Matt Ruby transformed his experience with the tech culture into the hilarious Vooza show. Vooza describes itself as a video comic strip that parodies tech and startup culture. We chat about where he came from before starting Vooza, how they came together, their creative process and how they stay in business using a new spin on an old model for advertising.

[Mike] Hi, it's Mike with UGtastic. Today I'm setting down with Matt Ruby, the founder of Vooza. You can look at their videos at Vooza.com, V-O-O-Z-A.com, and @VoozaHQ on Twitter. They're the startup comic strip. You might have seen them or exchanged their videos through viral social media. Thank you very much for taking the time to sit down and chat, Matt.

[Matt] Sure, thanks for having me.

So Vooza.com, that's a very startup-y name. Where did you come up with the name, and where did Vooza the show come from?

The name, I actually registered the URL probably eight years ago, and I don't know why. I just made up the word, and it was available, and figured I'd snare it for some unforeseen future purpose. And it's funny, I heard nothing about it whatsoever for years, and then the work before we launched, I got an offer on the domain name.

Oh, really, and you're like, Oh, this is valuable.

Yeah, it was like, Oh, God. Well, we already had done all the branding, and logo stuff, and other things, and I just wanted to launch. So it's just funny, eight years of nothing, and then the week before I'm gonna use it.

Yeah.

So someone comes along, and he's like, Hey, I'll give you money for that.

So obviously you have some background in technology. How did Vooza come to be? Was it just out of humor that you were seeing in tech?

Yeah, I think it was a few different things coming together. I'd worked in tech for a long time. I worked at a company called 37Signals. I was actually the first employee there, and I worked with Jason and David on the books and some of the marketing stuff. I originally had started off there as a web designer. I think I worked there for 10 or 11 years, and I had also started doing standup comedy about halfway through that. And I'd been working out New York, so working as a comedian here, and doing a bunch of shows, and meeting a lot of talented people that way. Eventually I parted ways with 37Signals, and I was looking to do more comedy stuff, and I felt like, Okay, well it's interesting that I know all this stuff about the tech world. It felt like there was a lot of opportunities in the video space, which I still think there are. But the network model is crumbling, and TV as we know it is kind of falling apart, and something new is gonna rise up in its place. I don't think anyone really knows what yet. But it just seemed like there was an opportunity there from a business standpoint and then also just for me on a personal sort of unification theory mission of, how could I bring together the comedy stuff that I want to be doing more of and my tech background. So I sorta came up with the idea of Vooza as a way to kind of combine those two things and make fun of the tech world at the same time. I've been immersed in it for a while and seeing, anytime you have people who are really pretentious and lack self-awareness, there's room for--

Room for comedy.

There's room for comedy, and I think the tech world seems to have an endless supply of that.

So two really interesting backgrounds that you were doing standup and also 37Signals, which I'm familiar with them. For those who might not know, they're the Basecamp company now, and founder of Rails, and all kinds of neat books that are really great. But you mentioned the standup. I mean, going from a nice web designer position with a very reputable, solid company to standup. I mean, there's startup dreams, and then there's big risks. That was quite the longshot. You said you've done standup, but did you have a background in actually doing performance art like this in any kind of syndication before?

No, I'd actually been in a band for years. I was in a rock-and-roll band when I lived in Chicago, and I'd done that for a long time. And then when I moved to New York, that's when I got involved in comedy and started diving into that more. I guess through 37Signals, we did do some sort of comedic things making fun of the tech world. We had a fake site called Enormacom and we also did some fake press releases and things that were sort of embryonic versions of Vooza, making fun of the tech world, and how seriously people take themselves, and how they're focusing, a lot of times, seemingly on the wrong things. But yeah, I've always been making stuff, either writing, or making music, or doing standup. Eventually standup led into doing more video work and sort of creating sketches and things like that. So I think it's just sort of a natural fit, and I, personally speaking, just try to keep chasing whatever's exciting to me at the time or turning me on. And as I got more and more into comedy, I've done a lot too. I love doing it, but I also wanted to try to figure out, Hey, is there a way to make something that I like, and that I'm proud of, and that also makes money, and is sustainable, and isn't involving being on the road constantly, or something like that.

