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Mark Cuban has seen it all during his long tenure on Shark Tank. With more than a decade of deals under his belt, the billionaire investor has backed everything from game-changing tech startups to quirky products that went viral overnight. While Cuban has scored big wins with investments like Scrub Daddy and Bombas, he’s also taken a fair share of losses. But one deal stands out as his worst investment, a misstep he describes as “my biggest beating.”
That dubious honor goes to Breathometer, a portable breath-testing device that initially seemed to have massive potential. The pitch was so convincing that it made history on Shark Tank, bringing all five Sharks – Cuban, Kevin O’Leary, Daymond John, Lori Greiner and Robert Herjavec – together to invest a combined $1 million for a 30% stake, valuing the company at $3.3 million. It seemed like a slam dunk.
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But the dream quickly turned into a nightmare. In a 2022 interview with CNBC, Cuban opened up about how his early optimism gave way to frustration. “It was a great product,” he said. However, his enthusiasm faded when he began following founder Charles Yim on Instagram. “I’d look at his Instagram and he’d be in Bora Bora … Two weeks later, he’d been in [Las] Vegas partying and then he’d be on Necker Island with Richard Branson,” Cuban said. Exasperated, Cuban began texting Yim: “What the f – are you doing? You’re supposed to be working.” Yim, according to Cuban, often replied that he was “networking” for the business. But Cuban wasn’t convinced, later saying, “Next thing you know, all of the money’s gone.”
Despite the early promise, Breathometer’s troubles weren’t just about the CEO’s travel schedule. By 2016, Yim had pivoted to a new product called Mint, which aimed to measure sulfur compounds in the mouth to determine bad breath.
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The pivot reportedly didn’t save the company from scrutiny. In January 2017, the Federal Trade Commission (FTC) filed a complaint, alleging Breathometer misled customers about the accuracy of its products. The FTC determined the company “lacked scientific evidence to back up their advertising claims” and forced the company to notify and refund every customer who had purchased a device.
