A gambler with an initial bankroll is faced with a finite sequence of identical and independent bets. For each bet, he may wager up to his current bankroll, and will win this amount with probability p or lose it with probability 1-p. His problem is to devise a wagering strategy that will maximize his final expected utility with the side condition that the total amount wagered (i.e. the total ‘action’) be at least his initial bankroll. Our main result is an expression that characterizes when the strategy of placing equal-sized wagers on all bets is optimal. In particular, for a given bankroll B, utility function f (concave, increasing, differentiable), and n bets, we show that it is optimal to wager b/n on each bet if and only if the probability of winning each bet is less than or equal to some value p⋆∈[½,1] (where p⋆ is an explicit function of B, f, and n). We prove the result by using a basic nonlinear programming technique.