He's a smart, talented guy, but it takes a very different set of skills to break other peoples' stuff than it does to create it in the first place. George never had much patience for the organization of people -- he's got something of a superiority complex, or at least he believes other people are almost always focused on the wrong things. This bias is true, to a degree, but it isn't perfectly true, and George was always destined to run with those who actually can and do give him a run for his money, and to run up against the limitations of his technical abilities.
Except he also jailbroke the first iPhone. Doing it twice is beyond impressive and proves he's the real deal.
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