Artificial Intelligence has been around for almost 70 years, but only in recent years has it become a major disrupter for many industries due to the convergence of big data, processing power and cloud computing. This has led to the development of “deep learning”, which allows a type of computer intelligence that closely mimics human decision-making. In this paper, I take look at the evolution of Artificial Intelligence, along with two disparate industries: Retail and Real Estate. These industries have adopted AI at different speeds. Also, each industry has its own form of resistance and uses for the technology. My theory is that there are forms of technology resistance by major players in the real estate industry in combination with the long industry cycles that are causing slow adoption.