This chapter examines how Generative AI (GenAI) is being adopted or cautiously approached by librarians and entrepreneurs. It introduces a GenAI adoption model contextualized for library and entrepreneurial environments. Through a real case study of a library, the chapter demonstrates how co-experimentation between libraries and entrepreneurs strengthens adoption drivers like technological familiarity, social influence, and domain relevance for fostering the adoption of GenAI. It reveals that the collaborative experimentation process creates a reinforcing loop, where improvements in one adoption factor begin to boost others, leading to more sophisticated experimentation and a sharper ability to identify both the use and misuse cases of the technology.