Can Matt Mullenweg save the internet?

Jan 19, 2023 8:01 PM

In the early days of the pandemic, Matt Mullenweg didn't move to a compound in Hawaii, bug out to a bunker in New Zealand or head to Miami and start shilling for crypto. No, in the early days of the pandemic, Mullenweg bought an RV. He drove it all over the country, bouncing between Houston and San Francisco and Jackson Hole with plenty of stops in national parks. In between, he started doing some tinkering.

The tinkering is a part-time gig: Most of Mullenweg’s time is spent as CEO of Automattic, one of the web’s largest platforms. It’s best known as the company that runs WordPress, the blogging platform that powers about 43% of the websites on the internet. Since WordPress is open-source software, no company technically owns it, but Automattic provides tools and services and oversees most of the WordPress-powered internet. It’s also the owner of the booming ecommerce platform WooCommerce, Day One, the analytics tool and the podcast app Pocket Casts. Oh, and Tumblr. And Simplenote. And many others. That makes Mullenweg one of the most powerful CEOs in tech, and one of the most important voices in the debate over the future of the internet.

But before we get to that, you have to hear about this RV. "I really love networking equipment," he said, in an effort to explain the story he’s about to tell. He's always been the guy who goes over to friends' houses and upgrades their router or just rewires the whole system: "So when I get this RV, what I ended up doing was I set up a multiple-cell phone modem router." It connects to all three major U.S. carriers and combines them into a single Wi-Fi network.

Suddenly, when Mullenweg signed on every morning to do his job as CEO of Automattic, one of the web's largest platforms and most powerful influences, he could do it from anywhere with a cell signal: like one time, last December, when he recorded a Web Summit panel from the side of Highway 97 in Northern California as logging trucks went by. Mullenweg, who is also an insatiable gearhead, had a solution for the truck noise, too: a Sennheiser headset mic with awesome noise-cancellation.

The setup is ever-changing. "What we recently figured out was how to mount a Starlink on top," Mullenweg said. His SpaceX-built satellite internet receiver plugs right in and provides even faster speeds. "You can't drive around with it, and I think it's geo-locked to just the Wyoming region," but with two minutes of setup his RV gets broadband-quality internet. "And," Mullenweg said, already planning his next upgrade, "SpaceX has announced they're going to do a mobile version, so whenever that comes, I'll redo the whole thing. It'll be nice not to have to mount and dismount, and it'll work when I'm moving."

From his always-connected RV, Mullenweg has continued to turn Automattic into a tech giant. He talks often about his desire to build "the Berkshire Hathaway of the internet," a holding company populated with the most ambitious and important products and services in tech. But there is one thing that binds the many products under the Automattic umbrella together: a bet on and belief in the open web and open-source software.

In every way that matters, Automattic is a reflection of Mullenweg (you could say he puts the “Matt” in Automattic). He started building web software because he wanted a place to store and share his photos; he’s a blogger to the core, and loves anything that aids in the free expression of ideas on the internet. He loves jazz, which is why WordPress releases are named for jazz musicians. He loves to read and write and work from anywhere, so he turned Automattic into a company that supports bloggers and promotes remote work. He buys companies that make products he likes, and companies that have missions he believes in. Most of all, he believes that open-source software is the future of everything. And he’s betting on it every way he can.

Eighteen years after he first started working on WordPress, Automattic is more powerful than ever. It’s a $7.5 billion company, one of the biggest private companies in the industry. And yet its founding idea — that software should be available to everyone and editable by anyone, that communities can build great things together, that walled gardens always eventually fall — seems more tenuous than ever. There’s another 17-year-old company named Facebook that flies in the face of everything Mullenweg believes in, and is threatening to own the future of the internet.

Most people will tell you it feels like the future of tech hangs in the balance. But the way Mullenweg sees it, open is still going to win. It's not a matter of if, only when. And all he's trying to do is help make it happen a little faster.

The builder

If you were in San Francisco in the early days of the Web2 era, circa 2005, there’s a good chance you have a Matt Mullenweg story. Maybe a 21-year-old Mullenweg personally upgraded your WordPress installation at one of his “upgrade parties,” which he used to throw at his San Francisco apartment. Maybe you went to one of his Christmas ugly sweater parties. Or maybe you went to one of the countless Meetup events, at which Mullenweg would extol the virtues of WordPress, open source and blogging.

