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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.

HIRE Technologies

Factoid: Kevin O’Leary 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.

The full interview with Kevin O’Leary is here:



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.


  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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