Product Service System(PSS), which is an integrated combination of product and service, provides new value to customer and makes companies sustainable as well. The objective of this paper draws Critical Successful Factors(CSF) of PSS through multiple case study. First, we review various concepts and types in PSS and Platform business literature currently available on this topic. Second, after investigating various cases with the characteristics of PSS and platform business, we select four cases of 'iPod of Apple', 'Kindle of Amazon', 'Zune of Microsoft', and 'e-book reader of Sony'. Then, the four cases are categorized as successful and failed cases according to criteria of case selection and PSS classification. We consider two methodologies for the case selection, i.e., 'Strategies for the Selection of Samples and Cases' proposed by Bent(2006) and the seven case selection procedures proposed by Jason and John(2008). For case selection, 'Stratified sample and Paradigmatic cases' is adopted as one of several options for sampling. Then, we use the seven case selection procedures such as 'typical', 'diverse', 'extreme', 'deviant', 'influential', 'most-similar', and 'mostdifferent' and among them only three procedures of 'diverse', 'most?similar', and 'most-different' are applied for the case selection. For PSS classification, the eight PSS types, suggested by Tukker(2004), of 'product related', 'advice and consulancy', 'product lease', 'product renting/sharing', 'product pooling', 'activity management', 'pay per service unit', 'functional result' are utilized. We categorize the four selected cases as a product oriented group because the cases not only sell a product, but also offer service needed during the use phase of the product. Then, we analyze the four cases by using cross-case pattern that Eisenhardt(1991) suggested. Eisenhardt(1991) argued that three processes are required for avoiding reaching premature or even false conclusion. The fist step includes selecting categories of dimensions and finding within-group similarities coupled with intergroup difference. In the second process, pairs of cases are selected and listed. The second step forces researchers to find the subtle similarities and differences between cases. The third process is to divide the data by data source. The result of cross-case pattern indicates that the similarities of iPod and Kindle as successful cases are convenient user interface, successful plarform strategy, and rich contents. The differences between the successful cases are that, wheares iPod has been recognized as the culture code, Kindle has implemented a low price as its main strategy. Meanwhile, the similarities of Zune and PRS series as failed cases are lack of sufficient applications and contents. The differences between the failed cases are that, wheares Zune adopted an undifferentiated strategy, PRS series conducted high-price strategy. From the analysis of the cases, we generate three hypotheses. The first hypothesis assumes that a successful PSS system requires convenient user interface. The second hypothesis assumes that a successful PSS system requires a reciprocal(win/win) business model. The third hypothesis assumes that a successful PSS system requires sufficient quantities of applications and contents. To verify the hypotheses, we uses the cross-matching (or pattern matching) methodology. The methodology matches three key words (user interface, reciprocal business model, contents) of the hypotheses to the previous papers related to PSS, digital contents, and Information System (IS). Finally, this paper suggests the three implications from analyzed results. A successful PSS system needs to provide differentiated value for customers such as convenient user interface, e.g., the simple design of iTunes (iPod) and the provision of connection to Kindle Store without any charge. A successful PSS system also requires a mutually benefitable business model as Apple and Amazon implement a policy that provides a reasonable proft sharing for third party. A successful PSS system requires sufficient quantities of applications and contents.