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Examining The Tax Advantage Of Founders' Stock, Gregg D. Polsky, Brant J. Hellwig

Scholarly Articles

Recent commentary has described founders' stock as tax-advantaged because it converts founders' compensation income into capital gains. In this paper we describe various founders' stock strategies that offer this character conversion and then analyze whether they are, on the whole, tax advantageous. While the founders' stock strategies favorably convert the character of the founders' income, they simultaneously turn the company's compensation deductions into non-deductions. Whether founders' stock is tax-advantaged overall depends on whether the benefit of the founders' character conversion outweighs the cost of the company's lost deductions. We use various hypothetical to illustrate this tradeoff. We conclude that founders' …