This paper investigates how sources of social exclusion and support emerge within an “older” entrepreneur's immediate environment, and how this affects the development of their small business. Based on 22 in-depth interviews in London, United Kingdom, we suggest how older entrepreneurs with different backgrounds are able to manage social exclusion, and identify four coping strategies—passive negotiation, active negotiation, modification, and avoidance. We argue that, if “older entrepreneurship” (people starting a business aged 50 or older) is to flourish, both entrepreneurs and support initiatives need to become sensitive to the diversity of sources of discrimination and strategies to manage them.