The Exchanges

Q How do you think about your day and organizing it to make sure that you're working on the most important things?

A I roughly think of my time in three buckets. I try to spend about a third of my time on people. So that's either hiring or internal HR. I think this is the environment work, creating the environment for people to thrive and do the best work of their lives and their career. Spend about a third of my time, particularly right now on product. So I'm sort of temporarily running our largest product, which is wordpress.com. And so, uh, I'm a lot more in the, And the weeds there in terms of, you know, working with the leaders and engineers and everything to make sure that's an excellent experience. But more normally, I might float a little bit more between the different products across the company. And then finally, that final third, I just try to reserve for whatever is the emergency of the week.

AI assessment note: “I roughly think of my time in three buckets.”

Q Thanks to you, that was, uh, possible, so really appreciate that. How did WordPress get started? Like, what's the origin story behind WordPress?

A Gosh, WordPress came out of sort of a passion. I was blogging and found the software called B-II to, essentially, I found it as, like, the most customizable, uh, blogging software out there, but it's very small. The dominant one was called Movable Type, which is kind of like a static site publisher. Probably had 95% of the market, but I like B-II. And I started, like, Volunteering on the forums and writing little code patches for it and like helping other people. And so got involved in that community, which I've always found the most exciting part of building things or being online is being part of community. And when the software kind of got abandoned, um, I blogged about that and said, I'd love to see something that combined the best. I think it was the simplicity of blogger, the customizability, or the power of movable type, the elegance of text pattern, and the hackability of B too. There was four different blogging platforms at the time. So kind of tried to combine all those things. And this fellow I'd never met in the UK named Mike Little was like, hey, if you're serious about this, let's work on this together. He was another volunteer on the forums and things. And also a real developer. I was like a, a 19 year old kid in Houston. He was a professional. And, uh, so we just started hacking together, coding together. And that turned into WordPress.

AI assessment note: “we just started hacking together, coding together. And that turned into WordPress.”

Q Can you expand on that a little bit? Yeah.

A So open source is kind of like software with a bill of rights attached, right? Like in the United States, I know you're Canadian, so I apologize, but you know, the bill of rights essentially ensures certain freedoms, uh, most famously like freedom of speech being the first amendment. Uh, for open source, there's what's called the four freedoms attached, and particularly the license we build on, which is the GPL. Because they're geeks, they start counting from zero. So freedom zero is the freedom to use the software for any purpose. This means no one can tell you what you can or cannot do with the software. If you wanted to make a WordPress suck site, or Shaneisawesome, or fs.blog, or literally anything, no one can tell you what you can or can't do. Freedom one is the ability to see how the software works. So to be able to open up the hood, see how it operates, which, you know, if you're going to operate from first principles, or you want to understand how something works, you need to see what's under the hood. And so much of our lives now are essentially digital black boxes. Like we, We have no idea what's going on. And more and more, as more and more of our lives are influenced, you know, who we date, when we meditate, what we pay attention to, what news we read are essentially these black box algorithms. We are losing our agency and sovereignty over ourselves. So being able t…

AI assessment note: “open source is kind of like software with a bill of rights attached”

Q You mentioned something earlier about how you guys are distributed, and you didn't use remote, you used distributed. What's the distinction there?

A Words create reality, and we obsess a lot over what words we use to describe things. Um, I think we used to use remote to describe what we were, like, hey, we're a remote company, or remote first company. And I realized, like, who wants to be remote from their colleagues? Remote implies that there's, like, something central, and you're far away from it. You know, there's a remote mountain, or you're in a remote town. You're isolated. What's a lot closer to what we were trying to create was essentially an anti-fragile, fully distributed organization. That each node on the network was at an equal weight with each other, and just like a great network design with, like, BGP failover or something like that, like, the, the, or the system itself becomes quite resilient because the nodes are relatively independent, but each able to fully contribute. So, For us, we shifted to being, calling it distributed and really talking about distributed because it's so important that every single person in the company has an equal ability to contribute.

AI assessment note: “Remote implies that there's, like, something central... distributed... each node on the network was at an equal weight”

Q So that's really interesting, right? Because that sort of leads me to speculate that environment matters a lot to how people perform. Is that something you think about?

A I think it's the most important thing by far. Yeah. So like in running a company and running a community with WordPress, um, we're obsessing over the environment we're creating. And I think there's a microcosm of that. Like think about the environment around you in your office or where you're working. The smells, the temperature, the lights, the inputs, the music, everything contributes to how you're operating. And companies have equivalence of that. And, uh, communities have equivalence of that. You know, in WordPress, we have, you know, five, 10,000 people contributing to WordPress on a regular basis. Uh, now what sort of environment is happening there? We have something happening right now, which I think is fairly unique and exciting for open source, which is WordPress. 5.6, which is coming out, uh, fairly soon is an all women release lead squad.

