Kevin O’Leary Turns Criticism into $3.7 Billion Success

Kevin O’Leary, the renowned investor from the popular television series "Shark Tank," has shared his unique perspective on motivation and success. O’Leary, who has built a multimillion-dollar empire through various business ventures, including software, insurance, and investment platforms, has revealed that his primary motivation comes from those who doubt his abilities. He finds that the criticism and skepticism from naysayers fuel his drive to succeed, often leading him to prove them wrong.

O’Leary’s journey to becoming a business icon spans over four decades. From his iconic role as "Mr. Wonderful" on "Shark Tank" to founding and selling his company SoftKey Software Products for $3.7 billion, his career is marked by significant achievements. Despite his success, O’Leary remains motivated by the challenges posed by critics who believe he cannot break into new industries. He views these challenges as opportunities to demonstrate his capabilities and resilience.

“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.” This mindset was evident when he ventured into the watch insurance business. Despite detractors arguing that it was an impossible niche for him to succeed in, O’Leary launched WonderCare, a watch insurance platform, in April 2024. This achievement underscores his ability to turn criticism into motivation and success.

O’Leary’s approach to business is deeply influenced by his "founder’s mindset," a concept he learned from working with the late Steve Jobs in the 1990s. This mindset involves tuning out external noise and focusing on the most important tasks at hand. Jobs, known for his leadership style, was able to maintain an 80% signal to 20% noise ratio, which O’Leary has adopted in his own business practices. This balance allows him to stay focused on his goals while also engaging in personal interests such as photography, watch collecting, and guitar playing.

O’Leary says the “founder’s mindset” is a key ingredient in the entrepreneurial success he witnessed while working with Jobs. 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. O’Leary saw his leadership style as brutal—but respected how Jobs was able to keep his eye on the ball, dubbed “signal” mode. Meanwhile, he was able to drown out the “noise” of everyday life and external opinions to stick with the game plan. O’Leary says Jobs struck a good balance of 80% signal, to 20% noise. He says he’s also reached that dynamic of 80:20, striking a balance between business and hobbies to keep himself dynamic. Meanwhile, he says others like Tesla CEO Elon Musk lead completely with 100% signal.

“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.”

O’Leary’s philosophy is not just about financial success but also about personal fulfillment. He believes that maintaining a balance between business and personal interests is crucial for long-term success. This approach has helped him navigate the challenges of entrepreneurship and maintain a dynamic and creative mindset. O’Leary’s story serves as an inspiration for aspiring entrepreneurs, highlighting the importance of resilience, focus, and the ability to turn criticism into motivation.