Interviewer: Today's Thursday the 14th of November and I'm speaking to Brian Veloso. Hi Brian.#

Veloso: Hello.#

Interviewer: I just wanted to start off by asking you a bit about your background, how you got into blogging?#

Veloso: Oh man, I got into blogging around, let's see... it was right when I was getting out of college. I graduated college in 2005, but right before then I was always... I've been a designer for, I guess, close to 15 years. Like on and off pro for about ten. And it was around the point where I was trying to figure out what my career would be that I actually really started getting into blogging. I liked blogging about design. Trying to figure out my own style, and hopefully chronicling it so people would learn from it later. So that was around 2003 to 2005 was when I started writing using, we were using b2 back then. WordPress 1.5, yeah.#

Interviewer: So were you designing themes then for that, like just using the stylesheet? Or did you come in when there was the theme system?#

Veloso: No, I came in before that. I liked... I remember being reluctant to actually switch to WordPress. I was a big b2 user for a long time. Because with the WordPress theming system sounded a little over the top for me. I like the sort of one page site. And it was really simple to just plug a few PHP variables in and it worked. And like the whole WordPress system just seemed foreign to me at the time. But yeah, I'd build my own stuff this pre- pre-theme system.#

Interviewer: So what made you finally move to WordPress?#

Veloso: I think it was just me wanting to extend the site. Like I kind of hit the limits of b2. And I saw what Michael had done with Kubrick around 2. So I'm like okay, I'll make the move and did that. I wasn't without its trouble though. [Inaudible] ... all I knew was Photoshop at the time.#

[Interrupted / inaudible]#

Interviewer: Let's try that again. So can you tell me about the troubles that you had when you moved from b2 to WordPress. As a designer, what new things did you have to learn?#

Veloso: I had to learn, just... I spent a lot of time with whatever... [3:00] I forget what the level of documentation was at the time, but like it was just a matter of trying to grok a lot of things that I didn't understand. Something as simple as a FOR loop. You know, when working on an archive page didn't... it didn't work well with my head. I didn't take any computer science classes in college, so I really didn't understand those things. So my... you know, I got to Google at the time as well and the... just the documentation that was growing at the time were my only resources to actually make the leap over. A lot of trial and error. And then trying to find a host that, trying to get it set up on my own. Like my own first like little development environment, trying to get it to work there. Or trying to live debug on, I forgot what my host was back then. But yeah, just grokking PHP was really what kept me from getting it out any quicker. It took me a little while to get it.#

Interviewer: So were you involved at all with the b2 community? Or did you just use the software?#

Veloso: I just used the software.#

Interviewer: And did it stop being developed after WordPress launched?#

Veloso: I think they were develop... it was kept up, but not supported after WordPress 1.5, I think. Which I was. I was completely bummed at that point, because I'd been using it for at least like a year or so. And I'm like ah I don't want to switch to WordPress. You know, the whole thing with people complaining.#

Interviewer: Oh yeah, of course. Did you get involved with the WordPress community then?#

Veloso: I did. I'm trying to figure out when I started getting involved in it. But, it was around the time when I had... I'd been using WordPress for a little already. I think WordPress was already in the 2 series. And I had the idea of taking some of my old blog themes and making them into themes that were widely available. That was new for me because I wasn't just designing for myself anymore. I had to clean up a lot of the stuff that I had done. That was a really good educational experience on its own. I know it gets like you know the precursor to doing open source work was making themes for people. I didn't like jump into the WordPress community though. I didn't like really participate in the discussions or anything. I was mainly a lurker. But if I had a... I'd garnered enough sort attention at the time, you know, if I had [inaudible] release something [6:00] like ChaoticSoul, you know the theme ChaoticSoul. Enough people saw it and used it that, you know, [inaudible] I kind of found myself immediately[?] kind of helping to debug and things like that.#

Interviewer: So what did you learn in the process of releasing themes at that time?#

Veloso: Well, I learned that... it's stuff I kind of would have learned otherwise being a freelancer at the time, but just being able to work with constraints that are not your own. The ways I saw people use ChaoticSoul for instance, was really interesting and eye opening, like ways that I'd never would have thought of. Different picture sizes, or people would be emailing me with like, oh the font's a little too small, can you make that configurable? Or something like that. And like things that I could either pick the curated designer position where I'm like no, that's kind of what you're going to have to go with. Or you know I could delve into the code a little more and see if I can make stuff like that configureable. Just being able to build stuff that other people would use, and you know kind of display as their own was a big challenge because I had only really designed for myself at the time. I had done a little bit of client work. I was trying to garner that. I was trying to get a job in the industry. But I'd never really worked with a... in the mindset of building for other people, yet. And I think that's what theming opened my eyes to.#

