CEOs take on the most diverse profiles, from the benevolent leader to the ruthless executive. Millionaire entrepreneur Kevin O’Leary is famous for his brutally honest and intimidating on-camera stance as an investor on the show Shark Tank — and part of that leadership style was influenced by his experience working with the late Apple co-founder Steve Jobs.
“I don’t think the people you work with need to be your friends,” O’Leary told Fortune last year. “They need to respect you, and you need to help them advance their career, make money, and achieve their goals.”
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O’Leary, known as Mr. Wonderful, doesn’t feel the need to be nice all the time or soften his opinions, and that may be part of the reason he’s amassed a $400 million fortune thanks to his business success.
The serial investor gained notoriety in 1999 when he sold his company, SoftKey Software Products, to Mattel for $4.2 billion, shortly after working with Jobs to develop Apple’s educational software.
His venture capital firm O’Leary Ventures has also invested in dozens of startups, including sustainable company Blueland — which surpassed $300 million in cumulative sales last November — and photo printing app Groovebook, acquired for $14.5 million.
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Getting a deal with Mr. Wonderful, whether on Shark Tank or off, is no easy task — he is known for being a quick-witted, bold and demanding investor. And it’s not afraid of upsetting some people, as it adopts a “founder’s mentality” that prioritizes signal over noise.
This means being able to quickly perform three to five fundamental tasks, ignoring chaos and external distractions. It’s a leadership strategy he observed in Jobs in the 1990s, when the businessman often put feelings aside to ensure the success of his business partnerships.
O’Leary knows you have to break a few eggs to make an omelet — even if it means it’s not popular.
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“I don’t spend a lot of time thinking about being liked, I don’t care about that. It seems like a totally irrelevant thing. If you spend your time worrying about that, you’re bound to fail, because you’re going to miss what really matters,” O’Leary continued.
“What really matters is not making everyone like you — that has nothing to do with success… You can’t worry about hurting sensibilities. You have to do the work.”
Silicon Valley CEOs aren’t known for being the friendliest or most charismatic people, and the late tech mogul Jobs was no exception.
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As SoftKey worked with Apple to create new educational software, O’Leary suggested that Jobs listen to teachers and students about what they wanted in games. But Apple’s co-founder was cool with the idea, saying their opinions didn’t matter and that the programs would work better under his own direction.
“Over time, you want to be part of this movement, because you’re on the winning team. We made a lot of money under Steve Jobs, and he was right. ‘You guys do the software, I’ll deliver the market. Just do it right.’ I listened to him, and he was right.”
O’Leary noted that it is more important to be respected than liked. His leadership strategy revolves around boosting his business partners’ careers, making them earn lots of money, and helping them achieve their goals.
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This may require some firmness, but the most successful people you’ve worked with, including Jobs, don’t get caught up in the need to please.
“That’s certainly not how Jobs worked, so I don’t spend a lot of time worrying about those things,” O’Leary said. “I know a lot of people don’t like me because I’m direct and I tell the truth—and I don’t really care. It’s true today, it’ll be true next week, and it’ll still be true six months from now. You’re going to have to deal with it anyway.”
Moments when Jobs showed that his success required an iron fist
Jobs was widely known for creating tense work environments, but after all, diamonds are formed under pressure. A perfectionist and adept at micromanagement, even the smallest perceived error could trigger a reprimand.
For example, members of the Macintosh team were once reprimanded for inadequate spacing in the system’s interface. The details make all the difference — and today there are more than 100 million Macs in use.
“This created a high-pressure environment,” wrote Chris Neck, a management professor at Arizona State University, about Jobs’ intense leadership style.
“He pushed the original Mac team to impossible deadlines, often clashing with engineers but making a revolutionary product.”
Neck noted that this more aggressive approach cost Apple some key talent, such as Macintosh designer Jef Raskin, who decided to leave the company in 1982.
Even when Jobs dedicated himself to projects outside of Apple, he maintained the same characteristic intensity. Jobs was one of the three founders of Pixar Animation Studios, after acquiring the group from Lucasfilm in 1986.
But, to transform iconic films such as Finding Nemo and Toy Story into global successes, he subjected employees to an intense work routine. No one wants to be woken up by their boss at three in the morning, but answering the phone wasn’t optional when there was a call from Jobs on the other end of the line.
“He would call — especially the producers — at any time, day or night, at three in the morning, during his vacation, it didn’t matter,” said Pete Docter, Pixar’s chief creative officer and former Jobs subordinate, during Fast Company’s 2025 Most Innovative Companies event. “He wanted to talk about it, so you answered.”
O’Leary told Fortune that he considered Jobs’ leadership style to be unusual—but he admired his ability to command teams, keep his eyes on the goal, and stay focused on the “signal.” According to him, this is a contagious mentality and strategy for anyone who works alongside someone like this.
“I’m not saying I liked him that much, but, damn, I respected him. Because he had incredible execution ability. He could say, ‘I’m going to get from here and I’m going to get there, and I’m going to do it.’ He didn’t care if anyone got in his way,” O’Leary recalled.
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