Nearly everyone who knew Mullenweg in those days remembers the same three things: He looked like a kid, he was extremely nice and he had ridiculously big ideas. “WordPress, people knew,” said Scott Beale, the founder of Laughing Squid and a friend of Mullenweg since those early days. “And then you meet the guy, and it's like, he's so nice. No real ego, he’s ready to talk to anyone.”

“I had just started using WordPress,” said Om Malik, a blogger and venture capitalist, as well as a longtime friend and mentor to Mullenweg, “and I got in touch with Matt. I had no idea who he was, or how young he was at the time.” Malik would send Mullenweg long emails every time he ran into trouble with WordPress, and Mullenweg would always help. Eventually, “Matt and I just became friends,” Malik said. “We would talk about the internet, the open internet.” Even now, he added, “I only talk to him about technology. We never talk about business.”

Mullenweg had started WordPress two years earlier, alongside co-founder Mike Little, as a fork of software called b2/cafelog that Mullenweg noticed had been more or less abandoned by its creator. At that point, Mullenweg wasn’t trying to start a conglomerate; he was just trying to keep his blog online. He liked the idea that b2/cafelog was available through a General Public License, meaning anyone could fork and change the code and no one could take it away. “The work would never be lost,” Mullenweg wrote on his blog as he pondered making the move, “as if I fell [off] the face of the planet a year from now, whatever code I made would be free to the world, and if someone else wanted to pick it up they could.” A few months later, that fork had a name — WordPress — and was released to the public.

Even early on, Mullenweg used to tell people he wanted to work on WordPress for the rest of his career. He’d moved from Houston and taken a job at CNET in part because the company was going to pay him to work on WordPress, but as the platform took off he wanted to focus on it even more. But turning WordPress into a hard-charging, VC-backed startup designed for a nine-figure exit didn’t really interest him. “He said, ‘If I ever started a company, I’d want it to be a company that can be alongside the open-source project, and I’d want to work on it for decades,’” said Toni Schneider, a former Yahoo executive who eventually became the first CEO of Automattic. Schneider didn’t really take Mullenweg seriously for a while; who believes a 21-year-old kid when he tells you his plans for the rest of his life?

But Schneider quickly realized that Mullenweg really did see WordPress as his life’s work: in part because he found it interesting, knew it was a huge project and could see where it was headed, and in part because he saw WordPress as a tool through which to build a better internet. A better world, even. And he knew it might take a lifetime to pull it off.

The thinker

The first time Mullenweg and I spoke for this story, I asked him what he thought about the state of the tech industry. It was early September, and conversations were raging about antitrust, misinformation, surveillance capitalism, Big Tech’s overreach, Facebook’s effect on democracy and in general the society wrought by the tech industry.

Before he answered, Mullenweg changed the frame of the question. This happened constantly in our conversations: I’d ask about Instagram or the iPhone, he’d respond with Plato or Camus. Once, when I asked him about Facebook, he responded with a story about the printing press. In this case, he simply urged me to think more broadly. “I don’t think you have to limit yourself to looking at technology,” he said. “Zoom out to human history, or look at the current state of the world, and look at the tension and the pendulum swing between freedom and authoritarianism.” That back and forth has always existed, he said, and to expect a bunch of companies to suddenly fix it is unrealistic.

The cycle plays out the same in tech, he said. Take the internet: built as an open platform, eventually colonized by a handful of dictatorial players. To them, Mullenweg says: Congratulations on all your accomplishments, but you’ll lose in the end. “You get folks who want to ride that openness, but then close people off,” he said. “Like Facebook using your contact books or your email to bootstrap its growth, but then not allowing anyone to do the same on Facebook.” That can work, Mullenweg acknowledges. Sometimes really, really well. “But it also contains the seeds of its own demise.” Users inevitably begin to feel hemmed in and controlled by the closed platforms, and yearn for open pastures. Then they go build something better. Something open. “People's natural desire for freedom starts to get more and more of the best and brightest in the world working on open, distributed, decentralized systems.”

