This report provides a description and analysis of two sets of design workshops intended to provide insights into the challenges and opportunities facing new entrants into the field of digital financial services, both as providers and users. These workshops follow on from our investigations into the social and technological infrastructures of the Bristol Pound (£B) and Zopa Limited. Our findings, described in other reports, have been fed back into the development of probes used in the design workshops and have allowed us to continue to explore the financial service design space in ways that exclusively studying existing practice could not.