In February of this year, Automattic closed a new primary funding round of $288M, bringing in some great new partners including BlackRock, Wellington, Schonfeld, and Alta Park. Existing investors ICONIQ and Aglaé (Bernard Arnault) also participated. This round was common stock, and like all funding since 2011, included a proxy assigning me the right to vote the shares.
Automattic was very busy during this time frame, as we were working on what would become the Parse.ly, Day One, and Pocket Casts acquisitions, our investments in Element and Titan, plus more acquisitions and partnerships we haven’t announced yet, so we haven’t mentioned the February funding round until now. And while we are a bit surprised the fundraise did not leak to the press, it’s now been an awkwardly long time since February and I’m pleased to formally announce it now.
And since then, Automattic has continued to grow at a rapid pace and we recently took the opportunity to do a $250M share buyback at a $7.5B valuation that just closed last week. The buyback was primarily targeted at current and former employees.
We’ve grown and increased our valuation at a rate higher than most other alternate investments available to investors. However, some of Automattic’s employees and former employee shareholders have been part of our journey for a very long time. Selling a bit of their equity holdings could have a significant impact on their lives.
Automattic was founded 16 years ago and is still private, so it’s important for us to try to provide liquidity to any shareholder who wants it. We do the same with our internal A12 stock plan where we let our employees buy our shares and also offer an opportunity for all holders to sell them back to Automattic, every quarter. (I need to do a longer post on that.)
One interesting thing we’ve been doing in these buybacks is holding the shares as treasury stock within the company instead of canceling the shares at purchase. This allows us to buy shares that come onto the market, and then when an investor comes and wants to put a larger quantum of capital into the company, we can re-sell the treasury shares that the company bought earlier. In effect, we are providing both a sell-side and buy-side for Automattic stock, serving previous and new investors and making money on these trades since we bought and took the risk earlier. We’ve established a logical valuation methodology, which is based on a simple multiple of the last twelve month’s revenue, so shareholders can track and anticipate performance.
All of this has been a lot of fun and we’ve seen a great amount of success, but it’s not all smooth sailing; we still have our share of challenges, probably the biggest being hiring. We have significantly scaled up our ability to find and hire great folks, with 371 accepted offers already in 2021 and it’s only August. However, with the growth of WooCommerce (hiring a Head of Payments) and our enterprise business, WPVIP, in particular, we need to move faster to keep up with the opportunity. For me and many other of the most-tenured Automatticians within the company hiring is the top priority. To that end, I’m also looking for someone to partner with me and our top executive group (which we call Bridge) in Creative Talent Development, an executive recruiter to help craft the highest performing teams of executives for each of our businesses.
We have a multi-decade opportunity ahead of us to create the best solutions for the open web platform of WordPress, and WooCommerce is doing the same thing for commerce; growing together over the long-term with people passionate about the same mission is my favorite part of my job.
In it, I drew the distinction between “horizontally scaled” teams, in which physical offices are connected to remote workers via satellite (home or commercial) offices, and “fully distributed” teams where, as you said, “the creative center and soul of the organization on the internet, and not in an office.”
At Parse.ly, we’re only a couple years old but have been operating on the distributed team model, with ~13 fully distributed employees, and it’s working well. Always glad to hear stories about how Automattic has scaled it to 10X our size.
And, likewise, we blow some of our office space savings on camaraderie-building retreats; our most recent one was in New York, see [here] and [here.]
Very excited to share the news that Revue is joining Twitter. I’m a huge fan of the idea of better newsletters and Automattic was the largest investor in Revue. I’m looking forward to seeing what the very talented team will do as part of the Twitter network. Also many thanks to Kevin Kelly and Om for introducing me to Revue early on.
“We’ll never probably be the same. People who were reticent to work remotely will find that they really thrive that way. Managers who didn’t think they could manage teams that were remote will have a different perspective. I do think we won’t go back.”
Jennifer Christie, Twitter’s head of human resources, in BuzzFeed News
It has been a challenging time around the world—from how we live our daily lives to how we keep our kids safe in schools and our family members healthy in assisted living communities and hospitals.
And then there’s how we work. Seattle (and all of King County in Washington State) is encouraging companies to have their employees work from home. Given that Automattic is already distributed, we’re receiving requests from the press and other companies about how to navigate what is turning into a massive global work-from-home experiment.
