Miles developed an interest in music at an early age, inspired by a mixture of videogame music and Black Sabbath, and began playing guitar when he was 12 years old. He began taking private lessons that originally focused on classic rock before becoming interested in jazz guitar. He studied jazz in the Greater St. Louis metropolitan area for seven years prior to and during his undergraduate studies. While he did not study music through his university studies, he maintained a strong dedication to playing and studying music – primarily focusing on guitar, but also learned to play mandolin and ukulele.

 After spending six years teaching journalism at a university level, Miles decided to switch his focus to teaching and playing music. He teaches using a student-focused, malleable approach, with the understanding that each student has their own strengths, needs, and goals, and tailors his curriculum to each individual, using various exercises and scales to meet these needs. He has been influenced by most genres of music, ranging from early punk music to melodic death metal, and from classical to jazz.