Herman was born in Aschersleben, Germany. He came to the United States in 1861 with his family. He put himself through Fort Wayne College and moved to Milford, Indiana, where he met Henrietta. The couple married in 1885 and moved to Elwood in 1888 when Herman became the Superintendent of Schools. Herman also studied law and was admitted to the Indiana bar in 1890.
Herman and Henrietta's son, Wendell Lewis Willkie, is Memorial #1104.