Founder age is a significant signal influencing investors’ funding decisions for early-stage new ventures. Older first-time founders are starting more new ventures than ever before due to the aging of the workforce coupled with employment instability for long tenured employees. However, research findings regarding how founder age drives funding decisions are mixed. Ambiguity exists as some scholars emphasize the importance of youthfulness in driving entrepreneurship and innovation, while others advocate for the value of seniority in leading the new venture to success. A multiple case study of six angel investors was conducted using a uniquely constructed dataset of thirty-eight new ventures seeking funding. This study argues that prior research has been hindered by the lack of a comprehensive theory that accommodates the various signals delivered at the founder-level and the founder-investor level. Hence, the study extends signaling theory and entrepreneurial literature with empirical findings which demonstrate the interdependence between founder age, informational, and interpersonal signaling in determining an investor’s funding decision. Utilizing fuzzy set qualitative comparative analysis (fsQCA), this paper identifies combinations of signaling conditions linked to an investor’s funding offer. These findings are elaborated upon to develop a typology of successful signal configurations, advancing the understanding of the complex role of founder age in investor new venture funding offer decision-making. The study also introduces a new signaling configuration framework which integrates signaling theory and configurational concepts to capture the causal complexity of signaling phenomena, emphasizing the features of conjunction, equifinality, and asymmetry. The new theoretical framework captures the causal complexity inherent in signaling relationships and enhances our understanding of how and why combinations of different factors lead to a particular funding offer outcome. In practice, the study provides new venture founders insights which may be used to best position their fundraising activities as well as enables investors to identify areas susceptible to age bias which may obscure otherwise profitable funding opportunities.