A method and apparatus for evaluating an impact of enterprise investment agreement provisions on payoffs to equity holders, including investors and entrepreneurs. An investment agreement evaluator comprises a data collector, analyzer and report generator. One embodiment evaluates the impact of Venture Capital term sheet provisions. The data collector gathers information which includes term sheet provisions, enterprise forecasts and market forecasts. The analyzer determines the probability distribution for future payoffs to equity holders and estimates the current market value of equity held by equity holders. The report generator presents the evaluator results. Another embodiment analyzes definitive VC investment agreements. Other embodiments are described and shown through the use of the evaluator, entrepreneurs increasing their effectiveness in negotiating VC deals, VC attorneys expanding value-added services and increasing customer satisfaction. Venture Capitalists using the elevator increase returns for their investment portfolio.