Category Archives: Automattic

The company behind WordPress.com, Tumblr, WooCommerce, Pocket Casts, Day One, Beeper, and more.

Ten Years of Automattic

Automattic, Personal

Ten years ago the first official Automattician was Donncha O Caoimh, and he had no idea what he was in for. Neither did I, honestly. And it’s been amazing.

I’ll remember the days before I knew everything.
— The Automattic Creed

When you think about it, Donncha was incredibly brave. WordPress had far less than 1% market share. I hadn’t joined Automattic yet — I was still working for CNET, paying Donncha with my salary, savings, and credit cards. He was leaving a Real Job for a Barely a Job; I hardly knew how to wire money to an international account to pay him. I’d just made a giant screw-up (probably my biggest ever), taking money to have spam advertising on WordPress.org, so I wasn’t the most confidence-inspiring leader.

It also seemed like the decks were stacked against us. We were going to try and build an open source business model different from what we had seen before, a hybrid of a downloadable open source project combined with a web service that ran the exact same software. Up to that point companies built on open source projects had usually suffocated the communities that spawned them.

Sign me up, right? But we had one important thing going for us: at our cores, we shared a deep belief that open source could transform any industry it touched and that web publishing needed to be democratized. We’d been hackers-in-arms together coding on WordPress, and knew we could take that and build on it.

I am more motivated by impact than money, and I know that Open Source is one of the most powerful ideas of our generation.
– The Automattic Creed

Within that first year we were joined by Andy, Ryan, Toni, and Mark, and together we began building a business which looks remarkably similar to what Automattic does today. (We’re all still at Automattic, by the way.)

We just want to make the web a better place. We’re proud to contribute to what I consider the best open source project in the world, WordPress. We bring it to as wide an audience as possible through hosting it on WordPress.com, and providing services for the ones we don’t host with tools like Jetpack. Through it all, we have fun and experiment with side projects that have become crucial to the ways we work — P2, Cloudup, Simplenote, and dozens more that we tried, failed, learned something from, and tried again.

Our work is far from finished, and I hope there are hundreds of failures we learn from over the next 20 years. One of the things that makes me happiest is that I get to wake up every morning and work on the hard problem of making the web a better and more open place, and I do it alongside close to 400 talented people at Automattic and thousands in the broader community. For me this is a life’s work. The first decade is merely the first chapter of what I hope to be a very long book, which will eventually tell the story of a movement and a company that are at the core of this crazy thing we call “the web.”

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.
— The Automattic Creed

Some find it strange that someone in this day and age would have the same job for a decade. The truth is, it’s not the same job: it’s always evolving. At times it’s been comfortable, at times it’s been extraordinarily challenging. I’ve needed to change how I work. Automattic has changed. The structure of the company is designed to accommodate growth, and we’re constantly experimenting with how we work and relate to one another.

Half the time I feel like we’re making it up as we go along — I’ve never managed a distributed company of 400 people before. But the important things stay the same: the desire for impact and my love for the people I work with. They embody the Automattic creed:

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.

Thank you, Donncha, for believing in me all those years ago and pioneering the way for a company that would come to impact a lot of the world. Thank you Andy, Ryan, Toni, and Mark. Thank you to every Automattician that’s made the same leap. We’re building something that gives people all over the world a voice and that people can trust to be thriving a century from now, and that’s huge.

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.

Update: Donncha has a post talking about starting at Automattic.

2025 Update: You no longer have to wait to see the 20 Years of Automattic post. 🙂

Woo & Automattic

Automattic, WordPress

For years, we’ve been working on democratizing publishing, and today more people have independent sites built on open source software than ever before in the history of the web. Now, we want to make it easy for anyone to sell online independently, without being locked into closed, centralized services — to enable freedom of livelihood along with freedom of expression.

It’s not a new idea: at a WordCamp a few years ago, someone stood up and asked me when we were going to make it as easy to create an online store as we’d made it to create a blog. Everyone applauded; there’s long been demand for better ecommerce functionality, but it’s been outside the scope of what Automattic could do well.

That changes today — drum roll — as WooCommerce joins the Automattic team to make it easier for people to sell online. Along with Woo’s announcement, here’s a short video explaining more:

In the past few years, WooCommerce really distinguished itself in its field. Just like WordPress as a whole, it developed a robust community around its software, and its products meet the needs of hundreds of thousands of people around the world.

Woo is also a team after Automattic’s own distributed heart: WooCommerce is created and supported by 55 people in 16 countries. Added to Automattic’s 325 people in 37 countries, that’s a combined 380-person company across 42 countries — the sun never sets.* I can’t wait to meet all my new colleagues.

Just like us, the vast majority of WooCommerce’s work is also open source and 100% GPL. And just like WordPress, you’ll find WooCommerce meetups popping up everywhere, from Los Angeles to London, and its global and community-focused work together to make the users’ experiences the best they can be.

ecomm-trends The stats are impressive: the WooCommerce plugin has over 7.5 million downloads and a million+ active installs; BuiltWith’s survey of ecommerce platforms shows Woo passing up Magento in the top million, with about triple the number of total sites. Even a conservative estimate that WooCommerce powers 650,000 storefronts means they’re enabling a huge number of independent sellers. They’ve added a tremendous amount to the WordPress ecosystem (alongside everyone else working in this area).

