Starting in banking and quickly recruited to a hedge fund, Winston worked as a portfolio analyst. He then moved to consulting and specialized in finance, branding, and marketing. Initially taking on Stevie as a branding side project, Winston grew passionate about the company during the building process. Soon they officially started up the fashion company. Winston is a graduate of West Point.

Out of highschool, Steven starte working as a Department of Defense employee while modeling part time. Seeing a lack of creativity in what he was modeling, Steven started designing clothes and accessories. Immidiately noticed for his designs, Steven started his designer persona, Stevie Boi. Multiple awards and A - List clientel later, he is one of the hottest designers in the industry.