He's my favorite example to bust the "smarts and hard work" myth of billionaires. He had parents with good, union jobs that allowed him to go to Princeton, where he dropped out of a physics major (into CS) because it was too difficult. The school's connections, though, got him a job at a hedge fund, where he was assigned to study the investment potential of e-commerce on the nascent Web. He saw the enormous potential, but was so bad at his job that he couldn't convince the other executives that they wanted some of that money. So he left the job, got a large loan from his parents, and started Cadabra in a garage he rented in a conscious nod to Silicon Valley mythos. Oh, Cadabra? He was going to call it that, but his lawyer convinced him to go with his second choice of name, because that one sounds too much like cadaver. The company was profitable in a month, and then he used all manner of dirty tricks to run the competition out of the market.
Nothing in his story indicates anything but dumb luck of randomly being the one in the right time and place to succeed. If it was smarts and hard work, there were hundreds of other e-commerce contenders who put in at least as much as he did.