Community based co-operatives do not have a good record. The fact that so many co-operatives fail, constitutes a real danger that the co-operative model could fall into such disrepute that it will become widely rejected. Consequently a potentially valuable mechanism for economic development and reconstruction will be lost. One of the reasons for cooperative failure stems from the past perception of co-operatives as anti-capitalist forms of association. Co-operatives were a way of releasing the poor from the yoke of oppression and giving them access to power and employment. This "socialist" view of co-operatives excluded the one important ingredient of a successful business venture: entrepreneurship. The paper investigates the "co-operative entrepreneurship" dilemma, and indicates that entrepreneurship and co-operativism are reconcilable concepts. The circumstances for a successful entrepreneur: co-operative relationship are discussed, and other critical factors associated with success in community based co-operatives are discussed.