In a Q&A with Oxford Union students in 2017, Mark Cuban shared one of his biggest regrets about Shark Tank — and he didn’t hold back. When asked about his commitment to the companies he invests in, Cuban emphasized that he will stay there “until death do us part” as long as the founders keep grinding.
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Of his 71 investments on the show, about 12 to 15 are flourishing, while three have folded (though, as he joked, “none really exciting”). Then he got real: At the bottom of his wallet, Cuban revealed, “10 out of 71…three have gone bankrupt and seven have gone bankrupt, but they’re not smart enough to know.” The crowd laughed, but Cuban didn’t let the moment pass 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 mention 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’ passion and the product’s potential. Thanks to Shark Tank’s huge PR boost, sales shot up 1,500% after the episode – you’d think this was the start of something big. But behind the scenes, things quickly unraveled.
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The problem? Free shipping. Cuban explained that while the pretzels cost about $14, they were sold for $29.95, which should have yielded a decent profit margin of $15. But shipping? It was $16 each. That “free shipping” benefit, which was supposed to attract more customers, ate into profits. Cuban described it as watching cash “just disappear,” adding, “Cash goes like this,” gesturing to indicate how quickly it dried up. And it wasn’t just shipping. The company reportedly faced complaints about delays, adding customer service issues to the pile.
Looking back on the deal, Cuban admitted, “I probably shouldn’t have done that [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.
