Kevin O’Leary has risen to icon status in the business world over his four-decade career. And he’s done it all—from being the iconic “Mr Wonderful” on investor series Shark Tank, to founding and selling his company SoftKey Software Products for $3.7 billion. Through all this success, his huge motivator has been the naysayers who think he can’t break through into new industries.
“I just love it when people tell me, ‘Oh, you can’t do this, you can’t do that,’” O’Leary tells Fortune. “When someone tells me I can’t do it, I turn around, two years later, kick their ass. That’s a great motivation. It’s not about the money anymore—I just like kicking their ass.”
“I’m fairly lucky. I’ve made lots of mistakes in investing, but I’ve also had some extraordinary outcomes…I’m not scared to fail,” he continues. “I never bet the farm on any one thing.”
O’Leary says the “founder’s mindset” is a key ingredient in the entrepreneurial success he witnessed while working with Jobs, which everyone else needs to make it in business.
It was the 1990s, and SoftKey Software Products—later named The Learning Company—was spearheading the development of Apple’s educational software. O’Leary suggested that Jobs hear the input of students and teachers as to what they would want from the program. But Jobs was having none of it, stating their opinions didn’t matter, and that the games would be most successful following the Apple cofounder’s lead.
“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 says. “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.”
“But 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 adds. “To keep the creative yin and yang.”
