Not all products and services are needed or wanted by everyone nor does each segment make decisions that are homogeneous in nature. As such, generational decision making differences are important to understand for the entrepreneur who is seeking to grow their business model and properly allocate scare marketing resources. Taking this dynamic into account, the purpose of this theoretical paper is to differentiate between Generation Y (millennials) and the newly formed and loosely named Generation Z (iGen) with respect to the market segments of age, values, beliefs, and attitudes. In addition, strategy will be identified and evaluated with respect to how organizations solicit these two closely related, yet distinct generational markets based on their decision making process. To discern the unique generational differences and better build a theoretical construct, an exhaustive literature review of the two generations was conducted relative to the comparison of market segmentation and the decision making process. From the careful analysis of current scholarship, it appears there are several important distinguishing characteristics regarding their decision making process that must be considered by organizations. The identification of this divide is important to furthering the scholarship in this field, especially that of the under-researched Generation Z or iGen.