Right. That kind of leads me to the question of the team and the ensemble that you've put together. Are these other developers that you've worked with and kind of had a comedic vent with, or how did the Vooza team come to be?

Sure, they're all comedians here in New York. All the cast members on the show are standup comedians or performers here in New York. And it's interesting, because it's finding people who also seem believable in a startup environment, but also are funny and good at standup, so you have to find that good middle ground. And we work with a production crew and a director here in New York who also have a lot of experience doing comedy videos and comedy stuff. So I think for me, the more everyone involved in it can come from a comedy background, I think that's the hardest thing to do, is to make it funny. I think I can kind of plant the seeds of, Hey, there's the reality of the tech world, or, What's the real thing that's happening? and kind of explain it to people. And then they can kinda go from there and figure out what's the way to make it funny.

So that kinda makes you wonder then, when you do those, What is LinkedIn? kind of bit. Are these people just kind of ad-libbing, but they don't really--?

Yeah, those are episodes where I don't even tell them what they're gonna be talking about. We just turn the camera on, and we ask them to explain, you know, skeuomorphic design or something like that, and just hear what answers come out. So that's the fun thing about working with standups. They're good improvisers and able to think on their feet. Most of the episodes we do have scripts, but I'd say it's similar to maybe how Larry David films Curb Your Enthusiasm in that we know where the scene's gonna start and where it's gonna end, and there might be a couple words or bullet points we wanna hit, but we also wanna give people room to improvise or just make something up on the spot. Because a lot of times, that's the freshest or funniest part of the episode.

I have to say then, I think it was the one with LinkedIn, where at the very end, the lady who does the Marketing Director role, actually I wanna real quick, do your characters all have names?

They do, yeah. Here name is Laura.

Oh, Laura. So when Laura gets asked, she says, Oh, I have to take this, and she just walks away. That was so perfect for a marketing-type sequel. Just doesn't wanna acknowledge they don't know something. I've seen that in action, and so it was just perfect.

Marketing is a job that never ends. You're always putting a spin on everything, right?

Yeah, yeah. So you're saying that a lot of the people that you're working with are not techies or actors. How do they sometimes react off-camera, like, Really? Is this what startups are like?

Sure, I think at first when we started, because we've been around over two years now, coming up on 100 episodes actually, and at first, I think there was more of that of explaining, Okay, here's why this happens in the tech world, and what it means, and words like 'pivot' or 'disrupt' are being thrown around. But I think, actually, it's been interesting to me to watch, something I used to think was a very niche, sort of techie-only way of speaking, or knowledge base has really been expanded to the world at large. I think you see it in movies like The Social Network, and shows on HBO like Silicon Valley, and the fact that everyone's got a smartphone. Everyone's got apps. Everyone knows about Snapchat and Facebook and reads these articles about the valuations. And I think a lot of the stuff that we're touching on the show is sort of breaking out into a mainstream audience of people who, tech is just a way of life. It's not really this niche thing like it was five or 10 years ago, I don't think.

Right, yeah, it's so embedded in the culture. It's gone out of business magazines, and now it's almost, I mean, what is that show, Silicon Valley? That's a mainstream show that people are watching outside of tech culture. Even my sister-in-law who is a medical student, she watched it. So that says a lot about how that culture is getting out of actual Silicon Valley. As far as where you draw your ideas from, do you have a backlog of ideas that you work from? Do you guys do a spitball session, I don't know what it's called in the IT, entertainment biz, where you just come up and say, Hey, let's sketch out an idea? How do you come up with the scripts or at least the gist for an episode?

