This exploratory study examines the personality characteristics that influence the success of digital start-ups from the perspective of German venture investors. The original research takes a three-dimensional approach and integrates the micro-perspective on the entrepreneurial personality, the meso-perspective on the business model,and the macro-perspective on the entrepreneurial context. Based on qualitative content analysis of expert interviews with German VC investors, this study considers personality and behavioral characteristics of entrepreneurs, such as entrepreneurial motivation and energy and willingness to learn, as the most relevant characteristics for success. Particularly in the start-up phase of a digital company, the ability to question one’s approach and convictions regularly, not only when mistakes are recognized but also to consider information and assessments from others, characterizes successful entrepreneurship. In addition, German VC investors consider the overall group of personality characteristics (perspective on entrepreneurial personality) to be most important for entrepreneurial success. Furthermore, the experts’ assessment of success characteristics provides a valuable perspective that has received little attention in the current literature. Finally, this study provides practical added value for researchers and practitioners regarding considering focal points in German VC investors’ implicit or explicit valuation model.