With information technology (IT) now showing advanced capabilities, many new services are being introduced to consumers of smartphones through the various available app stores. Moreover, the recent proliferation of such services related to information and communications technology has seen a momentous rise. Despite this trend, the ever-changing landscape of mobile IT services is creating a serious problem for businesses who are already experiencing fierce market conditions. Thus, in order to maintain the sustainability of an enterprise, it is necessary to make an adequate analysis of the success and failure factors of IT services in order to create a sustained competitive advantage. Considering 22 real IT service cases based on two platform models (merchant model and two-sided model) and through surveys submitted to 11 experienced entrepreneurs in IT services, we conducted a t-test analysis in order to first assess the success and failure factors of the IT service cases. Next, we performed a logistic regression analysis in order to find underlying relationships of our hypothesized model. The results showed that the participants identified 141 success and 101 failure factors in total with the t-tests, confirming that the distinction between success and failure of each IT service assessed was significant. Next, the results from the logistic regression showed which relationships were the best on the basis of the given platform model. Overall, this study was able to identify the main factors that have an influence on the success and failure of IT services based on two identified platform models. In doing so, this paper can help to inform future IT service entrepreneurs and researchers involved in developing new apps based on IT services by providing a guide to what factors need to be considered before going to market.