Copa Di Vino, "an arrow to my heart, the pain I suffer when I hear that name," Kevin O'Leary told ABC News.
O'Leary remembers Copa Di Vino as the one that got away.
"I'm very frustrated with that guy," O'Leary said. "Whatever he's doing, I could make it twice the size."
Copa Di Vino founder James Martin is one of the most disliked entrepreneurs of ABC's hit show "Shark Tank," but he is also one of the most successful.
Martin created Copa Di Vino, a portfolio of seven different types of wine that come in a patented glass-like container made out of recycled plastic with a pull-off and resealable lid.
Copa Di Vino promises an on-the-go premium glass of wine without worrying about wasting wine or dealing with a stubborn corkscrew.
Martin's Oregon-based and family-owned winery struggled for years before making a profit. When the opportunity arose to appear on the second season of "Shark Tank," Martin jumped at the possibility for potential investors and additional expertise.
"At that point we had just started the company and we're desperately in need of some cash," Martin told ABC News. "We thought it was a perfect fit for the show and we were really excited to do it."
Martin asked for $600,000 in exchange for 30 percent of his business.
Kevin O'Leary expressed interest, but wanted Martin to separate the patent for the container from the process of bottling the wine. Martin wouldn't budge, telling O'Leary the wine glass was the "special sauce."
"I was so confident in my product that I thought for sure I would get the biggest deal that anyone got on this show," Martin told ABC News. "Instead, I got totally demolished."
The situation was tense in the shark tank after Martin walked out on the offers and brushed off their advice, Shark Barbara Corcoran told ABC News.
"He was arrogant, he didn't listen," Corcoran said. "Everyone was giving him good suggestions. He just dismissed it as though he was talking to no one. He made every shark hate him within minutes."
However, within minutes after his episode aired, Martin said his phone wouldn't stop ringing with people pitching him with offers to invest in his company.
"Today, at what shares trade in the business, that investment would be worth $12 million," Martin said. "That's a 20-times return on investment that they would have received in two and a half years."
The show producers took notice of Martin's overnight success, and offered Martin a rare second chance to go back in the tank.
The standoff between the sharks and Martin went into its second round when neither side budged on the very same point they were stuck on the first time around.
Martin was "the most obnoxious and most stubborn" entrepreneur they had on the show, shark Daymond John told ABC News.
"He was the first gold digger that we ever had," Mark Cuban told ABC News. "It was so obvious and that was when I said I'm out, this makes no sense."
Even though Martin walked away, again, without any of the sharks' investment, the chance to promote his product on national television had huge payoffs.