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Along many dimensions, Meiji Japan represented a transition economy. It was transformed from a closed to an open, from a feudal to a capitalist and from an agricultural to an industrial economy. Entrepreneurship played a crucial role in the transformation. This paper analyzes the role of entrepreneurship in the establishment of Japan’s life insurance industry. Life insurance has received little attention in research on Japanese industrialization and entrepreneurship. Japan’s domestic life insurance industry had been successfully established by the end of the Meiji period, which constitutes an impressive achievement. This paper analyzes the profiles of 15 entrepreneurs who played key roles in the establishment of 11 life insurance companies between 1881 and 1912. Many of them share characteristics typical of early Japanese entrepreneurs in other industries in terms of family background and patriotic motivation. Their wide scope of activities and networks beyond the insurance industry helped them to cope with the institutional uncertainty characteristic of transition economies. Their high social standing and cross-sectional networks provided them with the credibility needed to found an insurance company, whose business success was heavily dependent on gaining the trust of potential policyholders.