It’s not ideal on any level. Even at a remote-friendly company like Automattic, we rely on in-person team meetups and conferences to strengthen our connections and get work done. For now, we’ve canceled all work-related travel.
But as the BuzzFeed story notes, this might also offer an opportunity for many companies to finally build a culture that allows long-overdue work flexibility. Millions of people will get the chance to experience days without long commutes, or the harsh inflexibility of not being able to stay close to home when a family member is sick.
Or even when you’re sick yourself. How many people in America go into an office even when they’re feeling under the weather, because of pressure from the company or managers, or because their sick days come out of their vacation days? This might be a chance for a great reset in terms of how we work.
For those asking for tips, my Distributed Podcast has a wealth of advice and stories about how we operate. But here are four good ones to start with:
Operate as if everyone works from different time zones, because one day they might. This means more communication, likely written, that is accessible to people even if they can’t attend a specific meeting or be in a specific place. If you can minimize the number of real-time meetings, do so. Embrace asynchronous communication.
If you are hosting a real-time meeting, improve the audio (and video) quality. Don’t use conference call lines with grainy phone audio. Sign up for Zoom, which allows for crystal clear audio calls or videoconference chats. Make video participation optional unless it’s planned well in advance. Record these calls so folks who can’t attend can catch up on what they missed. Everyone must use good headphones with mics (I love Sennheiser) to minimize external noise. Krisp.ai is also cool. Need a quiet place without distractions? Try a parked car or a closet.
We use our own WordPress blogs, called P2, instead of email as our central hub of communication so people throughout the company can access every team’s long-form notes, documents, and priorities. We’re bloggers by heart, so we blog a lot. There are other similar tools, like Basecamp. Make it your new office.
We also use Slack for real-time chat, social connection, and urgent conversations. Check out Matrix for an open-source, distributed version. Use it to chat and connect with your colleagues, but don’t let it replace your long-form planning notes in No. 3. Also create an etiquette that doesn’t force people to become chained to it all day and all night. When you ask a question in DM, do not expect that person to respond immediately, and ask your question upfront. Never write “got a sec?” and let it hang there. 😁
The truth is, there are a thousand ways to do remote work, but it starts with committing to it at all levels of the company. If you assume positive intent and place trust in your coworkers and employees—knowing that if they do great work in an office they can do great work anywhere—then you will all succeed.
Distributed work is becoming a reality for more companies. Automattic has been operating in a distributed-first fashion for more than 13 years now — we’re now up to more than 850 employees in 68 countries. But even in companies with physical offices, more employees are distributed around the globe and working together. Google just shared some fascinating stats about its work culture, with 100,000 employees working across 150 cities. Two out of five work groups have employees working from more than one location:
We’re a more connected world, so it makes sense that global business wouldn’t be confined to just one physical space. I often use Google as an example because I’ve been in meetings there where people were one building away from each other but still using video chat because of the time required to walk between meetings on their campus.
With that in mind, the team at Automattic has decided to start sharing our expertise and the technology that makes it all work. Introducing Happy Tools:
Our first product is Happy Schedule, which helps teams manage flexible schedules across time zones. Right now we’re rolling it out in a consultative way with just a few early customers to make sure the team can be totally responsive to their needs. We’re excited about this and other upcoming tools, because we believe that this is the future of work. We’re excited to have other companies give it a try.
Keep an eye on this space: There’s an entire suite of tools that make up the operating system of what has helped Automattic scale so effectively over the years. I’ve always believed it’s important to invest in your internal tools, and I’m excited to release more of them. If there’s something better in the market, we won’t release a tool for it—I’d rather use something external than have to build things ourselves—but where the industry still has a gap after such a long time, we’ll throw our hat into the ring.
It has over 130,000 views already! What I really love about this video in particular is that we get into the specifics of how a company can start to embrace a culture of letting employees work from anywhere, even if it started out as a traditional office with everyone in the same place. Automattic never started that way, so even as we’ve scaled up to more than 840 people in 68 countries, there’s never been a question — it’s now built in to our entire culture.
For distributed work to scale up, it’s going to require more CEOs, workers, and managers to test the waters. Any company can experiment with distributed work — just pick a day or two of the week in which everyone works from home, I suggest Tuesdays and Thursdays, then build the tools and systems to support it. Yes, that may require some shuffling of meetings, or more written documentation versus verbal real-time discussion. But I think companies will be surprised how quickly it will “just work.”
