The research intends to explore the behavior of several entrepreneurs in managing their finances in smallmedium businesses. Many have studied financial problems in this type of business with the quantitative method, but only few analyse those problems using the qualitative approach. This paper presents some observation and interviews with nine women entrepreneurs based in West Java, Indonesia. Out of twenty entrepreneurs only nine provide sufficient information, and so the research focuses on these nine entrepreneurs. This research continues the previous one which used the quantitative method. The previous research found that economic capital is the significant factor for business sustainability while habitus and environment were not. However, these results do not provide any comprehensive and complete analysis quantitatively. This time around the research makes use of the qualitative approach whose focuses are on group discussion and transcript analysis. The transcript and the result of some observations have been analysed and interpreted employing Bourdieu’s theory of habitus and capital.The research shows that despite the previous findings, habitus in the form of entrepreneurial tacit knowledge is the most significant matter for old players to get their benefit, while cultural capital in the form of high education, and social capital in the form of network are the most significant factors for young entrepreneur to succeed.