Gladwell: Can an unlikely group succeed in a counterintuitive fashion? Can underprivileged outsiders have an advantage? As evidence, Gladwell cites the story of Sidney Weinberg, a high-school dropout who rose from the mailroom at Goldman Sachs to become a senior partner in the company and one of the most connected and powerful men on Wall Street.
This is the great mystery of Weinberg's career, and it's hard to escape the conclusion that Carnegie was on to something: there are times when being an outsider is precisely what makes you a good insider. It's not difficult to imagine, for example, that the head of Continental Can liked the fact that Weinberg was from nothing, in the same way that New York City employers preferred country boys to city boys. That C.E.O. dwelled in a world with lots of people who went to Yale and then to Wall Street; he knew that some of them were good at what they did and some of them were just well connected, and separating the able from the incompetent wasn't always easy. Weinberg made it out of Brooklyn; how could he not be good?
I read Gladwell for the anecdotes.