If the companies don’t experiment, workers may force them to do it anyway:
WordPress.com is partnering with Google and news industry leaders on a new platform for small- and medium-sized publishers, called Newspack. The team has raised $2.4 million in first-year funding from the Google News Initiative, Lenfest Journalism Institute, Civil funder ConsenSys, and the Knight Foundation, among others. We’re also still happy to talk to and engage other funders who want to get involved — I’d love to put even more resources into this.
It’s been a difficult climate for the news business, particularly at the local level. It also breaks my heart how much of their limited resources these organizations still sink into closed-source or dead-end technology. Open source is clearly the future, and if we do this right Newspack can be the technology choice that lasts with them through the decades, and hopefully our 15 years of growth lends some credibility to our orientation to build things for the long term.
The goal is to both make sure that the catalog of publishing tools as well as business tools they need to be able to run what one hopes is a sustainable news operation are addressed simultaneously. It’s not simply a CMS for a newsroom, but a full business system that enables publishing and monetization at the same time.
As you have come to expect from Automattic, everything will be open source and developed to the same standards WordPress itself is. We’re working with Spirited Media and the News Revenue Hub on the platform, and we will likely look for even more partnership opportunities from across the WordPress ecosystem. If you’d like to invest or get involved, drop us a line at email@example.com.
Update: On December 6th we released WordPress 5.0. It was definitely the most controversial release in a while, but the usage and adoption metrics are looking similar to previous releases. I’m looking forward to continuing to iterate on the new block editor!
We are nearing the release date for WordPress 5.0 and Gutenberg, one of the most important and exciting projects I’ve worked on in my 15 years with this community.
I knew we would be taking a big leap. But it’s a leap we need to take, and I think the end result is going to open up many new opportunities for everyone in the ecosystem, and for those being introduced to WordPress for the first time. It brings us closer to our mission of democratizing publishing for everyone.
I recently visited WordCamp Portland to talk about Gutenberg and WordPress 5.0, which will also include the new default theme Twenty Nineteen, which you’re seeing me test out on this very site. There were some great questions and testimonials about Gutenberg, so I’d urge you to watch the full video and read the WP Tavern recap. I’ve also visited meetups, responded to review threads, kept an eye on support, and I’m in the middle of office hours with the core community.
As we head toward the release date and WordCamp US, I’ve put many questions and answers into a Gutenberg FAQ below. For those who have other questions, I will be checking the comments here.
It’s an exciting time, and I’m thrilled to be working with y’all on this project.
What is Gutenberg?
Gutenberg, for those who aren’t actively following along, is a brand new Editor for WordPress — contributors have been working on it since January 2017 and it’s one of the most significant changes to WordPress in years. It’s built on the idea of using “blocks” to write and design posts and pages.
This will serve as the foundation for future improvements to WordPress, including blocks as a way not just to design posts and pages, but also entire sites.
The overall goal is to simplify the first-time user experience of WordPress — for those who are writing, editing, publishing, and designing web pages. The editing experience is intended to give users a better visual representation of what their post or page will look like when they hit publish. As I wrote in my post last year, “Users will finally be able to build the sites they see in their imaginations.”
Matías Ventura, team lead for Gutenberg, wrote an excellent post about the vision for Gutenberg, saying, “It’s an attempt to improve how users interact with their content in a fundamentally visual way, while at the same time giving developers the tools to create more fulfilling experiences for the people they are helping.”
Why do we need Gutenberg at all?
For many of us already in the WordPress community, it can be easy to forget the learning curve that exists for people being introduced to WordPress for the first time. Customizing themes, adding shortcodes, editing widgets and menus — there’s an entire language that one must learn behind the scenes in order to make a site or a post look like you want it to look.
The idea with blocks was to create a new common language across WordPress, a new way to connect users to plugins, and replace a number of older content types — things like shortcodes and widgets — that one had to be well-versed in the idiosyncrasies of WordPress to understand.
The block paradigm is not a new one — in fact many great plugins have already shown the promise of blocks with page design in WordPress. Elementor, one of the pioneers in this space, has now introduced a new collection of Gutenberg blocks to showcase what’s possible:
Why change the Editor?
The Editor is where most of the action happens in WordPress’s daily use, and it was a place where we could polish and perfect the block experience in a contained environment.