Interviewer: Did you... what did you think of the theme system?#

Veloso: Once I got a handle on it, it worked out pretty well. Like it seemed... that became what I knew. Like I knew how to make a theme. I knew how to make a good theme. I think my perfect point, my peak, was around the beginning of the 2 series, before like a lot of the more dynamic features started coming out, later in the 2 series. Like I liked, you know, just having a blog with an index page with a list of your posts and then detail pages and maybe an about page or whatever. But when they started getting a bit more, when the themes started getting a bit more complex, was when I'm kind of huh, I'm kind of falling out with this. Like I can't... I sort of like bunkered myself in the mold of like this is what a blog was, and I was really good at doing this brand of blog. So I surrounded myself with that part of the theming system and I knew it really well [9:00] and you know the theming system really taught me a good amount of PHP, at least within the WordPress ecosystem, but I never really expanded past that or had ideas that would allow me to expand past that. It was really just seeing the other themes that started coming in that were becoming I guess quote / unquote more popular than the ones I had done at the time that were like, oh, maybe I'm just a, I'm just like growing old or long in the tooth in the community.#

Interviewer: So did you notice a shift in the types of themes that people were wanting?#

Veloso: I did. There was a... it was around, I think, 2006 or 7, where the themes started becoming magazines. Like the magazine, very periodical inspired designs. I have trouble thinking of the specific names of people that... as examples of that, but... like when the default theme changed from Kubrick, that kind of really ushered in a, you know, this is the new WordPress. This is what you can use WordPress for, it's not just a blogging engine. You can use it for pretty much anything. And people did use it for anything. And I was very much of the, sort of the old guard, of like WordPress is a really good blogging system. And I kind of didn't agree with where it was going so I kind of found myself like, sort of shying away from advancing. I mean it was kind of like looking, you know hindsight being 20/20, it was kind of a missed opportunity to do that, but I guess that's just, that's just me. That's just my personality.#

Interviewer: So what didn't you like about the direction it was going?#

Veloso: I thought that... I didn't like the fact that people were sort of hammering square pegs into round holes. Like it didn't... I couldn't like grok the whole notion that, oh, you can add a payment system to do like subscriptions on this. I'm like, what is this? This is not... People are extending it, which I should have, again hindsight, should have been a good thing. Like, oh, people are able to extend this, it's such an extensible piece of software. I mean that's such a valued paradigm today, is something being extensible and you can just add anything to it. But back then it's like, you know, WordPress was a really good piece of blogging software. I don't agree with any of these things. What are people doing? They're like bastardizing the... what this was meant for. Coming from the whole b2, WordPress thing. I mean, like people just use this for blogging. So it was just kind of that like there's a line in the sand and I just couldn't see myself crossing it. I'm sure if I had, if I had spent [12:00] a good amount more time, or had gotten a project from a client that would have required me to use that, maybe the fates would have been different to me, but at that point I was, yeah, this is a good piece of software. There are other pieces of software out there that will do what you're doing a lot easier, but you're still using WordPress? It was kind of at that point where, like, well ok, you kind of do that and I'll just keep making blog themes and stuff and be happy over here. Because you kind of had that luxury where you know there were just so many ...#

Interviewer: Why do you think people were doing that? That they were trying to put this square per in a round hole?#

Veloso: I think people got really comfortable with WordPress. And it was just that base that just seemed so easy to work with that, you know, you could... And the WordPress plugin system let you do anything. You could... it became like the first of its kind of a... some weird, mutated MPC framework, that you could just with a little bit of PHP and a little bit of, kind of tweaking around what certain things could do, like oh, this is not a post [inaudible] post anyway on it. Because it works. Like, experimented with it and because they didn't want to build it from scratch, they decided they could just lump feature on to WordPress, and it would work. And that would be enough. Like a payment system. Or a forum. Or whatever. Like it would just work. And I think a lot of that activity started to happening and then it just snowballed out of control. People just... I remember like later in my freelancing career, going to clients and being like why can't we do this with WordPress? And I'm like, but that's not the right tool for the job? It's the whole square peg in the round hole thing. Like it's not. People would start kind of... like clients that weren't exactly educated in what, the expansive software that we have. And the many different languages and the many different paradigms. I mean this is when Ruby on Rails started coming up. Like this is what you can do with software. But like we can do it with WordPress too. But it would be just like knocking your head against the wall. So much headdesking going on at that time. Because like you couldn't explain to clients that you can, yes WordPress can do it, but there are other ways as well that you should explore. But the community had gotten so used to the fact that WordPress was this sort of basis for everything that it really, I guess, for a lot of people that I knew, [15:00] it was very frustrating to have to always be battling WordPress when you knew there was another more curated, more specific solution out there. And I think it was just because in the beginning people would just do that sort of attaching on of anything. I have this WordPress site. It's working. I need this other thing. Somebody built a plugin for it. It works. We don't have to change it at all. There were never any barriers. There wasn't like a point where, oh, like with the whole Rails / Twitter bit back in 2007. Oh, it's not going to scale. Rails doesn't scale. WordPress never ran into that because people would always like, oh, okay, well you're using it for this? Well it will scale because we'll make it so. WP Cache or whatever. Things like that. Just attach that on. So you had this Frankenstein of a piece of software that was made from a blogging system that could do absolutely anything and people saw that as sort of the dream. It was really easy to get from, that was agile back then, it was really easy to get from nothing to something to everything in a really short amount of time because everybody had built everything for WordPress.#

