This project investigates the motivations of technology entrepreneurs and social entrepreneurs for starting new ventures. The driving personal motivations and external, systemic influences on entrepreneurs’ decision making is explored and structured through analytical frameworks. Research consists of a comprehensive literature review that establishes the context and foundational knowledge around the catalysts of entrepreneurialism, both in the high tech and social enterprise sectors; a series of semi-structured one-on-one interviews with technology and social entrepreneurs; and a series of expert interviews with venture capital investors and organizations that support startups. The output of this research is new, primary-research driven insights on entrepreneurial decision making; a stakeholder matrix and systemigram that visually summarizes the problem system; a new framework with which to examine the challenge of shifting technology entrepreneurs towards social benefit efforts; and a series of design recommendations to stakeholders who benefit from implementing that shift.