While on vacation, Jenny encountered a strange change machine. Given a nickel, the machine outputs five pennies; given a dime, the machine outputs two nickels; given a quarter, the machine outputs two dimes and a nickel; given a dollar, the machine outputs four quarters, and given a five-dollar bill, the machine outputs five one-dollar bills. How many times must Jenny use the change machine in order to convert a five-dollar bill into 500 pennies?