From Trump to Jobs: Billionaire Comebacks

April 8, 2008— -- It was a stinging blow for Steve Jobs when a boardroom power struggle ousted him from Apple, the company he co-founded as a 21-year-old. A friend was so concerned over what the distraught Jobs might do that he drove to his house and sat with him for hours.

Jobs didn't stay down for long though. He soon began poaching Apple employees for his new company Next and picked up a digital graphics company, later called Pixar, from George Lucas for $5 million.

These moves set Jobs up for a spectacular comeback. He sold Pixar, which made blockbuster films like Toy Story, to Disney in 2006 for $7.4 billion. Earlier, a struggling Apple came knocking at Next's door, hoping the company could help bolster Apple's flagging software lineup. Apple paid about $400 million to acquire Next in 1997.

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Apple didn't only need Jobs' company, it also needed his leadership. In Jobs' absence Apple faltered severely. Macs were rapidly ceding market share to PCs, and the company was fumbling a release of a new operating system. In September 1997, Jobs was named chief executive officer.

Jobs' second term has become a remarkable success story. Mac sales are booming, iPods are hugely popular and iPhones are earning the company new victories in the cellphone market. Shares of Apple are up an incredible 1,500% over the past five years.

Jobs' roller coaster trajectory isn't unusual. Billionaires actually suffer more major career and business setbacks than the rest of us.

"It's not that the wealthy are incompetent," explains Russ Alan Prince, president of Prince & Associates, a research company specializing in private wealth. "It's just that they try more."

Take Donald Trump. He shot to billionaire status in the 1980s by borrowing heavily to finance ambitious real estate projects. He lost it all (and more) in a 1990 real estate crash. (Trump would later recall passing a homeless person and realizing that the man was wealthier than he was.)