{"id":1423,"date":"2026-06-14T22:09:27","date_gmt":"2026-06-14T22:09:27","guid":{"rendered":"https:\/\/crosscountrymovingteams.com\/?p=1423"},"modified":"2026-06-14T22:09:27","modified_gmt":"2026-06-14T22:09:27","slug":"kevin-oleary-says-being-liked-has-nothing-to-do-with-success-steve-jobs-taught-him-you-cant-worry-about-whose-feelings-you-bruise","status":"publish","type":"post","link":"https:\/\/crosscountrymovingteams.com\/?p=1423","title":{"rendered":"Kevin O\u2019Leary says being liked has nothing to do with success\u2014Steve Jobs taught him: \u2018You can\u2019t worry about whose feelings you bruise\u2019"},"content":{"rendered":"
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\u201cI don\u2019t think people you work with need to be your friends,\u201d O\u2019Leary told Fortune<\/em> last year. \u201cThey have to respect you, and you have to lead them forward on their careers, make them money, and help them achieve their goals.\u201d<\/p>\n

Read more Prices for whey protein ingredients are up as much as 250% on U.S. dairy\u00a0commodities markets as demand soars<\/a><\/p>\n

O\u2019Leary, the so-called Mr. Wonderful, doesn\u2019t feel the need to play nice or sugarcoat his opinions, and it may be part of the reason why he\u2019s 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\u2019s educational software. O\u2019Leary Ventures, his venture capital firm, has also backed dozens of startups including sustainable company Blueland\u2014which eclipsed $300 million in lifetime sales last November\u2014and $14.5 million photo printing app Groovebook.\u00a0<\/p>\n

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Scoring a deal with Mr. Wonderful on Shark Tank <\/em>and beyond is no easy venture\u2014he\u2019s known as a quick-witted, bold, and demanding business investor. And he isn\u2019t afraid to ruffle some feathers, as he\u2019s embodied a \u201cfounder\u2019s mindset\u201d 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\u2019s a leadership strategy he observed from Jobs in the 1990s, who often disregarded feelings in order to ensure his business partnerships thrived. O\u2019Leary knows he needs to crack a few eggs to make an omelet\u2014even if it means not being popular.\u00a0<\/p>\n

\u201cI don\u2019t spend a lot of time on likability, I don\u2019t care about that. It seems so irrelevant. If you spend your time worrying about that, you\u2019re going to fail for sure, because you\u2019re going to miss the signal,\u201d O\u2019Leary continued.\u00a0<\/p>\n

\u201cThe signal is not having everybody like you\u2014that has nothing to do with success\u2026You can\u2019t worry about whose feelings you bruise. You\u2019ve got to get it done.\u201d<\/p>\n

Working with Jobs and leading with tough love: \u2018You\u2019re gonna deal with it anyways\u2019<\/h2>\n

Silicon Valley CEOs aren\u2019t known to be the most friendly or personable, and the late tech mogul Jobs was no exception to that rule.\u00a0<\/p>\n

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While SoftKey was working with Apple in creating new educational software, O\u2019Leary 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\u2019t matter, and that the programs would work best under Jobs\u2019 direction.\u00a0<\/p>\n

\u201cOver time, you want to be part of that momentum, because you\u2019re on the winning team. We made a lot of money with Steve Jobs, he was right. \u2018You make the software, I\u2019ll deliver the market. Just go do it right.\u2019 I listened to him, and he was right.\u201d<\/p>\n

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O\u2019Leary noted that it\u2019s 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\u2019s worked with, including Jobs, aren\u2019t hung up on being enjoyable.\u00a0<\/p>\n

Read more Vietnam has bold plans for its economic future. It will need U.S. tech, capital, and speed to make them happen<\/a><\/p>\n

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\u201cI don\u2019t think that\u2019s certainly how Jobs operated, and so I don\u2019t spend a lot of time worrying about that stuff,\u201d O\u2019Leary said. \u201cI know a lot of people don\u2019t like me because I\u2019m blunt and I tell the truth\u2014I don\u2019t really care. It\u2019s the truth today, it\u2019s the truth next week, it\u2019s the truth in six months. You\u2019re gonna deal with it anyways.\u201d<\/p>\n

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Moments Jobs proved his success required ruling with an iron fist\u00a0<\/h2>\n

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\u2019s interface. The devil is in the details\u2014and now there are more than 100 million Macs in use.\u00a0<\/p>\n

\u201cIt created a high-pressure environment,\u201d Chris Neck, professor of management at Arizona State University, wrote on Jobs\u2019 intense leadership style. \u201cHe pushed the original Mac team with impossible deadlines, often clashing with engineers but producing a revolutionary product.\u201d 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.<\/p>\n

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 <\/em>and Toy Story <\/em>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\u2019t optional with Jobs on the other end of the line.<\/p>\n

\u201cHe would call\u2014especially the producers\u2014at any time, day or night, three in the morning, you\u2019re on vacation, doesn\u2019t matter,\u201d Pete Docter, chief creative officer at Pixar who formerly worked under Jobs, said at Fast Company<\/em>\u2019s Most Innovative Companies Gala in 2025. \u201cHe wants to talk to you about it, you\u2019re on.\u201d<\/p>\n

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O\u2019Leary told Fortune<\/em> that he thought Jobs\u2019 leadership style was \u201csomething else\u201d\u2014but he admired how he was able to command teams, keep his eye on the prize, and stay in that \u201csignal\u201d mode. It\u2019s a mindset and strategy that\u2019s infectious to work with, he says.\u00a0<\/p>\n

\u201cI\u2019m not saying I liked him that much, but damn, I respected him. Because he had incredible execution skills. He could say, \u2018I\u2019m going to get from here to there, and get it done.\u2019 He didn\u2019t give a damn who got in his way,\u201d O\u2019Leary reminisced.<\/p>\n

Read more Gen Z grad landed an internship by wearing her university baseball cap to her pizza joint job. Now she works at Cisco<\/a><\/p>\n

A version of this story was published on Fortune.com on August 10, 2025.<\/em><\/p>\n<\/div>\n","protected":false},"excerpt":{"rendered":"

Multimillionaire investor Kevin O\u2019Leary says the late Apple cofounder taught him \u201cyou’re going to fail for sure” if you worry about being liked.\u201d<\/p>\n","protected":false},"author":1,"featured_media":1422,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[263],"tags":[],"class_list":["post-1423","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-steve-jobs"],"yoast_head":"\nKevin O\u2019Leary says being liked has nothing to do with success\u2014Steve Jobs taught him: \u2018You can\u2019t worry about whose feelings you bruise\u2019 - Cross Country Moving Team<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/crosscountrymovingteams.com\/?p=1423\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Kevin O\u2019Leary says being liked has nothing to do with success\u2014Steve Jobs taught him: \u2018You can\u2019t worry about whose feelings you bruise\u2019 - 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