The Biggest Risk 4 Judges on "Shark Tank" Ever Took

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Successful entrepreneurs and business gurus like to talk about the importance of taking risks. And the millionaire judges on Shark Tank are no exception.

“I like to take risks. That’s how I make money,” Kevin O’Leary says.

It’s true that to start your own business, you must make the borderline insane decision to risk all your time, finances and mental, emotional and physical well-being to pursue a dream that may ultimately end up as a nightmare. It’s also true that taking risks and growing your business are synonymous. As the old adage goes: “If you don’t take risks, you will always work for someone who does.”

Related: Why "Big Risk, Big Reward" Is a Myth

But the cynic in all of us may still look at all those super-rich sharks, sitting atop their gilded thrones telling struggling entrepreneurs to take risks, as a bit, well, callous. After all, it’s a lot easier to be a risk taker when you have hundreds of millions or billions of dollars of other people’s money to fall back on.

So we asked a few Sharks -- the new season premieres this Sunday on ABC -- to put some teeth where their bite is. Here they share what they had to risk to get so much back in return.

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