Kevin O'Leary

Kevin O’Leary is the guy on Shark Tank who will look an entrepreneur dead in the eye and tell them their business is worthless. He’s earned the nickname “Mr. Wonderful” and yes it’s sarcastic but also kind of not? He genuinely believes he’s doing people a favor by being brutally honest. And honestly, he’s usually the most entertaining person in the room.

O’Leary is Canadian, born in Montreal. He studied environmental studies at the University of Waterloo which is not at all what you’d expect from the guy who became the show’s resident money obsessive. After school he got into software and co-founded SoftKey, which grew into The Learning Company and eventually got acquired by Mattel for $3.7 billion. That deal is its own wild story but the short version is it made Kevin very rich.

After that he started O’Leary Funds, got into wine, got into other businesses, and basically built a whole portfolio of ventures. He’s been on Shark Tank since 2009, day one, and his thing is royalties. The man loves a royalty deal. Where other sharks want equity, Kevin wants a dollar amount per unit sold until he gets his money back and then some. Entrepreneurs either love that structure or hate it.

He’s also the shark most likely to tell someone to take their business behind the barn and shoot it. But when he does invest, he’s serious about it. He wrote “Cold Hard Truth: On Business, Money, and Life” which is pretty much exactly what you’d expect from the title.

A few things worth knowing:

• Co-founded SoftKey/The Learning Company, sold to Mattel for $3.7 billion
• Original Shark Tank cast member since season 1
• Famous for his royalty deal structures
• Author of “Cold Hard Truth” and other books on money and business