WordPress currently powers about 23% of the web. As we work our way toward 51%, WooCommerce joining Automattic is a big step opening WordPress up to an entirely new audience. I can’t wait to see how much more we can build together.

Automattic turns ten next month: another amazing milestone I couldn’t have imagined a decade ago. Today’s news is just the first of a number of announcements we have planned for the remainder of the year, so please stay tuned! There’s still so much work to do.

* Want to work with us? We’re hiring. Bonus points if you live in Antarctica, the only continent we don’t have covered.

As I said in the video, please drop any questions you might have in the comments and I’ll answer them as soon as I can. Also check out the posts from Mark and Magnus.

Read more: Mashable, Recode, Techcrunch, Venturebeat.

Five for the Future

Automattic, Design, Essays, WordPress

On Sunday at WordCamp Europe I got a question about how companies contribute back to WordPress, how they’re doing, and what companies should do more of.

First on the state of things: there are more companies genuinely and altruistically contributing to growing WordPress than ever before. In our ecosystem web hosts definitely make the most revenue and profits, and it’s been great to see them stepping up their game, but also the consultancies and agencies around WordPress have been pretty amazing about their people contributions, as demonstrated most recently by the fact the 4.0 and 4.1 release leads both hail from WP agencies (10up and Code for the People, respectively).

I think a good rule of thumb that will scale with the community as it continues to grow is that organizations that want to grow the WordPress pie (and not just their piece of it) should dedicate 5% of their people to working on something to do with core — be it development, documentation, security, support forums, theme reviews, training, testing, translation or whatever it might be that helps move WordPress mission forward.

Five percent doesn’t sound like much, but it adds up quickly. As of today Automattic is 277 people, which means we should have about 14 people contributing full-time. That’s a lot of people to not have on things that are more direct or obvious drivers of the business, and we’re not quite there today, but I’m working on it and hope Automattic can set a good example for this in the community. I think it’s just as hard for a 20-person organization to peel 1 person off.

It’s a big commitment, but I can’t think of a better long-term investment in the health of WordPress overall. I think it will look incredibly modest in hindsight. This ratio is probably the bare minimum for a sustainable ecosystem, avoiding the tragedy of the commons. I think the 5% rule is one that all open source projects and companies should follow, at least if they want to be vibrant a decade from now.

Further reading: There’s been a number of nice blog follow-ups. Post Status has a nice post on Contribution Culture. Ben Metcalf responded but I disagree with pretty much everything even though I’m glad he wrote it. Tony Perez wrote The Vision of Five and What it Means. Dries Buytaert, the founder of Drupal, pointed out his essay Scaling Open Source Communities which I think is really good.

Automattic Grand Meetup 2014

Automattic

Although Automattic is a fully distributed company with most people working from home in 197 cities around the world, we think it’s really important to meet in person as well and we bring the entire company together once a year. This year we went to Park City, Utah, and were blessed with amazing weather all week. We were right at the base of a mountain so there were beautiful trails for hikes and runs and gorgeous views no matter what direction you looked.

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There were all sorts of activities people did throughout the week from paintball to skydiving to a Magic: The Gathering tournament (I played for the first time in about 15 years) and morning running classes every day at 7 am. I went to a Crossfit class with about 15 colleagues. My body is sore but my heart is happy.

Myself and Joe

I’m really grateful that I get to work with the people I do, and on the problems that we work on together. It’s far from easy, in fact each year brings new challenges and I make mistakes as often as not, but it is worthwhile and incredibly fulfilling. A few hours ago I gave a closing toast and teared up looking around the room. So many folks that give their passion and dedicate themselves to jobs both large and small, visible and unseen, to help make the web a better place. A web that we want to live in. Here’s a vignette from when we were taking our annual family photo, it’s a goofy and crazy group of incredibly unique individuals that I hope to know and make things with for many decades to come.

Merchbar is an iPhone app that makes it easy to buy merchandise from your favorite artists. It also was the first investment I made through my Angellist Syndicate, and I’m excited for the team on its launch. (Although it’s good to remember that launching is a halfway point — you should expect to spend at least as much time as you did leading up to launch to get to something you’re happy with. Something I’m thinking about a lot in Automattic these days.)

Every second, somewhere in the world four babies and two WordPress blogs are born.

That great line comes from Shane Snow’s profile of myself, Automattic, and WordPress called “How Matt’s Machine Works.” If you’re interested in the latest on how Automattic works as seen from the eye of a journalist with a background in product and technology, check it out.

A few comments: Since it came out my colleagues have been making fun of me for “trolling.” 🙂 The term “benevolent dictator for life” goes back to at least 1995 and is common in open source communities. Our lounge in SF is now much nicer than the one pictured. We mostly use Slack instead of Skype. I would say my management style has changed quite a bit since when Scott was at the company. The end of the article nails it in that as Automattic has scaled, to 272 at latest count, it’s really the over 40 leads who keep things running as smoothly as they do, and many people in similar roles on the .org side.

