This paper employed exploratory data analysis or data mining to determine the problematic factors that will characterize the common concerns of business investors in the ASEAN countries. More specifically, the researchers grouped and categorized these factors that had affected the current condition of businesses and determine their effect on the extent of doing businesses among ASEAN member states. Factor analysis has identified three factors, namely, legal and judicial climate, economic climate and labor climate. These factors were used as bases to determine the extent of problematic factors of doing businesses in an ASEAN country through a model obtained using principal components analysis. With this model, the overall results revealed that Singapore emerged as the most enticing place to do business among the ASEAN member states. This finding is mainly due to the positive opinions Singapore received in terms of legal and judicial climate and labor climate. On the contrary, Thailand is considered as having the most problematic variables in investing business as revealed by the study. This is largely due to the recent political turmoil it experienced in the late 2013 up to mid 2014. With the identified problems these ASEAN nations face based on the above-identified factors, it can be concluded that ASEAN nations should come to terms in identifying their strengths and weaknesses before considering the idea of integration. This is to ensure that business investors that ASEAN nations can address these pressing problems especially in factors that business executives see.This action has to happen to help them welcome more investors and to create a business environment more conducive to progress.