Digital entrepreneurship through the employment of smartphones and other handheld device applications is an innovative form of customer approach. Particularly, in the cultural marketing sector, new technologies, such as social media, YouTube channels, and mobile applications may increase the artists’ visibility and attract new partnerships and audiences. In this framework, entrepreneurs-musicians who attended a seminar on Management of Cultural Heritage, Communication and Media in Greece were asked to promote their activities through the creation of a smartphone application. After having completed their endeavor and further evaluated it, they participated in qualitative research based on the theory of experts’ interviews, as a case study. The aim of this paper, through thematic analysis of the conducted interviews, is to reflect upon the dynamics of new technologies in music entrepreneurship. As derived by the analysis, the use of mobile applications may effectively approach prospective partnerships and audiences, especially if combined with other contemporary forms of communication, and results in presenting enhanced professionalism. Audience engagement, which is an issue that is sought while attempting to optimize promotion processes, may be achieved if a further practice is performed. As the research was conducted during the COVID-19 pandemic, the demand for this form of making publicly known their artwork was considered essential.