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McClendon was smart, shrewd, visionary, and dogged—and he had trouble following rules. On occasion, when a gamble on a new gas field worked out, that helped him. But just as often, it hurt. His contrarian push into shale drilling revolutionized the global energy business and made him a billionaire. His disdain for convention attracted regulatory scrutiny, angered shareholders, and cost him his job running the company he built.

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Tom Monaghan was once a billionaire. He owned 244 classic automobiles, including a rare Bugatti Royale. He built a $30 million resort on a Lake Huron island. He hopped helicopters from the headquarters of the company he founded, Domino’s Pizza (DPZ), to watch the Major League Baseball team he owned, the Detroit Tigers.

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