Microsoft Founder and Chairman Bill Gates sold 10 million Microsoft shares earlier this month, for a total of 90 million shares sold over the past year (a value of approximately $2.5 billion). CEO Steve Ballmer also sold nearly 50 million shares in the past week, his first stock selloff in seven years. Gates is still Microsoft's largest shareholder, with nearly 600 million shares. But should other investors be nervous about the accelerated rate of his divestiture? 

Yes, Gates is jumping ship: The Microsoft founder "knows an increasingly bad investment when he sees it," says Chris Nerney in ITworld. Microsoft's stock has languished for the past decade, and the company is now a "hapless also-ran in a number of crucial, emerging markets." Why? Ballmer. How is he even still CEO? "Does [Ballmer] possess compromising photos" he's been using for blackmail?
"Gates casts vote of confidence in Ballmer by selling 90 million shares..."

Let's not rush to conclusions: Sure, Gates could be "souring on Microsoft," says Amy Lee in The Huffington Post. Or he could be "doing as all investors do and diversifying his portfolio." Let's also not forget that he has a massive charity to fund, and selling off stock to benefit his Gates Foundation "is not a new habit... Similar sales garnered attention back in 2010 and 2009."
"Bill Gates sells off 90 million of his Microsoft shares"

Microsoft is at a crossroads: Ballmer is the company's second-largest shareholder, and he's undoubtedly tired of seeing "his own stock options languish," too, says Paul McDougall in InformationWeek. And by all indications, he's on the cusp of a major management shakeup. If Ballmer makes some good, tough leadership changes, Microsoft might yet "warrant another look from even the most discerning investors — including Bill Gates."
"Bill Gates dumping Microsoft shares by the millions"