Entrepreneurs dreamed of landing a spot on “Shark Tank” to pitch their idea or business for funding, but some of the deals struck on the show were not as good as they had hoped. There has been a long history of bad deals, as well as good ones and missed opportunities, but some stand out as the worst deals in the show’s history.

Hill Billy

Hill Billy is a fashion label. The company’s owners appeared on “Shark Tank” and asked for a $50,000 investment in exchange for a 25% stake in the company. They had some talks with the sharks, and Jeff Foxworthy and Daymond John both expressed interest in turning the company into a skiing and snowboarding company, but things went south. The owners admitted that they were not there to do business with any of the sharks. They didn’t care about the money; all they wanted was to appear on national television to promote their new business. This was one of the worst “Shark Tank” deals in history because, while nothing illegal occurred, the representation was deceptive.

Toygaroo

The Toygaroo toy company’s owners appeared on “Shark Tank” in 2011 to make their pitch to the sharks. The business’s premise was novel, and they did an excellent job of explaining how the company that both rented and sold toys provided parents with a way to save money. Because children grow tired of toys quickly, this provided them with the opportunity to try them out on a rental basis before purchasing them if they were satisfactory. This deal was taken up by Mark Cuban, who invested $50,000 in the company. Toygaroo stopped taking orders, suspended their social media, and filed for bankruptcy within a year. In the end, Cuban lost every penny of his investment, and no reason for the company’s failure was ever given.

Breathometer

The Breathometer has to be one of the worst deals in “Shark Tank” history. This invention was a portable breathalyser that could be plugged into the audio jack of a smartphone. It would provide a reading of the blood alcohol level as well as feedback to let the user know if they could legally drive or if they should find a ride. While this sounded like a good idea at the time, and all five sharks came together to invest $1 million for a 30% stake in the company, it turned out to be a total flop. Following the investment, the company encountered a slew of issues. For starters, the company had trouble filling orders. Furthermore, the Breathometer was tested and found to be far less accurate than the company had promised. On some occasions, it reported the BAC to be far lower than it actually was, implying that people could drive when they had no business doing so. The Federal Trade Commission became involved in the investigation and ordered Breathometer to refund all of its customers in full.

Tycoon

Aaron McDaniel, a San Francisco entrepreneur, pitched his real estate crowdfunding company Tycoon Real Estate on Shark Tank in 2015. It didn’t go as planned. “Scammy” and “spooky” were two words thrown around by the investors. One (Kevin O’Leary) questioned McDaniel’s honesty by asking if he had ever been imprisoned.

Gayla Bentley Fashion

Gayla Bentley created Gayla Bentley Fashion, a line of chic clothing for women sizes 12-28. The charismatic saleswoman pitched her company on Shark Tank, claiming to make $500,000 per year in sales. Bentley explained to the Sharks that she needed money to open a flagship store in Houston, Texas. She joked on TV after negotiating a deal with Daymond John and Barbara Corcoran, “Let’s go eat!”