10 Wildly Successful Businessmen Who Lost It All


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It is the dream of many to make their fortune in this world. Only a select few succeed. Unfortunately it is the same tricks, dealings, and knowledge that make these men so powerful that can in turn ruin them. Some completely recover, others fail, but all of them have interesting stories to tell. The following are ten successful business men who lost it all.

William C. Durant

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William C. (Billy) Durant cofounded General Motors and Chevrolet. He was the automobile industry’s leading pioneer within the United States.

William C. Durant started as a carriage salesman in Michigan. In 1886 he created the Coldwater Road Cart Company. He went on to found the Flint Road Cart Company and turned it into a $2 million business. He’s credited with developing the automobile dealer franchise.

Durant hated cars at first, but he saw the need for government regulations. He purchased Buick with the idea of improving safety. Following much success he started General Motors in 1942. After becoming financially extended, GM let him go. Once he partnered with Chevrolet he was able to get his job back, buying enough shares to become GM’s president. In the 1920’s he joined the Rockefellers in buying many stocks. It was to prove to the public that the stock market was safe. The 1929 Wall Street Crash left him bankrupt and he ended his years managing a bowling alley in Flint Michigan.

Donald Trump


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A successful real estate developer, Donald Trump has bounced back from bankruptcy to become a household name. His many hotels, office buildings, casinos, and television show have kept him in the spot light.

Donald Trump started in his dad’s business. He moved to Manhattan in 1971, where he saw financial opportunity. In the 1970’s he bought an old rail yard that he sold as a convention center site. He also bought the failing Commodore Hotel next to the Grand Central Station and reopened it with the Hyatt Hotel Corporation. He opened Trump Towers in 1982 after leasing the site. During the 1980’s Trump opened a casino with Holiday Inn Corporation in Atlantic City. He eventually bought out Holiday Inn. He went on to open Harrah’s at Trump Plaza, followed by Trump’s Castle and Taj Mahal.

It was in the 1990’s when the real estate market declined that Trump’s empire was in jeopardy. He survived bankruptcy, and Trump was back on top by 1997. He managed to be worth $2 billion after being $900 million in the red.

Jordan Belfort


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Author and motivational speaker, Jordan Belfort has overcome his past. He ran a boiler room and was involved in stock market manipulation that landed him in jail for 22 months.

Jordan Belfort founded Stratton Oakmont, a brokerage firm in the 1990s. He had a reputation as a partier with serious drug problems. Belfort had 1,000 employees and was dealing with $1 billion in stock issues. True to his personality he bought a yacht from Coco Chanel and insisted on sailing in high winds. After sinking off the coast of Sardina, Italian special forces had to rescue everyone onboard. His brokerage office became the target of complaints and was prosecuted by a multi-state task force. In 1998 Belfort was indicted for money laundering and securities fraud. Investors lost $200 million. Belfort was convicted after cooperating with the FBI and had to pay back $100 million.

Belfort eventually overcame drugs. Today he tours, doing motivational speaking. He’s written two books and is the inspiration for a Martin Scorsese movie that is underway with Leonardo Di Caprio.

M.C. Hammer


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Born Stanley Kirk Burrell, M.C. Hammer is a rapper, actor, dancer, entrepreneur, and spokesman whose quick rise to fame resulted in an abrupt decline. With God on his side, he has bounced back with riches worth more than money.

During the 1980s and 1990s M.C. Hammer enjoyed a rapid rise to success. As a Hip Hop icon with over 50 million records sold worldwide, his songs “U Can’t Touch This” and “2 Legit 2 Quit” made him famous. He has kept his name in the public in a variety of ways. He became a minister with a TBN program called Christian Ministry. The Hammerman cartoon was created in 1991, and a reality show called Hammertime on A&E aired in 2009. During 2003 he was a judge on Dance Fever. He became the first Hip Hop artist with diamond status.

Once worth $33 million, he spent too much on luxury items, friends, and family. Ending up $13 million in debt, he went bankrupt in 1996. Today he is recovering, claiming he puts God first and business last.

P.T. Barnum


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The founder of the Ringling Brothers and Barnum & Bailey Circus, P.T. Barnum was a successful showman and scam artist. He coined the phrase “There’s a sucker born every minute”

P.T. Barnum was a small business owner. In 1834 he moved to New York City and started his entertainment career with a variety troupe named Barnum’s Grand Scientific and Musical Theater. He purchased Scudder’s American Museum and used it to promote popular hoaxes. He worked as a promoter for the singer Jenny Lind in 1850. He was able to give her $1,000 per evening.

In the 1850s bad investments and years of litigation caused his economic reversal. After hitting bottom he became a temperance speaker. Barnum eventually added wax figures and an aquarium to the museum. He served as a republican on the Connecticut Legislature for two terms, and he worked to put an end to slavery. While mayor of Bridgeport, he improved the water, enforced prostitution laws, and installed gas lights. He co-founded the Bridgeport Hospital in 1878, later becoming its president. He died April seventh of 1891.