Interviewer: Do you think that's a good thing now? Or do you still think, you're like oh, god...?#

Veloso: I've evolved a lot since then on that. I would like to think that people would be more aware of what their choices are. I understand that when you're working with Ruby on Rails or you're working with Jango or any of those, like KPHP or any of those frameworks, you are starting from scratch. You are having to build data models from scratch. You are having to build a lot of that stuff. But WordPress you could just upload it and run wp-setup and you're done. And it's like, ok start. And was just that the fact that it was PHP, the fact that you could... the setup was so easy and then the barriers, the fact that there were no barriers when it came to adding stuff on to it. Do I necessarily agree with it now that it's still used? I haven't really been versed with what WordPress can do now. Maybe... I've seen it grow. A lot. And I'm sure it's definitely more better positioned today than it was when people were just kind of building stuff for it for fun and it never really was made for that. But I think they leaned into it. Automattic leaned into it. And yeah.#

Interviewer: So can you tell me about your involvement with the Shuttle project?#

Veloso: Shuttle. So, uh. Michael and Khaled...#

Interviewer: Michael and Khaled and... Owen.#

Veloso: Yeah. Yup. They invited me to the Shuttle project around the time that I had, I was working at Facebook at the time and I think I had just left and they were looking for people to recreate the WordPress admin. [18:00] And a lot of us had kind of seen like, kind of remembered the original WordPress admin as being something that did need some design love. And we wanted, they wanted, this nicely designed and opinionated theme and I just found myself... I was interested in it too. Like I had worked with the WordPress admin with so many projects at that point, not only my own, but also other clients. And it just seemed like a logical step. Like, okay I've contributed to the community by releasing themes but maybe now I should start contributing to the betterment of the actual software. Like the Shuttle project proof of concept. But it never... [inaudible] like the higher ups in the WordPress community at the time or there just wasn't enough implementation there, like a lot of us were just kind of... we were throwing mockups at each other. It was really hard to get us together too. Like I think I only had one or two calls with them about it. We all had real life to deal with, so like the calls were few and far between. So the energy was there, the good intentions were there, but looking back it really needed somebody... it really needed, I think, more support from the WordPress community as a whole and not looking at it like a pet project. Like all these designers are going off doing their own thing. People got excited about it, but not to the point where like how can I help you implement this. And it was really hard to get things into WordPress at the time. And I think still, when I was at Automattic, it was hard to get things into WordPress anyway, so getting something like Shuttle in, which was just a complete rethinking of the entire system was almost... was everything but... destined not to work out. And I say this with no disrespect to any of the people that I worked with, it was just sort of a matter of circumstance that some things just didn't line up that the project was taken seriously by the parties that needed to take it seriously. It didn't feel like we had the support in order to like oh if we had something done, we have Shuttle done, you know... This was before Dean Robinson and his admins came out. Like this was sort of the precursor to that. So if Shuttle had come out maybe a couple of years later, where it could be a plugin admin, [21:00] it probably would have worked out a lot better. But we came into it thinking, yeah, we need to replace the WordPress admin. And WordPress was like the only thing you could do was replace the WordPress admin. We couldn't offer it as a plugin back then. So different timing...#

Interviewer: Why couldn't you offer it as a plugin?#

Veloso: I don't think at the time that we created, that Shuttle was being discussed#

[interrupted]#

Interviewer: I was asking you why it wasn't a plugin.#

Veloso: Yes, I think at the time, I think it was like 2.4... my versions are way off...#

Interviewer: Yup#

Veloso: ... the Shuttle program happened at a time where the plugin system did not support the replacement of the admin.#

