Gaither grew up in Muncie, Indiana attending Burris Laboratory School and Ball State University. He began his professional career as operations manager at a radio station (WLYV) in Fort Wayne, Indiana and was subsequently promoted to general manager within his first year. After managing the radio station for a decade, Gaither relocated to Cincinnati, Ohio to manage two radio stations (WCVX & WQRT). Shortly after his relocation, he was promoted to regional manager, becoming responsible for five radio stations (WCVX, WQRT, WCGW, WJMM, & WLRT), with three offices, in two different states. As a manager, Gaither oversaw many areas of the business, such as IT, staff, marketing, webmaster, client and listener liaison, sales manager, and more.

While managing the radio stations, Gaither continued his education, earning an Associate of Science degree in Computer Science and Information Systems from Purdue University in May 2006 and a Bachelor of Science degree in Business Administration from Indiana Wesleyan University in August 2013.

After eight years in Cincinnati, Gaither, along with his two children, Gaither and Peyton, moved to Florida in February of 2015. While running his own consulting company, Gaither continued his education, ultimately leading to the completion of a Master of Science degree in Computer Information Systems with a concentration in Database Management and Business Intelligence from Boston University in May, 2016.

From October 2016 through June 2017, Gaither was a data analyst/systems administrator for the Homeless Coalition in Charlotte County, Florida.  While at the Homeless Coalition, Gaither maintained local IT, IS, and the HMIS/CIS database.

Gaither is currently Chief Technology Officer at the Gulf Coast Partnership where he performs IT, IS, data analysis and visualization, and HMIS/CIS database duties including administration, maintenance, and user training.