Additionally, the classic Editor was built primarily for text — articles have become increasingly multimedia, with social media embeds, maps, contact forms, photo collages, videos, and GIFs. It was time for a design paradigm that allowed us to move past the messy patchwork of shortcodes and text.
The Editor is just the start. In upcoming phases blocks will become a fundamental part of entire site templates and designs. It’s currently a struggle to use the Customizer and figure out how to edit sections like menus, headers, and footers. With blocks, people will be able to edit and manipulate everything on their site without having to understand where WordPress hides everything behind the scenes.
What does Automattic get out of this?
There have been posts recently asking questions about Automattic’s involvement in Gutenberg compared to other contributors and companies. There is no secret conspiracy here — as project lead I was able to enlist the help of dozens of my colleagues to contribute to this project, and I knew that a project of this size would require it. Automattic aims to have 5% of its people dedicated to WordPress community projects, which at its current size would be about 42 people full-time. The company is a bit behind that now (~35 full-time), and the company is growing a lot next year, so look for 10-15 additional people working on core and community projects.
In the end, Gutenberg is similar to many other open source projects — Automattic will benefit from it, but so will everyone else in the WordPress community (and even the Drupal community). It’s available for everyone under the GPL. If the goal was purely to benefit Automattic it would have been faster, easier, and created an advantage for Automattic to have Gutenberg just on WP.com. That wasn’t, and isn’t, the point.
Is Gutenberg ready?
Absolutely. Our original goal with Gutenberg was to get it on 100,000 sites to begin testing — it’s now already on more than 1 million sites, and it’s the fastest-growing plugin in WordPress history. There is a lot of user demand.
The goal was to both test Gutenberg on as many sites as possible before the 5.0 release, and also to encourage plugin developers to make sure their plugins and services will be ready. With everyone pitching in, we can make this the most anti-climactic release in WordPress history.
In the recent debate over Gutenberg readiness, I think it’s important to understand the difference between Gutenberg being ready code-wise (it is now), and whether the entire community is ready for Gutenberg.
It will take some time — we’ve had 15 years to polish and perfect core, after all — but the global WordPress community has some of the world’s most talented contributors and we can make it as good as we want to make it.
Someone described Gutenberg to me as “WordPress in 3D.” I like the sound of that. Blocks are like layers you can zoom in and out of. The question now is: What are we going to build with this new dimension?
Do I have to switch to Gutenberg when WordPress 5.0 is released?
Not at all. When it’s released, you get to choose what happens. You can install the Classic Editor plugin today and when 5.0 is released, nothing will change. We’ve commited to supporting and updating Classic Editor until 2022. If you’d like to install Gutenberg early, you can do that now too. The Classic Editor plugin has been available for 13 months now, and Gutenberg has been available for 18 months. Both have been heavily promoted since August 2018, and more than 1.3 million .org sites have opted-in already to either experience, so nothing will change for them when they update to 5.0.
How can I make sure I’m ready?
Before updating to 5.0, try out the Gutenberg plugin with your site to ensure it works with your existing plugins, and also to get comfortable with the new experience. Developers across the entire ecosystem are working hard to update their plugins, but your mileage and plugins may vary. And you can always use the Classic Editor to address any gaps.
As with every new thing, things might feel strange and new for a bit, but I’m confident once you start using it you’ll get comfy quickly and you won’t want to go back.
The release candidate of 5.0 is stable and fine to develop against and test.
When will 5.0 be released?
We have had a stable RC1, which stands for first release candidate, and about to do our second one. There is only currently one known blocker and it’s cosmetic. The stability and open issues in the release candidates thus far makes me optimistic we can release soon, but as before the primary driver will be the stability and quality of the underlying software. We made the mistake prior of announcing dates when lots of code was still changing, and had to delay because of regressions and bugs. Now that things aren’t changing, we’re approaching a time we can commit to a date soon.
Is it terrible to do a release in December?
Some people think so, some don’t. There have been 9 major WordPress releases in previous Decembers. December releases actually comprise 34% of our major releases in the past decade.
Can I set it up so only certain users get to use Gutenberg?
Yes, and soon. We’re going to be doing another update to the Classic Editor before the 5.0 release to give it a bit more fine-grained user control — we’ve heard requests for options that allow certain users or certain roles and post types to have Gutenberg while others have Classic Editor.
What happens after 5.0?
