Interviewer: So, hello Anil Dash.#

Dash: Hello.#

Interviewer: Let's start with something easy. You probably get asked it a lot. You've been blogging for quite a long time, so I was wondering how you first got into it.#

Dash: It's hard to even remember. I was fascinated by the web itself and how it was being made and I wanted to learn how to make webpages and that sort of thing. I kept noticing that the sites I was really fascinated by were these sort of personal sites, these were the proto-blogs of some of the earliest ones, I think. The names I remember, Peter Merholtz, who would later go on to coin the word "blog," Jesse James Garrett who had assembled the first sort of list gathering, collecting, all the blogs together. Michael Sippy who had done a really simple set of question/answer blog posts that stuck with me as an early example. And a lot of other folks like that, but those were the kind of people that inspired me to start. And I literally had a long commute and I started just doing HTML on my laptop on my own without... and I didn't even put it on the web... just to kind of learn. And after I had been doing that for a couple of months, I realized I really like doing this. Really simple, sort of embarrassing website design, but I had it, I had my domain, dashes.com, and I just put it up there. And I didn't tell anybody about it for like, months. But it was a small enough world where people would see if you clicked through a link from your site to theirs, they would see you in their referral log. I remember, I had probably been going for a few months and Jason Kottke linked to my site and that was a huge deal. It's funny because we're close friends now, it would be embarrassing to admit how excited I was. But it was like being discovered. Now everybody knows who I am. Also, I felt very much a sense of being late to the game because there were dozens of other blogs. So probably everybody had written about everything. That was really the start. And almost immediately, I started in June or so, actually publicly publishing my stuff, actually June of '99, and Blogger came around in September. I loved it as software. I think I was the first user of Blogger outside of their core team. I just signed up for it as soon as I heard about it and wanted to try it out. I just thought, wow, what an interesting category of application and Blogger looked very much like [3:00], it looks like Microsoft Word. The buttons looked like the toolbars in Word did at the time. I had for many years made a living programming Microsoft Word stuff and Microsoft Office things for clients. So that was like this light bulb went off in my head of like applications. You can build apps on the web. That was like crazy. And that those apps... like ???[not sure what was said here] it's really obvious now but that idea of a content management something, a system that could be human used was like this epiphany for me. I was the biggest Blogger fanboy. Literally, from almost the moment Blogger launched, I kept like a fan page about Blogger that was like all the public information that people knew about Blogger Pro and read about all the exploits of all the founders... and again it's like... it's very... it's awkward now because I'm friends with all of them, but at the time I was just like these are my heroes and I wanted to see what they were doing. And I was really excited about it. I thought Blogger was going to do Blogger Pro and charge for their product. And I kept a big product page about that. And I was like I'm going to be the expert on this thing.#

Interviewer: So how come you then became the expert on Moveable Type as opposed to Blogger?#

Dash: Blogger was interesting because they ran out of money... well they did the server fund, they ran out of money, the team left, and actually most of the people I had known were gone, so Evan was the only one left, and I actually didn't know Evan as well then as I knew other people on the team, so I sort of just felt like the opportunity is gone. And Evan had been somewhat chastened by how negative the community had been about that. And so there wasn't really... we didn't really after that point know what was going on with Blogger/Pyra as a company. You just saw the product. So I was using the product and actually continued to for a long time and then it was just, you know, they were struggling trying to keep it running. So there weren't any features, and there weren't, like we had all these ideas of what we could do with the medium, and we were hacking them together ourselves. So I wrote a little commenting script for my site, and I was using someone else's script for showing who was linking to you, and all these different pieces and some of the very early tools, like GreyMatter, were starting to get some users and I remember trying to set it up and it was incredibly hard and just ugly. Part of it was, gosh I have this thing over here that looks like Microsoft Office and all these other things look like, you know, somebody wrote them at the command line. So that was a big part of it. I remember finding Mena Trott's blog and she started it on Blogger. At the time, I guess just because I was a fanboy, [6:00] they had made me a guest editor of "Blogs of Note" which was like their featured blog on the home page of Blogger. I don't remember if it was me or Evan or one of the other editors, but one of us featured her blog and that was how I found it. I was kinda like clicking through. And the interesting thing about that is, at the time, if you were on the home page of a recently updated site for Blogger or the "Blog of Note" that was a really great way to get discovered. Like you were a star. These days, if we see something featured on the home page on iTunes, of course that must be a big record, right? But it wasn't very obvious then. So I found Mena's site and we would just comment on one another's blogs because we had a similar sense of humor. By summer of '01, and this is... keep in mind, this is two years after I've been blogging, so I was like an old-timer, I thought she was a newcomer,#

Interviewer: I love that!#

Dash: Totally. I was like, oh this is this new wave of bloggers and she was great at it. I mean like, really... production values, and she's an artist and would draw illustrations and the whole thing. And I was like Wow, this is like another level. And she said, oh you know, my husband's a coder and we're going to build a blogging app. Do you want to alpha test it for us? And I said sure. And they sent it to me, and it was a Perl app and I was a coder, but I didn't know Perl. And I didn't touch it. I didn't touch it for like months. Because I was like, it's too hard and Blogger is so easy and I know PHP - all of these things would probably become relevant later - and so I sort of just left it there. And as they were getting close to release, this is like August or so, I tried it out and I thought it was beautiful. I think in a lot of ways it foreshadowed the web 2.0, not the gradients and things, but just sort of the beauty and the white space. It was the first thing that didn't look like Craigslist or Yahoo! 1.0. And that was just a huge leap forward. And I was so taken with the aesthetics of it and the default, even the default templates, I mean they looked so dated now, but they were such a leap forward over what Blogger was doing by default and what... like I knew HTML, but I didn't know design. And so the aesthetics of it was such a leap forward. And then all of a sudden my blog posts had titles and I could have comments and I could archive things by month and I could do all manner of really interesting things. And all mostly with just HTML. Pretty much as easily as Blogger, but just so much more power. And I was just thrilled and excited about it. And they were like asking everybody to sort of be reserved until it was out. If memory serves, [9:00] they were supposed to launch it on something like September 12 of '01, I think it was right around then. Obviously it got delayed. Actually because they had been getting ready to do it and I had been giving them feedback on the app, both Ben and Mena Trott checked in with me a lot being I was in New York after the attacks. And we really connected on a personal level. Like, I think before that I think I had been testing software. And this was much more of this sort of people make this app, and that was a big leap for me. Because before then there had been this sort of exalted level of Evan and Meg, and Matt Howie and all the people making Blogger were these sort of... oh, those are people that make software. And this was like, oh, friends, these are my friends. And so that was actually a really big thing. The one was that we wanted to do more with the medium and Blogger just couldn't, just because they were under-funded essentially. And two was, oh, these people are like me. They're normal and they're approachable and they're not, you know, those sort of exalted titans of the software industry, or something. Which is ridiculous to say now, but that was the sort of the stakes. And a couple months go by, they launch, and lots and lots of users of Moveable Type, in what felt like those first six months, I'd say late '01, early 2002, first of all what would become to be called the war bloggers showed up, so there was a huge influx of people who wanted to have a voice that were nothing to do with technology, nothing to do with HTML. Really radical. And it was like exciting, thrilling, but also kind of scary because they were politically very different than all of us had been very, very liberal. It wasn't so American any more, which was great. So we started having people saying I want to write in Arabic, I want to write in Japanese. So there was a lot of really interesting... and just like any new thing, and I think this was sort of very much like the birth of any medium, there was just enormous creativity. And to some degree, it was all centralized in one place because there weren't any other tools. Right, you could have Blogger, if you truly just didn't care you just wanted to get up and running. And if you had to do anything slightly more, like just comments, or anything, there were people saying okay just use Moveable Type, I'll set it up for you. And that was it. It wasn't like you could set it up. It was like, I'll set it up for you. But that rush was there. And it was interesting because LiveJournal had come along the year before and that was like, oh those are journals. Those are very separate. And in '99 they had Pitas and DiaryLand which often get overlooked, but were huge, were hugely influential. And actually were sort of too big. I mean I remember distinctly being like, oh Pitas is some big community of people I don't know... I'm not going to venture out into that. It all sounds absurd now, but the social factor was a very huge part of it. So how much was like, these are people like me, and they're okay, [12:00] and this is comfortable, and there's cool things going on, and these are creative, or whatever, you know. All those things sort of congeal. At that moment from, they launched in, I think it ended up being October of '01 to six months later at South by Southwest I met them in person for the first time. And everybody wanted to meet them. And they were, Ben and Mena were insanely shy.#

