One Smart Cookie

With one of the most successful student businesses in Collegiate history, there is no question Winston Sisk (’18) has a bright future. In Middle School, Sisk began selling cookie cakes to his peers and teachers, which led to the creation of his company, One Smart Cookie. Sisk decided to start making cookie cakes after he struggled to find anywhere in Richmond to buy a cookie cake. His business quickly became popular, his cookies were frequently ordered in Middle School, and eventually One Smart Cookie had to be regulated. The business was forced to run in accordance to school policies, which limited sales opportunities. The steady stream of customers slowly diminished in Upper School, but the business is still running. One Smart Cookie is not all fun for Sisk; although he enjoys running the business, there is plenty of work involved.  

Sisk’s business thrived in Middle School by preying on the hungry students. Many Middle Schoolers would pool money together to pay for the cookie cakes. Whether the money came from their personal savings, their parents, or simply borrowing from a friend, students were happy to pay $10.00 for an entire cake to themselves. Sisk buys the icing and pre-baked cookie cakes in bulk to design and sell for a profit. With each cookie cake bringing in an estimated $6.00 profit, Sisk realized the high demand for cakes among students and began to sell individual slices during advisory, otherwise known as snack time. He would stand in the hallways with a bucket of cookie cake slices and sell each slice for $1. One Smart Cookie would target the Middle Schoolers who forgot their snacks and were willing to give up a dollar for some food. The business maneuver proved to be extremely successful, and Sisk was “surprised at how much it grew.”

At its peak, One Smart Cookie was raking in nearly $1,000 per school year. Customers were purchasing cakes regularly due to their great taste and convenience. Joseph White (‘18) believes the company’s success can be attributed to each cakes “the moistness of the cake, which allows it to melt in your mouth.” With such a high number of daily customers, the school took notice in the business. One Smart Cookie was prohibited to sell slices in the hallways, since it was against Collegiate policy. Shortly after being restricted by the school, the business became part of the Entrepreneur Club and began to focus primarily on selling during school functions. Sisk claims, “The Entrepreneur Club has helped me be able to learn how to handle money quickly and also taught me how to plan and execute large numbers of orders.” Still going strong, Sisk prepares anywhere from 60 to 100 cookie cakes for events and sells nearly all of them. With so many cookies to make, he often receives help from his mother, who enjoys working with One Smart Cookie. She often helps Sisk transport the large numbers of cakes and helps him work the tent during Village Green Fair. Sisk even began to sell One Smart Cookie t-shirts as a form of advertising and to help get his logo seen. Throughout the years, Sisk has taught himself many valuable lessons of how to run a successful small business.

Photo credit: Winston Sisk.

Now a junior, Sisk works harder to balance schoolwork and running the business. He doesn’t find the business to be too distracting and claims, “I just plan ahead and work during the days leading up to the event.” Sisk still earns plenty of money from selling during Entrepreneur Club markets and from his tent during the Village Green Fair. Although individual sales have decreased, he wants to remind customers: “I am still selling and happy to do business.” One Smart Cookie prepares and designs cookie cakes for birthdays, holidays, or nearly any theme requested.

One Smart Cookie prospers at Collegiate partially due to their openness to student-run businesses. Over the years, the business has achieved legendary status and is extremely popular on campus. One Smart Cookie has been running for over five years and, although business has slowed, it will continue to sell throughout Sisk’s time in Upper School. Working as owner, salesman, and chef, he has proven to be a hardworking and dedicated businessman. Thanks to Sisk, One Smart Cookie now serves as an example for any young entrepreneurs interested in running their own business.

About the author

Spencer is a junior at Collegiate. He enjoys the Reading Rainbow, Google-Chatting with ladies, and incorrectly correcting people's grammar,