The Difference Between A Joke And A Billion Dollar Company Isn’t As Big As You’d Think

How Y Combinator seizes upon a “dumb” startup idea that’s working and helps transform its founders’ thinking to create a valuable business.

The Difference Between A Joke And A Billion Dollar Company Isn’t As Big As You’d Think
[Photo: Popperfoto, Getty Images]

Ben Maitland-Lewis and Doug Rogers were desperate. Their Boston-based marketing startup, which sold software for actors and musicians to create DIY press kits, had been muddling along for a few years now. There had been encouraging signs–good feedback, pilot programs, user growth–but not much in the way of actual revenue.


And so, when an acquaintance who was throwing a corporate Christmas party asked Maitland-Lewis if he knew anyone who rented photo booths, Maitland-Lewis nominated himself. The startup CEO didn’t have a photo booth per se–okay, he didn’t have a photo booth at all–but he figured he could cook something up. He had no choice. “We were broke,” says Rogers, by way of explanation. “And they had $1,000 to spend.”

The two entrepreneurs went to Best Buy and bought a Wi-Fi-enabled memory card. Then they bought a case of beer. That evening, they went back to Rogers’s living room and hacked something together. An event photographer would take portraits of the revelers using a digital camera. The photos would then be transmitted, via the memory card, to an Apple laptop in a backpack–they stuck a wad of paper towels between the keyboard and screen to keep it from shutting down–which would upload the photos to Dropbox. A promoter would bring up the photo in the Dropbox app on an iPad and then email it to the revelers. The whole process would take 10 seconds or so.

The name, Pretty Instant, was something of a joke. The clunky prototype required an awkward pause from the time the photo was snapped to when it appeared on the iPad screen. But the domain name was available, and it had a nice ring to it. And so, 72 hours after the initial photo booth query, they showed up to the party with their hacked-together rig. Amazingly, it worked.

“Two minutes into the party, I remember looking at Ben thinking, ‘Did we figure out something awesome?’” Rogers recalls.

Today, Pretty Instant is an event photography company with a network of freelance photographers and a client list that includes Green Mountain Coffee, Boston Children’s Hospital, and General Mills. And several weeks ago, Maitland-Lewis and Rogers–along with their two other cofounders, Chris Cave and Chase McAleese–moved from Boston to California to enter Y Combinator’s Winter 2015 class.

Did we figure out something awesome? This question gets to the heart of the process by which a beer-soaked brainstorm in a Dorchester living room becomes a product. The question is also why Y Combinator, the Silicon Valley startup factory, seemingly specializes in turning dopey ideas into billion-dollar companies.


Startup stories are often told in which the founders stumble into a big idea, but the Y Combinator model is different. At YC, founders are encouraged to find sometimes laughably small ideas that work well–“Make something people want,” the saying goes–and then to build up from there. Airbnb famously launched as a hack that would allow its founders to pay their rent by turning their apartment into an air mattress bed and breakfast. Now it’s a global hospitality brand. Twitch, the online video game television network that was sold to Amazon last year for $1 billion, started as a one-man reality show, Justin.TV. And Teespring, a 2013 Y Combinator graduate that recently raised $35 million from Khosla Ventures and Andreessen Horowitz, started when two Brown College students wanted to print a silly T-shirt to commemorate a bar that was closing on campus.

“It’s an evolution,” explains Walker Williams, Teespring’s CEO, and the guest speaker at last week’s dinner. “At first it was an entrepreneurial thing: I felt the pain myself and built the solution,” he says. “But then, people made the leap between this static web page to ‘Can you make this for me?’” That demand prompted Williams and cofounder Evan Stites-Clayton to turn their crowdfunding campaign into a company that would allow anyone with a silly idea to create and sell a shirt.

They initially pitched the company as “Kickstarter for T-shirts,” but as Teespring has grown–the company sold 7 million shirts last year and to date Teespring has paid out $1 million or more to 20 people–Williams and Stites-Clayton broadened the vision further. Now, Williams says, “Teespring is a platform for entrepreneurs to go from idea to market.” The plan is to add additional printing and shipping services and eventually expand to other product lines. He says that T-shirts are to Teespring what books were to Amazon–an initial market; not the end game. “What I think we’re doing at its core is democratizing commerce,” he says confidently.

Maitland-Lewis and Rogers aspire to follow the path worn by Williams and Stites-Clayton, and Justin.TV’s Emmett Shear, Justin Kan, and Michael Seibel, and Airbnb’s Brian Chesky, Joe Gebbia, and Nate Blecharczyk. Tuesday, the Pretty Instant cofounders presented their work at Prototype Day, during which each YC startup gives a two-minute presentation on its progress. It’s YC’s version of a table read, the first chance startup founders have to test out the pitches they’ll deliver on Demo Day in March. Pretty Instant, as the founders told their colleagues, has come a long way since its first party in 2011–during a three-month period last year, the company hosted 86 parties, up from 16 a month the year before. They’ve scrapped the paper-towel-stuffed laptop for a custom iPad app that loads pictures in one second rather than 10.

For all of PrettyInstant’s progress, its founders also realize they’ve got a long way to go. “We’re thinking much bigger than we ever thought before,” says Rogers. “It’s so energizing,” Maitland-Lewis adds. This journey from the kernel of an idea–a joke, really–to an opportunity, a big vision, and then an even bigger vision is one that Pretty Instant, and the other 113 YC companies in the current batch, are trying to navigate, one user at a time.

Next week: Y Combinator gets the band back together. This is part two of a series.