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How 5 Entrepreneurs Made Billions, Lost It And Made It Back Again

This article is more than 9 years old.

This story appears in the March 22, 2015 issue of Forbes. Subscribe

It's difficult enough to make a billion bucks - and even harder to earn it back once you have lost it. But several members of the Forbes Billionaires list have made a ten digit fortune not once but twice. Among them, Iceland's Thor Bjorgolfsson, who returns to the ranking this year for the first time since 2009. To learn how Thor earned it back, read Crazy Comeback: The Man Many Blamed For The Economic Meltdown Is A Billionaire Again. Here's how others did it:

Donald Trump

U.S.

Net Worth: $4.1 Bil

The Donald shot to billionaire status in the 1980s as he borrowed big to finance ambitious real estate projects. His fortunes turned quickly with a 1990 real estate crash that sent him tumbling into debt and a negative net worth. But Trump kept building, and scraped his way back to billionaire status by 1997. He is now worth more than ever, thanks to trophy New York properties.

Yasumitsu Shigeta

JAPAN

Net Worth: $1.95 Bil

College dropout founded mobile phone distributor Hikari Tsushin in 1988 at age 23. He made and lost $39 billion in four months during the dot-com craze of 2000. He reinvented himself as a medical insurance provider and returned as a billionaire in 2005.

Maggie Magerko

U.S.

Net Worth: $1.2 Bil

Wild spending and a historic housing crash put 84 Lumber (a Home Depot for pros) on the brink of bankruptcy in 2009. Magerko put her checking account, houses and jewelry on the line to get loans that kept 84 Lumber afloat, then fired two-thirds of her workers and closed half of her stores. Six years later she's a billionaire once more, running a smarter, leaner firm.

W. Herbert Hunt

U.S.

Net Worth: $1.7 Bil

Hunt and his brother Nelson Bunker Hunt invested heavily in silver in the 1970s, but as the commodity collapsed in the 1980s, Hunt slipped into bankruptcy. Hunt stayed in the oil game and in 2012 sold a chunk of his acreage for $1.5 billion. He returned to billionaire status in 2013.

Robert Stiller

U.S.

Net Worth: $1.2 Bil

Founder of Keurig Green Mountain Bob Stiller made a fortune selling coffee and K-cups, joining the three-comma club in 2011. His spending caught up with him: In 2012 he sold 5 million shares to pay off money he borrowed against his stock. Price gains made him a billionaire once more.

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