Wilson began his career as a commercial land broker in Dallas, TX in 1984. In 1988 he moved to Memphis, Tennessee to join the Weston Companies (formerly Vantage Companies). Wilson was promoted to vice president and managing director of the company’s Nashville Retail Division in 1997. While at Weston, he leased more than 1.5 million square feet of retail space and was involved in the development or redevelopment of more than 2.5 million square feet of retail shopping centers. After Weston, Wilson formed Smith Crowe Wilson, LLC, which he helped grow to 70 employees with management of more than 6 million square feet of retail space in less than three years.