Sabbatical Wrap

Today is my first day post-sabbatical, getting back in the swing of things with Automattic., all the things. What a unique experience! I found the lead up to the sabbatical and planning process to be infinitely valuable, the sabbatical itself to be interesting experentially, and I’m curious to see what the post-sabbatical effects are. I have that nervous excitement like it’s the first day of school, which I haven’t felt in years. What should I wear? Who will sit with me at lunch?

I could now give a much better talk about the value of sabbaticals, having finally done one myself vs observing the hundreds that have taken place at Automattic. Like having a kid, it’s something you can understand intellectually but the direct experience is profound in ways that are hard to articulate.

There’s so much to catch up on and it’s kind of delightful to check in on progress of things after a few months rather than day-to-day like I normally do. If I had one bit of advice it would be to not get a big surgery (I had a sinus one) or plan for other major health things during a sabbatical, that should be on a different track if you can help it.

At the beginning I allowed myself two goals around sailing and chess. Sailing I decided to postpone to take advantage of a peak opportunity in July, but chess has been a fun incorporation into my daily habits and also incredibly humbling playing with folks who have been at it longer. The thing I didn’t plan for that became actually really important to me was getting back to the saxophone, not even trying to perform but the ritual and zen of long tones and practice is incredibly grounding in a way I didn’t know I was missing.

A few bullet point highlights:

  • Rowed to Alcatraz.
  • Got Covid the 4th time.
  • Went to Super Bowl.
  • Spent time at my alma mata University of Houston.
  • Toured the modern cathedrals of datacenters.
  • Did a ton of health scans, blood tests, doctor meetings.
  • Got my DEXA body fat down to 17.9%.
  • Skied Big Sky and Yellowstone Club.
  • Went to friend’s 40ths and 50ths.
  • Got a major sinus surgery.
  • Hosted an epic eclipse party from a plane with 100+ flash talks.
  • Studied Qigong and yoga.
  • Spent time in Houston, San Francisco, Big Sky, Austin, Orlando, Tokyo, Taipei, Amsterdam, Paris, and Mallorca.
  • Cleaned up a ton of personal projects.
  • Read a ton.
  • Swam in the ocean.
  • Played saxophone at 40k feet.
  • Equine therapy.
  • A lot of progress on renovation projects in Houston and San Francisco.
  • Hiked many places, walking in general more than normal.
  • Tweaked my back. :/
  • Couple of podcasts and interviews, a few meetings.
  • Binged Three Body Problem.
  • Did a lot of solo time and introspection.

Also, there was actually a lot of Automattic stuff happening most notably the acquisition of Beeper! I wasn’t able to unplug as much as I hoped, but I did definitely reverse my normal priorities. One thing I really missed was that I had very high hopes to see a lot of people, but a lot of stuff came up so outside of the events it was probably smaller social circle than I normally have.

It does make me think about apophatic theology or how Nassim Taleb talks about via negativa. Whatever you’ve been doing, it’s nice to try the opposite for a while, just to see what happens.

Karaoke Hacks

You can’t sing. I can’t sing. But we both should sing, from the depths of our bellies because it’s good for your soul. We don’t sing enough in modern society! Hence, my love of karaoke.

Live band karaoke is the best, which I’ve done everywhere from the basement of Hill Country BBQ in New York to someplace random in Davao after a WordCamp, but when you don’t have a four piece band there are electronic substitutes.

The first hack to do karaoke anywhere, which I’m surprised more people don’t know, is just search YouTube for [the song you’re looking for] + karaoke. You get something like this Fly Me To The Moon. Every modern TV has YouTube and you’ll be singing along with the TV in no time. I went down a long rabbit hole of wireless mics, auto-tuners, speakers, etc, and I have emerged back concluding that a USB-C wireless speaker microphone gives a lot of the benefits without as much hassle.

The next level up, and worth the subscription, is that the Karafun apps are actually pretty good. You can even run it on MacOS with an HDMI cable to the TV and they have a QR code and queuing system. Pretty slick, pretty fun, Sweet Caroline.

