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Barry graduated from Miami University in Oxford, Ohio, where he received his bachelor's degree with two majors - Russian Language and Culture & Diplomacy and Foreign Affairs. After graduation, he moved to Moscow where he worked as an import warehouse manager and also as the director of business development for the sole distributorship of Apple computers in Russia. In Prague, he was a financial analyst for two different distributorships - one in Prague and one in Kiev. Following this adventure, he graduated from Valparaiso University School of Law and is a litigation attorney for the past 18 years. During Covid, he completed his master's degree in history at Liberty University and is in the process of finishing his PhD with a focus on totalitarianism in the 20th century.