This study investigates the role of entrepreneurial imaginativeness and grit in the relationship between entrepreneurial passion and entrepreneurial intention using a sample of 360 aspiring entrepreneurs. Building on the new venture ideation and self-regulation theoretical perspectives and situating the study within the South African context, we posit that entrepreneurial passion influences entrepreneurial intention through entrepreneurial imaginativeness. We further posit that the relationship between entrepreneurial passion and entrepreneurial intention is contingent on varying levels of grit. We found that the indirect effect of entrepreneurial passion on entrepreneurial intention through entrepreneurial imaginativeness–creative and practical imaginativeness was significant and positive. Additionally, the findings showed that grit moderates the EP-EI relationship, suggesting that gritty aspiring entrepreneurs are more likely to translate their passion for inventing into strong entrepreneurial intention. These findings offer both theoretical and practical implications.