His first jobs were brochures for the National Crayon Company and illustrations for the Boston Herald. His career took off when the New York World arranged to send him to Cuba. He became a sketch artist for important events, his sketches being published in the newspaper in the days before photographs were used. He rose to become the art editor for The World. It was at this time that he started perhaps his most famous comic strip, The Explorigator.
Intended as a rival for Winsor McCay's Little Nemo, The Explorigator concerned the flight of the eponymous airship, headed by a crew of children ages 9–10: Admiral Fudge (who wore a swastika on his hat), Detective Rubbersole, Maurice Mizzentop, Nicholas Nohooks, Grenadier Shift, Teddy Typewriter, and Ah Fergetit. The strip only ran for 14 weeks in 1908, yet its detailed drawings of airships and various other aircraft would later find some fame in the steampunk movement.