In 1993, Nan began teaching at the DePaul School for Dyslexia in Dunedin, FL. That same year she started her son, as a first grader, at a local Montessori school. Through her work with children at DePaul School for Dyslexia, she realized the value of the Montessori approach in reaching children with different learning styles. In 1995, she obtained her Early Childhood Credential with the American Montessori Society for ages 3-6 through the Northeast Montessori Institute. In 1997, she began working at the Safety Harbor Montessori Academy, where her son attended. She remained there until 2001, serving as the reading specialist, and doing private consulting work.

Having roots in Western North Carolina, Nan and Steve Gregory then decided to acquire Asheville Montessori School in 2001. The original campus, on Julia Street, had 1 room, 16 children, and 1 employee that first year. Through consistently presenting the Montessori method and demonstrating to parents the importance of early childhood education, their waiting list grew to over 60 families in just 3 years, so they decided to expand. The current campus, in Woodfin, NC, was completed in 2006, and has been a haven for Montessori peace education ever since.

In 2022, their son, Phil Gregory, decided to join the school full time to help his parents transition into retirement. Nan still consistently comes in to volunteer and read with the children. The school is currently owned by Phil and Leigh Gregory. Phil is the full time operator, but Leigh isn’t involved in the day to day, as she has her own career as a speech pathologist for Asheville City Schools. They are diligently working to uphold the legacy of Montessori education, started by Nan and Steve.