Even with the above, the article is probably the best look at the things I’m involved with every day since 2009’s The Way I Work, so kudos to Shane and definitely check it out.

Extended Interview with Forbes

Automattic, Interview, WordPress

J. J. Colao, who covered Automattic for Forbes Magazine in 2012 and has a long history and experience with WordPress and Automattic, sat down with me for close to three hours in March and somehow managed to distill it down to just a few thousand words of interview. (“13,500 words down to 2,800.”) I’m sheepish to link it because there are a lot of “I” statements and some nuance lost in the distillation, but JJ asks great questions and we cover a lot of ground that anyone who follows Automattic or the WordPress ecosystem I think will find interesting. You can check it out here.

Seoul, Jakarta, Singapore, Tokyo, Osaka, Manila, Melbourne, Sydney, Wellington, and Auckland

Automattic, WordPress

Later this week I’m heading on a speaking tour of a number of cities in Asia, Australia, and New Zealand talking about the past and future of WordPress and some of the things I’ve learned in the past few years of building WordPress and Automattic. It’s been a number of years since I’ve visited these countries, and I’ve never been to Korea, Singapore, Melbourne, or Auckland before, so really looking forward to meeting the local communities in each of these cities and learning about how we can best set up WordPress for the coming decade of growth, especially in languages other than English.

If you’re near any of these cities and want to come by check out the following links for more information. Even if it says “sold out” already, as many are, put your name on the waitlist anyway because I know some places are already searching for larger venues, and there could always be cancellations or spaces open up at the last minute.

Asia

Australia & New Zealand

The schedule might be a little exhausting, but I wanted to make it as many communities as possible in the short window of time I have before I need to be stateside again.

New Funding for Automattic

Automattic, WordPress.com

I’ll start with the big stuff: Automattic is raising $160M, all primary, and it’s the first investment into the company since 2008. This is obviously a lot of money, especially considering everything we’ve done so far has been built on only about $12M of outside capital over the past 8 years. It was also only a year ago I said “Automattic is healthy, generating cash, and already growing as fast as it can so there’s no need for the company to raise money directly — we’re not capital constrained.”

I was wrong, but I didn’t realize it until I took on the CEO role in January. Things were and are going well, but there was an opportunity cost to how we were managing the company toward break-even, and we realized we could invest more into WordPress and our products to grow faster. Also our cash position wasn’t going to be terribly strong especially after a number of infrastructure and product investments this and last year. So part of my 100-day plan as CEO was to figure out what new funding could look like and we found a great set of partners who believe in our vision for how the web should be and how we can scale into the opportunity ahead of us, though it ended up taking 110 days until the first close. (Our other main areas of focus have been improving mobile, a new version of WP.com, and Jetpack.)

This Series C round was led by Deven Parekh of Insight Venture Partners, and included new investors Chris Sacca, Endurance, and a special vehicle True Ventures created to step up their investment, alongside our existing secondary investors from last year, Tiger and Iconiq. (There is a second close soon so this list might change a bit.) There was interest significantly above what we raised, but we focused in on finding the best partners and scaled it back to be the right amount of capital at the right valuation. Deven and Insight share our long term vision and are focused on building an enduring business, one that will thrive for decades to come.

WordPress is in a market as competitive as it has ever been, especially on the proprietary and closed side. I believe WordPress will win, first and foremost, because of its community — the hundreds of core developers and large commercial companies, the tens of thousands of plugin and theme developers, and the millions of people who build beautiful things with WordPress every day. Automattic is here to support that community and invest the full strength of our resources to making WordPress a better product every day, bringing us closer to our shared mission of democratizing publishing. But a majority of the web isn’t on an open platform yet, and we have a lot of work ahead of us. Back to it!

You can read more about the news by Kara and Liz on Recode: WordPress.com Parent Automattic Has Raised $160 Million, Now Valued at $1.16 Billion Post-Money, on Techmeme, and on the Wall Street Journal.

Scrollkit and Longreads at Automattic

Automattic, WordPress

You might have seen the news last week that Longreads is joining Automattic’s editorial team. Today I’m excited to announce that we’ve acquired Scroll Kit and they’re joining Automattic as well, and will be focused on making customization more visual and intuitive. We’re barely on the second inning of what WordPress could be, and the impact it can have on the world, and I consider myself very lucky to be working with the best and brightest on transforming the way the world publishes.

Gliding Over Seattle

Audrey, Automattic, Gallery

Chris Young of Chefsteps took me up in a glider while I was in Seattle and it was an amazing experience. There are some great organizations dedicated to it like the Soaring Society, and I’m planning on taking some lessons this summer, probably in the Tahoe area. The acrobatics were a blast, but my favorite was just the elegance of the more gentle flight, catching thermals and floating over the world with no engine and super-panoramic views. After gliding I met some fellow Automatticians for drinks, and Sam from Audrey.

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In April and May, there are Automattic team meetups and events happening in Budapest, Napa Valley, Pender Island, New Orleans, Barbados, Cardiff, Konstanz, Playa Del Carmen, Portland, Toronto, Saratoga Springs, Palermo, Edinburgh, and Lisbon. Did I mention that we’re hiring?