Interviewer: Oh dear.#

Dash: Part of it was they hadn't left their apartment in six months. They'd been coding the whole time. Like they hadn't done anything to make a product. And I met them and they built this tool and it was hugely popular and like basically they didn't say a word the whole time. The last night I'm at a dinner with them at three in the morning and I'm like you guys have an amazing business here. Whatever you want to do. If you want to host it, if you want to do whatever. And they just flat out said no. They said nope we're going to do exactly what we're doing, we're not... like we're never... we don't want to host it. We don't wanna... we're fine doing exactly what we want to do. And I was like, I think you're going to get overwhelmed, and they're like no. And six months after that was like their first year anniversary and they were on version 2.5 which was like the big leap forward, all these capabilities and things, and they were like we're drowning. Everybody in the world wants to use this. We just got a check from some guy in Japan for a thousand dollars. We don't even have a company, like a bank account to put it in. You know, we got an email from the New York Times that they want to work with us, you know, whatever, like all the stuff. And the email from AOL, I remember that coming in, and the person at AOL at the time was John Borthwick, you know, who's now at Betaworks, ... I remember a couple, Jeff Jarvis, who I remember emailing really early on and being like this guy started Entertainment Weekly magazine, like this is crazy, how is this guy using this software? And so many other, and the big one that sort of stuck with us, was like who's this guy, like some friend... first of all, Justin Hall was using the tool was amazing, so Justin had done links.net, the proto-blog, was this extraordinary. It was like, oh my god, like was like... blogging must be real, because Justin Hall is doing it. And so Justin knows some guy in Japan, and he went to Japan, and this guy sent a thousand dollar check for the software. Joi Ito. And that was how he came over the transom. And so all that goes on, you fast forward a bit, Joi actually tried to invest in Pyra. And then literally, I think right after their first conversation, Evan met Larry and Sergei at a conference, so the die was cast. And so Joi said, okay, what else is interesting, and actually, I use Moveable Type so maybe I'll invest in that. And I had just started talking to Ben and Mena about this [15:00] is going to be a company and Joi came along, and I was like, let me help out. And I had gotten laid off, so I was like I'm just going to help you for free because I think this is interesting. And they were off and running. And then you leap forward about a year and a half and we're in the process of like finding a CEO and the investment company that Joi had done had tried to find a CEO and the guy who was leading the CEO search actually became the CEO. Sort of... I guess like Dick Cheney did in the VP search. Not in a bad way, I didn't mean it like that. That's how the process works sometimes. And it was like, okay what's this company gonna make money doing. You know, like we've got the users, we've got the momentum, what are we gonna do? And I had kept my ear to the ground about what blogging software was going on. So GreyMatter had pretty much just given up. It had gotten overwhelmed. I had seen b2 sort of be picked up and dropped again a couple times. I had always found it very interesting because I was a PHP coder. One or two sort of... there was like desktop blogging software. Like Fog Creek had an app, called City Desk, and obviously Dave Winer, UserLand, and that sort of had traction, but sort of... like Dave was so polarizing that it kind of overshadowed the software. And that social factor? We always thought everyone was making a decision on like features or something. It was very... I don't know... naive I guess. Really. Inexperienced. Because we were kids. And so, we were looking at these things and it was like, you know, I think for the short term, we've got this. So what we can do is figure out a way to charge, today this would be very obvious - this is the freemium model - but like charge just the people who are getting a lot of value out of this for some of the software. And the process I did was look at web publishing software. So I looked at like Dreamweaver and Front Page, those were still apps that people bought then, and they were like $500, $1000, insanely expensive. And then we did a survey of our users. I mean it was hundreds of people, it might have been the majority of Moveable Type users, and we said how many blogs do you have and how many people contribute to your blogs? And they came back and it was like 98% have fewer than three blogs and fewer than five authors or something like that. Some tiny numbers. So it was like look, this is a no-brainer, we take that 2% that has a ton, and there were a couple already that had big blogging networks and were growing. Gawker was out there and had made a name for itself and started to sell ads. About.com had switched all their stuff over to Moveable Type and it was like there's some value being created here, we can get these people to pay some money. So we made a pricing scheme that like [18:00] we didn't explain at all, we put it out as part of a really buggy developer release. We had been exhausted just building a payment system. Back then you didn't... you had to build everything. We had to figure out how to handle credit cards. So we had spent months and months and months working on our own with a tiny team, seven or eight of us, building a payment system, building all the infrastructure, like getting truckloads of servers delivered from Dell, and doing all this stuff. And we put it out there, and people lost their minds. They were like... I remember a couple really distinct parts and one was how dare they introduce money to blogging. I mean almost explicitly in those words. Like this was independent media and now you've corrupted it. And to us it was like, look Gawker launched a year ago, with ads on it. And we've got the biggest media companies in the world using this thing at least in some corner of their empire, and we know there's tons of... it was sort of like, that ship already sailed, how could you not know? And then the other part was like well the only other option we would have is to put ads on it. And at that time.. So Google hadn't launched AdWords or AdSense yet, so ads on the web were literally the blinking flash banners, the animated gifs, and punch the monkey, right? So they would have been like GeoCities. And it's funny because literally some of the same people years later were the exact same people saying if you're not paying for the product you are the product. And I think to some degree maybe it just takes a couple of years to learn that lesson, right? Because you have to build an app or you have to be in the environment long enough where you have to see the cycle go. We had just gotten a glimpse a little bit earlier because we had been able to see what everybody was doing. Probably most tellingly, right before we had done that, we had introduced this idea of a sign-in system called TypeKey for comments, and it was supposed to... honestly, we did it for just account management, because we knew we wanted people to be able to pay, so we're like here's an account manager. So hey, you can use it for signing in to comments. And it was like this very old school web. We documented it and you could run your own, and it was an open protocol, and there was no patents on it... every checkbox of openness you could do, but we were also running one on our own. The first response to that had been, like the first blog post that got a lot of traction responding to it was The Patriot Act of Web Logging. That was the headline. In this sort of current era with Facebook and NSA and whatever like, we get the implications, but that was there... and the funny thing was, what we were pushing for was decentralized authentication, so we'd all be able to sign in from our own sites to other people's sites. It was the first sign, in retrospect it should have been obvious, of total disconnect of what we were thinking [21:00] in our heads and what the audience was getting. What the blogging community was getting. And separate from the software. We just got to see it because we had the users that were sort of engaged in blogging. But what did the blogging community care about was like these issues that were geeky and technical and social and had nothing to do with software. And nothing to do with like implementation, you know. And we had thought of it as we are making an app. You would never evaluate Dreamweaver on these grounds. This all comes to pass. First there was that precedent setting with like, we made an authentication system, oh they're trying to be creepy, they're trying to be... those days people would compare you to Microsoft, like Microsoft passport, today they'd say Facebook... and then right after that, we're like by the way we're going to start charging for this, and surprise! And people lost their minds. So for... I remember I was at my desk for about three days straight. I mean we were all openly crying at our desks, we were getting death threats, we were getting... whatever you can imagine. People calling up and how dare you. You've taken the most special thing on the Internet and ruined it. I mean just... savage. And part of it now I realize is, nobody had ever had an audience where by definition every single one of your customers had a blog before. And so nobody had ever had a social media shit storm before. And now we can see... you can see a fast food company makes a stupid tweet, and they have like a checklist. They're like, oh, okay, we fired the intern, we're sorry, it won't happen again, here's the hashtag for how we're going to apologize, we made a donation... like you just run through the list. It doesn't even get attention unless it's something really egregious. But it hadn't happened before. And mostly because nobody else had a lot of customers that were bloggers before. So you might have one. But every single person we'd ever had as a customer was a blogger. With the thick skin of a dozen years having passed, it would be very easy for me now. It would be like we hear you, we're going to respond, we're going to change our pricing, these issues... and what was funny... the thing I went to... Barak Berkowitz was the guy who became the CEO, and he was sort of acting CEO at the time, and the morning after the launch, when it was clear, and we'd put it up like, of course because we were incompetent we put it up at like midnight on a Thursday and then went to bed. And the morning after the launch, I went to him and went look, why don't we just open source this. Like it's already... everybody has the source code to Moveable Type, it's just technically not licensed that way, but we don't care, and then this will solve the problem. They won't feel like we're trying to screw them. And he was like, let's just wait and see. Let's give it a couple of days. And again, this is a really conventional standard business practice that would make sense in a non-social environment. And so we waited, and saw through the weekend, and the thing that was misleading... we made like a quarter of a million dollars in Moveable Type license sales that weekend, something like that. Which at the time was all the money in the world. [24:00] I mean I think we'd raised six-hundred grand in funding. So it was like, wow, this was the most money and of us have ever seen in our lives. Like this pays for all the Dell servers we could want. And it is was like, maybe this worked. We couldn't tell. Like is that good, is that bad? How much money is there? What's right? Of course I was responding in the comments on every single blog post that had complained and saw on every single blog post Matt going in and saying you should try WordPress. And I was livid.#