We’ve been doing a release of Gutenberg every two weeks, and 5.0 isn’t going to stop that. We’ll do minor release to 5.0 (5.0.1, 5.0.2) fortnightly, with occasional breaks, so if there’s feedback that comes in, we can address it quickly. Many of the previous bugs in updates were from juggling between updates in the plugin and core, now that Gutenberg is in core it’s much easier and safer to incrementally update.
What about Gutenberg and accessibility?
We’ve had some important discussions about accessibility over the past few weeks and I am grateful for those who have helped raise these questions in the community.
Accessibility has been core to WordPress from the very beginning. It’s part of why we started – the adoption of web standards and accessibility.
But where I think we fell down was with project management — specifically, we had a team of volunteers that felt like they were disconnected from the rapid development that was happening with Gutenberg. We need to improve that. In the future I don’t know if it makes sense to have accessibility as a separate kind of process from the core development. It needs to be integrated at every single stage.
Still, we’ve accomplished a lot, as Matías has written about. There have been more than 200 closed issues related to accessibility since the very beginning.
We’re also taking the opportunity to fix some things that have had poor accessibility in WordPress from the beginning. CodeMirror, which is a code editor for templates, is not accessible, so we have some parts of WordPress that we really need to work on to make better.
Speaking of which, CodeMirror was seeking funding for their next version — Automattic has now sponsored that funding and in return it will be made available under the GPL, and that the next version of CodeMirror will be fully accessible.
Finally, Automattic will be funding an accessibility study of WordPress, Gutenberg, and an evaluation of best practices across the web, to ensure WordPress is fully accessible and setting new standards for the web overall.
After WordPress 5.0, is the Gutenberg name going to stick around?
Sometimes code names can take on a life of their own. I think Gutenberg is still what we’ll call this project — it’s called that on GitHub, and you’re also seeing it adopted by other CMSes beyond WordPress — but for those outside the community I can see it simply being known as “the new WordPress editor.”
With the adoption of React for Gutenberg, what do you see as the future for React and WordPress?
The other beautiful thing is that because Gutenberg essentially allows for translation into many different formats — it can publish to your web page, it can publish your RSS feed, AMP, it can publish blocks that can be translated into email for newsletters — there’s so much in the structured nature of Gutenberg and the semantic HTML that it creates and the grammar that’s used to parse it, can enable for other applications.
And WordPress 5.0 is just the starting line. We want to get it to that place where it’s not just better than what we have today, but a world-class, web-defining experience. It’s what we want to create and what everyone deserves.
Was this post published with Gutenberg?
Of course. 😄 No bugs, but I do see lots of areas we can continue to improve and I’m excited to get to work on future iterations.
I recently returned from Orlando where Automattic hosted its annual Grand Meetup where nearly all of our 800 employees from around the world, spend a week together in the same place. (And yes, we’re hiring.)
Despite being a fully distributed company, I believe it’s still important to meet face-to-face — just not every day, in the same office. The Grand Meetup is our chance to get to know the people behind the Slack avatars and build relationships that can carry us through other 51 weeks of the year, when we’re working from more than 65 countries. It’s so much easier to hear the nuance in someone’s chat messages or p2 posts if you’ve hung out with them at Harry Potter World, or learned about their family, pets, and hobbies during a flash talk.
This year we were proud to welcome some incredible keynote speakers: Wild author Cheryl Strayed talking about creativity and writing; Automattic board member Gen. Ann Dunwoody, the first woman in U.S. Army history to achieve the four-star officer rank; Ari Meisel on delegating and automating your life; and Dan Harris, author of 10% Happier, on the panic attack that led him to embrace meditation and mindfulness.
As Automattic keeps growing we’ve been bringing in a lot of talented people behind the scenes to help expand on our vision as we go from hundreds to thousands of colleagues, and hundreds of millions to billions in revenue. Recently, former New York Times digital executive Kinsey Wilson joined our team as president of WordPress.com, the Chief Design Officer of Axios Alexis Lloyd has joined as head of Design Innovation, the former CEO of Bluehost James Grierson is leading Jetpack partnerships, and today I’m excited to announce a change to my bosses, the board of directors.
