In 1960, using $5,000 of his savings, and a $95,000 loan, he bought a small drugstore, University Pharmacy on Hillcrest Avenue, across from the campus of Southern Methodist University. Before Simmons owned it, University Pharmacy was the site of a racially charged sit-in in January 1961, when its owner C.K. Bright sprayed insecticide over and around 60 students, only two of whom were black seminary students. Simmons purchased the store and parlayed it into a chain of 100 stores, which in 1973 he sold for more than $50 million, to Eckerd Corporation. This launched his career as an investor, when he used the proceeds of that sale to begin speculation in the financial services industry. By 1974, he had been indicted for and acquitted of wire and mail fraud, and involved in a pension-related lawsuit brought against him by the United Auto Workers.