Successful entrepreneurs who failed in business before making it big

We see their faces and names on magazine covers, TV documentaries, business news, and in some important events past or present. They have gained fame through the success of their companies and brands, but these entrepreneurs had tried their hand on business and, at one point, didn’t work like a Midas touch.

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It goes to show that even when worst things happen in your entrepreneurial journey, it can never stop you from achieving your goals, as long as you keep moving forward with determination and persistence. These entrepreneurs embraced failures as stepping stones towards their ultimate goal, which made them attain the success they now have. Their stories are sources of inspiration, especially those who are going through the challenges, difficulties and frustrations of starting and sustaining a business.

Richard Branson

Virgin Group Founder Richard Branson is soaring high with the success of his companies like Virgin Atlantic, Virgin Games, Virgin Holidays and so much more. Yet, he also had ventures that hit a dead end. He has openly talked about these experiences and shared what he learned from them. At a very young age, Branson already exhibited an entrepreneurial mind. While still in school, he tried breeding budgerigars and growing Christmas trees and selling them. The birds took off, but not his venture. He then opened Student magazine. While it wasn’t successful, it paved the way for Virgin Records. He also made mistakes along the way, which led to companies like Virgin Cars, Virgin Brides and Virgin Cola to shut down. That didn’t deter him from growing his existing businesses and starting new ones. And look where he is right now.

Colonel Sanders

His face is right there at the Kentucky Fried Chicken logo, but Harland David Sanders, who later earned an honorary title of “colonel”, took a long time before he began his entrepreneurial journey. He first worked on several jobs in his 20s and 30s before he opened a service station when he was about 40 years old. While running his service station, he also served food to customers enabling him to open a café and later acquire a motel. But they were not without challenges. Feisty competition, a fire incident, route changes, the Great Depression and World War II were some of the adversities he had to face that led to the closure of his businesses. He went on to do other jobs until he franchised his chicken recipe to restaurant owner Pete Harman and other restaurant owners. That’s how KFC was born.

Milton Hershey

Hershey’s name is synonymous to sweet success. But it was after a few failed businesses that Hershey finally hit the gold mine in the candy industry. He first opened a candy shop in Philadelphia before he built some ventures in Chicago and New York. All of them closed later on. However, it was when he started the Lancaster Caramel Company that he made progress on his entrepreneurial journey. Eventually, he sold the Lancaster Caramel Company and established the Hershey Chocolate Company.

Christina Wallace

An Entrepreneur In Residence at Harvard Business School, Christina Wallace can talk about failures and overcoming them because she, herself, had her fair share of experiences when it comes to facing complexities in business and making difficult decisions to surmount such challenges. She co-founded the fashion company Quincy Apparel, opened Startup Institute New York as its founding director, and established BridgeUp: STEM, an educational tech startup at the American Museum of Natural History. With the failure of her first company, she spent weeks in bed watching TV to weep for her loss before she mustered the courage to move ahead and face the world. Now, she is the Vice President of Growth at growth advisory firm Bionic. She also authors several books, co-hosts a podcast and speaks about entrepreneurship, failure and women in technology.

Evan Williams

Blogger, Medium and Twitter are hits attached to his name, but Evan Williams also had some misses with Odeo and Pyra Labs. The silver lining was that Twitter and Blogger were side projects of these failed ventures, offshoots that became huge successes even when the companies folded. Blogger was eventually acquired by Google and Williams recently stepped down from Twitter’s board to focus on Medium, but his works continue to grow and bring more successes.

Kathryn Minshew

After spending sleepless nights and working weekends establishing and building PYP Media with three other co-founders, Kathryn Minshew lost everything, including her life savings, due to disagreements with the other founders. Out of that major bump in her entrepreneurial journey, which caused too much pain on her, Minshew and her co-founder Alexandra Cavoulacos went on to start The Muse, a career development platform and now have been helping people on their careers.

Ruth Fertel

With a need to earn more to finance her sons’ college education, Ruth Fertel acquired a restaurant for sale that she found on a newspaper ad. Despite not having any experience in running an eatery, Ruth went on to mortgage her house to purchase Chris’ Steak House in New Orleans. But Hurricane Betsy caused damage and power outages in her place, which prompted Fertel to cook and serve her perishable products to the community. Then, the steakhouse caught fire. As she had to transfer to a new location, she couldn’t keep the original name of the restaurant, so she added her name before it, making it Ruth’s Christ Steak House. And the rest, as they say, is history.

Mark Cuban

He may be considered a maverick in the entrepreneurial field, but Mark Cuban had to endure several failures in business, from selling garbage bags and powdered milk to setting up a bar, before he started tasting the sweet flavour of success. Still, there were hiccups along the way, yet those difficulties helped shape Cuban to become a lucrative businessman who owns NBA’s Dallas Mavericks, AXS TV, Magnolia Pictures, Three Commas, Dropbox, and several other companies.

Natalie Ellis

Natalie Elizabeth Ellis is the one part of the duo behind BossBabe, an online movement of women for women. But before she co-founded her BossBabe company with Dr Danielle Canty, Ellis was already on her entrepreneurial journey at a young age, selling candy floss and later on starting her digital marketing consultancy and a company selling detox superfood supplements. But this young serial entrepreneur also had her string of frustrations. In one of her earlier ventures, she experienced some disparities in a business partnership that led to its dissolution, which has caused her so much stress but also taught her valuable lessons. She realised that she went through that route because she wasn’t confident enough to do it all by herself. That led her to believe in herself more, making her what a BossBabe truly is.

Rowland Hussey Macy, Sr.

Named after its founder, Rowland Hussey Macy, Macy’s is one of the biggest and most popular retail stores in the US. At 22, Macy opened a needle-and-thread store in Boston which later closed shop. Two years after, he built a dry goods store and suffered almost the same fate as his first venture. Undaunted, he went on and partnered with his brother to open another dry goods store. The success was not astounding and only short-lived. Macy left and headed to New York City where he opened his own dry goods store -- R.H. Macy & Co. And that’s how Macy’s started and continued its rise, which would have not been possible if not for the persistence of its founder.

Countless more business owners have dealt with failures during their entrepreneurial journey. You’ll hear some of them from EO Members themselves. Still, they kept going and many of them have made breakthroughs and reached milestones in their businesses and careers. It goes to show that when you are determined and persistent about attaining your vision and you put your heart and mind into it, the possibilities can be limitless. Failures are inevitable, but if you embrace them and use them as tools for your journey, you will eventually reach the peak of success.