Fair enough. Per AllthingsD [1], Andrew Mason has sold about 4 million shares, for $27 million. Per the latest S-1 [2], it appears Mason retains about 23.5 million shares, so he's sold about 15% of his earlier stake.

Eric Lefkofksy has sold (through related entities jointly owned with his wife) about 32 million shares, for $382 million. From the latest S-1, it appears he and his LLCs retain about 129 million shares, so he's sold about 20% of his earlier holdings.

Interestingly, Groupon also paid out about $27 million in dividends in 2009.

Mason diversifying away from Groupon makes good sense, without sending much of a negative signal, as his net worth was probably 99%+ in Groupon before the 2009 dividend and then later stock sales. Lefkofsky was already very wealthy (and thus presumably diversified) from other ventures, so his sales are a stronger signal that he thinks other investments are more promising.

[1] http://allthingsd.com/20110602/where-did-groupons-billion-do...

[2] http://www.sec.gov/Archives/edgar/data/1490281/0001047469110...

Ok, so I'm trying to wrap my head around he ultimately gets screwed on this... Are the people/entities who bought $382mil worth of shares potentially screwed now that they see the real valuation? Is there any potential for fraud in this case?

He probably sold to (supposedly) sophisticated investors that thought they'd scam retail investors later on.

>It's important to know what percentage of his total shares he dumped to form an opinion on this.

not in such a case. 382M out of close to 1B round - it is obvious that he dumped _all_ what he could dump. The rest of his holding doesn't matter - it is just paper.

Agreed. It's certainly not unheard of, or even necessarily unsavory, for founders and early-stage investors to take some profit off the table in later financing rounds. Since Groupon received HUGE financing prior to IPO, taking $382mm out might not have amounted to a giant percentage. Then again, it may have. But the percentage is indeed the more interesting figure.

I'm more interested in how many shares the founders wanted to sell.