Groupon’s “Sellout” CEO Files for $750 Million IPO

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In 2006, Andrew Mason was coaxed out of graduate school at the University of Chicago with an offer of $1 million in funding to convert his idea called The Point, which was designed to network people into social action, into a business.  It went nowhere fast, says Eric Lefkofsky, the entrepreneur who provided the seed  money. “People thought the business was just not going to succeed: so I started putting a lot of pressure on Andrew to try and figure out how to redirect the model to make money.”

The redirection seems to have worked. Groupon has more than 7,000 employees and 83 million subscribers in search of networked coupons for everything from restaurant meals to samba lessons, and a quirky ceo whose wicked sense of humor can’t be squelched, even in a stuffy Form S-1— the SEC registration statement for Groupon’s $750 million initial public offering. “After selling out on our original mission of saving the world to start hawking coupons,” Mason writes, “in order to live with ourselves, we vowed to make Groupon a service that people love using.”

How much love? Sales increased from $3.3 million in the second quarter of 2009 to $644.7 million in the first quarter of 2011, according to the filing. Groupon is in the red because “in the past, we’ve made investments in growth that turned a healthy forecasted quarterly profit into a sizable loss,”  Mason writes. In other words, the company has been buying growth and consolidating its position around the world. This is a game of “winner take most,” so staking out turf matters.

It’s quite an astonishing record for a startup, which should make for an equally astonishing IPO. Another social network darling, LinkedIn, launched an overheated IPO earlier this year that sent its stock price up nearly 100% the opening morning. LinkedIn’s market capitalization has settled back to about $7.43 billion. Last year it had revenue of $243 million. On that rough basis Groupon is worth well north of $10 billion, although speculation has pegged its value closer to $20 billion. The IPO will be a rich reward to Mason, as well as co-founders Lefkofsky and Brad Keywell, the University of Michigan buddies whose Lightbank private investment firm still owns a big chunk of Groupon. Their $1 million investment is worth billions. “It’s been almost unimaginable,” Lefkofsky told me late last year. “It hasn’t been like anything we’ve seen. And we’ve been involved with high growth tech companies.” Groupon famously turned down an offer of $6 billion from Google, a decision some thought was crazy. But Mason was going to get rich anyway, and he’s serious about seeing his quirky vision unfold across the world. Note to potential shareholders: do not expect Andrew Mason to conduct business as usual. As he said in the filing, “Life is too short to be a boring company.”