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'Shark Tank' contestant comes to the show in his boxers and it went as expected

The valuation he asked for was as crazy as the outfit he wore, and the sharks said no.
PUBLISHED OCT 19, 2025
Screenshots showing Mark Cuban and the entrepreneur on "Shark Tank" (Cover Image Source: YouTube | Shark Tank Global)
Screenshots showing Mark Cuban and the entrepreneur on "Shark Tank" (Cover Image Source: YouTube | Shark Tank Global)

While most entrepreneurs on "Shark Tank" focus entirely on making a product innovative enough for a good pitch, some also dress up to make a statement. Once in a while, sharks come across a contestant who manages to stand out from the crowd. While it makes the pitch unique, it does not guarantee that the founder will get a deal. Such was the case of an entrepreneur who came to the show dressed in boxers and a shirt that was unbuttoned.

The contestant was a man named Zach Crain, and he sought $200,000 for a 10% stake in his company, Freaker. It sells a drink insulator, seemingly made of wool, that is stretchable enough to put any drink container in it. Be it a glass, a coffee mug, or a big bottle of wine, the Freaker can fit anything and give it a personalized look.

Screenshot showing the product. (Image credit: YouTube | Shark Tank Global)
Screenshot showing the product. (Image credit: YouTube | Shark Tank Global)

Crain claimed that his company had a $2 million valuation, and it did not take Kevin O’Leary long to ask about revenue. The entrepreneur said that he had been in business for 13 months, and in that time, he had made $320,000 from sales. This was an impressive feat for such a product.

“You’re not so crazy, you are making money,” Mr. Wonderful said. Crain even had a decent distribution network with 200 stores in the bag, along with Japanese and Canadian distributors. He had a patent approved for the product as well. But the problem with the business was that its valuation was much too high for the kind of revenue that it had brought in.

Screenshot showing Kevin O'Leary. (Image credit: YouTube | Shark Tank Global)
Screenshot showing Kevin O'Leary. (Image source: YouTube | Shark Tank Global)

O’Leary might have been interested in the company, as he said that he would invest if he were to get 50% of it. This was not too much to ask for, as the company was new and had just earned a revenue of more than $300,000. The entrepreneur did not agree to this, and Mr. Wonderful said he was out. Crain also said that he did grilled cheese parties, which he used as a marketing strategy. However, he was not one to go to festivals to sell his product, which came as a shock.

Screenshot showing the entrepreneur. (Image credit: YouTube | Shark Tank Global)
Screenshot showing the entrepreneur. (Image source: YouTube | Shark Tank Global)

All of the sharks agreed that the company was valued at a lot more than it was actually worth, and so every judge refused to offer a deal. The entrepreneur also made a lot of weird noises during the pitch, which the sharks absolutely hated to their core. Mark Cuban said that he would shoot himself if he heard those noises every day as a business partner.

More on Market Realist

'Shark Tank' contestant rejects Barbara Corcoran's offer making her slump on her chair in disbelief

Farmer on 'Shark Tank' with dreams of helping smaller meat producers gets life-changing deal

'Shark Tank' contestant gets Mark Cuban to try fake eyelashes and ends up with a $100,000 deal

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