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.
Matt Mullenweg: Imagine starting a company with your buddy, turning it into a multibillion dollar business, and offering a service used by brands all over the world, and then walking away from it all to live in a monastery. That’s exactly what this week’s guest did. We’re going to hear all about why he did it. With the startup Buffer, Leo Widrich has achieved success by any measure. But something was missing. His dissatisfaction with the lifestyle led him to pursue deeper truths that he came to realize cannot be found in the pursuit of material success.
Leo studied Buddhism. He spent some time living with monks, and learned to appreciate an intentionally slow lifestyle. Now, he coaches entrepreneurs and even other coaches with the goal of helping them manage the stresses of their careers with a combination of ancient wisdom and a sprinkling of modern neuroscience. He wants people to learn how to build emotional resilience, and the ability to self-regulate their emotions so they can deal with their issues and avoid the full-scale burnout that he suffered.
When Buffer co-founder Leo Widrich reached his breaking point, his company was pulling in millions in annual revenue. He’d achieved his dreams of profitability and financial security, and he’d built a dedicated team working together toward a common goal. His team was distributed, a point of pride for the company. But Leo was lonely, unfulfilled, and felt ill-equipped to cope with the ups and downs of life.
MATT MULLENWEG: What did real-time remote collaboration look like 30 years ago, in the primitive era before Slack and Zoom? My guest on this episode of the Distributed podcast knows, because he was there.
Designer, author, and Automattician John Maeda spent the latter half of the 90s pioneering a new field called computational design at the MIT Media Lab, a legendary sandbox for researchers who wanted to explore and create the future of tech. Computational design was a bold new approach that applied design principles to the creation of hardware, software, and computer networks, and John helped define it from the beginning.
Design is visual and tactile. It plays with the form and function of objects and systems to improve them. It’s a discipline in which every undertaking is akin to getting together with a group of people and asking, “Look at what I made — what do you think? How can we make this better?”
Now, imagine this group of creators scattered all over the world. How can these collaborators find and maintain the spark of creativity that passes from one designer to another when they’re all hunched over a blueprint or marking up a whiteboard together? If anyone knows, it’s John Maeda.
When you supervise a team of engineers hailing from over 40 countries, the way Upwork’s Senior VP of Engineering Han Yuan does, you develop priceless knowledge about how distributed teams work. According to Han, the crux of the challenge is setting expectations with every team member. Doing this well requires maintaining a consistent culture, along with regular, frequent, and — most of all — clear communication.
What does it mean to maintain a consistent culture? Han calls this a “very difficult problem” when applied to distributed teams.
Upwork is the largest freelancing platform, operating across 180 countries. It’s a company that deals in human resources, so its own HR department needs to model best practices. Upwork’s Head of Human Resources and Talent Innovation, Zoe Harte, keeps the department at the cutting edge. Making sure that the right people in the right places are equipped with the skills and tools they need to perform at a high level requires strategic decision-making, so it makes sense that the person responsible for that core work would serve much more than an administrative role.
MATT MULLENWEG: Back in June we had the pleasure of speaking with Stephane Kasriel, the CEO of Upwork, the world’s largest freelance marketplace. Stephane laid out a compelling case for the distributed model as a way for talent-starved companies in expensive, crowded cities to do business with workers who live in places with comparatively sluggish economies.
But Upwork’s not just thinking about this in theoretical terms: they practice what they preach, with a distributed workforce of their own. In this episode, we’ll talk to two Upwork employees from two very different practice areas who give us glimpses of how their company does distributed.
Launching the Distributed podcast has given me space to reflect on the last 14 years at Automattic. In 2019, distributed work has spread throughout the Bay Area and beyond, but when we were getting started, having no corporate headquarters was seen as quirky. Our distributed status has come to define our company, but we didn’t set out to be distributed. It was common in open source projects and our initial team was spread around the world. But over time it became who we are.
I’m originally from Houston, Texas. In 2003, web developer Mike Little and I, along with a few other online friends, developed a web publishing tool called WordPress. It quickly became popular, but we had no inkling that it could ever be a revenue-generating project. We just wanted to make better publishing tools so that non-engineers could express themselves online with their own blogs. For me, it was satisfying simply to hang out on IRC (an early chatroom protocol) with smart, curious people working on an interesting collaboration. I was spending all my free time online, hanging out and coding with people all over the world, having an absolute blast.