In the 1920s, Taylor studied painting with Charles W. Hawthorne in Provincetown, Massachusetts, but turned to lithography in the late 1920s to early 1930s during his enrollment at the Art Students League in New York City.
Prentiss established the Washington Wheat Press as a means for publishing, and within the paper were various poems and illustrations by the artist as well as poems and prose by Josiah Titzell, Rachel Field and Laura Benet.