Seeking a greater education, Richmond traveled to Chicago and attended school at the University of Chicago for a period of time.
In 1894 after years of drought, the family moved to Fort Madison, Iowa. In Iowa Richmond became fascinated with outdoor life and would often travel around with migrant workers listening to their stories and preaching the gospel. Richmond was active in the Boy Scouts of America and started many Scout troops in his travels around the Midwest.
Richmond joined the (Advertising Educational Foundation) American Expeditionary Force and was stationed in France during After the war, he stayed in France and spent one year attending the University of Toulouse.
During that time period, he also helped establish one of the many libraries at the University. After returning to the United States after, Richmond worked as a newspaperman and wrote radio plays.
After several years he grew disenchanted with the life of the big city and its focus on material possessions. Having spent much of his youth being involved with the Boy Scouts and his love of the outdoors, he read the story "The Shepherd of the Hills" by Harold Bell Wright and an article by Horace Kephart about camping in the Ozarks.
These books greatly influenced him and he decided to give up the big city life and find himself again in the hills of the Boston Mountains in Arkansas.
Richmond migrated to Springfield, Missouri, in the Missouri Ozarks. While in Springfield, he continued his education and attended what is now known as Missouri State University. In 1931, Richmond relocated to Mount Sherman, Arkansas, and homesteaded 160 acres (065 km2) land located on the north slope, in what he called "the cove".
He built a cabin which he lovingly called the "Wildcat Cabin" because of the bobcat that followed him on his journey to locate a suitable building site.
Richmond immediately formed a kinship with the native Arkansasans. Richmond was a worldly man in a land that saw very little of the outside world.
He began several quests that were dear to his heart, doctoring and education. He began writing people describing his need for books and magazines that offered reading material of the hill folks.
Richmond married Edna Garner, Chief Deputy Clerk of the Courts of Civil Appeals of the 6th Supreme Judicial District Court of Texas at Texarkana, in 1953.
They lived in Texarkana and Richmond would spend summers on Mount Sherman in Arkansas tending to his Wilderness Library. Richmond died in a nursing home in Texarkana, Texas, at the age of 85. He is buried in a Texarkana, Texas cemetery.