And the strategy is almost the simpliest: wage repeatedly $1. Either you win $1 (probability 90%) or you lose $1 (probability 10%). A result from probability theory tells you that, starting from $1000, your amount of money with this strategy will go to if you play repeatedly, and you will get ruined (i.e. have $0 left at some time) with probability which is a really really tiny probability. That's not surprising: it is far more likely to win $1 than to lose $1, and being broke happens if your number of losses exceeds the number of wins by 1000 at some time.