The Exchanges

Q Yeah, and the business model was basically free. It was free to use, like Dropbox, right? Anybody could just go to WordPress and start a blog, and it was, they didn't have to pay anything.

A Yeah, but we couldn't, we knew we couldn't handle the demand at the time. If too many people signed up, the thing would fall over, because again, it's just... It's a couple of, you know, old servers patched together with duct tape and everything. So we created a golden ticket system, and basically it was an invite system where you could get granted this golden ticket, like an homage to Willy Wonka, and that would get you access to start a blog on the service. Right. And then these tickets started to sell on eBay. So people would get the free ticket, and then they would start to list it or sell it, and tickets were starting to sell for like, 9000 dollars, 120 dollars on eBay.

AI assessment note: “we knew we couldn't handle the demand at the time. So we created a golden ticket”

Q So this, this open source platform, B-II, I guess, this guy, Michel, who, who was the, the sort of lead programmer, he left, and I imagine it was a tiny little group of people, because they stopped, they kind of just stopped developing it, right? At a certain point, this is around 2002?

A So what happened was, there was other contributors, like myself and others, um, But Michel kind of had the keys to the whole thing. He was the lead developer. He was, you know, what we call, and open source is often a term called, like, benevolent dictator for life. And so, yeah, it was a little bit of a mystery where he went. And basically what happened was I, I was literally blogging everything on my mind at the time. I was a huge overshare. So I did this blog post I called The Blogging Software Dilemma. And I said, you know, that I really wanted something That was different than anything else out there that assisted the market. I wanted something that was really beautiful with great typography, like this system called text pattern.

AI assessment note: “there was other contributors, like myself and others, um, But Michel kind of had”

Q How did you begin to attract people to adopt your platform, to adopt the service?

A It was really all word of mouth. One thing we did at the time was every website running WordPress, by default, in the template, it would say, powered by WordPress. And so, when you visit a website you liked, you would see this link and be like, oh, let me click on that. And then you'd be like, oh, I could run this, I could do this. Also, I would just go to different blogs, and whenever I saw someone blog about, ah, my website's getting really slow, like, I'd be like, hey, I'm working on this thing called WordPress. You should try it out. It's really fast, and if you want to use it, I'll help you move over, or like, I was kind of just one customer at a time going to every blog, every website I could, and evangelizing it.

AI assessment note: “It was really all word of mouth. One thing we did at the time was”

Q So how did you start to raise money?

A So, actually, the journalist named Om Malek, who was one of the first users of WordPress. He was a blogger, but also wrote for, like, Fortune, and Forbes, and Business Two Point O, and all these big magazines. So he introduced me, again, as a 20, twenty-one-year-old kid, to, like, people like these investors, and people who had built companies before. And one of them was this guy, Tony Schneider, who had actually just had one of the biggest startup sales at the time. He had sold his startup to Yahoo, and so Tony and I met, we hit it off amazingly, and then I talked to these investors. But honestly, if I hadn't met Tony, I wouldn't have raised money, because at the time, the model was not like, if you're the founder, you run the company forever, like Mark Zuckerberg.

AI assessment note: “he introduced me, again, as a 20, twenty-one-year-old kid, to, like, people like these investors”

Q You know, I'm curious because as you were growing and becoming more and more, you know, widely adopted by bigger and bigger companies as the, sort of, their websites, and you presumably are seeing these big tech companies with these big offices in San Francisco, and did you guys have a big office that you set up in San Francisco?

A It was really just Tony and me in San Francisco. And we couldn't afford, or it wasn't economical, or good for the people, to move everyone to the city. You know, it cost a living. Even then, San Francisco was way more expensive than pretty much every other place in the world. And to uproot, like, Danica from his family in Blarney just seemed strange. And, and we'd have to deal with immigration. It was just, like, it didn't make sense. So we were doing something that was really heterodox and revolutionary for business. But actually that open source projects I've been doing for over a decade, which was just bringing people together to collaborate online. You didn't need to be in the same office to work on the same code together.

AI assessment note: “It was really just Tony and me in San Francisco.”

Q And so was the idea at the time, the idea at the time, 2006, 2007, was not to, or was it, was it to, was it to power the internet? Was it For, for every webpage to be a WordPress webpage, or at that point was the idea still, let's get people blogging. Let's help it, make it easy for people to blog.

A That was when we first started to think that it could be pretty popular. Google had done this survey, published a survey of the internet. It was kind of like a statistical analysis of all the websites that were in the Google index and the code they used. And there was this part of the report that said, yeah, and then on .8% of websites, we found this weird HTTP header that was x-pingback. And, uh, me and the other WordPress developers read that, and we freaked out. We were like, oh my goodness, that's a special piece of code that WordPress adds to its site. And, uh, so we were like, wait, does this mean that WordPress sites are .8% of all the pages in Google?

AI assessment note: “That was when we first started to think that it could be pretty popular.”

Q You left San Francisco, moved back to Houston in 2011 because you could. It didn't matter where you were, I guess. You have never, I mean, do you have offices? Do you have physical offices in cities around the world?

