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Waylan's artistic journey began in childhood, inspired by superheroes like Superman, historical figures like Davy Crockett, and Western icons like Roy Rogers. Drawing became a vital outlet for his creativity.

His educational path at Virginia Tech involved exploring architecture, where he honed his drawing and painting skills. Early in his career, he engaged with both traditional and conceptual art. At the Rhode Island School of Design (RISD), he earned a degree in printmaking and co-founded the P. Dora Gallery.

Two decades ago, Waylan shifted to creating intuitive, introspective work, stepping away from public exhibitions. His journey spans over five decades, showcasing his dedication to his craft.