Over the past 22 years, Ryan has served in numerous administrative leadership positions at five different independent schools. At these schools, Ryan has worn many hats, which include serving as Head of School, Upper School Director, Director of College Counseling, Admissions Officer, Teacher and Coach. Born in Vermont, Ryan stayed in New England to attend Colby College where he majored in psychology and was an honorable mention All-American in football. After graduating, Ryan worked at The Kent School for several years before heading to the University of Denver to complete his master degree in education. Falling in love with the West, Ryan stayed in Colorado and worked at Vail Mountain School, a K-12 independent day school. Ryan then worked at The White Mountain School, in Littleton, New Hampshire, directing their college counseling program and contributing to their leadership team. Ryan drew upon his diverse independent school experience by helping start and lead Tahoe Expedition Academy's Upper School as the Acting Head of School and Upper School Director. Ryan then led a ski academy as their Head of School for two years before deciding to start a gap year program for young adults that focuses on leadership development, real-world experiences, service work, and spiritual development.