On account of multiple causes, including prolonged global economic crisis, addressing environmental pollution and the advent of hyper-connected society, a new paradigm called 'sharing economy' has rapidly emerged. Many startups have attempted to build promising business model based on the sharing economy concept. Nevertheless, successful cases are still very rare in the global level, except for Uber and Airbnb cases. Therefore, this study analyzes necessary causes and sufficient causes for successful settlements in the market through a comparative case analysis on digital matching firms in the sharing economy businesses. For the case study, we compare five successful cases (Uber, Airbnb, Kickstarter, TaskRabbit and DogVacay), three failure cases (Homejoy, Ridejoy and Tuterspree) and a platform cooperativism case (Juno) in accordance with six value attributes of business model including value proposition, market segment, value chain, cost structure and profit potential, value network and competitive strategy. We apply Boolean method to support controlled comparison and eliminate unnecessary attributes. The Boolean analysis result shows that value proposition, cost structure and profit potential, value network and competitive strategy are the essential attributes. Furthermore, the result indicates that each attribute is a necessary condition, where all four conditions should be met simultaneously in order to be successful. With this result, we discuss essential consideration for those who are planning startup based on the sharing economy business model.