LivingSocial.com Founder Tim O'Shaughnessy waited tables at Ruby Tuesday in college—not a typical background in a field whose entrepreneurs often spend their formative years crafting software code.
O'Shaughnessy says he learned much about running a business from serving demanding customers in an overbooked restaurant. "It was like this game to figure out what's the best way to manage nine tables all by yourself," he says in an interview in Washington, where LivingSocial is based.
O'Shaughnessy, 29, has used his unconventional pedigree to transform the startup into the second-biggest provider of digital deals. The four-year-old company has more than 1,500 employees, up from 33 in early 2010, and expects to generate $1 billion in sales this year, double the forecast in January.
LivingSocial must tackle bigger challenges now. The company lags behind Groupon in the U.S. daily-deal market, which BIA/Kelsey predicts will more than quadruple from last year, to $3.9 billion by 2015. Chicago-based Groupon boasts a staff of more than 7,000 and its 2011 sales are projected to surge to a range of $3 billion to $4 billion, people familiar with the matter said in March.
Another pressing need for LivingSocial is to stand out in a field that has lured more than 480 competitors, including Facebook, the No. 1 social network, and Google (GOOG), the top search engine. "If two years ago—or even a year ago—you had said that 'your competitive set could in a very real way include Facebook and Google,' first I probably would have jumped for joy and then I probably have told you that I don't believe you," O'Shaughnessy says in an office above a Fuddruckers in Washington's Chinatown district, one of three in the capital.
LivingSocial, like Groupon, has raised venture funding to add sales employees, who persuade local merchants to offer discounts on such products as meals and weekend getaways. LivingSocial operates in 12 countries and has 29 million users, while Groupon operates in more than 44 countries with a base of more than 50 million people. O'Shaughnessy aims to help his company stand out with hard-to-copy offerings. These include deals tailored for families: vacation packages, which often include a variety of activities for a flat price; and exclusive events such as the recent "Become a Canadian For a Night," which featured broom ball, curling lessons, Canadian beer, and ice dancing to music from artists like Bryan Adams.
A graduate of Georgetown University with degrees in information management and in marketing and operations, O'Shaughnessy sports carefully parted hair and a uniform of khakis and button-up shirts that make him look at home on Capitol Hill. He oversaw product launches at AOL when it was owned by Time Warner (TWX) and led the consumer products team at Revolution Health, which helps users find doctors, check symptoms, and get tips for staying healthy. Such business chops are uncommon among startup founders, who typically specialize in building technology products and setting strategy, but often must lean on a deputy to handle day-to-day operations—the way Facebook Chief Executive Officer Mark Zuckerberg depends on Sheryl Sandberg, or Groupon CEO Andrew Mason until recently relied on Rob Solomon.
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