Deals in Venture Capital have certain elements in common: they take place in an uncertain environment. Thus, they require resolution of a few key questions, as: How are cash and risk allocated? What are the incentives for each of the partners in the deal? Beyond these basics, endless variations on a theme are possible. Through a series of examples illustrating important aspects in transactions between an entrepreneur and a venture capitalist, this dissertation suggests the various possibilities for structuring different term-sheets in a application using Monte Carlo simulation. This approach analyzes how the characteristics of contracts can be crucial in determining the ultimate value of the investment for both entrepreneur and venture capitalist.