Hipmunk, Conceived by David Pogue’s Teenage Co-Author, Embarks On Mission to Make Travel Search Easier

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Pogue’s Missing Manual series for O’Reilly. He met Pogue at a book signing when he was 14, and the columnist hooked him up with O’Reilly, which led to an authoring assignment—AppleScript: The Missing Manual—and to some editing work with Pogue. When Goldstein was 16, he and Pogue co-authored Switching to the Mac, a guide to the Mac OS X operating system for reformed Windows users.

Goldstein spent the summer of 2005, between his junior and senior years in high school, working at O’Reilly Media in Sebastopol, CA, where Tim O’Reilly invited him to the company’s exclusive Foo Camp hacker event. It was the same summer that Graham and Livingston were launching Y Combinator—a combination startup school and venture investing operation—and at Foo Camp Goldstein met both Graham and Huffman, who was starting social bookmarking site Reddit as part of the very first class of Y Combinator companies.

During his freshman year at MIT, says Goldstein, “Out of the blue I got an e-mail from Paul Graham, who said ‘Chris Anderson is looking to start a company, you should talk to him.'” Anderson, of course, is the Wired editor whose bestseller The Long Tail appeared in 2006. Anderson wanted to start a company that would help authors find audiences. “As someone who had been an author, I thought that was a good idea,” Goldstein says. So he co-founded BookTour with Anderson, and dived in on the project full time during the summer before his sophomore year of college.

At that time, BookTour was borrowing office space from Reddit, which Condé Nast, Anderson’s employer, had just acquired. It was one of the first dramatic exits for any Y Combinator-backed company. Goldstein ended up not just sharing an office with Reddit, but rooming with Huffman.

Fast-forward to early 2010. Huffman had left Condé Nast in 2009, and Goldstein, who was about to finish his undergraduate work at MIT, had given notice at BookTour, which “hadn’t been getting a huge amount of traction,” in his words. “One day I called up Steve and said ‘I want to work on a startup, what are you doing this summer?'” he says.

Huffman liked Goldstein’s pitch for a business built around a more intelligent travel search interface. In March, the two attended “Demo Day,” the climactic investor-pitch session at the end of Y Combinator’s winter 2009-2010 term, then pitched their own idea to Graham. Graham went for it, and invited Huffman and Goldstein to join the summer 2010 session. That made Huffman a repeat Y Combinator startup founder—not the first, evidently, but one of only a handful, according to Goldstein.

Given Huffman’s success with Reddit, Hipmunk “could have gotten funding anywhere,” says Goldstein. But he says there were strong reasons to work with Y Combinator, despite the fact that the capital startups receive there is relatively expensive. (The average Y Combinator startup gives up 6 or 7 percent of its founding equity in return for a stipend amounting to about $11,000 plus $3,000 per founder.) “Whether we took money from them or not, Paul Graham is a fan of Steve’s and mine, and we knew he would have helped us out either away, and it just seemed wrong to take advantage of that,” Goldstein says. “It was better to get on board with them. And these days there is a great deal of prestige that comes from being in Y Combinator.”

Indeed: “super-angel” Ron Conway, at a recent Y Combinator-sponsored conference on angel investing, called Y Combinator “the MIT, the Harvard, or the Stanford of incubators.” Conway, you may not be surprised to learn, is also an investor in Hipmunk, through his firm SV Angel.

That’s the back story at Hipmunk, surely one of the most highly pedigreed companies ever to emerge from Y Combinator. But what about its future? Goldstein is probably right that there’s room for improvement in the way consumers book flights and make other travel arrangements online. But having profiled Boston-area companies like ITA Software and TripAdvisor, both powerhouses in the travel search arena, I happen to know that the amount of brainpower already focused on this exact problem is spectacular. ITA, in particular, is full of MIT-trained brainiacs who … Next Page »

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Wade Roush is a contributing editor at Xconomy. Follow @wroush

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