“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.”
