Digital textile microfactories may drive significant changes in the textile and clothing industries, providing a fully integrated, digitally networked end-to-end design and manufacturing process. Microfactory technology supports increased speed, efficiency, quality, customer interaction, and sustainability. Unlike well-understood and widely adopted traditional technologies, radically new digital technologies come with higher uncertainty regarding their potential short- and long-term risks and benefits for firms adopting them. These uncertainties stem from a lack of historical data and knowledge about potential mechanisms driving success dynamics. This paper aims to help firms develop new business models that use radically innovative digital technologies. For the exemplary case of digital textile microfactories supporting new business models for individualized garments, we explore the system structure and mechanisms that may drive success in digital technology-based business models. In this particular case, we illustrate how qualitative modeling based on the well-known archetype “success to the successful” allows to identify long-lasting competitive advantage mechanisms. This approach can contribute to understanding the dynamics of success of firms adopting this technology and business model. On a more general level, our findings emphasize the benefits of qualitative modeling and stress the significance of adopting a holistic perspective for providing tools that support firms in strategic decision-making and business model innovation.