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.
Mark Armstrong: Hi everybody. Thanks for joining the Distributed podcast. I’m not Matt Mullenweg, I’m Mark Armstrong. I’m the founder of Longreads, which is part of Automattic, and I’m on the editorial team working with Matt on the Distributed Podcast.
So today I wanted to take a step back from the interviews Matt’s been doing and find some context for how Matt got here in the first place, how he became interested in distributed work, and it all starts with the history of Automattic. So that’s what we’re going to talk about today. We’re going to talk to Matt about how he got here, how he actually decided to build a company that had no offices, and what worked and what didn’t. Thanks for listening.
MATT MULLENWEG: Back in March, Arianna Simpson tweeted an offhand remark that went crazy viral.
“Unpopular Opinion: Remote work is mostly bullshit.”
Arianna had no idea that thousands of people would like the tweet, and hundreds would weigh in with their thoughts, some pushing back, others hailing the blunt honesty of her “unpopular opinion.” As a true believer in distributed work, I naturally had to get in touch with Arianna when I saw the tweet.
Arianna is an early stage investor, with close to 40 investments to date, many of which deal with the blockchain and cryptocurrency projects. I wanted to find out: How is it that someone, who knows so much about distributed software that’s created among globally-distributed teams, has such a pessimistic view of distributed work?
It turns out, as it often does, that Arianna’s thoughts on distributed work are more nuanced than her tweet might lead you to believe. We discuss her reservations with remote work, we cover some of the things that traditional office arrangements are really good at providing workers, and we explore how companies can give their employees the best of both worlds with a hybrid model.
But things really get cooking when we started talking about how the blockchain could one day be used by distributed companies to pay workers in far-flung locations with stablecoins that are pegged to a traditional currency. When money becomes programmable, all kinds of interesting contracts and financial arrangements open up, making it easier than ever for the distributed company of the future to partner with workers all over the world.
ARIANNA SIMPSON: My name is Arianna Simpson and I run a fund called ASP. I’ve been an investor for the past several years, first general VC, and now running a crypto-specific fund.
Matt: So you’re into distributed systems.
Arianna: I am.
Matt: One of the reasons I really appreciate you coming on — and a goal of this podcast is — I wanna have the very best versions of why people should be in the same place, as well as making the case for distributed work. We are obviously in the same place right now.
Arianna: Yes, we are.
Matt: We are in a tiny studio in New York City, and this is nice, right? Because we’re having a higher-fidelity communication.
Matt: This all started in a tweet. Do you remember the tweet?
Arianna: The tweet heard round the world! Oh yes, it was kind of Paul Revere-ish in its quality in that sense.