It's possible the richest CEOs are actually the worst at picking bets, because they're the ones who picked bets that were the least likely to pay off, and therefore got the biggest pay out when they won. If 50 people were making the same bet as Reed Hastings, then Netflix would've found it far harder to succeed, since they would've been competing for talent, content and customers with 50 other companies. The reason Netflix exploded in growth is partly because they were the only ones serving that market. Maybe that was a genius stroke of insight, or maybe he was one of a thousand people making bad bets, and he's the one that it paid off for.