We study the decision theory of a maximally risk-averse investor --- one whose objective, in the face of stochastic uncertainties, is to minimize the probability of ever going broke. With a view to developing the mathematical basics of such a theory, we start with a very simple model and obtain the following results: a characterization of best play by investors; an explanation of why poor and rich players may have different best strategies; an explanation of why expectation-maximization is not necessarily the best strategy even for rich players. For computation of optimal play, we show how to apply the Value Iteration method, and prove a bound on its convergence rate.