Adioso

2008 - 2020
dead
two australians spent twelve years trying to build a flight search that took a sentence instead of a form. you typed melbourne to europe late september for twenty to thirty days and adioso worked out what that meant, which is still not a thing most booking sites will let you do. tom howard and fenn bailey got it into y combinator's winter 2009 class on that idea and then spent years finding out that airlines do not hand over fares and seat availability in any form complete enough to trust. the site kept running anyway until march 2020. by may the domain had lapsed and the address was answering with an expired dns notice.

~ the eulogy ~

Every flight search built before or since asks you for two airports and two dates, because that is the shape the airline systems want the question in. Adioso started from the observation that this is not how anybody actually decides to travel. People know roughly where, roughly when, and roughly for how long, and the form makes them pretend otherwise.

So the search box took a sentence. Melbourne to Europe late September for 20 to 30 days. Anywhere warm in March under four hundred dollars. It expanded the vague parts into every combination they could cover and gave you back a grid of what those trips actually cost. Tom Howard and Fenn Bailey started building it in Melbourne in 2008 on three hundred and fifty thousand dollars of angel money, and got into Y Combinator's Winter 2009 class on the strength of it.

What followed was twelve years of running into the reason nobody had built it before.

~ the dossier ~

Born2008, in Melbourne
Peak35,000 signed-up users and three booking partners, late 2013
Killed2020
Lifespan12 years
Made byTom Howard and Fenn Bailey, Y Combinator W09
Killed byairline data it could never fully get, then an expired domain

~ the data problem ~

The reason nobody had built it was structural. To answer a question that loose you need every fare and every seat count across hundreds of route combinations at once, and airlines do not distribute that. What they distribute is priced per query, rate limited, frequently stale, and shaped for exactly the origin-destination-dates form Adioso was trying to get rid of. Howard put it plainly years afterward: it is basically impossible to get flight inventory complete and current enough to deliver a service customers can trust.

They found this out in 2009, in public, with money in the bank and nothing working. Howard's account of that period is unusually honest about the investor half of it, that some backers stayed supportive and some turned hostile, and about the pressure to hire salespeople to go and sign airlines when the underlying product was not ready for any airline to sign. They did not take that advice, rebuilt the product instead, and waited for the industry to change shape around them.

~ what it was actually good for ~

It half worked. By November 2013 Adioso had three online travel agencies integrated for booking, more than thirty-five thousand signed-up users, a team twice the size it had been, and a place on The Independent's list of the fifty best travel websites. The site got a solid TechCrunch write-up in August 2010 under a headline about flight search for people keeping their options open, which is still the best description of it anyone wrote.

The flexibility was only usable if flexibility was legal for you. Booking a Schengen visa out of Turkey in those years meant handing an embassy a specific itinerary with specific dates attached, so anywhere in Europe sometime in late September was not a plan you could file. Adioso was built for a passport that could answer its own search box.

~ the day the dns expired ~

The site did not rot. Between 2018 and 2020 somebody moved its eight search backends from http to https, which is not the kind of work anybody does on a product they have abandoned. The archive has adioso.com serving normally on 25 March 2020.

The next capture is 13 May 2020 and it reads Expired DNS Hosting Services. The domain registration had lapsed and nobody renewed it. In between those two dates the entire commercial aviation industry stopped flying, which meant the twelve-year-old problem of not being able to get complete fare data was replaced by there being no fares.

Howard has said since that the company rebranded and pivoted into selling load and fare optimization to airlines, and that he left when that happened. He also dates his own memory of the end to 2013, which the archive flatly contradicts: somebody kept the consumer site running for another seven years. The address answers today with the default nginx welcome page.

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also died in the 2020s: Kongregate, BritBox UK, Anthem

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