This chapter contributes to a broader understanding of how city branding affects all place customers – such as residents, companies and tourists – and discusses the specific role of cultural heritage in this regards. While branding often relies on simplified messages (e.g., focusing solely on the cultural heritage), the effectiveness of such strategies for complex brands, like city brands, remains questionable. Residents and business customers often have an acute knowledge of the place and could disagree with a simplified, touristic destination brand.