Interviewer: Right, okay.#

Veloso: It wasn't until the actual redesign of the admin came out, with like 2.4 or five, that you could actually plugin to and replace the admin templates. Like the hooks weren't there at the time.#

Interviewer: Okay.#

Veloso: And if they were there, I think that the Shuttle project would have worked as a plugin alongside like Dean Robinson's stuff. Again, a victim of circumstance. It just was too... it was ahead of it's time at the time and... just the lack of community support. Because, I guess I can understand, because we're coming in, opinionatedly trying to replace something that a lot of people were trying to use. Whereas a plugin you can opt in, if we were to replace the entire thing you couldn't opt out of it.#

Interviewer: So Matt set up a mailing list for you. Did you guys take that as sort of tacit agreement that you guys were redesigning the admin? Or did he ever say to you, I want you to do this? I think... did you have his backing?#

Veloso: No. If I remember correctly, in some of my conversations with Matt, at my time at Automattic like he was, he never really seemed that enthused about the Shuttle project. Like he knew of it, but it was almost like, kind of, maybe this is going too far, but, it almost kind of like jokingly, like he was kind of joking, or thought it was a joke. Like something that was never really viable, that wouldn't really be accepted in the community. That's... I was kind of taken aback knowing that that was something that I had wanted to do while at Automattic. Yeah, but, I don't know... the support, I never really got a warm and fuzzy feeling from Matt talking to him about the project. So I don't think there was really any, at least from what I know, when I joined the project kind of late, there was never really that feeling that Matt would have ever reached out to us and said [24:00] yeah, I support you guys, we can work this in somehow, with enough community support. There was none of that there I don't recall.#

Interviewer: Do you think it would have been more successful if it had been more public, the discussions, as opposed to on a private mailing list?#

Veloso: I think so. Yeah. It was definitely a... it was in the era where designers kind of did their thing and threw it over, you know, the waterfall system, they threw it over the fence. I do believe that it was, now knowing the power of open source now and the power of being able to openly have those discussions. I think the thing was that there was an immense fear amongst designers that having developers come in and start to critique stuff, and it's still kind of the problem now, is that you have developers come, and everybody, and they're all designers all of a sudden, right? So they start critiquing things, and it's like well, no. We made these decisions because A, B, and C. And they're like, well I still don't like it. I'm like, well, you know, that drove designers into little holes where they worked together and then when it's really close to finish and there's really nothing that a developer could come and rip down, it would be like, oh, well, you know, it looked beautiful already, so people would be like okay we'll take it. But we found back then, that involving developers in the community, in the conversation, would have... it would have been designed by committee. It's like people would have been making fun of the font size, or making fun of the blue. Things that we felt very strongly about would be easily taken down by engineers. If we were more open, would it have been better? I'm not sure. I think it has really taken the last seven years of development and design, together, add the agile movement of putting the hybrid of making designers becoming developers, and developers understanding design more, I think it took that understanding and that maturity to be able to involve everybody in the project from day one and understand that we are not trying to take each other down. And that still happens in the community, but definitely not as much as it did in '05 and '06, '07 where it would have been really scary to bring people in and have them take the project... not respect what we were trying to do. So I'm not really sure if it would have been any different. It might have suffered... it might have died faster. Or it might not. We might have gotten a good amount of developers who really respected it and then would have been able to take it forward. [27:00] I guess the moral is you never really know unless you try. And we didn't. So we never really got to know.#

Interviewer: So what did you learn from the process?#

Veloso: I learned that there definitely needed to be more, I hate the word project manager but, it seems like there just needed to be some... there needed to be like milestones. There needed to be... we needed to take the project seriously. And we needed to put constraints on ourselves. Because we didn't really have any constraints. You know we got together when it was convenient for us, we designed when it was convenient for us, you know. We even had trouble keeping up with the releases. Like releases would go by and the Shuttle project wouldn't, you know... oh, the Shuttle project right now is against 2.3, but you're all the way to 2.6 now, so, you know, we have to keep up with it and the new features that were coming out with each release. So just learning about being able to have constraints, and keeping, really the life of a... learning about the life of a open source design project is... it was really something new that, for me at least, working with other designers to attempt to improve something that people used on a daily basis while in the open source movement, it was... it was just interesting seeing the dynamic between the designers ourselves, like what we agreed on, what we disagreed on. Because I had never really had that type of interaction outside of a company before. Going back to your prior question, I would have liked to see, it would have been an interesting experiment to see, how we would have interacted with other developers if they had gotten more involved with the project to see how that sort of interaction would have played out. But yeah, things like project management and treating it like a client, treating the project like a client rather than treating it like a side project because, for designers, side projects are... they take forever. It's not something you ever put that much time into unless you kind of wake up in the morning and are like I'm going to finish this today. Alright. When you're working with five, six other designers, it's never going to happen that way unless you have some kind of constraint.#

