Automattic CEO Matt Mullenweg on building a fully distributed company

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 step back from the interviews Matt's been doing and sort of 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. Now, where are you right now?

I'm actually in San Francisco, California.

And I am in Seattle. This is basically how we record this podcast for people who are remote. We have a Zoom connection. We use GarageBand, a tool called Zencastr, and we put it all together. And it sounds like we are having this intimate conversation right next to each other. But this is a very good sort of symbol of how distributed work has changed and the technology has changed. So take me through the very beginnings of Automattic and how you ended up with a distributed work model in the first place.

Well, at the very beginning, I had moved from Houston to San Francisco, actually, to take a job with CNET Networks. And they were actually an early adopter of WordPress. So they offered me a job as like a product manager to drop out of college in Houston. I drove across country with my mom and got a little apartment in San Francisco.

Did you apply for the job?

So what had happened was I had said if I ever hit number 1 on Google for the search term Matt, I would shut down my site, kind of go out on top like MJ. So that happened partially because most WordPresses included a link to the main developers of which I was one. And they all said Matt. And so those links started helping me rank first for Matt. So I just replaced my site with a little kind of black screen that said, you know, this happened. And came out to San Francisco because this got some news when this happened. A bunch of people reached out.

So at this point, you had already started WordPress. Did you already have in the back of your head the idea of building a company around WordPress? Or were you thinking, well, the CNET thing will work out for, you know, a couple years and see how it goes?

I'm guessing this was probably 2004. At the time, there was no indication that anything related to WordPress could ever make money. It was very much like a volunteer project. And there weren't really examples, certainly not as there are now, of kind of consumer open source becoming a commercial thing. What I did know was I was already collaborating with folks all around the world, having a blast and using basically all my free time to get online, hang out in IRC, which is kind of like an early pre-Slack chat system, and basically code with these people who were also passionate about making publishing easier.

So you're doing all this work on something that you love, and then you're commuting into an office in San Francisco. What was the office experience like? Was this sort of the moment where you're like, I never want to work in an office again, so I will never do that?

No, the opposite. It was amazing. CNET was one of the first companies to actually set up a headquarters in San Francisco. Most of the major companies were and are down in like Mountain View or Cupertino or someplace else in the Bay Area, San Jose. But I looked very, very close to the seen that office. And then when I moved in, I kind of a patron there, a guy named Mike Tatum, got me this really cool office kind of right above the door, like a corner office. And I remember this VP came by, and of course the conversation like, hey, where are you from, how you doing, what are you going to do here, etc. He started to look around and be like, man, this is a nice office. You can guess what happened next. Like 2 weeks later, I come to the office and there's a note on my door It's like, "Oh, we're doing an office move." And I got moved to an interior office, kind of in the same section, still on like the third floor, but more of an interior non-window office. But then there was kind of a general reorg in the group I was in. That whole floor got taken over by GameSpot that was doing really well. And they literally moved my group into the basement, kind of the very, very first area. So now I was not just no window, I was like in this very small area. And that was around the time I think I started to think, um, this might not be for me.

So you're putting together the idea for Automattic as a for-profit company that then would contribute to the WordPress open source project. So you're viewing this as an opportunity to merge the two ideas of sort of the nonprofit open source side and a for-profit company that feeds into it. Is that the original idea?

