I would agree that most people with that exact background would have learned the hard way to care about privacy.

The single example that ascended to be the CEO of Apple though? That selection process would seem more relevant than any personal background.

My base assumption is that any impressions we have about Tim Cook (or any other executive of a company that size) are a carefully crafted artifact of marketing and PR. He may be a real person behind the scenes, but his (and everyone's) media persona is a fictional character he is portraying.