Sure, I just have a huge notes file or database. Actually, there's an app called Scrivner that I keep everything in. So there's a list of 100 different topics that I think might be funny for episodes, whether it's an article that I read in The Next Web, or TechCrunch, or some publication like that, or if it's interviews that I see with David Karp where he has funny quotes or something that I think is funny, or anywhere else. I read an article recently about the toothbrush test, which apparently is something that Google uses when they decide whether to acquire a company or not. The idea of Larry Page talking about the toothbrush tests, as soon as I see that, like, Okay, well, that's gonna be a Vooza episode. We have to do something on this. So then I have to learn what that actually means, and then be like, Okay, how can we make this funny? And then it's me generating most of the ideas of the scene, and then I work with other cast members and writers to actually write the scripts. So sometimes it'll be me explaining, like, Hey, here's this silly thing that happens. How can we incorporate that into the show? and just throwing out ideas. And again, the cast also definitely has a lot of input into what they think is funny, or even when we're actually shooting, being like, Hey, why don't we try it this way? or just improvising stuff on the spot. So I think a lot of times it's just creating that framework of, Hey, here's the subject and the topic. Now feel free to play around with it and see where it goes.

Yeah, and it just reminds me, I listen to SIRIUS XM. They have that comedy channel. I can't remember the name of the comedian who said this, but he described it where people asked him how he gets to be funny, and he says, Well, I watch the news. If you watch the news, you just gotta take it out of context, and it's hilarious. Even in context, it's often hilarious. It's true.

Yeah, I think that's a good point. So much of the stuff I see at Tech Blogs or the interviews that I hear or read, I'm like, Uh, this is almost comedy already. A lot of times it's just taking an actual quote from some startup CEO and just making it maybe 10% more absurd, the basis of what's ridiculous about it. People in the tech world are saying ridiculous things all the time that are almost hilarious, saying it with a straight face, whereas we put a little wink on it where I think people get the joke a like more.

Yeah, you only have to take it a like bit beyond what they're already saying to make it pretty absurd. I mean, the toothbrush test, I hadn't heard of that, but already, it's on its face absurd. And even go a little bit further and maybe make it... I'm not a comedian, so I'll just leave it to you, but you just gotta go a like bit further, and it's hilarious. But I'd also like to just ask a little bit about your process for shooting. What is a day like on a Vooza set? Do you do shooting every day? Is there a schedule? How many camera people do you have? What is that like?

I'd say we shoot about one weekend every six weeks or so, and we'll try to film between eight and 12 episodes during that weekend. So it's a pretty hectic schedule. This is usually how we work it. We shoot two days straight. There's an office that we film at in New York near Union Square. Our crew, it's a pretty skeleton crew. We have a director. His name is Jesse Scituro [SP]. He does a great job, and he brings his crew in. It's usually him, a DP, and a sound guy. Sometimes there's maybe one other person there, too. And then we have our cast, which is usually between five or 10 people there. And it's really filming sort of run-and-gun style where we're just trying to do things quickly but give people some room to play with stuff. We're usually filming the scenes five times, 10 times, with a two-camera setup, and then we'll switch the cameras and get reverse angles, and close-ups, and things like that, and shoot it a few more times that way. And then from there, the editor has something to work with to put it all together. So that's sort of a general overview of how we work.

Okay, so it is pretty loose. It isn't big, scripted, formulaic, two-camera, Lucy enters stage left, and it's pretty...

I view the script as something to fall back on. The script is a framework where it's like, hey, If we're rushed, or we run out of time, or no one else has any other ideas, then yeah, let's get that, and bang it out, and move on. But also, part of what I think is fun about the show is that we have low overhead, we have a small crew, but that, to me, is an advantage in a lot of ways. If you look at a lot of these other sitcoms on major networks, they've got crews of dozens of people, and this huge lighting setup, and every second that they're filming is costing them thousands of dollars. And that puts a ton of pressure, and makes you wanna move really fast, and makes you just bang stuff out, and gives you no room to deviate from the script at all. And I think you can sense that in a lot of those shows. They just have that sort of formulaic feel, whereas I kinda like working cheap, and with a loose crew, and a loose script. I feel like the more you get that playful environment and vibe going on the set and with the cast and crew, that comes out in the final product, that you can feel that it's people having fun, and there's something loose about the whole thing.

