Local entrepreneur funds college business contest with $500,000

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.”

The Hustle contest, he adds, is a game with atypically high stakes: the winning team of two finalists will be awarded $75,000, and the runner up will win $25,000. The winning teams will then have the additional opportunity of choosing what to do with their prize money, such as reinvest in the business or take a bonus. (Teams are expected to present pitches to judges by Oct. 15.)

Chessler came up with the concept of hustle, he says, and brought the idea to Chessler Holdings’ intern, Alexis Melone, an undergraduate student at FSU who has been engaged in the program since its beginning.  Engineered utilizing Chessler’s existing ART — Automated Retail Technologies — business of automated food kiosks, the hustle program has participants buy ART kiosks from his company, utilize a budget and decide what products to put in kiosks.

ART includes an automatic, oven-baked food vendor, JustBaked, and a robotic frozen yogurt maker, Reis & Irvy’s. Teams will start by choosing what to do with a $250,000 investment to purchase at least 10 ART kiosks and place them around the USF Tampa campus and surrounding areas. Students will earn up to $20 an hour as they manage these kiosks. Teams can also share in profits from the kiosks.

When competing, students will ask themselves questions: “Should I take a quarterly dividend or put profits back in the business?” says Chessler, for one example.

“This unique program has several benefits,” said Dirk Libaers, director of the Center for Entrepreneurship in the USF Muma College of Business. “Students learn how to work on a team, formulate a business plan and execute that plan. They also learn how to make strategic and tactical decisions under the guidance of mentors and they apply what they have learned in their coursework in a real-world setting.”

Chessler and Libaers also stress the value the students gain from the hustle program’s built-in accountability factor, as participants report to Chessler Holdings’ board and key stakeholders.

Students make all operating decisions during hustle. Foods are pre-selected, so only certain products can be put in the vending machines, and there are expirations dates. As an existing business, ART has taken out guesswork and a bit of risk, as all products in the kiosks ­— Reis & Irvy’s frozen yogurt and hot-serve foods such as pizzas — are from a national food supplier, says Chessler.

Chessler believes the most successful teams in hustle will not necessarily be those with groups of friends, but instead will be composites of varied skill sets. His goal is not to make money on this student program, he says, but to pay it forward on his knowledge of what it takes to start and run a sustainable business.

‘Find what you love, something that doesn’t feel like work.’ David Chessler, Chessler Holdings

With a background in software development, Chessler previously helped build Sarasota-based GPS Industries into a national leader in selling high-end GPS systems for low-speed vehicles, primarily golf carts. He’s since invested in or helped a slew of business, from cannabis to home decor. Chessler has also invested in commercial real estate, and along with two partners, sold a portion of Main Plaza in downtown Sarasota last December for $20 million. An apartment complex is being built on that site.    

With his experience has a backdrop, Chessler hopes to help hustle participants navigate all kinds of business challenges — including what kind of business to pursue. “Find what you love,” he says, “something that doesn’t feel like work.”