We propose a new approach to apply the chaining technique in conjunction with information-theoretic measures to bound the generalization error of machine learning algorithms. Different from the deterministic chaining approach based on hierarchical partitions of a metric space, previously proposed by Asadi et al., we propose a stochastic chaining approach, which replaces the hierarchical partitions with an abstracted Markovian model borrowed from successive refinement source coding. This approach has three benefits over deterministic chaining: (1) the metric space is not necessarily bounded, (2) facilitation of subsequent analysis to yield more explicit bound, and (3) further opportunity to optimize the bound by removing the geometric rigidity of the partitions. The proposed approach includes the traditional chaining as a special case, and can therefore also utilize any deterministic chaining construction. We illustrate these benefits using the problem of estimating Gaussian mean and that of phase retrieval. For the former, we derive a bound that provides an order-wise improvement over previous results, and for the latter we provide a stochastic chain that allows optimization over the chaining parameter.
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