Interviewer: I bet.#

Dash: I was furious. Part of it was Blogger had fallen down all of the time. Like the servers were super unreliable. But we knew we'd all gotten started on Blogger, so we had never, ever gone to anybody's Blogger site and said you should try Moveable Type. It was funny, because we had the same naiveté about basic marketing that our users had about basic economics and paying for software, right? We thought it was brutally obvious that either you were going to have ads or you were going to pay money. Those were the two things you could do on the Internet to support something. And it is brutally obvious that somebody that makes an app they want you to use is going to ask you to use it. But because of the social context, this was like a... oh, these kids today don't have any respect kind of thing. You simply don't do that. And also, I think, because we were so beleaguered, because we'd had people that were contributors to the software had been advocates and given tutorials, and all the kinds of things people do in a great software community, talk about how we were betraying them and how greedy we were and literally in the context of somebody talking about what... essentially, what ill-hearted people we were, was then somebody... this kid... this like 19-year old kid coming in underneath it and being like, by the way you should try my app. So it was just like... oh, come on. That's like lemon in the cut. That's just injury after insult, or insult after injury. So that was like... that was a terrible context... and I literally... I hadn't realized for, because I just had been busy, I didn't realize for like two days, oh WordPress is b2. It was one of those "aaaah"... I finally had stopped weeping at my desk, or whatever, and gone look, oh I know b2. It was this sort of like, oh, oh, that's okay. That's that PHP app. I've used it. And that was like a big thing. It was sort of this absurd... you know we'd already kind of got our dander up... but it was this absurd, like oh, [27:00] this is people we know. And I thought that was really telling. It was this very fraught place. And then for a while we just didn't worry about it. We went back to our work and did whatever. Because I just wasn't paying attention to it, and we were frankly doing clean up and damage control, we didn't realize how much that early WordPress community was really cemented together by... "we were betrayed by these Moveable Type people". And so because we were oblivious to it, we kept unintentionally antagonizing them. Just everything we did was offensive. Like stylistically... It's sort of like you go overseas and you don't realize you're being rude kind of thing. And in particular, I think Ben and Mena are pretty soft-spoken people, but I'm pretty brash. So I think there was this sort of like, we didn't know we were in a war. Until, maybe, about six months later, and then we had gotten... TypePad was up and running and doing pretty well, and we were starting to look at new versions of Moveable Type. And we're like, oh man, there's this whole thing happening over here where they're... oh, gosh, what was that site. There was a site called Blog Herald by a guy named Duncan Riley who later would go to work at Tech Crunch, and he had just straight up been making up things about the company. And it was like he was in Australia, so it was small stakes and it didn't matter, but he was on the other side of the world, so he would never run into us, so it didn't... but whatever. He would make up stories of whole cloth about like there's this internal fighting at the company because this is going on. As if we were like Microsoft or something. But it was like six of us in a room. So I just didn't notice it and then all of a sudden by the time I picked up it was like at that level, and I realized oh like you're, you know... and Mena being the CEO and this sort of... first the cute girl and then later the girl that everybody loved to hate, the mean girl, was this like, oh, she's just a totemic representation of everything evil. So then it was this just kind of cartoon caricature and that, probably immaturely on my part, I responded to by, well, let's provoke them. And so that was really where it came from. And actually, what was funny, was that around this time was one of the first times Matt visited San Francisco, and we both... I had always found him very similar. We're both PHP guys, we play the saxophone, we both like a lot of the same kind of music, and I was just like.. And I just liked a lot of what he wrote about, and thought he was interesting, and we liked a lot of the same things. He came and I don't remember if I picked him up at the airport, but certainly I drove him around most of his first day in San Francisco. So I picked him up. I brought him to Six Apart. We hung out. We talked about trackback or pingback, or something. [30:00] I mean, like, whatever was in vogue at the moment. We caught up with Tantek Çelik and we were talking about whatever standards and formats Tantek cared about. And got some food. And you know, just the things you do when you're introducing somebody to the area. I mean, I'd only in been in the Bay Area a couple of months. So I was like, look at me, I'm showing my expertise and then there's this thing. But it was totally sincere. I was very like, this is an interesting guy. Because I had been fans with the Blogger guys and we had sort of usurped them, I thought that, well, even if you usurp us, we're all on the same team. Immediately, as soon as he got in the car, I was like, oh, he thinks we hate him. There was like... I was like... uh oh. And so it was super awkward with me trying to like, you know, be the ambassador for this because I'm like taking him around. And by that time our team was like 10 people, so I'm like introducing him to people. And they're like all warily looking like, should I say hi? Like what should I do? Trying to follow the lead. It must have been equally awkward for Matt. And so I sort of cut that short and that was why we left and got some food or something. And I really was like, this thing is gonna matter more than the software. That was the biggest thing I came away with. We just talked about standards and formats and protocols and none of that matters. You know the term social media hadn't caught on yet, social software. None of that. There had been one event here in New York. Clay Shirky had done a Social Software Summit. And that was the first time I had heard the phrase "social software." And I still use it, which makes me sound like I'm from 800 years ago. But that idea didn't exist, and I didn't understand the implications of social, like analogies to the real world. And so the fact that software adoption would happen... and not to... WordPress is obviously good software, but that software... because of social factors, who was in the in-group and who was in the out-group, and who was nice, and who was not nice...#

