Category Archives: Automattic

Dance to Calypso

One of the hardest things to do in technology is disrupt yourself.

But we’re trying our darndest, and have some cool news to introduce today. When I took on the responsibility of CEO of Automattic January of last year, we faced two huge problems: our growth was constrained by lack of capital, and the technological foundations of the past decade weren’t strong enough for the demands of next one.

The first has a relatively straightforward answer. We found some fantastic partners, agreed on a fair price, issued new equity in the company to raise $160M, and started investing in areas we felt were high potential, like this year’s WooCommerce acquisition. This “war chest” gives us a huge array of options, especially given our fairly flat burn rate — we don’t need to raise money again to keep the company going, and any capital we raise in the future will be purely discretionary. (Since last May when the round happened we’ve only spent $3M of the investment on opex.)

The second is much harder to address. The WordPress codebase is actually incredible in many ways — the result of many thousands of people collaborating over 13 years — but some of WordPress’ greatest strengths were also holding it back.

The WordPress codebase contains a sea of institutional knowledge and countless bug fixes. It handles hundreds of edge cases. Integrates constant security improvements. Is coded to scale. Development moves at a fast clip, with six major releases over the past two years and more around the corner. Its power and flexibility is undeniable: WordPress just passed a huge milestone, and now powers 25% of the web. You can run it on a $5-a-month web host, or scale it up to serve billions of pageviews on one of the largest sites on the web,

The interface, however, has been a struggle. Many of us attempted to give it a reboot with the MP6 project and the version 3.8 release, but what that release made clear to me is that an incremental approach wouldn’t give us the improvements we needed, and that two of the things that helped make WordPress the strong, stable, powerful tool it is — backward compatibility and working without JavaScript — were actually holding it back.

The basic paradigms of wp-admin are largely the same as they were five years ago. Working within them had become limiting. The time seemed ripe for something new, something big… but if you’re going to break back compat, it needs to be for a really good reason. A 20x improvement, not a 2x. Most open source projects fade away rather than make evolutionary jumps.

So we asked ourselves a big question. What would we build if we were starting from scratch today, knowing all we’ve learned over the past 13 years of building WordPress? At the beginning of last year, we decided to start experimenting and see.

Today we’re announcing something brand new, a new approach to WordPress, and open sourcing the code behind it. The project, codenamed Calypso, is the culmination of more than 20 months of work by dozens of the most talented engineers and designers I’ve had the pleasure of working with (127 contributors with over 26,000 commits!).


Calypso is…

  • Incredibly fast. It’ll charm you.
  • Written purely in JavaScript, leveraging libraries like Node and React.
  • 100% API-powered. Those APIs are open, and now available to every developer in the world.
  • A great place to read, allowing you to follow sites across the web (even if they’re not using WordPress).
  • Social, with stats, likes, and notifications baked in.
  • Fully responsive. Make it small and put it in your sidebar, or go full-screen.
  • Really fun to write in, especially the drag-and-drop image uploads.
  • Fully multi-site for advanced users, so you can manage hundreds of WordPresses from one place.
  • Able to manage plugins and themes on Jetpack sites, including auto-upgrading them!
  • 100% open source, with all future development happening in the open.
  • Available for anyone to adapt to make their own, including building custom interfaces, distributions, or working with web services besides

A lot of people thought we should keep this proprietary, but throughout my life I’ve learned that the more you give away, the more you get back. We still have a ton to figure out around plugins, extensibility, contributions, Windows and Linux releases, API speed, localization, and harmonizing the API and WP-API so it can work with core WordPress. Thousands more PHP developers will need to become fluent with JavaScript to recreate their admin interfaces in this fashion. I’m also really excited to revisit and redesign many more screens now that we have this first version out the door.

This is a beginning, not an ending. (1.0 is the loneliest.) Better things are yet to come, as all of you dig in. Check out these links to read more about Calypso from different perpsectives:

This was a huge bet, incredibly risky, and difficult to execute, but it paid off. Like any disruption it is uncomfortable, and I’m sure will be controversial in some circles. What the team has accomplished in such a short time is amazing, and I’m incredibly proud of everyone who has contributed and will contribute in the future. This is the most exciting project I’ve been involved with in my career.

With core WordPress on the server and Calypso as a client I think we have a good chance to bring another 25% of the web onto open source, making the web a more open place, and people’s lives more free.

If you’re curious more about the before and after, what’s changed, here’s a chart:



Arthur C. Clarke on Distributed Work

I saw the new Steve Jobs movie a few days ago, which I enjoyed as a movie even though the main elements were fiction and it should have been titled something else.

But they had an awesome video interview with the amazing Arthur C. Clarke in 1974, which I’ve embedded above, where he said the following right around 0:56.

Interviewer: I wonder though, what sort of a life will it be in social terms if our whole life is built around the computer, if we become a computer-dependent society, computer-dependent individuals.

ACC: In some ways, but they’ll also enrich our society because it’ll make it possible for us to live anywhere we like. Any businessman, any executive could live almost anywhere on earth and still do his business through a device like this, and this is a wonderful thing, it means we won’t have to be stuck in cities, we can live out in the country or wherever we please, and still carry on complete interaction with human beings, as well as with other computers.

Wow, extremely prescient. Remember, this was 1974! The dominant technology companies of today still follow the same office-centric model as when computers took up entire rooms, but the dominant companies of tomorrow will be built and grow in a completely distributed fashion. (And of course, we’re hiring.)

See also, from 2012: Automattic, Forbes, and the Future of Work.

Ten Years of Automattic

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, 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, 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.


Woo & Automattic

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.

New Funding for Automattic

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, 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: Parent Automattic Has Raised $160 Million, Now Valued at $1.16 Billion Post-Money, on Techmeme, and on the Wall Street Journal.

Toni Schneider & Automattic CEO

Eight years and one day ago I blogged about Toni Schneider joining Automattic as CEO, as I said then:

I first met Toni shortly after I moved to San Francisco and I’ve wanted him to be a part of Automattic pretty much since the idea first entered my mind. We’ve spent many long meals over the past year discussing the Automattic idea before it even had a name. I’ve been on cloud nine since (somehow) I convinced him to leave the incredibly cushy corporate job and rough it out in startup world again. I’m very very excited about some of the things coming down the line.

Fast-forward roughly two thousand, nine hundred, and twenty-two days and I’m still on cloud nine and love working together with Toni. We have been through some incredible ups and downs in people, valuation, been on both sides of the table for acquisitions, and seen dozens of competitors come, go, and come again as the hyperactive tech news cycle loops back around.

Today we’re announcing publicly that Toni and I are switching jobs — he’s going to focus on some of Automattic’s new products, and I’m going to take on the role of CEO. Internally this isn’t a big change as our roles have always been quite fluid, and I’ve had some recent practice filling in for him for a few months last year when he was on sabbatical. I’ve learned a tremendous amount from Toni over the years and I’m looking forward to putting that into practice.

Besides, it’s obvious that no one in their twenties should run a company. They think they know everything, a fact I can now say with complete confidence now that I’m 30 and two days old.

See also: Toni Scheider’s post, Om Malik, Tony Conrad.