LivingSocial Is Next Bet for Steve Case After Zipcar Payoff

America Online co-founder Steve Case, recasting himself as a venture capitalist, pledged to invest $200 million in fast-growing companies in 2005. With his bet on Zipcar Inc., he’s now made that cash back.

After Zipcar’s first day of trading on April 14, the car- sharing company has a market value of $1.12 billion. Case’s Revolution LLC owns about 18 percent of the company, valuing its stake at $199 million. That adds to his earlier gains from Revolution Money, a financial-services business he sold to American Express Co. last year.

Living Social, an online-coupon service taking on market leader Groupon Inc., is the next shot at profit for Case’s fund. Like his other investments, he got in early enough to help transform the ambitious startup into a business with broader consumer appeal.

“It’s the same playbook we ran with AOL -- trying to take a big idea that initially was a little company and make it into a big company,” Case said this week in an interview. “It’s a lot of fun to be partnering with entrepreneurs who have big ideas around consumer businesses that can change the world.”

Case, who helped start AOL in 1985, founded Revolution 20 years later to invest his own money in consumer, health, real estate and hospitality companies. He dedicated $200 million to a unit called Revolution Growth, where he’s made six investments. He has a related entity called Revolution Ventures that invests in less mature companies.
American Express Deal

Revolution Money, which provides credit-card and online money-transfer services, was one of the six startups in the Growth portfolio. Other backers in that company included Goldman Sachs Group Inc., Deutsche Bank AG and U.S. Venture Partners. When it sold to American Express in 2010, the business fetched $300 million.

Case, 52, runs Revolution Growth with former AOL executives Ted Leonsis and Donn Davis. They’re now trying to raise about $400 million from outside investors for a fund, according to two people with knowledge of the plan. The AllThingsDigital blog reported on the effort last month.

In August 2005, four months after opening Washington-based Revolution LLC, Case bought a majority stake in Flexcar, a Zipcar competitor, for an undisclosed price. He made the bet after using the service in Washington to get to meetings around the city. His stock turned into shares of Cambridge, Massachusetts-based Zipcar when that company acquired Flexcar in 2007. Zipcar revenue has taken off since then, jumping to $186.1 million in 2010 from $106 million in 2008.
Zipcar Surges

“We really believed in the idea and believed that, particularly in major cities and college campuses, it was something that would get broad adoption,” Case said.

Zipcar surged 56 percent in its first day of trading on April 14. The stock gave up some of those gains yesterday, dropping 84 cents, or 3 percent, to $27.16 on the Nasdaq Stock Market.

Revolution is the largest Zipcar shareholder, followed by Silicon Valley firms Benchmark Capital and Greylock Partners, according to a regulatory filing. For now, Case’s Zipcar gains are only on paper. He and other insiders must hold onto their shares for six months before they can sell.

In 2008, Case invested in Web startup LivingSocial, led by Tim O’Shaughnessy, another former AOL employee. At the time, the site let users discover and review things such as books, movies and music. After converting into a daily-deal coupon site, it stands to generate $1 billion in revenue this year, according to two people familiar with the company’s finances.
‘Seize the Day’

LivingSocial, like Revolution, is based in Washington, an area where Case has targeted investments. SnagFilms LLC is located there, and Clearspring Technologies Inc. is in nearby McLean, Virginia.

As fast as LivingSocial has grown, it trails Chicago-based Groupon, which is said to be on pace for as much as $4 billion in 2011 sales. The market they’re competing in hardly existed two years ago, and Case has encouraged LivingSocial to pour money into sales and marketing to “seize the day,” O’Shaughnessy said.

“He has the ‘been there, done that’ credentials, particularly in a consumer environment,” O’Shaughnessy, 29, said in an interview. “When you look at a lot of investors out there, they haven’t been at the helm of a ship that has tried to do those things.”

Peter Barris, a Groupon investor at New Enterprise Associates in Chevy Chase, Maryland, north of Washington, says he prefers to partner with Case. Their firms are both investors in Clearspring and SnagFilms.

“He’s a smart guy and I wouldn’t bet against him,” said Barris, who’s known Case for about 20 years. “I see NEA collaborating more than competing with him.”
AOL’s Struggles

While Case is credited with helping build AOL into a Web giant -- valued at more than $150 billion at its peak -- he’s also known for orchestrating the disastrous purchase of Time Warner Inc. for $124 billion in 2001. Case stepped down as chairman of the combined company two years later. AOL was spun out of Time Warner in 2009 and is now valued at $2.1 billion.

Clearspring co-founder Hooman Radfar is more interested in Case’s successes than his failures. Case first invested in Clearspring in 2007, when the startup’s online service for advertisers and publishers reached 100 million monthly unique users. The company now has an audience 10 times that size, and Radfar credits Case with that growth.

“Take that number and that’s Steve,” said Radfar, 30, who started the company in 2004. “He’s willing to take very, very big risks. The key word when you think of Steve is big.”

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