Software is an interesting and attractive business. Software business creates not only millionaires but also the bubbles of .com. It has the high fixed cost but the cost of making one copy or million copies almost stays the same. To know whether a software business is a risk proposition or a good investment, this study will start from two dimensions in the analysis, product and user dimensions. By examining the external and internal variables, this analysis will describe the advantages and disadvantages of providing on-premises and on-cloud software, conclude the movements of software products. Followed by the product dimension, this analysis will give a breakdown in the user dimension. Then the movement of serving software users will be determined. Besides the industry movement within these two dimensions, software companies could examine themselves by the measurements and variables identified in this study.