In 1998, bored from an early retirement after stepping down from his position as executive vice president of Broder Brothers, Barry used his years of experience to found the Orlando-based apparel development studio, Entertainment Apparel. Having previously worked on the back end of wholesale apparel supply, he was eager to take his industry knowledge and bring it to the creative forefront. He developed presentations and pitched designs to a variety of clients, eventually producing work for Universal Studios, Disney World, and others.

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As Entertainment Apparel grew, Barry's son, Sully, learned the ins and outs of the business firsthand and developed a passion for apparel development. Today, Barry and Sully, father and son, lead a small team in Orlando, servicing apparel needs for clients internationally.