We consider the fundamental problem of prediction with expert advice where the experts are "optimizable": there is a black-box optimization oracle that can be used to compute, in constant time, the leading expert in retrospect at any point in time. In this setting, we give a novel online algorithm that attains vanishing regret with respect to \(N\) experts in total \(\widetilde{O}(\sqrt{N})\) computation time. We also give a lower bound showing that this running time cannot be improved (up to log factors) in the oracle model, thereby exhibiting a quadratic speedup as compared to the standard, oracle-free setting where the required time for vanishing regret is \(\widetilde{\Theta}(N)\). These results demonstrate an exponential gap between the power of optimization in online learning and its power in statistical learning: in the latter, an optimization oracle---i.e., an efficient empirical risk minimizer---allows to learn a finite hypothesis class of size \(N\) in time \(O(\log{N})\). We also study the implications of our results to learning in repeated zero-sum games, in a setting where the players have access to oracles that compute, in constant time, their best-response to any mixed strategy of their opponent. We show that the runtime required for approximating the minimax value of the game in this setting is \(\widetilde{\Theta}(\sqrt{N})\), yielding again a quadratic improvement upon the oracle-free setting, where \(\widetilde{\Theta}(N)\) is known to be tight.