Randy was born and raised in St. Louis, Missouri. Randy excelled at sports in high school as he was a three sport athlete, playing football, basketball, and tennis. In high school, he was named all-conference in football before he went to play defensive back at the University of Iowa.

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Previously, Randy worked for Bank Trust companies for over 20 years as an Investment Portfolio Manager and managed Bank Mutual Funds. He also worked in brokerage firms as a corporate bond trader. Randy also managed Bank Holding Company Municipal Bond Portfolios and has been featured in the Wall Street Journal "Heard on the Street" column.

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Outside of his professional life, Randy was the President of Roundtable of Missouri, an organization of bankers and brokers. Randy, in his previous capacity as a Bank Trust Officer, has also volunteered as a financial advisor to the Investment Committee of Boys Town of Missouri.

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Randy gave up the cold winters of St. Louis, Missouri for the sunny and warm weather of the Virgin Islands, which is where he currently calls home.