Saturday Shares

Asides

A few links for you:

Fun fact: this post has the ID of “150,000” in my wp_posts table.

Five Publications I’d Love on WordPress

Asides

When WordPress started in 2003, I never dreamed it would power over 40% of websites, nine times the number two CMS, but I wrote on a notecard a list of five publications I admired and respected so much I wanted them to run on WP someday. In the interest of sharing your dreams to help them come true, here they are:

  1. Atlantic
  2. Economist
  3. New Yorker
  4. New York Times
  5. Wall Street Journal

And one bonus: Houston Chronicle. (Gotta root for the hometown.)

There has been uneven progress toward this over the years; we’ve gotten some of the NYT and all of the New Yorker at one point, only to have them revert under new CTOs. Also, there have been some unexpected huge wins, like when Vox Media retired its proprietary CMS Chorus and brought over amazing publications like The Verge and New York Magazine. For any projects related to these publications, including trials or micro-sites, I’d be happy to provide my feedback on architecture, design, and opportunities, and contribute Automattic and VIP resources wherever they could be helpful.

I believe the most crucial aspect to get right for these customers is real-time co-editing, which is on the Gutenberg roadmap and shipping soon. If I were writing this list today I might choose some different targets.

Harry Mack

Music

I love the culture of freestyle rap, it’s so inspiring to see how people can create such rich poetry riddled with allusions and puns on command. Last week I got to meet Harry Mack and see him improvise live and it totally makes sense that he has a jazz drums background. If you’re not familiar with Harry Mack, this is a good example of him taking three words: Imported, Lurking, Automatic and freestyling with them. (BTW, if you noticed, we finally got the domain spelled correctly.)

There is a video chat site called Omegle that paired you with random people, and Harry would record these encounters, such as this cute one with girls from Sweden who gave him the words Cartoon, Titan, Death. It’s awesome to see him meet Will Smith and Martin Lawrence.

For some fun WordPress rap history, check out when Childish Gambino referenced me in a rap he performed on Tim Westwood back in 2012.

Telex Remixes

AI, Automattic, WordPress

Telex has launched a new design and a gallery of some interesting examples. It’s really cool to see what people are starting to do with Telex, it really gets back at the fun of hacking and coding at the beginning, when a computer does something for you that makes you gasp.

My colleague Eduardo Villuendas has been making some cool music with it.

This really gets to my vision for Gutenberg to be a builder that anyone can use to create an incredible website, like legos anyone can assemble anything they imagine on the web. This is why I said Gutenberg is bigger than WordPress.

Hat tip to the Gutenberg Times. As I said in 2022, you need to learn AI deeply, there is so much fun stuff happening. They even like it on Reddit.

Nick Diego writes how Telex Turns Everyone into a WordPress Block developer.

Ruby Drama

Open Source

There is some riveting drama in the Ruby community around company sponsorships, and directory nudging similar to what happened with Advanced Custom Fields and Secure Custom Fields. This post does the best summary: Shopify, pulling strings at Ruby Central, forces Bundler and RubyGems takeover.

I will only add that Automattic attempted to sponsor RailsConf and have a booth for our open web apps, such as Pocket Casts, Day One, and Beeper, which we thought would be relevant to the open source and open web audience there; however, we were denied. We’ve sponsored other open-source events like DrupalCon before and did so in a tasteful way that wasn’t in conflict with the organization’s mission.

Post-Earthquake Tea Grit

Press

The 4.7 earthquake definitely disturbed my sleep last night, so it’s nice to have a Cuzen Matcha shot and some Harney & Sons Paris tea to wake up and get me through the day.

Speaking of spilling tea, I had a great conversation with Joubin Mirzadegan of the storied VC firm Kleiner Perkins where we got to chat about the hero’s journey of entrepreneurship, my earliest “Hot Nacho” WordPress scandal and the context of current battles, 996 work, jazz clubs in San Francisco, and more. Kleiner never invested in Automattic (I don’t think we ever pitched) but I have always had huge respect for John Doerr, Brook Byers, Bing Gordon, Mary Meeker, Ilya Fushman, and Mamoon Hamid, so many of the people at KPCB. You can watch on YouTube or listen in Pocket Casts.

