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This paper attempts to evaluate a dotcom start-up company and a professional young basketball player using Real Option Analysis in the investors’ points of view. That is, we are standing in the financers’ shoes and valuing both cases if they are worth investing in. We believe that real option analysis is the most appropriate valuation method from our current knowledge compared to other traditional valuation methods notably like the Net Present Value (NPV), therefore we try to prove that using both qualitative and quantitative descriptions. The authors concentrate more on applying quantitative methods than giving detailed definitions of real options. Binomial Pricing Model and Monte Carlo simulation with the help of MS Excel and MATLAB were used in the evaluation. The paper consists of two case studies, each tackled differently but both summarized up all together. The paper concludes with a table exhibiting when real options are valuable and a belief that game theory is essential in ROA.