Failure as a Badge of Honor

By Kevin Woo One + | February 8, 2011

Thousands of would be actors traveled to Hollywood in the early 20th century seeking fame and fortune in the movie industry. They dreamed of becoming rich, famous and adored by fans around the world. A few became so recognizable they could be identified by first name alone. But for every Cary, Lucy or Marilyn there were hundreds who didn’t realize their dreams.

Today, Silicon Valley is the new Hollywood. Wanna-be tech entrepreneurs migrate from around the world to the Valley with ideas that they hope will change the way people live and earn them millions (or perhaps billions) in the process. Some succeed and earn rock-star status—Steve Jobs and Mark Zuckerberg, for example—but more than 90 percent are destined to fail.

Cass Phillips was among the 90 percent. In 2009, the San Francisco startup event producer and two colleagues started Trogger, a company that aggregated social media topics so people could access information in one place rather can skipping from site to site.

You’re not alone if you’ve never heard of Trogger. The company failed within six months.

“It is not entirely clear, even now, what Trogger did, which is essentially why it failed,” Phillips said. “We couldn’t find a strong market case for it or a clear ‘user’ or problem it solved.”

Such a public admission of failure might seem antithetical to most. But as Phillips says, failure is a badge of honor in Silicon Valley. If you haven’t failed you haven’t tried.

After Trogger closed its doors, Phillips had an idea—what if she organized a conference where the focus was on failure? She theorized that topics such as “Successful startups fail better than others” and “Gadgets gone wrong” would draw a crowd.

Some thought she was crazy. It turns out she was right.

This past October, more than 450 entrepreneurs and investors packed San Francisco’s Hotel Kabuki for FailCon 2010, a half-day conference where entrepreneurs talked about their failed businesses. The attendees shared what they did wrong, what they learned along the way and what they would tell others to never do. Phillips says FailCon was exactly what the local startup community needed.

The conference was promoted entirely by word of mouth and social media. Phillips opened a Twitter handle and hashtag, a Facebook group, a website and a ticketing page. She sent out bi-weekly e-mail blasts to 5,000 Bay Area founders and investors promoting the conference. Phillips also worked her vast network of contacts that helped promote the event on websites such as StartupDigest, Women 2.0, Girls in Tech, Women in Technology, Founders Institute, Founders Card, Founders Space and pariSoma Loft.

To attract attendees, she enlisted the participation of two high-profile venture capitalists, Esther Dyson and Cindy Padnos; New York Times technology reporter David Pogue; Jay Adelson, the former CEO of DIGG; and she shared her own experiences with failure.

As word started to spread, FailCon had its detractors. Phillips admitted to receiving hate mail from those who felt she was embracing failure and that it would reflect poorly on the IT industry. “I had never before hosted a conference that had such a passionate response, both positive and negative,” Phillips said. “As the old phrase goes—if you aren’t pissing off some people, you aren’t taking a strong enough stand. Receiving hate mail, to me, meant I was getting attention, making people talk and arousing passions. I also received letters of support, so I knew it was a solid idea.”

Michelle Randall attended the conference online and said FailCon fell short of expectations. The Bay Area executive coach was at first energized by the idea of FailCon, but the online component of the conference failed because the interaction among virtual attendees was non-existent and felt like an afterthought.

“They had a great concept and under delivered,” Randall said. “Considering the virtual event was free, I got my money’s worth.” Randall added that FailCon is responsible for the stewardship of the community it has created, and that it’s important to continue the post-event conversation and exchange among attendees.

“For whatever reason this didn’t happen, which is a huge opportunity lost for the organizers and the attendees,” Randall said, while adding that her viewpoint might be biased because she attended the event virtually.

Phillips says it takes a village to build a community, and the success of post conference mixers, message boards and on-going dialog depends almost entirely on the willingness of the attendees to engage. “I’m always a little frustrated when attendees say this,” Philips said. “I have tried message boards, and there is Facebook and Twitter. The problem is that I can’t force attendees to engage in any of these; I can only present the tools. Building a community cannot be the organizer’s job alone—attendees have to actively engage as well. It is a problem I feel many events have—engaging with attendees after the event itself—that attendees love to complain about but present few solutions to solve.”

Heeding the input from attendees, Phillips plans to host on-going panel discussions (FailChats), Faceboard conversations and Meetup groups as part of the 2011 community building and marketing plan.

Later this year, Phillips will take FailCon to New York and Paris. Key to her success will be her ability to get to know the local community, its unique business issues, the local culture and the challenges that potential attendees face and then tailor the agenda accordingly.

Dr. Nancy Newman, a professor at the Chicago School of Professional Psychology, says that how FailCon is positioned in each city will be the difference between holding a successful or unsuccessful conference. “I couldn’t imagine if you said (to potential attendees), ‘We’re having a conference for those who have failed’ that people would say, ‘Oh that’s me, I’ll go,’” Newman said. “Our culture has been such that failure is a matter of shame that no one would want to admit it. In the last decade, things have changed and people say, ‘I did fail, but that doesn’t mean I’m awful or incompetent.”

Phillips is aware that a conference designed for a 20-something Silicon Valley entrepreneur who wears a t-shirt and blue jeans is vastly different from one that targets the Burberry crowd. “I actually feel Silicon Valley is not the place for it,” Phillips said. “We already embrace failure here, that’s why we’re the center of the entrepreneur movement. It’s a bit like preaching to the choir. The show needs to travel in order to make a difference.” One+