The seeds of this change are already everywhere, he said. Tesla has open-sourced its patents in an effort to speed up innovation in electric vehicles, because as Elon Musk said, the company’s goal is not just to sell cars but “to accelerate the advent of sustainable transport.” There’s also the whole decentralized, Web3, blockchain community, which excites Mullenweg every time it comes up. “There’s an inevitable gravitational pull towards open source affecting literally every field: finance, health, politics,” he said. “All the things that currently happen in closed ways, what if they were open? What if they were transparent? What if you could copy and paste it? Do your own version? Remix it?”

And then he offered the closest thing you’ll find to a Unified Theory of Matt Mullenweg. “As more and more of our lives start to be run and dictated by the technology we use, it's a human right to be able to see how that technology works and modify it. It’s as key to freedom as freedom of speech or freedom of religion. So that is what I plan to spend the rest of my life fighting for.”

In his mind, WordPress isn’t just a blogging platform, and Automattic isn’t just a startup. Both are also statements of purpose, proof points of a worldview that says that quarterly results and year-over-year growth aren’t the only metrics that matter. (And that if you wait long enough, open wins at those, too.) Mullenweg has long traded hype cycles for the arc of history. And he hopes he can help bend it a little.

The tycoon

Let’s fast-forward a few years from those early days of WordPress to more recent history. By now WordPress is a behemoth. About 43% of websites on the internet run on WordPress’ open-source platform, which is maintained by thousands of contributors. Meanwhile, Automattic is running a thriving business selling services around the software. WooCommerce, a WordPress plug-in that Automattic acquired in 2015, has become a particular success story: It’s an open competitor to tools like Shopify or the Amazon Marketplace, and has become one of Automattic’s main growth and revenue engines. There are countless businesses run on top of WordPress, from theme makers to plug-in developers to hugely successful publishers and retailers. Because Automattic sees what happens on the platform, and because that platform is so large, it’s in a unique place to make educated bets on the future of the internet.

Mullenweg became Automattic’s CEO in 2014, taking over the role from Schneider. Shortly thereafter, he launched the company into hyper-growth mode, and also got a crash course on how to run a business. “For me, the big transition was from coding every day to not coding every day,” he said. Schneider saw it the same way as he stepped down: “The product stuff kept going beautifully, but it took him a while to really ramp up on the business stuff and figure out: How do we organize this company in a way where each of these businesses can thrive?”

But as he often does, Mullenweg learned to think bigger. “My big learning under Toni was that by changing code, I can affect that part of the program,” he said. “But [by] changing people, you can affect the world.” He came to love thinking about the architecture of Automattic and how to build a company with the same ideals and incentives as the community it came from. To sum up his style, Mullenweg offered a quote from Antoine de Saint-Exupéry, the author of “The Little Prince.” (Because of course he did.) “He said, ‘If you want to build a ship, don’t drum up people to gather wood, divide the work and give orders. Instead, teach them to yearn for the vast and endless sea.’”

As Automattic has grown in size and scale, the company has more freedom to take on different kinds of projects. “I can build something from scratch with our 1,700 people,” Mullenweg said (Automattic's staff is actually closer to 1,900 now), “or we can partner with a company. We can make a minority investment, we can make a majority investment, we can make it a division of the company, we can make it fully integrated.” He said he’s always tried to keep Automattic nimble, ready to make big moves at the right moment but never conjuring a sense of panic or desperation.

There have been a few misses over the years: Automattic was one of Slack’s first customers but didn’t invest in the company, and WordPress was an early supporter of bitcoin but never held any of it. Now, Mullenweg said, he’s in a position to jump on almost anything, as long as it feels right. This year, in the midst of a huge uptick in M&A and fundraising around the industry, a lot has felt right: By Mullenweg's own count, Automattic acquired 42 companies and products in 2021, and even he's not sure that captures everything.

Over time, Automattic also gained a reputation as a good investor or acquirer in part because it doesn’t have rigid structures into which it needs to put things. “Every other company we talked to was telling us about their plans and what they wanted to do,” said Russell Ivanovic, the CPO of Pocket Casts, which Automattic acquired in July. Automattic was different. “They said, ‘Look, this is why we think you should join our company, this is the freedom you’re going to get, this is the kind of organizational structure that we have.’”

