Sara Rosso writes 10 Lessons from 4 Years Working Remotely at Automattic. (Lesson 11, left out: Always give list articles an odd number of items.)
Category Archives: Automattic
Extended Interview with Forbes
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
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
- Sunday, June 1: Seoul, South Korea
- Monday, June 2: Jakarta, Indonesia
- Wednesday, June 4: Singapore (info)
- Friday, June 6: Tokyo, Japan
- Saturday, June 7: Osaka, Japan
- Monday, June 9: Manila, Philippines
Australia & New Zealand
- Thursday, June 12: Melbourne
- Monday, June 16: Sydney
- Tuesday, June 17: Wellington
- Wednesday, June 18: Auckland
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
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
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.
Hiring By Audition Expanded
The guest blog on Automattic’s hiring process for the Harvard Business Review ended up being pretty popular and thanks to Michelle Weber and Dan McGinn it’s been expanded into a longer version that’s now on shelves in the actual magazine! Very excited about this. If you are in an airport and see it on the stands (as above) definitely pick it up, it’s a great issue.
Brad Stone at BusinessWeek reports Automattic has acquired the great service Longreads, which you can also read about on our blog. See also: Techmeme.
Gliding Over Seattle
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.
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?
Philosophical Conversation with Reid Hoffman
The chat I had the other week with Reid Hoffman is now online. Reid is such a thoughtful guy it’s my favorite interview in a while. We cover a lot of ground, including expanding WordPress’ (and Automattic’s) mission from “Democratize publishing” to “Democratize publishing and development.” Give it a watch!
WhatsApp Takeaway
For better or worse, a great deal of investment in technology is driven by pattern matching. In that world any company (including Automattic) that generally eschews hype, is largely subscription driven, and has a small number of employees relative to its audience should be thrilled at the 19 billion dollar acquisition of WhatsApp. The deal is incredible.
This has kicked off another round of pattern matching and halo effects, which are currently incredibly favorable but will evolve over the coming years based on how things go post-integration, just like the public perceptions of Geocities, Youtube, Doubleclick, Bebo, and Skype wildly shifted based largely on the press coverage over their latest traded value.
I’m thrilled with the outcome for WhatsApp and the manner in which they built their company, their product, and I hope they bring more of that thinking to Facebook, but I don’t think they should become a playbook any more than Instagram should inspire a no-revenue playbook. The pattern we should take away from this story is that there is no pattern. (In Perl, “there’s more than one way to do it” or Tim Toady.) As an entrepreneur making decisions for your company, always go back to your first principles of what’s important to you and why you started in the first place. As a journalist, try not to fit everyone into arcs you’ve seen before or ascribe value to previous coverage (or lack of coverage). As an investor try to evaluate every situation on its unique merits. Should founders be CEOs or not? Well, it depends on the founders, the company, and what it means to be CEO, not what an over-normalized sample of a few hundred companies did before in completely different contexts.
There are also products that succeed with design that seems childish or terrible on the surface (Myspace, eBay, Snapchat). A lot of what it comes down to is have you made something people want, and are they finding out about it from their friends. That’s often the realm people think of as marketing. The best marketers in the world don’t fit our preconceptions of what that word means because they’re in hoodies instead of suits and create environments and ecosystems rather than the traditional trappings of marketing.
Update: From @dsa, here’s a great follow-up read on Techcrunch: What Games Are: Flappy Bird, Patterns, And Context.
Bay Area Events

I have a few engagements in the coming week in the San Francisco area and online:
- Later today I’ll be on the WordPress-focused podcast Dradcast.
- This evening there will be a Patent Happy Hour co-hosted by Engine Advocacy, EFF, and Automattic.
- On Thursday the 20th I’ll be speaking with Kent Goldman as part of the First Round Capital Dorm Room Fund Speaker Series at Stanford Graduate School of Business.
- Friday the 21st I’ll be talking with Reid Hoffman as part of the LinkedIn Speaker Series at their campus, and it will also be broadcast online.
- Tuesday the 25th I’ll be on the WP Think Tank panel discussion with a number of other notable WordPress community members.
- On Wednesday the 26th I’ll be interviewing Ben Rattray of Change.org at the Commonwealth Club.
I spoke for about half an hour with Cameron Moll on his Hired podcast about working at Automattic and how we approach recruiting and hiring.
Paul Sieminski, the general counsel at Automattic (Automattlock), writes for Wired on how Corporations Abusing Copyright Laws Are Ruining the Web for Everyone.
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.
Matt 3.0
As in WordPress, the X.0 release is just the one that came after (X-1).9 before it, so while it seems more significant, it’s just another iteration in the steady march of progress, a job never done. I’ve now managed to stay alive for three decades, thirty rotations around the sun, and I woke up this morning a little hungover (there’s a lot of tequila in Mexico) but with a huge grin on my face.
In many ways life accumulates complexity as you get older, but the things that are most important are simple and universal: friends and loved ones, health, and working on something you enjoy and has an impact. I’m happier and finding balance more often than at any period I can remember since I was a young child.
This was another year in motion, traveling 345,211 miles to 78 cities in 13 countries. I’m still really enjoying being on the road, and it’s very intrinsic to how Automattic works, so I expect that to continue or even pick up pace.
Every generation feels this way, but it also genuinely seems like we’re at shift in how society works, with technology accelerating change, and navigating and more importantly creating that change is one of the most interesting challenges I can imagine working on.
Finally I’m humbled and amazed by the support for the charity: water campaign, which already is going to bring close to 2,000 people clean water.
Tomorrow I’ll wake up a little sunburnt, but hopefully with that same grin and ready to take on the years of my life that start with 3 and hopefully end with a bigger impact than my 20s had. It was a decade when I failed a lot, tried even more, and most importantly learned how to say yes and how to say no, something that gets easier as you learn about yourself.
All birthday posts: 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42.
Lean Startup Talk
I spoke with Sarah Millstein at the Lean Startup Conference earlier in the week. After a bit of intro we talk about how Automattic iterates, approaches hiring, and management.
Have you seen the famous Automattic / WordPress shuffleboard? That and more in this excellent profile and interview by Debra Winter in SOMA Magazine.
As written about by the Electronic Frontier Foundation and Techdirt, Automattic is fighting back against two cases where we feel the DMCA has been used abusively for censorship and bullying. Read more about it here.
Julie Bort at Business Insider writes How Automattic Grew Into A Startup Worth $1 Billion With No Email And No Office Workers. Includes a short interview with me at the end.