Global advances in digital technology are facilitating corresponding rises in digital entrepreneurship and its startup manifestation. There are many uncertainties on the road to digital startup evolution, some of which may be successfully navigated with the assistance of business incubators. While these organisations provide valuable guidance and support to the startup community, their efforts are at least partly constrained by the lack of a consistent, coherent roadmap to guide both them and their incubatees. T0 help efforts to develop such a map, this paper seeks to identify factors that influence digital startup evolution within an incubator setting through a multiple-case study focusing on digital startups under the umbrella of three business incubators in the Swedish city Umeå. Sets of enabling and inhibitory factors are identified through literature searches and the case studies. The latter may include inertia and possibly attitudes towards failure. In addition, present the Ideation Dynamics Model as a guide for both incubators and digital startups is proposed.