The gradual decline of cash and proliferation of digital payments have created a radical shift, promising new levels of convenience for consumers today. This may adversely impact the earning potential of artists and performers from the busking community. Since the busking community primarily relies on hard cash/spare change from their patrons, I will argue, the predictions of a cashless society can pose great challenges for the busking community. This thesis investigates how mobile technology might address this phenomenon to augment methods of making monetary and non-monetary contributions to buskers. Research through ethnographic methods and literature review, as well as usability testing, the gathered insights and results projected a foreseeable need for buskers and patrons to realize an exchange via a mobile application called ‘Hatter.’ Hatter enables patrons to continue to contribute to buskers, who in turn are empowered to receive social and financial capital, even in a cashless society.