ON GAMBLES: FRED SMITH, The World Overnight: Founder, FedEx

Everything was going as planned in the early days of FedEx, until the Arab oil embargo hit in 1973. Suddenly our costs spiked and our cash evaporated. Right around then I went out to Vegas with this high roller I knew. We went to the casino and he got me a line of credit. I knew how to play blackjack from my days in Vietnam. It was a horrible war with a bad strategy and terrible consequences, but I met some great people and played a lot of cards. The odds in blackjack actually aren’t that bad if you know how to bet. The problem is most people get chicken and pull their money off of the table exactly when they ought to be doubling down. I didn’t have that problem. I won $27,000 and wired it back to the company. The myth says that money alone saved FedEx. The truth is that we owed so much damn money, $27,000 didn’t make much of a difference on the balance sheet. But it lifted our confidence at a time that we needed it.

No business school graduate would recommend gambling as a financial strategy, but sometimes it pays to be a little crazy early in your career.

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