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Kevin O’Leary met his bully match in Steve Jobs

In 1998, Kevin O'Leary met his match in the bully department when he traveled to Cupertino to meet with Steve Jobs.

In 1998, Kevin O’Leary met his match in the bully department when he traveled to Cupertino to meet with Steve Jobs.

Before he was the divisive, opinionated character from Dragons Den, Shark Tank and The Lang and O’Leary Exchange, Kevin O’Leary was hustling to make a buck. And he’s done okay; O’Leary’s net worth is now estimated to be in the range of $300-million.

When the Kevin O’Leary biography is written it will note that he made his fortune by founding educational software company Softkey, which eventually took the name of one of its many acquisitions, The Learning Company, and was acquired by Mattel for $3.2-billion, in 1999.

A news item today, that Apple’s iPad had another major win in the educational market, reminded us of the time when O’Leary met his match is the bully department.

In 1998, Apple had just a 2.5% market share in the education space and O’Leary, concerned that the titles he was developing for Mac weren’t making economic sense, went to Cupertino and sat down with Steve Jobs. O’Leary wanted $54-million dollars to develop the next round of titles for Apple.

Kevin O’Leary’s net worth is approximately $300-million

What followed, describes O’Leary, was an abusive tirade that continued when he was in the parking lot, with Jobs screaming at the future Dragon from a window above.

All in all a pretty funny story that gives some insight into the frustration and uncertainty that was Apple in 1998, and the volatile personality of the late Jobs, something that will be less surprising to those who have read Walter Isaacson’s biography of Jobs.

O’Leary, meanwhile, may be a household name in Canada, but he has a ways to go to match the level of success of his one time tormenter. Steve Jobs net worth, upon his death, was estimated at $10.2-billion.

Was Steve Jobs a jerk?

So this is one question that always comes up, and it is “Was Steve Jobs a jerk?”. The answer is almost certainly yes. How do we know? Take his daughter’s autobiography. Lisa Brennan-Jobs, in her book “Small Fry” revealed that Steve denied he was her father until a paternity test proved it. That was when his awful legacy as a parent began, reportedly.

“He rarely saw her when she was a young child, she says, even after admitting his paternity,” noted writer Troy Wolverton. “While he was avoiding her and avoiding paying child support — despite already having founded and been making money at Apple — she and her mother lived in poverty, subsisting on welfare payments, her mother’s low-paying jobs, and the charity of others. When he was finally forced to pay child support, he made sure that the case against him was closed days before Apple went public and he became a multimillionaire.”

Wolverton offers that Lisa Jobs came off as a victim of abuse and wanted to write the book as a way of making peace with the relationship.

Steve Jobs net worth kept climbing

It seems particularly cruel of Jobs to deny child support when one considers that his net worth was soaring from an early age.

“I was worth about over $1 million when I was 23, and over $10 million when I was 24, and over $100 million when I was 25, and it wasn’t that important,” Jobs said in 1996 PBS documentary.  “I never did it for the money.”

And it especially bizarre considering Jobs genuinely seemed to not care about cash, as detailed by his biographer Walter Isaacson.

““His house in Palo Alto is a house on a normal street with a normal sidewalk — no big winding driveway, no big security fences,” Isaacson told 60 Minutes.” “You could walk into the garden in the back gate and open the back door to the kitchen which used to not be locked. It was a normal family home.”

As previously mentioned, at the time of his death, Job’s net worth was a reported $10.2-billion.

Isaacson’s biography suggests that perhaps Jobs had trouble relating to anyone in his life, recounting that he didn’t say goodbye to his parents the day they dropped him off at college. But his explanation does at least suggest he was aware of his detachment.

“[When his parents dropped him off] he refrained from even saying good-bye or thanks,” the biographer wrote. “He recounted the moment later with uncharacteristic regret: “It’s one of the things in life I really feel ashamed about. I was not very sensitive, and I hurt their feelings. I shouldn’t have. They had done so much to make sure I could go there, but I just didn’t want them around. I didn’t want anyone to know I had parents. I wanted to be like an orphan who had bummed around the country on trains and just arrived out of nowhere, with no roots, no connections, no background.”

Did Steve Jobs give to charity?

So was Jobs charitable in other ways? Perhaps to people he didn’t know? The answer, at least from one source, is also no.

Unlike most other billionaires, Jobs didn’t donate to charity for moral, ethical, or even tax break reasons. For example, he was not a member of the philanthropic campaign The Giving Pledge (via The New York Times),” explained writer Kate Hagan Gallup.

One natural response to stories such as these is to ask why? Why was Steve Jobs such a jerk to what seems like everyone who came in contact with him. A former Apple employee, who was fired by Jobs, took a stab at explaining.

“Apple founder Steve Jobs could be a real jerk when criticizing employees. He said exactly what he meant, often using profanity to get his point across,” said Matt Rosoff for Business Insider. “He once fired the head of the team who created MobileMe, Apple’s first attempt at a cloud service, in a public meeting in front of his team. There are many examples of him almost bringing employees to tears.”

Rosoff said that jobs felt he had no time to sugarcoat or be ambiguous about his feelings with employees and that doing so would simply confuse them and impair the company’s progress.

Was Steve Jobs adopted?

Some have tried to look for clues to his behavior in his past. Jobs was born on February 24, 1955, in San Francisco. He is the son of two University of Wisconsin grad students, Joanne Schieble and Abdulfattah Jandali who put him up for adoption. According to Biography.com, Jobs clearly inherited smarts from his biological parents, as school was basically a joke to him.

“While Jobs was always an intelligent and innovative thinker, his youth was riddled with frustrations over formal schooling. Jobs was a prankster in elementary school due to boredom, and his fourth-grade teacher needed to bribe him to study. Jobs tested so well, however, that administrators wanted to skip him ahead to high school — a proposal that his parents declined,” the site noted.

Bill Burr rips Steve Jobs

Jobs was so famous for being a jerk that one of the more famous comedy routines of late is about him. Bill Burr was clearly not sentimental about the loss of Jobs when he did a routine in California shortly after the Apple founder’s death, taunting his fans in the audience.

“Actually nerd Jesus died last year, right? – Steve Jobs. Yeah, he died, right? I know. I know. Lot of nerds are here tonight. I know. You are sad. I didn’t get it. I didn’t get the big deal made about that guy. When he died, they’re like, “He changed the world.” That’s insane. “He changed the world! The world was one way! And then Steve Jobs came, and it was another!” What did he do? Somebody, for the love of god. What the freak did that guy do? What he do? He told other people what to invent. “I want my entire music collection in that phone. Get on it!” Right? Then these poor nameless faces scientists gotta go into the back room, and figure it out. “How the freak we are going to get all of this into this? I mean. What year is this guy think it is? This guy is crazy. This is like Buck Rogers. Dude, my kid has a birthday like in 11 months.”









The full interview with Kevin O’Leary is here:


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About The Author /

Cantech Letter founder and editor Nick Waddell has lived in five Canadian provinces and is proud of his country's often overlooked contributions to the world of science and technology. Waddell takes a regular shift on the Canadian media circuit, making appearances on CTV, CBC and BNN, and contributing to publications such as Canadian Business and Business Insider.
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  1. Something’s not quite right with O’Leary’s story. In late 90s, we had a cross-platform Macromedia Director that was used virtually by every educational software developer back then.You needed little extra budget for Mac system.

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