Technology startups are globally recognized as contributors to innovation and entrepreneurship. However, this emerging industry faced a lot of challenges and uncertainties in the search for a scalable business model. Considering the importance of people as innovative drivers in the development of startups, this study uncovers what constitute to the experiences of software developers using a Grounded Theory Methodology. Findings revealed that acquiring skills in doing multiple roles is their main concern and the core category that resolves their concern is the cyclical basic social process of Roling. Roling involves two stages: Instalearning and Perfortraying. Instalearning is employed through the following techniques: self- learning, collaborating, and networking. Perfortraying includes the following practices: Dutying, Spanning, Substituting, Sharing, Swapping, Grabbing, and Hopping. This study is hoped to contribute to the development of processes, structures and policies that highlights the role of developers in technology startups among other stakeholders.