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Mr. Wonderful: Is fear of failure in your DNA?

Looking for angel money? Courting an investor isn't easy. Just ask the four entrepreneurs who met with Kevin O'Leary, the outspoken entrepreneur and investor known as "Mr. Wonderful" on the TV series Shark Tank. He grilled the business owners of web ventures —Rap Genius, Milk & Honey, Plated.com and lover.ly—to find out how they plan to position their companies for the future.

He quizzed them on the outlook for their respective markets. To get a pulse reading on their chances of success, he also probed to learn about their competitors and their profit margins in the months ahead.

The goal of the guru was to see how he could help these upstarts get noticed and build a brand name, while helping them build sales and become profitable.

Rap Genius co-founder, Illan Zechory, who does not expect his company will turn a profit this year, had to defend this longer-term strategy to Mr. Wonderful, after the investor asked: "Why do you hate money so much?"

Confident in the power of his brand, Zechory remained unflappable. "People are already comparing us to Google and Mark Cuban tweeted that searching yourself on Rap Genius is the 'new Googling yourself.'"

Continuing the conversation, the four entrepreneurs and O'Leary discussed whether entrepreneurs are born, or made.

The entrepreneurs admitted there is something special about the spirit of an individual who is willing to take their fate into their own hands and face all the risks that go along with the business challenge. But many of these traits may be learned as well, according to Nick Taranto, Plated.com's co-founder.

One of the key traits these mavericks must have, of course, is fearlessness. Entrepreneurs must face failure and have the true grit to rebound. Kellee Khalil, founder of the wedding ideas site, lover.ly sumed it up nicely: "Failure is something that you think about, but it's not even an option."

TUNE IN: Tomorrow on Squawk Alley, Kevin O'Leary will continue the conversation with these four determined entrepreneurs.


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