Jacob “Jester” Massey
Born and raised in Goochland, Virginia, Jacob Massey grew up with a love for football and a dedication to his community. A varsity player at Goochland High School, he balanced athletics with academics, earning his associate’s degree before even graduating high school.
Jacob then attended Randolph-Macon College, where he majored in Business Management, minored in Film, and continued his football journey on the college team, all while making the Dean’s List and meeting his future wife, Gracie.
Today, Jacob and Gracie live in Ashland, Virginia, where they’re raising their twin boys, Milo and Crew. As the founder of Websters LLC, Jacob is dedicated to empowering local small businesses with the digital tools they need to thrive. He also serves as the JV defensive coordinator for Hanover High School, blending his love for football with his commitment to the community.
Outside of work and coaching, Jacob enjoys spending free time with family, hanging out with friends, or catching a football game whenever he can.
