5 Times Famous Entrepreneurs Expressed Their Regrets

Posted by Ruby Sahiwal

4-minute read (800 words)

Ask any entrepreneur about their successes, and they’re sure to mention that they encountered challenges along the way, which can sometimes lead to breakthroughs, and may in other cases lead to regret.

Check out what the following five well-known entrepreneurs have said about the regrets they have about the past so you can learn from their mistakes.

Bill Gates

The Microsoft cofounder built a computer empire, but that doesn’t mean he lives his life without regrets. In fact, he refers to one big product line that he wishes he had mastered better — the mobile phone.

“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,” he said last year. “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 percent 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.”

Oprah Winfrey

After building a talk show empire that remained at the top of its game for years, Winfrey aimed to establish her television network OWN as a game-changer, but there were many kinks that needed to be worked out along the way, she said.

In fact, she told CBS This Morning in 2012, “Had I known it was this difficult, I might have done something else.” The biggest regret she had was launching the network before it was completely ready, which she likened to getting married before being totally prepared for it.

Dave Thomas

When the Wendy’s founder launched the hamburger chain in 1969, he did so after having worked for KFC founder Colonel Sanders for years, which led him to believe the company should have a character to associate with the brand. What he regretted, he later said, was basing that character on his own daughter, who was named Wendy.

"Before my dad left us, we had a long conversation about him naming the restaurant Wendy’s,” Wendy Thomas said. “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.'"

Mark Cuban

The Broadcast.com founder and Shark Tank investor has invested in both money-making and money-losing ventures during his long career, but it’s one investment he didn’t make that he considers to be among his biggest regrets.

He was approached by Uber founder Travis Kalanick when the idea for the ride-sharing company was first floated, and instead of investing, Cuban pointed out the headwinds that Kalanick would face if he continued on with the idea. “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. He realized later that he should have known better than to have doubted an entrepreneur’s ability to break through such types of hurdles rather than having withheld his investment dollars.

Magic Johnson

The basketball great and entrepreneur was just 19 years old when he joined the NBA and started getting endorsement offers. Although he knew he wanted to make a deal with a sneaker company, he didn’t know enough about investing to consider taking a stock deal rather than a cash offer, which he now regrets.

“Converse came in and offered me some money,” he 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 took the cash offer with Converse and has thought about it many times since then. “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.”

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