The fundamental purpose of design is to construct artifacts which interface inner and outer systems. Recent work in entrepreneurship makes a compelling argument that opportunities represent an artifact which interfaces inner systems of the entrepreneurial firm with outer systems of customers, markets and supplier stakeholders. In this formulation, opportunities might emerge from one of two ideal forms of design, namely experimentation or transformation. We build on such work, exploring a different artifact - the entrepreneurial organization. Adopting a design perspective, we compare the trajectories of two ventures with relatively similar starting points, but imprinted by different artifacts which encouraged the use of design approaches of experimentation in one and transformation in the other. We expose critical areas of divergence in the organizations that emerge. Imprinted by a trove of available concrete artifacts, the organization employing experimentation features dense, strongly tied networks, a more loyalty and work oriented culture and a simpler, less flexible, more incremental strategy. By contrast, the organization imprinted by penurious resources employed transformation, and features less dense, weakly tied networks, a more political, status oriented and discursive culture, and a more flexible, growth-oriented strategy. The practical implication of our work lies in the insight that through starting endowment imprint and design approach, future entrepreneurs might build features into the ultimate artifact they create - the organization itself.