It’s a bit of Automattic lore, but although I founded the company in June 2005, CNET asked me to stay on for a few more months to finish out some projects, which I did. Our HR systems have me as the second employee, after Donncha O Caoimh (still at the company!) So today is my 20th anniversary at Automattic! It’s 20 years since I started hacking on Akismet, our first product, and on WordPress.com.
The team gave me a sweet surprise! I’ve been fighting for the open web for 20 years, and hope to do it for at least 20 more. There’s a lot of exciting behind-the-scenes stuff happening inside Automattic that also made this day special, but one significant thing is public.
I don’t think WP Engine employees or investors were aware of the gaslighting they did, hopefully some of this is enlightening. And there’s a lot more discovery to go!
Some days, like this morning when I almost missed my flight to WordCamp Canada in Ottawa, I’m so overwhelmed with the maelstrom of ideas and sparks of creation that it feels like waves crashing against a dam. There are so many ways I can imagine new software, new products, new ways for the world to be.
This is a beautiful process, but it’s also painful! The anguish and agony arise as you attempt to distill the ideas and sparks; the creativity dims, and the beauty and perfection of the original inspiration fade, as I try to translate it into something that can become real and be legible to others. That’s why I have to drop everything when inspiration strikes, because if I try to return to it later, I find the muse has left and I can’t bottle that energy anymore. (There’s a reason Eric, Tantek, and I put “muse” into the XFN standard!)
To the extent I’ve been successful at all in my life, it is because I’m able to contain this tornado and break it down into plans, business models, people, and teams. I’ve never done anything useful on my own; it’s always been in conversation and partnership with others.
Sorry everybody, my @photomatt on Twitter has been hacked, I’m trying to regain account access, but it is not currently in my control. Update: Thank you to the fine teams at X/Twitter and Nikita Bier, my account has been recovered. Just for future reference, I will never promote cryptocurrencies or similar investments. If you see anything from me or WordPress claiming that, be highly skeptical. Invest in open source, public stocks, and great companies like Automattic. 🙂
I’d like to introduce you to Jeremy Kranz. With his career as an investor at Intel Capital, then GIC, which is the sovereign wealth fund of Singapore rumored to manage over $700B, to now running his own fund Sentinel Global, he has had a front-row seat to investments in industry changing companies such as ByteDance (which became TikTok), Alibaba, Uber, DoorDash, Zoom, DJI (which changed the drone industry and argubly modern warfare), and many more I’m probably not even aware of.
When I first met Jeremy in 2014, I was amazed that a late-stage financial investor could understand Open Source so well, and he immediately grokked what Automattic was doing in a way that I think has little parallel in the world. (Today, it reminds me of Joseph Jacks at OSS Capital.) Deven Perekh of Insight Partners led Automattic’s 1.16B valuation Series C round, making us one of only forty “unicorns” (private companies valued over a billion dollars) at the time, and one of the reasons they beat out others as the lead of the round was that GIC/Jeremy was a LP of Insight so they could directly co-invest. GIC is so intensely private I couldn’t even mention them in the announcement at the time even though they were the catalyst for the round. Since then, Jeremy has become a close friend and advisor, and he even took me to my first Grateful Dead concert.
Eleven years later, this is his first podcast! Jeremy shares incredible alpha around China, AI and its adoption in the enterprise, how asset allocation is evolving, and at the end, a beautiful tie together of the Grateful Dead and Open Source.
Beeper has a fun set of September updates, adding support for Google Voice, LinkedIn now runs on-device, typing indicators for Google Messages and Instagram, full Telegram custom emoji support, and more.
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 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.
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!
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:
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.
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.
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.
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.
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:
Here’s how to set up Clay’s MCP so your AI can ask things like “Who are my contacts at Google that I haven’t spoken to in 6 months?”
Beeper’s MCP implementation lets you query your entire message history across iMessage (on MacOS), WhatsApp, Telegram, Signal, Instagram, and many more with natural language.
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.
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.
It’s been a busy (and tragic) week but one of the more interesting things to launch was the Really Simple Licensing standard. I have a lot of scars from the web standards wars, so I’m hesitant to dive back in, but this is from a lot of the early Web 2.0 people, as TechCrunch writes about.
The New Yorker is always good, but they’re having a bit of a victory lap as they celebrate their centennial. This article on the vaunted fact-checkers is such a delight, with so many in-jokes and back references it’s hard to keep track.
When I started WordPress, I wrote down five publications that I hoped someday we’d make software so good they’d adopt it. The New Yorker is one of them. If you enjoy words that make your brain tingle, make sure to also follow Automattic’s publications, Longreads and Atavist.
I’m still buzzing from an incredible WordCamp US this week, from contributor day to the closing party the vibes were right and it was amazing to connect with fellow travelers in the journey towards creating a more free and open source internet.
Before our open town hall Q&A I was able to make some fun announcements:
Traffic to WordPress.org is up, and we’ve brought the plugin queue from months to basically a few days.
Previewed Block Comments and the upcoming Command Palette feature in 6.9.
Over the weekend, Automattic/Beeper had the pleasure of hosting and sponsoring the Build the Future MCP Hackathon in New York City organized by Adam Anzuoni, alongside Anthropic, Stainless, WorkOS, Smithery, and MongoDB. As someone deeply passionate about open-source technology and the potential of AI, I was thrilled to not only support this event but also to speak at it and serve as one of the judges. For those unfamiliar, MCP stands for Model Context Protocol and enables AI models to interact with multiple tools in a more efficient and structured manner, allowing developers to create sophisticated agents that can handle complex tasks. And it’s only 8 months old! The energy in the room was electric—hackers collaborating, iterating, and demoing groundbreaking projects in just a few hours. (I would love to see the results of a longer overnight or all-weekend hackathon.)
For a wrap-up of the winners, check out this great X/Twitter thread by Alex Reibman. The first-place winner, Levels AI, orchestrates different AI/ML models to solve specific business requirements without needing heavy manual coding or specialized teams. Essentially, it’s models creating more models—a meta-approach to AI that could streamline operations for companies of all sizes. Yusuf Olokoba said the name was inspired by Pieter Levels, which is pretty cool. I wanted to note one team in particular: BeepResearch, which used our early access Beeper API and local MCP.
6/ BeepResearch (Bonus)
MCP server to chat with your messaging apps like iMessage, Whatsapp, FB, X, etc. over @beeper. And Ollama + gemma3 to query photos in natural language
Judging the entries was tough! People built so much cool stuff in a really short period of time. I always say technology is best when it brings people together, and this was a great example of that, and makes me very excited for Contributor Day at WordCamp US next week. (Which has such a stacked AI program as well.) Hopefully some people who enjoyed the office might consider getting 24/7 access.
I also just want to take a beat and say how amazing it is that I’m blogging this, on a United flight from Houston to San Francisco I’ve taken a million times, on a plane 36,000 feet in the air and technology is amazing. I can’t wait until United has Starlink!