Gen. Ann Dunwoody served for 37 years in the U.S. Army, and she is the first woman in U.S. Military history to achieve a four-star officer rank. She’s also the author of A Higher Standard: Leadership Strategies from America’s First Female Four-Star General, a book I really loved and highly recommend. Automattic’s board has had no new members since its founding in 2005, so this is our first addition in 13 years. I became familiar with General Dunwoody’s work while researching distributed organizations outside of technology, which led me to the military, which led me to geek out on logistics, which led me to her book and eventually flying out to Florida to meet in person.
Below is a brief interview with Gen. Dunwoody — we chatted with her about global leadership, finding your passion, and building a business.
We’re excited to have you onboard, General Dunwoody. It’s interesting — at Automattic we like to point out that we’re all over the globe (over 740 employees in more than 60 countries) but you oversaw 69,000 military and civilians across 140 countries! Were there any big leadership lessons from managing operations across such a wide range of distances, timezones, and cultures?
That’s a great question. When I started out as a young officer in the Army, the leadership philosophy that was espoused back then was “Leadership by walking around.” When you’re in charge of a platoon, a company or even a battalion or Brigade that is not globally dispersed this philosophy is very sound. When you’re running a global organization with 69,000 folks in 140 countries, you have to leverage technology to keep real-time communications flowing and keep leaders updated. I would host (with the leadership) a global video teleconference every Wednesday connecting every organization from Afghanistan, Kuwait, Iraq, Europe, etc. and sites — hundreds across the United States. Our headquarters would provide an operational update and then we go around the globe to get update from from everyone — what’s going well, where they need help or additional resources. In the old days I think people believed information was power and often withheld information to use for personal advantage, but I believe shared information is power. By leveraging the power of the entire industrial base we could solve problems in real time. I still travelled around a lot to see our people, but it is not possible to keep everyone informed and in the loop with current operations without leveraging technology.
I love your answer about “shared information is power.” Did you ever find it difficult to break down the silos and embrace that concept?
Oh my, yes. They weren’t just silos, they were silos with concertina wire around them! Parochialism was rampant and everyone wanted their own system and own their own information. We had over 200 stand alone systems that didn’t talk to each other. So to field and design an enterprise IT system that leveraged systems with the needed information to support “foxhole to factory” was challenging and exciting.
And how did you decide what technological means to communicate an idea or a directive, versus, say, meeting in-person?
I would say it depended on the idea. If it was personal, probably a phone call (one on one); if trying to generate support for an idea or transformational concept, meet in-person with my initiatives group to socialize the idea and get their input modifications and buy-in. Then Commanders conference to socialize idea with them, as they will have to implement it. Once socialized with leadership, we worldwide videoconference with the entire organization to define and describe the purpose, intent, how, and why — so everyone knew what we were trying to do and what their role was in execution. I found you cannot over-communicate when trying to make changes.
It’s an incredible accomplishment to become the first woman in U.S. Military history to achieve the four-star officer rank. Can you tell me about how things changed (or maybe still need to change further) in terms of your experience during your 37 years of service, and how you addressed diversity and inclusion in the military?
First, I certainly didn’t accomplish this by myself — I had a lot of help along the way! I joined the Army as part of the Women’s Army Corps (WAC) back in 1975. A few years later they disestablished the WAC and began the integration of women into the regular Army. This was the first time women had the opportunity to have the same career opportunities as their male counterparts in the branches now open to women. The challenge for the women who came into the Army back then was to force the integration — fight being put into traditional jobs like being a secretary, admin, clerk, or cook — and fight to be platoon leaders, etc., to support and move the integration of women into the regular Army.
What I witnessed during my time in the Army was that the doors continued to open. Yes, there were roadblocks — but there were also many leaders along the way who were willing to help. I never worked for a woman. I worked for men who either believed in me or didn’t. My experience in my almost four decades was that the doors continued to open for women. I thought jumping out of airplanes was really neat — now my niece in the USAF is an A-10 fighter pilot, and we have women graduating from Ranger school!
On diversity, I realized that being the only female in many forums, my voice was hard to be heard. And I also realized that most folks promoted and surrounded themselves with people in their own image. What my philosophy was — and I still think it is an issue today — is that diversity is not about numbers, it’s about getting the best and brightest from all walks of life, to help leaders solve the very complex issues that face us today. Don’t surround yourself with only people that think or act or look like you.
Who are the leaders that inspire you today?
