being valued highly: Instagram had only 13 employees when it sold for a billion dollars to Facebook, in 2012!

Some of this productivity gains just come from adoption of existing tools like Google Workspace or Office 365, issue trackers and version control with tools like Gitlab, Github, or Jira. At Automattic we don’t use email to work or communicate internally, it’s all Slack and P2. We also leverage our distributed nature to effectively have teams around the world coordinating several shifts of product work per day, and 24/7 coverage for things like systems and customer support without the need for “graveyard shifts.”

The way tech companies operate, the pace and culture, would be unrecognizable to people at many more traditional companies.

At tech companies some roles are highly leveraged, like systems, engineering, and design, and everything else in the company really exists to support these. These leveraged roles can create enormous amounts of value, and that’s why it’s not unusual to hear of machine learning engineers working on ads at Google with salaries in the seven figures. (There’s been a weird accounting thing where companies put a lot of their compensation into equity, but I think that’s going away as investors are learning to better account for dilution and employees appreciate the fungibility of cash.)

Creators are also highly leveraged, which is why Joe Rogan can sign a new $250M deal with Spotify (which smartly puts him back on Youtube) after laying off 1,500 people in December. Some people like Hagen Terschüren try to tie this together and say you should avoid Spotify for it, but there’s nothing wrong with a business becoming more efficient to serve its customers, it’s the whole point of capitalism. Capitalism is, as Nicholas Stern says (via Marc), the best way to take care of people we don’t know. There’s no honor in keeping people employed inefficiently, it’s better for them to find someplace in the market where their talents will be better leveraged for society and themselves.

There was a bubble in hiring because tech had so much money it tried to throw people at problems. But the unlock in technology can come from a single person, a single insight. It’s the mythical man-month. Tech-first companies are going to become leaner and more leveraged. Fewer people are going to create more value for society, in ways that will follow power laws and I think we should investigate things like Universal Basic Income to provide for all living beings. Technological progress creates abundance, where we have more than what we need.

At Automattic last year we did not do layoffs, but allowed performance management and natural attrition (voluntary regrettable was 2.9%, non-regrettable 6.8% for us in 2023) to allow our size to shrink down more naturally, on average two people left for every person we hired last year, from a peak of about 2,064 to 1,936 today.

It’s hard to pick a favorite tenor player, but the GOATs that come to mind are Dexter Gordon, Sonny Rollins, John Coltrane, Michael Brecker, and I’m missing people but if I had to pick someone to express the human condition and soul, it would be Joshua Redman. He has such incredible fluency with the horn you get an amazing emotional experience with his vibrations. He’s probably the greatest living tenor saxophonist. He just did a Tiny Desk concert, and the audio and visual capture was impeccable. I watched this full-screen on an Apple XDR and listened with Airpods Max—the chords they’re using, the subtlety of the interactions— the experience was exquisite. (Also peep HSPVA grad Paul Cornish!) I can’t embed because it’s not on Youtube yet.

What if this VR is training our brains to compute in a different way? How we perceive our thoughts to train the models. We are reconfiguring our model of reality to process things in a way we couldn’t before.

If I were President for a day, the first thing I would do is instruct our national security to patch and secure every American technology company, as they are our gems in the world. I would burn every zero-day I had on a US company and help them patch it. The rest of the world would know our immense defense budget was now being used to secure our companies as well, as China does. Apple, Meta, Google, Microsoft, Intel, Cisco, Arista, Unifi, Qualcomm… I’m probably missing a few, they should all have the shield of our national security defense. Right now each company has to create their own defenses, and they are getting eaten and pillaged by foreign companies with state backing.

When I read things like the iFixit Teardown of Vision Pro, I am moved almost to tears at the sheer beauty of craftsmanship in this thing. It is literally incredible. I have so much respect for the big tech companies like Apple that invest in long-term science, research, and development to create innovations like this. It is literally the engine driving our economy forward.

I just replied to an email from 2018. I am tragically, comically, behind on email. Because Automattic doesn’t use email, we use P2, it’s never been a priority for me. But I have been sloppy, careless, and derelict in my duty of answering emails. Apologies to you all. You’re going to get some weird, very late replies.

Vision Pro First Impressions

Okay… wow. The hardware and display are like nothing I’ve ever seen, really feels like it’s from the future. That said, I found the setup clunky and buggy. Some might have been user error, for example I kept trying to “select” things with my middle finger and thumb and not my left finger.

I almost got stuck in the Persona setup, couldn’t continue. I don’t love how my Persona looks. Looking and selecting stopped working and I could only continue by physically reaching out and hitting the buttons. (This must sound ridiculous to someone who hasn’t used a Vision Pro yet. I looked pretty silly!)

I got totally stuck at the part of the setup where it was importing iCloud apps from backup, and I was ready to give up. A friend put it on and was able to get past that step for me. Adding credit cards was a terrible UI, with the security code PIN pad in front of the interface.

I decided to call it a night, and try more tomorrow. Just like I learned to type I think I’m going to need to learn to become fluent in this new interaction paradigm. I did have a before and after feeling, like the world had shifted, not unlike when you saw the first iPod or iPhone. This post probably doesn’t make any sense to someone who hasn’t tried the Vision Pro, but hopefully the team sees it and can take this feedback.

