This case study covers the concepts of upcycling under the gamut of circular economy, a concept that has become more of a strategy to sustain and survive in today’s world. This case is about Rimagined, an upcycling company that could be a model for circular ideas and upcycling of stuff. This case study narrates the growth and the challenges faced in upcycling and encourages students to ideate a new design for any upcycling item of their choice. This case will also make students strategize the expansion plan for Rimagined. Shailaja Rangarajan is the protagonist of this case study who started this social enterprise to make a difference and do her bit. Sustaining a social enterprise requires business acumen and risk-bearing capacities like any other business. Rangarajan was facing the dilemma of expansion and was trying out several feasible options. Rimagined had been unable to attract investors because their expectations of quick returns could not be immediately fulfilled. Investors focused more on waste management as an industry and not on upcycling as a separate area of work.