The second case study in this book offers a deep dive into the brand activism of two distinct entities: the fashion giant Kate Spade and the social enterprise organisation Change Please. These two brands show how brand activism, especially when authentically aligned with a brand’s mission, can significantly influence targeted societal groups. Kate Spade is highlighted as a brand with activism ingrained in its DNA, focussing on women’s empowerment and mental health. Change Please is showcased as a social enterprise born with a mission to tackle homelessness through the daily habit of coffee drinking. It demonstrates how a brand built on social activism can enable significant societal change while operating a sustainable business model. Furthermore, this chapter indicates the importance of partnerships in amplifying brand activism, showing how Kate Spade and Change Please exemplify the ways in which brands can serve as navigational landmarks for consumers, and thus providing a blueprint for other entities seeking to embed activism into their business models.