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10 Successful Entrepreneurs that Failed at First

When starting a business, there is always a possibility. The narrative that doesn’t get told enough is that behind most successful entrepreneurs lies a trail of failed ventures and missteps. 

There is a tendency for the general population to focus on the success of any given entrepreneur. However, many of them would have reached the heights they achieved without some big failures. If you’re an entrepreneur who has experienced your share of failures while creating your dream business, you’re not alone. Here is a look at their stories and what became of them after their rejections and hardships.


Colonel Harland Sanders

Colonel Harland Sanders, the founder of Kentucky Fried Chicken (KFC), epitomizes perseverance in the face of adversity. His early jobs were varied and challenging; he worked on a farm at ten and left home at thirteen due to his stepfather’s dislike of children. Sanders early adult life was no less tumultuous. He held numerous jobs, including insurance salesman, tire seller, and steamboat pilot, but was often fired for his inability to hold an appointment​​.

At 40, Sanders culinary skills led him to sell chicken dishes at his own restaurant. The establishment eventually gained popularity. Unfortunately, at 65, his restaurant failed. That led him to use his first Social Security check to seek partners for his chicken recipe. Despite being rejected 1,009 times, his tenacity never wavered. Eventually, his “Secret Recipe” was accepted, leading to over 600 KFC franchises. Despite rapid company growth, Sanders sold the company but remained its spokesperson until his death at age 90​​.


Fred Smith

Fred Smith is the founder of FedEx, and I think we all know that company. In college, Smith submitted a paper outlining his plans for his future company. While he didn’t receive a failing grade, his professor at the time wasn’t impressed and gave him just barely a passing grade. However, this less-than-stellar mark didn’t stop Smith from pursuing his entrepreneurship dream, and FedEx is still alive and well to this day.


Arianna Huffington

The renowned Huffington Post (now HuffPost) figurehead not only had a failed run for California Governor, but she received only 1% of the popular vote; 36 publishers also rejected her second book. It is hard to imagine someone so well-known and revered in the entrepreneur and publishing realm ever experiencing such failures. However, this experience was vital for Huffington as she used it as a platform for her future endeavors, especially when it came to overcoming failures.


Bill Gates

Bill Gates, Co-Chair of the Bill and Melinda Gates Foundation. https://depositphotos.com/ChinaImages

Before Microsoft’s success, Gates and Allen experienced failure with their first venture, Traf-O-Data, a company aimed at processing roadway traffic data. Despite the innovative concept, the business struggled due to a lack of market research and difficulty securing investments, leading to its eventual closure.

However, this setback was a crucial learning experience for Gates and Allen. The understanding of microprocessors gained during this time was instrumental in developing their first Microsoft product. Far from being discouraged, they used their Traf-O-Data experience to pivot towards opportunities in software, laying the groundwork for Microsoft’s future success.


Milton Hershey 

Well-known candy businessman Milton Hershey didn’t meet success in his first business go around. Hershey was not only fired from his apprenticeship at a printer, but his first three candy business ventures also failed before he went on to found the Lancaster Carmel Company.

In 1900, Hershey sold his caramel business for $1 million (the equivalent of $31 million today). Five years later, Hershey opened the first Hershey factory in Hershey, Pennsylvania. The area had acres of undeveloped land and other opportunities to expand his business. Over time, Hershey opened a popular theme park. The brand also created other beloved candy treats such as Almond Joy, Reese’s, and Twizzlers. It’s a good thing he didn’t give up because it’s hard to imagine the world without Hershey bars.


Walt Disney


At the tender age of 22, Disney faced bankruptcy due to the collapse of a cartoon series. This left him with nothing but a dream and a suitcase of essentials when he moved to Los Angeles. He first wanted to become an actor. However, that never worked out. The failure led him and his brother Roy to establish the first animation studio in California​​.

Disney’s next venture with Oswald the Lucky Rabbit seemed promising, but he soon lost ownership of the character along with his animation team. This setback, however, became the catalyst for the creation of Mickey Mouse who is now a cultural icon​​.