So the original idea I actually pitched at CNET. So they had a lot of cool domains, famously com.com, download.com, and one day I got a list of all their domains. They had probably 1,000 from different acquisitions and stuff. And I went through and I was like, okay, well, it could be cool. And I came across one called online.com. So the idea and the pitch I made to them was, let's make a version of WordPress that anyone can start with. So instead of having to like know PHP and configure a database and FTP and all these things, let's make it kind of self-serve where you can just click a few buttons and get one. That could be, you know, mark.online.com, could be kind of your online home. And you could have a blog and a profile and all this cool stuff. So I really pitched that quite vigorously. But at the time, what was kind of going on was this colossal battle between blogs and traditional publications. And two, every single internet giant had a blogging system, but they were scared to call it blogging. So Yahoo had one called 360, AOL had Journals, Microsoft had something called LiveSpaces, and then of course Google had Blogger. And so it appeared that all the internet giants, and those were the internet giants at the time, all had something in this space. And CNET, one, thought they couldn't compete, and two, thought that blogs were just gonna be like noise and politics and mess and junk, and they were really gonna bet on professional publications. They were at the time kind of locked in news.com, which was kind of a tech publication, was kind of battling, or ZDNet was battling with Gizmodo, which was one of the early blogs started by Nick Denton in the Gawker network. And Gadget from Jason Calacanis and Pete Rojas and those folks was also just getting started. They saw themselves locked in this epic battle of like professional versus amateur and didn't want to do anything related to blogging. So I said, well, I have to do this. I'm going to leave and start this. CNET very graciously invested in what became Automattic, but asked if I could stay a few months to finish up some of the projects I was working on. So I did, but in those few months went ahead and started Automattic. I already knew the people I was working with as the other lead developers of WordPress and started to try to convince them to leave their jobs. And the first one actually was a fella named Donnacha Ó Cuív who was over in Blarney, Ireland. And he had started actually a different fork of the software that became WordPress. His was called B2++, I believe, and we decided to merge that with WordPress and make that WordPress Multi-User, what later became WordPress Multi-Site. Basically a version of WordPress that was multi-tenant, that could have lots of people clicking a few buttons and starting a blog. I want to say the second was either Ryan Boren or Andy Skelton, and I was technically the third, because I stayed a few extra months to finish up things at CNET. And then we started Automattic.

Already you've built the beginnings of this company and you've already got employees that are spread out all over the world. So was that simply, okay, well, these are the people I trust and want to work with, and so we're gonna build a company that way? Or was there more sort of deliberation around that?

Well, one aspect was definitely having no money. So I was just paying Danica and these other folks out of my CNET salary, basically. And for servers and things, starting to rack up some credit card bills. And so it was very much like, well, moving is really expensive and we're already working together. And in fact, those were the days when we'd all work very, very long hours. So if you're working 10 to 16 hours a day, you're overlapping quite a bit with someone who's, say, in Ireland. And we had this awesome kind of almost relay thing where I'd work until night, and when he would wake up, start working, and then I'd sleep, wake up, and there had been kind of a whole cycle of things done to the software. Actually allowed us to iterate very quickly and brought in some asynchronicity very early on to our interactions.

Now at this point, how are you communicating with each other?

Probably we used AIM, AOL Instant Messenger, which is now shut down, IRC, and we were either still on SourceForge, which was kind of like an early GitLab, or maybe at this point had switched to hosting the code on WordPress.org.

So this is a lot of baseline sort of foundational communication that sounds very familiar to me, even in current day Automattic.

We actually still run IRC servers to this very day, and some people like to use them. But the evolution at the time, AIM was definitely kind of the most popular chatting platform. At some point we switched to Skype, again for chat, not really for voice. But I do remember some of those early voice calls where we kind of for the first time would talk to each other and have what maybe was our first meetings. And the average meeting cadence at that time was probably like 3 per year. We didn't do a lot of them. It was really very much a written communication style.

Yeah, and you hadn't met in person yet.

None of us had met in person. Around that time was when I hosted the very first WordPress meetup in the world. Which ended up being kind of 8 people at an Indian place, which is still there on 3rd Street called Chat Café. Those 8 people ended up being pretty interesting. So there was Chris Messina, who at the time was involved with Drupal project and would later go on to invent the hashtag. Scott Beale of Laughing Squid, which is now a large WordPress web host. Om Malik, who is a journalist at Business 2.0, later started GigaOm, again, one of the earliest WordPress users. And someone who I met for the first time, which was Ryan Boren. Matt Mullenweg, who was one of the first kind of major contributors to kind of the core WordPress. And he was, I want to say, a kind of embedded systems engineer at Cisco.

So there's a point though where you are going to then bring Automattic to investors and raise some money. How did they react to this idea that you didn't have an office? Everyone was all over the place.

We didn't really. Plan to raise investment in the beginning. We were just kind of focused on making money, to be honest. So we thought that we could have add-ons for WordPress.com. I think some of our early ones were custom CSS for customization and domain names. So this would kind of allow people to be a business model. This idea of kind of ringtones for blogs, so you could buy like customizations or add-ons. Actually not dissimilar to what we do today. And then we started to also do partnerships with different hosting companies who provided hosting and then could pay us for, for essentially new customers. So that was the early business model, and that started to make a bit of money, you know, enough where we could each take kind of a modest salary of a few thousand a month. And that was kind of just a plan. We didn't have a ton in the bank. There was enough for a few of us to work on WordPress full-time, and that was really just a dream. I mean, the company was created to have a place where we could be paid to contribute to open source. And so we were all kind of happy as clams.

