In this interview former Army Captain Keith Weinstein (class of 1999) discusses his path to West Point, his experiences at the Academy, and his decision to become a Signal Officer. He discusses his deployments to South Korea, Afghanistan, and Iraq, his decision to transition out of the Army and subsequent professional path to becoming a network engineer at Google. In this candid interview, he pulls no punches when it comes to Army talent management and retention as well as the red tape and bureaucracy that so often plagues the Department of Defense. He contrasts the Silicon Valley culture and business process with that of the Department of Defense and the larger military industrial complex, suggesting that the latter has much to learn from the former.