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Real Profits with a Fake Startup: Matt Ruby of Vooza

Matt Ruby is the CEO of Vooza, a video comic strip pointing out the absurdities of the tech startup world. Matt will be delivering a keynote speech at Future Insights Live in June, and if it's half as delightful as my experience researching his work to interview him, we're all in for a treat. Enjoy. 


Ian Murphy: You were employee #1 at 37signals. Which was your hobby at that point, web design or comedy? When did that switch?

Matt Ruby: It's true. I started at 37signals in 1999. At first I was designing sites but eventually I shifted to more of a media-guy role (writing books, blogging, video work, podcasting, etc.) I did comedy on the side but I wouldn't call it a hobby. To me, a hobby is something like stamp collecting. Comedy swallowed up the rest of my life since I was performing and writing all the time. It's more of a joyous black hole that sucks ya in.


Can you remember a specific instance where something ridiculous/hilarious happened there (or at another tech firm), and you thought "wow, you can't make this stuff up?"


This whole "I work 80+ hours a week" thing in the tech world is bonkers. Whenever I hear that I think, "I get it. You hate your family and have nowhere else to go." And I remember reading an interview where a tech CEO was describing his workaholic lifestyle. He said that his son drew a family tree and depicted him as a laptop. I couldn't tell if he was proud or ashamed of it. But I instantly knew I had to put it in a video. It wound up in an episode called "The Office Experience"  at 1:36.

Was there a specific viral internet video that made the light bulb go on for Vooza?

Before Vooza existed, I made this video with a friend of mine (a funny comedian named Jared Logan) about the "Haters Gonna Hate" guy.

I noticed that got more attention than other videos I had made and thought the silly stuff in the tech/startup world might be a good area to target in the future.

Then we started doing Vooza. Two videos really put us on the map. One was the Radimparency video, which was influenced by the talking head Apple product videos that are so over-the-top. 


And our animated explainer video, which was a takeoff on the hands-moving-stuff-around style of explainer videos that was really popular at the time. But mostly, I think self-serious tech company videos that are lightly viewed give us more inspiration than the stuff that spreads far and wide.


What is the creative process like working with your customers? Are they allowed in the writers' room, or do you pitch them a more well-formed idea?


We talk with clients first and try to find a good angle. Sometimes we'll pitch an idea out of the gate. Other times we'll ask them for ideas – sometimes the best ideas come from inside jokes that are popular at the company or asking, "What is it that competitors do that you guys make fun of around the office?" We'll then script up something and give the client sign-off before shooting. Typically our clients know what we do and trust us to make something good. [Redacted awful client story here.]

What's harder, pitching clients or doing stand-up? 

Standup is harder but also a lot more fun. Pitching clients is annoying but part of the game. I think I'm a pretty good salesman but that's largely because I hate selling. If someone ain't interested, I'll bail fast. Luckily, people now come to us and they already know and like Vooza. That's a way better framework than cold calling. The hard part of pitching is that people like to talk on the phone and I hate talking on the phone because my mouth doesn't have an undo button.


Is it harder for you to play the straight man or the guy who delivers the punch lines?


I like being somewhat straight in the Vooza stuff and letting other people play crazy. I write a lot of the scripts so sometimes it's nice to give someone else a line and see where they can take it. A lot of the funniest stuff on the show is improvised. Much thanks to my funny castmates who elevate a lot of stuff that's crap into hilarity.

Is there something about humor for the tech industry/start up world that makes it more difficult to pull off than a general audience? Or is a narrower audience easier to write for?

I think it's easier with a narrower audience. You know what references they'll get. And I think they really appreciate it when something is written for them. Mainstream shows aren't going to tell jokes about startup acquisitions, coding in Python, or asking The 5 Whys. We go there and I think that's why people in the startup world tune in.


Also, trying to appeal to a general audience is a good way to be boring so I like to avoid that if I can. I dig this Bill Cosby quote a lot: "I don't know the key to success, but the key to failure is trying to please everybody."

Which is your favorite Vooza video, and why?

I'm a fan of "Honest Business Card Exchange" because it's exactly what I think whenever I meet with someone and they want to exchange business cards. When that video became one of our most popular ones, it helped me feel like I wasn't just some crazy wacko and that others felt the same way. Also, I love sending that video to people after we exchange business cards because, hey, I'm part of the problem.

What should people expect from your keynote at FI Live; or, can you give a window into how Vooza relates to other tech startups?

I'm going to give some of the top lessons I've learned from running a fake tech startup. It'll be fun to see who in the crowd takes it seriously – and for how long. 

As for this: "Can you give a window into how Vooza relates to other tech startups?" Well, we're a real startup about a fake startup. Well, actually there is a big difference between us and 99% of other tech startups: We actually make a profit. Radical, eh!?


Contact Ian at, or follow him on Twitter @ianofthefuture.

Reader Comments (1)

Love the idea....Well done!!

April 29, 2014 | Unregistered CommenterArushInfotech

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