When Willie was eight, Rachel Boone married Harrison Hendricks and moved into his home, which sat "just back of the old Land Fike's Mill [Eureka Mills] on Mill Street." Melissa Fuell Cuther noted: "The house was a one-room log cabin, with the old puncheon floor; very scantily furnished." It was a very active household because when Boone and his mother moved in, Harrison had five step children to greet them.
Boone organized a neighborhood band that included two tin whistles, a mouth harp, which was essentially a harmonica, and a triangle and they played on the streets of Warrensburg. By this point, Boone's talent for music had already caught the attention of some of Warrensburg's leading citizens and it was through their efforts that they raised money to send him to the Missouri Institute for the Education of the Blind in St. Louis. He became one of six black pupils at the school and he was admitted to the school in October of 1872.
The Missouri Institute for the Education of the Blind in St. Louis provided Boone with an opportunity for manual training as well as training in music. Boone enjoyed the music training and he learned to play the piano by ear, but the manual training pushed him away and he began to sneak out of his school and made his way to St. Louis's "tenderloin" district located around Franklin Avenue and Morgan Streets where he enjoyed the vibrant music. He was expelled from the school in 1874 and he returned to Warrensburg.
In Warrensburg the Foster School hired him to play music as the students marched from their classes. He reorganized his band and in the spring and summer they played at picnics, circus grounds, and fairs. He met a white man named Mark Cromwell and he offered to manage his first concert tour, but Cromwell stole the proceeds that he collected on Boone's behalf and then he gambled Boone away to another person named Sam Reiter, who promised to promote his career, but then Cromwell stole him back and essentially made him perform at Centralia, Mexico and Ladonia.
Boone's family, including his step-father, began searching for him and finally caught up with Cromwell at Ladonia and took Boone home after he performed at Vandalia. He returned to playing on the streets of Warrensburg, but quickly ran away and began playing music for money on the trains that traveled across the state. Melissa Fuell Cuther noted in her biography: "He liked to walk up and down the aisles of the big trains, play his harp and sing funny songs."
Boone met Tom Johnson, a banjo picker from Sedalia and Ben Franklin who was a "Tea Cup Artist." According to Jack A. Batterson, a "tea cup artist" plays a harmonica and covers it with a tea cup to produce a unique sound. The trio traveled around the state of Missouri where they showcased their talents. They had agreed to split their earnings three ways, but at one stop Boone received more money than the others and he refused to split the money with the other two and he parted ways with them.
Willie stayed in Glasgow and Fayette where he played in churches and completed a concert tour of several churches in Iowa before John Lange sent Rev. Mr. Stewart from the Baptist Church in Columbia to bring him to the city to play for the Annual Holiday festival in 1879.
In 1880 John Lange founded the Blind Boone Concert company, with Boone as its principal performer and he remained his manager until his death in 1916.