Interviewer: Isn't that how you started out yourself, with Blogger?#

Dash: Yeah, you know. I just hadn't, like, hadn't registered. Funny thing was, it was this sort of... I believed it must not matter because we knew, like everybody used Microsoft Office back then, and nobody liked Microsoft. So how much could niceness matter? You were just stuck with software. That's, like, how it is. Obviously, Matt was very sincerely about serving, and I think frankly he had a huge advantage of being young. And so he didn't need to make any money, and he went to Cnet and was sort of doing that, and so it didn't really matter. You could just spend all your time of like, I'm going to serve these people really well. And meanwhile, so our investors, from day one, Joi Ito, Reid Hoffman, you go down the list, it's incredible people, right? So Reid was an investor before he'd founded LinkedIn. [33:00] So I meet this guy. And one of the times he'd come in and, like the guy holding his clipboard is Matt Kohler, who goes on to be number three at LinkedIn and number four at Facebook. So you're meeting all these incredible people. So for me I didn't have any contacts. I'd been in the Bay Area for a couple of months. I didn't know anybody. I didn't know anything about the history. I didn't know anything about venture capital or investing. None of that stuff. And so we're learning all that stuff and figuring out how to pay the bills and it's just like there's this other thing festering, we know there's something, and it' just sort of, you know, keeps going for a while. And that was how it stayed for my mind for many years. And then I think a little while before WordPress.com launched, I remember having this sort of come-to-Jesus meeting with the CEO and the senior folks, and I was like, look, the trend's against us. Like even though we had way more users, and way more attention, and the founders were on covers of magazines and all that stuff. And revenues, because WordPress didn't have any paying products at that point. And I was like, we have all this momentum, but I was like if I look at this stuff I would think I would use WordPress right now. And the funny thing about that was what I'd always... and at that point there still was WordPress, and I think WordPress MU had just started for multiuser, and the whole thing that had pissed people off about Moveable Type when we started charging was they couldn't have multiple blogs. And what they did in response is they moved to WordPress, where they could have multiple blogs. And the difference was whether the constraint was cost or code. And that was like this profound lesson. I was like actually a tiny fraction of these people could even have a remote chance of figuring out how to code this. And all of them have enough disposable income to be able to buy this feature. And even then, the free version of Moveable Type you could still have three blogs, so like that was still what we knew was the 98% use case. And we were trying to argue that on the facts. And I probably spent a year of my life thinking I'm going to point out the facts to somebody and somebody's going to say "I was factually incorrect on the Internet and I'd better change my mind." Again, it's that sort of naiveté or optimism or whatever. By '04-'05 I was like, oh you know, this isn't about this anymore. If I'm a normal person, I'm like... some of the economics have changed. One it's cheap to get... like PHP is included with every web host, it's easier to install, the mySQL databases were free where they had been expensive when we started making Moveable Type. So some of the, like, just technical underpinnings had changed. And the larger shift of like, you go to hosted services instead of running something on your own web server was fully underway. We were, I think, fully on-trend [36:00] with that with TypePad, but TypePad was all paid. To this day, I was talking to Say Media which owns it now, and they make millions and millions and millions of dollars off of TypePad. Today. And like, you know, TypePad is not the hottest platform going today. And it's because it's that kind of resilient business. And I think there was a narrow point where in 2004, Six Apart decided to be a large-scale lifestyle business, like a 37 Signals or whatever. And really doubled down on TypePad and fixed up the product and focused, and would probably have been... and probably introduce a free or freeish, free trial level that would have sort of captured that sort of blog. And instead, what happened was, kind of conventional expansion, another round of funding, acquiring LiveJournal, and taking this other turn. And so it became this like we're going to have a portfolio of blogging companies... blogging services... and all this different kinds of blogging. A lot of really good ideas and a lot of great open technologies created, but no focus. And I think because of resource constraints, and because of that sort of Matt being young and not being an entrepreneur and not having VCs or funders, he's just like I just want to make this app. So I think it kept WordPress so much more focused on the community. And the sort of... I think it's actually understated how much it mattered that it was PHP versus Perl. I think there's fashion in all kinds of technology. People don't want to admit that. But even right now, I look at what hackers work on for blogging tools and if it's Jekyll or other things like that, and they call them static site generators, and I'm like you know this was the biggest albatross around our neck for Moveable Type ten years ago, eight, nine years ago. Was you know, everybody using WordPress and Matt and everybody at Automattic constantly saying we're dynamic, and it's fast, and you don't have to rebuild. And we were kind of like, you know, actually, there's some merits to this. Like this scales like crazy and this is really nice. And I literally saw a couple months ago, this write up... and you have this exalted tech team that worked for the Obama campaign and they get all the... we won the election with technology, which is not really true, but this is what the press likes to say. And like their big story they told was we made a static site generator that held up under extremely high load for election day. And it was, this like, yeah you're building pages with templates. Like this is the thing we got our ass kicked on ten years ago and you guys are proud of it. And it was really funny to me because it was such a pure... even today as much as WordPress has advanced, like caching plugins are still the bane of many WordPress users existence. Because they're like three of them [39:00] and like the one doesn't work with your other plugin and whatever the issue, it was so funny to me, it was like, oh, this is like hemlines, they go up, they go down. Static will be in favor in odd years every ten years, or whatever. The first time around, we didn't get any of that. We didn't understand any of that.#

Interviewer: A lot of the, in fact all of the original developers I spoke to have said it was because they wanted to work in PHP and not in Perl. So many people have said that.#

Dash: I'm the same. I still to this day don't code, I've never coded in Perl. I've made a living coding in PHP for years, until I joined Six Apart and starting writing on Moveable Type. And I've never written a line of Perl in my life. I think that's a huge part of it. And it's funny because, the sort of... the same thing of the conventional wisdom of decisions being made logically, Perl was much more advanced in terms of shared libraries and clean code and the architecture of the app. You know WordPress inherited a lot of that b2... I hesitate to say design, but it wasn't design, but it wasn't design, and then sort of retroactively has had to work around that. If you're creating something from scratch you don't end up with the loop. That's where you arrive at when you take a code base that is there. Every code base is like that. It's not a criticism of WordPress, but it was sort of this like, because we looked at this logically, like who wouldn't prefer well-written in this language to poorly-written in this more popular language. Well, the real world. I think that was absolutely a factor. But those things... it's funny because, I think it was a factor for developers and a lot of us early on were developers, but that wasn't for why a great blogger started or switched. Because like we had so many of the early bloggers. So if you were a mommy-blogger and you looked up to Dooce or you were a tech blog and you wanted to be Daring Fireball or you wanted to read politics at Huff Post or gossip at Gawker... like across the board. It didn't matter what it was. I remember doing an internal presentation for new hires at Six Apart. I'd be like, look, you wanna look back at when the Howard Dean blog was the pinnacle of web politics, that was us. And Fred Wilson being the definitive VC blog and that was on Type Pad. And so we could go down this list and it was like... none of it had anything to do with technology. You actually could have done 80% of those sites on Blogger. It was all about who's the thing to use right now. And we actually, we did a lot of probably foolish things to try and get, oh well, we have a PHP way of working at Moveable Type, you know those kind of things. That was all... the sort of... [42:00] short term thinking. It was not seeing the forest for the trees, I think in a lot of ways. And inexperience again, being part of it. And also the lack of focus. And I think that was really one of those things that WordPress did brilliantly well, whether by design or just by circumstance. Matt could only do one thing at a time. And everybody being volunteers and core contributors, you can't give them orders. So they have to be working on what they want. One of the things I focused on most towards my, sort of, later time at Six Apart was I worked a lot on our enterprise business and our business case... TypePad had a business class, and that was a huge business. I mean the first quarter out of the gate we made a million dollars selling that stuff and I found out was a lot of money for blogging software. And it went up from there. And it was a really big business. And I think still, for the companies that own the pieces of what's left of Moveable Type and TypePad, still pretty big businesses. To some degree... and by that time it was sort of... at least I found it very fun to go back and forth with Matt. I think he was more exasperated by it. I truly thought it was playful. Like I literally only eight years later, having lunch with Matt, realized that it had been much more, sincerely frustrating to him. The thing I saw was like, if we can keep everybody in the WordPress community focused on individual bloggers that I know you can never make any money from, because they get pissed if you ask them for money, then we can take this sort of high ground here where we're taking money away from Vignette and SharePoint for multimillion dollar content management systems. And that we did a great job of. Like that was a lot of fun. And I think also, like, fair play to Matt, he was right to not find that interesting. It's not an interesting business. It's a drudgery business. But that's what they pay you for. So I think that was a really... That when things started to change. It was like, okay, here's a space that's wide open and to me interesting, I know not interesting to most people, but it also was a de facto concession to the sort of individual blogger market. The shame of that is, WordPress became so dominant, and even is today, even despite the rise of the Tumblrs and whatever of the world, that there isn't another tool that you can install yourself and hack on on your own site that has any real usage. There's these one-off things developers do. But the thing I lament about having to look back, it's like at the time you could switch back and forth. People would switch apps, you know, for a year, and they would be like I got tired of this, so I went back to that, or whatever. [45:00] And you would try and learn new things. And I think that's the sort of thing that like the ecosystem that I miss most. I don't lament, WordPress earned its victory, I think what I lament is that there's no meaningful, like if you switch from WordPress to Tumblr, or vice versa, you have a different thing. And you can't tweak the same variables. You can make the same changes and try the same kind of innovations, and I think that sort of thing was the, sort of, great loss of that era. And I think... one of the things that is really interesting to me, is... Matt had been very positive about Vox, which was like the last platform Six Apart launched, this was at a time when I think there was at least good will between the two companies. I couldn't tell if he was being sincere. Because I didn't work on Vox, I worked at the company but I didn't work on it. So I really didn't have much familiarity or interest in it. And the concepts around like people who would want to share things privately with their friends and family and bring in YouTube videos and Flickr photos and all that stuff. That I sort of took for granted, like of course we want to do that. I almost felt, and I think the market proved this, it was much too complicated and sort of forced too much to users, but that basic model was not at all different than what Tumblr did. It was this single stream, your friends page was there, you could be private or public, you were primarily reblogging other things or pasting in other embedded videos... like all that stuff was straight line from I think what Vox did in the early days, and actually this is something inadvertently I pissed off Marco Arment saying this, but like I think this was in the air. I think what p2 did on WordPress, what we did on Vox at Six Apart, what a number of other services were doing, like got congealed best into Tumblr, but theses were ideas that were percolating. It's funny, because I didn't realize it, but Marco Arment is not a fan of mine, and he's like well you know, you're always such a jerk to Matt too. I think Matt and I get on pretty well these days. Because the fundamentals were always the same in terms of interest. There's a very sincere interest in the medium, and in the tools, and in the way you approach them, and the mindset. I mean I think the company I'm building now, I think about the app we're doing, it honestly resembles the early days of Automattic more than pretty much anything else. It was just because like oh yeah, this is the sort of... if you have the chance, and I've the luxury to do it this way, it's a pretty good way to do it. I mean I'm twice the age that Matt was when he started doing WordPress, and that's sort of like, well, I don't care that I arrived at it late.#

