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.

Many super-paid athletes famously end up broke very quickly after their careers end. Some NBA names here [0] but it's not specific to basketball - it typically correlates with coming from poverty and/or lack of financial education.

[0] https://www.thesportster.com/basketball/15-nba-players-who-w...

Bill Hwang, revered as a God Of YOLO on WallStreetBets, once lost $20B in two days: https://www.bloomberg.com/news/features/2021-08-09/where-is-...

Mike Tyson, Evander Holy field, I'd imagine there'd be a lot of boxers.

> Can you cite some examples?

Alongside the other examples in this thread, Donald Trump lost at least $1b during the first two years of his term.

> If it were easy, presumably a lot of people have done it.

The easiest way to lose a billion is to start with more than a billion, and there aren't really a lot of people in that position.