Loneliness, involving a complex set of feelings that occurs when social needs are not adequately met, has been described as a worldwide modern epidemic. Despite its infiltration into all occupations, loneliness may be especially problematic for those in extreme occupations, such as entrepreneurs, who deal with acute levels of uncertainty, resource constraints, responsibility, and time pressure. Disparate prior findings suggest that entrepreneurs may be especially prone to loneliness, less prone to loneliness, or that they may have unique coping mechanisms that allow them to effectively manage loneliness. This conflicting evidence suggests that we have an incomplete understanding of loneliness within entrepreneurship, specifically, and extreme occupational contexts more generally. Integrating literature on loneliness, well‐being, and entrepreneurship, we conduct a qualitative, inductive study analyzing over 9000 Reddit posts drawn from online entrepreneurship communities where individuals seek and offer advice on how to address entrepreneurial loneliness. In applying appraisal theory to interpret our findings, we discover that whereas some entrepreneurs experience loneliness as threatening and harmful, others experience loneliness as positive or irrelevant, contrary to existing literature that points to loneliness as wholly negative. As such, we uncover several different processes through which entrepreneurs appraise and cope with their loneliness, as well as occupationally unique outcomes for entrepreneurs if loneliness is not coped with effectively. Our findings and emergent theoretical model of the loneliness process in this extreme occupation have important implications for research and practice regarding loneliness, well‐being, and the psychological and mental health of entrepreneurs.

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