'Shark Tank' judge Kevin O'Leary blasts contestants for rejecting a deal, then calls them 'bozos'

After the contestants said no to a high-value investor deal, Mr. Wonderful said he had lost all respect for them.

PUBLISHED AUG 14, 2025

Screenshots showing Kevin O'Leary and the entrepreneurs on "Shark Tank" (Cover image source: YouTube | Sony Pictures Television)

Over the years, Kevin O’Leary has built a reputation on "Shark Tank" for being one of the most ruthless investors ever. If it’s a good product with decent numbers, Mr. Wonderful will dedicate his time and effort to making it a success. However, if the company has an unrealistic valuation, he will tear into the entrepreneurs. In an earlier episode of the show, he did just that and then said that he had no respect for them after they turned down a mega deal.

via GIPHY

The company was called The Players Trunk, and it had a team of four entrepreneurs. They sought $650,000 for a 5% stake in their business. What the company did was make merchandise of college athletes and sell them to fans. A lot of these athletes do not even know that a company has made merchandise relating to them, like jerseys, and sells them without paying them any money.

One of the four partners was such an athlete. The entrepreneurs also claimed to have over 800 amateur and collegiate athletes signed up for their program. After these athletes complete college and graduate, they can sell their merchandise at a higher price as they become vintage. It was a decent business model, and the Sharks liked the idea. The problem was their valuation, which was simply astronomical.

Screenshot showing the entrepreneurs making their pitch. (Image credit: YouTube | Sony Pictures Television) — Screenshot showing the entrepreneurs making their pitch. (Image source: YouTube | Sony Pictures Television)

The company had only been in existence for a year at the time of taping, but had roped in $1.3 million in sales. This was a good figure, but it did not even come close to justifying the $13 million valuation. O’Leary was stunned by what the entrepreneurs had asked for and did not hold back. The founders said that they had an investment from a credible venture capital firm, but it was not enough to convince Mr. Wonderful.

“I think that’s a crazy valuation. Now look, maybe they are putting other people’s money to work, but this is my money. I don’t do stupid deals. This deal is stupid. Guys, I’m out, “ he said. This might have been disheartening, but Mark Cuban and guest shark Kevin Hart almost immediately came in with their offer. They, too, believed the valuation to be unrealistic and offered $650,000 for 30% equity.

Screenshot showing Mark Cuban and Kevin Hart discussing a deal. (Image credit: YouTube | Sony Pictures Television) — Screenshot showing Mark Cuban and Kevin Hart discussing a deal. (Image source: YouTube | Sony Pictures Television)

Now, it is important to remember that when it comes to any sports-related business, no one is a better Shark than Cuban. The investor owns professional sports teams and interacts with pro-athletes regularly. These connections in the sports industry are gold. Hart, on the other hand, is a global superstar with brand deals worth millions from all over the world. Striking a deal with them might have shot The Players Trunk to the stars.

However, the entrepreneurs did not want to give up so much of their business and countered with $750,000 for 7.5% equity. This was immediately rejected, and O’Leary had had enough. “Guys, I also respected you until you turned that offer down. Now, I think you’re bozos,” he said. None of the other Sharks made them any offers either.