Right, and also, now that you mention it, the formulaic... like, you look at The Big Bang Theory, which is very popular. And a lot of people look at that as a view into engineering-startup-techie-programmer culture, but as a developer myself, I watch it, and it is just cringe. It's painful for me to watch, because I could see the setup, and I could see how they try to telegraph a joke or something like that, whereas it seems like more with Vooza, you just kinda let it ride.

Yeah, I think that show is not meant for actual engineers or tech people. I think that show is meant for people...

But I know a few engineers who adore that show.

Really?

It's hilarious, and I'm like, Ha!

Yeah, I'm on your side. To me, it's also just even that format of the laugh track, and even when they say a joke that's not funny, everyone erupts in this raucous laughter. I'm like, Are you watching the same show as me? Because that was not that funny. Just the whole thing kinda feels phony. Yeah, I'm much more, shows like Peep Shows, this UK show, or Curb Your Enthusiasm, or things without a laugh track. You know, Spinal Tap and all those movies, things that kind of let the audience breathe a little bit more and decide for themselves whether they think something is funny as opposed to a lot of sitcoms or mainstream stuff seems a little bit like it's spoon-fed to you. And I'd rather let people figure out for themselves where the punch line is.

Yeah, and even then, I've watched a couple Vooza episodes where I recall, it wasn't laugh out loud, it was more of an empathy, sympathetic, like, Yeah, they got it. I'm not gonna laugh. It's kinda like Dilbert where maybe it's not laugh, because you kinda wanna cry a little bit.

No, it's an interesting point, because I think that also speaks to, what's your goal when you're creating online video? I think it's a little bit different. We still wanna be funny and have it be good, but I think there is, when you talk about that empathy factor, I think that's also really an important part of why people share stuff. I remember being at 37Signals, and engineers were always sharing Dilbert cartoons with each other in our campfire group chatroom, and be like, Huh, that's interesting. This isn't always the funniest stuff, but people will be like, Hey, you're gonna get this. I think there's that, I wanna share this, because they get this thing, and I get it, and I wanna share it with you, because you'll get it, and why people share stuff online I think is an interesting psychological factor. But yeah, there's definitely episodes where we'll sometimes be like, Okay, this one's hilarious, and we'll hit a broad audience. And then there's other ones where we're like, All right, this one might not as laugh-out-loud funny, but I think engineers or marketing people are gonna be like, 'Oh, yeah, I know that person, or, I've heard that phrase, and God, I'm so glad someone's making fun of this."

So it kinda goes to the core audience. Do you schedule? I mean, that's an interesting point. Do you schedule the episodes where they go out in a way that's like, Okay, this next episode is gonna be targeted towards our core audience, or, This one we know is kind of a more high-end, general humor, so do you do that kinda planning with the episode schedule?

Yeah, I mean, there's no hard science about it or anything like that. We put out a new episode every Wednesday, so that's our fixed schedule. And from there, yeah, I think there's just a rhythm of, Hey, we just had an episode or two focused on engineers. Why don't we have one that's more geared towards designers? Or we had one that's more sort of, Anyone would get a kick out of this. It's just loosely about social media or apps in general. And then from there, we might be, Okay, well, now we can do one that's a like more specific to Sys Admins, or hackathons, or something like that. So I think there's just trying to be one note all the time. I think we're just trying to change it up enough from week to week that people still feel it's fresh. Or last week wasn't for them. Maybe this week applies to them.

Yeah, the Hackathon one, that was good.

Thanks.

Bathroom Hackathon? Yeah.

