Despite the rise of distributed work across the corporate world, the Trump administration is pulling back. In a departure from the previous president’s move toward distributed work, multiple federal agencies are ending remote work provisions and mandating co-location.
Trump’s war on telework represents a milestone in how his administration is changing the culture of the federal government as it seeks more accountability from employees — and moves to weaken their unions. Employees are chafing at their lost freedom, but the managers reining them in say that, in the long run, taxpayers benefit. Overall, data on productivity is inconclusive, workplace experts say.
MATT MULLENWEG: Howdy, howdy, and welcome to the Distributed podcast. I am your host, Matt Mullenweg, and I’m here with our first episode of 2020. Today’s guest is Jason Fried, the CEO of Basecamp, a semi-distributed company that’s been making project management tools for about 20 years now. Back in 2013, Jason wrote a book called Remote, which was an early manifesto for remote and distributed work models. I’m excited to catch up with him to hear about what he’s learned in the six years since that book came out and how Basecamp operates today.
Jason Fried, the co-founder and CEO of Basecamp, collects mechanical watches. He appreciates their simplicity. He once wrote in a blog post, “When I look at my watch, it gives me the time. It asks nothing in return. It’s a loyal companion without demands. In contrast, if I look at my phone for the time, it takes my time. It tempts me.”
MATT MULLENWEG: Howdy, howdy. Here we are. We made it: the last episode of 2019. The finale of our first season of the Distributed podcast, with me, Matt Mullenweg.
We’re currently in the thick of planning a fresh slate of episodes for next year. We’ve got the first female 4-star general in the U.S. Army, a guy who grew up in a family of Argentinian sheep ranchers and now runs a distributed blockchain company. Business leaders, thinkers… I’m really excited for next year overall.
But December is also a great time to reflect. So that’s what we’re going to do now — reflect on some of the great conversations we had in 2019 and talk about where we think distributed work is headed in 2020.
Looking back over the 2019 run of the Distributed podcast, one is struck by the wealth of insights our guests have shared in each and every episode. We’ve spoken to CEOs, activists, lawyers, authors, and a life coach, among others — a diverse cross-section of people with a deep interest in the future of work.
The Australian company dipped its toes into distributed work after its acquisition of Trello, which was already mostly remote. They researched the model, assessed their readiness, and developed a pilot program for their Jira Service Desk product.
The company has also instituted a number of rituals to better include these workers. For De Coninck and her colleagues, this includes the life-size cutouts of each remote worker, as well as a weekly Wednesday morning session where everyone on the team calls in to work together. The team also dials in for Friday evening social time where they can hang out, play video games or simply have a drink over a video call and bond as colleagues.
MATT MULLENWEG: A lot of tech companies talk about prizing “people over profits,” but Glitch is a startup that is serious about these ideals, and holds itself publicly accountable for sustaining this commitment as the company grows.
That’s partially because Glitch’s CEO is Anil Dash. Anil’s an old acquaintance of mine — he’s one of the early pioneers of blogging. Over the last twenty years he’s developed a reputation as something of a tech prophet — not just for predicting what’s going to happen next, but for holding the industry’s feet to the fire.
Anil Dash has been blogging for 20 years, getting his start during the medium’s earliest days. In the summer of ‘99, he was looking for a way to pass the time during his three-hour train commute. Having recently discovered a small community of techie bloggers, Anil thought he’d try his hand at this emerging craft. Back then, bloggers had to overcome technical hurdles that are unthinkable to those who’ve grown up with established blogging software (like WordPress.com). But despite these challenges, something about blogging clicked for Anil. Putting his thoughts online helped him collect and refine his thinking. Plus, it was fun. Later that year, Anil was invited to a bloggers’ dinner in New York City, which he says included “all” of the bloggers — a group small enough to fit around a couple of tables in a Mexican restaurant.
Josepha: The song that’s in my head right now is “Good morning. Good morning.” My name is Josepha Haden Chomphosy. I shouldn’t say it like a question. That is my name. My name is Josepha.
Mark: Great to see you. Thank you for stopping by the Automattic podcast booth. Josepha what do you do with Automattic?
Josepha: Great question. A little bit of everything. I am the lead of the .Organization Division, which is the division that supports and helps to guide a lot of our open-source work with the WordPress project itself.
Since launching the Distributed podcast, we’ve learned that most distributed companies host in-real-life (IRL) meetups in order to promote social cohesion and a sense of collaboration among colleagues who might not otherwise ever spend time face-to-face. As much as leaders at distributed companies value the many benefits of remote work, they also recognize the importance of meeting in person. Automattic CEO Matt Mullenweg has blogged about the connection between meeting up IRL and the health of a distributed company, and has encouraged individual teams of Automatticians to meet every year in various locations around the globe.
MATT MULLENWEG: Howdy howdy. Welcome to the Distributed podcast. I’m your host, Matt Mullenweg.
My guest this week is Clark Valberg, the founder and CEO of InVision, a company that makes a collaborative design platform that’s very popular with distributed teams. It does ideation, design, prototyping, sharing… and it all lives in the cloud. No more emailing files back and forth — it’s pretty slick.
MATT MULLENWEG:Howdy howdy. Welcome to the Distributed podcast. I’m your host, Matt Mullenweg.
Today’s guest is Lydia X. Z. Brown, who is a… well, Lydia wears many, many hats — we’ll get to that in a minute. Lydia once gave a talk for Automattic about disability inclusion, and today we’re going to continue that conversation.
