The growing ageing population phenomenon is both a challenge and an opportunity at both social and economic levels. Related to this major demographic shift, longevity/ silver economy and senior entrepreneurship are emerging fields providing a rich topic for scientific studies, largely unexploited and requiring new approaches. The purpose of our paper is to contribute to a more in-depth understanding of those two low documented fields, by emphasizing their increasing dynamic, main features and synergies through an extensive and thorough analysis. The new generated knowledge, using an exploratory qualitative research, based on a semi-structured interview guide, revealed relevant aspects regarding Romanian elderly as entrepreneurs: their profile, driving motivations, some of the main obstacles they have to overcome and measures that may support their endeavour. As the first to address such subjects, our paper can contribute to the complex process of raising awareness about Romanian silver economy and seniors’ untapped potential.