Category Archives: Automattic

Happy Birthday Kinsey

Yesterday I had the great honor and privilege of attending a colleague’s 70th birthday party. You may not have heard his name before, but Kinsey Wilson has been at the center of shaping journalism with a movie-worthy career that started at the bottom as a crime reporter in Chicago, and has taken him to the highest echelons at NPR, the New York Times, and, most recently, we’ve been lucky to have him at Automattic.

Kinsey brings a journalistic curiosity and passion for finding truth, paired with a deep optimism and creativity for seeing around the corner for how technology can transform how we consume and produce media.

While his Wikipedia page or biography provides appetizers to some of what he’s done, Kinsey has led such a rich and beautiful life that any attempt to summarize it ends up being criminally reductive. The best you can hope for is to give a taste of his person through vignettes.

A beautiful snippet from the montage of accolades at his birthday was how Kinsey was someone you’d follow into battle. I’ve learned so much from seeing the empathy, candor, and integrity he brings to every team he leads, which engenders an incredible loyalty I’ve rarely seen in my career. When he left NPR, 62 colleagues made an “Infinite Kinsey” website of accolades.

That sort of thing is rare, and it’s been an honor and a privilege to work alongside him to democratize publishing.

One of those colleagues, Elise Hu, introduced us while he was at the New York Times and while my intention when I first met him was to get more WordPress at the Times, my imagination was sparked by thinking of how he could bring his experience to help shape WordPress and Automattic, hence my pivot into recruiting him.

Kinsey’s impact on journalism (and podcasting!) at NPR and New York Times is easy to understand, but less well-known is how he came into Automattic and got deep into understanding WordPress and seeing it as a platform that could enable the newsrooms and journalists to accomplish their mission in a more efficient way with the project he leads, Newspack.

He’s a fierce steward of the Fourth Estate.

Newspack and its team’s close relationship to customers invents solutions on top of WordPress that delight its users and percolate and influence everything we do at Automattic. They’re one of the teams that sets the bar for others in the company.

To Kinsey, I’ll leave you with a quote from one of my other inspirations, Charlie Munger, who at the tender age of 99 shared a wish with a visitor, “Oh, to be 86 again.”

I’ll try not to be too tech-bro optimist and say that 70 is the new 40, but I look forward to seeing the ripples that you have on the future of publishing for many years to come. 

Automattic 20 & Counter-claims

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.

Automattic has finally had its first chance to file its counterclaims that spell out the bad actions of WP Engine and Silver Lake, as reported here by TechCrunch. You may recall that last month, the court dismissed several of their most serious claims, and they responded by filing an amended complaint. In our dogged defense of the free, open, and thriving WordPress ecosystem, Automattic responded today with a comprehensive counter-filing, which you can read in a 162-page PDF here about all the things WP Engine/Heather Brunner and Silver Lake did wrong.

We’ve got receipts!

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!

Jeremy Kranz and Sentinel

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.

Fight For Open

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.

Telex Remixes

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.

MCP Everywhere

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.

WP.com Simplification

WordPress.com offers two modes of WP: WordPress and WordPress MS. For free and lower-priced accounts it runs a version of WordPress called WordPress MS, or WordPress Multisite, which is designed for super-efficient multi-tenant usage, which is what has allowed it to introduce hundreds of millions of people to WordPress and run at a huge scale. (It was initially called MU, for multi-user, but we had to change it because someone squatted the name WPMU and built a business on top that was confusing users with commercial products. Such is my curse.) It revolutionized the hosting industry in a number of ways, including acclimating customers to per-site pricing instead of unlimited domains and raising the bar for what a host would manage for users so they didn’t have to worry. It has also provided a highly secure base login, which allows us to offer popular SaaS services, such as statistics and anti-spam, to all WordPress users, regardless of where they’re hosted.

At higher-priced plans you’d get access to not just a curated set of plugins and themes but the ability to install anything you like from the ecosystem, which invisibly switches your account to WP.cloud in the backend that supports unlimited plugins and themes and custom code, in a way that’s still multi-datacenter and maintenance-free. This has been very successful and works great for a ton of customers, but it still puts an asterisk when you recommend WordPress.com to someone because they’d need to be on one of the higher-priced plans to get an experience of WordPress with custom plugins and themes.

For the first time ever we’re running a summer special where every single paid account gets that full WP.cloud experience with full customization and control. It’s a test we’re running until August 25th. It’s WordPress, without the asterisk, without limits, implemented in a way that’s intuitive and safe for novice users, while also being extremely powerful for developers. If you haven’t checked out WP.com in a while, it’s a great deal starting at just $4 per month. I’m curious to see the results of how this goes. We also have a number of more radical things I’m eager to try out! It’s a great time to reimagine what you’re doing from the ground up and question your longest-held beliefs, as AI has really put people in a more experimental and open mindset.

