This chapter describes Swedish entrepreneurs aged 80 plus, providing some quantitative data and reporting two case studies. Self-employment can be considered a means to overcome ageism in the labour market, and is often considered the only way to stay in the market after retirement age. Entrepreneurship research often stresses the connections between entrepreneurship, youth and masculinity. Information is given on all individuals older than 80 on the Swedish market. Two case studies of enterprises owned and managed by 80 plus entrepreneurs are presented: Lena, who developed a business based on her language competencies, and Carl with his wife Carin, who run an enterprise producing exclusive vegetables and fruit for the market. Crucial dimensions of their enterprises are time and experience. They use their competencies and expertise developed during their careers in their working lives. They are very innovative and creative in many aspects—what they produce, how they organise and where they find their market. Both the presented enterprises are producing unique services, so the owners feel they must continue as long as they can. Ageism is well-ingrained in our society, but oldest old entrepreneurs may challenge it.