Medley gained interest in business and non-profits at a young age, starting his first business at the age of 15. Since then Medley has bought, sold, and founded more than 6 companies and non-profits. MB Group, The Old Bike Shop, Launch Cooperative, and Front & Center Theatre, Inc. are among his entrepreneurial ventures. Currently, Medley is Owner and Creative Director of MedleySites; President of Beverly Homecoming, Inc.; Board Member, Greater Beverly Chamber of Commerce and Marketing Director of the Beverly Farms Improvement Society.
In 2012 Medley was nominated for the Beverly Chamber of Commerce’s “Young Entrepreneur of the Year” award which he went on to win in 2013. In 2020 Medley was nominated for the Greater Beverly Chamber of Commerce's "Sole Proprietor of the Year".
A broadly engaged community citizen, Medley is passionate about music and the performing arts. He is a resident of Beverly and relishes life near the ocean.