A high level of uncertainty accompanies investment decisions, hence, VCs attempt to reduce their risk through a thorough examination of potential investment cases. Especially during the seed and start-up phases of a new venture, when detailed reports and historical track records are still lacking, the investment manager’s trust in the entrepreneurial team has a major impact on investment decisions. To explore the process of trust formation, we conducted 11 semi-structured in-depth expert interviews with VC investment managers. Thereby, the COVID-19 crisis provided unique circumstances of exclusively digital communication and allowed us to develop a fine-grained understanding of trust within the VC context. Building on previous research about organizational trust and 674 interview minutes, we found that trustworthiness develops to trust over time as the vulnerability of both parties increases. Furthermore, our results reveal that the VCs’ perception of the founders’ trustworthiness is mainly influenced by examining the founders’ work environment, a founders’ reputation in the VCs’ network, and face-to-face communication. Such personal meetings allow VCs to assess founders, shape the investor’s gut feeling, and develop an interpersonal relationship as they allow for more room talking about personal information rather than business talk.