Leslie Alexander is a true self-made billionaire. He dropped out of Brooklyn Law School at age 21 after his father died and headed to Wall Street to help provide for his mother. He found he was pretty good at investing, and after finishing his law degree he went back to trading bonds -- this time for himself. In 1993, he shelled out $85 million to buy the Houston Rockets. Good timing: Hakeem Olajuwon led the team to NBA titles in the next two seasons. In 2017 Tilman Fertitta agreed to purchase the Houston Rockets for a record $2.2 billion. Alexander first landed on the Forbes 400 in 2006 thanks to his stake in student loan securitizer First Marblehead, though the Rockets proved to be his best investment. In June 2016 First Marblehead was acquired by FP Resources for $5.05 per share, less than 1% of its 2006 peak price. Outside of business, Alexander is an animal lover; he funds a horse sanctuary in Middleburg,Virginia named after his mother, Evelyn.