Global advances in digital technology are facilitating a corresponding rise in digital entrepreneurship and its startup manifestation. Many uncertainties exist upon the road to digital startup evolution; a number 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 in some part, constrained by the lack of a consistent and coherent roadmap to guide both them and their incubatees. This work proposes a solution to that deficiency by addressing the question -  What are the enabling and inhibiting factors in digital startup evolution within an incubator setting? - via a multiple-case study that examined digital startups under the umbrella of three business incubators in the city of Umeå, Sweden. This work builds on the existing literature both through its narrowed focus on incubators as well as through its presentation of the Ideation Dynamics Model as a proposed guide for both incubators and digital startups to follow.