At the age of seventeen he left home to become a common seaman; after returning to the United States he traveled across the country by riding the rails as a hobo.

[10] He spent much of his maturity traveling; he stayed in a number of planned communities for varying lengths of time, then wrote autobiographical novels about his experiences.

Kemp had a knack for self-promotion, what he called "the Art of Spectacularism,"[13] and early learned to collaborate with and manipulate journalists to attract attention to his work.

Kemp was physically imposing, "Tall, broad-shouldered, and robust,"[15] and gained a reputation as a lover, sometimes of other men's wives; he was involved in various scandals throughout his career.

In addition to his original books, Kemp translated a play by Tirso de Molina as The Love-Rogue (1923), and edited The Bronze Treasury (1927), "an anthology of 81 obscure English poets."

Kemp's views turned somewhat more conservative with age; he rejected leftist and anarchist sympathies and wrote approvingly of Jesus as the "divine hobo" and the "super tramp."