Ivory arrived in Delaware in  October of 1904 to begin his training with Pyle. Having already  mastered the fundamental of figure drawing, he progressed quickly  under Pyle’s instruction. By the autumn of 1905, Pyle was writing  letters of introduction for the young artist to the editors of  McClure’s Magazine and Collier’s Weekly, urging  them to consider Ivory’s work. Like many of Pyle’s pupils, Ivory  launched his professional career from the Pyle student studios  at 1305 Franklin Street. In 1906, he received a major commission  from the Saturday Evening Post to illustrate Joseph Conrad’s  Mexican adventure tale, Gaspar Ruiz. Ivory had visited  Mexico in 1904, and he was able to give his illustrations authenticity  by relying on photos and costumes he had collected on his trip.  Authenticity remained a key issue in his work, and he amassed  a large collection of antique furniture, clothing, and guns to  use as studio props.

Many other commissions followed  Gaspar Ruiz, enabling Ivory to publish his work in most  of the leading magazines of the period. Specializing in Western  scenes, he caught the excitement and violence that characterized  contemporary writers’ visions of the old West. His pictures also  accompanied stories about the Far North, including several by  Jack London. By 1909, Ivory had left the Pyle studios and, along  with three other Pyle school alumni – W.H.D. Koerner, E. Roscoe Shrader, and Herbert Moore – set up a studio in the old Robinson house in Claymont, Delaware. There, the “four horsemen of  Naamans”, as Shrader later called the group, pursued their  professional careers. In 1915, Ivory and his wife spent the summer  in California, Alaska, and the Yukon, where the artist took many  photographs of the region as studies for later illustrations.

Although Ivory maintained a studio  in Philadelphia for a short period in 1913 and 1914, he did most  of his work in Wilmington until 1918, when he moved to New York  City. There he joined a group of artists based in the Studio  Building at West Tenth Street, and, in the company of artists like photographer G.W. Harting and writer-painter Kahlil Gibran,  Ivory continued his efforts. By this time, however, the popularity  of illustration was declining. Fewer and fewer commissions came  Ivory’s way, and, with the onset of the Depression, his career  was cut short. Although Ivory later painted for personal enjoyment  after the traumatic effects of the Depression subsided, he no  longer supported himself through his art.