Optimal stopping is the problem of deciding the right time at which to take a particular action in a stochastic system, in order to maximize an expected reward. It has many applications in areas such as finance, healthcare, and statistics. In this paper, we employ deep Reinforcement Learning (RL) to learn optimal stopping policies in two financial engineering applications: namely option pricing, and optimal option exercise. We present for the first time a comprehensive empirical evaluation of the quality of optimal stopping policies identified by three state of the art deep RL algorithms: double deep Q-learning (DDQN), categorical distributional RL (C51), and Implicit Quantile Networks (IQN). In the case of option pricing, our findings indicate that in a theoretical Black-Schole environment, IQN successfully identifies nearly optimal prices. On the other hand, it is slightly outperformed by C51 when confronted to real stock data movements in a put option exercise problem that involves assets from the S&P500 index. More importantly, the C51 algorithm is able to identify an optimal stopping policy that achieves 8% more out-of-sample returns than the best of four natural benchmark policies. We conclude with a discussion of our findings which should pave the way for relevant future research.

We propose a data-driven portfolio selection model that integrates side information, conditional estimation and robustness using the framework of distributionally robust optimization. Conditioning on the observed side information, the portfolio manager solves an allocation problem that minimizes the worst-case conditional risk-return trade-off, subject to all possible perturbations of the covariate-return probability distribution in an optimal transport ambiguity set. Despite the non-linearity of the objective function in the probability measure, we show that the distributionally robust portfolio allocation with side information problem can be reformulated as a finite-dimensional optimization problem. If portfolio decisions are made based on either the mean-variance or the mean-Conditional Value-at-Risk criterion, the resulting reformulation can be further simplified to second-order or semi-definite cone programs. Empirical studies in the US and Chinese equity markets demonstrate the advantage of our integrative framework against other benchmarks.

Conditional estimation given specific covariate values (i.e., local conditional estimation or functional estimation) is ubiquitously useful with applications in engineering, social and natural sciences. Existing data-driven non-parametric estimators mostly focus on structured homogeneous data (e.g., weakly independent and stationary data), thus they are sensitive to adversarial noise and may perform poorly under a low sample size. To alleviate these issues, we propose a new distributionally robust estimator that generates non-parametric local estimates by minimizing the worst-case conditional expected loss over all adversarial distributions in a Wasserstein ambiguity set. We show that despite being generally intractable, the local estimator can be efficiently found via convex optimization under broadly applicable settings, and it is robust to the corruption and heterogeneity of the data. Experiments with synthetic and MNIST datasets show the competitive performance of this new class of estimators.