Illuminate has crossed the funding threshold it needed to actually kick off the project of bringing the Bay Lights back to San Francisco, as Heather Knight writes for the New York Times. The upgraded lights will be visible not just from San Francisco but also in Oakland, Treasure Island, Berkeley… all across the Bay. It’s felt like the lights have been the lumen-physical embodiment of San Francisco’s struggles: sparkling and inspiring at the start, then facing troubles, a trough of darkness, and now hope for something better sparked and on the horizon.

I’d love to get as many citizens and addresses in San Francisco as donors, however small, to round out the last bit of the funding, so that as many people as possible can feel the ownership and pride of making the city better. Back in January when I promoted this last it was on a terrible platform, it’s now been re-done by the GiveWP team to be totally native WordPress and a slick donation experience, easy to do on mobile and with Apple Pay. (Major kudos to Devin Walker there!) Please share the link to your friends, especially ones that see the bridge from their home, for $10 it’s the cheapest pro-social dopamine boost you can have every time you look at the bridge.

Mouth Biohacking

I’m not one to shy away from random things I find on the internet, so when I came across the Scott Alexander article on a discovery in the 80s about people who don’t get cavities, my first thought was “how far is Honduras from Houston?”

So on February 28th, my friend Rene and I became the 50th and 51st people to get our normal mouth bacteria scrubbed away and hopefully replaced by a genetically modified strain of Streptococcus mutans that doesn’t turn sugar into lactic acid. A nice sabbatical jaunt.

In the 9 weeks since, no teeth have fallen out, I haven’t gotten any cavities, really the only noticeable change is that I seem to have less bad morning breath, though I still wholeheartedly recommend SmartMouth mouthwash and travel packets.

The company is working on making it more widely available without travel to another country, and if that works it will be interesting to see how long this takes to spread. Will it be adopted quickly or be like the lemon juice cure for scurvy that took 42 years to become policy? In the meantime, the weather in Roatán is warm!

If you’d like to learn more Cremiux Recueil also has a pretty good deep-dive.

Beeper & Texts

It’s such a delight when a plan comes together and unfolds, especially when it’s something you’ve been working on for many years. Today the announcement went out that we’re combining the best technology from Beeper and Texts to create a great private, secure, and open source messaging client for people to have control of their communications. We’re going to use the Beeper brand, because it’s fun. This is not unlike how browsers have evolved, where solid tech and encryption on top of an open ecosystem has created untold value for humanity. Eric Migicovsky has written well about the plan going forward.

A lot of people are asking about iMessage on Android… I have zero interest in fighting with Apple, I think instead it’s best to focus on messaging networks that want more engagement from power-user clients. This is an area I’m excited to work on when I return from my sabbatical next month.

Paul Davids and Jacob Collier

I know I share a lot of Jacob Collier content, but this one is particularly interesting because you can see him learning things in real-time, exploring an instrument that is not his native tongue but he’s already world-class in. It’s so interesting to me the polymath musician friends I have who can play so many instruments how they bring the technique and language across their learning, and this video illustrates it well.

Hugo on Vision Pro

Many of my friends are ridiculous overachievers, and Hugo Barra is no exception. In response to my birthday blog post present request he has published a magnus opus of over 10,000+ words on his thoughts on the Apple Vision Pro from his perspective having been present for some foundational moments for Google, Meta, and Xiaomi. This is my dream, to get people writing more. We need more of this stuff on the internet! It’s fun to go down rabbit holes with experts. Cool that it’s on, too. 🙂

On the Reddit IPO

I’m looking forward to the Reddit IPO, and I think it’s awesome that they opened up a top-tier IPO tranche to their community. People with 200,000 karma points or 5,000 moderator actions on Reddit will get access to something that has previously been reserved for the most elite allies of financial institutions. Wow!

I’m sure this was not easy to do so Reddit users should understand that at this very important juncture in the company’s history it has gone above and beyond to include you. I’m mostly a lurker on Reddit so my 958 karma doesn’t qualify so I’ll get access with the rest of the normal folks.

If I ever IPO something from Automattic, it will include the same for people who have contributed to WordPress. And every supporting open-source project underneath it. (It’s turtles all the way down.)

My only fear is that code contributions are structured in a way that is easily legible, so is anything that happens on, but we may miss including people who have contributed to the growth of WordPress in non-legible ways.

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 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.