In this study, we investigate the application of deep neural networks for predictive analytics in the realm of alternative asset portfolio management, focusing on Trading Card Games (TCGs) like Pokemon. Our primary objective is to understand the optimal trading cards for investment and to determine the appropriate timing for divestment and retention of these assets. Drawing on the successful implementation of machine learning predictive analytics in traditional financial markets, we aim to extend these techniques to alternative investments. To achieve this, we employ a two-pronged approach using a comprehensive dataset of historical sales values for Pokemon TCGs spanning five years, comprising over 200 million unlabeled data points. The first approach utilizes a semi-supervised sequence learning method, where a Long Short-Term Memory (LSTM) model is initially trained as a sequence autoencoder. The pre-trained model's weights are then used in a supervised phase to fine-tune the predictions for future trading card values. The second approach involves heuristic pretraining, which leverages market-derived indicators from existing literature to bridge the gap between traditional feature engineering and deep learning methods. Our technology stack is designed to handle end-to-end data collection, analytics generation, and execution of recommended trading strategies. Simulated backtesting results demonstrate that our Digital Grading Company (DGC) portfolio model outperforms traditional indices, achieving a 357% return compared to the 61% return of the S&P 500 Index over the same period. Real-time analysis further indicates that our model consistently identifies profitable trading opportunities in the TCG market using hourly data and proprietary algorithmic trade logic, executing trades 24/7. The DGC Predictive Portfolio, based on ungraded Pokemon TCG trading cards, also shows superior performance when compared to the Nasdaq 100 Index (Invesco QQQ ETF). Our analytics framework not only predicts the direction of price movement but also provides insights into the magnitude of changes, enabling a more dynamic and responsive trading strategy. The findings suggest that the integration of deep learning models with heuristic indicators has the potential to revolutionize portfolio management in alternative investments, paving the way for more accurate and profitable decision-making in niche markets. This research highlights the promising role of machine learning in enhancing alternative asset management strategies, suggesting future applications in other asset classes. We conclude that deep neural networks, when combined with data-driven heuristics, can significantly enhance trading outcomes, making them valuable tools for investors in the evolving landscape of alternative investments.