Mark Cuban reveals his best and worst ‘Shark Tank’ deals — and the one mistake to avoid when pitching

Mark Cuban shares the best pitch he’s seen, and the one investment he’d definitely take back
PUBLISHED JUL 10, 2025
Mark Cuban listens to testimony during a Senate Judiciary Subcommittee hearing on Capitol Hill. (Cover Image Source: Getty Images | Photo by Mark Wilson)
Mark Cuban listens to testimony during a Senate Judiciary Subcommittee hearing on Capitol Hill. (Cover Image Source: Getty Images | Photo by Mark Wilson)

Mark Cuban has seen enough ‘Shark Tank’ pitches to figure out which ones have potential and which ones are shady! There’s a reason why the investors on ABC’s hit business show are called "sharks." Cuban always asks contestants the right questions to gauge whether the product and company they pitch make sense and are a product-market fit. Speaking to Business Insider, the AXS TV chairman and owner of the Dallas Mavericks opened up about the best and worst pitches he has seen on the show. “The worst was easily the two doctors that came on this season,” he said, referring to the Arizona-based doctor brothers Richard and Albert Amini from season five.

“They kept on throwing out buzzwords about social media as if that would wow us. They had no company. No business. No clue,” he added. The contestants pitched their app called RoloDoc, which was meant to be a secure social media platform for physicians to upload and display their medical records. “What we’re trying to do is bring social media and the social network to the medical profession,” the brothers, both doctors, claimed. They had a great idea, but no data backing up the claim. Overall, the entire business had no proof of concept and was far from being established. This frustrated the judges, and for good reason!

When asked about the ‘Shark Tank’ pitch that Cuban liked the most, he named the Plate Topper guy from season four. “He was the longest deal we have ever had. It went on for two and a half hours,” the billionaire investor recalled. “The entrepreneur was a J.D., Ph.D., and MBA, I believe. He knew every answer to every question,” he added. Cuban revealed that the contestant thought he was smarter than all the judges, but with every cross-question, he was proven wrong. However, he admired the entrepreneur’s determination.

“What I loved about him is that he never quit and kept coming back at us with confidence and eventually got a deal,” he said. When asked for his advice for hopeful entrepreneurs, Cuban said budding companies must build a real operation that could “get real traction in a new industry that has a ton of upside.” However, the thing that could potentially make the investors lose interest is long backstories. “It's not the time to talk about your struggles and hard work. Every entrepreneur has a similar story. You have to get right into the meat of the business,” he added.


 
 
 
 
 
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Cuban has been part of several seasons of ‘Shark Tank’ and has made a wide range of investments on the show. While some turned out to be wise choices, others he slightly regretted. When asked about his worst investment, he recalled it being Toygaroo, a subscription service for toys. “They went out of business,” Cuban said. The investor is joined by other sharks on the show, including Kevin O’Leary, Barbara Corcoran, Lori Greiner, and more. He revealed that they “hang out” off-screen, but it doesn't reduce their competitiveness. "I don't recall ever losing a deal I really wanted," he said.

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