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Gregory was born in Kansas City, Missouri, in 1986 and moved to Colorado at an early age. During his childhood, he attended a Waldorf school where he discovered a love of painting, sculpture, music, and the natural world. He continued to develop his skills as an artist and musician throughout high school and painted whenever he could while earning his BA in biology at Colorado College. As a student, he made a conscious decision not to take any painting courses or adopt a mentor, opting instead to learn through experimentation and scrutiny of paintings by artists he admired. After graduating in 2009, he devoted his studies to painting and has since gained recognition as "one of the most promising young artists in the representational art world" (Fine Art Today). He lives in Denver, Colorado.