In 1974, FedEx was days from bankruptcy with just $5,000 left in its bank account — not even enough to cover a $24,000 jet fuel bill. Founder Fred Smith flew to Las Vegas and put it all on the blackjack table. By Monday morning, the company account had $32,000. When confronted by his executives, Smith shrugged: "I knew we needed money for Monday." The $27,000 in winnings kept the planes flying for one more week — just long enough for Smith to close an $11 million rescue deal. FedEx now makes over $90 billion a year.