Hipmunk

» see hipmunk.com as it lived, on the wayback machine

~ the obit ~

hipmunk launched in august 2010 from san francisco, founded by adam goldstein and steve huffman. huffman was already a name in tech because he had cofounded reddit. that company had sold to conde nast in 2006 and he had recently moved on. hipmunk's hook was a different way to sort flights. instead of cheapest first, the site laid out a horizontal time-bar of every option, color-coded by an 'agony index' that fused price with flight duration and stop count into one score. the idea was that the cheapest flight was usually the most miserable one and that travelers would pay a small premium for less pain. the chipmunk mascot did not hurt.

hipmunk raised about $55 million across multiple rounds and became one of the more visible consumer travel startups of the early 2010s. the agony-index format showed up in tech press writeups regularly. the consumer flight-search market was already brutal at that scale though, with bigger players like kayak and expedia spending more on inventory partnerships than hipmunk could match. by 2015 the company was looking for a strategic exit. sap concur, the corporate-travel-and-expense software giant inside sap, acquired hipmunk in september 2016 for an undisclosed price.

the acquisition logic was that concur could fold a consumer-grade flight-search ux into its corporate-travel-management product. that fold did not really happen. concur kept hipmunk operating as a free standalone consumer site for three more years while not investing in it, and the agony index slowly drifted from clever to outdated as the larger flight-search market consolidated around google. on january 14, 2020 concur announced the shutdown. the site closed on january 23. that same day adam goldstein and steve huffman publicly disclosed they had offered to buy hipmunk back from concur. concur turned them down.

hipmunk was for the kind of traveler who books out of jfk and tries to minimize how miserable a connection is. that was not the routing problem i had. flights out of ankara mostly run through skyscanner or the turkish airlines site, and hipmunk's inventory leaned heavily us-domestic. i knew the brand because steve huffman is the more famous half of the founding pair and reddit kept him in tech press through the whole hipmunk era. when the shutdown news came out in january 2020 i read it as a footnote to the larger story about how consumer flight-search got absorbed into google flights.

~ the rap sheet ~

~ the agony index ~

the agony index was the actual cultural artifact of hipmunk. it was one of the early consumer-product moments where someone shipped a search interface that openly admitted the cheapest result was usually a bad one. you would type in your trip and get a horizontal time-strip of options where each bar's vertical position encoded its agony score. the longer the bar, the longer the flight. the redder the bar, the worse the layovers. the metric itself was tunable. you could tell hipmunk you cared more about price or more about duration and watch the rankings rearrange. that was a small design idea but it rippled. google flights and skyscanner both ended up shipping similar duration-weighted sort orders within a few years of hipmunk launching it.

~ the buy-back attempt ~

the postscript that made hipmunk linger in tech press was the founder buyback. when concur announced the january 23, 2020 shutdown, adam goldstein and steve huffman publicly stated they had offered to buy the company back. concur refused. that detail mattered because it implied concur preferred to shut hipmunk down rather than let the founders revive it. the more cynical reading is that concur did not want a former asset competing in any small way with its enterprise products. the more charitable reading is that the brand and the asset were too entangled with concur infrastructure to cleanly extract. either way the result was the same. the site went off in january. the agony index went with it.

~ the long tail ~

adam goldstein went on to do a phd in machine learning at stanford and to found a string of ai-related ventures. steve huffman returned to reddit as ceo in 2015, three years before the hipmunk shutdown, and is still running it through reddit's 2024 ipo and beyond. hipmunk is the part of huffman's resume that most people forgot about. the agony index lives on as an idea in every flight-search ui that now sorts by something other than raw price. the chipmunk itself is gone.

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