As mentioned above, Dexter was only fourteen but renowned as the best caddy there ever was. He was so diligent at his job that he never lost a ball, causing all golfers to prefer him over every other caddy. In fact, his 30 dollar monthly salary was unheard of in his town. He opts out of attending the State University and instead chooses to attend a well known one so that he can mingle with the affluent because he wanted what they have. At only twenty three years of age, Dexter took out a loan against his college degree so as to invest in a laundry business partnership. Even though this business was small, Dexter devoted himself to learn how to handle linen without causing shrinkage and within no time, every wealthy golfer sought his service. Dexter’s business acumen propelled the expansion of the business and he opened five branches across the city and also ventured into the lingerie business. He did all the above before attaining the age of twenty seven.
At fourteen, Dexter is such a good caddy that all of the golfers request him more than any other caddy. He has many "winter dreams" of a bright, successful future. When Judy Jones makes him feel inferior, however, he quits his job and decides he must make something of himself. He goes to a prestigious college back East and becomes a successful business through hard work. He learns everything he can about the cleaning trade in order to be the best he can. He improves his manners and the way he dresses to be able to fit into the world of money. He has a vision of creating a perfect life in order to have the things that the wealthy men he used to caddy for had. Dexter was not lacking in ambition and achieved the success he thought would make him happy.