Gillett has been a member of the Sunny Hollow community since 2003 when his oldest daughter Libby joined Casa Creek. He has served in many capacities at the school, including chair of the Great Gala and Board Trustee and Chair. Gillett received his Montessori Elementary diploma from the Montessori Training Center of Minnesota in 2012. He enjoys photography and the outdoors. He loves to sail, rock climb, camp and lap swim (especially in open water). He lives in St. Paul with his wife, Lynne, and two daughters, Libby and Katharine.