With the emergence of Web 2.0, the role of digital content users has expanded from digital content consumers to digital content creators, both of which are contributing significant changes in the economy, society, and culture. In light of this phenomenal trend, we categorize digital content users into digital content user 1.0 (passive users) and digital content user 2.0 (proactive users) in order to develop specific business models and digital service strategies. These two types of digital content users are established based on the patterns of the digital content usage. Along with these types, the effects of digital content characteristics (design, scenario, structure, and technology) on the usefulness, flow and usage intention of digital content are analyzed. Results show that design characteristics do not affect usefulness for both user types. While the technological characteristics of digital content have a positive effect on the flow of digital content user 1.0, the design, scenario, and structure characteristics have a positive effect on the flow of digital content user 2.0. Our study helps managers establish digital content business strategies and digital service plans based on the characteristics of digital content and digital content user types. Our study also provides a theoretical foundation for future digital content related studies.