I recommend the Behind the Bastards episode on him. He had a ton of opportunities available to him normal people don't, including ones that aren't strictly financial. For instance, he was allowed to ignore most of his other subjects in high school to concentrate on computer stuff. As a person who had similar interests in computers and sometimes not an interest in some other classes, that's a huge advantage.

While I didn't have too hard a time in school (only needed 2 classes to pass my final year), being able to concentrate on just computers(which were my electives) would have been far less stressful and would have allowed more concentration. That's just one of many intangible benefits.