In 1955, Robert Ryan Sr. opened his own used vehicle agency in Sioux Falls, SD, operating as Mid Town Motors. In 1965 he was awarded the Rambler & Mercedes franchises and ultimately the Chrysler & Plymouth franchises. In 1966, Robert Ryan Sr. built and opened Ryan Motors in Sioux Falls, SD operating as Ryan Motors Chrysler Plymouth. In 1971, Robert Sr. moved his family to Texas after selling his automobile interests. Robert Sr. and his family moved to Houston and operated Midtown Chrysler Plymouth for one year. In 1975, the Ryan family sold out and returned to the Midwest, where most of the 14 children and 22 grandchildren reside today. In 2011 the Ryan family opened Ryan CDJR of Buffalo, followed in 2018 with Ryan CDJR of Monticello.