This paper departs from an analogy of sailing race instruments to demonstrate the potential of automation systems on the house performance and, more important, on impacting households for a more sustainable behavior. Sailing instruments have positively influenced the results on experienced sailors’ speed and ultimately have confirmed their observations on nature cycles. We have presented two research projects for the development of Building Management Systems for a house that relies mostly on natural ventilation and thermal mass and another one, based on a complex conditioning system with a solar assited HVAC system, connected to a Phase Change Material thermal storage. Our argument is that if research on the sailing tournament America’s Cup instruments soon became available to other sailing boats, systems developed to the Solar Decathlon houses’ academic competition could, and should, be accessible to a great number of home owners. These two research projects give evidence that further research should be guided to more sustainable BMSs, which could significantly contribute to households’ behavior changes and ultimately support dwellers reconnection to natural cycles.