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.


Birthdays are so great because they’re about generosity.

The act of giving, helping, is so generative.

It’s what we can all do for ourselves and each other.

But accepting is really hard, too! Gosh! Let it in.

Sometimes we don’t let the gifts in.

Approaching forty has felt impossibly light and heavy at the same time for me.

It’s so cool to be typing this into something we made together. I want you to really think about that. Ponder the enormity of all that came before that allowed you to be here today, and I want you to get a little bit excited, in that sacred hidden part of your heart that yearns for more.

Let’s keep doing that. And let’s make it better and share it so everyone can enjoy it. We make the world.

I’ve been enjoying so much all the posts coming in for the birthday gift. I’m reading them as fast as I can.

Specifically, my failure mode is I share too much. I’m too generous. I like to err on the side of open. Here’s some amazing code I wrote that you have a legal license to use however you like. If you ask those closest to me how I mess up, it’s that I over-extend myself and try to do too much.

I’ve never shared this publicly, but when the Bay Lights wasn’t going to make it the first time, I mortgaged my apartment and used that money to get it over the line. My personal finances were messy for years after that. I think a lot about being impeccable with my word.

I want people to give the smallest $10 donation to the Bay Lights and encourage others to do the same so that we can all share in feeling that together, we can build things. And every time you see the light or bridge or think of San Francisco, you’ll think of that sacred hidden part of your heart that yearns for more, wants to leave everything better than you found it.

Add some light.

Let the gift in.

This is the part where the sounds come in and you hear it’s the remix.

I find myself returning, again and again, to the Automattic Creed, especially the first line:

I will never stop learning. I won’t just work on things that are assigned to me. I know there’s no such thing as a status quo. I will build our business sustainably through passionate and loyal customers. I will never pass up an opportunity to help out a colleague, and I’ll remember the days before I knew everything. I am more motivated by impact than money, and I know that Open Source is one of the most powerful ideas of our generation. I will communicate as much as possible, because it’s the oxygen of a distributed company. I am in a marathon, not a sprint, and no matter how far away the goal is, the only way to get there is by putting one foot in front of another every day. Given time, there is no problem that’s insurmountable.

I’m having the most amazing day reading everything that people are sharing. I want to re-share the quote I shared on Tim’s podcast from Will Durant:

Health lies in action, and so it graces youth. To be busy is the secret of grace, and half the secret of content. Let us ask the gods not for possessions, but for things to do; happiness is in making things rather than in consuming them.

All birthday posts: 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40.

Sonos Tip

If you’re obsessed with Sonos like I am, a nice MacOS utility is the Menu Bar Controller. Hat tip to Mike Tatum, who happened to be the gentleman who convinced my parents it was okay for me to drop out of college and move to San Francisco to take a job at CNET. Mike’s now at Sonos and in October arranged for some top execs at Automattic to go to Santa Barbara to meet with their peers at Sonos, and Patrick Spence and I did a joint CEO town hall that was broadcast to both of our companies. It was I think fascinating for both sides because of a shared passion for craft, design, culture, and execution, but our companies are in no way competitive, so it allowed for a lot of transparency. I learned a ton, and I think that kind of sharing is what increases the mimetic evolutionary speed of companies.

Atoms are hard! I think I’ll stick mostly to bits.

Back With Tim

I returned on the podcast with my good friend Tim Ferriss, by my count the sixth time we’ve recorded together, but the very first time we did it in video! Tim asked me to bring five things I’m excited about, five things I’ve changed my mind on in the past few years, and five things that are absurd or ridiculous but I still do, and that ended up being a pretty fun anchor for a two-and-a-half hour conversation, which you can watch here:

Or listen to on Pocket Casts or any podcast player, thanks to open standards:

I ended up having more than five things for each list, especially the excited one, but tried to edit it down. This was a very vulnerable and personal conversation for me, which I think was possible because we’ve known each other so long at this point and Tim made it really easy and fun to open up. We discuss everything from open source to kids to my upcoming sabbatical.

Coincidentally, this was episode 713, which is the original area code for Houston! We didn’t plan that but I think that’s so cool. I’m also going to watch his episode with Kevin Rose who he’s also very close with, I always learn new stuff from those two.

Birthday Gift

It’s true, it’s true, I turn forty years old in ten days.

What do you get the guy who has everything?

I admit I’m not the easiest to shop for, I can be quite particular in my preferences of this cable versus that one, but the good news is the gift I most want for my 40th is something everyone can do.

I want you to blog.

Publish a post. About anything! It can be long or short, a photo or a video, maybe a quote or a link to something you found interesting. Don’t sweat it. Just blog. Share something you created, or amplify something you enjoyed. It doesn’t take much. The act of publishing will be a gift for you and me.

That’s what I want for my birthday. If you link to this post and use WordPress the Pingback system will notify me about your post and it will show up in the comment stream, but I’m okay even if you don’t use WordPress, just post something and send me a link. You can start a free site on Tumblr or get a domain that can be your home on the internet with WP.com.

You’ve got ten days! After the 11th I’ll close the comments and pingbacks on this post. But I’m so curious to read what people write.

That’s it! No wrapping paper or bows. Just blogs and blogs and blogs, each unique and beautiful in its own way. (Oh! And put $10 toward the Bay Lights so we can get the contributor number as high as possible.)