Entrepreneurship ventures are not new to India. They have been instrumental in developing the socio-economic scenario in the country. Many leading business houses today in India were family enterprises in their days of beginning. The latest trend is that India is reaping dividend because of larger percentage of youth in its population, who are venturing into innovative startups. With startups coming up in large numbers, Indian employment scenario is changing very fast. An entrepreneur starts a venture with her own will and might, and thus there are many important factors in such drive. A budding entrepreneur can come from any walk of life. However, a trained technical and/or managerial person may make a difference. Encountered with a challenging situation, a budding entrepreneur often finds himself at cross roads in her journey of life. This paper explores entrepreneurial narratives and classifies them into multi-criterion decision scenario faced at an individual level by an entrepreneur. Following a qualitative-quantitative research (mixed) approach, the paper shows outcome across two stages. Using qualitative research methods (e.g. Focus Group Discussion), a list of factors affecting motivation of someone to start an enterprise (called “startup”) is obtained. Subsequently, an analytic hierarchy process (AHP) model has been used under quantitative paradigm. This approach used Decision Analysis Module for Excel (DAME) add-in on MS-Excel to analyze responses obtained on the aforesaid list of factors from subjects with entrepreneurial mindsets. It was found that the risk taking ability depends on situation a youth is facing. However, turbulence in socio-economic environment diminishes the risk appetite. Strategic option such as “Focus” which is one when barriers to entry are higher and very select competitors can get into the spectrum; and it is better coupled with low exit barrier for a fail-safe and fast-exit plan.