If you’re not playing music while you’re working, you’re missing out. It’s incredible how sounds can transform how our brain works. You can, on tap, put yourself into a different mode of being with music; you can change your drive, motivation, mood, and more. There are some apps that have started to hack this, such as Endel, which can generate music programmatically in a very Brian Eno-like way. I’ve been a fan and user of theirs since 2020. I also love the Lofi Girl. On your Sonos you can actually stream Focus @ Will, which is another attempt, and I have a subscription there. My favorite is Endel, though, so if you’re only going to try one, try that one.

When my father passed unexpectedly, I was despondent. One thing I remember was the Amazon lovebomb I got from my high school girlfriend Sunaina Sondhi, five books to help me deal with the pain. Even a decade after we dated, books were her love language; in fact, she had given me my very first book about meditation when we were teenagers. I don’t recall what all the books were, but the two that really made a difference for me were Elisabeth Kübler-Ross’s and David Kessler’s posthumous book On Grief and Grieving, and the Tibetan Book of Living and Dying. Each allowed me to process and understand the emotions I was going through.

MCP Everywhere

Automattic, WordPress

MCP stands for Model Context Protocol. (The joke is the S in MCP stands for security, but that’s another post.) They say to think of it like “like a USB-C port for AI applications” because it allows interoperability between AI chatbots and other tools. Here’s some of the MCP stuff happening across the Automattic solar system:

When nerds start connecting things, interesting stuff happens; that’s been my entire career, so while none of these have made it into a critical daily workflow for me, I’m curious to see what people come up with.

Every 6 Minutes

Asides

I’m at a dinner tonight and they have these old magazines on the table, including some old copies of WIRED, which, if you can imagine, as a kid in Houston in the 90s, was a portal to the amazing world of the internet and technology. I flipped through, and there is an entire web hosting classifieds section! Hiway Technologies wants you to know that every 6 minutes, someone hosts with Hiway.

Every six minutes, so they were doing 240 signups a day. 100,000 sites! Last month WordPress.com created a new site about every 3 seconds. Hiway was founded by Scott Adams, same name but not the Dilbert guy or the game designer, who apparently played football in Florida and the company “was sold in 1999 for $352 million. Adams was 35.”

There was also this guy, who has a website, but do you?

United Starlink

Asides

I’m on my first United flight with Starlink, and wow! I ran a fast.com test and got 110 mbps down and 38 mbps up, which is insane. 28ms ping times. While flying! When you think of all of the engineering and technology coming together to let me blog this it’s really incredible.

Update 2025-09-16: United actually responded to my tweet about this. 😂

Weekend YouTubes

Asides

One of my favorite YouTubers is Charles Cornell (WordPress-powered!), who creates great videos that break down the music theory of various things you’ve heard, such as this adorable one featuring SNES soundtracks or The Legend of Zelda: Breath of the Wild. I first came across him reacting to Jacob Collier in 2020. Once I got super-into Severance, his breakdown of the spooky music is great. It’s also interesting to see that the YouTube community is going through its own version of fair use and copyright, trademark, etc., enforcement, which he discusses here.

Sam Altman is always interesting to follow, and it’s interesting to contrast this great interview he did with David Perell on writing with this very direct and awkward one with Tucker Carlson. I have immense respect for anyone who enters the arena and engages directly with journalists or critics, rather than hiding behind PR agents or lawyers. Given the current blood feud, it’s fun to go back eight years and see Sam Altman interview Elon Musk, long before any of the AI stuff blew up they were both terribly prescient.

Ray Dalio is always a gem and he went on Diary of a CEO. Theo Browne has a good take on what it means to vibe code. Kishan Bagaria discusses how Beeper is going to reach 100 million users. The story of how Atlassian took a non-traditional enterprise path with Jay Simons is great. Not a YouTube, but don’t miss Bret Taylor on The Verge. Check out Adam D’Angelo at South Park Commons.

