Entrepreneurial journalism is often ascribed the potential to partly close the supply gap in digital journalism caused by the effects of digitization. Decreasing fixed costs on the production stage, in particular, have enabled smaller entities, entrepreneurs and start-ups to produce high quality journalistic content. While there is a broad stream of literature on entrepreneurial success in general, empirical research says little about the reasons for digital journalistic entrepreneurs’ success (or lack thereof). This study aims at empirically investigating success conditions associated with entrepreneurship in the digital news business. Seven broader “super”-conditional prerequisites are considered: Experience, skills, personality, product, business model, company organization, and broader environment. The data, collected through 49 interviews with digital journalistic entrepreneurs in Germany, is analysed with Qualitative Comparative Analysis (QCA), a set theoretical method to determine necessity/sufficiency of preformulated conditions for a respective outcome (i.e., entrepreneurial (non-)success). The results indicate high importance of, first, the experience of the founder, and, second, the functioning organization of the company, while, interestingly, third, only absence of support from the broader environment and/or government contributed to the success.