Rowing to Alcatraz

My friend Neal Mueller, who holds a Guinness World Record for longest non-stop row in Arctic open water—1,000 miles over 41 days in 2012—gave me the incredible gift this morning of introducing me to the Dolphin Club in San Francisco, which has a rich lineage of these hand-built rowboats and love of the craft of rowing. It was awe-inspiring. He then rowed me to Alcatraz! We saw a rainbow (third from last photo in gallery)!

We captured some Spatial Video that will be fun to look at on the Vision Pro later (mine just arrived, but I haven’t opened it yet).

I think what I learned this morning is there is something deeply profound about the act of rowing, of being in harmony and synchronicity with others on your boat, how good it feels when you’re in sync, and how obvious it is when you aren’t. I’ve done rowing machines before many times but never been on the open water, and I saw also the impact of the variability of the ocean, currents, and waves had on the rowing. I think there is also something related here to when autistic people (and myself!) rock back and forth when something feels like it’s in alignment.

Luckily I was with literally one of the world’s best rowers, so I always felt safe and was able to enjoy the feeling of being on the water, and really felt the heritage and respect of these beautiful craft we were on, Cronin-1938. I introduced Neal to the concept of the Ship of Theseus, one Matias and I love to talk about in the context of Gutenberg. One of the most beautiful days I’ve seen in San Francisco. Here are a few photos from this morning.

My sabbatical is off to a great start. ☺️


Today is the day! The first day of my sabbatical. What an experience it has been. On Thursday I delivered my very first Ignite talk on the subject! Here it is.

The Ignite format is a tricky one as a speaker! I will do better next time. My friend Connie has delivered seven Ignite talks now and I thought hers and Adam Savage’s were the highlights of the ones I saw. (I didn’t see everything because I was popping in and out.)

Preparing for this sabbatical has been the most fun I’ve had working at Automattic, ever. It brought so much clarity to things, we’ve been able to resolve in hours things that have lingered for months, including two acquisitions, several hires, big strategies, and more.

After this talk I caught a redeye to NYC to meet with the WordPress.com leadership team and hand off my leadership there to Daniel Bachhuber.

It is a beautiful symmetry that the first-ever sabbatical taken at Automattic was by its CEO at the time, Toni Schneider, which gave me the opportunity to step in and try on being a CEO, and it’s an incredible gift that Toni is returning to be CEO of Automattic while I’m out for the months of February, March, and April.

What am I going to do with all this free time? Blog a ton. So follow along if you want to see this journey. I’m going to try to open source all the things. 😇

Update: I ended up extending this to May 15 since it got a late start.

Automattic’s Big Re-Org

Considering I am going on sabbatical in 83 hours and passing the CEO torch to Toni Schneider until I return in May, it seemed like a perfect time to do a giant re-org! Just kidding. But we did introduce a concept into Automattic that I think will provide a lot of clarity for the teams within Automattic, and hopefully for the broader WordPress ecosystem that works and partners with us.

The frame is there’s a game, each person gets a card: Be the Host, Help the Host, or Neutral.

You cannot change cards during the course of your day or week. If you do not feel aligned with your card, you need to change divisions within Automattic.

If you’re Be the Host, you are hyper-competitive. You are trying to make the case to a customer for why they should host with you and not consider anyone else. This is what everyone assumes all of Automattic is, but it’s actually just one sub-division, which is a minority of our revenue.

For Help the Hosts, your word is ecosystem. You plant the seeds of open source software that grow everywhere. Every WordPress is precious to you, wherever it grew up. You want every host to be as successful as possible, because the real threat is from the Big Proprietary folks outside, who steal all your good ideas and don’t let you touch them again. You want to get to know every WordPress in the world, however it grew up, and help it out by selling it attachments.

Neutral treats everyone equally, either because they don’t care (Day One, Pocket Casts, et cetera don’t have a horse in this race) or because they are a support function like finance or HR.

Whenever you meet or talk to an Automattician you can ask what their card is.

Also, WordPress.com is going to orient itself more towards developers, and have an experience that feels similar to WordPress hosted other places, less Calypso more wp-admin.

The big tension this surfaced was Woo Express, going forward that team is switching under WP.com, and Woo.com will recommend a variety of hosts (like W.org) to get started with Woo. Now people can meet with Paul Maiorana, who leads Woo, or James Grierson, who leads Jetpack, and know they have Help the Hosts cards as their teleological goal.

Freedom Grants

The Audrey Scholars program is still getting started, but I wanted to introduce another opportunity: Freedom grants. As the page says “If you are an open source contributor, and you feel your current political environment is incompatible with open source values, we would like to offer the opportunity for a grant to help you get set up in a new environment. Please state your case below.”

I’m not sure exactly how this will work, but we’ll figure it out together. The offer is out there. This is very much inspired by the work of the Oslo Freedom Forum.

New York!

You tear me apart. The greatest city in the world. (San Francisco has its allure.) I am so drawn to the impeccability excellence of uptown. Just at a baby shower at 111 West 57th… wow! You have never seen a better building, everything is executed to the highest degree par none.

Yet, I’m so drawn to downtown. The jazz. The creativity, the spark, the drive.

Automattic’s office at 166 Crosby feels like a creative center. We’ve built something pretty cool there to inspire and delight people in space.

Proprietary software is like creating art which no-one can see. Open Source elevates software engineering to a collaborative art form. Code is poetry.

— Tom Willmot

Some choice words from Tom Willmot, who was watching Kirby Fergusen’s Everything is a Remix, which I’ll check out now.