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Man who worked for Steve Jobs explains why he ‘wasn’t a nice man’ revealing brutal conversation they had

Home> News> Technology

Published 17:04 24 Aug 2025 GMT+1

Man who worked for Steve Jobs explains why he ‘wasn’t a nice man’ revealing brutal conversation they had

Shark Tank star Kevin O'Leary revealed plenty about the former Apple CEO

James Moorhouse

James Moorhouse

Featured Image Credit: Diary of a CEO

Topics: Steve Jobs, Apple, Business, Elon Musk

James Moorhouse
James Moorhouse

James is a NCTJ Gold Standard journalist covering a wide range of topics and news stories for LADbible. After two years in football writing, James switched to covering news with Newsquest in Cumbria, before joining the LAD team in 2025. In his spare time, James is a long-suffering Rochdale fan and loves reading, running and music. Contact him via [email protected]

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@JimmyMoorhouse

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Steve Jobs may well be one of the most recognisable and influential names within the tech industry but it seems as if he didn't always leave the best impression.

The former Apple CEO, who passed away in 2011 after a battle with pancreatic cancer, established one of the world's biggest tech companies back in 1976.

He fostered a culture of success as Apple grew into the trillion dollar company that it is today, and that was through a number of unconventional methods that included a 'beer test' for any potential employees.

Jobs also used to ask his senior employees one specific question every single day, which would probably get on your nerves, but it seems as if he knew exactly what he was doing.

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However, you can also see how that might grind some employees down, with Shark Tank businessman and multi-millionaire Kevin O'Leary opening up about his experience working with the tech whiz back in the 90s.

Steve Jobs died in 2011 after founding the global tech empire (Justin Sullivan/Getty Images)
Steve Jobs died in 2011 after founding the global tech empire (Justin Sullivan/Getty Images)

Speaking on the Diary of the CEO podcast, he said: "I used to work for Steve Jobs in the early 90s making all of his educational software. By the way, not a nice guy, not a nice guy.

"He would say to a room full of people, 'Kevin, I don't give a s**t what the students want or the parents think or anybody thinks. It's what I want. They don't know what they want till I tell them what they want.'

"And I said, 'Steve, you sound like such an a**ehole. You have no idea what that sounds like.

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"He says, 'no, no, that's how it is Kevin. Now, are you making money with me? Am I your fastest growing OEM [original equipment manufacturer]? Have we not been wildly successful and continue to be?'

"I said: 'Yes, Steve, that's true.' He said: 'Then f**king shut up and do what I say.'"

Kevin O'Leary went on to make millions of his own (Andrew Harnik/Getty Images)
Kevin O'Leary went on to make millions of his own (Andrew Harnik/Getty Images)

However, he did have some praise for the former Apple CEO's incredible work ethic, which included regular emails at 2am, which may well have included a particularly brutal one which was sent to Adobe when he discovered they were recruiting his employees.

O'Leary then went on to explain the concept of signal to noise ratio - signal being what you want to get done, and noise being what gets in the way of you doing it.

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He said: "What was so brilliant about Jobs, his vision of signal was the top three to five things you have to get done in the next 18 hours you're awake.

"You're going to get those three things or those five things done that you have deemed critical for your mission. They must get done today.

"Anything that stops you from doing that is the noise. So this signal to noise ratio to be successful for Steve Jobs, was 80/20. 80 signal, 20 noise.

"I knew that to be true for him because he would email me at 2.30 in the morning, expect me to get back to him because back then we didn't have texts. It was all email.

"He was right. And the only person that i've seen that has a higher ratio than that is Elon Musk. He has no noise."

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