Hipmunk Homecoming: CEO Adam Goldstein Talks Travel Site Usability

Into the lair of beasts strode Adam Goldstein. Armed only with his wits and a mean set of slides, he descended on the Boston area on a warm, early winter day. He was no stranger to the premises. Goldstein had been an MIT undergrad before moving to San Francisco to participate in the Y Combinator startup program with his online travel company, Hipmunk.

Goldstein, the startup’s CEO and co-founder, spoke at Xconomy’s “6×6: Six Cities, Six Big Tech Ideas” conference earlier this month, representing the Bay Area. I say he was among beasts because Boston is the land of heavyweight travel firms such as ITA Software (now part of Google), Kayak, and TripAdvisor, and upstarts like Hopper, WaySavvy, and SilverRail (now based mostly in the U.K.). And Goldstein has been on record saying other travel sites “have really dropped the ball on flight search.” (On the other hand, Hipmunk formed a licensing partnership with ITA about a year ago.)

Indeed, the whole culture of Hipmunk is about coming “into an established industry with a focus on usability,” says Goldstein, in a polite-but-firm jab at the big players who don’t seem to care as much about being user-friendly. (As for the company’s name, let’s just say the cute-animal logo is its main justification.)

I must confess, I was skeptical at first. Since part of me still lives in the ’90s (the early to mid-‘90s, mind you), any bluster from new travel sites tends to fall on numb ears. Most travel sites seem pretty much the same, and even the worst ones are still more convenient than what people like me used to do, which is call up travel agents and individual airlines, get some options, and repeat until settling on a purchase. Hipmunk is about making the whole search process simpler, more intuitive, and more visually interactive.

But there’s only so far that can take you as a business, as my colleague Wade probed a few months ago. What stood out to me most about Hipmunk is its strategy of building a business by focusing first on getting lots of loyal customers—not trying to cash in on every eyeball.

“The entire world, especially in the world of travel, has become sort of addicted to the idea of making as much money as possible from each time someone visits their website,” Goldstein said. “What that’s led them to do over time is bombard their customers with advertisements and pop-up windows and all sorts of other things that just distract them.” Conclusion: Hipmunk won’t make money from ads, just referral fees when people book trips. But it does need to gain users—lots of users.

Here’s a short video interview with Goldstein, conducted by my colleague Lilly O’Flaherty. I like the part at the end where he references a talk by Northrop Grumman’s Bill Walker, also at 6×6, on high-altitude UAVs (unmanned aerial vehicles). Heck, maybe someday an entrepreneur will pitch an idea for a company that’s a “Hipmunk for UAVs.”

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