Among many ambiguous terms, one of the famous ambiguous terms is “Entrepreneurship”. Explaining “who is really an entrepreneur” is one of the most difficult jobs. Some say that entrepreneurship is primarily related to “innovation”. But, for the majority group, it means “risk-taking”. For a layman it means “a newbie in the market” or “starting, owning and managing a new business”. If things are so complicated, then why should anyone be a rural entrepreneur? But it has emerged as a major opportunity for the people who are forced to either migrate from rural to urban areas or from the semi-urban areas to major industrial centers and cities. The rural entrepreneur should be capable of exploiting the government policies and schemes so that he/she can rise on the ladder of success in the cut-throat competition of the market. This kind of efforts needs appreciation and support from the kin group, social networks of the entrepreneur, government official (which is very difficult to even imagine?) and the public at large. This process will help in changing Indian rurality/rural world into a real place of opportunities. It is a well-known fact that rural entrepreneurs are facing major challenges due to non-availability of basic facilities and environment for doing business/ease of doing business in the rural areas. Besides this, rural entrepreneurs face tough competition from giant urban businesses and established urban entrepreneurs. They incur the high cost of production due to high input cost. Because of these kinds of enormous problems present in rural business space the “middlemen” often, exploit rural entrepreneurs. Generally, the rural entrepreneurs have been seen to depend on the middlemen for marketing of their products who frankly speaking pickpocket their hard earned profit. Storage facilities and poor means of communication, as well as marketing problems, create hurdles in the path of success in “rural entrepreneurs”. The environment in the family, society and the support system (the family, friends, relatives, government and fellow businessmen/businesswomen) is not generally conducive to inspire rural youth or any other aspiring person to take up entrepreneurship as a vocation. The absence of financial support and access to cheap capital to rural businesses is one of the most heartbreaking reasons for a young person to go for start-ups and pursue any kind of new business in the rural areas. This paper makes an effort to understand these problems, hurdles when any entrepreneurship takes some kind of shape, and other covert and overt challenges faced by these rural folks every day while pursuing their passion.