Makes you wonder why he didn't exit when he had a chance at $6 billion. I doubt groupon will ever see that type of valuation again considering how terrible their coupons have become and how natural competitors in the space like local papers and yelp are beginning to gain traction.
nh posted a video below which states that based on a $25B valuation, Lefkofsky will grab $5.3B, as he owns 22 percent of Groupon. That's a hell of a lot more than he'd have made in the Google deal.
Groupon stock only has to hold its value long enough for his lockout (usually 6 months) to end. It's usually not hard to do that - when things come crashing down, it's usually a few years in the future, not months.
Not really. Unloading 20% of a company without telling anyone is both hard and, I think, illegal (as an exec). This is one of the reasons Bill Gates' stock sales are so consistent is to keep the market from freaking out when he sells stock. (Ohmigod, Bill sold stock! Oh wait, he's done that every month for 10 years... nevermind.)
Lefkofsky might be able to hedge against the decline of the stock, but hedging 20% of a big company (especially because it'd be difficult to build a portfolio which replicated Groupon's situation and risks) is a pretty tall order.
All that said, I tend to agree with your sentiment...
Or considering how Facebook could basically annihilate Groupon in the blink of an eye if it ever decided to get into that business model. Not only are Groupon's financials highly questionable, but its position is practically indefensible and does not contain any real "switching costs" to keep users locked in or loyal.
