This article discusses the strategies that sustainable entrepreneurs use to interact with their environment in the Dutch construction industry. The Dutch construction industry is under great pressure to move towards sustainability, and entrepreneurs are believed to be able to play a large role in this transition by introducing new products and new business practices. But how can entrepreneurs prosper in an environment that is not geared up towards such a change? And which strategies do they use to bend conditions in their favor? In this article we make use of the Market and System Failure Framework to analyze the pressures that entrepreneurs are confronted with when introducing sustainable innovations. We recognize that these pressures can be seen as bottlenecks, but that market and system failures can also create entrepreneurial opportunities. We interviewed 16 entrepreneurs in the Dutch construction industry to determine the influences they experienced from their environment and the strategies they use to deal with these. We conclude that we can distinguish between system building and following entrepreneurs, where the former aims to build a new system to challenge the old one, whereas the latter rather makes use of existing structures to build a business. We find that both strategies can be successful and that overall, the entrepreneurs confirm the belief that sustainability on people, planet and transparency aspects, can contribute very well to the long term profitability of the businesses the entrepreneurs are running. These in-depth insights into the influences from the context on the one hand, and the entrepreneurs’ strategic reactions on the other hand, contribute to our understanding of the interactions between entrepreneurs and the system context. This can help us to more effectively stimulate and support innovating entrepreneurs to contribute to the transition towards sustainability.