Your math is off -- if it reached $5, he'd have made $250. I think you were counting in cents. To convince yourself:
>>> total = 0
>>> for i in range(5, 500, 5):
... total += i
>>> total
24750
Hey you're right, my bad.
>>> total = 0
>>> for i in range(5, 500, 5):
... total += i
>>> total
24750
If it reached 5$, he'd have made 25,000$