Interviewer: Yeah, it sounds like a fun thing to be doing though, starting out a company as Automattic did it.#

Dash: Yeah, we have a real, sincere, engaged, open source community. [48:00] We're building a product we care about. It's PHP. I think there are so many things that are similar in that regard. And for me too, this is the first time in ten years since we started Six Apart, that I'm sort of hands on in building a product and getting it launched off the ground from day one. At the same time, there are things that I think if I were doing... if I had been doing Automattic back when it was starting that I would have done differently I think of like... what's happening with Jetpack is fascinating in terms of connecting the sort of decentralized installs to the powerful infrastructure of the center and that's a lot of what we've been baking into the app we're building, but like that was what we tried to do with TypeKey and the world wouldn't let us because the market wasn't ready. So there's a too early / too late balance there. Like we were sort of too early, and I wouldn't say it's too late for Jetpack, but just it's much harder to do now... please would you install this plugin as opposed to if you had just baked it in. And then of course the question about the fundamental architecture. You have an app that runs on other people's servers, not your own, in addition to... like the dot com, dot org division, and that sort of... there's very few apps in that vein any more. Even Drupal has largely moved to a couple hosting services and I think that's sort of similar... I mean I wouldn't be surprised if that happens with ThinkUp if we happen to succeed. But that sort of model of there being things interesting out there on the web... I pushed several times for Matt and David Carp to get together on having follow between Tumblr and WordPress, obviously that won't ever happen now. I said if you could do reblogging and following between these two networks, this would change the web. And I think that idea, we're still going to innovate around what ways to work together, that's probably what I miss most. Even when there was this sort of... you know, the battles about why my app is better or you shouldn't use my app or you're a jerk or whatever, at the same time, we all got in a room together to work on stuff like No Follow or the various anti-spam things, or things like that. And that's sort of like, there was at least a sense of civic obligation. That is, obviously, in an era when Twitter and Facebook shut off each other's friends lists on their apps, like that's gone. And so that I sort of lament, and that's the thing that I sort of still today most look to WordPress for and really would advocate for and want to see more of. I think it's interesting Automattic's buying up... like I noticed stuff like the SimpleNote folks.#

Interviewer: Yup. Simperium.#

Dash: Yeah. And like that was like. I sent Matt a note. That was like sort of brilliant to do on the 4th of January [51:00] when nobody's paying any attention because that's a huge deal. And sort of flew under the radar. Like I think any other company... and also that people don't realize sort of how big and valuable Automattic is now. That was really interesting to me. Those things are exciting and it also makes me wish for, like okay, since it's the inclination of Automattic in the way that it's been started, is there a way to make that an open spec, an open format that we can connect to, or at least an API that we can build around. Those all seem very possible. That's the thing I'm most excited about. I feel like the can I type a post in a box and have it go up on the Internet part is pretty solved.#

Interviewer: I think so.#

Dash: You know? I'm like I think like we're good. And actually I said this at the Q&A session a couple of months ago, and I think somebody who was a veteran of the blogging wars took it the wrong way, but I said WordPress is done. And I didn't mean like people don't want it. I meant like it's finished. Like the ability to do the things you want to do is complete. They can be improved upon, simplified, whatever, but that there isn't some other feature missing. And that sort of... that's where I'm like okay, what were the unchecked boxes from five, ten, fifteen years ago that are incomplete. That's what I'm really interested in. And I think there are still large areas... and what would it look like in a era of Facebook and Twitter, to bring back trackback and pingback and say what does it look like in modern context to show links between sites. To drive conversation between separate individual sites that don't have a pre-established relationship with one another. What if that happened? Basic things like that, that we sort of lost along the way, I'm very, very excited about and interested in. At our office at ThinkUp, we share space with Medium and Branch, both being obvious companies. With Medium in particular, another view on blogging and sort of in that case Evan trying to work out stuff he's felt unresolved about for fifteen years. And I think that that sense of like... there are some of us that are going to be kept awake at night and plagued by the problems of this kind of communication for the rest of our lives. Whether we choose to or not.#

Interviewer: I'm glad some people are.#

Dash: I hope so. I hope so. I mean I think that's the thing that distinguishes whether, to some degree for me what happened... who I respect in the space... because like the sort of petty grievances of early competition aside, I've been very happy to see Evan and Matt and others be wealthy and have nice homes and all those things and I'm sort of like... that's all great, but we still have to fix this software. I said this in a blog post not that long ago, maybe last year or so, [54:00] I had fun with the sort of back and forth, Tom and Jerry thing, with Matt, I think the thing that I would have done differently is like... I think it's fine to have a competition that gets people heated or whatever. What I lament is it focused the communities on us and our personalities and our respective companies and the winner of, you know, WordPress versus Moveable Type or whatever was not WordPress, but Facebook.#

Interviewer: Yeah. I read that post actually.#

Dash: And I didn't get that for years.#

Interviewer: I guess one of the things I've found interesting doing all of this research is, I mean the web's kind of old, but also kind of young. And all of the kind of the things that happened between you and Matt and Moveable Type and WordPress is pretty early on in the web. It was all affect...#

Dash: It's ancient history. Nobody even knows about it. It's funny. It feels fairly recent but like... I mean if I go into a meeting and I tell people I was at the company that made Moveable Type and people don't know what it is. They don't know that it ever existed. On the one hand, I think well I spent six years of my life, or seven years of my life, working on that. But it doesn't offend me or hurt me at all, but it's one of those, wow that's how short our attention span is. Well, people don't even remember Friendster.#

Interviewer: Yeah, I know. It's barely a memory for me.#

Dash: Yeah, I don't expect everybody to remember everything from ten years ago that some minor thing on the Internet, but I do think there's something interesting about how short our attention spans are.#

Interviewer: A lot of people in WordPress really remember the Moveable Type licensing change. And for most... a lot of people...#

Dash: It was actually seminal for that community than it was for us. Because most of our users came after that, so Moveable Type had always cost money. But like WordPress users had to sort of keep alive the schism moment, the reformation. And I don't mean that in a bad way.#

Interviewer: No, no, I think it's good. I think it's a great way to describe it.#

Dash: It's much more important to say well, they did this terrible thing to betray their community, and we righted it. I've always found that really interesting. It's much more like... I've spoken at a WordCamp once or twice and like, it's much more likely that people remember it there, than at any... and I was at... I can't even count how many Moveable Type events I was at - and it never came up.#

Interviewer: And do you think it was a money issue or more to do with actually the fact that the license was changed.#

