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.)

While they fail more, billionaires respond with greater persistence. They are more likely to try again in the same field. Trump kept building, began licensing his name to other developers and started clawing his way out of the hole. By last year, Forbes estimated he was the 117th wealthiest American.

Persistence in the same field pays off. While an initial business venture in the area might be a failure, the businessman or woman is building a network and knowledge that could provide the groundwork for another more successful venture.

Racing tycoon O. Bruton Smith is another one who stuck to familiar territory after failure. For him, it was the racetrack. Smith couldn't make it as a driver so he turned his attention to the business-side of the sport. He began promoting dirt-track races.

Smith saw an opportunity to build a new track in Charlotte. He raised $450,000, an impressive amount in the early 1960s, and broke ground on the project. The money wasn't enough, though, and soon Smith's track was bankrupt.

After dallying in auto dealerships, Smith returned a decade later. He used proceeds from his car business to buy back the stock in the track. With the sport booming--and with Smith's savvy marketing--the track was a roaring success this time. Smith now owns six tracks and is worth an estimated $1.2 billion.

Obstinacy is no guarantee to riches. Trying again and again in a business with no potential is a sure way to find bankruptcy and stay there. But in the right field at the right time, a stubborn streak can be just as important as hard work, talent, drive and luck.