Kevin O’Leary says being liked has nothing to do with success—Steve Jobs taught him: ‘You can’t worry about whose feelings you bruise’
CEOs take on all sorts of personas, from the benevolent leader to the cutthroat business executive. Millionaire entrepreneur Kevin O’Leary is famous for his brutally honest, intimidating aura on-screen as a Shark Tank investor—and some of that leadership style rubbed off on him from working with the late Apple cofounder Steve Jobs. “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, youR