Groupon: Andrew Mason

Andrew Mason launched Groupon, the deal-of-the-day Web site, in November 2008.

Andrew Mason launched Groupon, the deal-of-the-day Web site, in November 2008. Today, the site sends out more than 900 deals every day to 70 million subscribers in 46 countries.

Groupon, which is based in Chicago and has grown to 6,000 employees around the world, has been called the fastest-growing company ever. But Mason isn't your average business tycoon. A cherubic-looking, slightly disheveled 30-year-old, Mason was a music major at Northwestern University. He wanted to be in a band but ended up getting more excited about building Web sites.

A scholarship to the University of Chicago for a master's in public policy led to the idea for a site that would bring people together online to solve problems collectively.

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Result: The Point, launched at the end of 2007. It tapped into the growing popularity of social networks, allowing anyone to start a campaign for money or group action once a "tipping point" of people agreed to participate. If this is starting to sound familiar, here's why: People began to create campaigns to get discounts at local businesses. So Mason started a blog in late 2008 called GetYourGroupon.com, featuring deals in Chicago each day. As long as a certain number of people signed up -- and agreed to pay -- everyone got the deal. Merchants got a boost in traffic in exchange for their promotions, plus a check from Groupon.

The Point wasn't a moneymaker. But two weeks after the blog debuted, says Mason, "it was clear we were on to something." By January 2009, plans were in place to expand to other cities. After launching in Boston in March and New York in May, the company quickly went from adding a city a month to ten cities a month by the end of the year. Deals such as $10 for admission to Washington, D.C.'s Newseum (regularly $22) sold 28,600 coupons.

Why is Groupon successful? The first reason is simple: Who doesn't love a deal? The fast-growing membership and spawning of copycat sites, such as LivingSocial, are proof that the concept has appeal. The second is that Mason helped local businesses solve the problem of attracting new patrons. "We get them in the door, and the merchants take it from there, delivering the services to get them back," he says. And third, because the Groupon model works in any market, it can easily be scaled up. Groupon turned down an offer of $6 billion from Google to buy the company and, before that, $4 billion from Yahoo, and it is widely expected to take its stock public.

Mason doesn't seem comfortable talking about his success, describing it as "overwhelmingly surreal and completely distracting." He jokes about going from "trying to save the world with The Point to hawking coupons."

What's next for Mason? Expanding and fine-tuning Groupon. Last year, the site started to personalize the deals that show up in your in-box, based on where you live and your buying history. In May, the company introduced GrouponNow -- instant deals via a mobile app -- in Chicago. If all goes well, more cities will follow.

Jessica L. Anderson
Associate Editor, Kiplinger's Personal Finance
Anderson has been with Kiplinger since January 2004, when she joined the staff as a reporter. Since then, she's covered the gamut of personal finance issues—from mortgages and credit to spending wisely—and she heads up Kiplinger's annual automotive rankings. She holds a BA in journalism and mass communication from the University of North Carolina at Chapel Hill. She was the 2012 president of the Washington Automotive Press Association and serves on its board of directors. In 2014, she was selected for the North American Car and Truck Of the Year jury. The awards, presented at the Detroit Auto Show, have come to be regarded as the most prestigious of their kind in the U.S. because they involve no commercial tie-ins. The jury is composed of nationally recognized journalists from across the U.S. and Canada, who are selected on the basis of audience reach, experience, expertise, product knowledge, and reputation in the automotive community.