Vijay Mallya, Patricia Kluge, and Eike Batista are all entrepreneurs who lost a billion or more and are now worth nothing. Masayoshi Son lost $60 billion and on

Vijay Mallya, Patricia Kluge, and Eike Batista are all entrepreneurs who lost a billion or more and are now worth nothing. Masayoshi Son lost $60 billion and only made back about $20 billion. Technically Bezos, Buffett, and Bill Gates have all lost billions many times, just due to market fluctuations, but that probably doesn't count. Mohammed bin Salman, the Crown Prince of Saudi Arabia, spends $1B like nothing: $500 million yacht, $300 million dollar house (one of many), $450 million on a painting. I'm certain that many members of that family have spent $1B or more. You know what they say: a million here, a million there, pretty soon it adds up to real money.