There's an excellent Japanese restaurant in Chicago's Wicker Park neighborhood. The place has been around for years and still draws a crowd, a trendy mix of tattooed hipsters and business-casual professionals. Black-clad waiters with spiky hair shuttle plates of sashimi, which is pricey but worth it, judging from the reviews on Yelp. On weekend nights, customers might be directed to their tables by the most absurdly overqualified maitre d' on earth: Andrew Mason, who is also the chief executive officer and founder of Groupon (GRPN).
"In addition to actually greeting customers as they come in," says Mason, "I'm running between the front of the house, where we have one system, and the back of the house, where we have another system, entering redundant data from one into the other. I'm just managing the mess that is this technology infrastructure for the business."
Mason says his hosting gig, which he agreed to discuss on the condition that the establishment not be named, helps him understand what makes local merchants tick--how they book reservations, accept payments, and manage inventory. It's all the stuff businesses do behind the scenes. It's also, he says, the future of Groupon. Mason co-founded the company in 2008 as a website for selling marked-down spa packages and half-off pizza. Just four years later, it's a 12,500-employee public company that e-mails daily deals--on everything from 43 percent-off Android tablets to discounted beekeeping classes--to 36 million customers in 48 countries. Mason built his empire by persuading retailers and restaurant owners to offer deals, but he's rethinking what a tech company can offer such businesses, and a good way to understand them is to work at one. "I didn't realize how hard it was to run a small business," he says.