This article explores the roles that the managing directors (MDs) of investee companies play in influencing the post-investment involvement of their business angels (BAs). Primary data were collected from four matched BA–MD dyads, which were purposefully selected according to the BAs’ level of post-investment involvement. The dyadic parties were interviewed independently from one another on four occasions over the period of one year. Interview questions were loosely structured around involvement and interaction. Coding and extensive iterative cross-case comparisons resulted in the emergence of four key themes relating to MDs' roles in involvement: MDs' responsiveness to involvement; MDs' communication of/feedback on their responses to involvement; MDs' reactions to queries from their BAs; and MDs' roles in initiating involvement activities. The article explores each of these roles by providing insights into the qualitative data in comparison with extant literature surrounding those themes. The article concludes with a number of propositions which suggest that (i) MDs play a ‘gatekeeper’ role which requires them to be responsive if the involvement of the investor in the business is to occur, and for the investor to add value; (ii) BA–MD interactions are affected by the quality of MDs' feedback in case of non-responsiveness, the way in which MDs react to queries from their investors and the MDs' attitudes towards learning from BAs; (iii) BAs expect their involvement to be acknowledged and (iv) MDs can initiate involvement themselves. The study further shows that involvement is not a purely investor-centred concept, which is an insight that needs to be investigated further, on a larger scale and with the help of a conceptual framework.