Francis Ford Coppola


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One of the leading directors of the twentieth century, Francis Ford Coppola brought a series of award winning movies to the big screen. When times got rough he could always turn to his family for help.

Bedridden with polio as a child, Francis Ford Coppola had to be creative and entertain himself. He started with puppet shows. Later he studied at Hofstra University in New York, followed by a UCLA film program. His first success was Finian’s Rainbow, a 1968 musical. He won an Academy Award in 1970 for Patton and he went on to do the Godfather series. Those movies earned him Best picture. In 1979 he did Apocalypse now. During the 1980’s and 1990’s he gave us the final Godfather, The Outsiders, the Cotton Club, and Bram Stocker’s Dracula. After 1997’s The Rainmaker he focused on producing and working in his winery.

It was in 1982 that Coppola was $300,000 in debt from making the Godfather trilogy. He was bankrupt after a failed musical called One From the Heart. Being a part of a loving Italian family, his mother helped him get back on his feet.

Sean Quinn


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Sean Quinn is the ideal rags to riches story. Unfortunately he didn’t stay on top long, bringing his family down with him.

Quinn started his career in 1973 by extracting and selling gravel from his family’s land. This led to Quinn Cement where he made his fortune. He set up the Quinn Group that included Quinn Hotels, Quinn Glass, and Quinn Lite Pac. Sean founded the Quinn Financial Services in 1996. By 2007 he was buying Ireland’s largest insurer. He had increased his stake in the Anglo Irish Bank to 15 percent.

The Quinn fortune took a hit during 2008. The Anglo Irish Bank’s near failure caused the Quinn family to lose 2.8 billion. In 2008 Quinn Insurance received a 3.25 million fine for breaching insurance regulations. The bank requested the 2.8 billion in loans by Quinn to be repayed.

On November 11 of 2011 Quinn applied for voluntary bankruptcy. He was declared bankrupt on January 16 of 2012. The Quinn family no longer manages The Quinn Group. Additionally, Sean Quinn served nine weeks in jail for non-cooperation.

Harry Macklowe


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Harry Macklowe was a New York City real estate developer and investor who was at the top of his game. Like so many successful business men, his greed got in the way of his fortune.

Harry Macklowe became a real estate broker in 1960. He soon became a builder, and he developed several modern buildings such as The Metropolitan Tower. His firm is Macklowe Properties, which owns many New York Landmarks, including Two Grand Towers.

Macklowe ordered four buildings to be demolished late at night in 1985. He didn’t have permits. A Time’s Square welfare hotel was one of them. He was fined $2 million. By 2003 he was regaining his fortune by purchasing the General Motors Building. The value doubled after he talked Steve Jobs into opening an Apple Store there. In 2007 Macklowe purchased seven skyscrapers in Manhattan from the Blackstone Group for $6.8 billion. $50 million was his; the rest came from loans and a hedge fund. He lost all seven in 2008 for failing to refinance a $5.8 billion loan. He lost the General Motors Building among them.

Eddy Groves


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Eddy Groves was the Australian founder and one time CEO of ABC Learning. It was the world’s largest childcare provider in its day. Groves was known as Fast Eddy, due to his love of sports cars.

Eddy Groves started at age 19 with a milk route purchased with help from his father in law. He expanded the business into what is now Quantum Food, Queensland’s biggest milk distributor. In 1988 Groves opened a Brisbane child care center. He saw it as a needed source, same as milk. It became a successful franchise, and it was listed on the Australian Stock Exchange by 2001. His share was worth 2.5 billion, making him the richest man in Australia. During 2008 there was a 42 percent fall in profit. He sold his shares due to margin calls from the bank. It was made aware that Groves didn’t explain fully the effects of the margin calls to other shareholders. He left the company in 2008 with his wife. By the end of that year ABC and groves owed over $1 billion because of mistakes in financial reporting.

Paul Castle


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A polo mate of Prince Charles, Paul Castle was hit hard by the recession. That combined with health issues was more than he could handle.

Paul Castle was born to a tailor in Golders Green. He left school when he was only 14, and made his fortune working with children’s clothing. He went on to be Britain’s youngest polo team sponsor in the 1990s. He used hundreds of thousands of pounds to get star players from Australia and Argentina. Castle is remembered for being fined 5,000 pounds and not being allowed to play for nine months after using a wooden mallet to hit another player.

Castle moved to Florida and lost his fortune by age 27. He made disastrous deals and also lost money in a gas and oil exploration Company. He returned to the UK and rebuilt his property portfolio. He owned an apartment in Switzerland and houses in France, London, and Ascot. He opened a bistro in Britwell called The Goose. At age 54 Castle killed himself. He was struggling with a heart condition.

January 28, 2013