And finally, I’ll say that YouTube Premium, which turns off all the ads, is probably one of the highest value subscriptions you can have. Many of these are essentially like podcasts, and from a product perspective, I think we need to figure out how to sync and allow seamless movement between watching, listening, or reading transcripts in Pocket Casts (Automattic’s open-source podcasting app). We support video podcasts, but there’s no good way yet to have a Whispersync-like experience between video, audio, and a transcript.

Old Business Cards

Asides


I recently came across a few old business cards I designed back in 1999. The first ones were for my services as a saxophone player:

A few notes:

  • I went mostly by “Matthew” then.
  • At some point I decided to remove the home address and say that I was available to play not just alto saxophone but baritone, tenor, and soprano as well.
  • The number was the home shared house number, not a cell phone.
  • The email was an email address the entire family shared, under my dad’s name.
  • HAL-PC was an amazing non-profit local to Houston that stood for the “Houston Area League of PC users.” There was a pretty reasonable annual membership fee, and they hosted a monthly general meeting which had hundreds of attendees, always with a presentation or two and a raffle giveaway at the end. They were a dial-up ISP and BBS/newsgroup host. I volunteered for them by going in on Saturdays where they had a room people could bring their broken computers to and get free tech support, and by hosting a SIG, or special-interest group, around PalmOS called HPUG, the Houston Palm Users Group. This was a big part of the inspiration for WordCamps.

This was for my “design” business:


I would also design business cards for friends, here’s one for my friend who was a percussionist and vibraphonist, Chase Jordan: 

Just got word that the court dismissed several of WP Engine and Silver Lake’s most serious claims — antitrust, monopolization, and extortion have been knocked out! These were by far the most significant and far-reaching allegations in the case and with today’s decision the case is narrowed significantly. This is a win not just for us but for all open source maintainers and contributors. Huge thanks to the folks at Gibson and Automattic who have been working on this.

With respect to any remaining claims, we’re confident the facts will demonstrate that our actions were lawful and in the best interests of the WordPress community.

This ruling is a significant milestone, but our focus remains the same: building a free, open, and thriving WordPress ecosystem and supporting the millions of people who use it every day.

Account for Externalities

Economics, Open Source, WordPress

When I studied economics, one of the concepts that struck me the most was the concept of externalities. This International Monetary Fund post explains it well. In short, externalities are costs or benefits of an economic activity that affect third parties who did not choose to incur them, leading to a divergence between private and social costs or benefits. They’re spillover effects—positive or negative—that the market price fails to reflect. A classic example is air pollution from a factory, where nearby residents bear health and environmental costs not included in the price of the factory’s products.

Open source is full of externalities. On the positive side, adoption creates ecosystems of developers and provides many paths of distribution. On the negative side, there’s often underinvestment in the very projects that sustain the ecosystem. I have a lot of empathy for why, when open source meets finance and private equity, things can go sideways. You can look at a business built on open source and see seemingly amazing margins—efficient R&D that compounds in a DCF model. A percent here or there over many years really adds up.

My plea to investors in open-source businesses is this: when a business is built on top of open source, incorporate a restorative investment percentage back into the projects critical to the end-user experience of what you’re offering customers. In WordPress, we call this Five for the Future, but it doesn’t have to be five percent; it could be 0.1%. Plan for it when modeling your expected IRR hurdle from an investment. Then, a few years down the line, when the small percentages start to add up, you won’t face a big catch-up or gap.

This underinvestment is itself an externality. It doesn’t appear on the balance sheet, but it can manifest in black swan events, such as security breaches or remote code exploits. Technical debt is one of the largest unaccounted-for externalities in the world today. Engineering, in the long run, is primarily a craft of maintenance rather than creation. The bulk of the cost of something comes from its upkeep over time.

PostHog

It’s always fun to see someone pushing the limits of the web experience, as I reminisced about Flash and Dreamweaver the other day. The new website for Posthog is a delightful rabbit hole to explore, akin to a Meow Wolf, with meticulous care and craft applied to every corner of the product in a way that is both fun and playful. They even have their own version of pineapple on pizza.

What I want to enable with WordPress is the ability with thousands of plugins and themes for people to have unique, funky experiences like this on their website, while still providing a content structure that’s legible for interoperability and hacking. Major kudos to Cory Watilo and James Hawkins for coming up with this.