AI assessment note: “I think it's the most important thing by far. Yeah.”

Q I want to talk a little bit about the differences between public and private. You just mentioned doing this five-year big infrastructure investment. Is that something that you get an advantage of being a private company where you might have more scrutiny if you're a public company? How do you think about that?

A Um, I think it's about clear communication and expectations. So we run things internally, like we're a public company. And, you know, I could see a future at some point when Maybe all of automatic, or maybe one of these like subsidiaries, one of these like subs, um, could go public on its own. But, uh, I actually don't buy the thing that, that public markets don't reward long-term investment. And I think there's some amazing counter examples of that. Amazon perhaps being the best one, where if you clearly communicate and do what you're going to say over the long term, these long-term investments can really, really pay off. And, you know, what's the thing in the short term? Voting machine, long-term weighing machine.

AI assessment note: “I actually don't buy the thing that, that public markets don't reward long-term investment.”

Q I remember, I remember that from back in the, back in the day. How amazing was that? Like, that's an arms race though, like blocking spam. Well, like talk to me through that, through the comments and trying to figure out if it's like a legitimate person or.

A Yeah, it's actually one of the things I'm most proud of. Today, we'd call it like a machine learning AI system, but at the time we didn't. And it's now, 10 years later, it still has over five nines of accuracy for blocking spam and, and keeping, um, and allowing good stuff through. So it's essentially like basically, again, it's all about markets. Markets always trump anything an individual company could do. And there were all these solutions to blocking spam on sites, but they would only work for that one site. And of course, what happened is the spammers would tweak their code and, and it would start working. Um, so we created a system that essentially allowed all the kids being bullied on the playground to work together and to gang up. And of course, that's what makes humanity great is our ability to collaborate. So we started collaborating against the spammers. And so they would adapt very quickly, but the network would adapt in real time to their changing tactics. And in particularly with web spam, typically web spam is trying to direct either a search engine or a person to a place. So that provided a really great avenue of, um, well, you know, a ton about security of being able to target these because ultimately they didn't just want to, you know, they didn't want to rank first in Google for V one G R four, right? They wanted to rate first for fire or mesothelioma or what…

AI assessment note: “so we created a system that essentially allowed all the kids being bullied on the playground to work together”

Q What are some of the blind spots you've uncovered working with a coach this year?

A How limiting my communication can be sometimes. Even sometimes how I'll ask a question from a place of perfectly good intention can put the other person in like a, not a victim mentality, but in like a mentality where I'm solving things for someone. Like I can play the savior role. So, and it can be very, very subtle. It's like, is there anything I can do to help you? Versus What do you need for this to be a success? One is like putting the power with me to help you, and the other is putting the power with you to define what you need, and then I can support that, but ultimately you have the agency, which is far more empowering. I've been learning and working on, and by the way, Nonviolent Communication is an amazing book, NVC, which has a terrible name, but it's really valuable. Uh, that was not with his coach, but was a game changer for me a few years ago. The other is like, I feel like for most of my life, I kind of treated myself as like a brain in a jar. So like this disconnected intelligence that, you know, I'd invest a lot in exercising my brain, but not anything else, but also not really listening to my body. And so something I've been working on a lot is trying to listen to you, to whoever I'm speaking to, but also listen with awareness of what's going on throughout my whole body. And that's been kind of amazing. You know, just this idea that, you know, maybe you can na…

AI assessment note: “How limiting my communication can be sometimes. Even sometimes how I'll ask a question”

Q So the cross pollination, is that how you influence the culture? Like it's not a top down, we're going to slowly nudge this a little bit differently. It's more like we're going to place people at different levels in the organization, or is it the same level? Is it the top? Is it the bottom?

A Like, I mean, people is by far the most important thing because the people, everything else flows from the people. So, uh, you definitely want cross pollination of people. Um, in terms of technology, um, I don't feel like you can force engineers to do things that they don't want to do. So that's much more like, ah, showing the benefits. The only places where we'll do something really top-down is if there is a, a really large capital impact. I think it, it probably would have been a little bit easier just to completely recreate, you know, buy the 6000 servers that they had before and buy the exact number with the exact configuration in our data centers. We ended up reducing that to about 800. So we went from 6000 servers to 800 and part of that was, you know, doing a lot of engineering work to bring things on to sort of what we've learned with best practices and being super duper frugal with everything we build. And, uh, so it took a little bit of work, but it just saved so much that it made sense to make that kind of like, no, we're absolutely going to do this decision.

AI assessment note: “The only places where we'll do something really top-down is if there is a”

Q As somebody who, who's super thoughtful, you always think of the drawbacks to everything. What are the drawbacks to distributed and entirely distributed workforce?