In the 1930s, Disney’s struggles continued with a personal breakdown, as he doubted the profitability of his cartoons and battled with anxiety and depression. Furthermore, Disney endured an animators’ strike before WWII and then saw his studio requisitioned by the army. He overcame this by channeling his creativity into patriotic films like “The New Spirit”​​. Despite these adversities, Disney’s resilience led to the groundbreaking success of “Snow White and the Seven Dwarfs,” the construction of Disneyland, and a legacy that redefined entertainment.



Henry Ford

I think it’s safe to say that almost everyone knows the name Henry Ford. If you don’t, Ford is best known for his creation of the automobile manufacturing assembly line. His innovation helped make automobiles more affordable for the everyday person and less of a luxury expense. However, Ford lost funding twice from investors who thought he was taking too long to finalize his concept. 

Ford, ever the persistent individual, didn’t give up and finally found a foreign investor who wasn’t afraid of taking a little risk. As the saying goes, the bigger the risk, the greater the reward. For Henry Ford and his third investor, that risk paid off. Ford continues to be a well-known and respected automobile giant.


Jeff Bezos

 It’s difficult to imagine that the Amazon powerhouse has ever faced hurdles, especially with Amazon’s current level of influence on the world market. However, Bezos, like many others, didn’t succeed when first breaking into the business world. 

His first business venture, an online auction site called Zshops, never took off and inevitably failed. This failure became the springboard to his creation which we now know as Amazon Marketplace.


Soichiro Honda

Soichiro Honda followed the car industry and knew that he wanted to be involved in the automotive industry at a young age. Honda left school as a teenager to become an apprentice for an auto repair shop in Tokyo. Almost a decade later, he went on to open his own branch of this automotive shop while trying to sell his automotive designs to Toyota, who rejected his ideas.

When gas became scarce during WWII, Honda created a 2-stroke motor that required very little gasoline to operate and was easily attached to bicycles. This innovation proved to be what he needed because, in 1949, the Honda Motor Company released its first motorized bike. Since then, Honda has become a well-known name in the car industry and one of Toyota’s biggest regrets.



Brian Chesky

One of the founders of the well-known app, Airbnb, Brian Chesky, and his fellow founders, had difficulty finding investors to jump on board with their idea. The idea came from their own experience of being low on money and making extra cash by renting out their apartment space.

They sent emails to seven major investors. Not one of them picked up their idea. Two of them never even responded to their emails. Finally, an investment company called Y Combinator took a chance on the concept.They provided Chesky with a much-desired loan to get his idea off the ground. Chesky and fellow founder Joe Gebbia and contributor Nathan Blecharczyk started targeting areas where big events were held, and hotel rooms would sell out fast. This venture provided people with alternatives to hotels and gave everyday people extra income to open their homes to others.



As you can see, there are many well-known business entrepreneurs out there who have met with rejection and hardship. Their stories teach us about perseverance, determination, and never letting one or more rejections stand in your way. If you believe in something enough and have the passion for seeing it through, then nothing can stop your dream from becoming a reality.


Photo credit: Daniel Oberhaus, 2019 under CC

Photo credit: Flickr under CC

This article was first published in 2021 but has been updated and expanded.

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Summer Anderson
Staff Writer: Summer Anderson is a mother, wife, writer and long time lover of the game of golf. Her passion lies in writing from the heart, and on topics that are most important to the Millennial generation. She hopes to impact those through her writing and advice on marketing and social media communication. When she is not on the golf course, blogging or watching "Frozen" with her little ones, she can be found designing websites in her home state of Pennsylvania.

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Staff Writer: Summer Anderson is a mother, wife, writer and long time lover of the game of golf. Her passion lies in writing from the heart, and on topics that are most important to the Millennial generation. She hopes to impact those through her writing and advice on marketing and social media communication. When she is not on the golf course, blogging or watching "Frozen" with her little ones, she can be found designing websites in her home state of Pennsylvania.

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