3 Wealthy Investors and Entrepreneurs Who Have Declared Bankruptcy

You’d be surprised at the number of successful businesspeople who have had to file bankruptcy at some point in their journey to success. Here are the stories of three famous people who tried, tried again, and eventually succeeded, and the lessons we can take away from their stories. 

Dave Ramsey 

If you research finance and investing online at all, you surely know Dave Ramsey’s blog Good Financial Cents. Dave is one of the most widely read and highly regarded personal financial advisors on the internet. What you probably don’t know is that he came by his vast knowledge the hard way. 

Dave got off to a great start in his career, building a portfolio of rental properties worth over 4 million USD by the age of twenty-six. However, his holdings were heavily leveraged and creditors eventually came to call in his debts, forcing him to file bankruptcy. 

The bankruptcy inspired him to move away from real property investments and go in a new direction, and he began to attend workshops on consumer finance. After a while, he began to give financial advice to other members of his church.  

From his own experience, his experience with his clients, and the information he learned by educating himself, Dave created a personal finance course of his own. At the urging of his clients, he eventually expanded that course into his first investing bookFinancial Peace, in 1992. 

Financial Peace proved to be very popular, launching his radio career which started locally and then grew into the nationally-syndicated The Dave Ramsey Show. Dave also had a television show on the Fox network for three years. He continues to write books on personal finance, many of which became bestsellers and hosts his blog, seminars, and investing courses on his website. 

Dave Ramsey’s current net worth is about 55 million USD. How’s that for a comeback?  

PT Barnum 

Did you see the recent movie, The Greatest Showman? It is actually the last of several on PT Barnum and the circus he is most famous for.  

Phineas Taylor (PT) Barnum started life as an impoverished orphan and through trial and error, did indeed become the greatest showman ever, as well as a wealthy and well-regarded politician in his home state of Connecticut.   

PT Barnum was born in 1810 in Bethel, Connecticut, and was a young entrepreneur there, starting a general store, creating a state-wide lottery, founding a small local newspaper, and engaging in book auctioning and real estate speculations before moving to New York City.  

At age 25, he started his career in entertainment, creating the variety act “Barnum’s Grand Scientific and Musical Theater” and eventually purchasing Scudder’s American Museum, which he renamed after himself. By renovating the building itself and adding unusual exhibits he was able to turn the Museum into one of the most popular entertainment destinations in the city. 

Unfortunately, the building housing Barnum’s American Museum burned down not once, but five times. The last rebuild was very costly and the revenue of the Museum could not support it, forcing PT Barnum to file bankruptcy. 


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Using the financial lessons he learned the hard way, PT Barnum began to give lectures called “The Art of Money Getting.” Income earned as a lecturer allowed him to repay his debts and restart his entrepreneurial entertainment career.  

Although PT Barnum is probably most famous for his traveling three-ring circus, he did not create that venture until he was 64 years old! His was one of the first traveling circuses and he is credited with being the first circus owner to buy a train to transport the circus.  

PT Barnum’s traveling circus grew and performed long after his death, and its final iteration, Ringling Bros. and Barnum & Bailey Circus closed in 2017 after 147 years in business.  

Henry Ford 

Henry Ford is known today as the first manufacturer of affordable automobiles and inventor of the assembly line method of automobile production. But did you know that Ford failed in creating his first two automobile manufacturing companies? He did – and had to file bankruptcy due to the failure of the first.

Henry Ford was an early tinkerer, taking apart and putting together a pocket watch he received at age twelve and eventually repairing other’s watches. He worked the family farm but also had jobs in engineering as a young adult, eventually working for Edison Illuminating Company of Detroit and becoming its chief engineer. This gave him the time and funds to work on his automobile design and begin his manufacturing ventures. 

At the age of 40, Henry Ford created his third automobile manufacturing company, the Ford Motor Co., with a cash investment of $28,000. It was with this third venture he perfected his assembly-line production methods, established a high working wage for his employees, and successfully marketed his product.  

Legend has it that just as Ford’s bank balance dwindled to $223.65, the Ford Motor Company sold its first car, starting a movement that would change the lives of Americans and the landscape of our land forever.   

Lessons Learned from Dave Ramsey, PT Barnum, and Henry Ford 

  • Early poverty is no obstacle, but rather can serve as inspiration and motivation; 
  • Tenacity is key to overcoming financial challenges or even a bankruptcy; 
  • You can come back from going too far into debt when financing a business venture; 
  • You can come back and learn from financial mismanagement;
  • As long as you have a strong entrepreneurial drive, you can recover from a financial failure; 
  • If you don’t succeed at one business venture, try something different; 
  • You are never too old to start again; 
  • Take risks, because failure isn’t the end, and; 
  • If at first, you don’t succeed, try, try again! 

About the Contributor 

Veronica Baxter is employed as a legal assistant and blogger. She is based in Philadelphia, where she works alongside David Offen, Esq., who is a busy Philadelphia bankruptcy lawyer

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