Abstract Scholarly studies of business enterprises in colonial Lagos have neglected Chief Joseph Adediran Ajao, a foremost investor in the real estate enterprise. Though there are sketchy details about him in social circles and passing but constant references to him typified by «Ajao Estate» and «Papa Ajao» communities, there is yet to be any thorough scholarly study of his enterprise. Using family records, archival documents, court records, newspaper reports, interviews, published works, and site visit, this study examines the entrepreneurship of Chief Joseph Adediran Ajao. It sheds light on Chief Ajao’s entrepreneurial exploit first in the import and export trade from which he earned substantial wealth, and ultimately on his investment in land and real estate, where he left an extant impression as one of the largest land-owning individuals in Lagos. On the premise that African culture had a significant impact on African businesses, this study is situated within the context of Yoruba philosophy of business and enterprise. The study concludes that: one, Chief J. A. Ajao was a forerunner of the emergence of real estate enterprise in Lagos; two, Chief J. A. Ajao’s import-export business, J. A. Ajao and Brothers, though eclipsed by his real estate enterprise, was no less significant; and three, J. A. Ajao’s enterprise ensured that his name achieved an eponym status in Lagos.