All posts by Matt

A master in the art of living draws no sharp distinction between his work and his play; his labor and his leisure; his mind and his body; his education and his recreation. He hardly knows which is which. He simply pursues his vision of excellence through whatever he is doing, and leaves others to determine whether he is working or playing. To himself, he always appears to be doing both.

Lawrence Pearsall Jacks in Education through Recreation, 1932

Automattic’s First New Board Member: General Ann Dunwoody

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!

I’m a huge fan of Mailchimp, but dang does the service get abused by folks aggressively opting you into mailing lists. I have a very early, very generic Gmail address that people put as a filler address into every possible service and it gets tens of thousands of list and spam mails. A good trick to find and unsubscribe from all the Mailchimp lists you’re on is to search for mcsv.net and then select all, report as spam, and unsubscribe. Gmail doesn’t deal well when the unsubscribe list is taller than your screen, so you may need to hit command + - a few times to make it all fit. Also according to this post, “you can also get in touch with our compliance team directly at compliance@mailchimp.com with the email address you would like to remove from all lists and they will be happy to further assist you there as well.” I will try that as well.

Atavist & Automattic

As reported by the Wall Street Journal, and an interview about on the WP.com blog, Automattic has acquired the Atavist platform, magazine, and team. Looking forward to working alongside the team: we’re keeping the magazine going and it’ll complement Longreads, and integrating the best of the platform’s CMS and publisher features into WordPress.com and Jetpack and after that’s done providing an upgrade path so all of its publishers can move to being WordPress-powered.

I really love this thread and the replies sharing stories about Val Vesa’s experience talking about WordPress in an Uber / Lyft ride:

As the traveller who has once been from home is wiser than he who has never left his own doorstep, so a knowledge of one other culture should sharpen our ability to scrutinize more steadily, to appreciate more lovingly, our own.

Margaret Mead

WordPress at 15

This weekend, May 27, marks the 15th anniversary of the first release of WordPress. It is an understatement to say that I am immensely proud of what this global community has become, and what it has created. More than 30% of the top sites on the web are now powered by WordPress, I’m writing this in our next-generation editor Gutenberg, and every day I meet someone who is building something interesting on WordPress or pushing our shared project in bold new directions. If you can believe it, growth has actually been accelerating.

There’s so much: A group of high school students bands together to build a national movement on WordPress; a president builds the foundation for his own next chapter on WordPress; the current WhiteHouse.gov switches over; or when someone like Hajj Flemings brings thousands of small businesses onto the open web for the first time, with WordPress.

To celebrate #WP15, hundreds of local WordPress communities around the world will be throwing parties. Go here to find a meetup in your area.

I am thankful to Mike for helping make WordPress a reality, many dedicated folks in the years since, and to all of you who are dreaming up the next 15 years. 😄

Many in the open source world are like Moses in that they speak of the Promised Land but will never set foot there. If I spend the rest of my life working and we don’t reach almost all websites being powered by open source and the web being substantially open, I will die content because I already see younger generations picking up the banner.

Elif Batuman, who was recently a Pulitzer finalist for her novel The Idiot, has a stunning story in the New Yorker on Japan’s Rent-a-Family Industry, “People who are short on relatives can hire a husband, a mother, a grandson. The resulting relationships can be more real than you’d expect.”

You think from the title it’s going to be one of those gee-whiz stories or vaguely condescending toward Japanese, but what follows is actually an incredibly poignant and powerful view of society through a lens I had never imagined before. It’s a #longread but I hope you take the time to sit with it this weekend. You may need a swordsman.

From Bertrand Russell’s A Conquest of Happiness.

It is very singular how little men seem to realize that they are not caught in the grip of a mechanism from which there is no escape, but that the treadmill is one upon which they remain merely because they have not noticed that it fails to take them up to a higher level.

He also says later, “There are two motives for reading a book: one, that you enjoy it; the other, that you can boast about it.” 😂

Goose-down Nape

There was a beautiful poem by Kayo Chingonyi in the New York Magazine this week titled The Nod:

When we’re strangers that pass each other
in the street, it will come down to this tilt
of the head — acknowledging another
version of events set in a new-build
years from now, a mess of a place filled
with books and records, our kids thick as thieves
redefining all notions of mischief.