Beeper and Automattic 20

To announce and celebrate the incredible engineering achievement of the Beeper team launching local bridges and their premium model we hosted a fun event in Automattic’s space in NYC. The app side of Automattic does some amazing work, and the applications themselves are pretty well known and reviewed, but many don’t know they’re part of Automattic, so it was a good opportunity to tell that side of our story a bit. Here’s the video from the event:

And if you’ve ever wanted to get better control over your instant messages, regardless of what network they may be on, definitely check out Beeper. I find it especially useful on desktop, like a Superhuman for messaging.

Back on The Verge

In honor of Automattic’s 20th anniversary, and also since it’s been a few years, I joined Nilay Patel the editor-in-chief of The Verge on their Decoder Podcast. We talked about Tumblr and the Fediverse, how Automattic thinks about Ecosystem and Cosmos sides of the business, Automattic’s re-organization into cross-business functional teams and leadership, the vision of Clay as a personal CRM and Beeper as the super-human messaging app that puts control in the hands of users, Newspack, the future of websites, the obligatory coverage of the alleged WP Engine trademark violations and their subsequent preemptive suit, and much more. Please give it a listen! They chose the title “Why Automattic CEO Matt Mullenweg went to war over WordPress.”

Speaking of Beeper, we’re going to do a fun event for the next-gen version that’s launching on July 16 in New York City in NoHo. I’ll be there along with Beeper CEO Kishan Bagaria and some of the best and brightest in New York’s tech and creative class. If you’re a Beeper early adopter (or would like to be) and want to attend, leave a comment! We’ve held back some invites for cool folks like readers of ma.tt. 🙂 It’s like getting on board with WordPress in 2004.

Automattic Twenty

We’re celebrating a fun anniversary at Automattic today, our 20th, with a fun look-back. Gosh, it’s been quite a journey, and it still feels like we’re just getting started in so many areas.

In 2005, being a remote-first company was anathema to investors and business leaders* at the time; it was a scarlet letter that combined with our embrace of Open Source and the relative inexperience got us some funny looks and a lot of skepticism. I will be forever grateful to the true contrarians who bet on Automattic in our earliest days.

Even when it was clearly working the first few years, there was always the dismissal of “that won’t scale” that loomed like a remote startup Great Filter. These days I hear from friends who run incubators or do seed investing that almost every company they look at taps into remote talent.

It makes me think about what uncommon things Automattic does today that will be standard in the coming decades. We do our best to balance idealism with pragmatism, because even if you are on the right side of history, being too early can be as bad as being wrong.

I can’t predict everything that will change over the coming decades, especially with AI making the next few years particularly hard to predict. Still, I do know a few things that won’t change: everything flows from our people, open source is still the most powerful idea of our generation, growth is the best feedback loop, 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. People will always want fast, bug-free software; instant, omniscient customer service when they need it; and experiences so intuitive that they usually don’t. And once they’ve had a taste of freedom, it’s hard to return to their previous state. (For more, see our creed.)

Our industry is highly cyclical, and I feel fortunate to have gained the perspective of a few bubbles and crashes, along with all the emotions that go with them. It’s undeniable we’re in the very early days — the command-line times — of an AI era, and though it will probably have its own bubble and crash cycles, it feels as significant to me as anything since we started. It’s more important than ever that we fight for open source and the freedom-enhancing side of technology. I’m committed to doing whatever I can to democratize publishing, commerce, and messaging, but there are many other areas of the human experience to cover… pick one to work on! It’s hard and rewarding work.

When I was working on an early version of one of our internal stats systems, it was really important to me that it showed rolling windows of the last 24 hours (daily), 168 hours, 4 weeks, and of course yearly. The rolling was important so you could see the impact of your changes as soon as possible. Then I felt called to add another: decade.

Some thought it was silly at the time, and it’s true that it initially served mainly as a way to display the cumulative number. But I wanted every time someone looked at one of these stats pages that they were reminded that we’re building for the long term. Our users and customers deserve nothing less. And now we have some statistics with 20 years of history, it has some useful comparisons as well!

In Ten Years of Automattic, I wrote:

There’s a lot more to do, and I can’t wait to see what a “20 Years of Automattic” post says. I’m a lucky guy.

Now we know! I’m still a very lucky guy, and can’t wait to build, learn, and share alongside a talented crew of like-minded hackers, dreamers, and doers.

* I’ll note that pioneers like Bob Young (Red Hat), Stephen Wolfram (Wolfram Research), Jason Fried (37Signals), and Mårten Mickos (MySQL) were big inspirations. Also, the entire Open Source community and most projects operated at least partially this way, which is why it seemed so natural to us as a second-generation Open Source company.

Play With Clay

Happy to announce that the amazing Clay.earth product and team is joining Automattic. If you haven’t tried the app out yet, here’s a quick video to give you a taste.

