Dr. Obadiah Howard was born in Tennessee in 1860, so it is likely that he was born into slavery. His wife, Elizabeth Hyde Howard, was born in Missouri in 1862, so she was possibly born enslaved as well. They were married in 1888 in Des Moines, Iowa, and the first of their two daughters was born in Minnesota in 1890. 

Howard's profession in 1900 was listed as "barber," in 1910 it was listed as "physician," and in 1920 he was listed as an "osteopath." In 1930, a widower at the age of 80, he was back to barbering. Howard's daughter Ethel married Stephen Maxwell, who may have been Howard's barbering partner, in 1910. Their son, Howard Maxwell, is pictured here with his grandfather at the age of about two.