Category Archives: Asides

Interesting links.

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.

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!

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.

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.