Andrew MasonPhotograph by Aaron Wojack for Bloomberg BusinessweekAndrew Mason is walking with a reporter amid the seagulls on San Francisco’s Fisherman’s Wharf, using his iPhone to play an audio walking tour. As he approaches the giant hoists with which local anglers move their daily catch to shore, the voice of a local fisherman named Candy pipes up on the recording to describe the scene ahead: “If you see any boats unloading, look for sea lions hanging nearby, waiting for the fish receivers to throw them scraps.” The recording is one of the offerings from Mason’s latest startup, Detour, which he is trying to build into a central repository for a new kind of GPS-based neighborhood walking tour. The guided-tour industry brings in tens of billions a year, so it may actually be a big deal—if it works. “People have an enormous hunger to have really compelling experiences in their cities,” Mason says. Then a seagull poops on his head.
For anyone looking to describe Mason’s last few years, the moment offers an irresistible opportunity for metaphor. The 34-year-old founded and served as chief executive officer of Groupon, the daily-deals site that came out of nowhere in late 2008 and quickly made a name for itself during some of the grimmest days of the recession. Things at Groupon turned sour soon after the company’s blockbuster initial public offering in 2011, and the board fired Mason in February 2013 amid a string of quarterly losses and a cratering share price. Detour isn’t necessarily a bid for redemption; Mason left Groupon worth more than $400 million and doesn’t need to care what anyone thinks of him. Yet it’s likely to be one of the most-watched comeback attempts in recent Silicon Valley history.
