This paper investigated trends in social entrepreneurship within non-profit organisations (NPOs). It was inspired by a survey conducted by Trialogue, a non-profit research organisation that surveys corporate social investment in South Africa. The survey showed a significant number of Non-profit organisations (69%) are moving toward developing social enterprise due to issues of sustainability. The research sought to ascertain what are the causes for the trend. The method of sampling used was non-probability, purposeful sampling to select 12 organisations from the available population. An exploratory qualitative study was conducted via face-to-face interviews with 12 organisations and 14 respondents. The transcripts of each were manually reviewed line-by-line for common themes to compare and generate results. The study was undertaken to better understand what motivated NPOs to social entrepreneurship and how they identified and exploited opportunities; distributed revenues and what form of relationship was created with the parent organization. The study reviewed theoretical models and selected a best-fit model of the Opportunity Creation Process which had to be modified to suit the trends in thought that arose from the study. The findings showed that funding challenges of the parent NPO and limited access to funds were key features likely to illustrate when an NPO will move into social entrepreneurship. The research concludes with evidence demonstrating that NPOs are not always willing participants in the social enterprise game, but are forced to discover opportunities to prove to funders that they are seeking means to be sustainable, with varying degrees of success. The form of social enterprise they select is often determined by the centrality of the NPOs mission to that of the social enterprise.