WALLY AMOS
In the mid-1970s, Wally Amos turned his love for cookies into the brand Famous Amos. A phenomenon in his day, Amos sported a trademark Panama hat and shirt that were later inducted into the Smithsonian Institution. But food fads fade; facing falling revenue, he had to sell controlling interest in his company, and he was pushed out in the late 1980s. Not long after, he was fighting to keep his house. Luckily, Wallly Amos was later able to make an unexpected comeback.
WILLIAM 'BUFFALO BILL' CODY
The tradition of entertainers going broke dates back to at least the late 1800s, when Buffalo Bill organized his Wild West Show. The show toured the world, and Buffalo Bill made a fortune for his time. But he was generous with friends and workers -- to a fault, by most accounts. The show went belly-up in 1913, and Cody later declared bankruptcy.
BERNIE MADOFF
From the 1970s to the 2000s, Bernie Madoff was known as a financial whiz and boasted a growing list of high-profile clients. But a Securities and Exchange Commision investigation that began in 2006 and the market collapse in 2008 exposed his operation as a Ponzi scheme. He pleaded guilty to fraud in 2009 and was ordered to forfeit his fortune.
THOMAS JEFFERSON
While we often hear that we need a businessperson to run the country, some of our nation's storied leaders simply had no business savvy. Thomas Jefferson -- the principal author of the Declaration of Independence and the third president of the United States, as well as a plantation owner -- died deeply in debt. His Monticello estate and all his possessions (including 120 slaves) were auctioned off to help pay his debt, a substantial amount for the time.
ULYSSES S. GRANT
After leaving office in 1877, the 18th president of the United States tried his hand at business in the railroad industry and founded an investment firm in New York. Both ventures failed, leaving Ulysses S. Grant with next to nothing, as he'd given up his military pension and a president's pension didn't exist at the time.It wasn't until nearly a century later that another president became the first to receive one.
HENRY PELLATT
A Canadian soldier and financier, Henry Pellatt heavily invested in hydropower and rail, but he was perhaps most famous for his extravagant Casa Loma, the largest private home ever built in Canada with a staggering number of rooms. But bad investments and government takeovers of some of his businesses broke him: He declared bankruptcy in 1924 and was forced to leave Casa Loma. He later died at the home of someone who used to be very far beneath him.
RICHARD WHITNEY
A successful banker and broker, Richard Whitney was on the board of the New York Stock Exchange when the crash hit in 1929, and led efforts to save the market. He didn't succeed, but the Depression isn't what brought him down. Rather, he financed a luxurious lifestyle with money borrowed from his brother and well-heeled friends, and he ended up deeply in debt. So, he turned to embezzlement. In perhaps the first high-profile perp walk, he boarded a prison-bound train at Grand Central Station as thousands turned out to watch.
JOHN SUTTER
John Sutter was an immigrant who hit California in 1839, won a Mexican land grant and built the Sutter's Fort settlement near what is now Sacramento. Soon he was employing hundreds of people. However, he was eventually refused his Mexican grants and by 1852 was bankrupt.
CHARLES SCHWAB
A steel magnate (and not the founder of the well-known brokerage firm), Charles Schwab led Bethlehem Steel and Shipbuilding to glory. He was also known for an opulent lifestyle of mansions and parties and as the man who once broke the bank at Monte Carlo. But the crash of 1929 left his Bethlehem Steel stake virtually worthless, and he lived in a small apartment until his death in 1939. In an ironic twist, the timing of his death proved unfortunate as well.
OSKAR SCHINDLER
Bankruptcy was a higher calling for Oskar Schindler. He ran two factories in Nazi Germany using Jewish workers. Most of the money he made was spent protecting those workers. After the war, he went bankrupt and lived on financial aid from those whose lives he saved until his death in 1974.
BERNIE EBBERS
Known for a time as the "telecom cowboy," Bernie Ebbers built WorldCom into a giant, with $7 billion in annual revenues. But he took a loan from the company in 2000 to cover stock losses, setting off an SEC investigation that revealed the company had been cooking its books for years. In 2002, Ebbers resigned, and the company declared bankruptcy. He ended up in prison in 2006.
KENNETH LAY
Named CEO of Houston Natural Gas in 1964, Kenneth Lay grew his company into the giant energy company Enron, which peaked at No. 7 on the Fortune 500 list. But it collapsed in the early 2000s as a story of complex financial misdeeds emerged. Lay was convicted of fraud and conspiracy in 2006 as part of the ensuing scandal. However, he never served his term prison.
MARION "SUGE" KNIGHT
A pioneer on the business side of rap music, Marion "Suge" Knight co-founded Death Row Records with Dr. Dre and was riding high when artists like Snoop Dogg and Tupac Shakur went big in the 1990s. But links to violence, feuds and other legal woes followed. Knight declared bankruptcy in 2006, saying he was millions in debt and had just $11 to his name. A few remaining personal items were later auctioned off on the debut episode of a reality TV show.
MARK TWAIN
One of America's most famous writers, Mark Twain earned a substantial fortune from his works. But he lost most of it to bad investments on fickle projects, like an early typesetting machine that proved prone to breakdowns. Creditors chased him for years, but he found an ingenious way to elude them.
JOHN DELOREAN
John DeLorean was a famous car designer even before he launched his own company, known for the sleek car with gull-wing doors immortalized in "Back to the Future" (watch clips of the car's cameo). But he didn't take off in real life. In 1982, he was accused of illegal activity to raise money for his struggling venture. Six years before his death, he declared bankruptcy.
MILTON HERSHEY
On the flip side, some business icons failed and came back stronger. Born in 1857, Milton Hershey founded his first candy company in Pennsylvania when he was just 18. It failed. So did a second try in New York City. At age 28, he was nearly broke. He finally found some success with a different type of sweet treat before he turned, eventually, to chocolate.
P.T. BARNUM
His career as a showman began in 1835, and P.T. Barnum spent years displaying a collection of wild animals, albinos, giants and other oddities in New York. Surprisingly, more ordinary business ventures got him into trouble. In the early 1850s, Barnum was working on a development in East Bridgeport, Conn., and loaned money to Jerome Clock so it could move into the area. The company later went bankrupt, taking most of Barnum's wealth with it. But in 1871, Barnum, 61, bounced back. He entered the circus business, creating the "Greatest Show on Earth," which turned into a show that's still running today.
HENRY FORD
You may not have heard of Detroit Automobile, founded at the turn of the century by a young engineer and entrepreneur. It produced only a handful of cars over a two-year period and then went bust. Consider it a test. Two years later, the same man -- Henry Ford -- founded Ford Motor. Another surprise? Reorganized after going bust, Detroit Automobile became another well-known brand.