TechCrunch has covered the broader strategy pretty well: One of the top requests we’ve heard from Beeper beta testers is they want to tie in more context, like a personal CRM, and some even requested Clay by name. We’ll keep the apps separate, as Clay also has some interesting team uses, but they will complement and integrate with each other as part of our all-in-one messaging strategy.

We share a vision to integrate Clay’s technology, which manages over 140 million relationships, as a layer across many of our products and experiences at Automattic. I’m excited to work with the founders, Matt and Zach, to bring this vision to life. I’ve always felt the missing primitive in WordPress’ content management data architecture was a scalable concept of a Person and Relationships outside of our user table.

Here’s the beautiful announcement on the Clay site and on Automattic’s.

Remember Gravatar?

Gravatar has always been about giving people control over their identity online. One avatar, one profile, synced across the web, verified connections, with a fully open API.

Gravatar is a true open identity layer for the internet, and now for AI

For developers, we’ve rolled out mobile SDKs and a revamped REST API that lets you fetch avatars and profile data with just an email hash. Whether you’re building a blog, a community, or an AI agent that needs to understand who it’s talking to, Gravatar provides the infrastructure to make identity seamless and user-centric. 

It’s free, open, and built with developers in mind. We believe identity should belong to the individual, not be locked behind proprietary platforms. Gravatar is our contribution to that vision.​

If you haven’t checked it out lately, now’s a great time to explore what Gravatar can do for your app or your online presence. And think about how your apps can drive more Gravatar signups.

Berkshire Hathaway Meeting

I’ve checked off a bucket list item: I’m attending a Berkshire Hathaway shareholder meeting. It’s really an event! Thousands flock to Omaha, Nebraska, for the legendary Q&A sessions with Warren Buffett and shareholder deals. They’ve made it quite the circus, with every Berkshire Hathaway company having a booth of some sort, and typically selling their goods at a discount or with exclusive items you can only buy there, like Warren Buffett and Charlie Munger Squishmallows (which of course I got, to complement my bronze busts).

It’s strange to have a Dairy Queen booth selling $1 ice cream (cash only!) next to NetJets, but those juxtapositions are part of the Berkshire vibe—it’s very high/low, like Costco (a big Berkshire holding). There’s also an element of WordCamps or a Salesforce Trailblazer event in that you can tell there’s a “type” of person that’s easy to spot who’s a Berkshire enthusiast. A lot of Berkshire brands are also WordPress users: Duracell, GEICO, Acme Brick, Berxi, MiTek. I think there is a lot of mimetic overlap between the values of open source and the values of building a Berkshire company.

As with any big gathering, the side events are also great, and I was honored to have a fireside chat with a friend and Buffett protégé, Tracy Britt Cool. To an audience of about 60+ CEOs in the Kanbrick community, we talked about Automattic’s history and some of the latest happenings in tech; AI was definitely on people’s minds in the Q&A. They had questions for me, but I also feel like I have a ton to learn from this group that has built founder or family-owned businesses with an average of 80-100M of revenue, the kind of thing that is the engine of the American economy.

It makes me pine for the day when we can have more shareholders in Automattic; I think it would be an amazing cohort of folks that believe in open source and the open web, invested together and learning from each other, and I could imagine an event very much like these shareholder meetings. It’s so much more powerful when you build a business where your customers are also a community.

Update: I knew this would be a special one because it was Warren’s 60th, but he really went above and beyond by announcing his intention for Greg Abel to take over as CEO at the end of the year. The standing ovation was a special moment, 60 years of 19.9% compounding returns! I think the future of Berkshire is very bright because he’s shared so much of his worldview that there are others that have made it their own.

Automattic Operating System

I was interviewed by Inc magazine for almost two hours where we covered a lot of great topics for entrepreneurs but almost none of it made it into the weird hit piece they published, however since both the journalist and I had recording of the interview I’ve decided to adapt some parts of it into a series of blog posts, think of it as the Inc Article That Could Have Been. This bit talks about some of the meta-work that myself and the Bridge team at Automattic do.

At Automattic, the most important product I work on is the company itself. I’ve started referring to it as the “Automattic Operating System.” Not in the technical sense like Linux, but the meta layer the company runs on. The company isn’t WordPress.com or Beeper or Pocket Casts or any one thing. I’m responsible for the culture of the people who build those things, building the things that build those things. It’s our hiring, our HR processes, our expenses, the onboarding docs; it’s all of the details that make up the employee experience — all the stuff that shapes every employee’s day-to-day experience.

Take expense reports. If you’ve got to spend two hours taking pictures of receipts and something like that, that’s a waste of time. You’re not helping a customer there. We switched to a system where everyone just gets a credit card. It does all the reporting and accounting stuff automatically. You just swipe the card and it just automatically files an expense report. Sometimes there’s an exception and you have to work with the accounting rules, but it just works and automates the whole process most of the time.

