Linkrot

Press, WordPress

One of the things I hate most on the internet, and part of the reason I started WordPress, was to fight linkrot. Ever since 1998, when Tim Berners-Lee wrote “Cool URIs Don’t Change,” I’ve been obsessed with content management and ensuring that links don’t break. (BTW, TBL, a pioneer of creating the World Wide Web, has a great new profile out in the New Yorker.)

I learned today from the Newspack newsletter that the Houston Press is now on WordPress. Newspack is a distribution or bundle of WordPress designed for journalism, and it is led by Kinsey Wilson, who began his career as a night-shift journalist covering cops for a newspaper in Chicago, went on to have top editorial and business positions at The New York Times, NPR, and USA TODAY, and ran WordPress.com for a few years, which gives him a very unique position to help craft WordPress for journalists and publishers.

The Houston Press is an alt-weekly that wrote the very first profile of me in the world, which I blogged about here. There’s a funny quote in there:

He recently considered taking a job with a San Francisco search-engine start-up, but ended up turning them down. “They have a ton of money…But it would be 50- or 60- or 70-hour weeks, a lot of work, and I wouldn’t have time” to do WordPress. 

That “search-engine start-up” was Google! How the internet might have turned out differently if I had taken that job, as my Mom wanted me to (because they offered free food). I still think Google is one of the most interesting companies in the world, one of the few places I’d consider working if I weren’t running Automattic.

Back to linkrot, the original link to the profile in that article was http://www.houstonpress.com/issues/2004-10-28/feature2.html, which this morning didn’t work, but thanks to the Houston Press being on Newspack/WordPress I was able to ping Kinsey and his colleague Jason Lee was able to fix it so it redirects to the new canonical URL for that content in minutes. A little corner of the internet tidied up! I love the Wayback Machine, but not needing it is even better.

Fight For Open

Apple, Automattic

Sometimes the battle for open source and freedom can take on very prosaic and practical terms, but the wins can benefit everybody. To give an example: In Beeper we need more memory for showing notifications, because we support end-to-end encryption for networks like Signal, but Apple’s default was to only give 15 megabytes — barely enough to do anything. The previous CEO of Beeper, Eric Migicovsky, started a lobbying effort with the EU’s Digital Markets Act on behalf of the team to give third-party apps the same memory limits that Apple provides for their own apps, which is 50MB instead of 15MB. (And up to 250MB on their higher end devices.)

Today we’ve gotten a notification that as part of iOS 26 update Apple has shipped to 2.3B devices around the world, our memory limits issue has been addressed globally, for every application developer, and some interoperability requests we had for SMS/RCS have been addressed for EU users. Kudos and huge thank you to Apple for giving us all new capabilities to build amazing experiences for users on par with what they seek to deliver themselves. If you want to geek out on this, check out the technical deep dive that Beeper just posted.

BTW, if you haven’t heard of it yet, Beeper is an Automattic product which aims to democratize messaging, just like WordPress democratized publishing for the world, by allowing you to get all your messages from friends across 11 different networks, like WhatsApp, Instagram, Telegram, Twitter/X, Signal, Discord, in one single inbox. The new version we launched in July does this in a completely secure way that’s local to your device, so the same encryption, privacy, and security each network provides is maintained.

I think some of the best writing about technology PR is this ten-year-old article by Aaron Zamost: What’s Your Hour in ‘Silicon Valley Time’? It describes the cycles that companies go through in public perception, and the beauty of revisiting it ten years later is that you can see which of the examples are still relevant, or the domains that 404. As someone who has been around this clock probably a dozen times now, I highly suggest this for anyone “going through it.” Some of the most powerful words in the English language: This too shall pass.

See also: The Zen fable or old Chinese poem of the old man who loses his horse.

Om 59

Personal

I want to dedicate my blog post today to my dear friend and brother, Om Malik, whose birthday it is. Om is a multi-hyphenate, but at his core, he’s a writer, someone who looks at the world and parses it down for others, a seeker who appreciates the spark of creation before most others.

Om was one of the earliest users of WordPress and he was one of 8 people who came to the very first WordPress meetups at Chaat Cafe on 3rd street in San Francisco in 2005. (You can tell what an early adopter he is because he has the username “Om” on Twitter/X and Instagram and WordPress and probably more.) We had connected on the WordPress support forums when I helped him get set up around the 1.0 days. After I moved to San Francisco to take the job at CNET he connected me to people like Phil Black, Tony Conrad, and Toni Schneider who would become, respectively, an investor, board member, and CEO of Automattic. These are folks I still work with and consider close friends today. As a journalist, he had a keen nose for BS and made sure as a naïve 20-something in SF I was connecting with quality people.

Since we met we’ve both had a shared love for photography, and I’ve seen Om blossom into an amazing photographer with a really unique style and approach, in fact you can even buy some of his photography prints.

Over the years, we’ve dipped in and out of shared obsessions with cameras, watches, shoes, fashion, and design. We have a fair number of matching things in each. In photography we’ve shivered in minus thirty weather in Antarctica and Jackson Hole at odd hours to catch a special shot. We’ve traveled to Europe and Japan dozens of times, being very early (pre John Mayer and Kanye) to brands like Visvim. When I wear something like a bespoke, hand-made piece from 45R to speak at WordCamp US, he recognizes it off the cuff and even knows the one store on Crosby Street in New York where you can buy it. He is a tastemaker and an aesthetic connoisseur in every area he’s interested in, from food to coffee to pens, and everything in between. Sometimes we’ll start a journey together, for example, trying nice pens, and years later, I’ve moved on and he’s gone deep into collecting dozens of them, being in obscure forums and Reddits, or attending events like the SF Pen Show last month.

When you walk into a coffee shop with Om he doesn’t just know the barista’s name, he knows their dog’s name and the story of every person working there.

I’m 500 words in, and I still haven’t even scratched the surface of describing Om’s journey, from growing up in Delhi to becoming a journalist for a Japanese publication in New York, a book author, party promoter, entrepreneur, venture capitalist, photographer, and explorer. If you want to understand the AI bubble we’re in right now, you should read his book Broadbandits on the crazy telecom / Enron bubble. This is a long way to say, happy birthday Om!

Craft vs Slop

AI

In an age where AI can generate an infinite amount of stuff, what matters? Some of the most interesting writing I’ve read on this comes from Will Manidis, who makes it biblical and says that Craft is the Antidote to Slop:

From Genesis, man enters not a paradise without labor but a world of intentional creation. The LORD God places man in the Garden of Eden “to dress it and to keep it” (Genesis 2:15) establishing labor not as punishment but as sacred vocation. This original calling invites us to co-create the Kingdom, tending and developing the world with intention and care. Our fundamental purpose is not consumption but participation in the ongoing work of creation.

The serpent’s temptation represents the first shortcut in human history.”Ye shall be as gods” (Genesis 3:5) was not an invitation to deeper engagement with creation, but a way to get out of the work required to tend to it. The consequence wasn’t the introduction of work itself, but its corruption into burdensome toil: “In the sweat of thy face shalt thou eat bread” (Genesis 3:19). Humanity’s first sin was, in part, choosing the easy shortcut over the meaningful process – preferring effortless gain to the demanding but fulfilling work of tending the garden.

You can read the rest as screenshots on X or on his Substack, but I hope he gets a real website soon. This also makes me think you should watch the We Are As Gods documentary on Stewart Brand, supported by the amazing folks at Stripe Press.

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: