Transcript: Episode Three, Arianna Simpson

Read more about Arianna Simpson in “Is Remote Work Bull***t?”


Distributed Podcast: Hear Matt Mullenweg in conversation with Arianna Simpson.

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.

Arianna: Mhm.

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.

Continue reading “Transcript: Episode Three, Arianna Simpson”

Is remote work ‘Bull***t’?

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:

Continue reading “Is remote work ‘Bull***t’?”

Transcript: Episode Two, John Vechey

Read more about John Vechey in “For Years, VR Promised to Replace the Office. Could It Really Happen Now?

Distributed Podcast: Hear Matt Mullenweg in conversation with John Vechey.

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.

Continue reading “Transcript: Episode Two, John Vechey”

For Years, VR Promised to Replace the Office. Could It Really Happen Now?

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.

Continue reading “For Years, VR Promised to Replace the Office. Could It Really Happen Now?”

Transcript: Episode One, Stephane Kasriel

Read more about Stephane Kasriel in “The American Dream Is Broken, and I Think We Have a Shot at Fixing It.

Distributed Podcast: Hear Matt Mullenweg in conversation with Stephane Kasriel.

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.

Continue reading “Transcript: Episode One, Stephane Kasriel”

‘The American Dream Is Broken, and I Think We Have a Shot at Fixing It.’

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.

Distributed Podcast: Hear Matt Mullenweg in conversation with Stephane Kasriel.

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.

Continue reading “‘The American Dream Is Broken, and I Think We Have a Shot at Fixing It.’”

WordPress Showed Me the Power of Distributed Work. It’s Time to Share What We’ve Learned.

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.

Continue reading “WordPress Showed Me the Power of Distributed Work. It’s Time to Share What We’ve Learned.”