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5 entrepreneurs reveal their biggest regrets over missed opportunities, mistakes

Posted by Shivali Anand

November 19, 2021    |     4-minute read (723 words)

Any successful entrepreneur will admit that they overcame obstacles along their journey. Sometimes those adversities precipitated a breakthrough, but in some cases, those challenges became a source of regret. 

Here’s a recap of what five well-known entrepreneurs have divulged about mistakes and missed opportunities along their way to success. Perhaps this can help fellow entrepreneurs currently building their own ventures to avoid making the same mistakes — or to reconsider an obstacle they currently face. 

NBA phenom Magic Johnson 

When basketball legend and entrepreneur Magic Johnson first joined the NBA at age 19, he was flooded with sponsorship opportunities. While he knew he wanted to work with a shoe brand, he didn't know enough about finance to contemplate accepting a stock agreement versus a cash one, which led to a decision he now regrets. 

"Converse came in and offered me some money," Johnson said. "And then this guy named Phil Knight came in, and Nike was only like one or two years old. He said he doesn't have a lot of money but will offer me stock." 

Johnson accepted the financial offer from Converse and has reflected on it several times since. "Boy, did I make a mistake? I'm still kicking myself," he said. "Every time I'm in a Nike store, I get mad. I could've been making money off of everybody buying Nikes right now."

Wendy’s founder Dave Thomas

Wendy's creator Dave Thomas started the hamburger business in 1969 after years of working for Colonel Sanders, the founder of KFC. That connection led him to believe that his new enterprise should also have a personality linked with it. But later, Thomas said that he regretted his decision to model the iconic Wendy’s character on his own daughter, Wendy.

"Before my father left us, we had a long discussion about him naming the business Wendy's. He said, 'You know what? I'm sorry.' I asked him what he meant. He explained, 'I should've just named it after myself because it put a lot of pressure on you,’" Wendy Thomas remarked.

Entrepreneur and TV personality Mark Cuban

Throughout his career, the Broadcast.com creator and “Shark Tank” investor Mark Cuban has invested in a slew of both profitable and unsuccessful enterprises. But there was one investment pitch he turned down that went on to become one of his biggest regrets. 

When Uber founder Travis Kalanick approached him with the concept for the ride-sharing firm, instead of investing, Cuban pointed out the challenges that Kalanick would face if he pursued it further. "You are going to have to fight all the taxi associations and all the transportation organizations in each city and every state," Cuban told him. 

Cuban subsequently understood that instead of withholding his investment, he should have known better than to question an entrepreneur's ability to overcome such obstacles.

Producer, talk show host and author Oprah Winfrey

Winfrey sought to make her TV network OWN an industry game-changer after the success of her eponymous talk show, which remained at the top of its game for years. Her aspirations for OWN did not come to fruition, Winfrey said, because there were an overwhelming number of seemingly insurmountable glitches to smooth out.

"Had I known it was this difficult, I might have done something else," she told “CBS This Morning” in a 2012 interview. Her greatest regret? Releasing the OWN network before it was ready, which she likened to having a wedding before you're ready.

Microsoft magnate Bill Gates

Microsoft co-founder Bill Gates may have built a wildly successful computer empire, but the experience has not been one absent of misgivings over missed opportunities. In particular, he mentions the major product category he regrets not understanding more deeply: mobile phones.

"In the software world, particularly for platforms, these are winner-take-all markets. So the greatest mistake ever is whatever mismanagement I engaged in that caused Microsoft not to be what Android is," Gates said in 2019. 

"That is, Android is the standard non-Apple phone platform. That was a natural thing for Microsoft to win. It really is winner take all. If you're there with half as many apps or 90% as many apps, you're on your way to complete doom. There's room for exactly one non-Apple operating system and what's that worth? $400 billion that would be transferred from company G to company M."

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