The two great icons of our industry, Bill Gates and Steve Jobs, came up in a talk given by Malcolm Gladwell recently at the Toronto Public Library. In discussing capitalism and entrepreneurship, Gladwell makes the point that amorality — i.e. the absence of a moral compass in making business decisions — is a fundamental prerequisite for being a successful business leader. He considers the entirety of Bill Gates' tenure as Microsoft chief to be that of "the most ruthless capitalist," which is not too dissimilar from his analysis of Steve Jobs' leadership. The difference, says Gladwell, is that Gates turned away from that amoral (note, not immoral) behavior after retiring and took up the task of spending his wealth on philanthropic projects.
It's for his latter work, not for how much money Gates made with Microsoft, that Gladwell expects him to be remembered some 50 years from now. As to Jobs, he suspects people would be asking, "who's Steve Jobs again?" Though his language feels tongue-in-cheek, Gladwell's broader point is about the fact that we're idolizing businessmen for their money-making aptitude, whereas their long-term legacy will actually depend on the broader impact they had on the world.
Keep watching Gladwell's talk for his discussion of what he calls "the fetishization of being first" and the great examples he gives of tech companies who were first to do something, but lost out in the end to better, more refined competitors who came later. Remember Lycos? Gladwell advises that where you really want to be is first-ish.