The Las Vegas Sands Casinos magnate may be rolling in it now, but Sheldon Adelson actually grew up sleeping on the floor of a Boston tenement house in Dorchester. At 12, Sheldon started his own newspaper business with a $200 loan from his uncle. At 16, he ventured into the vending machine business before attending City College of New York for two years, and dropping out to join the Army as a court stenographer. He went on to build his empire by packaging toiletries, selling chemical spray, becoming a mortgage broker, selling ads, giving companies financial advice, investing in real estate, and running a tour business.
But it was tech conference Comdex that ultimately made him a fortune. Adelson sold Comdex for $816M in 1995, then built the $1.5B Venetian hotel and casino in Las Vegas. So what does Adelson do with all that dough? He invests in the Republican Party, giving candidates his blessing and donations, and most recently—and controversially—buying the Las Vegas Review-Journal.