Dash: You know, I don't think actually the dollar... [57:00] because like we... by the end the license was totally reasonable, it was pretty cheap and it was only a tiny percentage of people who would ever have to pay for it. I think it was the reckoning of like, this medium is going to be a commercial medium. I think actually in the same way of like when Matt had put the text link ads on WordPress.org and people freaked out... and it's funny because we very studiously didn't make a big deal out of it on the Six Apart side. One, because we didn't know if we going to add ads at some point. You know? Because we're not gonna like... besides not wanting to be jerks... like, hey, ads are part of the game. We wouldn't hide them, but that's like whatever, that actually a minor concern at a certain point. I remember a year or two ago, somebody saying the old GreyMatter site was still running and had like all these like sketchy ads on it, on the home page. What's worse is when you have the ads visible and nobody cares. And it was interesting to us because like we saw that it was actually the same sort of reflex, even within the WordPress community most of whom at that point had joined after we had changed our licensing, still being this sort of anti-commercial... the second wave of like, there should be no way to make money on this medium. We're like, well, we know you don't believe that... I remember I was having conversations with like, we know they're all using Yahoo!... they've got ads in their life. And Firefox hadn't caught on yet, so there wasn't like ad blockers. And that was really one of those things of like... the real reaction was you're forcing me to reckon with change in this medium that means something to me. And if you were there that early, it wasn't... the analogy I keep coming back to when I tell people about it that were never there, don't know anything about it, is it was much more akin to a bunch of bands in a town about to breakout with a certain sound or style than it was a bunch of competing software companies. I live in the East Village in New York City and this is where you know, where a lot of sort of New York punk and rap had its start. And you know the idea of Madonna and the Beastie Boys playing in the same club seems crazy now, but they were trading ideas and sharing production ideas and contributing to each other's records and all these things and that sort of sense of like okay you're part of a bigger scene and it has something to do with something that's larger than yourself. And in the same way, the minute a first rap artist gets signed to a record label, it's like well what are you doing? How dare you sort of corrupt our pure artistic scene? And I think in many regards it was that, because the only other commercial thing that had ever happened, [60:00] was Blogger doing its server fund before that. And that was like, well we gotta keep the lights on and would you pretty please... And it's funny because nowadays again, you know, you would be crowdfunding and we're going to raise this much. But to think of Evan Williams, hat in hand, asking pretty please will you give me twenty thousand dollars seems absurd. And if I remember right, he got the idea from Michael Sippey who's head of product at Twitter now. And so that sort cyclicality is really striking to me. Because I think there's a sort of... there's a latent awareness of those of us that have been there for fifteen years or a dozen years that remember that. And the modern web... like Zuckerberg doesn't know any of that. I don't fault him, whatever. Like he's got his priorities and he's busy doing his thing, but I think he would benefit from knowing it. Because I think it's one of the reasons why Facebook is so, sort of, socially aggressive. Like I don't care if Facebook has ads, I care if they change the interaction that I have with... or the relationship I have with the community or with my friends. And I think we sort of, with Moveable Type, threatened that, or we made it feel as if that was threatened to people. You're changing my social dynamic. And that... I had spoken to Marissa Meyer a bit before and around the Tumblr deal, and the thing I said to her, and I take no credit for her choosing to go with that language in her post, but the thing I said to her was you got to tell them you're not going to screw it up. And literally that was the message I said to her for half a dozen times and I think everybody must have too because that's what she put in the... that's like the subheader on her press release. And I think it's probably mostly attributed to David, knowing that's what matters most. But that's lessons learned. Because Carp does know the history. Had seen all of that. And had seen how, had seen Moveable Type come and go. I think that's sort of what can go wrong. I think it's as interesting a story to say Automattic's a billion dollar company, Tumblr's a billion dollar company and there was a third player that at one point was as credible as either of those that is a zero billion dollar company. And the reasons were primarily social.#

Interviewer: Do you think the open source aspect, the GPL, the fact that WordPress was an open source community, actually made a difference?#

Dash: You know, it's funny. I know it's fundamental to Matt and to the community. But the real world doesn't care that much. And I say that as the CEO of a company whose product is GPLed. Open matters. Open enough matters. And certainly when [63:00] Mark Pilgrim wrote about Freedom Zero it hurt Moveable Type a lot and got WordPress a lot of users. And my advice the day we changed the license was that we should have open sourced it, although I think I favored an MIT license. I don't even know why I care about the distinction now. For some reason it mattered at the time. And I think just feeling a sense of trust. Because I look at Tumblr, right, and there's nothing open about it, in any sense. But people trust the platform. And I think that's, one, a generation of people that grew up before, without even having an interaction with open. Like open doesn't really mean anything to them. And two, David's been as good a steward of his community as Matt has been of his. And I think there's sort of... there's an interesting thing that I think Apple has taught the whole world, of like, everybody thought nothing could be more closed than Microsoft until Apple won. And so there's a sense of design trumps open.#

Interviewer: Yes, that's very true.#

Dash: To some degree... there's nothing in Tumblr's purvey that shouldn't have been, you know, WordPress' to claim. And that entire opportunity was carved out on design trumping open.#

Interviewer: It's true. I was at an open source conference a couple of weeks ago and all of the WordPress people had Macs, and all the GNOME and Ubuntu people had like Lenovos and were running...#

Dash: ThinkPads and yeah...#

Interviewer: I was feeling guilty.#

Dash: Well, you know. I'm not religious about it. Having been on every side of it... One thing that was really interesting to me is we... like Moveable Type was always technically open source, because open source didn't imply free software license, and I was always really careful that we never said that until we were GPLed, later on we GPLed it. But until we were we never did, because I was like, look, people are going to string us up because they don't feel like we're open. We can't get away with saying it, even if it's technically in some weird way true. And that was actually part of what I tried to push to the Vox team in the little interactions I had with them. I think if you're prettier, you'll win. I think that sort of... That's something I take a lot of lessons in. Like right now, where I'm literally working on the design on ThinkUp today, where I'm like... and actually like GPL and open data and all that stuff, that will matter to our developer community forever I hope, but we're going to get users because this thing is going to be beautiful. [66:00] And if it's not, we're not going to get users. And even to some degree... like I assume our sort of .com to .org, hosted versus not is probably going to be 90% on our infrastructure. I think in contrast to WordPress where there's tons of stand-alone installs. And I think the key is like we are maintaining this out of, to some degree out of principle, but also... one of the things I want to demonstrate is these things don't imply unusable or ugly. We sort of haven't seen that. I mean I think WordPress is in a different category because it's a CMS and your admins see the app but everybody sees the output. And ads force a lot of sites to be ugly. And so one of the things I think about a lot is like can you build a consumer grade experience that's easy to sign up for and a joy to use, that is also meaningfully open and I don't know that anybody, maybe arguably Firefox, but even that's sort of... like Chrome is a better experience than Firefox.#

Interviewer: Yes, it is.#

Dash: And Chrome is like technically, license-wise, open, but not in any meaningful sense. And actually, same with Android. Android has gotten pretty pretty, but it's not, you know... I guess you can install your own apps sometimes, but mostly it's not open in any meaningful sense.#

Interviewer: So if you could go back in time, would you change what you did with the licensing?#

Dash: I would explain it better.#

Interviewer: Yeah?#

Dash: I think that's about it. I mean I think I would do... It's funny because I advise all these startups and I'm on boards now, it's like simple. Tell them what's coming, ask them, for their feedback, ask them if the proposed solution meets their expectations for the feedback, and then iterate. And we only skipped like all but one of those steps. And it sounds very obvious now, but I don't think it was conventional wisdom. Because you didn't expect a fast feedback loop. And we did surveys... we literally had... we were going through Craigslist and getting random people, we were like phoning people to ask about... like there wasn't... like you could email them, but people didn't even check their email every day. This was ten years ago. So you couldn't... like there was no SurveyMonkey, there was no PollDaddy, you couldn't do a, you know, if your blogging app cost this much how would you react. Like you couldn't do that. And get results back in a day and be like we've got a pretty good sense. Let alone tweet hey ***[audio fades] so that sort of immediacy not being there was a big part of the feedback loop is this multi-month process where you go underwater. Given that was the case, I think the thing that could have been done better is to say here's our problem. We need to make this much money to support this kind of app. [69:00] And these are the ways we can do it, and we don't want to do ads, how should we work on this together. And I think we would have arrived at the exact same solution. I really do. I mean the numbers, they just add up. But I think the community would have had the buy in and been able to see the rationale as opposed to thinking some dark, Machiavellian force behind the scenes is trying to extort them.#

