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They need a tool that is simple and not too complex. We were lucky to get a lot of users very quickly. I think the combination of trackbacks and TypeKey has helped a lot. TypePad 3. We have the option to moderate all comments. DW: Do you think the release of 3. It was incredibly hard for me and Ben because a lot of the things that were said to us were really personal e. The problem was that we talked about Pro before we even realized that Pro was something we needed to rethink.
And I think we are doing a good job of that right now. DW: Now that you have a bigger office, bigger staff and outside financing, has Six Apart become something that is bigger than yourselves and out of your control? Or is it still your baby? Everybody here is really aligned with what we think the product should be.
MT: We have our die-hard developers who have been with us for such a long time. We also do contracts with a lot people who are prominent in the developer community. We just had an event for our developers as well as the general public. We like meeting people and actually hearing in person what they are thinking. I think what the developers contribute is immeasurable. Is this the start of a trend? What do you think this means for the future of publishing and Web building applications? MT: Absolutely. We think this is great.
I already have my own campaign, my own fundraiser. Kottke and Torres worked on this and wondered why they should replicate an authentication system. So we took this step out of their work, so now they can focus on making the service even better. We want to provide the building blocks that allow people to do projects like this. Being a larger company enables this. When we see people doing smart things, we want to reward them—by sending work their way, having them work with us, or just promoting services that use our tools well. It feels like a new era. DW: How do you see this new era coming together?
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. 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. 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 the funny thing about that was what I'd always 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 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. By ''05 I was like, oh you know, this isn't about this anymore. If I'm a normal person, I'm like One it's cheap to get 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. 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.
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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 , 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 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 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 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.
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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 Because they're like three of them  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. 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 You know WordPress inherited a lot of that b 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 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 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 so we could go down this list and it was like 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 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 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. 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 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 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 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. 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 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 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 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 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 Interviewer : Yup.
Dash : Yeah.
everybody else is doing it, so why can't I ?
And like that was like. I sent Matt a note. That was like sort of brilliant to do on the 4th of January  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 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.
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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 what I'm really interested in. And I think there are still large areas 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 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 I said this in a blog post not that long ago, maybe last year or so,  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.
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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. And for most 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 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 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. One, because we didn't know if we going to add ads at some point. You know? Because we're not gonna like 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 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!
And Firefox hadn't caught on yet, so there wasn't like ad blockers. And that was really one of those things of like And if you were there that early, it wasn't 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,  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 And the modern web 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 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 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. Open matters. Open enough matters. 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 And so there's a sense of design trumps open. Interviewer : Yes, that's very true. Dash : To some degree And that entire opportunity was carved out on design trumping open.
Interviewer : It's true. 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 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 even to some degree 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 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 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?
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