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James Hobson began publishing videos on YouTube in 2006, when he was still a high-school student in Ontario, Canada. His early uploads were crude by today’s standards—some gymnastics tricks, some parkour, and some mildly anarchic silliness (for example, a 2009 clip of Hobson drinking raw eggs). “It was just the easiest way of sharing videos with my friends,” Hobson told me recently. “I would upload on YouTube and then share a...