James Eads How, The Millionaire Hobo

In addition to advocating for hobos, How chose to live as one, even though he had both money and education. He wore a shaggy beard and rough tramplike clothes. It was said that even ordinary hobos looked well dressed compared to How.[3] From about age 25, he traveled around doing hard work for a living.[11] One of How's contemporaries, sociologist Nels Anderson, describes how fully How immersed himself in the hobo lifestyle and how seriously How took his work:

Millionaire that he is, How has not failed to familiarize himself with every aspect of tramp life. He knows the life better than many of the veteran hobos. He has become so thoroughly absorbed in the work of what he describes as organizing the "migratory, casual, and unemployed"...workers that he practically loses interest in himself. He becomes obsessed with some task at times that he will walk the streets all day without stopping long enough to eat.