Two years after his ouster as Groupon's CEO, Andrew Mason is embarking on a new entrepreneurial journey selling unconventional audio tours of major cities on a new iPhone app called Detour.
The initial selection of seven different San Francisco expeditions released Tuesday meander from the city's beatnik bars to the weathered docks of the bay while regaling listeners with colorful tales about local lore. Each excursion costs $5.
If Detour follows the course being charted by Mason, the audio tours will span the world within the next five years and the app will become a standard accessory for vacationers or city dwellers just looking for a fun way to learn more about where they live.
"Most of the audio tours that exist today are about what's popular inside museums," Mason says. "So what we are trying to do is turn the world into a museum."
Mason, 34, became rich by trying to create the world's biggest bargain bin. In 2008, he transformed an online service devoted to social causes into Groupon, which offered steep discounts on everything from restaurant meals to hot-air balloon flights if enough people bought them.
By late 2011, Groupon had become an Internet sensation valued at $13 billion in an initial public offering of stock that turned Mason into a billionaire.
Things unraveled quickly as Groupon battled copycat services from hundreds of rivals, including Google and Amazon.com, and the thrill of the deals faded with many consumers. By early 2013, Groupon's stock had plunged nearly 80 percent below its IPO price of $20, triggering Mason's firing. The collapse shrunk the value of Mason's stake in Groupon from $1.5 billion to about $228 million.
Mason, a former punk band keyboardist known for his flippant humor, initially spent his time making a quirky album called "Hardly Workin'" after his ouster from Groupon.
After that diversion, Mason moved from his longtime home in Chicago to San Francisco to focus on Detour - an idea that he had pondered even before he launched Groupon. He recalls becoming frustrated when he and his future wife were vacationing in Rome in 2007 and that could only find mundane audio tours that shackled listeners to a group of fellow travelers.
Mason figured a company would eventually make a more versatile mobile app for audio tours, but he couldn't find one each time he went on vacation. So he decided to try to do it himself, especially once he realized he couldn't think of anything else better to do after his whirlwind success at Groupon.
"My mind got corrupted, so I basically had to work through all the old ideas I had before I became successful," Mason says after arriving to an interview on his Vespa scooter. He is drawing upon his own personal wealth to finance Detour, which so far has just 10 employees in addition to freelance writers who help script for the audio tours.
Detour won't be as easy to copy as Groupon, Mason hopes, because of the technology powering it and the creative stories woven into in it.
When it's open, Detour tracks a listener's location to allow the tours to be taken as quickly or as slowly as desired. The flexibility means the app can automatically adjust for pit stops in restaurants and bars or other distractions. This feature threatens to raise privacy worries, but Mason says Detour only tracks user's locations to steer them through their journeys.
Detour also uses Bluetooth signals to connect multiple people on different phones to they can simultaneously listen to audio tours that look beyond famous San Francisco landmarks.
One tour consists of a 90-minute jaunt through the old haunts of Jack Kerouac and other iconoclastic writers who catapulted San Francisco to the forefront of the Beat Generation during the 1950s. Another 75-minute stroll traipses through San Francisco's grittier sections accompanied by the narration of Grateful Dead lyricist John Perry Barlow.
Mason's to-do list includes expanding his new app's itinerary to include New York, Chicago, Los Angeles, Austin, Texas, as well as London and Paris.
He also jokes that he may make another musical detour by making a Christmas album this year. "I feel like I need to gift the world with my take on 'Jingle Bells,'" he says.