Gilmore was a Canadian foreign service officer who began his career in Jakarta. From that post he covered the civil war resulting from the Indonesian occupation of East Timor, and later joined the United Nations Transitional Administration in East Timor (UNTAET) peacekeeping mission under Sergio de Mello. In that role he became disillusioned with ineffective donor efforts to fight poverty. Based on this experience he quit his job as a diplomat in 2004 to launch the non-profit Building Markets. and focus on capitalism instead of aid as a sustainable poverty solution.