Mark Cuban Reveals Regrettable Shark Tank Deal That ‘Drives Him Crazy’ Was A Chocolate Covered Pretzel Company Who Offered Free Shipping

In a 2017 Q&A with Oxford Union students, Mark Cuban opened up about one of his biggest regrets on Shark Tank – and he didn’t hold back. When asked about his commitment to the companies he invests in, Cuban emphasized that he’s there “’til death do us part” as long as the founders keep grinding.

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Out of his 71 investments on the show, about 12-15 are thriving, while three have exited (although, as he joked, “none really exciting”). Then he got real: at the bottom of his portfolio, Cuban revealed, “10 out of 71 … three have gone out of business and seven have gone out of business but aren’t smart enough to know it.” The crowd laughed, but Cuban didn’t let the moment slide without giving an example of a deal that “still drives him crazy.”

The investment he was talking about? A chocolate-covered pretzel company. Although he didn’t name it in the Q&A, the company was The Painted Pretzel, founded by Raven Thomas. Cuban had put $100,000 into the company for 25% equity after being impressed by Thomas’s passion and the product’s potential. With the huge PR boost from Shark Tank, sales skyrocketed by 1,500% post-episode – you’d think it was the beginning of something big. But behind the scenes, things unraveled fast.

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The issue? Free shipping. Cuban explained that while the pretzels cost around $14, they sold for $29.95, which should’ve left a decent $15 profit margin. But shipping? It was $16 a pop. That “free shipping” perk that was supposed to attract more customers devoured the profit. Cuban described it like watching cash “just disappear,” adding, “Cash is going like this,” motioning to show how fast it bled out. And it wasn’t just shipping. The company reportedly faced complaints about delays, adding customer service issues to the pile.

Reflecting on the deal, Cuban admitted, “I probably shouldn’t have [invested],” hinting that it was partly to prove a point to his fellow sharks, especially Kevin O’Leary, when he was new to the show. “No lie, to this day, I still get emails …” he trailed off, looking visibly frustrated.