Wess is originally from Memphis, Tennessee. He moved to Southwest Florida with his family as a child. He graduated from Bishop Verot High School in Fort Myers. He attended the University of Florida where he graduated with a Bachelor of Science degree in Business Administration. He was then accepted to the University of Mississippi College of Law where he obtained his Juris Doctor degree. Wess is a member of the Florida Bar and is also admitted to practice in the federal Middle District of Florida. He began in general private law practice and has remained in Southwest Florida where he and his wife have raised three children together. His practice areas include Estate Planning and Probate, Guardianship, Contracts, and Business Formation. He enjoys walking with his wife and travelling with his family. Throughout his life, Wess has enjoyed coaching football and basketball for middle and high school teams in the area.