The Shupe family started a family business in Milford in 2010 called Fur Baby Boutique. Quickly noticing the evolving landscape of the dog industry, the couple expanded their business to include animal services such as doggie daycare, overnight hotel, spa grooming, and grocery. In 2021 Fur Baby Pet Resort opened a 10,000 square foot facility as the business now employs over 15 employees and supported the rehabilitation of a vacant property in Downtown Milford that had been abandoned for over 20 years. The land now known as the Mispillion Gateway leads into Milford's Downtown Development District and hosts two growing businesses.
In 2016 Bryan was elected as the youngest Mayor in Milford's history as he partnered with Bayhealth to reimagine the Sussex Campus that now includes the Bayhealth Hospital and Nemours Sussex Pediatric Campus. His other accomplishments during his two terms include reform of city rental codes that ensured safe housing, major infrastructure rehabilitation that set the city on a solid foundation for future growth, and four balanced budgets that included no tax increases.

In 2018, Shupe was elected to the 150th General Assembly as State Representative of the 36th District. Currently serving his second term, he has pushed reforms for clean water, vocational training, voting rights, government transparency, and budget stabilization efforts.