“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.”

O’Leary says his favorite example was when he wanted to go into the watch insurance business a few years ago. Some detractors argued that it was “impossible” for him to succeed in the hyperniche space, that he wouldn’t even be able to break in. But in April 2024, O’Leary announced that he would be launching a watch insurance platform called WonderCare. 

His haters turned out to be great motivators, and with over 40 years of skin in the game, O’Leary isn’t easily deterred by a snide comment or occasional failure. A part of that attitude also rests on his “founder’s mindset” that he learned by working with the late Apple cofounder Steve Jobs in the 1990s: being able to tune out the “noise” of critics or external pressures, and focus on the “signal” of getting the day’s three to five most important things done straight away.

“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.”

The founder’s mindset: leading with signal, and tuning out the noise

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. 

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.”