It seems like you had gotten far enough along with sort of the growing group of contributors and employees that you were already proving that distributed work was working. And so by the time you ended up bringing in outside investors or others, other partners, that, that wasn't really a question anymore. Is that right?

I'd met some different investors, folks like Tony Conrad and others, but I was at this point 21, so pretty young, and that was the era where kind of pre-Zuckerberg, pre-all these other things where you brought in adult supervision. So the model was really Eric Schmidt. Adult comes in and kind of professionalizes the business. I didn't really want that until actually Om Malik introduced me to a fellow named Tony Schneider. Who had sold a company called Oddpost to Yahoo. It was kind of the original Ajax Gmail predecessor that allowed you to have a very web application feel in the browser. They were the first to do that that I had seen. But he wasn't gonna stay at Yahoo. So Om had done a cover story on the company for Business 2.0, and he said, "Hey, you gotta meet this kid from Texas." He told me, "Hey, you gotta meet this guy, Tony. He's not gonna stay at Yahoo too long." So we met and really, really hit it off. Tony's an amazing individual, came from Switzerland, moved to California, ended up going to Stanford, had a few startups under his belt, including this very successful exit at the time to Yahoo, and was a CEO. And I was like, ah, this guy's like my business soulmate. If this is the adult, I can totally bring in an adult. This guy is amazing. And I learned so much from him. That was with the expectation that Tony would join the following year. When he was able to leave Yahoo, ended up raising the first round for Automattic, which was about $1, I think $1.1 million from folks who we actually still work with today, like Phil Black at True Ventures, Doug McKenzie, Kevin Compton at Radar. So that kind of first early round, and I was the CEO for, I forget how long, the first ever, however many months before Tony joined, and then we started working together.

Was there ever any pressure to eventually— okay, this is great, I love distributed work, but we also need some physical offices. How much pressure had come in those early days?

Well, first we just use our investor's office. So at the time, Blacksmith, which is the predecessor to True Ventures, had a space in the Presidio. So Tony and I would just get together at restaurants and coffee shops. Then if we ever needed to have a meeting or something like that, we go to this awesome office in the Presidio. Later, True when they formed, moved to this awesome pier called Pier 38. They very presciently were like, okay, we're a VC, we're only this many people, but we can get this office space that's a few thousand square feet. Let's just put a few tables at it. So one table was GigaOm, one table is Automattic. Actually, upstairs was, uh, Burbn, which later became Instagram. So there was kind of a, a cool center of early startups that would just kind of have a little desk here. And so Tony and I would go in there and meet or work from there, but there was no reason to try to move the rest of the company there because they were perfectly happy being where they were. I think Danica was just about, or had just gotten married. Immigration seemed really tough. You know, there are a lot of barriers. So I was like, well, this is working, so let's just continue to hire people wherever they are. However, at the time, it wasn't clear that that was the thing we were always going to do. A lot of investors said, "Yeah, this will work when you're 10 people or 15 people, but at some point you need to get an office or need to bring everyone into one place." So we always kept that in the back of our mind as something that we might need to do and always had like this kind of small headquarters, first a desk in True Ventures space, then we moved across the hall to a bigger space where we hosted lots of events and meetups. This idea that we needed something to be like the official address of the company persisted really until— gosh, when did we shut down our office? Was that 2016?

It was a couple years ago.

We actually continued having a headquarters really until then, partly this idea that on average, as we started to scale, about 10% of the people we hired were in the Bay Area, and the ones who we did like to go into the office at San Francisco. So we kind of assumed as we got bigger and bigger that ratio would continue kind of at 10 to 15%. And it turns out it mostly did, but what changed was the traffic and everything got so bad, parking got so bad in San Francisco, that even the people we'd hire in the Bay Area didn't really want to commute. And then the tools for collaboration got better and better, so they didn't really need to.

