100 Financial Experts Kevin O’Leary

Kevin O’Leary

Shark on 'Shark Tank'

"I want to go to bed richer than when I woke up. The pursuit of wealth is a wonderful thing, but the thing is you have to be honest about it, you have to tell the truth."


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accurate as of 05/15/2023


Kevin O’Leary is best known as one of the longest-running investors on “Shark Tank,” but this tough-as-nails businessman — known to fans as “Mr. Wonderful” — has a business pedigree most would envy.

The Canadian businessman made it big by founding SoftKey, a major software company that specialized in educational titles in the 1980s. Since, he’s been a regular on a variety of television shows, hosted and produced his own television series, and authored several books on money, relationships and business.

Why He’s a Top Money Expert:

O’Leary’s business acumen, keen insights and ambition make him a major money player.


What’s your best entrepreneur/life advice?

Don’t fear failure, particularly if you are an entrepreneur. You are going to fail, and there’s a great lesson to be learned from that.

What advice would you give people who want to invest but are worried about the instability of the market?

I’ve tried my whole investment career to time the market and have failed miserably. You simply can’t do it. You have no idea what the market’s going to do next. You have to get diversified — that’s most important.

How do you know if something is going to be a great investment?

You don’t always know. I can guarantee you that having done “Shark Tank” for 14 years, the deals that I thought were the greatest I didn’t make that much money on. And then you get something like Base Paws, which was a cat DNA test that I thought was a joke, which just sold for close to $100 million. You just don’t know. That’s why you diversify.

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