[2] Pressley attended A. C. Reynolds High School in his hometown of Asheville, North Carolina, where he played American football as quarterback for four years.

[2] Pressley was a walk-on quarterback for the NCAA Division I North Carolina Tar Heels football team beginning in 2010.

Pressley played two games in total before leaving on exchange at the University of Edinburgh in 2014 and retiring immediately upon his return.

[3] Pressley received national attention with his role as "Supervisor of Morale" for the North Carolina Tar Heels football team.

In 2016, he launched the Dixie Tour with Barstool Sports, a project providing coverage of college football across America.