It's interesting because there's a lot of this early automatic history that you're in San Francisco and you need to be in San Francisco physically in terms of the existing power and money, I guess, to be able to get a foothold for the company?

I think it felt like that as the leaders of the company, we need to be in San Francisco, but the rest of the company didn't. So it's great for Tony and I. We actually didn't really have any new funders until 2013, 2014, and we were relatively unique at the time that we had one kind of West Coast VC, Blacksmith, later True, but our other investor was on the East Coast. Called Polaris. So we were already kind of distributed from our initial funding, and that was kind of unusual for East Coast VC at the time to invest outside of their geography.

Now, will we ever get an office back in San Francisco?

Yeah, we probably will. So if something really interesting comes back up, we'll get a small space, but it'll probably be a secret, and it'll probably be just for like board meetings and investor stuff, not something that is really an office like we've had in the past.

I want to switch over to some of the culture inside of Automattic since the early days. So Automattic has its own creed. For those of you who have not read it before, you can go to automatic.com/creed. But one key line from that is, "I will communicate as much as possible because it's the oxygen of a distributed company." I know how it is today, and we can talk about it in a second, but in the early days, did that mean that every single conversation was public? And there were no private conversations. What was transparency and communication like in those early days?

Yeah, it really was, because there was— wasn't really any reason to not have everything be open. The whole company was in kind of one chat room. We had no teams, we had no managers. It was totally flat. We just organized around projects and code, really. And there was just such an advantage to kind of knowing everything else that was going on. And we were doing few enough things that you couldn't know everything else that was going on. And there was a lot of information sharing or kind of seeing the flow of code commits and code changes and conversation. You got the shared collective intelligence of everyone at the company pitching on every idea. So although we didn't have like formal product managers or a ton of designers or things like that, because everyone was using everything, we used WordPress ourselves, and seeing things that went through, you got a lot of real-time feedback. Almost like real-time user testing with your colleagues that ended up speeding up the iteration cycle and leading to some very usable products even in early iterations.

That probably brings us to P2, I believe was introduced in 2008. And so for those who don't know, P2 is essentially a WordPress theme for groups to share status updates with each other. I personally still see it as sort of the foundational tool of all communication inside of Automattic to this day. But I went back and looked up your first post on Update-O-Matic, which is the all-company blog inside of Automattic. And I can see that you wrote the quote, "Finishing up meetings." That was the entirety of your P2 post.

Well, it was pre-P2. We just had an internal blog and we used it much like Twitter, which at the time was called like TWTTR. The idea was just that original, the prompt on Twitter, which is, what are you doing, or what's going on, dot dot dot, or something like that. And so you would post literally whatever you were doing at that second. So finishing up—

it's like people tweeting what they had for breakfast or whatever.

That was the goal, actually. So a way for us to put things on there. And then we started to see that it was useful to have a place that you could have comments on or could do threads. We used it for keeping data.

So P2 was not introduced yet as an actual thing. This was still just the internal blog.

Didn't come to many years later. So it was really just this internal blog and IRC. What was from the very beginning of Automattic was this concept of meetups. Actually, early on, we did two, I think, in that one of those early years with 5 to 15 people. One that stands out in my memory because it was an utter disaster was Stinson Beach, which is a place where I think we all fit in one maybe 2 homes. We went on Stinson Beach, which is north of San Francisco, and we didn't really know what to do at a meetup. So I think we assumed that we should just have all day long meetings and debates. This drove— I won't name who— but drove someone crazy. And it ended up being, I think there was like a walkout of 1 or 2 people. Voices may have been raised. Like, it did not go well. With the, at the time, valid feedback, which is, are we sitting around like just arguing about things for hours and hours, not getting anywhere, not driving to decisions? And by the way, we could do some of this written. Like, why does it need to be in real time, people reacting to information versus considering it, thinking about it, and writing a response in a deliberate way? Which, if you think about it, is a much, much better way to have a debate or exchange of ideas than people just reacting in real time to whatever information's popping up in their it. So that first meetup was a little bit of a disaster, and we decided to move them to once a year and make them more organized. So we introduced the concept of meetup projects or hack weeks. So the idea was we would get together and start and launch a number of things during that week as a way to do things we wouldn't normally do, just have fun. It's very much like getting together and just working intensely alongside someone was a honestly still really fun and was hard to replicate with the tools at the time.

