A Scenarios approach will present examples that will allow business savvy professionals to make informed decisions based on a sound business model. This model will cover the technology options in detail as well a financial analysis. A TCO (Total Cost of Ownership) as well as an ROI (Return on Investment) will show how to start, develop and formulate a business case that will allow for both small and large scale projects achieve the goal of deciding to proceed with Cloud Computing options. A risk based analysis will also be covered with examples showing how one an ascertain risk metrics balanced with technology options driven to a sound financial backing. Examples will include leveraging VMware virtualization, Cloud IaaS (Infrastructure as a Service).