Startups are conquering relevant space in the market. This way to make entrepreneurship has singular features, such as resource limitations and extreme uncertain environment. In this context, using auxiliary tools for managing the business and technology can be potentially helpful. There are many tools for managing product development in large companies. These tools are not immediately applicable when greater agility is required, as in startups. Thus, the purpose of this article is to analyze the use of roadmapping in the context of digital entrepreneurship and to describe factors that may be considered essential for the success or failure of implementation. The methodology in this paper was multiple cases of studies involving interviews with three entrepreneurs of different startups. After analyzing and comparing the data and contextualizing them in theory, four main factors affecting the use of roadmapping in startups were found: lack of theoretical knowledge, the specific moment of the startup in its life cycle, team involvement with roadmapping process and methods associated with roadmapping. These factors are debated, difficulties are shown and comments about method implementation are described.