Cundy was born in 1933 and as an only child, grew up far faster than other children his age. While his friends were out having fun, Cundy was working to help support himself and his mother because of their financial needs. He worked any odd job he could find. He held down at least two jobs every day of his early life.
Near his home, the Work Project Administration built an athletic field and tennis courts, where Cundy got a job maintaining six clay courts for two dollars a week. In the process he learned how to play tennis, which would serve as springboard for future success.
His time spent at the tennis courts helped him become a premier athlete, eventually winning the Kentucky State High School Tennis Championship. His standout play created an opportunity to attend Florida State University on Scholarship. He continued working: washing dishes, being a busboy. He earned a degree.
In 1958, after serving time in the Marines where Cundy earned the rank of Captain, he began working for Prudential, and in less than a year, he sold more than $1 million worth of life insurance. The work ethic he learned early in his life was being rewarded. Provident Life & Accident awarded him a general agency, and Cundy Life Insurance was born.
Over the next 45 years, Cundy built one of the largest privately held employee benefit consulting firm in the nation. Cundy Life Insurance's clients included Anheuser-Busch, Ford Motor Company, Fruit of the Loom, McDonald's and Viacom.
His success hasn't blinded him from his past. Today, he's a major advocate of educational and youth programs in Kentucky, provides equipment and scholarships to students throughout the state, and funded a Holocaust Studies Program at his alma mater.