“Matt tends to attract people that are like him, who have that kind of product-led thesis and are a little bit more mission-driven,” said Deven Parekh, managing director at Insight Partners, which has invested several times in Automattic. “They aren't necessarily optimizing for the last dollar at the time they sell the company.” People like Paul Mayne, the founder of Day One, who said he wasn’t really looking for an exit but knew he’d be crazy to ignore Mullenweg’s advances. “It’s their openness,” he said when I asked why he thought Automattic was the right home for his company. “It’s all open source-based and long-term focused, and about writing and publishing. I felt like we shared values there.”

To truly be a platform, it has to be open. Otherwise it’s more like a trap.

There’s an underlying trend to many of Automattic’s recent acquisitions, a reflex to try to build or buy open alternatives to increasingly closed systems. As social media falls increasingly under Facebook’s watch, Automattic buys Tumblr; as Spotify moves to control more of the audio and podcast ecosystem, Automattic buys Pocket Casts. promises to be analytics minus the gross data practices; Day One promises top-notch encryption to keep your important memories and journal entries private forever. Every Automattic product is both a bet on the future and a subtle rebuke of the present.

“I think it’s crucially important to have alternatives that are creator-focused, versus advertiser-focused,” Mullenweg said. “I guess part of this is wanting alternatives to advertising business models as well.” That means betting on subscriptions, like Tumblr’s new Post+ service. It means making it easy for creators to sell things directly through WooCommerce. It means lots of other things, too, eventually.

And if that’s the plan, there are plenty of places left for Automattic to explore. “I would have loved to have Instapaper or Pocket,” Mullenweg said when the topic of reading apps came up. He’s a Pocket user now, and loves the app, but it’s owned by Mozilla. Which, of course, brings up the idea of web browsers; if you want to preserve user agency and power on the internet, the browser is a place to start. “I would be very, very interested in Mozilla,” Mullenweg said. “Or maybe, like, a Brave.”

For these new companies, joining Automattic can feel a bit like being dropped into Mullenweg’s frontal cortex. It’s a completely remote company, for one thing. And because Mullenweg is a blogger at heart, you’re likely to spend most of your first few days at the company reading. Automattic — like Mullenweg — defaults to transparency and flat hierarchies. Employees are encouraged to write about their ideas even in their very earliest stages, and everyone around the company is encouraged to comment. (That meant, for instance, that Pocket Casts’ Ivanovic could read back through chat logs to see the conversation that led to its acquisition, including the parts where some employees thought it was a bad idea.) It can feel strange at first, but multiple founders I spoke with said they quickly came to appreciate the Automattic way of doing things. “They have some internal document that just says, ‘embrace the chaos,’” Ivanovic said.

Mullenweg leads an executive team called “Bridge,” which operates as the connective tissue of the company. Most other teams are named after something random, like a bird or a mythological creature. The idea is for everyone to feel like they’re part of Automattic, not part of a company owned by Automattic. “It helps a team not be too attached to whatever they’re currently working on,” Mullenweg said. Ultimately, the mission matters most of all.

The titan

At this point, few companies have more influence over the way the internet works than Automattic. And few people not named Zuckerberg have more influence than Mullenweg. Beyond the whole “43% of the internet” thing, there’s the fact that both WordPress and Automattic basically belong to him. When Automattic sells shares to new investors, all the voting power goes back to Mullenweg. When he wants to push Automattic or WordPress in a new direction, he tries to do it as gently and collaboratively as possible, but one way or another he usually gets his way. Mullenweg generally tends to downplay this authority, noting that users can always fork WordPress and do their own thing, but there’s no question that where Mullenweg goes, the community — and the internet — follows.

In general, Mullenweg is hardly the chest-beating pundit type, but friends and foes alike describe a killer lying just under the surface. His vitriol has historically been reserved for those who violate the spirit of open software and open systems: He has, for instance, angry-blogged at website-builder Wix several times over the years, most recently responding to a Wix ad campaign by calling its locked-in business model “like a roach motel where you can check in but never check out.” Wix CEO Avishai Abrahami didn’t respond to a request for comment, but did write a blog post of his own refuting many of Mullenweg’s claims. (Years ago, in response to another angry Mullenweg post, he wrote another: “Wow, dude I did not even know we were fighting.”)

