Comedy as a Startup

A bit about me: roughly a year ago I was hired to Create Content for a hip young tech startup in Manhattan. We were located in a small office in a Midtown WeWork, which soon became a bigger office in a Midtown WeWork, which soon became a small office in FiDi, which soon became a bigger office in FiDi (with ping-pong tables!). I was employee #5. Some months in I was tasked with the elucidation of our company mission – a project of Supreme Importance given that we were, as they say, a mission-driven company. I drew up a page I felt was reasonably original in the pantheon of mission statements, with pleasing turns of phrase and parallel structures worthy of the English degree I was supposedly putting to use. It was succinct but not spare, articulate but not flowery. I shared the Google doc with my boss, the COO, and watched as he deleted it wholesale, replacing it in five minutes with a quartet of boldface Core Values that included “Hungry,” which is, you know, an adjective? (“Why not hunger?” “Doesn’t sound right.”) He did this, for context, seated five feet away from me, without a word. I was brutally demoralized and immediately quit six months later.

So it was with great joy and a few droplets of pain that I devoured the web series Vooza in more or less the afternoon I discovered it. Here is the startup world in all its sleek hubris and ridiculous jargon, its mosaic of turtlenecks and button-downs, its insistent self-congratulatory self-congratulation. Created by and featuring Matt Ruby alongside a cast of New York comics, Vooza was something of a head-scratcher when it debuted in June 2012 – two years, mind you, before Silicon Valley hit the airwaves. Neither Wired nor TechCrunch ruled out the possibility it was a legit company with a sense of humor, and it’s difficult to blame them; like Colbert Report-era Stephen Colbert, Vooza masquerades as the very thing it lampoons. That’s standard satire, sure, but as a comedy object it exists in a strange nexus between traditional web sketch and mockumentary web series. Ruby describes Vooza as a “video comic strip,” which seems a resonant formulation – it allows his work to exist in a single world without confining it to any single narrative structure. “Narrative,” he told me, “is not how people watch stuff on the web anymore. It’s unrealistic to expect people to watch things in a narrative format; you need give them the freedom to enter into a world wherever and whenever they want.” The video comic strip, in other words, gives both viewer and creator the freedom to just fuckin’ play around.

We’ve always had this freedom, of course, but it usually comes at a price. One of the greatest and worst moments in improv is when a scene stumbles into a reality so engrossing with characters so fresh that we yearn for it to last beyond the allotted five to thirty minutes before it vanishes forever. Television has great power to build and explore idiosyncratic worlds, but it’s constrained by the demands of narrative. In TV we expect jokes to amount to more than themselves; in sketch, a good laugh often justifies its own existence. And half the pleasure of a sketch is its brevity — TV has far less freedom to apply laser-focus to one aspect of a world that it will never touch again. (Yes, there are exceptions, and I’ll bet most of them are episodic animated series.)

By setting his video comic strip within the bounds of a narrow universe, Ruby has tapped into not only an endless well of material, but an endless well of eminently marketable material. He’s ingeniously carved out an audience that already loves to see its own reflection. Ruby knows this well, as the former Employee #1 at 37signals, now Basecamp, where he helped author some of the best-regarded texts in the industry. “One of my big influences is Dilbert,” he said. “When I was in the startup world, I’d see engineers constantly sharing Dilbert cartoons. It’s not that funny, but everybody loved it. Why? Because it’s about their world – and they’d never seen anybody talk about that before.” He speaks with similar fondness of This Is Spinal Tap: “Dudes in bands are the ones who love it the most, because even though it’s completely ridiculous, it reflects some sort of reality to them.”

Ruby has taken one of tech’s most important dictums and applied it to comedy: always design your product with the user in mind. And it’s worked gangbusters. Vooza’s hundred-plus videos have garnered millions of views, and attention from industry bigwigs like Foursquare’s Dennis Crowley and Tumblr CEO David Karp. The project has evolved from an outlet for funny people into a self-sustaining content platform: lately, Vooza pays the bills (and its actors) by making sponsored content for companies looking to get in on the funny. Customer acquisition, Ruby tells me, is entirely organic – brands come to him, and they often insist that the product placement be as subtle as possible. He also brings in a steady side income touring in character, speaking at tech conferences as Vooza CEO Matt Stillman. And while he wouldn’t give me any precise financials, he assured me the work sustains itself.

We may be witnessing the birth of a bizarre new model for indie comedy: the startup model. “We have this romantic notion that you just have to make good things,” Ruby said, “but these days business is part of the package. You have to make something good, but you also have to figure out how to make people pay attention to it. I’m going to sound like the people I make fun of, but in the tech world we have this notion of the minimum viable product: what’s the smallest thing we can make and put out in the world now, and get real feedback now, so we can iterate on it and make it better? I mean, you could write a TV show and bounce around network meetings for three years, or you could figure out what the version is that you make this weekend with your friends.”

Vooza director Jesse Scaturro, who’s directed everything from national ad campaigns to live comedy shows, agreed that this level of creative control is not to be overlooked. “I’ve worked in commercials where every detail is decided by committee,” he said. “When you’re looking for approval on a shot, ten clients huddle up to decide whether a shoelace is tied properly. Nine times out of ten it ends with a call to the executive’s office. Ultimately, an independent web series is freedom for everyone involved in the filmmaking.”

Ruby and his team, who operate under the production company Fort Pelican, have already shipped a new product with an equally considered product/market fit. It’s called Club Scale and it’s basically Vooza for nightclubs: the first season features Dan Soder and Joe List as two macho doormen at New York’s most happening spot. Ruby expects Club Scale will take an anthology form, with each new season revolving around different characters – DJs, bartenders, owners. This is a solid, generative model that I suspect will become the bread and butter of comedy web series. It’s already proliferated across TV, empowering writers to tell compact, character-driven stories without any worry for where these people will be – and what their contracts will look like – five years down the line. It enables the sort of rich world-building that was previously only accessible in, say, Star Wars extended universe novels; it’s user-friendly, allowing viewers to enter wherever and whenever they please; it saves creators from burnout and audiences from stale storylines. In other words, it lets you milk a thing for what it’s worth and then move on.

Like Vooza, Club Scale is directed by Scaturro with a sleekness befitting of the world it skewers. List and Soder bring a disorienting honesty that speaks to Ruby’s love for Christopher Guest; they’re almost adorable, in fact, once you overlook their characters’ unabashed dickery. This is sort of true of the series as a whole, though: behind the flashing lights and dancing bodies is the distinct feel of just some buddies hanging out. List and Soder (and Ruby, on the other side of the camera) have a chemistry that comes of roughly a decade of friendship, which seems to be a recipe for success. “I’ve been on sets where you get there and you think, ‘Okay, this is going to be a long day of work,’” said Soder, “but Club Scale felt like being in high school, where you’re working on a class project and everyone’s doing their part. It felt like just four friends sitting around.”

I doubt there are very many other business ventures that have that feel – certainly not startups. But in comedy, somehow, you can turn chilling with your buds into an honest living, and a web series is a pretty easy-to-make minimum viable product: the stakes are low, the risk is practically nonexistent, and if you do it right, the payoff can be enormous. You just gotta find the right market.

Seth Simons is a writer in Brooklyn. Follow him @sasimons or email him at

Comedy as a Startup