The Male Mogul Initiative, led by former NFL football player Walter Mendenhall, in partnership with Entrenuity, completed its second cohort with high school students from the Austin Community, located on the Westside of Chicago, using the StartingUp Now curriculum. Students gained practical and applicable knowledge about business creation that can lead to success and productivity in their businesses, schools, and community. We accomplished our task by helping students develop and enhance their personal philosophy of leadership that included an understanding of self, groups and how they can be positive change agents in their communities. Students had a chance to visit Northwestern’s Kellogg Business School and present their business plans at the conclusion of the six-week program. The Male Mogul Initiative was rated After Schools Matters' highest rated summer program for the summer of 2017.