Kevin O’Leary: If my first business didn’t work out, this is what I would have done

Wealth

Investor Kevin O’Leary started his first business out of his basement in 1986. In 1999, O’Leary and his co-founders sold the company to the Mattel Toy Company for $4.2 billion

But even if the business had failed, O’Leary says he would have persisted as an entrepreneur.

“If starting my first company hadn’t worked out, I would have started my second company. If that failed, I would have started my third company. If that failed, I would have started my fourth company,” O’Leary tells CNBC Make It.

“The point is, you only need one hit. And you just don’t know which one it’s going to be.”

Of course, O’Leary has had several hits since. In addition to investing in successful companies via ABC’s “Shark Tank,” O’Leary founded businesses including O’Shares ETFs, O’Leary Financial Group and O’Leary Wines.

And even from a place of success, if he lost it all today, O’Leary says he would still start again as an entrepreneur.

“My motivation, and probably [the same] for most entrepreneurs, is to control my own destiny,” he said. “You can’t make it work every time, but you have to keep trying.”

O’Leary’s “Shark Tank” co-star Mark Cuban also says ”it doesn’t matter how many times you f— up” in business. “You only gotta be right once,” Cuban said on Barstool Sports’ “Pardon My Take” podcast in February.

Self-made billionaire Cuban was persistent in starting multiple companies, even after many failures. Today, Cuban is worth $4.3 billion, according to Forbes.

Working for yourself and starting a business is a difficult route, O’Leary admits, but to him, it’s worth it.

“You’re going to fail a lot more. But when it works, it really works,” he says. 

And it’s not just about money.

“You’re going to get [money] if you’re successful – that’s one of the derivatives,” he says. But it also “gives you that personal freedom to pursue things that you really want to do.”

For O’Leary, what he really wants to do is work more. “That’s what I like to do. That’s the whole point. I enjoy what I do. That’s entrepreneurship,” he says.

“If you get up in the morning at 5:30 and get back to work, you know you’re doing something you love.”

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

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