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Aaron Gray, founder of The Legacy Movement, at the Chicago Cultural Center in Chicago, Ill., on Friday, October 5, 2012. | Andrew A. Nelles~Sun-Times Media
Aaron Gray, founder of The Legacy Movement, in downtown Chicago, Ill., on Friday, October 5, 2012. | Andrew A. Nelles~Sun-Times Media
Aaron Gray, founder of The Legacy Movement, in downtown Chicago, Ill., on Friday, October 5, 2012. | Andrew A. Nelles~Sun-Times Media
Aaron Gray, founder of The Legacy Movement, in downtown Chicago, Ill., on Friday, October 5, 2012. | Andrew A. Nelles~Sun-Times Media
Aaron Gray, founder of The Legacy Movement, in downtown Chicago, Ill., on Friday, October 5, 2012. | Andrew A. Nelles~Sun-Times Media
Aaron Gray, founder of The Legacy Movement, in downtown Chicago, Ill., on Friday, October 5, 2012. | Andrew A. Nelles~Sun-Times Media
Aaron Gray, founder of The Legacy Movement, in downtown Chicago, Ill., on Friday, October 5, 2012. | Andrew A. Nelles~Sun-Times Media
Aaron Gray, founder of The Legacy Movement, in downtown Chicago, Ill., on Friday, October 5, 2012. | Andrew A. Nelles~Sun-Times Media
Aaron Gray, founder of The Legacy Movement, in downtown Chicago, Ill., on Friday, October 5, 2012. | Andrew A. Nelles~Sun-Times Media
Aaron Gray, founder of The Legacy Movement, in downtown Chicago, Ill., on Friday, October 5, 2012. | Andrew A. Nelles~Sun-Times Media
Aaron Gray, founder of The Legacy Movement, in downtown Chicago, Ill., on Friday, October 5, 2012. | Andrew A. Nelles~Sun-Times Media
Aaron Gray, founder of The Legacy Movement, at the Chicago Cultural Center in Chicago, Ill., on Friday, October 5, 2012. | Andrew A. Nelles~Sun-Times Media
Aaron Gray, founder of The Legacy Movement, at the Chicago Cultural Center in Chicago, Ill., on Friday, October 5, 2012. | Andrew A. Nelles~Sun-Times Media
Aaron Gray, founder of The Legacy Movement, at the Chicago Cultural Center in Chicago, Ill., on Friday, October 5, 2012. | Andrew A. Nelles~Sun-Times Media
While Chicago’s startup cheerleaders trumpet rapid-fire business launches, South Side native Aaron Gray is working to empower the underserved, overlooked and unconventional businessperson to think about a variety of options. Gray, 31, has started The Legacy Movement to upend the conversation about business startups: He …