That's a good question to ask! Although we know that Dexter is ambitious and even greedy, he also doesn't usually go around making a show of his success or telling people about it, unless it's for a good reason.
This conversation of his with Judy takes place in Section III of the story, when they're having their first official date. They are talking on the porch after dinner, and Judy complains about being disappointed by another guy. This other fellow had charmed Judy, and she cared about him, but then he revealed to her that he was very poor. Naturally, considering Judy's somewhat snobby upbringing in a wealthy family, she had to break up with this guy; it disappointed her. "He didn't start right," she complains to Dexter, meaning that this fellow hadn't given her all the details of his situation from the beginning.
Wanting to "start right" with Judy by telling her honestly what his financial situation is, Dexter confesses how he's actually made himself extremely wealthy even though he's still young. Dexter also probably senses that this information about his wealth will make him more appealing to Judy, and it does. As soon as he tells her this, she kisses him passionately.
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