Kevin O'Leary made one of the biggest deals of his career with this founder — but there was a catch

Among "Shark Tank" judges, Kevin O'Leary is not just an intimidating figure because of his sharp tongue but is also a shrewd negotiator who comes up with offers as creative as many pitches. Andrew McMurray entered the show with single-serve wine glasses under his brand Zipz, only to make one of the biggest deals in the show's history, which came with a catch. O'Leary did offer him an investment but also slipped in a condition that ensured that he could make the most of the business, if the product became a success.

McMurray had asked for $2.5 million for 10% equity in his business, and as he started his pitch, he explained that his company is all about packaging and licensing before mentioning how it was right up O'Leary's alley. "You're a smart grasshopper," Mr Wonderful, noted.

The BPA-free single-serve wine glasses from Zipz were so strong that he could stand on them. McMurray claimed that they lasted for a year, which prompted O'Leary to ask about the patent. The founder shared that it was a French company that came up with the technology, and they were undergoing tests to determine the exact shelf life.

Coming to numbers, the entrepreneur shared that the company had made $130,00 in licensing fees from big stores like Walmart. He added that there was an investor who had provided $8.5 million, a number that upset several Sharks. Mark Cuban, Daymond John, and Lori Greiner dropped out early and quietly, with Robert Herjavec following suit later. The only Shark left was Mr Wonderful O'Leary, who explained that he had been negotiating a deal for O'Leary Wines with COSTCO and he could do the same for Zips as well. However, he had major problems with the price of $3.99 for a single glass of wine.

"Majority of wine in America is sold for $9.95 a bottle. So where this packaging idea has so much merit in terms of its delivery it fails on its pricing," he said."The average consumer can get five and a half glasses for $9.99 and $3.99 for a glass is the problem," O'Leary added. 

He further tried to sober up the entrepreneur, saying that getting a deal with COSTCO, the largest buyer of wine, isn't easy. After some intense negotiations, Mr Wonderful offered $2.5 million for 10%, but he demanded an option to buy another 10% at the same $25 million valuation if they successfully got into COSTCO. "So, if you sell the company at some point for $50 million, I get to buy the 10% at the same $25 million valuation," he explained. McMurray then went out to make a call and sealed the deal with O'Leary after coming back.

Things seemed to go well for a while for Zipz as McMurray made an appearance in a follow-up appearance on the "Shark Tank" sister program "Beyond the Tank" in 2016. However, O'Leary appeared frustrated with how slowly things were moving as the company was yet to turn a profit.

According to the Food Republic, the company went quiet online after pivoting to a  B2B model shortly after its appearance on the follow-up. Furthermore, the COSTCO deal that O'Leary was so keen to clinch never materialized.