Currently, most teachers in the state of Maryland are employed by a local Board of Education and are direct employees of the school system. However, a better arrangement is possible. What if all Maryland schools districts could hire employees under their existing union-negotiated agreements and could also sign contracts with education companies, individual teachers, and other unions? This paper examines how this approach would work, the policy changes needed to enable teacher entrepreneurship, and the potential benefits, and also answers the common arguments for a single, union-negotiated contract.