Is Groupon’s Largest Shareholder on Shaky Ground?

Many people know Andrew Mason as the public face of Groupon Inc. (NASDAQ:GRPN), but equally important to the company’s success is Eric Lefkofsky.

Lefkofsky is Groupon’s Executive Chairman; he essentially co-runs the company with Mason. The relationship began when the two worked together at a website called, The Point. It was Lefkofsky who prodded Mason into working on a successor project, Groupon, in 2008.

Don’t Miss: Groupon Continues Sketchy Practices into IPO.

Fast forward three years later and Lefkofsky is Groupon’s largest shareholder with a 17 percent stake. After Groupon went public on Nov. 4, this holding was worth $2.86 billion; he sits on the Forbes 400 list of richest people at No. 293.

While Lefkofsky comes to Groupon with a wealth of experience, he doesn’t come without controversy. This year, the Securities and Exchange Commission was sniffing around and had concerns with rules about what companies can say to investors between the time a company files for an IPO and the shares start trading.

The company has faced questions with its accounting practices and its losses.

Additional actions by Lefkofsky that have raised eyebrows include his failed stints at Brandon Apparel Group, and his share sales of Groupon (NASDAQ:GRPN) when it was a private company in 2010.

It’s been said he has a big mouth and he’s supposedly part of the reason why Groupon’s last two Chief Operating Officers had short tenures. The position remains open.

Along with his Groupon responsibilities, he works at Lightbank LLC, a technology fund that has invested in almost two dozen companies; however, he spends most of his time on Groupon.

How long he’ll stay with Groupon remains to be seen. Lefkofsky appears to have the touch for getting companies to go public but he may not be one to stay around in the long term. This is common for technology companies with Google, Inc. (NASDAQ:GOOG) and Facebook hiring similarly experienced personnel as they help young faces running the company grow and in some cases go public.

Lefkofsky has his tentacles in a lot of different Groupon areas and he doesn’t appear to be leaving anytime soon. It will be interesting to see what state Groupon will be in as a company when he does decide to leave.

It may not be good.

Investing Insights: Groupon Analyst Cheat Sheet.