Lydia X. Z. Brown is a lot of things — writer, advocate, organizer, strategist, educator, speaker, and attorney. Why do they spread their time and expertise across so many arenas? Because Lydia chooses to dedicate every aspect of their life to promoting social justice for some of the world’s most marginalized people.
MATT MULLENWEG: Howdy. My name is Matt Mullenweg, and I run a company called Automattic, with over 950 employees distributed across over 70 countries. We’re growing quickly, so I spend a lot of time thinking about how the company is going to find the very best people. Since our team leads might never meet a far-flung applicant face to face until well after they’ve been hired, our hiring process has to be comprehensive, so sometimes it can be a little bit of a slow and long process.
In tech hubs like San Francisco and New York, the demand for top-tier talent can outstrip supply, so HR departments find themselves in a fierce competition for local job applicants. In response, some companies have turned to the distributed model, which allows them to reach beyond hub cities and to access qualified candidates around the country and internationally. Hiring for distributed positions comes with its own set of challenges, though.
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.
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.
We believe that distributed work is great for many reasons, and will eventually replace most traditional office environments. But an important part of treating distributed work seriously is discussing its downsides and the hurdles it presents to teams and individuals. To better understand the concerns around the distributed work model, Matt recently spoke with venture capitalist Arianna Simpson, a vocal skeptic of remote work.
It’s difficult to know what kinds of statements are going to make a big splash on social media. Brands spend untold resources trying to learn how to “start a conversation,” but usually the tweets that go viral are offhand remarks that were never conceived as definitive statements.
Such was the case with venture capitalist Arianna Simpson’s “tweet heard ‘round the world,” as she calls it. She set out to share a casual thought with her audience, but something about her perspective touched a nerve:
Matt Mullenweg: We’ve been hearing about virtual reality since the late ’80s, but this technology still hasn’t yet leapt from the pages of science fiction into our universe—at least not into the mainstream. The VR revolution seems to be always just around the corner, but some people believe that we really are on the verge of something that’s going to change everyone’s lives.
John Vechey, cofounder of Pluto VR, is one of those people. He’s specifically interested in how VR is going to change the way we communicate. John found success as the founder of PopCap Games–you may know them as the folks behind your favorite mobile games like Bejeweled or Plants vs. Zombies. After selling PopCap, he transitioned into virtual communications.
I wanted to speak with John because he’s got some big ideas about how VR will one day be used for work.
Those of us who work on distributed teams have become accustomed to a workplace tool that, even after almost two decades, still feels very sci-fi. It’s cheap, it’s seamless, and it’s ubiquitous: video chat.
Chatting with video has long felt like an inevitability; it’d been featured in popular culture since at least the advent of the telephone. From The Jetsons to Star Trek, many of our utopian visions of the future involved the simple but rather magical concept of broadcasting your face across the globe, if not the galaxy.
Matt: To start off, say your name and how long you’ve been here, just so people have a sense of you. And then we’ll talk.
Stephane: Sure. So my name is Stephane Kasriel, I’m the CEO of Upwork. I joined the company close to seven years ago. Initially I was running product management and design and then when our head of engineering left, I became the head of product management, design and engineering. And then a couple years later, when the CEO left, I got promoted and became the CEO of the company. And that was about four years ago.
Stephane Kasriel, the CEO of Upwork, thinks that work, as we think of it today, is in need of an overhaul. Nothing less than the American dream is at stake.
The cities where the best jobs can be found are crowded, the commutes are long, and the rents are outrageous. The jobs themselves are inflexible, and closed off to most of the world’s talent pool, so employers end up poaching workers from each other. Enterprising people who move to hub cities like New York or San Francisco live in cramped conditions, and pay handsomely for the privilege. Many can only hope to win the lottery of a successful startup exit to afford such luxuries as home ownership.
Meanwhile, there exist vast swaths of America where rents are affordable and life is comfortable. But the jobs just aren’t there, and haven’t been for decades. If there were some way to bring the jobs to those places, you’d ease the pressure of city life, revitalize local economies around the country, give employers better access to labor, and give workers a higher quality of life.
Changing the way we think about work
Upwork is the largest freelancer marketplace, and is valued at close to $2 billion, operating in 180 countries, and connecting millions of distributed workers with employers. Kasriel built and led a team of over 300 engineers located all over the world as Upwork’s SVP of Engineering before taking on the role of CEO. Prior to joining the company, he was a leader at PayPal, where he helped grow the company’s presence in France and subsequently led its consumer strategy. He thinks a lot about labor trends, and established himself as early as 2014 as an expert on the growth of the distributed work model with his book Hire Fast & Build Things, which details how managers can build distributed engineering teams in order to scale quickly and cost-effectively. He sees this problem as a collection of bottlenecks that are a result of our stubborn reliance on an outdated labor model.
My life’s work is WordPress. But in building my life’s work, I discovered something just as important:
Talent is evenly distributed around the globe, but opportunity is not.
With WordPress, I discovered the power of open source software development. I met a group of like-minded people online, and we worked together to build a publishing platform that now powers over one-third of all websites on the internet.
In our quest to democratize publishing, I realized we were also changing the way work gets done. While the early companies of Silicon Valley started out in garages and cramped workspaces, WordPress was being built without any offices at all.