Over the course of it's beta, from 2003 to 2007, Second Life transformed in vision from a peer-to-peer market society with no hierarchies and no scarcity, to a hypercapitalist society, driven by corporate verticals and labor exploitation. How did this happen? The aim of this talk is to surface patterns in communities, cultures, and socio-technical systems that make labor ownership difficult to build and enforce. Ultimately, we look toward the question: How can we prevent the present generation of idealistic developers, bent on subverting traditional mechanisms of application and data control, from falling into the same trap as Second Life?