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.

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?

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. 😂

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.

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: 

If my calendar is correct, one of the OG bloggers Anil Dash is turning 50 today! His blog, which I believe has been active since 1999, inspired me with how he effortlessly transitioned between his top-tier fandom of Prince and his thoughtful commentary on the nuances and second-order effects of what we were doing with blogging, micro-blogging, web standards, interoperability, and much more. His writing is incisive and insightful. I see a core flame of empowering independents throughout his career that very much aligns with the philosophies I aspire to. Please follow him if you don’t already, and happy birthday Anil! It appears that I have linked to him 15 times on my blog before this post, and he has commented 17+ times, the first in 2005, so we have some history! Since I started drafting this he published his Five for Fifty birthday post.

You might be a WordPresser if…

• You like to have freedom and control over all your software.
• You don’t mind taking a bit more time to invest in tools that give you agency.
• You like inserting little opportunities for joy in everyday interfaces.
• You want future generations to grow up with a free and open web.
• You like to tinker, hack, mod, customize, and share what you learn.
• You are impeccable with your word.
• You think software should have a little soul in it.
• You love giving other people superpowers, teaching them not to need you anymore.
• You appreciate a good plan but want to be able to color outside the lines, or completely reimagine the canvas altogether.
• You think technology is best when it brings people together.
• You get excited by updates.
• You want your corner of the web to truly be yours, not generic or commoditized slop.
• Your friends come to you to learn about new stuff.
• You leave things better than you find them.
• You fix things as you find them, it’s never someone else’s problem.
• You know a single comment can light up someone’s day.
• You’ve gotten out of the house to meet other people into WordPress.
• There’s a Wapuu item or sticker somewhere in your life.
• You “view source.”
• You know the difference between owning your content and being a digital sharecropper.
• You’ve drunkenly registered a domain, and have more domains than websites.
• You’ve snuck an easter egg in a slug.
• You have a Gravatar, and it’s also a museum of all your email identities over the years.
• You think code can be poetry.

If you identified with two or more of these statements, I am afraid to inform you might be classified as a WordPresser. What did I miss?