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Kevin O’Leary Says Working For Steve Jobs Was Brutal — ‘He Was Not a Nice Guy,’ But O’Leary Still Admires Him Anyway

“Shark Tank” star Kevin O’Leary recalled working for Apple Inc. Co-Founder Steve Jobs during a recent interview posted on LinkedIn. While most remember Jobs for building the technology and innovation giant now a part of most Americans’ everyday lives, O’Leary said he remembers him for a different reason.

O’Leary made most of his money when he sold The Learning Company to Mattel for $4.2 billion in 1999. But one of O’Leary’s business partners in the runup to that acquisition was Apple.

“We, The Learning Company, were his largest provider for educational software when (Apple) wanted to get into schools with the Mac,” O’Leary said. This meant O’Leary and Jobs regularly met to make that happen.

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“He was not a nice guy. He would walk into a room and absolutely berate everybody in there,” O’Leary said.

O’Leary wasn’t the first person to report this. Jobs’s daughter wrote a memoir about growing up with her father. The memoir, titled “Small Fry” by Lisa Brennan-Jobs detailed callous and potentially abusive scenarios like refusing to pay child support, refusing to install heat in her bedroom and telling her she will get no inheritance.

O’Leary questioned whether the success Jobs saw in his early career would work today. Job’s erratic and borderline abusive behavior might not have resulted in the same success decades later.

“What was it like working for Steve Jobs? It was BRUTAL! He was NOT a nice guy,” O’Leary said during the interview on LinkedIn.

Despite having this experience with Jobs, O’Leary said something unexpected. Rather than spite for the late tech founder, O’Leary said he admired Jobs.

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“I admired him for his steal vision and getting where he needed to go. He didn’t let people get in the way,” O’Leary wrote.

While largely part of his Mr. Wonderful character on “Shark Tank,” O’Leary has earned a reputation for being direct and somewhat callous at times. During his time on air, O’Leary is often seen aggressively questioning the valuation of a startup or offering harsh terms to get an investment. While a far cry from statements about Jobs, O’Leary is also an advocate for small businesses and startups, regularly funding businesses across the U.S. and helping entrepreneurs grow their companies to multimillion-dollar exits.

Regardless of whether it would work in today’s corporate world, the results are undisputed. Jobs built one of the largest innovations of the past decade. The startup world can be brutal and unintuitive, but when founders or investors get it right, it can result in a big payday for those involved or changing the world like what happened with Apple.

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