Kevin O’Leary, famed for his blunt on-screen persona as Shark Tank’s Mr. Wonderful, says leadership isn’t about being beloved by every teammate. In a candid discussion with Fortune, the billionaire entrepreneur credits much of his hard-edged approach to the example set by Apple cofounder Steve Jobs—and to a leadership philosophy that prizes respect and rapid, results-driven progress over niceties.
“I don’t think people you work with need to be your friends,” O’Leary says. “They have to respect you, and you have to lead them forward on their careers, make them money, and help them achieve their goals.” His forthright stance, he notes, has helped him build a $400 million fortune, including a pivotal moment in 1999 when SoftKey Software Products was sold to Mattel for $4.2 billion. That deal came after his collaboration with Jobs on Apple’s educational software, a partnership that helped fuel both his investing approach and his belief in ruthless execution.
Beyond SoftKey, O’Leary’s venture capital firm, O’Leary Ventures, has backed more than 80 startups. Among them are Blueland, a sustainable company that has surpassed $100 million in lifetime sales, and Groovebook, a mobile photo printing app that drew about $14.5 million in funding. The path to success, he asserts, hinges on a founder’s mindset: to identify the three to five most crucial tasks and push through the noise to get them done quickly.
“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,” he adds. “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.”
Jobs’ leadership style is remembered for its intensity as well. While SoftKey was collaborating with Apple on educational software, O’Leary recalls, he urged Jobs to listen to teachers and students. Jobs, however, believed the direction should come from him, and the partnership ultimately thrived on that conviction. “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 emphasizes that receiving respect matters more than being universally liked. His own leadership philosophy centers on guiding partners toward greater achievement and financial reward, a stance that can involve tough-love moments. “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,” he reflects on Jobs.
Jobs’ impact wasn’t limited to Apple. As a cofounder of Pixar after purchasing it from Lucasfilm in 1986, he imposed demanding schedules that produced landmark films like Finding Nemo and Toy Story. Pixar veterans recount the relentless pace, including calls at odd hours, that reflected Jobs’ insistence on keeping projects on track. Pete Docter, Pixar’s chief creative officer, recalled, “He would call—especially the producers—at any time, day or night, three in the morning, you’re on vacation, doesn’t matter.” Yet that same discipline helped shape a studio that would redefine modern animation.
The respect O’Leary feels for Jobs stems from the Apple cofounder’s ability to stay focused on the prize and deliver results. “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 says.
What this means for leaders today
– Emphasize results and clear accountability: define a few crucial priorities and push aggressively to complete them.
– Prioritize respect and straight talk over popularity: blunt, honest feedback can be essential for progress, as long as it’s anchored in outcomes.
– Balance high standards with organizational impact: tough leadership can drive innovation and market success, but be mindful of preserving critical talent and avoiding burnout.
– Learn from legendary examples but adapt to your context: Jobs’ execution mindset is a powerful model, but leaders should tailor their approach to fit their teams and industries.
Summary
Kevin O’Leary credits his no-nonsense leadership ethos to mentors like Steve Jobs, emphasizing respectful, results-driven guidance over popularity. From SoftKey’s blockbuster sale to his VC investments in Blueland and Groovebook, his approach—rooted in “signal” over noise—reflects a broader legacy of tough, ruthless execution that has helped him build a substantial fortune and influence. The enduring lesson for today’s leaders is to couple rigorous accountability with strategic focus, while staying true to a core commitment to delivering tangible outcomes.
Editor’s note: This piece highlights the leadership dynamics between two iconic tech figures. For readers, it offers practical takeaways on balancing candor with strategy in high-pressure environments.