Entrepreneurs Who Bounced Back From Failure To Something Bigger

Updated on 12 October 2017

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Learn From These Entrepreneurs Who Bounced Back From Failure To Something Even Bigger


Imagine being fired by an important client or watching your startup take a nose-dive.

That crushing feeling of failure is the reason many entrepreneurs throw in the towel and even more remain ‘want-preneurs‘ never getting off the starting block.

From business icons such as Oprah Winfrey to local entrepreneurship mavericks John Sanei and Miles Kubheka, many have not been immune to failure, what sets these successful entrepreneurs apart, however, is one common trait – they had the tenacity to bounce back from adversity and go on and accomplish even greater things.

Overcoming the odds – These entrepreneurs prove it’s possible to come out on the other side of failure. 


Miles Kubheka is the founder of Vuyo’s Restaurant, author and public speaker.

The Low Moment: Kubheka experienced what he called crushing failure of his first sit-in restaurant in Braamfontein – “made more spectacular by the public glare that surrounded the launch of the brand”, he said during a FuckUp Nights event in Melville.

“More often than not people are not afraid of failing itself, it’s actually what comes with it – the negative stigma, the loss of income. But we need to fail more – if you do more, the chance of failure is more but the chance of success is more as well.”


Dubbed the ‘Oprah Winfrey of Africa’ by CNN, Mo Abudu is a talk show hostess, TV producer, media personality, and entrepreneur/venture capitalist. Abudu is the Executive Chairperson and CEO of Ebony Life TV, Africa’s first Global Black Entertainment and Lifestyle Network.

The Low Moment: In 2006, Abudu approached DStv with the proposal for Moments with Mo, a talk show that was quintessentially African on the DStv bouquet, according to Forbes. She had taken about 5 pilots of the talk show but they were all rejected by DStv. Eventually, her proposal was accepted but was told they were not going to commission, which meant she had to go and look for sponsors, the article states. She did, and the rest, as they say, is history.

“You have to be very passionate about what you do and at the same time, be a business manager, which includes having a solid business plan.”


TV and radio personality and the brains behind energy drink, Mo-Faya.

The Low Moment: DJ Sbu was booted off the Metro FM line up after being suspended by the radio station for promoting his energy drink at the Metro FM Awards in 2015. He also made headlines when he posted on Instagram that he is broke saying that he had had no income for 13 months, had to borrow money from friends and that all his saving was gone.

“The struggle is real fellas. Entrepreneurship is not for the faint hearted, weak and timid. How much are you willing to sacrifice to see your dream become a reality?”


Mark Cuban is the owner of the NBA’s Dallas Mavericks,,co-owner of 2929 Entertainment as well as star investor on ABC’s reality show “Shark Tank”, and author.

The Low Moment: According to an article on Fast Company, Cuban was sleeping on the floor of a tiny apartment in Dallas with five buddies and working as a salesman at a computer store in the early 1980s. He was fired from job after leaving his post and asking a colleague to cover for him to chase an opportunity to close a $15,000 deal.

“I love entrepreneurship because that’s what makes this country grow, and if I can help companies grow, I am creating jobs, I am setting foundations for future generations. It sends the message that the American Dream is alive and well,”


Better known as “Jannie”, Mouton is the founder of the independent financial services group, PSG Group, one of South Africa’s most successful investment companies with stakes in companies such as Capitec Bank, Pioneer Foods, and Distell.

The Low Moment: Mouton started PSG Group after getting fired at age 48, according to entrepreneurship website, How We Made It In Africa. He had been fired by his fellow partners at stockbroking firm Senekal, Mouton & Kitshoff, which he co-founded.But most of all, Mouton says he lost his self-confidence, and admits to having kept his firing a secret from his wife, family and friends.

“It was a shock. I lost my company that I started, and I lost my friends. I was confused and depressed. And then I realised the future is in my hands and in my hands only.”


South African retail giant, Ackerman was chairman of Pick n Pay until he stepped down in 2010. He purchased the Pick ‘n Pay supermarket group from its founder, Jack Goldin, and grew it from four retail outlets to one of South Africa’s largest retail companies.

The Low Moment: In 1966, Ackerman was managing 85 Checkers supermarkets. However, he was fired as MD by the Greatermans group after he opened 89 Checkers stores for them in eight years, according to a Cape Argus article.

“It’s amazing how people can influence you if you’re not big-headed. I’ve got a lot of faults but I’m not big-headed and I’ve listened. These values became absolutely part of my being and why I was really in business.”


John Sanei is a trend specialist, entrepreneur, business innovation strategist and now author.

The Low Moment: At the age of 28, Sanei had made millions after investing in the then hot Primi Piatti restaurant franchise, however, by the age of thirty, he had lost it all, he says according to an SME South Africa article.

“I didn’t adapt to a shape-shifting business environment. And I didn’t adapt because I was not mentally prepared to even comprehend that it was in fact changing. In the rapid-paced, exponentially evolving digital age, this inability to see the wood for the trees is becoming more and more common in business.”


Oprah Winfrey is best known for her talk show The Oprah Winfrey Show. She co-founded the women’s cable television network Oxygen and is also the president of Harpo Productions.

The Low Moment: Before becoming the biggest name in media, Winfrey faced extreme harassment and sexism and was fired as a Baltimore news anchor in her early career. According to an Inc. article, Winfrey told People magazine she had reached her “breaking point” amid criticism over the Oprah Winfrey Network’s low television ratings following its 2011 debut.

“Although there may be tragedy in your life, there’s always a possibility to triumph. It doesn’t matter who you are, where you come from. The ability to triumph begins with you. Always.”

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