Among the many contributions that Judith Freedman has made to tax law and policy in the United Kingdom and around the world, one of the most sustained and significant involves the regulation and taxation of small business. This article reviews Professor Freedman’s contributions to tax law and policy regarding small business, and evaluates Canadian experience with the taxation of private companies and their shareholders in light of Professor Freedman’s work. Part II summarizes Professor Freedman’s main conclusions regarding the taxation of small business, addressing both the taxation of similar economic activities conducted through different legal forms and the rationale and effectiveness of special tax preferences for small business. Part III examines Canadian experience with the taxation of private companies and their shareholders, illustrating the ways in which Professor Freedman’s concerns about structural tax differentials and tax preferences for small business have played out in the Canadian context. Part IV concludes with a few observations about how best to promote simplicity, neutrality and coherence in the taxation of small business