Another commonly overlooked detail is the offer letter. We think so much about the design of our websites and our products. We have designers work on that and we put a lot of care and thought into it. But I realized we didn’t have the same attention to detail on our offer letter. When you think about it, getting an offer letter from a company and deciding to take it is a major life decision, something you only do a handful of times in your life.  This is one of the things that determines your life path. Our offer letter was just made by attorneys and HR. No designer had looked at it right. We hadn’t really thought about it from a product experience point of view. And so it was just this, generic document with bad typography and not great design. But it’s important, so one of the things we did was redesign it. Now it has a nice letterhead, great typography, and it’s designed for the end user.

I realized that the salary and stuff was buried in paragraph two. It was just a small thing in the document! Well, what’s key when you’re deciding whether to take a job? Start date, salary, you know, that sort of thing, so we put the important parts at the very top.

And then there’s the legal language. All the legal stuff, which is different in every country. We have people in 90 countries, so there’s all the legal stuff that goes in there. And then it has this nudge inspired by the behavioral economics book, Predictably Irrational.

There’s the story about how, if you have an ethics statement above where you sign the test or something, people cheat less. So I thought, well, what’s our equivalent of that? We have the Automattic Creed. It’s an important part of our culture. So we put the creed in, it says

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.

It’s not legally binding, but it’s written in the first person, you read it and you kind of identify with it and then you sign below that. We want people who work at the company who identify with our core values and our core values really are in the creed.

These sorts of things are key to our culture. And they’re universal. Again, we have people from over 90 countries. These are very different cultures, yes, and very different historical backgrounds and cultural makeups. But what’s universal? We have our philosophies that we apply every day regardless of where you were born or where you work.

DrupalCon Singapore

This week, DrupalCon Singapore is bringing together an incredible community of Drupal platform creators, developers, and supporters. 

Last year, I had the chance to share the stage with Dries Buytaert, the founder of Drupal, and the conversation stuck with me. It highlighted the profound impact we can have when communities like ours come together to push the boundaries of Open Source and shape the future of the web.

At Automattic, we believe that Open Source is more than a license—it’s a philosophy that drives innovation and makes publishing accessible to all, and we want to support fellow open source communities. Our team is at DrupalCon to share some of the tools we’ve built, including Akismet (check out the Drupal extension here), The Atavist Magazine, Beeper, Day One, Longreads, and Pocket Casts. These products, much like the web itself, thrive on connection and collaboration. (Basically all our non-WP stuff.)

I’ve loved hearing about how people are engaging with our booth—whether exploring our tools, grabbing a local snack, or taking a moment to recharge. For those of you at the event, I encourage you to swing by the Automattic booth, meet our team, and share your thoughts. Together, we can continue to create an open web that’s full of possibilities.

Welcoming Harper

As announced by Automattic and covered by TechCrunch, I want to take a moment to welcome Elijah Potter and Harper to join Automattic. Harper is a super-fast (way faster than LanguageTool and Grammarly), local English grammar checker. The technology is nascent, but I’m very excited to embed this throughout all of Automattic’s products, and then expanding it to other languages, all in an open source way that can be embedded everywhere. I’m a huge fan of Grammarly and use it every day, but I think we’re doing too much in the cloud right now and there is so much compute and potential at the edge, and I’m excited to drive that forward with projects like Harper, Gutenberg, and Playground.

Response to DHH

I’ve taken this post down. I’ve been attacked so much the past few days; the most vicious, personal, hateful words poisoned my brain, and the original version of this post was mean. I am so sorry. I shouldn’t let this stuff get to me, but it clearly did, and I took it out on DHH, who, while I disagree with him on several points, isn’t the actual villain in this story: it’s WP Engine and Silver Lake.

A few bullets to his core points:

  • The headline “Automattic is doing open source dirty” is not fair.
  • Automattic did not work on a deal with WP Engine for 18+ months because of the GPL, or them using “WP” in their name, it was because of their abuse of the WordPress and WooCommerce trademarks. Trademarks must be protected, as evidenced by Rails trademark policy.
  • Our C&D is about public trademark abuse; theirs is about censorship, and doxxes private messages. They have since filed a kitchen sink lawsuit that embroils all of WordPress.org.
  • Updating ACF to Secure Custom Fields in our directory was to provide users of our plugin directory the best, safest, most secure code. It included a security update that still has not been merged by the ACF team.
  • We will merge any improvements ACF makes to their GPL code going forward and will also include enhanced functionality in the coming days to provide a secure and free drop-in replacement for ACF. If WP Engine didn’t want this to happen, they should not have published their code under the GPL or distributed it through WordPress.org’s directory.
  • I think it’s fantastic when businesses are built on open source, the WordPress ecosystem is at least 10B+ a year; Automattic and WP Engine are less than 5% of that.