If I were a Microsoft stockholder, I would be so pissed that the company is spending millions of dollars running ads trying to "change its image".

The ad is stupid.  There is nothing to back up the assertion that they are cool.  In fact, Bill Gates buying discount shoes at a mall and eating a churro is anything but cool.

Anyone with half a brain sees right through the ads and then says... how about you take a few of those millions and build an operating system that is actually an upgrade from XP (unlike the downgrade that Vista currently is). 

Unless... maybe the whole point of the ads is for us to all start talking about how much the ads suck, rather than how much Vista sucks?  Perhaps Bill Gates is still a genius afterall.