A Uh, I totally get jealous sometimes when I walk in my friends' companies, and they just have these amazing offices. Um, not so much for the physicality of the office, although sometimes I do appreciate good design there. But just, I, I love my colleagues. I really enjoy spending time with them. Particularly this year, I wish I could do more. A secret sauce, a magic ingredient of our distributed approach, is in normal times, we get people together three or four times a year. So if you joined automatic and say, Shane, you know, uh, as part of, you know, deciding whether to take this job offer or not, expect that you will be traveling three to four weeks per year. So you'll be away from home. So, you know, whether that means you need to find like, you know, a cat sitter or someone to watch your kids or whatever, like you're going to be on the road four weeks out of the year. And one week, historically, we've brought the whole company together. And then the other two or three weeks, you're going to be with your team, which is typically, we have lots of cross-functional teams, typically five to 10 people. We try to have every, everything on the team that's needed to ship something to users, and so they can operate in a fairly autonomous fashion. And, ah, you know, when you're able to, as humans, I still think there's something that is Impossible to recreate online, which is that bre…

AI assessment note: “I still think there's something that is Impossible to recreate online”

Q I want to come back to the reading here in a second, but what are some of those subtle changes that you're talking about that you're, you're thinking of?

A You know, this has been a year of incredible acceleration for our business because as the world economy and everything shifts online. Our e-commerce business with WooCommerce, the blogging side, the site creation with WordPress.com, even users of Tumblr grew. And so everything, ah, was up at a time when I would say our, my colleagues were, are impacted. So I feel like we were operating probably even still at like a 70% efficiency of what we were pre-pandemic. And that is largely, you know, the, oh, it's, it's everything that you can think of. People are literally getting sick sometimes, or they have loved ones that are, that they need to care from. The impact on folks who care for either elderly or children versus, you know, has been really disproportionate, I think, in this, uh, this year. And so I've seen a big, big impact for folks, like four kids at home, trying to homeschool them. Like, you know, this has been really challenging. Uh, so we're not operating at our peak. Uh, what's funny is other organizations that have been switching to distributed have been talking about how they've gained 15 or 20%. So my theory is that we were at like a hundred percent and we came down to 70. They were at like 50% and they went up to 70.

AI assessment note: “we were operating probably even still at like a 70% efficiency”

Q How do you frame that? Is everything time boxed? Like you said at the start, we have 36 hours to make this decision. Like, what are the parameters that you put along that so that it doesn't just spiral out of control, and how do you differentiate between decisions that need to be made as soon as possible, and maybe larger strategic decisions that can be as late as possible?

A I think sometimes we do this poorly, by the way, so there's definitely threads that get started, which don't have a clear goal or outcome or time limit, and they can just meander on for days or weeks, and then you come to it later, like, oh my goodness, what is this? It's like 15, 20,000 words. Like, how do I decipher this? I'd say that very much automatic is a written communication culture, and I believe clear writing represents clear thinking, and we filter for this in our hiring, and we, we talk about writing a lot, so we like Invite writers and we talk about books like On Writing Well or Words That Work to like get people to be clear written communicators. Some of the things I'd recommend other companies try that we've Come to. Uh, you know, let's say there's, there's a doc, a post which is presenting an idea. Um, a very common pattern is a TLDR at the top. If you're not familiar with that acronym, it's, um, TL semicolon DR and it stands for too long, didn't read. And so essentially oftentimes people put like a little tweet late summary of whatever they posted at the very, very top. Um, actually, so some way, you know, you asked about Tumblr culture influencing us, they introduced a new acronym to this, so they'd have the TLDR, then like a chunk of text, and then they had like, ah, it's escaping me right now, but I feel like it's like GSGM, like, good stuff, give me more. A…

AI assessment note: “I'd say that very much automatic is a written communication culture”

Q Tell me a little bit more about Automatic. Like, what do you guys do?

A So Automatic started actually 15 years ago. I just celebrated my 15th anniversary with the company, and the idea was to essentially create a company which, uh, tried to build and flourish from the open web and open source. So we wanted, I wanted to create a place where I could work on open source full time, And all the other developers of WordPress and others could benefit from it. We also wanted to create a company, a for-profit, that was paired with a non-profit, where each one would be stronger than either would be on its own. So I think non-profits can do awesome things. I think for-for-profits can do awesome things. But with WordPress, we have essentially WordPress.org, which is open source software, which is not owned by Automatic. We have Automatic, which creates services for WordPress.org. And then there's a huge ecosystem outside of that. You know, WordPress, as you mentioned earlier, has some of the most incredible market share, and that's been very rewarding. But automatic, the company actually has smaller revenue than, than other companies that you've probably heard of, because we only make a few percentage of the dollars in the WordPress ecosystem. So, uh, we've always targeted, and I got this, there seemed to be sort of a law of platforms, um, going all the way back to like DOS and Windows. If you look at like the launch of Windows, one of the things Microsoft wou…

AI assessment note: “We have Automatic, which creates services for WordPress.org.”