twice that of Instructables’, according to Compete.com, and both sites are far outstripped by WikiAnswers and eHow, Demand Media’s how-to juggernaut. But it’s true that wikiHow appeals to a broader audience than Instructables. And its articles are certainly more thorough, and more human, than those at content farm eHow—which, interestingly, Herrick used to own.
And therein lies a story. But before I get to that, I want to rewind all the way to 1991, when Herrick was finishing his B.A. in history at Stanford. He told me the whole tale during a long interview on the front porch of the “WikiHaus” on Emerson Street in Palo Alto, a couple blocks north of University Avenue.
Herrick went straight out of school into a management consulting position. “I didn’t like it and I was really bad at it,” he says. Luckily, at age 23, he discovered rock climbing. “It was one of those random days that changes your life,” he says. He quit his job, emptied out his savings account, squeezed all his possessions into the back of a pickup truck, and moved to Yosemite Valley.
It wasn’t a reckless, Into the Wild-style adventure, but it did shape Herrick as a future entrepreneur. “I was not a good athlete,” he says. “I was kind of a klutz. Also, I was afraid of heights. It was a bad combination. But climbing is one of those sports that rewards effort. It’s also a very cerebral activity—the most important muscle you use is your brain.”
Herrick became so absorbed in the sport that he ended up living out of the pickup for two and a half years. “I climbed Half Dome and El Capitan and ended up trailing all around the Western U.S. and Thailand and Nepal,” he says. “Through that process, I really learned a lot more than I’d been learning in my job. For one thing, you always partner with at least one person when you go after a summit, so I learned how to pick people and recognize talent and determination and shared values. I also learned about what you have to do to accomplish a goal. Climbing is 99 percent misery—it’s a lot of frustration and fear. It’s dehydration in the summer and freezing your ass off in the winter. It’s a lot like entrepreneurship.” In fact, it was during his rock-climbing phase that Herrick would meet the co-founders of two of his four future startups.
And there was one more aspect to this life that would stick with Herrick. To stretch out his savings, he tried to make do on $10 a day, with the exception of travel expenses and books, which he considered off-budget. Herrick marked off an area in the pickup that he called his “knowledge box,” and filled it with a rotating collection of new and used hardcovers and books borrowed from public libraries from California and Utah and Wyoming. “I had spent years at Stanford doing academic learning but for the first time, with my knowledge box, I was learning cooking and rock climbing and doing all of these things,” he says. “That started my interest in lifelong learning.”
Eventually, Herrick put his pitons away and went to business school, at Dartmouth. He went back into management consulting for just long enough to confirm that it wasn’t his scene. By then it was 1999, a good time to start something new, and with Dan Frank, one of his climbing friends from Yosemite, he started an online restaurant supply company called Big Tray. More or less overnight, the company won $10 million in venture funding and acquired 40 employees. “It was the sort of thing that only happened in 1999,” Herrick says. “It was a good story and a bad story. Let’s just say it was the best executive education that $10 million could ever buy.” When the dot-com crash hit in 2001, the company ran out of capital and ended up selling for pennies on the dollar. (Herrick maintains that “if the investors had put a little more cash into it, it would have been a good deal for them. Not the next Amazon, but the next Zappos.”)
Herrick took a year after the sale to do the “decompress, dot-com-bust, travel around the world, climbing-surfing thing” with his girlfriend, who is now his wife. Next came Luminescent Technologies, a UCLA-born semiconductor company. While he was there, he reconnected with another old climbing buddy—Josh Hannah, who was working at the time on sports betting sites Flutter.com and Betfair.com.
For entertainment, Hannah and Herrick “started goofing off with some ideas,” Herrick says. “In the process, we started
