We consider a discrete-time, linear state equation with delay which arises as a model for a trader's account value when buying and selling a risky asset in a financial market. The state equation includes a nonnegative feedback gain α and a sequence v(k) which models asset returns which are within known bounds but otherwise arbitrary. We introduce two thresholds, α− and α+, depending on these bounds, and prove that for α < α−, state positivity is guaranteed for all time and all asset-return sequences; i.e., bankruptcy is ruled out and positive solutions of the state equation are continuable indefinitely. On the other hand, for α > α+, we show that there is always a sequence of asset returns for which the state fails to be positive for all time; i.e., along this sequence, bankruptcy occurs and the solution of the state equation ceases to be meaningful after some finite time. Finally, this paper also includes a conjecture which says that for the "gap" interval α− ≤ α ≤ α+, state positivity is also guaranteed for all time. Support for the conjecture, both theoretical and computational, is provided.