Perhaps our paths will cross in a city
of seven hills as the light draws your face
out from the bliss of anonymity.
Maybe you’ll be stroking the goose-down nape
of a small child with eyes the exact shade
of those I met across a room at the start
of this pain-in-the-heart, this febrile dance.

When I hear "seven hills" my mind immediately goes to Rome, then San Francisco, but Wikipedia has a helpful list of cities that claim to be built on seven hills.

A friend pointed out The Nod is a fine complement to The Invitation by Oriah Mountain Dreamer.

On Automattic's internal BuddyPress-powered company directory, we allow people to fill out a field saying how far their previous daily commute was. 509 people have filled that out so far, and they are saving 12,324 kilometers of travel every work day. Wow!

No Office Workstyle

Reed Albergotti has a great article titled Latest Amenity for Startups: No Office. You can put in your email to read I believe but it's behind a paywall otherwise. The Information is a pretty excellent site that alongside (former Automattician) Ben Thompson's Stratechery I recommend subscribing to. Here are some quotes from the parts of the article that quote me or talk about Automattic:

So it’s no coincidence that one of the first companies to operate with a distributed workforce has roots in the open source movement. Automattic, the company behind open source software tools like WordPress, was founded in 2005 and has always allowed its employees to work from anywhere. The company’s 680 employees are based in 63 countries and speak 79 languages. Last year, it closed its San Francisco office, a converted warehouse — because so few employees were using it. It still has a few coworking spaces scattered around the globe.

Matt Mullenweg, Automattic’s founder and CEO, said that when the company first started, its employees communicated via IRC, an early form of instant messaging. Now it uses a whole host of software that’s tailor-made for remote work, and as the technology evolves, Automattic adopts what they need.

Mr. Mullenweg said Automattic only started having regular meetings, for instance, after it started using Zoom, a video conferencing tool that works even on slow internet connections.

He’s become a proponent of office-less companies and shares what he’s learned with other founders who are attempting it. Mr. Mullenweg said he believes the distributed approach has led to employees who are even more loyal to the company and that his employees especially appreciate that they don’t need to spend a chunk of their day on a commute.

“Our retention is off the charts,” he said.

And:

“Where it goes wrong is if they don’t have a strong network outside of work—they can become isolated and fall into bad habits,” Mr. Mullenweg said. He said he encourages employees to join groups, play sports and have friends outside of work. That kind of thing wouldn’t be a risk at big tech companies, where employees are encouraged to socialize and spend a lot of time with colleagues.

But for those who ask him about the negatives, Mr. Mullenweg offers anecdotal proof of a workaround.

For example, he said he has 14 employees in Seattle who wanted to beat the isolation by meeting up for work once a week. So they found a local bar that didn’t open until 5 p.m., pooled together the $250 per month co-working stipends that Automattic provides and convinced the bar’s owner to let them rent out the place every Friday.

They didn't need to pool all their co-working allowance to get the bar, I recall it was pretty cheap! Finally:

For Automattic, flying 700 employees to places like Whistler, British Columbia or Orlando, Florida, has turned into a seven-figure expense.

“I used to joke that we save it on office space and blow it on travel. But the reality is that in-person is really important. That’s a worthwhile investment,” Mr. Mullenweg said.It might take a while, but some people are convinced that a distributed workforce is the way of the future.

“Facebook is never going to work like this. Google is never going to work like this. But whatever replaces them will look more like a distributed company than a centralized one,” Mr. Mullenweg said.

Longreads was nominated today for its first-ever National Magazine Award, in the category of columns and commentary, alongside ESPN The Magazine, BuzzFeed News, Pitchfork, and New York magazine. Laurie Penny's Longreads columns explore important questions of consent and female desire that have strongly resonated in our current moment. In addition to this nomination, Penny's columns have been translated and republished in Italian and German newspapers, and will be collected in a forthcoming book.