Startup success rates are critically low, with fewer than half surviving beyond five years. Given the significant economic and social contributions of entrepreneurship, improving these rates is vital. This study explores the interplay between entrepreneurial satisfaction, wellbeing, and performance in the context of scaling, focusing on how entrepreneurial ecosystem attributes influence these dynamics. Using semi-structured interviews with 30 entrepreneurs from five European ecosystems (Berlin, Helsinki, Stockholm, Tallinn, and Vienna), we conducted a Qualitative Comparative Analysis (QCA) to link ecosystem attributes to founders’ emotional states and satisfaction. Our findings reveal two distinct groups of entrepreneurs: those experiencing frustration and dissatisfaction due to unmet ecosystem expectations, resulting in stress, burnout, and reduced venture performance, and those reporting optimism and satisfaction, which enhanced resilience, decision-making, and organizational culture. This research highlights the critical role of emotional wellbeing in scaling ventures, demonstrating how ecosystem support, mentorship, and mental health resources can mitigate stress and foster positive emotional states. Satisfied founders are better equipped to navigate challenges, sustain momentum, and drive venture success, whereas dissatisfied founders face compounded difficulties that jeopardize their ventures. Our findings emphasize the need for ecosystems to provide not only tangible resources but also emotional and psychological support to entrepreneurs.