We explore the regulation of new software platforms that connect consumers with informal service providers for transportation, short-term rentals, and more. These platforms tend to be in tension with existing regulatory frameworks which typically require licensing, certification, and insurance. In one view, some of these requirements are outdated or protectionist, benefiting incumbents more than consumers. Others counter that the rules embody important values and protect both customers and the public at large. We explore these disagreements with an eye for how the regulatory framework might allow the key efficiencies these platforms provide, while assuring protection for customers and avoiding harm to noncustomers.