I mean, I think that holds to this day, this idea that the meetup should be a social event as well, because you've got the entire rest of the year and you have all of these tools in which you can organize and communicate and brainstorm. And so really pinpointing the specific things that you can only do in person together, and that's also building relationships and building trust with each other. That you can then go back and be honest on Slack and P2.

Exactly. Those meetup projects ended up creating a lot of the things that became very crucial to Automattic today. So it evolved what first was called Prologue, which was kind of the early version of theme for WordPress, which put the posting on the home screen. So again, very much like a Twitter built on WordPress that looked a lot like what early Twitter looked at, at the time, which is just a box and a list of posts. And then later that evolved at a later meetup into what we called P2, which basically took Prologue and made it real time so that as things were posted, they would show up without you having to reload the page to get new comments or anything. So that was the evolution of what became, what was and still is to this day, the most important communication tool inside Automattic.

It's an interesting segue to today because you've got P2, there are now hundreds of P2s, team and project P2 websites across the entire company. And then we have this global search tool in which people can search across every one of these websites. We also have a field guide, which is more evergreen pages of documentation. But the P2 is where most of the deep communication is. And I, I'm raising this inter— as a segue to today because seeing your original finishing up meetings post and then seeing a post just the other day from Nick Momrich on our HR team about the growing word counts of our P2 posts as a trend, I think we can see that, you know, P2 has not fundamentally changed, but how we use it has changed, especially once we started to embrace something like Slack.

Let me paint a picture, P2, so people listening can know what it's like. So imagine on kind of like a website with kind of a main area and a sidebar. In the main area, there's a post box at the top, so you can type in there and click post, and it shows up immediately, much like a Twitter or Facebook. Below that is something that's— can be post of any length, but all the comments are inline. So all the conversation happening next to a post, which again doesn't need a title, can be right there, and they pop up in real time. And on the right, on the sidebar, can be widgets that allow you to search, might have a list of people on the team, could have a schedule, could have notes, could have links to things, to resources, could have target launch dates or countdown timer. And so the sidebar, it becomes kind of like your ultra-customizable homepage for your team or project. The key for us was, as you mentioned, transparency was kind of our default for most of our communication. The one thing that was, didn't really work with that was email, right? So we'd email each other, ideas and threads and brainstorms. But then like if someone new joined the team, they had no way to catch up to those emails. And there was all this kind of intelligence and data and wisdom being lost in people's inboxes. Also, our email was kind of busy at the time because support was all done through email, and support@ was just an alias for everyone@. So every support thread we got would go to everyone in the company, and just whoever replied first would kind of claim that email or that ticket. So P2 Prologue, this internal blog, became a way for us to eliminate email. So anything that I would normally email, let's say, hey Mark, I've got this idea for a podcast, I think it should be XYZ, I would just post that as a blog post and you could see it whenever. And you still got that sort of general intelligence that anyone else could see it and choose to interact with it or add their two cents to it, which is both a blessing and a curse. It's a blessing when you want the sense, and it's a curse when you're crushed under a sea of pennies.

So I want to go back to today. I mean, one could argue, at least from my experience, I joined just for the record in 2014, but one could argue the past 2 years at Automattic have seen some of the most dramatic changes since you've started organizationally. We've grown very quickly. We're now 900 employees, and where we once were a sort of strictly flat organization, we made up our own titles. We now have executive roles, product roles, and actual hierarchy. Can you talk about what's changing and why at this stage and why it's important?

Sure. A common misperception about Automattic was that we were non-traditional in structure, and that probably stems to— I avoided creating any hierarchy or really teams or normal company structure until we were maybe 50 or 60 people. And it became really, really necessary. So that's where that comes from. But really since then, which is, by the way, the time chronicled in Scott Berkins' book A Year Without Pants, which was— he was joining partially because I was like, oh, we need someone who's done this before to help us create these teams. But ever since then, we've had a completely normal org chart, completely normal hierarchy, although I'm a strong believer in how we work being kind of non-traditional. Distributed, it's still really important for lines of accountability and for people to know where they fit and have one-on-ones and all those sorts of things. So that part of Automattic's always looked kind of normal.

Essentially, we've got team structures, which are— teams can be, what, 8 to 10 people per team, and they've got sort of a specific focus. What's the ideal team size?

