Abstract: In today's rapidly changing market environment, entrepreneurial firms must continuously iterate on their opportunities to respond effectively. However, not all entrepreneurial firms can agilely make these iterations, making it essential to explore how to achieve successful entrepreneurial opportunity iteration. Successful entrepreneurs, as role models, are believed to offer beneficial reference effects for observers, helping them refine and upgrade their entrepreneurial opportunities. Yet, the potential comparative effects of these role models have often been overlooked. Moreover, upward comparisons with successful entrepreneurs can serve as a unique type of pressure source, potentially triggering both challenge and hindrance evaluations among entrepreneurs. These evaluations can influence decisions and actions related to entrepreneurial opportunities in distinct ways. Thus, it is crucial to investigate the mechanisms through which upward comparison affects opportunity iteration, grounded in cognitive appraisal theory of stress. Our study employs a social comparison perspective, based on cognitive appraisal theory of stress, considering two response modes—problem-focused and emotion-focused—entrepreneurs may adopt when faced with upward entrepreneurial comparisons. The model incorporates imitation learning and entrepreneurial anxiety to examine the differential impacts of upward entrepreneurial comparison on entrepreneurial opportunity iteration under contexts of general challenge and hindrance pressure appraisal. To gather data, researchers conducted a survey utilizing both online and offline methods, collecting valid responses from 248 new ventures at three different time points. The analysis revealed two key findings: (1) When entrepreneurs hold a high general challenge appraisal of upward entrepreneurial comparisons, these comparisons enhance imitation learning, thereby accelerating entrepreneurial opportunity iteration; (2) Conversely, when entrepreneurs maintain a high general hindrance appraisal of upward entrepreneurial comparisons, these comparisons increase entrepreneurial anxiety, which inhibits opportunity entrepreneurial iteration. This study contributes to the theoretical landscape in several ways. First, it integrates a social comparison perspective into entrepreneurship research, investigating the effects of upward entrepreneurial comparisons on entrepreneurial opportunity iteration. This not only expands the application of social comparison theory but also enriches the understanding of the antecedents of entrepreneurial opportunity iteration. Second, it constructs mediating pathways of imitation learning and entrepreneurial anxiety based on cognitive appraisal theory of stress, illustrating how upward entrepreneurial comparisons influence entrepreneurial opportunity iteration from both problem-focused and emotional-focused perspectives. This provides a concrete micro-level explanation for the process of entrepreneurial opportunity iteration while broadening the contexts in which cognitive appraisal theory of stress can be applied. Lastly, the research elucidates the different processes through which upward entrepreneurial comparisons can either facilitate or inhibit entrepreneurial opportunity iteration, depending on whether entrepreneurs adopt challenge or hindrance evaluations of upward entrepreneurial comparisons. This insight helps reconcile existing discrepancies in the literature regarding the influence of successful entrepreneurs on observers. The practical implications of this study offer a conceptual framework for new ventures to iterate their entrepreneurial opportunities through a social comparison lens. According to the findings, entrepreneurs who perceive upward entrepreneurial comparisons as a challenge appraisal should actively engage with successful entrepreneurs to learn from their experiences and enhance their own opportunity iterations. Conversely, those with a hindrance appraisal should limit comparisons with successful entrepreneurs. Additionally, entrepreneurs are encouraged to participate in imitation learning while consciously monitoring and regulating their anxiety levels. Furthermore, entrepreneurial incubation institutions and regional management committees should provide resources and training to bolster entrepreneurs' confidence and efficacy, thereby fostering a challenge-oriented mindset in response to upward comparisons.