This dissertation studies the relationship between entrepreneurship, labor markets, and business cycles. Chapter 1 studies how the labor market conditions affect the formation and growth potential of new businesses over the business cycle. I develop a dynamic occupational choice model with labor market frictions and joint firm and worker dynamics, in which heterogeneous individuals choose between being employed/unemployed workers, subsistence self-employed, or entrepreneurs with potential to grow. Using U.S data, I provide support for the following predictions. First, unemployment makes more people willing to start a business because of the lower outside option. Second, a lower job finding rate reduces the value of the fallback option when...