So how we've approached Automattic is in a fractal way. So the idea is that if you zoom in or zoom out of Automattic, it looks kind of like the structure that's self-similar in many ways. So, you know, when Automattic was 10 people, we had a designer, a business person, a bunch of engineers, and we'd all work together to iterate on our area. So our team structure inside Automattic is very much modeled on that cross-functional idea where you get everyone together and you just kind of that It's a classic idea, two-pizza team, or whatever you want to call it. Get people working together with the autonomy and all the know-how that they need to ship and iterate with users, ideally as frequently as possible. Then when that gets too large, much like cell division, you split into two identical teams. And now you have two teams of, let's say, five doing cross-functional work. As that grew, you know, we eventually had divisions. And now kind of business units that are made up of divisions. Our largest business unit probably has 260 people in both product and engineering and design. But still, if you zoomed in on one of those teams, it looked very much like the teams that we had a decade ago.

And the tools too look very similar. So we still have the P2, as we've gone over. We use Zoom. For video conferencing, as you and I are doing right here. Then, of course, Slack came into the picture. That was shortly after I joined the company, and it was— that very much started with you, right?

I feel like—

I feel like we were experimenting with it and then you decided, let's go all in.

I appreciate the credit. You know, with many things at Automattic, we give the teams a lot of autonomy. So we had tried to adopt I think HipChat before, other things that were a little bit in the IRC. It just didn't take. I wanna say probably the mobile team, or there was some team inside Automattic that adopted Slack. And then it was optional for people to get on it. Many, many did when we utilized their kind of free version. I also knew Stewart from his Flickr days, and so I knew a lot of people involved with it. And in fact, a very early Automattician, Hany Ross, joined Slack pretty early on. I think she was one of the first, call it 20 or 30 there. So we had that connection as well. It just got so good. And my decree was more that we still had a chunk of the company that was really holding out on IRC and didn't want to sign into Slack. And for communication tools, it's really, really important to have everyone on the same thing. And we were going through a lot of growing pains, kind of our non-IRC was mostly through Skype Skype. And so it would, or if IRC would go down, we'd use Skype. And that was just really awkward because then you'd have to like add everyone who joined the company manually. So it was just a very weird process. And so Slack, everyone being on there, the directory, you know, the things that everyone knows and loves about it, was just so darn convenient. It really seemed like a better version of IRC. And in fact, you know, a lot of the conventions in Slack are directly modeled after IRC. Like the reason why public channels have a hash in front of it. That's taken directly from how most IRC clients work. So it was pretty natural, and just for communication, standardization seemed important. So that was what I think eventually got our systems team onto Slack.

I think it fundamentally changed how we even use our other tools like P2. And, you know, whereas P2 maybe was more of a conversational tool in the past, now it's a little more maybe announcement focused, or this is our plan focused? What would your take be on how P2 has evolved in, in sort of the world of Slack?

It totally depends on the team. I would say this is one of the things that's changed most. I don't know if it's for the better, but it is, you know, I'll observe it in a neutral way, that as we, you know, hired more and more people that didn't kind of come from the online collaboration or open source space, which, to be honest there's only so many people who have worked in like a, an open source project or things like that. They brought an approach to P2 that was a little bit more like announcements, like you said, and more meeting-centric. So needing more of that kind of synchronous real-time communication and get everyone on the same page. And I think that coincided a bit with Zoom, which honestly makes meetings a lot easier than they've ever been and more pleasant than anything we've done in the past. So I think also people just wanted to connect better. We have a lot of psychological diversity in the company. I would say early on, very much composed of introverts, including myself, for whom text was really first choice of communication. And as the company grew, a lot more extroverts, or people who wanted to use voice or see each other as they converse. And it's hugely controversial early on. Even the idea that we'd have an audio-only meeting was widely debated for why that's needed. If for nothing else, then it'd be inconvenient for, you know, everyone not in a couple time zones. But, you know, teams can kind of choose their own way. So as more and more teams had more and more people that were maybe composed of these extroverts or that wanted the real-time synchronous communication, and the tools got better, we started to use that more. And so on a team-to-team basis, it varies a lot. I love, for example, our VIP team. It's kind of the enterprise part of Automattic. Uses P2 I think the best of any team or division within the company. And they put really everything through it. And their Slack is still busy, but they really put a lot of thought and their P2 is great to read. It's funny, it has GIFs, it's fast, it's, you know, everyone has it pretty dialed in there. Other teams have gone to where, you know, they might only make a few P2 posts a month, which if you're doing that, you're not using it for daily communication, you're not using it for real-time saying what you're doing and keeping people up to date, using more like one-way announcements.

