Why Kevin O’Leary makes his life and money decisions the same way: ‘I live life with a portfolio approach’

Everybody has bad days. Even Mr. Wonderful.

But every tough situation in Kevin O’Leary’s life, he says, is typically counterbalanced by something else. That’s “because I live life with a portfolio approach,” O’Leary, 67, tells CNBC Make It. “I don’t risk it all in any one thing.”

The star of ABC’s “Shark Tank” and chairman of O’Shares ETFs says he approaches his life — both personally and professionally — the same way he approaches building a successful financial portfolio, by engaging in many different pursuits at once. The same theory, he says, applies to choosing which specific endeavors to take on.

“I only pursue things today that mean something to me,” he says.

That theory has helped define his entire career: For O’Leary, the choice to lead a largely entrepreneurial life, from founding a software company that eventually sold for $4.2 billion to investing in a wide variety of start-ups today, is deeply meaningful because it enables his “pursuit of personal freedom.”

That sense of freedom has been a goal of his ever since he was fired during his first day of work as an ice cream scooper at a mall store called Magoo’s Ice Cream Parlour, he says. As O’Leary recounts it: The store’s owner asked him to scrape gum off the floor, he declined and was promptly dismissed. The experience taught him to build a life where he could “control my own destiny,” he says.

“The whole idea of entrepreneurship isn’t greed for money,” he adds. “You work really hard so that one day, you don’t have to answer the phone.”

On any given day, O’Leary says, he might be notified at 5 a.m. that one of his investments is about to go bankrupt or otherwise face an impending disaster. “But that call can be interrupted by somebody saying we just got an acquisition offer for $100 million in cash,” he says, noting that the cycle of good news constantly counterbalancing bad news “happens every day.”

The key, he warns, is to avoid getting too caught up in the lows or the highs — which can be difficult when everything you pursue is personally meaningful to you. Some things will work out, he says. Others won’t.

“But I keep moving forward,” he says.

Disclosure: CNBC owns the exclusive off-network cable rights to “Shark Tank.”

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