- December 4, 2025
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A great concept without a strong team goes nowhere, says entrepreneur David Chessler, whose Sarasota-based company, Chessler Holdings, holds diversified investments in multiple industries.
One of Chessler’s newest ventures, the Hustle program at University of South Florida, leverages the power of teams — each of which will compete for monetary prizes as they learn to run a real business, complete with a salary and a board of directors to report to. Hustle stands for Helping Undergraduate Students Tackle Leadership and Entrepreneurship, and it offers mentorship and real-life startup business experience.
Chessler is putting some financial muscle behind the hustle: the Muma College of Business at USF recently announced it received a $500,000 donation from Chessler Holdings. “The younger you are, the more risk you’re willing to take,” says Chessler, “and the more work you put in earlier, the better you learn. It’s scientifically proven that kids learn best when they’re having fun.”