This raises the question of what skills are necessary to succeed inside of Automattic, because I think there is a little bit of a— with, with P2 being so central and with written communication being so central, and the fact that WordPress.com is a website and blog hosting platform, that a lot of the most successful elements come around being able to blog internally as well. Do you believe that's true?

I try to be pretty active on P2s. You call it an average, maybe 100 posts and comments per month. And my total word counts, I think it's over a million words now that have been posted to these internal sites. And it's really one of the richest treasures I have in my time at Automattic because everything is archived, everything is searchable, everything is there. And if I need to remember what I was thinking in 2012 when we made XYZ decision, hopefully that decision is documented and the debate around it, and it becomes this huge source of wisdom, which I think allows the company to evolve in a more informed way. And we try to only make new mistakes. And having that, the entire kind of history of the discussions and collaboration that led to where we are today on these internal blogs, I think allows us to move faster, smarter, and better. As we blaze a new trail.

I mean, it raises some other questions just about sort of talent. And one of the great promises of distributed work has been the idea that we can find talented people all over the world. But there, there are also trade-offs to what skills and talents this culture prizes versus, say, an in-office culture, maybe that's more extrovert-focused or verbally focused. What would you say the major trade-offs are, and are they worth it?

As I said, different teams work different ways. So there are teams that do very little written communication and communicate mostly through Zoom or audio or things. And so a nice thing about Automattic is whatever your work style is, you can generally find a team that matches that. If you want to be on the team that uses IRC and then, you know, basically never has any Zoom meetings, we got that. If you want to be on the team that has daily standups, we got that too. And so by switching teams or divisions within Automattic, you can get what might— you might need at a different company, to switch companies to find kind of your ideal work and collaboration style.

You've mentioned here, if a team wants to experiment with something, what are the experiments that you have maybe heard about recently that we haven't tried inside of Automattic that you think we really should prioritize and try?

One that's come up is InVision, which is a distributed company, actually has everyone work East Coast hours. I don't think that would be right for our entire company. We're already too distributed for that. It'd be interesting if a team which is largely American-based agreed to overlap the exact same hours, if they would find that beneficial or just inconvenient. And so that's how I'd want to approach any of these experiments, is say find a team, you know, at least 10 people, 15 people who want to try something out and see how it goes, and have them do it for a fixed time period. Do a premortem, do a postmortem, see what are the learnings from it, and then what are the next actions we want to take from those learnings.

Is there enough creative tension or friction in a distributed company that maybe some form of self-censorship takes over, or we're too polite with each other and we don't raise the questions we need to raise? Do you think that's a valid concern?

This is why I've become kind of relatively recently obsessed with the idea of an idea meritocracy. Have you read the book Principles by Ray Dalio yet? It's a really impactful one in that you're not gonna agree with it, but it'll make you think differently. And you know, one of the things he emphasizes is even in their, in office culture, that the comfort that people have with challenging ideas and the openness people have to their ideas being challenged is crucial to getting the best outcome. Because if either of those is missing, I think you get subpar outcomes. And I think that because when you're communicating on text, it can be so easily misread, people hold back. I do think that's 100% true. It's less bad on audio or video, but definitely in text communication, you just don't have that nuance. All the emoji in the world can't recreate the kind of timbre and tone of voice and all the sort of additional data we get when we're actually talking or seeing each other. I think a lot about that, and I've been thinking a lot about how to foster that. You know, Google talks about psychological safety being key to the high performance of teams. How to foster that where we think that good ideas can come from anywhere and everyone is comfortable presenting and defending vigorously anything they believe in.

One other thing I'd like to do real quick is just do a quick speed round and equipment breakdown. Tell me a little bit about your workspace. Now, you travel a lot, you're in a lot of different cities. Tell me a little bit about your must-have items.