Interviewer: So you joined Automattic in 2006?#

Veloso: Yeah, late 2006.#

Interviewer: One of the first ten employees, something like that.#

Veloso: I was number eight I think.#

Interviewer: Number eight. So how did that happen? How did you end up joining Automattic?#

Veloso: It was a... by then I think, pat myself on the back, but ChaoticSoul was like the fourth most popular WordPress theme at the time. And I had gotten a lot of good design work after my time at Facebook [30:00] just doing WordPress themes. Like it felt like I was in my groove. I was actually at Web Visions in Portland in the middle of, near the end of that year of 2006. And Matt was there. We had known of each other. We conversed a little bit. But I had found out from a friend that they were looking for a designer. And I had actually gone into... I found him at Web Visions and we had... he was happy to talk to me and we went to a nearby diner and just like kind of sat there for about and hour and half just kind of talking back and forth. And by the end of that conversation I pretty much had a job. So that's how I joined it. And then I met the other people on the team at the time and had a little outing in San Francisco. I lived in San Jose at the time, in the South Bay. And a little retreat with them a few weeks later.#

Interviewer: What was that like?#

Veloso: It was fun. It was really cool working for a really small company. When I joined Facebook I was number 27, but by the time I left we were over 200. So like it grew really fast. I really like the small startup, and to this day, I still love that small startup feeling. It was a bit cool to be the guy that would help press the red button of WordPress.com to release stuff. Like a release... I had worked on a few themes and such. Just the whole... we're all in this together mentality that we, that any of us could break something, but somebody else was there to back us up and fix it and we're all having a good time kind of bit. It was nice. The personalities were very interesting. Like working with somebody like... I kind of knew how to handle Matt because he was a little bit more an animated figure than like say, the previous CEO I had worked with which was Mark Zuckerberg, so I kind of knew how to handle that. But there were like the very, there's some very strong personalities on the WordPress team at the beginning. And then there was, what's his name, Toni, who was the...#

Interviewer: Toni Schneider#

Veloso: Yeah, Toni Schneider who butted heads a little bit because, I don't know, I guess expectations of what I was supposed to be doing and such. And I think I was their first, no I wasn't their first remote, obviously they were all remote, a good amount of them were remote in some capacity.#

Interviewer: So what did you butt heads with Toni over?#

Veloso: Well, I think, I kind of had my... [33:00] I think Toni didn't necessarily agree with my work ethic. Like I was sort of... I worked in very loud spurts. Like I'd have something and I'd take it to finish and I would just kind of have a cycle of taking things and finishing them. Even before that, like I kind of butted heads because of what I thought I should work on. And what they thought I should work on. I didn't join Automattic to make more themes. Even though I did make a few themes for WordPress.com at the time, that turned into my job. And I'm like well, you hired me as one of the designers, like I think I was the first designer on the team. And I thought I could, I had a feeling that I could make more of an impact on not only .com, but .org as well, and I had worked on bbPress at the time, like release 15 for bbPress and created the site for it. And the logo for it and stuff. And that was fun. That we would be able to push forward. But it wasn't stuff that they kind of, they didn't really put their blessing on that. Like they just really wanted me to release themes. So like there was really a, not just with Toni but with Matt as well, like this is kind of what I want to work on guys. And it was never really, they never really blessed that activity. My stint in Automattic was pretty short. And I think it was eventually because of the... I kept hitting a brick wall with like you guys want me to make themes, but I'm trying to advance the admin. You know, I'm like, I'm here, I'm a designer. In Automattic. What do people want out of a designer at Automattic? They want like stuff that they can use. And I really thought that would be like the admin and stuff. And so I started like trying to push that. I guess I was a little errant. I was a little rogue at the time. Like I knew what I wanted to work on. I'm very strong willed like that. Like you're telling me what to do, so I will do the opposite. Which is kind of... It's such a small company, you kind of need everybody to go together but it kept happening, where I'm like can you work with me on this? Can I work on that? I will do both. But I never got support on the other end. So I just kept finding myself wanting to do something else. I completely lost motivation on the theming end. I'm like I can't do themes, you're taking me away from things I want to do. So eventually the agreement ended, I believe in February, no March or April of the year after. And then they hired Matt Thomas after that. Who completely worked with them, and I'm glad he's still there and that he was able to make lemonade with the lemons that I had left. [36:00]#

