The chapter aimed to contribute to the understanding of the roles of the cannabis industry's stakeholders/transforming structures/institutions to empower and sustain local rural SMMEs in SA. The lesson learned from the literature reviewed in this chapter is that local stakeholders/institutions/transforming structures can either play a positive role or be a negative force in the empowerment and sustainability (using available resources/assets) of the cannabis-related SMMEs. It is therefore concluded that for South African cannabis stakeholders to effectively empower and sustain (using their resources) local rural SMMEs, they ought to embrace cannabis-related SMMEs' local values and assumptions alongside their regulations and laws. The contribution of this chapter is in the process of how key local rural-based institutions/stakeholders/structures can effectively use their resources/assets, rules, regulations, local values, and assumptions to transform each other positively in pursuit of cannabis-related SMME's empowerment and sustainability in SA.