Born in Los Angeles, raised in Seattle, Blair became obsessed with playing guitar and songwriting in high-school, but at 18 was recruited into the Army as a military intelligence analyst with the idea of moving into the CIA. After years in Cambridge, England on special assignment he left the intelligence community, became and anti-war advocate, leading a local chapter of Iraq Veterans Against the War. He traveled through the pacific then worked on vineyards and herded sheep in New Zealand before taking a job as a tour guide in Skagway, Alaska. If was there he fell in love with performance and comedy. After guiding both land and river rafting tours in Alaska he went to Western Washington University, earning a Philosophy degree. In his senior year he took improv courses from Ryan Stiles' Upfront Theatre and co-starred in an HTC commercial, then was on Comcast's Wanted: Adventure Host. Soon after Blair moved back to Europe and played the lead in over 30 commercials produced in Prague and Amsterdam. Upon leaving Europe he traveled through East Africa then Latin America for nearly a year before returning to Los Angeles.