Interviewer: And Matt has just redesigned the admin. Seven years later.#

Veloso: Yeah. All of that happened.#

Interviewer: So what did you want to do? What did you see were the problems with the admin at that time that you wanted to fix?#

Veloso: I thought it wasn't that... the user interface, the user experience, wasn't that great. It like, if felt like you were... it didn't look polished. It didn't look like something that you could present to, like have content editors go into and use on a daily basis. It felt really clunky. The form fields were very small. Uploading images and supplying custom data was just, didn't feel intuitive. And like I'd actually had a good amount of discussions with people. Not only taking what I had learned from Shuttle, but just talking with people that I'd built sites for, sizable themes and sites for, and they kind of talked to me about their qualms with the admin. So I kind of came into it... with the... with my attempt at the redesigns I think they were a little bit, my style wasn't necessarily right. So there was a bit of a backlash around what I was trying to do. For the community, I'm glad that happened. Because, cooler heads prevailed in that, at that point. Like it took a little bit more time to build out something that, and build out a design language I guess which is what was needed, which was what WordPress was sort of lacking, was an overall design language that would later come into the admin that wasn't there when I was there. I was just kind of rip-roaring wanting to be that, you know, guy that made everything better for everybody. I didn't take my, I was still kind of immature startup guy at the time. Looking back on it, I probably would have handled it differently if I had to go through it again.#

Interviewer: I think everyone could say that about things in their life.#

Veloso: Of course.#

Interviewer: The people who ended up at WordPress.com then, or at Automattic, did they spend most of their time working on WordPress.com or was that their main focus or were they still getting involved with the .org and the community stuff?#

Veloso: .com. It was all .com. Like when I was there, it really felt like things would come out on .com first then come out on .org. Because it was easier to, you didn't have to go through the vetting process and the QA process. You can mess up on .com and then fix it later. But if you messed up on .org, that's a point release that you have to release. And it's like aw crap, now we have pie on our face and this doesn't look good. They could experiment on .com and I think that was the other thing with, the other thing I butted heads with [39:00] Toni was around the work on .com wasn't necessarily just to make .com better, it was because that was our source of money. So obviously as an investor he really drove sort of that we need to be working on .com, we need to be working on VIP, we need to be working on themes, paid themes, things like that. So I kind of, I was sort of like the organicness of a startup and not necessarily working for money but making great things that eventually make money. So I guess being invested in stuff and understanding that now, the sort of dynamic that happens now with startups that are VCed, you need to... you are beholden to him. You are beholding to people like him. You have to do that because they're your lifeline. They pull the plug and your guy's gone. I didn't understand that back then, so it kind of created that clash. Like why do we keep... there are people that I loved, I came into Automattic loving .org. That is what brought me in. Community. That's what I wanted to work on. BbPress, or something like that, like I really liked the way bbPress worked, but it was completely, it was just completely ignored. I had to... what, I forgot his name, but I had to kind of work on the side to get bbPress like in a place where people would be... wouldn't kind of questions the site to download it. It's like huh, this doesn't look like anything Automattic offers, but yet I'm supposed to download bbPress off this site. So things like that weren't necessarily generating a buck every single time somebody downloaded it, I still found those things important, whereas everybody else was sort of like .com, .com, .com, themes paid, themes VIP, you know. That was what we needed to work on. And I think there was a balance that was created as they... I mean still had Gravatar at the time. I mean we had Gravatar and then we had things like VaultPress and things that started coming out, they diversified their model so I guess they didn't really need to be so hard on .com. And it seemed like the WordPress community as a whole started to lighten up again after diversification happened, after Automattic started growing a bunch. I mean that's from an outsider's point of view.#

Interviewer: Do you think other people who were at Automattic at that time felt the same frustration? People who had been hired from the community?#

Veloso: I wish I had been more forward with kind of figuring that out, because I definitely felt like something was there, [42:00] that we weren't working enough on .org at the time, but everybody was being a good solider, I think, and you never really saw it. You could just kind of speculate and that's really all you could do. But it was almost at the point like bringing... they were so close to the team, almost bringing it up would easily throw yourself, make you throw yourself under the boss. It's like oh wait, huh, he's out of ranks. Because he's asking like... I didn't really feel that close to anybody on the team where I had, I could speak with them on a sort of quote / unquote real talk sort of level. I'm sure it was there though. Because there was that big split between wanting to help .org and having to do .com.#

Interviewer: Did you ever see anything go into WordPress the product, WordPress.org, that came from WordPress.com and was clearly to benefit WordPress.com?#

