This paper conceptualizes ‘creative transactions’ – payment for creative work – as a rich site for the study, design and innovation of new financial technologies, and ‘special digital monies’. For most, creative labor remains highly precarious and underfunded and those working in the creative industries frequently rely on diverse forms of funding for their work. As a case study, we draw on a corpus of 87 ‘Break Kickstarter’ crowdfunding campaigns, where project creators were encouraged to break conventions and “rethink what a Kickstarter campaign can be”. By studying how these innovative projects broke fundraising conventions and experimented with the transactional attributes of a Kickstarter campaign, we show how they reconfigured the payment for creative work, and developed new relations between creators and their audiences. Drawing on these analyses, we derive new ideas and opportunities for the design of special digital monies to support novel creative transactions beyond crowdfunding campaigns.