Yeah, check out the What's in My Bag post for the kind of things I use every single day. You know, it's the 15-inch MacBook, it's the cables, it's the, the Sennheiser headset for being on calls. I really find audio quality is far more important than video quality for creating a great meeting. At home, to me, that's like the ultimate luxury. My favorite part from being distributed is when I am able to work from home, which is probably a minority of the year, but I love it because you can have your music you like. I like having a candle on the desk. I like the temperature to be a little bit warmer because when I work, my hands and feet tend to get extremely cold for some reason. Normally they're fine, but for some reason when I'm on the computer, they get like ultra cold. I At home, recently installed the instant hot water thing, so in my sink I can get kind of near boiling water and make tea. On my desk, I always have a notebook. I love paper notebooks for writing things down. I find it's a lot less distracting than trying to type things out. Or for a while, I used to try to have desktops like an iMac, and in fact the new iMac Pro is— still have one of those in Houston. But I've really gone to where like a great monitor plugging into the 15-inch is kind of the easiest And I love these new ultrawide monitors. So LG makes some. I think I have one that's 34-inch and one that's like ginormous, 38 inches wide and curved. And using that, it feels like a panoramic experience. I knew that I was, uh, spending too much time on Google Spreadsheets— Google Sheets— when I was like, oh my goodness, and I like stretched out the sheet all the way to the 38 inches of this ultrawide monitor. I was like, I can see everything. Felt almost omniscient. But I was like, I'm in spreadsheets too much. I need to load up some JavaScript. When I'm at home, I use a Logitech Brio camera, which is kind of a high-end 4K webcam that they have. I find it has a much better aperture, so it creates better colors and kind of light in kind of low-light situations, which is often where it is. If I don't have good natural light wherever I am, I have some desk lamps, just kind of soft light that I can put there so I don't look kind of weird or backlit wherever I am. If I'm on video, I try to— I actually think of it probably much like a webcam YouTuber would, like, what's the lighting like, what's the audio, how can I, uh, present well there in a professional manner. And actually see a lot of folks in Automattic kind of curate their backgrounds, you know, having like things they like in their background because you, you actually end up looking at yourself, what's behind you, a fair amount when you're on Zoom or Hangouts or one of these things.

Couple quick speed round items: phone calls, love them or hate them?

Huh, it's actually a resolution of mine to pick up the phone more. So I don't really receive phone calls because it's all spam now, but, um, I love all the non-phone things like FaceTime Audio, Zoom, Slack Audio is actually really good. And one thing I'm trying to do more is actually switch mediums. So if I'm finding I'm having a long text conversation with folks, I try to bounce to audio. And it's also nice in that some folks, like my mom is getting older, sometimes it's hard for her to read the text. So it's always really nice to hop onto that. Video is really nice too. I got my mom one of these Google Home devices, had a built-in camera. And so you can use Google Duo. It's actually the only reason you would ever use Google Duo to make a video call to her. And it kind of lights up this device that's by where she usually hangs out. So I found that's been actually really, really lovely as a way to kind of drop in and stay connected with a loved one who I don't see as often as I would like.

Final question: 20 years from now, what percentage of jobs will be distributed?

Turning my questions back on me. I'm going to say— well, I kind of don't want to say so that future guests can answer this without knowing my answer. I do believe there's a window where distributed companies have a real advantage. For recruiting, retention, everything. That window is probably 3 to 5 years before the incumbents really embrace this. I then think that job seekers are going to learn to ask more sophisticated questions. So they won't just say, can I work from home or not? They'll really dive in to where decisions get made, where the center of gravity for the organization is. Can their career advance as much being not where the headquarters is or in a distributed fashion as it would if they were, say, in Mountain View at Google? And those type of more subtle questions will be the things that, as the internet giants embrace the surface of distributed work, but perhaps not the deep spirit, all the things that are currently bundled with that, and startups like Automattic or Envision or Upwork— I guess, are we still a startup? But companies like that, the bar will change. I'm looking forward to that happening.

Thank you, Matt.

It's been fun chatting.

That was Matt Mullenweg. Thanks again, Matt, for taking the time to speak with us about the past, present, and future of Automattic. If you want to read more from Matt, you can always go to his blog, ma.tt, and he's also @photomatt on Twitter. That's photo, P-H-O-T-O-M-A-T-T. Thanks for listening.