Kevin O’Leary: Cementing a Legacy with the Cold Hard Truth

There’s no question that Canadian entrepreneur Kevin O’Leary is an asshole. But he’s earned the right to be one. 

Kevin O’Leary was a benefactor of the $3.8 billion exit for The Learning Company (also known as SoftKey) in 1999. While in retrospect the acquisition was called one of the worst business deals of all time—Mattel lost hundreds of millions—O’Leary had cashed out just before the dot-com bubble imploded.

In his book Cold Hard Truth, O’Leary talks a lot about SoftKey and how he famously helped build the billion-dollar company from the ground up since the mid-1980s on the back of a $10,000 loan from his mother. And yes, O’Leary was just as relentless back then as he is now on shows like Dragon’s Den, Shark Tank, The Lang and O’Leary Show, and Redemption Inc.  

Rookie Dragon Bruce Croxon said last month at the INcubes event that in the technology world there is no work-life balance. Croxon said he worked his ass off for ten years straight before the eventual sale of Lavalife for tens of millions in late 2010.

O’Leary would expect his employees to be available for at least three quarters of a day, and often seven days a week. It was one of the reasons why the Mattel and SoftKey merger would fail so spectacularly: O’Leary’s company was a fast-moving, rapidly changing enterprise, while Mattel was a sluggish, bureaucratic organization that couldn’t meet the demands of a swiftly altering technology world. Not to mention the tech bubble had crashed and video games cut into Mattel’s traditional gaming dominance. 

O’Leary’s memoir hasn’t come without personal fallout though. His wife has since separated from him, and on a recent episode of Shark Tank, he awkwardly kissed fellow investor Barbara Corcoran as part of a product test. O’Leary is quite contradictory in giving lessons about how to use fame in his book. 

Still, you can’t argue against the 2008-formed O’Leary Funds. It’s grown from nothing to $1.5 billion in three years, Kevin O’Leary says—he’s been very successful on multiple occasions. He even turned Storage Now into Canada’s third largest storage company before being acquired for $110 million in 2007. 

Further, Kevin O’Leary, a serial entrepreneur and renowned venture capitalist, might be more popular today than at any point in his life. He’s on five television shows, has 45,000 Twitter followers, and has even been involved with Discovery Channel’s Project Earth, which flirts with ways to stop and slow global warming. 

Not bad for a guy who had to overcome a lot of adversity in the earlier stages of his life. 

Kevin O’Leary has cemented his legacy—for better or for worse.

Photo: The Globe and Mail