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Miles was raised in the Tawas area and graduated from Tawas Area High School in 1991. He then earned a Bachelor's degree from Central Michigan University in 1996. After spending seven years in Lake Tahoe, California and Amelia Island, Florida, working in the hospitality industry, he moved back to East Tawas. Although new to Real Estate, he did own and operate a Mortgage business in East Tawas for five years.