MATT MULLENWEG: Howdy, howdy. Welcome to the Distributed podcast. I’m your host, Matt Mullenweg.
I got the chance to catch up with today’s guest, Stephen Wolfram, because my company Automattic invited him to give a talk at our annual company meetup in Orlando, Florida. This is a magical occasion where all 950+ Automatticians (which is what we call ourselves) get together to meet up face-to-face. This gives us an opportunity to hang out, break bread, and collaborate over the course of a few days. We also invite a number of speakers, smart people like Stephen.
For three decades, Wolfram Research has created and iterated on a suite of powerful computing technologies. Stephen Wolfram, who founded the company as a young science and math prodigy, started with a simple goal: “To build the tools to do what I wanted to do.” Today, Wolfram Research has more than 800 employees who continue to push its software forward.
Our host finds himself on the other side of the mic on the latest episode of The Rework Podcast. Basecamp co-founder David Heinemeier Hansson invited Matt for a friendly debate about tech monopolies, power in open-source communities, and how Matt views his role as the CEO of a successful company that contributes to the WordPress open-source project.
These are the words every new hire at Automattic sees on their first day, emblazoned across the company’s online handbook. They are designed not to instill fear, but to prepare the newly-minted Automattician for life in a fast-moving, globally-distributed company. Working at Automattic sometimes feels like chaos, but over 950 employees wouldn’t have it any other way.
Sonal Gupta is one of them. She describes the moment she first read those words. They gave her immediate comfort because they confirmed that yes, working in this environment can feel overwhelming, but she wasn’t alone.
MATT MULLENWEG: Howdy howdy. I’m Matt Mullenweg, the CEO of Automattic, and the co-founder of WordPress. Automattic is the company that makes WordPress.com and a bunch of other things. At Automattic we have a division called Other Bets, which encompasses a host of experimental projects that aren’t directly related to our core business. When we started thinking about this department, I knew we needed a renaissance person to lead it — with a background in legal, finance, and entrepreneurship, Sonal Gupta is just such a person.
Matt Mullenweg: I want for you to imagine that you’ve been hired as a manager at a scrappy startup where there are no meetings, no hierarchy — not even an office. How do you make people feel like they’re part of a team? How do you brainstorm, and how do you make sure the work’s getting done? Is it possible to cultivate a shared vision, structure, and goals by only meeting in person twice a year?
That’s what Scott Berkun faced nine years ago, when I hired him to join a little company called Automattic, which is the parent company of WordPress.com, which I founded in 2005.
Like any new employee, Scott Berkun had the jitters on his first day at Automattic. He was a little older than most of the people at the company, having spent the previous nine years at Microsoft. Although he witnessed firsthand the excitement of the tech giant’s glory days, office life was still rather conventional.
Now, in 2010, Scott was joining a young company with no offices, and — prior to his hiring — no managers. Before Scott joined, everyone in the company reported more or less directly to Automattic’s founder Matt Mullenweg and then-CEO Toni Schneider. Scott had been hired based on his own advice as an Automattic consultant. He had observed that the company had grown too large to operate efficiently with a flat structure. Scott suggested a turn toward a more conventional approach — the company needed hierarchy.
MATT MULLENWEG: There are all sorts of approaches to distributed work. Some people work from home or at a café in their neighborhood. Others are digital nomads. I’m Matt Mullenweg, the CEO of Automattic and co-founder of WordPress, and I travel around 300 days out of the year. I appreciate that I get to spend time with my family in Texas, but I love life on the road too, and being able to hang out with friends and colleagues all over the world, and meet WordPress users wherever they might be. One of the nice things about running a fully-distributed company is that even the CEO gets to be just as remote as everyone else.
Today’s guest is Cate Huston, who is a true digital nomad. All she needs is a cup of tea and a place to set up her laptop and she’s ready to go. Her home base is the city of Cork, in Ireland, but you’re just as likely to find her in any other corner of the globe.
The term “digital nomad” appeared in the ‘90s to describe an emerging class of globetrotting workers. The digital nomad in those days was an edgy, lone-wolf cyberpunk character with little dependence on hearth and home. Freed from the constraints of geography, the digital nomad hops from hotspot to hostel, client to client, living out of a suitcase and funding her lifestyle with contract work.
Cate Huston is the Head of Developer Experience at Automattic. She embodies the ethos of the modern digital nomad, and maintains a newsletter chronicling her travels. Though she calls the Irish city of Cork home, you’re as likely to find her in any other corner of the world. Yet Cate’s no lone wolf. Modern communication tools have made it possible for Cate to help manage and stay in constant contact with large teams. She’s deeply embedded within the Automattic organization, helping to define how its many engineers engage with stakeholders around the company — and with each other.