Innovative technologies promise countless disruptive use cases in the travel and tourism industry. Despite their potential to improve the sector, technology adoption faces substantial barriers, such as high implementation costs, the need for significant infrastructure upgrades, and a lack of technical expertise among stakeholders. Existing theoretical approaches (e.g., Diffusion of Innovation, Technology-Organization-Environment framework) regularly assume a gradual adoption process and identify potentially relevant adoption drivers. However, such broad theories can only partially explain the high failure rates of startups in the industry and offer little advice for new endeavors. In this study, we use the case of Winding Tree, a startup that strived to create a decentralized, open-source marketplace for the travel industry, to illustrate the need for a stronger focus on the adoption gap and the key factors that enable or prevent enterprises from reaching a critical market size. We suggest a modification of Chasm Theory for tourism and travel research and present a framework that can help to better explore, explain, and predict the impact of digital transformation.