'Shark Tank' Regrets: Investment Flops and Successes

Act 5: From investing in a company that went belly up to not investing in a multi-million dollar idea.
5:36 | 05/03/14

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Transcript for 'Shark Tank' Regrets: Investment Flops and Successes
Narrator: Sometimes the best way to grab the sharks' attention is to toss out the right bait -- literally. Yeah, this baby got back. That's our 1/2-pound "Man-eater." That's a lot of meat, ladies. Mmm! We always get the entrepreneurs bringing food in the set usually right after lunch. Mmm! Narrator: And some of these food pitches have been a real recipe for success. Our cupcake jars are baked fresh daily. That is one damn good jar of cake. Unbelievable. Look at this. It's gone already. Narrator: When Kevin offered a royalty deal for wicked good cupcakes... ...The other sharks warned against it. Trust me, you're not gonna get a worse offer than that. Don't do something that you'll regret afterwards. But they agreed to give Kevin 45 cents for every cupcake sold. Come to mama! So, were the shark warnings justified? To satisfy the country's sweet tooth, the mother/daughter team has added two more baking facilities and are now employing nearly 50 people. Before they met me, they were doing 15,000 a month. Now they're doing 265,000 a month. Does that column drag down the company? Are you kidding? That's why they call me "Mr. Wonderful." Narrator: Ah, the smell and taste of sweet success. But even sharks bite into a bad fish every once in a while. Remember toygaroo? My company is the netflix for toys. O'leary: You have a good idea. This is interesting. I want to be an investor in it. I like what this guy brings. So I'll split it with him. I'll do that. We have a deal. Done! Narrator: Mark and Kevin bought in for $200,000. Great idea. Thank you so much. I was a customer. 36 to 40 bucks a month, they'll send you $300 worth of toys. If your kids get bored with them like every kid does, you package them up. They disinfect them, clean them up, send them to somebody else. Loved it. My kids loved it. Narrator: But in fewer than six weeks... The company went belly-up. Toygaroo is the worst deal I've ever done -- complete collapse of management. They would argue with each other and didn't trust me and didn't trust each other. I don't like zeroes. I don't lose money like that -- ever. That was shocking. Narrator: But sometimes there are regrets of another kind. The sharks let one slip away when maybe they shouldn't have. America's first premium wine by the glass. Just open... And enjoy. Cheers. Narrator: The sharks saw the value of James martin's wine glass on the go... How much are you willing to sell me for $600,000? ...Quickly making offers. I think the packaging is the play. But there were conflicting visions. Can we separate the licensing and leave you with the wine business? I really like your patents. And James wouldn't budge. You've already devalued the brand to this much. Narrator: But neither would the sharks. I'm a dream come true for you. No. James. Really? Narrator: It resulted in the ultimate "Shark tank" standoff. The answer's no. O'leary: Oh. Was arrogant. He didn't listen. Cocky isn't really good. He made every shark hate him within minutes. But within minutes after the show airs, I get hundreds of calls. Cheers. I think that the greed of the sharks clouded the vision of what the financial opportunity was for them. And the worst part is, after he rejected everybody's view, he was invited back by "Shark tank" and rejected us again. That almost made me think about quitting "Shark tank" that day. I'll do the $300,000 for 12%. 8%. Cheers. You know, he was the first gold digger that we ever had, you know, a gold digger being someone who comes in just for the P.R., not really looking to make a deal. If they had taken the investment on the second show for $300,000, that $300,000 today would be worth almost $3 million. I hate that guy. Narrator: Hatred or jealousy? With over $25 million in revenue, looks like James is now flying high and getting the last word again. Sharks, you say it all the time. You blew it, entrepreneur, you blew it. I think this time, you blew it. I don't believe it. Narrator: Next up, the most successful entrepreneur is revealed. But first, what do the sharks really think about daymond John? Daymond at his core is a really nice guy. He's a -- he's a big teddy bear. You know, I think if -- if it was five daymonds up there, it would be called the "Teddy bear tank." John: I'm a family man. I know. I'm buying more into you than anything else. He'll just tell you a nice little story to, you know, let you down easy. I like you. I really do. And the ladies love him. I'm one of the ladies. I'm in his fan club. This is fantastic. He's a sit-in-the-weeds guy. You don't know what he's thinking until he declares, which makes him a big variable. That idea is so brilliant, I'll do the exact same deal, but I'll only take 30%. Sometimes daymond can just be a little too vicious. He starts to pull some dirty tricks. Barb, just 'cause you're an old crab doesn't mean you should get in the lobster business, but

This transcript has been automatically generated and may not be 100% accurate.

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