Reed Albergotti has a great article titled Latest Amenity for Startups: No Office. You can put in your email to read I believe but it's behind a paywall otherwise. The Information is a pretty excellent site that alongside (former Automattician) Ben Thompson's Stratechery I recommend subscribing to. Here are some quotes from the parts of the article that quote me or talk about Automattic:

So it’s no coincidence that one of the first companies to operate with a distributed workforce has roots in the open source movement. Automattic, the company behind open source software tools like WordPress, was founded in 2005 and has always allowed its employees to work from anywhere. The company’s 680 employees are based in 63 countries and speak 79 languages. Last year, it closed its San Francisco office, a converted warehouse — because so few employees were using it. It still has a few coworking spaces scattered around the globe.

Matt Mullenweg, Automattic’s founder and CEO, said that when the company first started, its employees communicated via IRC, an early form of instant messaging. Now it uses a whole host of software that’s tailor-made for remote work, and as the technology evolves, Automattic adopts what they need.

Mr. Mullenweg said Automattic only started having regular meetings, for instance, after it started using Zoom, a video conferencing tool that works even on slow internet connections.

He’s become a proponent of office-less companies and shares what he’s learned with other founders who are attempting it. Mr. Mullenweg said he believes the distributed approach has led to employees who are even more loyal to the company and that his employees especially appreciate that they don’t need to spend a chunk of their day on a commute.

“Our retention is off the charts,” he said.

And:

“Where it goes wrong is if they don’t have a strong network outside of work—they can become isolated and fall into bad habits,” Mr. Mullenweg said. He said he encourages employees to join groups, play sports and have friends outside of work. That kind of thing wouldn’t be a risk at big tech companies, where employees are encouraged to socialize and spend a lot of time with colleagues.

But for those who ask him about the negatives, Mr. Mullenweg offers anecdotal proof of a workaround.

For example, he said he has 14 employees in Seattle who wanted to beat the isolation by meeting up for work once a week. So they found a local bar that didn’t open until 5 p.m., pooled together the $250 per month co-working stipends that Automattic provides and convinced the bar’s owner to let them rent out the place every Friday.

They didn't need to pool all their co-working allowance to get the bar, I recall it was pretty cheap! Finally:

For Automattic, flying 700 employees to places like Whistler, British Columbia or Orlando, Florida, has turned into a seven-figure expense.

“I used to joke that we save it on office space and blow it on travel. But the reality is that in-person is really important. That’s a worthwhile investment,” Mr. Mullenweg said.It might take a while, but some people are convinced that a distributed workforce is the way of the future.

“Facebook is never going to work like this. Google is never going to work like this. But whatever replaces them will look more like a distributed company than a centralized one,” Mr. Mullenweg said.

Dean Allen, a web pioneer and good man, has passed away. I've been processing the news for a few days and still don't know where to begin. Dean was a writer, who wrote the software he wrote on. His websites were crafted, designed, and typeset so well you would have visited them even if they were filled with Lorem Ipsum, and paired with his writing you were drawn into an impossibly rich world. His blog was called Textism, and among many other things it introduced me to the art of typography.

Later, he created Textpattern, without which WordPress wouldn't exist. Later, he created Textdrive with Jason Hoffman, without which WordPress wouldn't have found an early business model or had a home on the web. He brought a care and craft to everything he touched that inspires me to this day. As John Gruber said, "Dean strove for perfection and often achieved it." (Aside: Making typography better on the web led John Gruber to release Smarty Pants, Dean a tool called Textile, and myself something called Texturize all within a few months of each other; John continued his work and created Markdown, I put Texturize into WP, and Dean released Textile in Textpattern.)

Years later, we became friends and shared many trips, walks, drinks, and meals together, often with Hanni and Om. (When we overlapped in Vancouver he immediately texted "I'll show you some butt-kicking food and drink.") His zest for life was matched with an encyclopedic knowledge of culture and voracious reading (and later podcast listening) habits. I learned so much in our time together, a web inspiration who turned for me into a real-life mensch. He was endlessly generous with his time and counsel in design, prose, and fashion. I learned the impossibly clever sentences he wrote, that you assumed were the product of a small writing crew or at least a few revisions, came annoyingly easily to him, an extension of how he actually thought and wrote and the culmination of a lifetime of telling stories and connecting to the human psyche.

Dean, who (of course) was also a great photographer, didn't love having his own photo taken but would occasionally tolerate me when I pointed a camera at him and Om has a number of the photos on his post. There's one that haunts me: before getting BBQ we were at his friend's apartment in Vancouver, listening to Mingus and enjoying hand-crafted old fashioneds with antique bitters, and despite the rain we went on the roof to see the art that was visible from there. He obliged to a photo this time though and we took photos of each other individually in front of a sign that said "EVERYTHING IS GOING TO BE ALRIGHT." It wasn't, but it's what I imagine Dean would say right now if he could.