The Right Kind of Asshole

Though the most successful founders are usually good people, they tend to have a piratical gleam in their eye. They're not Goody Two-Shoes type good. Morally, they care about getting the big questions right, but not about observing proprieties. That's why I'd use the word naughty rather than evil. They delight in breaking rules, but not rules that ... See more

It is a better world if our most prominent people are moral exemplars with happy family lives. However, after a decade of meeting billionaires, reading biographies of highly successful people, and building products myself, I’ve come to accept that the opposite is probably true. The highest level of success requires wholly unreasonable people. Musk ... See more

It turns out they have a lot in common. They are all independent thinkers who do not let anything or anyone stand in the way of achieving their audacious goals. They have very strong mental maps of how things should be done, and at the same time a willingness to test those mental maps in the world of reality and change the ways they do things to ma

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Being a founder requires constant calibration between arrogance and humility, optimism and pessimism. You need the arrogance to believe that you have something important to say, but the humility to know most people won’t care. You need the optimism to convince yourself and others (employees, investors, customers) to believe in you. But you need pes... See more