Considering rapid digital transformation and recent changes in the macro-level “rules of the game” in entrepreneurship, we aim to problematize and understand the progressive encounter and new relationship between opportunity-driven and necessity-driven entrepreneurs within the context of the gig economy. In such a setting, both traditional entrepreneurial roles and the very division between them are brought into question. Their encounter implies a deviation from the basic assumptions of what entrepreneurship entails: being the bearer of risk, taking on uncertainty and individual responsibility, and pursuing unlimited profit potential. This deviation results in a change in the rules of the game. Consequently, we learn more about how the context of moving from a pre-gig economy toward the gig economy has implications for our societal understanding of entrepreneurship as a phenomenon.