Anil Dash, the CEO of Glitch who used to run Six Apart and its blogging platform Movable Type, remembers Mullenweg capitalizing on every Six Apart mistake to grow WordPress. Dash said he doesn’t harbor a grudge, and in fact gives Mullenweg credit for having the right strategy at the right moment, but there’s one thing that nags at him. “I wish he’d had that energy for Zuck,” Dash said, “not the people he did.”

You could argue — and some do — that in this moment of reckoning over the effect of technology on our lives and society, Mullenweg should be a much louder force for good. He’s not shy about his beliefs, but he isn’t arguing for them in front of Congress. He could have slapped a “Facebook is bad” banner across every WordPress site on the internet, and he didn’t. He hasn’t been loudly shouting about Facebook’s misinformation problem or decrying Google’s data-collection systems. Even on the product side, WordPress is well-positioned to take on Substack, YouTube and so many others. Multiple people told me Automattic is leaving billions on the table, and should be doing more to produce and promote open alternatives to the internet’s most important tools.

Mullenweg's vitriol has historically been reserved for those who violate the spirit of open software and open systems. Photo: Arturo Olmos for Protocol

The tech industry right now is riddled with villains and short of heroes, and Mullenweg fits the bill nicely. He’s got the quiet alter-ego thing down pat. So where’s the super suit?

Mullenweg thinks about this for a minute. “I’m not sure where to start there.” Then, after a pause: “I do think you have to pick your battles, because you can’t fight all things at once.” He worries that changing Facebook and Google requires changing the ad-based business model of the internet, which is harder than it’s made out to be. But mostly, he thinks issues of data privacy and content moderation are big and complicated. “I have an appreciation for the challenge of moderation on Facebook,” he said. Yes, Facebook should be doing better. Of course. But Mullenweg seems more interested in solving problems than pointing fingers. “I really had to make a conscious effort to stay out of day-to-day things in the news,” he said, “just because there’s so much going on.”

There’s just no hurrying Mullenweg, it seems. Even as the tech industry swirls around him, with regulatory fights and social media backlashes and the seemingly hourly shift in priorities, Mullenweg remains steadily on course. “We aspire to create the layer that every other application on the web can run on,” he said. “Hopefully one day, 85% or 90% of all websites have WordPress as their base layer.” Right now, the web operates largely on top of closed platforms owned by companies like Amazon and Facebook. “But to truly be a platform,” Mullenweg said, “it has to be open. Otherwise it’s more like a trap.”

He plans to spend the rest of his career building the web’s one true platform, the open system the internet deserves. What exactly does that look like? Who knows. Mullenweg is increasingly fascinated by all things Web3 and crypto, and sees in that space much of the collaboration and community he loves about WordPress and open source in general. He proudly reminded me that WordPress began accepting bitcoin in 2012, and that Vitalik Buterin, who eventually created Ethereum, wrote about Automattic for Bitcoin Magazine the same year.

"To me, what Web3 embodies is two essential ideas: decentralization and individual ownership," Mullenweg said at his recent annual State of the Word speech, where he updates the WordPress community on the year that passed. He preceded that by saying he didn't really know how to define Web3 at the moment — who does, really? — but supported the belief in an internet that anyone can help build, tweak to fit their own needs, and own themselves without paying rent to some large tech giant. He did issue a warning, though: "For every project which is asking for your money, dollars, for you to pay the cost of a house for a picture of an ape, you should ask: Does it apply the same freedoms which WordPress itself does? How closely does it apply to increasing your freedom and agency in the world?"

The details do matter, to a point, but it’s not just about WordPress, and it’s definitely not just about Automattic. Those are just tools. For him, the lifelong work is about something much bigger than either one — bigger, even, than the tech industry.

After we hung up our first Zoom call, Mullenweg sent me an email with the subject line “Freedom is central.” The body was a quote from Albert Camus, which worked as an explanation for just about everything Mullenweg believes in, fights for and plans to spend the rest of his life working on: “The only way to deal with an unfree world is to become so absolutely free that your very existence is an act of rebellion.” The email was just that, Mullenweg’s name and three links to WordPress sites. What else do you need to know?