Answer:
The probability that you win at least $1 both times is 0.25 = 25%.
Step-by-step explanation:
For each game, there are only two possible outcomes. Either you win at least $1, or you do not. Games are independent. This means that the binomial probability distribution is used to solve this question.
Binomial probability distribution
The binomial probability is the probability of exactly x successes on n repeated trials, and X can only have two outcomes.

In which
is the number of different combinations of x objects from a set of n elements, given by the following formula.

And p is the probability of X happening.
Probability of winning at least $1 on a single game:
The die has 6 sides.
If it lands on 4, 5 or 6(either of the three sides), you win at least $1. So

You are going to play the game twice.
This means that 
The probability that you win at least $1 both times is
This is P(X = 2).


The probability that you win at least $1 both times is 0.25 = 25%.