Philip Kiracofe and Others Talk About Healthy Failure at Ignite NYC

There’s no shortage of ways that a startup can fail. Money runs out, a rival wins over the customer base, or the company just does not deliver on its expectations. But while failure may wound pride, it also creates room for new ideas to flourish in the innovation scene.

Philip Kiracofe, entrepreneur, investor, and co-founder of the Failure Club, spoke with others at last Wednesday’s Ignite NYC event about the necessity of taking on the unknown, and what can be learned when those efforts crumble.

Ignite NYC, born out of the Seattle-based Ignite event, is a gathering of the city’s techies, artists, and entrepreneurs with a lineup of speakers who share five-minute stories. Last week’s event at The New School in Greenwich Village was all about failure—specifically, “Stories from the Other Side of Failure.”

The topic seems near and dear to Kiracofe’s heart. His Failure Club project shows people how to fail big and fast—on camera with a little help from filmmaker Morgan Spurlock. Participants take on audacious, one-year projects that seem doomed from the start, yet have attainable objectives. “There’s a specific measurable goal that everyone can agree was either achieved or not,” Kiracofe said.

The purpose, he said, is to find inspiration in the fear of failure. In fact, about the same time Failure Club launched, Kiracofe sought to create a $10 million venture capital fund within one year. “I failed because it took me three,” he said.

Horizen Partners, the early stage venture fund he co-founded, eventually did get off the ground and was incorporated into SoftBank China & India Holdings in 2006. These days, Kiracofe keeps busy in a variety of endeavors, such as co-founding marketing agency Travelcology in New York. He previously worked with, which connects people to professional service providers through their social networks. Kiracofe’s latest gambles include establishing a mountain bike race in Haiti.

“The obstacles we allow ourselves to be stopped by—time, money, education, and expertise—are all self-imposed,” he said. “When you wipe those out, anything is possible.”

Though New York is a relative newbie in the innovation scene, the city already has a menagerie of fumbles and foibles to learn from. Braden Kowitz, a design partner at Google Ventures who worked on Gmail, Google Trends, and GoogleDocs, shared with the Ignite NYC audience what he learned from his mistakes. “I put buttons [on the Web], unintentionally, where people can’t find them,” he said.

One of his first tastes of failure came in 2001 when he tried to develop a platform to visualize how people use the Web, learn what pages they visit, and which browser they used. After three months of work, Kowitz revealed a prototype that only muddled the issue. “The Web pages were [represented as] skyscrapers and the traffic between the sites were like airplanes moving through cities,” he said. “If you think you’re confused, so was everyone in the conference room.”

Kowitz attributed his mistake to design blindness, which arises when an idea only makes sense its originator. He said designers, and entrepreneurs for that matter, need to share their ideas with others for critiquing early on to avoid such headaches. “You have to show your work to people before you can get it done,” he said.

Sometimes failure can push an entrepreneur to discover success. Will Mayo, founder of New York’s SpokenLayer, told the Ignite NYC crowd how he found his footing after several misfires. Mayo gave the startup world several tries—first with AUDIOis, a social platform for musicians to rehearse, share and create music, and then with SoundPipe, an app he never shared publicly but was trumped by a rival who landed funding and a strong user base first.

Turning his attention to his challenges with dyslexia, Mayo created SpokenLayer, which reads text from the Web. Even with a fresh idea, he ran into trouble. Mayo burned through his cash while the app was still in the works, was forced to fire all of this developers, but at the same time he landed a spot in this spring’s TechCrunch Disrupt event “with no team, no money, and no product.”

Mayo finished building the app in 17 days, just in time to take the stage.

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