One of the major issues associated with taxation are the costs incurred by taxpayers when they comply with their tax obligations, this is particularly important for smaller business taxpayers. Compliance costs are found to be regressive, falling with disproportionate severity on smaller businesses. This trend can be found across the globe and more importantly, in New Zealand. Prior research has shown that the severity of the regressiveness has increased over time. The current, “one-size-fits-all”, approach used in the New Zealand tax system, and others alike, have created undue complexity for small businesses. This study reviews small business tax regimes and concessions currently implemented (or proposed) in different countries to relieve the compliance burden for smaller businesses. Australia, South Africa, the United Kingdom and the United States have either implemented a separate tax regime, or offers tax concessions to smaller business taxpayers. New Zealand on the other hand, presents minor ad hoc tax concessions for small business taxpayers, but since 2009, there have been proposals to change this system. This study evaluates and compares all the implemented (or proposed) regimes and concessions of the selected countries. Following from the case studies, interviews are conducted with tax professionals that have worked closely with smaller businesses, in order to shed light on the possibility of implementing a similar regime in New Zealand. The findings show that a small business tax regime has many avenues to consider, however, there is general consensus that suggests small business taxation should be kept as simple as possible. This thesis puts forward a baseline for further discussion and development of a small business regime to reduce compliance costs for smaller businesses.