Travel Search Gets Convenient With Hipmunk

On the cusp of Kayak's IPO, Hipmunk, the next disrupter of the domestic travel market, is taxiing and poised for flight.

When the airline-versus-online-travel-agent war erupted a few months ago, most experts wanted to talk about casualties in the $255 billion U.S. travel market. But the fallout also created opportunities for sites like Hipmunk, a new flight meta-search website that has wowed the tech community while, ahem, flying mostly under the radar.

Hipmunk launched in August. Since then, the online-booking business has gone haywire: American Airlines yanked its ticket inventory from Orbitz; Expedia dropped American; Delta severed ties with several smaller online agents. If the trend continues, meta-search sites, which scour Orbitz and Expedia but also cut out middleman fees by sending customers directly to the airlines, stand to benefit. And Hipmunk, with its clean interface and customer-first approach, is primed to zoom past all of them.

"Our goal is to build the best travel site on the Internet," Hipmunk cofounder Adam Goldstein says. "And by 'best,' I mean the site that helps people find what they're looking for with a minimum of agony."

Agony -- or the absence of it -- is a key concept at Hipmunk. In fact, it's the principal basis upon which Hipmunk sorts its search results. The site scans data from airlines and online travel agents. An agony algorithm then ranks flights by a combination of price, duration, and number of stops, and lets travelers know which flights are worth their while. In this hierarchy, the cheapest flight might not be the highest-ranked result. But the best one will be. After all, most people would gladly pay an extra $20 to avoid the pain of, say, an eight-hour layover in Rochester.

Compared to a site like Kayak -- which was designed to simplify searches but can still generate more than 50 pages of results -- Hipmunk is minimalist, fitting all its results on one easy-to-navigate page. For Goldstein and his business partner, Steve Huffman, a founder of Reddit, the idea is to streamline the process and save time and money for the person planning a trip at home.

Consider the bottom-left corner of Orbitz, where a check box lets users indicate their preference for nonstop flights. "Why does this check box even exist?" Goldstein says. "If they're going to put this box there," he continues, "why isn't it checked by default?" Try arguing with that logic. (Actually, don't. Goldstein is the 2010 North American debating champ.)

Hipmunk also separates itself from other sites in a surprising way: It hides results of "flights that no intelligent person would take," Goldstein says. A six-hour Delta trip that costs the same as a five-hour Delta trip on the same route gets hidden. (Users can opt to see the hidden results.) This curated approach lets Hipmunk eliminate clutter and display flights in an elegant Gantt chart of cascading times and colors. Toggling from Expedia to Hipmunk is like going from a mosh pit to a symphony hall.

Customers have responded. Within four months of launch, Hipmunk was already facilitating millions of dollars of successful flight bookings, according to Goldstein. The company earns commissions from referrals. Investors have jumped on board too. A $1 million angel round attracted big names such as tech heavy Ron Conway, Gmail creator Paul Buchheit, and actor Ashton Kutcher. Prepare for takeoff.

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