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Armstrong's career flourished after he moved to Strachan & Company, a leading shipping and freight forwarding company in Savannah. Starting as an employee, he quickly rose through the ranks to become vice president, showcasing his innate talent for business and logistics. His leadership in the shipping industry played a crucial role in transforming Savannah's port into a bustling trade hub—a feat that not only bolstered the city’s economy but also contributed significantly to his personal wealth.