The retrofit of buildings to improve energy performance represents a vast opportunity in the construction market with potential to create jobs, reduce energy demand, and achieve subsequent o environmental benefits. Multiple challenges need to be overcome to "unleash" this potential and realize the benefits of investments in improving building energy performance. While large facilities often have easily predictable energy saving potential at scales that are attractive to the financial industry, they are often pursued in a manner that achieves only "low hanging fruit" for short term economic return. As a consequence, they often fall short of their potential to be pursued as an integrative and long term solution. Small and medium sized buildings face even more significant challenges due to the lack of owners' ability to manage and finance energy efficiency improvements. This research examines a regenerative approach to energy efficiency project development and construction in a regionally focused approach. The use of regenerative business principles, process mapping, and risk analysis to better describe and inform retrofit project investments is presented. Three resulting strategies to reduce risk and advance energy retrofit projects are described.