The purpose of this study is to explore business investment and operation of O2O (Online-To-Offline) combined service. The study will analyze the necessary factors for growing the business by dividing the O2O service by industry. The Online-to-Offline is a method of inducing purchases of products and services by connecting between online and offline This research methodology organized the four stages of the analysis process. The analysis of all stages was performed with association rules in big data techniques. It is divided into the start-up period, growth period, maturity period, and decline period, and analysis is conducted on the business investment, expenditure cost, business operation, and conflict factors. As the research result, the first analysis has shown commonality with government subsidies, bank loans, and personal funds in all industries. The second analysis showed a lot of expenditure on labor costs of internal employees, marketing/sales, facility facilities, equipment, and equipment purchase costs. The third analysis showed difficulty in raising the investment resources necessary for business operations in all industries. The last analysis showed conflicts in the industry, businesses license, legal systems, and small business owners in all industries. This study contributed to the abundance and diversity of research methodologies in management information systems using association rules. In addition, the description of organizational development theory was updated while explaining the business investment and operation of O2O combined services. In practical implication, the O2O services include environmental factors that cause convergence between industries. Accordingly, this is required for new O2O services through new laws and systems and reorganization of existing laws and regulations.