In the early 1950s, he entered City College of New York, majoring in corporate finance, but dropped out after less than two years. He joined the U.S. Army and started working as a court stenographer on Wall Street, where he set his sights on making his fortune. After leaving the Army, he worked as a mortgage broker and investment adviser and soon made his first fortune. In the early 1960s, he moved back to Boston and invested in various companies, among them a travel and tour business, The American International Travel Service, which was very profitable. However, his success turned sour in a stock market decline in the late 1960s.