I am interested to know your thoughts on this question and how you formed your opinion on it. I foresee people citing Steve Jobs, but is there a certain point in one's trajectory before which being an asshole smothers one's chances of success? How much harder is it to succeed with those personality traits?
Assholes and sociopaths succeed because they are very efficient at doing the things normal and nice people may find hard or wrong - but which nevertheless lead to business success. The overall issue I wonder about, is that if sociopaths wind up at the tops of corporate ladders, is the culture they set, while useful, in fact counterproductive.
There are a lot of people who come across as assholes in the blogosphere, but could be quite the opposite in person. I think just having a reputation of being an asshole is enough to hurt your chances of working with some companies or people to some degree. Hopefully that is countered by a degree of tenacity and ambition "assholes" tend to have.
A good example would be Jason Calcanis. I've never met him in person (though I did come within 5 feet of his office when I interviewed at Mahalo). He comes across as someone I would never want to have dealings with, business or otherwise. Good thing for him I'm just a small fish. But I would probably feel the same way if I were the CEO of a big company looking to buy Mahalo. But I bet Mr. Calcanis wouldn't want to be bought out anyway.
An excellent opportunity has arisen for two almost identical companies, A and B, but it involves ethics that would make a decent person uncomfortable. A is run by a decent person, and they skip the opportunity because it's the decent thing to do. B is run by an asshole, and they jump at the opportunity with glee, maybe even with a small chuckle at all the companies that would have passed up the opportunity on ethical grounds.
Company B is now better off, because of, not despite, their asshole.
Bill Gates is widely regarded as an asshole. Likewise Steve Ballmer.
Counter-examples include Warren Buffett, who is regarded as a sweetheart. Larry and Sergey are famously nice, though they've apparently had their moments of being assholes. Sam Walton was nice to his people but ruthless in every other way.
Why not? Look at almost any construction site in an ex. Soviet block - bunch of assholes 'managing' a crowd of wage-workers from a ex Soviet republics. It is the most popular business in Russia nowadays. ^_^
