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Generative artificial intelligence (AI) tools are transforming visual production across multiple domains, including entrepreneurship. However, their influence on constructing cultural imaginaries and legitimating symbols remains insufficiently examined. This study analyzes how text-to-image systems visually represent entrepreneurship and success, using a focused sample of 24 images generated with the Midjourney platform. Through critical visual discourse analysis, the research identifies recurring aesthetic codes, symbolic patterns, and temporal framings that demonstrate how generative AI replicates established cultural narratives of entrepreneurship. The results indicate a consistent depiction of solitary, self-assured individuals who embody control, ambition, and transcendence. In contrast, representations of collaboration, diversity, and social contribution are largely absent. The visual grammar emphasizes formality, isolation, and monumental composition, while temporal orientations favor immediacy and permanence rather than process and collective effort. These algorithmic representations reinforce narrow ideals of entrepreneurial legitimacy and perpetuate masculine-coded notions of success and authority. To synthesize these findings, the study introduces a conceptual model of the sociotemporal automation of legitimacy in generative AI entrepreneurial imaginaries. This model connects algorithmic infrastructures, aesthetic and temporal representations, and cultural circulation through the feedback loop of human-AI co-production. The paper contributes to understanding the aesthetic mechanisms by which generative AI consolidates dominant entrepreneurial ideals and considers implications for critical visual literacy, responsible AI deployment, and inclusive innovation policy. • Generative AI systems reproduce dominant visual stereotypes of entrepreneurship. • Midjourney portrays entrepreneurs as solitary, self-assured, and transcendent figures. • Visual narratives emphasize control, ambition, and permanence over process or collaboration. • Diversity, collectivity, and social contribution are largely absent from AI-generated depictions. • The study theorizes the “sociotemporal automation of legitimacy” in generative AI imaginaries.