Winston, who grew up in Raleigh and attended Enloe High School and Wake Tech Community College, relocating to New York City at 21 to pursue his education at the School of Audio Engineering. For a decade, he served as a sound engineer and production manager for various live events worldwide, including concerts and theater productions, having traveled to 37 countries during his touring career. Winston was inspired by the strength of community he witnessed across diverse cultures, prompting him to return to his hometown of Raleigh to contribute to its growth and development.

In 2021, Winston became a member of the Trademark team with a mission to expand the company’s retail and medical departments. Winston has been a vital asset in investment sales, retail QSR site selection, medical office leases, and the installation of EV charging stations at shopping centers across North and South Carolina.