Interviewer: So did you have a big community.#

Dash: Yeah, yeah. Oh very much so. And there were... and for many years they still were. It wasn't like the light switch pulled off and we ***[not sure what was said] I think the majority of them actually stayed with us. It was a very small vocal minority that shifted on sort of day of, but the energy got sapped out over time. And WordPress grew very quickly. As the medium grew. And that just made the protection[not sure what was said] shift. Amplified the actual shift. But there was always a big community. There still are. I got some, I get... I mean because I was at the company so long, I get people emailing me hey I need somebody to build me a Moveable Type site... which I assume I'll get until I'm dead. There's still those companies, as they've been consultants, doing that for ten years and they go out and do that. So that's still out there. Obviously, it's nothing like the WordPress community is, but it's still a bunch of viable businesses. To my mind, honestly, like I said I think the thing I would have understood and it's funny because it's so much of my work now, is like how people feel about these things and what it means to be part of a community and what the social factors are and whether you're accommodating the way people feel about their engagement with technology. These are how they make their decisions. And we could pretend we're as rational as we want or that we do things by the numbers or any other sort of pretense, but I think the lesson from blogging software, from the rise of social media and social networks, is that we're social animals and there are so many people that claim they are annoyed by Facebook, that are members of it. And it proves what a draw... tons of people that believe in open source that use closed platforms. We're humans. We're emotional animals. And we care about connecting with one another and having a pleasant experience and seeing things that are beautiful. The questions is if we can bring those in alignment with our values around how we think technology should be created and what open means and how we share data. Those are the things I think are other really big challenges. Like I'm very bullish and optimistic about WordPress being part of that going forward, but I'm sort of like also excited to say that maybe we can start anew, with new kinds of apps and do this again.#

Interviewer: I'm excited to see what happens. [72:00] I love medium.#

Dash: It's great. It's a great platform and I sort of look at it like, well you know, the reflexive, defensive part of those of us that have ever built blogging tools is to want to say well we could do this before. I can do that. Pshaw. I could take an afternoon in WordPress and build this. And I think the thing is to say what's different here. And one of the things I'm most drawn to is... the discovery being much more like YouTube. Like I never get lost in a bunch of blog posts. I know there's a reader on WordPress.com but it's not a primary experience for most people. And it would be hard to actually put the genie back in the bottle and try to make it be. I think that would be a very radical thing. Let alone getting rid of templates, design and all the other things that go away. And it's funny because with Vox we did a lot of that. You can't edit your templates, your HTML. And we picked a handful of choices you could have. And people freaked out. Now nobody even looks twice at the fact that there essentially aren't templates and designs on medium. I think that sort of evolution of you can change your avatar, it's the only thing left, there's good and bad to that. There's good and bad to the open endedness. That's why I'm looking at maybe there's a way to flex back. There's a way to sort of kind of have the best of both worlds. I think there's cycles to these things. I think we'll discover them again.#

Interviewer: Yeah, I like that there's something with a focus purely on writing and that's it. That's all the user have is the writing aspect. And I think that's great.#

Dash: And they've set incredible standards around expectations. You wouldn't feel right to go in there and write something with spelling errors that was not well thought out. What a tribute that is. That's such a rare thing. I've seen people say, oh gosh it's just too serious. I'm like my god, I've never seen a web community [inaudible] like their writing is too serious. I think that's quite a tribute. I think that's... those are the things I'm excited about. Is there ways to do that new.#

Interviewer: So why do you think WordPress was so successful?#

Dash: At a fundamental level, blogging is the sort of native idiom of the web. As the sitcom is to television, as the sort of two and a half page article is to magazines, this is the form that suits the medium. More broadly I can make the case it's actually, it's not even intrinsic to the internet, it just was only possible on the web. [75:00] I think TV might run better that way too, but it's harder to do in a reverse chronological. At the fundamental level, people need this thing and so by default they need a tool to do it. And then the second part is the sort of... well, do you just want to get it out there or do you want to control how its out there. I think frankly to just get it out there I think Tumblr as a medium is a better choice, for me. To control it, then I think WordPress is the better choice. And the question is, is control it's on your servers, is control you need to put ads around it, is control you have some particular design in mind, and all the other things. There's a billion CMSes out there. I used to say, when I was in the job of selling online content management system, every content management system sucks, the question is just which regards does it suck. I still pretty much believe that. The fun thing for me about not being in the... an arms dealer any more is people ask my opinion and I'm like they're all terrible, I don't care what you choose. It's a little exaggerated, but not much. I think WordPress has done a very good job of sort of admirably avoiding becoming the be-all, end-all content management system. All the people have hacked it into everything that can be imagined, but by default it's not that terrible. When we added custom fields to Moveable Type, I was okay we're no longer a content management system, this is everything. This is just a database. And I think that might be how I feel about the category overall. Where it ceases to be... we stop making choices as software developers when we add the everything field. Miscellaneous. I think WordPress has succeeded because it's structured enough that you can get started, you know what to do, there's great templates out of the box, you have some control, this is the choice for people that want to control what they're doing as opposed to just type in a box. I think the WordPress has succeed despite is... is sort of despite the fact that it has the custom fields. Because I think it's the greatest entropic force to pull apart a content management system. Because at that point, oh well now we need types, and now we need to figure out what we're doing, and Bob's your uncle, and you're done. So I think that sort of... a good, in my heart, a good blogging tool is different than a great content management system. [78:00] It's funny to see the brief blip of excitement around Ghost, because these things follow cycles. Or Habari back in the day. The great sort of software is never made in reaction to another piece of software. I looked at Ghost and I was like, this looks to me like a very nice version of a pissed off core developer who realized that forking isn't meaningful. I don't know any of the people involved, so I might be right, I might be wrong, but that's my like... I've been doing this a long time, that's what that looks like. And like, screw you, I'm taking my marbles and going home, just doesn't usually yield very good software. Sometimes it does, but usually it doesn't. Good software is like we made good choices, have great defaults. We're not burdening you with choices and we've got that exact right balance between open-ended in what you do, and this is very defined in what it does by default. I think WordPress has struck a really good balance on that. I mean I think it's a total tribute to, really fundamentally, to Matt, of getting the right balance of that. The first ten years are the easiest. The next ten, when it's like the web changes in kind, I'm sort of... one of my biggest questions I'm reckoning with and basically trying to understand this basically going forward, I think we might have been wrong in the fact that we publish web pages. That's a thing to think about. We make a lot of assumptions around the fact that were going to output pages and that Google is going to index pages and all those other things. And if SEO dies, and web pages die, and people just want to consume stuff in streams, how does the creation tool for a blog change and if it requires significant changes around defaults, what do you do with millions and millions and millions of people running an app that's gotta stay the way it is, right? The two options are you start anew, you start from scratch, you have these sort of two parallel things that are different, or you have a subset. These are like... whether it's Windows 8 or the various efforts Blackberry is putting up or Apple going from classic to OS X, those sort of like, we've reached an inflection point now where we're going to be a different thing. Those are the hardest problems in technology. So that what I'm sort of like... I'm very excited and happy for WordPress' success. I don't know what two years from now looks like.#

Interviewer: It's the big challenge for us...#

Dash: I imagine so.#

Interviewer: Touch devices and all of those things are just... [81:00] I don't know if you've ever tried to use WordPress from a iPad... it's horrible.#

Dash: Yeah. And you guys just picked up one of the client apps, I know that. The thing I think about a lot is... there's nobody who's 15 years old who would start with like what we have as CMSes today and build a site. Like that's just insane. And if I look at what I do on my phone and how far out of sync everything... my blog is still on Moveable Type, not even out of any loyalty, but just laziness. It's funny because I looked at WordPress and I looked at caching plugins because I actually get some traffic sometimes and then I was like - too hard. It's just too hard. And it's funny for me that it's not even about some like dogmatic loyalty thing, I'm just like... I can't figure this out.#

