This article describes the lives of poverty in the context of a specific culture, the Philippines. The goal of this article is to study what it means to be poor and to understand the cultural factors that contribute to this human experience. Two case studies will be presented; one of a Filipino who was born poor and has become materially successful, and another of a Filipino who was born poor and has stayed poor. Interestingly, the two persons are relatively similar in terms of beginning circumstances, education, gender, religion, and age. The discussion will deal with the processes of living in poverty and getting out of poverty. The results will then be discussed in a broader framework of culture and poverty, and intercultural differences between Philippine poverty and the culture of poverty (Lewis, 1959) will be highlighted.