We propose a new approach to portfolio optimization that utilizes a unique combination of synthetic data generation and a CVaR-constraint. We formulate the portfolio optimization problem as an asset allocation problem in which each asset class is accessed through a passive (index) fund. The asset-class weights are determined by solving an optimization problem which includes a CVaR-constraint. The optimization is carried out by means of a Modified CTGAN algorithm which incorporates features (contextual information) and is used to generate synthetic return scenarios, which, in turn, are fed into the optimization engine. For contextual information we rely on several points along the U.S. Treasury yield curve. The merits of this approach are demonstrated with an example based on ten asset classes (covering stocks, bonds, and commodities) over a fourteen-and-half year period (January 2008-June 2022). We also show that the synthetic generation process is able to capture well the key characteristics of the original data, and the optimization scheme results in portfolios that exhibit satisfactory out-of-sample performance. We also show that this approach outperforms the conventional equal-weights (1/N) asset allocation strategy and other optimization formulations based on historical data only.
The optimal allocation of assets has been widely discussed with the theoretical analysis of risk measures, and pessimism is one of the most attractive approaches beyond the conventional optimal portfolio model. The $\alpha$-risk plays a crucial role in deriving a broad class of pessimistic optimal portfolios. However, estimating an optimal portfolio assessed by a pessimistic risk is still challenging due to the absence of a computationally tractable model. In this study, we propose an integral of $\alpha$-risk called the \textit{uniform pessimistic risk} and the computational algorithm to obtain an optimal portfolio based on the risk. Further, we investigate the theoretical properties of the proposed risk in view of three different approaches: multiple quantile regression, the proper scoring rule, and distributionally robust optimization. Real data analysis of three stock datasets (S\&P500, CSI500, KOSPI200) demonstrates the usefulness of the proposed risk and portfolio model.