FedEx Founder Gambled Their Last $5,000 at a Blackjack Table 

FedEx had only $5,000 in its checking account, and faced a $24,000 jet fuel bill. After he was turned down for a loan by General Dynamics, Smith took his last $5,000, flew to Las Vegas and played blackjack. He won $27,000 – enough to pay the fuel bill and operate for another week.
– World’s Strangest | FedEx: Founder Gambled His Last $5,000 at a Blackjack Table to Stave Off Bankruptcy.

Might seem risky on the surface, but really he had nothing to lose.