A So basically what's happened over the years is we would try to keep a small meeting space, and then often when we would acquire companies, they would usually have an office. Usually what happens is when the company joins, we acquire them, they say, oh, we really need their office. We say, okay, we'll pay the rent, we'll keep it going, we'll keep the lease going. But then once they start to learn our way of working, fewer and fewer people go into the office until at some point they're like, hey, yeah, we don't need this anymore. If we want to get together, we can always rent a Airbnb or conference room. And so, right now, we still have a New York office, kind of the, the vestiges of the Tumblr acquisition, but, ah, that has happened with, yeah, literally every company we've acquired. It even has happened with Tumblr.

AI assessment note: “right now, we still have a New York office”

Q it's not a one-time event that you, that you experience. But you wrote about aftershocks of grief that lasted a long time. It may still come up now and again. A song, just a drive, or just seeing somebody or something would just remind you of him. Um, did you take time off of Of work? I mean, what were some of the ways you kind of dealt with that?

A Part of my grieving process was this feeling of helplessness that terrified me, and part of what allowed me to feel in control was I really dove into work. And it was a, uh, it was a real solve for me. Salve? Solve? Um, something that sort of comforted me, you know. Um, there's this quote from Simone George that says, uh, grief is a raging river. You have to get in to get to the next place. But it wasn't until after he died that it hit me, that things weren't gonna go back to normal, and I had to get in that raging river, and it, um, it was really, really overwhelming. And then I couldn't look at that computer. I couldn't, I couldn't do any of that stuff. So the thing that had been a, a solve for me, um, while he was in the hospital, I just didn't have the mental capacity to, to think about. So it was almost like I was leading a dual life, where sometimes I would be almost like a machine, You know, just kind of like, coldly pushing down all the emotions and all the, everything going on and trying to get something done. You know, be strong for my family and everything like that. And, uh, and then other times I just like, uh, yeah, just break down.

AI assessment note: “part of what allowed me to feel in control was I really dove into work”

Q You became CEO in 2014 after really working under Tony for, I guess, at that .7 years. What did that mean? I mean, was that a really a significant change in the way you lived your life? Because I'm assuming your fingers were not, you know, you weren't in the kitchen, so to speak, as much anymore once you became CEO.

A I was still writing code, yeah. Um, basically, so we did the Passover of becoming CEO, actually the day after my third day's birthday. And part of what had happened was, you know, I had been working with him for, I'd known Tony for eight or nine years at that point. We'd been working together at the company like seven years. And he was teaching me. Like, he, he enjoyed being, leading small things, and WordPress was getting a lot bigger. I was really passionate about bigger things, and growing, and getting to scale, taking us from 100 to 1000 to 10,000. And then Tony actually stayed at the company, which was really powerful. So he, he demonstrated something that's very important to automatics culture, which is like, you don't always need to be the lead. If someone else could be a better lead, you should pass it to them, and you can still be at the company and find something that you're passionate about. So, he, I went to lead a smaller group, a group, basically like an R&D group that's creating new products. And, uh, did that for, I think, another seven or eight years after stepping down as CEO.

AI assessment note: “I was still writing code, yeah.”

Q How long did it take before Google reinstated WordPress?

A So, people were saying really terrible things about me. But as I was reading it, I was also starting to see the truth. I had really screwed up in a big way and betrayed trust. And so first I just posted a mea culpa, and I said, literally, what happened? Like, hey, I've been offline. Sorry, I totally missed this. I did put these links on there, and I took them down immediately. So kind of in breach of the agreement I had with this guy to keep the links up. And, uh, you know, it's funny. The guy who did this was actually kind of nice. So I contacted him. I was like, hey, I can't return the money right now. I already spent it, but like, let me, you know, give it back to you over the next few months. And, and he was actually really nice. He was like, you know what? Don't worry about it. Um, keep the 2000 dollars for this month. And, you know, sorry. He basically said, sorry, you got caught. And, uh, but I posted this big apology. And, uh, And yeah, eventually Google, uh, forgave me. So they forgave WordPress, and they put it back in the search engines.

AI assessment note: “eventually Google, uh, forgave me. So they forgave WordPress, and they put it back”

Q of wrote about this stuff, and you're still a student. This is about, a little over a year after you and Mike Little started to put this together. You got an offer, a job offer from CNET, which is still around. It's like a website. They do reviews of technology and stuff. Um, and they, they wanted you to come Work for them. What do they want you to do?

A Well, kind of what happened was I had set this sort of goal to be the number one result on Google when you search for Matt on the internet. So that what that meant, if you typed in Matt and pressed, I'm feeling lucky, that button on the Google homepage, it would just take you directly to my website. And so every install of WordPress had links to all the main developers. So because these thousands and thousands of websites were all linking to the word Matt, that would make Google think, oh, these websites, you know, Photomat.net, et cetera, is the number one site for, for people talking about Matt. And so we started to rise up in the rankings. And I think at one point, pretty much all of us were the first results for our names online. So when this happened, there was this conference in Texas called South by Southwest I'd gone to. I'd met a lot of really cool people from San Francisco. And one of them, a browser developer named Tantechelik, Said, hey, come out to San Francisco. You can crash on my couch. And so my plan was to go to San Francisco and couch surf. And so I just said, hey, I'm going to be in San Francisco, you know, August one to August eight. And if you want to hang out, here's my email and here's my phone number. So

AI assessment note: “Well, kind of what happened was I had set this sort of goal”