Write down all of the numbers that you can roll that result in you winning at least $1 for a single roll of the die. Then, figure out the probability of getting a successful roll for the first game. Then, multiply it by the probability of getting a successful roll for the second game.
So, if you were asked the probability that you would win exactly $1 both times, you have two numbers you can roll out of six each time you roll the die. So, the probability is .
Now, alter the problem when you are looking for the probability that you must win at least $1 both times. How many numbers can you roll out of six?