The present study focuses on the construct of entrepreneurial alertness, investigating the external antecedents of the construct, responding to the call for more research pledged by Tang, Kacmar, and Busenitz (2012). Namely, we examine how receiving feedback, awards and collaboration offers in relation to an individual’s hobby activity influences the development of entrepreneurial alertness dimensions. Additionally, we make a contribution by testing the effect of these external factors in a non-entrepreneurial context of homebrewing communities, that is individuals producing beer at home as a hobby. In line with other form of craft activities, this context has demonstrated a high potential for business start-up development due to the increasing number of new small brewing businesses in North America run by entrepreneurs that were previously homebrewers (Carroll & Swaminathan, 2000). We test our tenets within the complexity theory, where configurations of antecedents are examined in order to gain deeper understanding of the possible outcome (Woodside, 2014), using 213 completed questionnaires. We apply fuzzy-set qualitative comparative analysis (fsQCA, Ragin 2000; 2008) to achieve a holistic overview of the examined interrelationships (Ordanini, Parasuraman & Rubera, 2015). We find that high feedback is a sufficient condition for high scanning and search, association and connection, as well as evaluation and judgement activities of entrepreneurial alertness. Without feedback, people at the hobby stage engage in their leisure activities solely because they like it. However, receiving feedback in relation to their hobby outcomes provides an opportunity for individuals to develop and experience additional motivations beyond enjoyment, where they understand that the hobby could be commercialized and bring monetary rewards. Moreover, we find that an individual receiving low amount of awards but high amount of collaboration offers may also have high entrepreneurial alertness. Since individuals receive rewards related to the excellent performance in their leisure activity, it may not provide any cue for a potential transformation into a business. However, the more collaboration offers people receive, the more likely they get involved in scanning and search, association and connection, and evaluation and judgement activities of entrepreneurial alertness. Therefore, they are likely to conduct additional search, connect bits of available information and evaluate this business opportunity (Gaglio & Winter, 2009). The findings of this study could help entrepreneurs reflect on their decisions and behaviours during the business start-up planning process, and measure their entrepreneurial alertness and the extent of readiness to engage in business venturing.