I think Dexter admires people w/ Callum's on paper academic achievement. He seems to equate it w/ intelligence. I guess when you're young and in school and everyone is stressing how important an education is you do get the idea in your head that being smart is way you get somewhere in life. So I can kind of understand that if Dexter didn't have an easy time of it at school whether it was from his dyslexia and or other reasons than it might be the cause of some low self esteem when it comes to how smart he thinks he is. I kind of gathered from last night that may be teachers and other students in school weren't very sympathetic to his struggles in school and may have been mean to him about it.
I think that Dexter sees his success in his businesses as a real triumph bc he was told all his life that he wasn't going to get anywhere bc of his lack of smarts. I think after an amount of time Dexter decided to spin his successes in a positive way and as proof of his intelligence and just began to call himself intelligent bc it feels good to him to believe that he is. However, that doesn't mean that some of his new found self esteem and deeming himself intelligent isn't a front for him and that he still really carries the hurt from his earlier years in which he felt stupid with him.