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Kevin O’Leary: My Most Surprising ‘Shark Tank’ Investment That Paid Off Big Time

Kevin O'Leary
Thought Leader: Kevin O’Leary
May 22, 2023

Kevin O’Leary is a Canadian businessman and a shark on “Shark Tank”. O’Leary has partaken in successful business ventures for nearly 40 years, beginning with his founding of the SoftKey software company in 1986. He is also the author of the “Cold Heart Truth” book series.

Recognized by GOBankingRates as a Top Money Expert, here, O’Leary shares advice from his work as an entrepreneur and discusses his most surprising “Shark Tank” investment that ended up being extremely profitable.

\What is 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?

Well, look, I’ve tried my whole investment career to try and 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 what’s most important. People that forecast we’re going into a recession or there’s a hurricane, et cetera, have no idea. You simply don’t know. So make sure to diversify when it comes to your investments.

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, which I thought was a joke, just sold for close to $100 million — you just don’t know. That’s why you diversify.

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