He first came to public attention as part of the winning team, together with his friend Chris Luca, in the second season of the reality TV show The Amazing Race in 2002.
[3][4] During his time in Jacksonville, Boylan played soccer where he helped the team win the conference tournament while making a run to the NCAA Division 1 Sweet Sixteen.
[6] in January 2002, Boylan competed on the second season of the CBS adventure reality show The Amazing Race with his lifelong friend, Chris Luca.
During this time, he hosted numerous television shows, including At the Chef’s Table (2004), a food series on PBS.
[9] Other shows include Jeff and Jordan Do America, the Buzz Tour for CBS, Rach to the Rescue for The Rachael Ray Show, Tales from the Trail for The Boy Scouts of America, Missions in Action, and destination content pieces for Travel Channel and Lonely Planet.