AbstractTechnological advancements have created opportunities for entrepreneurship and innovation and enabled the development of new products, services, platforms, and business models, including the freemium business model. The freemium business model is present in several digital services (e.g., music, social networking, and gaming), but, for businesses to succeed, it is of the utmost importance that users convert their subscriptions from free to premium. Previous research has endeavored to explain what motivations drive consumers to adopt different digital services and platforms and what motivations and user characteristics lead them to convert to the premium service, but little research has been dedicated to the motivations for consumers to distinguish between competing platforms. To enhance comprehension of these matters, this study analyzes a group of motivations and user characteristics as explanatory variables. Data was obtained via an online questionnaire, with a sample of 231 users of music streaming platforms. The main results suggest that satisfaction, perceived value, and ubiquity are statistically significant motivations that positively influence choosing a platform. Regarding subscribing to the premium service, the same motivations, as well as users’ age and occupation, present influential results, which are relevant from theoretical and managerial points of view, especially for entrepreneurs aiming to define the best strategy to successfully deploy their digital businesses.