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Housing.com is a real estate online search portal. Its growth potential had attracted investors who eventually became the major stakeholders in the company. Rahul Yadav, the brain child behind Housing.com, was an aggressive entrepreneur who used to push his opinions on the investors and even sometimes publicly criticized them. This created a rift between him and the investors. Investors tried to pacify the situation, but he was not ready to accommodate. On account of majority stake in the company, the investors had more veto power, as such, they asked him to leave the company that he had created. The case captures the pattern of evolution of a successful start-up - Housing.com - through a series of events and incidents highlighting the role of relationship with the investors. The case concludes by describing the inertia and the threat, the two components of the immaturity of an entrepreneur, as an impediment to the successful transition of a start-up firm.