Mark Cuban, known for avoiding investments in companies with unclear branding, may have made an exception for Gatsby Chocolate, which recently appeared on the season premiere of ABC’s “Shark Tank.” The company was founded by brothers Doug and Ryan Bouton, with Doug being the co-founder of the popular ice cream brand Halo Top. Gatsby Chocolate offers a chocolate bar with “about half the calories and up to 75% less sugar” than competitors. Despite the appeal of a low-calorie but tasty candy bar, the Boutons faced challenges, especially with branding.

The name “Gatsby” was intended to evoke a sense of premium, decadence, and indulgence, but some sharks, including Lori Greiner and guest shark Candace Nelson, found it confusing. Greiner and Nelson expressed concerns that the name did not clearly convey that it was a chocolate bar.

The Boutons sought $500,000 in exchange for a 5% stake in their company and assistance in building national awareness. However, the confusing branding and Gatsby’s lack of free cash flow at the time of filming led to skepticism from some sharks, like Kevin O’Leary, who questioned the $10 million valuation.

In the end, a joint deal was offered by Greiner and Cuban: a $250,000 investment, along with a $250,000 loan, for a 20% equity stake that could increase to as much as 40% if the brand achieves $50 million in sales. Doug and Ryan accepted the deal and expressed enthusiasm about partnering with Lori and Mark to enhance the brand’s messaging and generate awareness. They are actively exploring rebranding options, considering “Gatsby Chocolate: The Good for You bar.”

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