The more monney you can bet, the higher are the chances to win.
If you play 1000 times 1 on the dice, you are still going to win a certain number of times, there are statistically good chances that you will be above at some point, all is too see how much can reasonably expect to gain with the 1000 rolls and stopping when it get close to that.
How much money do you have and how much are you betting on each roll? Let's say you have $1000 and bet $1 at a time, to make sure that you can last at least 1000 rolls. Statistically you will have lost $10 by the end of this game, assuming a typical 1% house edge - that's what you can reasonably expect.
Your chances to be "up" at any point during this game are not higher than the chances of winning any single bet, in fact they're getting lower because of the house edge slowly decreasing your bankroll.
If you bet more than $1 you'll be losing even more and increase your chances to go bankrupt before you reach 1000 rolls.