When a friend first approached Caldwell to become a life insurance agent, he wasn’t interested. He thought it would be too hard, but his friend encouraged him, saying, “You’ve got the gift of gab; you’re good at sales. Why not give it a try?” Caldwell agreed to enroll in an apprentice course and take the exam to become an insurance broker. He failed the exam on his first try, but that only fueled his determination. He kept studying and, the next time he took the test, he passed.