In this paper, I analyze the costs and benefits of waste prevention and zero waste initiatives that are inflicted upon society. The problem lies in the amount of human municipal solid waste (HMSW) resulting from human activities, especially as growing global urban population estimated to be producing three times as much waste as it does today (Goto, 2014). Landfill externalities are addressed to explain the purpose of this research. Additionally, the efficiency of diverting waste from the landfill is assessed; these diversion methods are recycling, composting, and the uses of TerraCycle. It is important to note the difference between waste prevention and zero waste: Waste prevention is simply reducing the amount of waste, whereas zero waste is aiming to divert HMSW for other uses other than going its final destination, the landfill. This research highlights tax policies and incentive-based approaches that cities currently enforce, as well as repercussions of these approaches. Waste prevention is explored from the user perspective and reactions to taxes on waste that were implemented to promote global sustainability, which can be seen from the primary data collected. I analyze the success of zero waste initiatives in the online marketing agency, Vertical Measures, comparing landfill waste diversion with the implementation of zero waste initiatives. This paper highlights the observations and results from this two-month analysis. With both the analyses of city regulations and first-hand application of zero waste and waste prevention methods, the findings suggest that the success of these initiatives depends on various factors including location and participant attitudes. This research and data can help provide insight for other small businesses for a more sustainable environment and workplace.