Veloso: That's a good question actually. I don't actually recall anything during my time actively working with WordPress that would have sounded that alarm to me. Because things were definitely siloed off of both. Like if you wanted VIP features, you had to be on .com because obviously you could host .org anywhere. But yeah, if you wanted certain themes you had to be on .com rather than on .org... so it's almost like being on .org limited you from gaining some themes that were out there because they were only being released on .com and stuff. That's what I did see, was the .org was being kind of shafted for things that .com would get.#

Interviewer: Did you release your themes on .org as well? Or were they kept for .com?#

Veloso: They were kept for .com. Yeah, the themes I did release were solely for .com.#

Interviewer: And what was the wider reaction in the community to the setting up of Automattic and WordPress.com? Do you recall?#

Veloso: From what I remember, people did see it as sort of a "oh, this is how they're going to make money." The hosted bit didn't seem to go over well with the people that were... the people that had been in the community for a long time. [45:00] It's like nobody saw how they'd use it. It's like why would I want my own WordPress.com account when I could just deploy this anywhere. I guess that it was hard understanding that .com was for a completely different market. There was Tumblr at the time, and still having it now. Maybe that was just their way to get into the hosted bit that would try and steal some of the market share away from growing services like Tumblr. Other than that, it was just I don't need it so I'm going to rat on it. It was just not for our market. I think some people got used to it. Some people used it. I think what later came out of it was the entire WordPress ecosystem. Like having to have a WordPress login in order to do things. I think that's what really rubs people wrong the most. Like I need a Gravatar. "Oh! I need a WordPress blog too to get a Gravatar? Um, that's not right. I don't think that... I shouldn't need that to get this." To this day people still complain having to get a WordPress.com blog in order to get a Gravatar account. So things like that where you're kind of forced into their walled garden in order to use some of the things you can take outside of the garden, like Gravatar being the prime example. I mean people have found good out of the .com, like the VIP system and stuff. Not having to worry about hosting and such. So it's definitely served the people that it needed to serve.#

Interviewer: And did you feel any animosity toward you for being hired by Automattic? Some people have said that there was a bit of a division between people who would get picked to get hired and other people who wouldn't.#

Veloso: It definitely felt like there... among close friends, no. But it definitely felt like... it didn't help that I felt like I had a good amount of leverage from where I was. So the fact that I felt that kind of rubs people that were more quote / unquote active than me in the community the wrong way. It's like what's this guy doing here controlling this kind of stuff? Why is his say any better than ours? It really, hiring people into those roles, especially like designer roles because it's all user facing. It's all stuff that will affect people. It's not necessarily like oh, we've made a backend change. People aren't going to throw things up because of that. Yeah, for the short time that I was there, [48:00] there was definitely some, not the best of support from like people. People I didn't know I couldn't interact with. I couldn't like talk to. It was just like flaming back and forth. And it wasn't that... I think as a designer you had to be more... I think this worked for Matt Thomas because he wasn't as out there with his blog as I was. Like I... that was part of me. Avalon Star was part of me at the time. And like that was going to be my horn no matter if you wanted to hear it or not. And people just kept coming, because they knew I worked for WordPress. So like if I talked about things, that comment section would be just riddled with people either with feature requests, with critiques with what I was doing, or criticisms and/or flames. So, it was like... I called that to myself because I didn't step down from my pedestal - pedestal is the wrong word - my platform, my soapbox. At the time. So it was again a victim of circumstance. I'm sure if I had like kind went quiet then there would have been... I wouldn't have had the target on my back that I did. And it probably would have been a little bit easier to deal with. But nope. I was stubborn.#

Interviewer: And did you, when you finished at Automattic, did you back away from WordPress, the WordPress community, as well, and move on to other things? Or did you still...?#

Veloso: I started to. Yeah, I still did client work for WordPress. It was still what I knew best. It was still what I knew most. I started to get, it was around 2007 that I started to move into the Python community. And I started to learn Jango because I had some friends that were learning it at the time, and I just felt like I did need something different, but I did do client work for it. So I guess to answer your question, yes, I did start to shy away a little bit. Because it's like now after the experiences I had with Automattic the company I didn't feel like I could contribute to the community, in anything other than just releasing themes, that would feel right. It just like... it didn't end well, so I didn't feel right about still being an active part in it without feeling awkward every time I posted something or whatever.#

