Randy earned a BA in Biology from Virginia Military Institute in 1987 while competing on the track team. After graduation he served in the army as a Military Air Defense Artillery Officer. Having later earned a JD from the University of Richmond in 1994, he went on to earn a MSc degree in International Shipping and Maritime Law from the University of Plymouth (UK) in 1999. Randy accepted a position in operations and logistics for Belgian Overseas Chartering and Shipping (BOCS). In 2005, he led a managed buyout of its principal BMS, expanded its operations and sold the companies in 2009. Soon after he became an equity partner in Balaton Park Entertainment Resort. He and his family reside in Santa Barbara, CA, having formerly lived in Europe from 1999-2019.