SAN FRANCISCO — Two years ago, Andrew Mason faced an unexpected detour when he was ousted as CEO from the online discount site he founded, Groupon. Now the tech executive's back on the entrepreneurial path, with an iPhone app selling unconventional audio tours of major cities. It's called — you guessed it — Detour.
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 Mason's charting, the audio tours will span the globe 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. "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 Inc., 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 Inc. and Amazon.com, and the thrill of the deal faded for 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.
Without sounding bitter, Mason looks back on Groupon as a "stupid, boring idea that just happened to resonate." He no longer dwells on what went wrong at the company. "I Google it from time to time, but I have moved on," Mason says.
Mason, a former punk band keyboardist known for his flippant humor, initially spent his time after Groupon making a quirky album called "Hardly Workin.'" He then moved from his longtime home in Chicago to San Francisco to focus on Detour — an idea that he had pondered even before launching Groupon. He recalls becoming frustrated when he and his future wife vacationed in Rome in 2007 and could only find mundane audio tours that shackled listeners to a group of fellow travelers.
Mason figured some 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 the audio tours.
Apple's app store already is stocked with audio tours and guidebooks for cities around the world, but most of those focus on familiar landmarks. Detour points out some of San Francisco's top tourist destinations, but Mason is trying to highlight "hidden stories" about the city's past.
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.
Detour won't be as easy to copy as Groupon, Mason hopes, because of the technology powering it and the creative stories woven into it. Detour also uses Bluetooth signals to connect multiple people on different phones so friends or family can listen together.
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. Mason says Detour only tracks users' locations to steer them through their journeys.
His to-do list includes expanding the 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 explore 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.