He later went to Oxford and joined George Bernard Shaw's Fabian Society, at which time he also became a vegetarian (which he remained for the rest of his life).

How felt morally obligated to put his wealth to good use—going so far as to state of his fortune, "I have not earned it, it is not mine"[7]—and he chose the homeless as the population he would dedicate his money and his life to organizing and advocating.

[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 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.Central to How's work was his brainchild, the International Brotherhood Welfare Association (IBWA), a sort of union for the hobos with headquarters in Cincinnati.

[3][4] The hobo colleges, which How started in several cities, primarily offered lodging and meals, but as the name implies also education and a place to meet.

[4] The education would be scheduled certain nights and included basic lessons in social science, industrial law, public speaking, job searching, and anything else that might be understood and useful for the hobos.

[17][18] According to contemporary sociologist Nels Anderson, How had almost complete control over the IBWA and Hobo News, at least in the beginning.

This was not because he sought power—he had strong democratic ideals and gave individual "colleges" and other projects much management sovereignty—but rather because of his money, which was often needed for new ideas or to cover for financial problems.

As IWW was increasingly broken many of its members joined IBWA, leading to both radicalization and faction conflicts.

How was on the moderate side and preferred the IBWA to focus on education and more immediate political issues like abolishing vagrancy laws, rather than direct action and sabotage.

[14][20] How was chairman of the National Committee for the Relief of the Unemployed in New York but went back to St. Louis in 1908, after disagreeing with other leaders.

[21] In 1914, How led a group from the IBWA in New York to join the second Coxey's Army protest march to Washington, D.C.[22] At 50, How married and moved to Los Angeles in the 1920s with his wife Ingeborg Sorenson.

[27] In July 1930, How fainted in Cincinnati Union Station and was taken care of by his friend and attorney Nicholas Klein.