The essence of an entrepreneur's effort lie in finding solutions to challenges. Monetary profit is a byproduct of entrepreneur's success and not the main agenda or measure of it. This bare nature makes entrepreneurship a risky business. In spite of all the rigor and challenges, entrepreneurs never cease to exist; in fact now we are seeing an unprecedented surge in their numbers. This surge has changed the whole dynamics of the entrepreneurial environment. A study of changing norms, style and sentiment of entrepreneurs is in order. In this chapter we study changing times and style of entrepreneurship; the evolution of new age entrepreneurs and their approach. Is this trend lasting or will burst like a bubble? Is it increasing uncertainty at conventional jobs or people have developed a deep lust for entrepreneurship? With so many startups coming up these days, how to evaluate them? These are the few questions which have risen and await adequate response.