Upon graduating from Anderson High School, Reynolds attended Indiana State College and Oberlin College in Oberlin, Ohio. He was later named supervisor of music for the public school system in Kansas City, Kansas. After his four-year tenure at Anderson High School, William H. Jackson graduated from Michigan law school and served as secretary to Booker T. Washington for several years.
Other early black graduates of Anderson High School include Druscilla Mallory, Erline Chandler, and Jeannette Montgomery. Mallory and Montgomery both earned teaching degrees from Ball State Teachers College. Miss Mallory was principal at South Side School in Elkhart, and later taught at the University of Chicago. Miss Montgomery taught in Virginia and for Indianapolis public schools.
In 1905, Mrs. C.E. Palmer founded an industrial school for young black girls. The first meetings were held at the Second M.E. Church on Delaware Street. In order to graduate from the industrial school, the girls were required to design and make a shirtwaist garment. Twenty girls graduated from the inaugural class, including Ida Watkins Montgomery, who was selected to teach at the school.
After the death of her husband, Mrs. Palmer was forced to close the school, but not before teaching her students hands-on skills that led to future employment for many of her graduates.