‘Shark Tank’s’ Mark Cuban Reveals One of His Biggest Mistakes

Billionaire Mark Cuban of ABC’s  Shark Tank wears many hats. With titles that include tech guru, film producer, reality star, and owner of the Dallas Mavericks, Cuban clearly knows how to work hard and achieve success.

Yet despite his apparent business smarts, Cuban has made his share of mistakes, including this one opportunity that could have reaped him a windfall.

“Shark Tank’s” Mark Cuban | Jason Mendez/Getty Images

Putting in the time

Cuban’s success can be attributed to his strong work ethic. “My days are straight out of the movie Groundhog Day. I wake up, check my email, news feeds and eat. I kiss my wife and kids, and get them to school,” he told Entrepreneur in 2012. “I come home and get back in front of my computer. I’ll go workout. I’ll play with the kids when they come home.”

The tech guru’s day doesn’t end there, where he continues to clock in until it’s time for some shut eye. “I’ll sit in front of my computer some more. If there is a Mavs game I check my email at breaks and go to my computer at halftime,” Cuban said. “After the game, I do the same thing until I go to bed.”

Cuban will often tell aspiring business owners entering the tank that they have to be willing to put in the time if they want an investment from him. Talking to YouTube channel Valuetainment in 2015, Cuban said that the number one reason people fail in business is “lack of brains [and] lack of effort. They don’t do the work,” he said.

The one that got away

When Uber was beginning to hit the road, Cuban was asked to invest by co-founder and former CEO Travis Kalanick. He had already invested in Kalanick’s first start-up, Red Swoosh, a peer-to-peer file sharing company that wasn’t too successful, so the Shark Tank star was hesitant on the new venture.

“You are going to have to fight all the taxi associations, and all the transportation organizations in each city and every state,” Cuban said, according to CNBC. “Then I started talking to him about his valuation, and I never heard back from him. The rest is history.”

Now that Uber is worth billions, Cuban considers missing out on the ground floor to be one of his biggest mistakes. “The point is, when you are trying to disrupt something like Travis was doing, sometimes you have got to be ready, fire, aim and just bust through doors and figure you will deal with the regulatory issues later,” he shared.

Hindsight is always 20/20

Cuban realizes that he was too shortsighted at the time, saying Kalanick “has obviously disrupted transportation, and he’s trying to do a whole lot more than that, and he gets all the credit because where I saw regulation, he ignored it.”

The reality star has learned from his past mistakes and is determined not to repeat them. “If you really believe and you really have something that you think is going to disrupt the world, bring it to me,” he told CNBC. “I won’t make the same mistake twice, and then just go and bust through those doors and figure out how to get through the hurdles.”

View this post on Instagram

Crushed but oddly satisfied :)

A post shared by Mark Cuban (@mcuban) on

While he may regret passing on the billion-dollar business, Cuban doesn’t let failure keep him down. “It doesn’t matter how many times you fail,” Cuban said, according to Moneywise. “Each time only makes you better, stronger, smarter.”