This chapter explores the link between entrepreneurship and the larger project of reservation land tenure reform. Many scholars draw a connection between land-tenure design and economic development generally. This chapter provides a more detailed analysis of current reservation land tenure dynamics and the specific challenges these systems can create for private economic development. Despite this current system’s widely recognized economic and non-economic perils, successful reservation land reforms have proven incredibly difficult to achieve. In order to encourage more land-tenure innovation, this chapter flips the land reform conversation on its head. Instead of focusing solely on land reform strategies to promote economic development, this chapter explores how supporting entrepreneurship itself might, in turn, drive more experimental, innovative, and flexible land reform. Entrepreneurs tend to thrive in the kind of uncertain legal environment that is otherwise seen as a problem in Indian country, and entrepreneurs might therefore be uniquely well suited to navigate reservation legal landscapes in creative ways. Entrepreneurship can be a powerful catalyst both to improve reservation economies and to support Indigenous efforts to reclaim and sustain local land ethics and property law choices.