Why are some entrepreneurs “luckier” than others? This is a fundamental question in entrepreneurship. Often, what appears as fortuitous outcomes are the result of a confluence of the entrepreneurial attitude and environmental factors. Drawing from the self-determination theory (SDT), this study argues that happier entrepreneurs tend to better fulfill their need for competence, becoming more confident, thereby experiencing greater levels of serendipity. Additionally, such relationship is strengthened when entrepreneurs fulfill their psychological needs for relatedness, fostered by third places, and autonomous thinking, fostered by an adequate walking infrastructure. Entrepreneurship is thus not just about possessing the right attitude, but also about being in the right place for serendipity to flourish.