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

This is the fourth in a series of profiles of companies emerging this summer from Mountain View, CA-based startup incubator Y Combinator.

If anyone was ever predestined to be the co-founder of a Y Combinator-backed Web startup, it’s Adam Goldstein.

He’s got the academic pedigree, having gotten his bachelor’s degree from MIT in electrical engineering and computer science this spring. And he’s got the connections. He has known Y Combinator founders Paul Graham and Jessica Livingston since he was 16 years old. He’s a friend of O’Reilly Media founder Tim O’Reilly and is the author of two O’Reilly books, one co-authored with New York Times tech columnist David Pogue. And he’s got some entrepreneurial experience. Together with Wired editor Chris Anderson, he co-founded BookTour, a site that assists authors with book promotions. Goldstein has even got some of his own seed capital. He tells me that he’s been saving money since he was 16 so that “were I ever to decide to start a company on my own, I could afford to not draw a salary for several years.”

Well, hopefully it won’t be several years before the 22-year-old Goldstein can start drawing a salary at Hipmunk, the Y Combinator-backed company that he launched yesterday together with Reddit co-founder Steve Huffman. The company is attacking the user-interface side of online travel planning, attempting to bring some rationality and convenience to notoriously vexing tasks like booking flights and finding hotels and rental cars.

Currently, Hipmunk’s website focuses on flight searches. The user starts out in the usual way, by specifying origin and destination cities and dates for an upcoming plane trip. But rather than spitting back page after page of results in no discernible order, the way many flight search engines do, Hipmunk will filter out the bad options and sort the remainder on an intuitive “agony” scale that takes into account price, duration, and number of stops. “We’re going to sort the results sensibly, filter out the flights that you’d be crazy to take, and present things in such a way that it’s clear what the tradeoffs are,” says Goldstein.

Hipmunk flight search resultsThat’s a vision Goldstein says he has been incubating for more than a year, since his days as travel planner for the MIT debate team. “I had spent the past four years booking travel for the team and it’s incredibly painful,” he says. “I spent hours looking through Kayak and Orbitz and Expedia trying to find the right flight. It doesn’t have to be that way, but their interfaces really aren’t made for anything else. It’s just a huge database dump.”

Goldstein wants Hipmunk to become known as the intelligent travel search engine—the one that knows that if there’s a non-stop flight from San Francisco to New York that costs just $1 more than the one-stop flight, it probably shouldn’t be buried on page 5 of the search results.

“I think other companies have really dropped the ball on flight search,” Goldstein summarizes. “When Kayak came out, a lot of smart people thought it was the greatest thing to happen to flight search in years, and I think they were right. But looking back at it, I feel like the fundamental experience for most users didn’t change very much. You still have to short through the redundancies, the code-share flights, and all that stuff. People will use a better search engine, if it exists.”

That’s the basic story behind Hipmunk, which unveiled the flight search engine to the public on Tuesday and is now collecting user feedback about bugs and requests for added features. I’ll get back to that technology in a moment. But to me, there are two very interesting threads to the company’s story: first, Goldstein’s path to Y Combinator, where he and Huffman are part of a group of 36 companies that will soon complete the startup incubator’s summer term; and second, the challenges Hipmunk faces as a newcomer in the travel search business, a crowded field with some well-established competitors.

I met up with Goldstein at a SoMa coffeehouse yesterday, and if I repeat a bit of the life story he shared with me, you’ll understand why I say he was predestined to be a startup founder. A programmer from his early teen years, Goldstein was an admirer of … Next Page »

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Wade Roush is a freelance science and technology journalist and the producer and host of the podcast Soonish. Follow @soonishpodcast

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

  1. I’d like to comment on the general concept that it’s best to get out to customers, get feedback, and iterate as quickly as possible. There are a lot of good things to be said about that approach, and they’be been said in many places, so I won’t repeat them here.

    There’s the drawback that Wade mentions. But also: “You only get one chance to make a first impression.” If someone comes and sees your newly released “0.2.1 beta”, which has fewer features and more bugs than you would like, it’s possible that she will say “This site is no good”, and never come back, even when you’ve fixed the problems.

    It seems to me that to make the “get out there early and iterate” strategy work, it’s a lot safer to get out there early with only a small number of users, chosen to be friendly enough to not bad-mouth you, but honest enough to give you uncensored feedback. During this period, you should not publicize yourself. For example, you should tell Xconomy that you’re not ready yet. You should avoid buzz and hype. Save that up for when the product is “ready for prime time”, i.e. ready for lots of users who you did not hand-pick.

    This is entirely my personal opinion about the strategy in general, not about Hipmunk in particular. It has nothing to do with (full disclosure) my being an ITA Software employee nor an Xcomomy investor.

  2. Love it. A true “why hasn’t anyone done this?” moment for me. If they can expand the range of providers to be competitive with Kayak and Skyscanner I’d make this my first and only stop.

    Speaking of travel visualizations… a shameless plug for my own “Hotels.com hotels on Google Maps” site: http://www.roomatlas.com. Live prices in the markers, Street View and Wikipedia placemarks.

  3. Hipmunk’s interface has improved considerably after this post.
    I created a little video showing this new and improved interface and also explaining what Hipmunk is all about.
    The video is here -> http://youtube.com/watch?v=6teBPUgz4Y8
    Regards, Miguel.