I think we are products of our past — Mom and Dad, even though not here on earth, gave me the values that still guide me. Many of my military mentors, Gen. Hugh Shelton, Gen. Pete Schoomaker, Gen. Gordon Sullivan, Gen. Dick Cody, are still coaches and mentors to me today.
Folks I admire: Warren Buffett, only met him once but I like his concern for the betterment of our country; Oprah Winfrey, although I have never met her I admire her for what she does for our country how she presents herself and how she handles herself — awesome; Gen. Mattis — wow, I admire him for taking on this extremely tough assignment for the good of our country and our defense. Secretary Gates served two administrations, Republican and Democrat.
People that inspire me are people I believe are true leaders — valuing honesty and having the best interests of the country at heart. No hubris!
Huge thanks to Judy Wert who led the search for the design role. Combined with Chris Taylor starting as Chief Marketing Officer at Automattic a few months ago I think we’re well-positioned to really boost the growth of WordPress in the coming years. You may have even started to see video ads for WP.com. We’ve had 90 people start so far this year at Automattic bringing our total to just under 500 in 50 countries, if you’d like to join the family we’re hiring for over a dozen roles.
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, WordPress.com.
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!).
Incredibly fast. It’ll charm you.
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 WordPress.com.
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:
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.)
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.
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.
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.
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.
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!
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.
But, even after my foray into Simplenote alternatives and doing research and trying out other note-taking apps, I’ve stuck with Simplenote as my iOS note-taking app of choice. […] However, I could consolidate them all into just one app if I had to. And that app would be Simplenote. The reason I’d choose Simplenote is because it’s a quick, easy-to-use app with great search and it has fast, reliable sync.
Go check it out. For me it was easy – even though I dropped Simplenote, I had kept NVAlt syncing with it in anticipation of an update as good as this one. I launched it, logged in and a few moments later I was back up and running. Best of all, Simplenote is back on my first home screen.
Simplenote has always kept the focus on content — your content. With a bare minimum chrome in its apps, Simplenote has stayed away from flashy gradients, big UI elements and detailed icons and instead, has offered a minimal, mostly white user interface to its users. I liked everything about Simplenote, so paying for its Premium subscription and supporting the service was a no brainer for me.
What is so compelling about Simplenote, and why exactly was it worth “reviving?”
From the day I first used Simplenote it felt like a breath of fresh air in a crowded sea of cluttered apps. I use and rely on the service every day. We do many things at Automattic, but our core passion is creating great products. When we see something we feel isn’t our best work it bugs us until we’re able to loop back and iterate on it — it’s a blessing and a curse. This latest iteration of Simplenote on Android, OS X, and iOS is something we’re all very excited about sharing with the world.
How big a role did Simplenote play in Automattic acquiring Simperium?
It depends on how you look at it: I probably would have never heard of Simperium if it wasn’t for Simplenote, and the app really demonstrates the power of the Simperium API and the tastefulness of the people who created it. But the bigger interest was in what we could build alongside Fred and Mike on top of Simperium across all our products.
Where do Simplenote and Simperium fit with Automattic? Will any of each service’s features make their way into your other products, like WordPress, or do you intend to operate them separately?
Simplenote and WordPress share one key characteristic: they’re about writing. They both aspire to become invisible and be a canvas for your creativity. WordPress has succeeded above its competitors year after year because we’re ruthlessly focused on the experience of the author, and I saw the same spirit in Simplenote. It fits in Automattic like a glove.
One of the keys of Simplenote is, well, its simplicity. I think as we integrate it more with the broader Automattic ecosystem it’ll look more like Simplenote inside of WordPress rather than vice versa. It’s all backed by an easy-to-integrate API so if people want something more complex someone will build a client for that.
Simperium is at the core of several new things we’re either building or hope to build in the near future. We’re investing quite a bit to make the service robust and flexible for our needs as a top-ten internet site, and that development will benefit everyone who uses the service much the same way our investment in anti-spam benefits the internet at large through Akismet. You will start to see the Simperium engine make its way into almost everything we do.
Will Simplenote someday be a fruitful business? If so, how?
The beauty of Simplenote being under Automattic’s wing is that we are already blessed with incredibly fruitful businesses in WordPress.com, Akismet, and VaultPress. The biggest thing I didn’t like about the old app was the ads, and as you’ve noticed those are gone in this new version. Our main goal is to pour our heart into something and make it great, then share it with the world. I find Simplenote indispensable, delightful, and use it every day, and I hope you will too.