Interviewer: So why didn't it end well?#

Veloso: Because of the butting heads, I think. I had lost the motivation that was required to, that they had required of me, like the motivation to make themes. I couldn't just... I couldn't be the theme driver because I'm so like why? If that's what they want me to do, and I'm not going to do it, then it's not going to work. So that's eventually what ended it. I got a call one day, and we just kind of agreed that it wasn't working out. [51:00] I kind of went right back to freelancing. Like that day. Yeah, it was Toni that called me that day. I mean I saw it coming. One side was going to end it because we just weren't agreeing on things. Things weren't getting done because we just kept butting heads. I mean I hate that it ended that way. I wish the relationship had worked out a little better because I had loved, you know, WordPress was sort of where I came from, so it was hard to come to terms with the fact that this is the way, this is the company, this was the inside of the company that ran what brought me to it. And it was too bad. I just wasn't the right person. I wasn't necessarily I didn't know what I was getting into. It was different than what I thought I was getting into.#

Interviewer: Did you get the feeling... sorry come again...#

Veloso: Oh, no. I can end my thought there.#

Interviewer: Did you get the sense that Toni was running things? Or Matt? Or did you feel like they were in partnership?#

Veloso: I felt like Toni was running things. I really did. I mean if Matt was running things, then I would have had discussions with Matt about what I was doing at the time. But I had discussions with Toni. It was... And Toni, for better or for worse, just... we just didn't... like see eye to eye. And I guess I didn't... I saw him... he may not have been running the company in the way I thought he was but I thought he was, so that's how I carried towards him. I didn't think it was right that the investor was running the company. That the investor was the... I thought Matt, I had so much respect for Matt because like it's because of Matt that I had started blogging in the first place. Without b2 there would have never been WordPress for me, and there would have never been this job. So I mean I had an immense respect for Matt. It just felt like, you know, that's who I should have been talking to. And I carried this... my only other experience at the time was Facebook, and I had a really good relationship with Mark Zuckerberg at the time. So I felt like I would come into this situation the same way. That I would have a really good relationship with Matt and we'd carry on and if there were any problems we'd talk it out because, like he's the guy I had respect for. And all of a sudden I see Toni there. And it's like, oh, he's from True Ventures. Ok, he's the guy, he has the money. Alright. I understand what's going on here. And like my little deviant self didn't really... I have trouble with authority. [54:00] I just didn't mesh well. So yeah, I definitely thought from my end that Toni was running it and I wish that it felt like Matt was. I wish I had gotten that impression.#

Interviewer: What was Matt doing then?#

Veloso: He was being a CEO. He was talking, trying to get... trying to help Toni get VIPs. He was not moving as much product. He was definitely hacking on a lot of things at the time. But it was definitely the others that were kind of moving the actual pieces to get stuff into .com and .org, so I definitely thing that Matt sort of switched into more of a... the business part of a CEO role at the time. But still with a high sensitivity towards the product. So I could go and talk to him about oh I have this new theme and I could show him and, you know, he wouldn't shy away from it because he still cared. But I didn't think he was coding as much as I thought he would when I joined. Like he was really in that transitional period.#

Interviewer: Did you get a sense that Toni cared about the open source project? That is was important?#

Veloso: I don't think he did. And if he did, that... I think those words would ring hollow. Like he... I just... didn't think that like the roots of this entire company which lied in the open source project were really cared about. There were times when we'd be hounded, like even in that short four month, five month period of time like that, you know, people were waiting for another release and it just seems like we kept just focusing on .com. And even people within the company were getting anxious of like, we should get something out. We should... you know, why aren't we porting things over to .org to get out, just get out to people. And we did have a release then, but like, I don't know. Maybe the anxiety was just a lot higher because you're in the line of fire now. So it just felt, the pressure felt that much higher to get something out because now you have something to do with it. Now you're in that crew of people that do pull the plug. That do, you know, push the release out. So maybe it was kind of overblown at the time. But for Toni is was just, it was just .com the entire time. I don't think I ever heard him really talk about the open source project at all.#

Interviewer: Was the open source project - the development, the decisions - really being driven by the people at Automattic?#

Veloso: I don't think that they necessarily wanted that to happen. They really respected the openness [57:00] of the community. There were a lot of people, who I'm sure, you know, would have been prime Automattic hires at the time if they could, that worked on the project on a day to day basis more than people that were at Automattic because we were working on .com the entire time, so they were trying to push features on .org. So I think that we did definitely did make like some hard decisions, like we're not going to do this. Like a lot of the sort of BDFL sort of decisions of yeah it's a great idea but we're not going to put it in now. Like define our implementation steps. But as a whole I think it was very standoffish. Just like we're not going to assert our dominance over .org because we're Automattic. That didn't change.#

Interviewer: I see there was just one release during your time at Automattic, which was 2.1. That was January, so nearly a year after you started. I guess everyone was distracted.#

Veloso: Yeah, I mean, that's really when .com was coming to form and it was, I guess, yeah, the 2.0 series had just started (thank you for the clarification) and ...#

[Interrupted]#