I think that episode is an interesting one, because that was generated by a tweet, basically. So we have our @VoozaHQ is our Twitter feed where a couple of times a day we're posting jokes about the tech world, and then it's always that sometimes one of those will take off and get retweeted dozens, or hundreds of times, or something like that. And then I'll be like, Okay, well that's clearly hitting some sort of nerve. How can we turn that into an episode? So I think that's been an interesting thing too, is sometimes the ideas being fed to us from the response on social media to one-liners that we throw out there.

Yeah, and the last question I wanna bring up, unless something else comes out of this is, you have a really interesting advertising model, one that, on UGtastic, I tried to figure out. I'm a one-man shop, so I haven't quite been able to figure it out. And I'm not nearly as entertaining as you guys, but whatever it was the term you used for the advertising, where it's not advertising, where you simulate a comedy, I've watched a few of those, and I watched through them not realizing that I'm not watching an episode. I remember there was the one with Jason Fried who is pretty funny where he's pretty deadpan, and you seem to be working around him a lot in the advertising. But it's an interesting advertising model, and I'm just curious about how you came up with it, and how is it working?

Sure, so far so good. I like to tell people we're just like a real startup, except we actually make money.

I'm like, Vooza the show actually makes money.

So from the outset, that was the goal, was to make money off it and to make this sustainable, and I think one inspiration was The Deck, which is an ad network that 37Signals and Cue Ball Partners actually started years ago, which was sort of ads dedicated to what they called creative professionals, you know, designers, or filmmakers, or people who worked on the web in different ways, and then partnering with advertisers like Adobe, or people who make fonts, or things like that, to kind of make ads. Hey, you can assemble this audience with this network of sites and have ads that are actually appealing to them and have it not be an obstacle, or an intrusion, or like, Hey, this is something from Toyota, or Snickers, or something you don't care about. Instead have it be like, Hey, we're the guys running this ad network. We're picking all the sites and people who are making this content, and then we're also finding advertisers who we actually like, and use their product, and think it's a good fit. And you can kind of create a whole ecosystem of people who are actually liking what they're seeing, and it's advertising, but it doesn't feel like it's bugging you. So I think that was interesting to me back when we did that years ago, and then I think you also had just the rise of native advertising and branded content, and that's sort of taking over content media. Words, and articles, and things like that, you start seeing that more and more and wondering, Hey, is there a way to do this in video? And I think also, people sometimes are like, Oh, this is a very innovative, futuristic way to do advertising, which to me is kind of funny, because it's also exactly the way advertising started on TV back in the 50s, or on radio where you'd have... Howard Stern, I'm a huge Howard Stern fan. I always used to stop his show, and do plugs, and I think it works in a couple ways. You got the actors or the people on the show talking about the products. That makes it feel much different than a typical commercial. It happens within an episode. We also do pretty impersonal ads, but a lot of the branded episodes we do are, the product is mentioned within the episode. But we try to do it in a subtle enough way that's not really annoying. Usually those episodes get to be longer. They're three minutes instead of a minute-and-a-half. I think there's a way to look at it, like, Hey, this advertiser's helping you get more content than you would otherwise. And also, we're working with people who, it's right for our audience. It's not just some random brand. It's people like New Relic, UStream, or Mail Chimp, or Insightly, people who, they're making products that are for the people in our audience, and it's kind of this mutual and beneficial thing. So the goal is to have it be advertising, but that's not really obnoxious, and annoying, and in your face.

It's not stopping, Here's a commercial for Brand A.

