“I don’t think people you work with need to be your friends,” O’Leary told Fortune last year. “They have to respect you, and you have to lead them forward on their careers, make them money, and help them achieve their goals.”

O’Leary, the so-called Mr. Wonderful, doesn’t feel the need to play nice or sugarcoat his opinions, and it may be part of the reason why he’s amassed a $400 million fortune through his business success. The serial investor made a big splash in 1999 when he sold his business SoftKey Software Products to Mattel for $4.2 billion, just after working with Jobs on developing Apple’s educational software. O’Leary Ventures, his venture capital firm, has also backed dozens of startups including sustainable company Blueland—which eclipsed $300 million in lifetime sales last November—and $14.5 million photo printing app Groovebook. 

Scoring a deal with Mr. Wonderful on Shark Tank and beyond is no easy venture—he’s known as a quick-witted, bold, and demanding business investor. And he isn’t afraid to ruffle some feathers, as he’s embodied a “founder’s mindset” that prioritizes signal over noise. That means being able to get three to five of the most important things done quickly, while drowning out outside chaos and distractions. It’s a leadership strategy he observed from Jobs in the 1990s, who often disregarded feelings in order to ensure his business partnerships thrived. O’Leary knows he needs to crack a few eggs to make an omelet—even if it means not being popular. 

“I don’t spend a lot of time on likability, I don’t care about that. It seems so irrelevant. If you spend your time worrying about that, you’re going to fail for sure, because you’re going to miss the signal,” O’Leary continued. 

“The signal is not having everybody like you—that has nothing to do with success…You can’t worry about whose feelings you bruise. You’ve got to get it done.”

Working with Jobs and leading with tough love: ‘You’re gonna deal with it anyways’

Silicon Valley CEOs aren’t known to be the most friendly or personable, and the late tech mogul Jobs was no exception to that rule. 

While SoftKey was working with Apple in creating new educational software, O’Leary had suggested that Jobs hear what teachers and students want from the games. But the Apple cofounder was having none of it, stating their opinions didn’t matter, and that the programs would work best under Jobs’ direction. 

“Over time, you want to be part of that momentum, because you’re on the winning team. We made a lot of money with Steve Jobs, he was right. ‘You make the software, I’ll deliver the market. Just go do it right.’ I listened to him, and he was right.”

O’Leary noted that it’s more important to be respected than well-liked. His leadership strategy revolves around leading his business partners forward in their careers, making them lots of money, and helping them achieve their goals. It might require some tough love, but the most successful people he’s worked with, including Jobs, aren’t hung up on being enjoyable. 

“I don’t think that’s certainly how Jobs operated, and so I don’t spend a lot of time worrying about that stuff,” O’Leary said. “I know a lot of people don’t like me because I’m blunt and I tell the truth—I don’t really care. It’s the truth today, it’s the truth next week, it’s the truth in six months. You’re gonna deal with it anyways.”

Moments Jobs proved his success required ruling with an iron fist 

Jobs was well-known for creating tense work environments, but after all, diamonds are made under pressure. As a perfectionist who loved to micromanage his employees, even the smallest perceived error could have resulted in a tirade. For instance, staffers on his Macintosh team were once berated for having improper spacing in the system’s interface. The devil is in the details—and now there are more than 100 million Macs in use. 

“It created a high-pressure environment,” Chris Neck, professor of management at Arizona State University, wrote on Jobs’ intense leadership style. “He pushed the original Mac team with impossible deadlines, often clashing with engineers but producing a revolutionary product.” Neck noted that this abrasive approach lost Apple some key talents, such as Macintosh computer designer Jef Raskin, who decided to leave the company in 1982.

Even when Jobs was pursuing other projects outside of Apple, he had that same trademark intensity. Jobs was one of the three founding fathers of Pixar Animation Studios, after having purchased the group from LucasFilm in 1986. But to get iconic films like Finding Nemo and Toy Story off the page and onto movie screens worldwide, he put staffers under an intense work schedule. No one wants to be woken up to their boss calling them at 3 a.m., but picking up the phone wasn’t optional with Jobs on the other end of the line.

“He would call—especially the producers—at any time, day or night, three in the morning, you’re on vacation, doesn’t matter,” Pete Docter, chief creative officer at Pixar who formerly worked under Jobs, said at Fast Company’s Most Innovative Companies Gala in 2025. “He wants to talk to you about it, you’re on.”

O’Leary told Fortune that he thought Jobs’ leadership style was “something else”—but he admired how he was able to command teams, keep his eye on the prize, and stay in that “signal” mode. It’s a mindset and strategy that’s infectious to work with, he says. 

“I’m not saying I liked him that much, but damn, I respected him. Because he had incredible execution skills. He could say, ‘I’m going to get from here to there, and get it done.’ He didn’t give a damn who got in his way,” O’Leary reminisced.

A version of this story was published on Fortune.com on August 10, 2025.