Abstract:This paper presents a framework for predicting rare, high-impact outcomes by integrating large language models (LLMs) with a multi-model machine learning (ML) architecture. The approach combines the predictive strength of black-box models with the interpretability required for reliable decision-making. We use LLM-powered feature engineering to extract and synthesize complex signals from unstructured data, which are then processed within a layered ensemble of models including XGBoost, Random Forest, and Linear Regression. The ensemble first produces a continuous estimate of success likelihood, which is then thresholded to produce a binary rare-event prediction. We apply this framework to the domain of Venture Capital (VC), where investors must evaluate startups with limited and noisy early-stage data. The empirical results show strong performance: the model achieves precision between 9.8X and 11.1X the random classifier baseline in three independent test subsets. Feature sensitivity analysis further reveals interpretable success drivers: the startup's category list accounts for 15.6% of predictive influence, followed by the number of founders, while education level and domain expertise contribute smaller yet consistent effects.