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Collier's entrepreneurial journey took off when he recognized the potential of streetcar advertising. He secured a contract for exclusive advertising rights on Memphis's horse-drawn streetcars. Understanding urban transportation trends, he tapped into a captive audience, eventually expanding into markets across New York and other major U.S. cities. By age 26, he had made his first million and launched multiple business interests, including hotels and amusement parks, befriending some of the wealthiest figures in America.