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Howard Wilner began their work experience in 1989 as the President of Automax Preowned, the largest independent dealer in New England. Automax specializes in selling one owner clean late model Foreign and Domestic vehicles, with 6 locations in Massachusetts and employing 80 people. In 1995, they became the President of Mina Property Group.

Howard Wilner attended Massachusetts Bay Community College from 1984 to 1986, where they earned an Associate's degree in Business Administration and Management, General. Howard then attended Boston College from 1986 to 1987, although the degree name and field of study are not specified.