Kevin O’Leary talking about someone else kindly and respectfully is as rare as a Hailey’s Comet. But as the saying goes, “real recognizes real,” and in Kevin’s case, the real is someone like the Apple godfather Steve Jobs. We cannot blame Mr. Wonderful for having such wonderfully high standards.
Kevin recently spoke on a podcast about his experiences with Steve Jobs. He described Jobs as tough, blunt, and demanding (to say the least and put it mildly). All of Jobs’ toxic boss traits were rooted in making Apple the mammoth it is today. Safe to say he was successful.
But the larger question at hand is, till when are we going to use hustle culture as an excuse to justify borderline human rights violations? That is a story for another day.
Kevin O’Leary on Steve Jobs and Apple
Kevin O’Leary worked with Steve Jobs and Apple for several years in the late 90s and early 2000s. This was after Apple acquired his educational software company, The Learning Company. This gave him the opportunity to observe Steve Jobs from close quarters for an extended period of time.
Jobs is (in)famous for being a brash loudmouth, often treading on the line of rudeness. An HR nightmare in today’s day and age. His antics would probably get him cancelled today if it weren’t for his unfortunate and untimely demise.
Lucky for him, he wasn’t born in late eighteenth-century France. That would also involve the masses cheering for his name, but for different reasons that do not involve an Apple product launch.
But his legacy lives on, as Kevin O’Leary does not hold back on being patronizing. Maybe it’s something that comes with being filthy rich, entitled and bald.
The CEO Who Could Out-Intimidate Kevin O’Leary
Kevin wears his time with Steve Jobs as a traumatic badge of honor. Mr. Wonderful once shared a not-so-wonderful incident where, while he was working with Apple in the early 1990s, Jobs would often email him at 2:30 AM and expect an immediate reply.
Apt that he has “Jobs” in his name, considering his whole life revolved around that (apparently).
Imagine how insufferable you have to be for Kevin O’Leary to describe you as “not a nice guy.” Kevin said that while recalling a sharp exchange with the Apple boss when he worked with him in the early 90s.
Kevin shared on a podcast how Jobs once lost his patience with him. He cut Kevin off by saying, “Shut up and do what I say.”
He shed more light on this exchange with Jobs. One time, Steve, with his modest humility and grace, said to O’Leary, “Kevin, I don’t give a s**t what the students want. They don’t know what they want until I tell them what they want.”
O’Leary recalled snapping back at Jobs, calling him “such an a**hole.” Jobs didn’t flinch. He asked if Apple was O’Leary’s most profitable and fastest-growing partner. When O’Leary admitted it was, Jobs fired back, “Then just shut up and do what I tell you.”
This explains a lot of Kevin O’Leary’s behavior today. Steve Jobs makes someone like Kevin O’Leary sound like a nice guy in business.
The Apple Way
O’Leary shared that Steve Jobs based his work around what he called the “signal-to-noise ratio.” The signal was the few tasks that truly mattered each day. The noise was all the distractions that pulled focus away from them.
Jobs put most of his effort into the signal and ignored almost everything else. O’Leary said this mindset was a big reason Apple became the company it is today.
Many other sources have also confirmed that working with Jobs was often unpleasant. Still, his intense focus pushed Apple forward to achieve results, turning it into one of the most successful companies in history.
The Contrast Between Jobs’ Philosophy and Apple Today
Kevin’s stories line up with what many have said about Steve Jobs over the years. He was a tech tycoon, an innovative capitalist who wasn’t interested in being polite. What mattered to him was the end result.
O’Leary shared one remark that stood out. Jobs often quoted Henry Ford, saying that if Ford had asked people what they wanted, they would have said a faster horse. Jobs followed this with his own view: People often don’t know what they want until it’s shown to them.
The irony of it is that now Apple is infamous for dropping the same product in different packaging every year, and has also been legally charged with purposely slowing down older models.
Speak of faster horses, we ended up getting intentionally slowed ones. It probably got them more sales at the cost of goodwill, but that is how Jobs went around his business as well.