Interviewer: I'm sure Matt would migrate you and set it all up.#

Dash: Oh, I'm sure he would. And that would be very kind. I wouldn't give him the satisfaction, even after all these years.#

Interviewer: Well, no...#

Dash: Well, for me too. I have it running on my server still, and it's a box I have root access on for no good reason. And I'm very particular. Like I have certain... there's blog posts I wrote eight years ago that have non-standard URLs that I want to preserve. And all this crazy stuff. And also the sort of... I think WordPress was the sort of winner from the set of problems we defined ten or fifteen years ago. And I'm happy for that. But I feel like I want to solve, like if I'm going to change, I want it like to think of what's the problem in five years. And I looked around a couple of months ago, I looked at all the stuff, and it was like, these are terrible. Some of it is I'm spoiled now, so I want like fit and finish and design and polish and whatever. But like none of them are as good as even Blogger was in '99. And there's sort of nobody even recognizing this is an audience, and I'm like, you know, it might be there's only a hundred thousand of us left that have this kind of blog. But a lot of them are my friends. Jason Kottke and John Gruber and Andy Baio and whoever you want to point at, those are my people. That's who I go to dinner with. These are my friends. And for us, there's a sort of... well, for one, if we were going to switch to WordPress we would have and that's sort of six of one half a dozen of another, that doesn't really matter. But there's like, well, what's the next thing? What's different? And actually to some degree it feels to me like I can switch between iPhone and Android, and if all I'm doing is using Twitter and Vine and email on them, who cares? Versus something like, this I couldn't do before. So I think that's the thing I'm... [84:00]] Like WordPress has succeeded because it's very good software that's made really good choices about the way people use it and been adaptable to many scenarios. WordPress has also succeeded because we haven't been able to figure out what the next phase for blogging is. And maybe it evolves to be that dominant in the next wave, I don't know. But we don't know what that wave is.#

Interviewer: I think your comments about Facebook are still pertinent there. Facebook and Twitter are the next things, so actually WordPress is one thing back.#

Dash: Everything people do on Facebook and Twitter I know we all envisioned as part of blogging. The basics of discovery, even a hashtag on Twitter was a technorati tag on blogging. But not that there's nothing new under the sun. These things are very cyclical and everything that we wanted to be able to do, sort of the way you post on Facebook that was very inspired by Tumblr, like we called it structured blogging, and there were plugins for it for WordPress in like version 1.2. There's no feature that's ever come out of Facebook or Twitter or whatever, where it's been well, we didn't see that coming. That's shocking. Like sign in, sure. Like connect, yes. Comment, yes. These are all just solving the exact same problems over... and they've done it better, obviously, and at unimaginable scale, which I don't diminish. But in terms of core capabilities, I'm like god we still have so much, so much left to do.#

Interviewer: I'm excited to see what happens.#

Dash: Me too. Thanks so much... I really appreciate that you... I never talk about this stuff. Like I'm busy, I'm running a company, I'm doing all this stuff. I never talk about this stuff. And also the people that I'm close to were all there, so there's like... they don't... they know better than I do, so I can't tell them. It's really interesting. Actually I'm going to be seeing Mena Trott pretty soon. I don't know if Matt knows, but, obviously your familiar with this time and that era. Her and Ben had split up some time ago. She's quietly getting remarried.#

Interviewer: Oh, okay.#

Dash: I was just talking to her about this sense of like I'm doing a new company, and she's actually been helping out with some new ideas of what I'm doing. It's exactly ten years since TypePad was launched in '03. So there's this sense of like, you know we may not be young, but we can still do something interesting.#

Interviewer: Wow. You're still only like young. Your only old in the way the Internet is old. Which is not really old.#

Dash: [87:00] Oh, yeah, yeah, yeah, you know. I'm hoping I've got another fifty years left. But I have a good solid fifty years of work left to do. So I'd better get the fifty year. I just think it's really interesting... and also, Matt's always been... it's funny because Matt, Matt's older than Zuckerberg, right?#

Interviewer: A little, yeah.#

Dash: So it's like, well, that's it. You're not the wonder kid any more. There's sort of... there's always going to be somebody younger. Even Karp, when I met Karp he was like nineteen. And I was like, another one of these bastards just hanging out. And even he's looking like a grown up now.#

Interviewer: Yeah, I think there's going to be more kids that appear.#

Dash: Yeah, I'm excited about it. That's always the fun part when somebody comes out and you're like what the heck is that? But that's really what I want. I'm really excited to see somebody come out with something where I'm like I don't understand this and this is unrecognizable but this must be the next step.#

Interviewer: It's funny what you said earlier about the first time you saw like Blogger or kind of a tool for getting stuff on the web. I remember my first experience of a CMS and it was like, people can actually do this? This is amazing!#

Dash: It felt like science fiction. I had made pages by hand. The tagline on Blogger was push-button publishing for the masses. And that was like... I can still see it clear as day in that Blogger orange and just thinking this is the future.#

Interviewer: Thank you for speaking to me. If I can make it to New York there's a few people I'd like to speak to, but maybe we can...#

Dash: Sure. I'm happy to do any introduction too if there's folks you want to connect to that you're not...#

Interviewer: I'd love to speak to Mena Trott actually.#

Dash: Yeah, she's out in Oakland I don't know where you're based...#

Interviewer: I'm based near London, but I'm going to San Francisco for ten days at the end of...#

Dash: Let me know when you're there I'll drop her a line. I'm sure... honestly, literally have no idea what her interest might be. She might be super interested or she might be not at all interested, but I'll be happy to introduce you.#

Interviewer: Yeah, that's fine. Getting your perspective is really interesting to me because for the WordPress community that was a big moment, but for you guys less so and I just love that.#

Dash: Well that thing... like I said schisms are useful in defining what a community is but our community was sort of already defined and so it was more meaningful to the WordPress community and I think... it was funny because... sort of the pretext is that you have to see that decision as this negative and so I became the person that made this negative happen. But I was also the person that pretty much always that was bringing in revenue to keep the company going for our side. And thus the ecosystem going. So it was this sort of like... [90:00] I wasn't offended by it, but it was a really clear... it was actually the first I'd learned about that sort of equivalent of being a public figure. I mean it's not being a public figure, but that sort of... people's perceptions of you are decided by what camp they're in not by what you do. In the manner of a politician. If you support Obama, going on a golf trip is fine, he didn't go on as many trips as Bush, and if you hate him he's like shirking off his responsibilities and I think that's sort of like... now that I'm a little more grown it's just a golf trip. I can't imagine in today's world a choice by a CMS vendor around pricing or licensing that would get anything more than a glancing mention on TechCrunch.#

Interviewer: Everything got mentioned on TechCrunch. You and Matt, like reading the *** cracks me up.#

Dash: Oh god. That stuff doesn't age very well. I come off as even more of a jerk than I am.#

Interviewer: No one comes off well.#

Dash: It was fun though. Part of it was the sort of fun you have when you have communities, you want to give them something to respond to.#

Interviewer: So it was like pantomime.#

Dash: They encourage your worst behaviors really.#

Interviewer: We picked up some background noise. I'll email you my dates that I'm going to be in San Francisco and once I actually get round to working on this stuff I will let you know. We're actually working on the book on Github.#

Dash: Oh that's really cool.#

Interviewer: So people can follow the progress of it. It's in very early draft at the minute, so it's kind of embarrassing to see your writing on there before an editor's got to it.#

Dash: That's how it goes. And what's your timeframe? What are you think you're going to take and put it out?#

Interviewer: I'll think I'll have it complete by March next year.#

Dash: Oh, that's great.#

Interviewer: That's my plan. I've got the first sort of three chapters done already, so...#

Dash: Wow. Well I can't wait to see it. That's very exciting.#

Interviewer: I'll definitely let you know when it's complete.#

Dash: Please do. And do be in touch if I can give you an introduction or whatever, or even answer any questions if I'm unclear about things.#

Interviewer: That would be fantastic. Thank you so much.#

Dash: Thank you.#

Interviewer: It was lovely to speak to you. Bye.#

Dash: Bye.#