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Kevin O'Leary brings out his inner rockstar during 'Shark Tank' pitch — and still doesn't offer a deal

Few people would have guessed that Kevin O'Leary had such a fun side to him.
PUBLISHED MAY 22, 2025
Screenshots showing Kevin O'Leary on "Shark Tank." (Cover image source: YouTube | Shark Tank Global)
Screenshots showing Kevin O'Leary on "Shark Tank." (Cover image source: YouTube | Shark Tank Global)

Kevin O'Leary may be a ruthless negotiator and smart investor, but that doesn't mean Mr. Wonderful doesn't like to have fun. Few people know that he’s a decent guitar player, and the investor showcased his talent on an earlier episode of “Shark Tank.” The entrepreneurs who let him do it were Nicholas George and Kevin Mac. They were seeking $75,000 for 10% of their business called Tik Pik, which is a company that makes guitar picks that stick to the instrument.

Mr. Wonderful was invited to the stage to play an electric guitar, and he said that he wanted to play some blues. He absolutely killed it on the six strings and received standing ovations from multiple sharks for his efforts. Despite this, O'Leary wasn't the one who put money into the business.

Screenshot showing Kevin O'Leary playing with one of the entrepreneurs. (Image credit: YouTube | Shark Tank Global)
Screenshot showing Kevin O'Leary playing with one of the entrepreneurs. (Image source: YouTube | Shark Tank Global)

The firm sought to address the problem of the picks that are lost way too easily. If a pick sticks on the body of a guitar and is easily removable, that is the dream scenario. The only issue was that these picks were worth almost $5 a piece, as compared to usual picks that were priced at less than a dollar. So, it was a premium product, but the utility of it is what makes it stand out.

Mark Cuban understood that and was the only shark that made an offer. While he wasn’t in the music industry, he had tried to learn the instrument when he was younger and understood the struggle guitar players faced when it came to picks. Therefore, he offered $75,000 for 16% of the company. The entrepreneurs wanted to see if there were any other offers, but the shark wanted them to accept immediately, so they did.



 

Cuban had a fanboy moment with one of the entrepreneurs before offering the deal. Turns out that Nicholas George was the son of a Calypso singer from the Cayman Islands called The Barefoot Man. The shark completely flipped when he heard that. Turns out that his wife was a huge fan of the entrepreneur’s father, and perhaps that played a part in him offering Tik Pik such a sweet deal.

“Oh my God! The Barefoot Man! Oh my God. My wife just goes like just nuts,” he said. Turns out that Nicholas never wanted to be a musician, but always wrote songs. So, when his daughter told him that she wanted to be a musician just like her grandfather, they wrote an entire album.



 

Kevin Mac revealed that he had to leave his wife at her parents’ house and asked for a couple of years to pursue his dream of doing music full-time. He broke down in tears as he spoke of the immense support she had given him as he claimed to earn a decent living for himself and his family by being a musician.

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