'Shark Tank' Star Kevin O'Leary's Main Motivation Is Proving His Haters Wrong, Not Making Money

"Shark Tank" investor Kevin O'Leary has a simple secret for staying motivated: he loves proving people wrong. "I just love it when people tell me, ‘Oh, you can't do this, you can't do that,'" O'Leary recently told Fortune.

 "When someone tells me I can't do it, I turn around, two years later, kick their ass," he continued. "That's a great motivation. It's not about the money anymore—I just like kicking their ass." O'Leary shot to fame on "Shark Tank," where his tough negotiating style and his acerbic wit earned him the nickname "Mr. Wonderful." 

Whether you love him or hate him, it's impossible to deny that O'Leary is a successful businessman with a keen eye for investing and potential profit opportunities. He made his fortune by starting his own company, SoftKey Software Products, and then selling it for $3.7 billion. 

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Most people would be happy to ride off into the sunset and enjoy a life of leisure after making that kind of money, but O'Leary is not like most people. He relishes the idea of developing new businesses and moving into different industries. O'Leary told Fortune that his expansion into new fields often precedes a spate of "industry experts" and haters to offer their opinions on why his new venture can't work.

For O'Leary, that's like waving a red flag in front of a bull. His entry into the watch insurance industry is his favorite case of proving his doubters wrong.  He said some people went so far as to tell him it would be "impossible" for him to get his business off the ground and that the field was "too niche" to accommodate a new player. Despite that, O'Leary launched his WonderCare watch insurance business in April 2024.

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Although O'Leary has a wildly successful track record as a businessman, it doesn't mean he hasn't experienced setbacks or made bad investments. He sees it as part of the process. "I'm fairly lucky. I've made lots of mistakes investing," he told Fortune. "But I've also had extraordinary outcomes. I'm not scared to fail. I've never bet the farm on anything."

O'Leary said he views having a "founder's mindset" as a key element of his success as a businessman and entrepreneur. He says he developed this mindset while working with Apple (NASDAQ: AAPL) co-founder Steve Jobs in the late 1990s. O'Leary noticed that Jobs was always laser-focused on his own vision and had a unique ability to block out external “noise." He also concedes that it took time and effort to develop that trait in himself. 

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"I've had to work on it, because I didn't even know that was important till I went through my whole thing with Jobs way back in the early 90s," O'Leary said. "But I also deal with it in every aspect of what I'm doing…[If] business is biting, you focus on making money or losing money." O'Leary's sustained success in business would seem to suggest that he has mastered this mindset.

That's not to say that O'Leary doesn't take time to stop and smell the roses. He has pursuits outside of making money that help keep him centered. "I also have interest in photography, in watch collecting, guitar collecting, guitar playing, all kinds of things that I focus on to balance where my head is at," he told Fortune. "To keep the creative yin and yang."

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