Digital native news media have great potential for improving journalism. Theoretically, they can be the sites where new products, novel revenue streams and alternative ways of organizing digital journalism are discovered, tested, and advanced. In practice, however, the situation appears to be more complicated. Besides the normal pressures facing new businesses, entrepreneurs in digital news are faced with specific challenges. Against the background of general and journalism specific entrepreneurship literature, and in light of a practice–theoretical approach, this qualitative case study research on 15 German digital native news media outlets empirically investigates what barriers curb their innovative capacity in the early start-up phase. In the new media organizations under study here, there are—among other problems—a high degree of homogeneity within founding teams, tensions between journalistic and economic practices, insufficient user orientation, as well as a tendency for organizations to be underfinanced. The patterns of failure investigated in this study can raise awareness, help news start-ups avoid common mistakes before actually entering the market, and help industry experts and investors to realistically estimate the potential of new ventures within the digital news industry.