Penn Holderness was born in Durham and attended Durham Jordan High School, where he played basketball.
Penn went to college at the University of Virginia and majored in philosophy, but took a crack at journalism after graduation as an intern for the WTVD ABC11 sports department.
His first on-air job in was in Grand Junction, Colo., then Penn moved to Orlando for five years. Penn hosted three seasons of "Designer Finals" on HGTV and hosted a college hoops show on CSTV with former Tar Heel Coach Matt Doherty. Most recently, Penn worked as a video essayist for ABC and ESPN while living in New York.