SP,
You are kidding right? When should he sell his shares? To keep shareholders happy should he just sit on them forever? Come on now, anyone with half a brain knows that if an insider is going to sell his shares he should sell them into a rally. That is best for all concerned. And the stats clearly show that insiders sell shares when the stock is near a high and buy them when a stock is near a low. Irrefutable evidence that insiders almost invariably take the opportunity to sell shares when it is near a high. After all, would you find it better for him to sell after the stock tanks?
Unless you think all insiders have a duty to hold onto their shares forever, you must be kidding with this line of thinking. And his financial advisor would say the same exact thing as me. Whenever you have a high-level job at a company and you own a significant level of shares, you are undiversified. The ideal level of shareholding is either 50.1% of the voting shares, or it is 5% or whatever the locally required level of "key shareholder" status is. Anything else is inefficient and risky. Now if the guy is Bill Gates and has no other place to park his billions, you have a case there that holding shares isn't the worst thing he could do. Short of that sort of situation the only reason to hold 20% of a company's shares is because you are either making a move in taking them over, or you are just an investor with a whole lot of money and you find it to be a stellar investment in a diversified portfolio.
And if you are still laughing, go back and relearn the basics of portfolio management and risk management...