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This story appears in the December 2020 issue of Entrepreneur. How do you dress for the Pentagon? Most people hoping to secure a contract to send satellites into space would put on a suit. But Ben Lamm is not a fan of the expected. So on a visit to Washington, D.C., the night before his big meeting with Air Force generals, he was at a restaurant deliberating two important style questions: Which jean jacket would he wear? His dinner date that night knew the Pentagon well. It was Susan Penfield, a longtime executive VP at consulting giant Booz Allen Hamilton, which does a lot of work with the federal government (as well as with Lamm). "I don't know if it will fly at the Pentagon," she told him -- but if he insisted on a scarf, she suggested one with all-American red, white, and blue colors. The next morning, Lamm thought, Maybe not and threw on his Alexander McQueen -- black with white skulls.