Exactly, exactly. And I think, again, it goes back to the fact that we're doing this with low overhead and with just a few people enables us to kind of, Hey, you and me are gonna get together and film this ad for New Relic, and it's gonna be us talking about this product, and do it quickly, whereas if it's Big Bang Theory or something like that, that's probably gonna be harder and more expensive for any brand to work in that way. And I think also, the other thing is that we're not trying to get Toyota, and Snickers, and these massive brands that are going through agencies and doing tens of millions of dollars, MediaBuzz. We're working with people who maybe have never done video content before, or who have an explainer video, but wanna do something that's a little bit funnier instead of just that straightforward informative style. And so these are people who, instead of having to go through an ad agency and waiting eight months, I can talk with someone in marketing there and in three weeks get the go-ahead, and get the check signed, and make something for them. So I think it's just a new way of doing stuff. It's interesting because the fact that we're small and doing it on our own, it's in some ways a weakness, but it's also helped us find the right audience who we wanna work with and the right advertisers who wanna reach that audience.

And I have to think, also, just because of the material you're dealing with, it might even be possible just to send them a clip that's relevant right to them and be like, Hey, here's a three-minute clip of an episode, and you're able to talk right to them, because if you do a marketing-heavy episode, and send it to the marketing department, and what'll happen, they'll be like, Oh, yeah...

That just happened. We've got a new video coming out about the new support rep at Vooza, and we have the script, and sent it to a company that has a support app, and now they're gonna be sponsoring the episode. So sometimes it works out great, where we're like, Okay, we've got this script that we think is funny. Who would be a good person to sponsor this? and run it past them. And that's actually happened a couple times. To me, that's great, because then it's not like we're making some bullshit content that no one actually wants just to please an advertiser. We're like, Hey, this is the funny thing that we're gonna do anyway, and people are gonna like it. Why don't you get your brand involved, and it's gonna be good for you, and good for us, and the viewers are barely gonna notice that's any different than any other episode. So it just seems like maybe there's a way to make stuff that works for everyone involved.

Well, I think I read somewhere that somebody said, it was in Honest Trailers or something like that, where it showed a picture of Mark Wahlberg in the last Transformers movie drinking a Bud Light. And the caption is, This movie brought to you by Mark Wahlberg drinking a Bud Light so, This episode brought to you by us thinking that this marketing thing is funny, so a marketing company came and supported us. So we'll get to do another episode next week.

Yeah, totally, totally, and we're also exploring other models. We'll be launching on Patrion soon in a way that viewers can actually donate to the show itself, just in case they wanna support us. The ideal is to have viewers paying you for exactly what they want as opposed to just relying exclusively on advertisers. But I think, realistically, maybe there's some sorta hybrid model we can do where, Hey, if there's people who really love it and just wanna throw us some cash because they wanna support us, and help us do it, and help us pay everyone involved, that's great. If there's advertisers who wanna reach our audience, then that's also great, and just play around from a business standpoint with, like, "What's the new way to do content, and make it sustainable, and keep it going, and how can we let people who like it give us money and let brands who wanna reach our audience also be part of it. It's like a real startup in that way of just trying to figure out how to keep this going, and how to make money off it, and what's the best path. There's new technology's coming out that make different approaches possible. My goal is to make good stuff that people like, but part of that is also figuring out the business side of things so you get to keep doing it.

Well, yeah, and there's a lot more people starting to think about that aspect now, the VlogBrothers. Are you familiar with their channel?

I'm not. I've heard the name, but I don't know...

They're huge, and they just launched a program to support media content creators who are not quite at the volume of use to really generate a living wage from their YouTube channels, but are large enough to have a sustainable audience. It's very targeted, and very niche, and it's like, Maybe you only have a 100,000 viewers. But they're in a niche, and you're making content directly for them. How can people support that channel that might not otherwise be easily monetizable?

Yeah, I think you also, like Live Events, and Merge, and other stuff, people are gonna start cropping up with all different kinds of ideas. So if you've got an audience of people who like you and wanna support you, how do you figure that out, and what are the different ways to actually turn that into money that you can use to keep it going?

Yeah, all right, well thank you very much for taking the time to sit down and chat. For everybody who's watching, it's Vooza.com, V-O-O-Z-A.com, and @VoozaHQ on Twitter. Matt, thank you again for taking the time to speak with me. It was a lot of fun.

Thanks so much. I enjoyed it.

Take care.