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James Dempsey is a fifteen-year Apple veteran gone indie. At Apple, he was an evangelist, technical trainer, curriculum manager, and software engineer, working on Aperture, iOS, and macOS releases Leopard through Lion. James recently set back out on his own after working to build a cloud computer for humankind’s information at Upthere. He is also the frontman of James Dempsey and the Breakpoints, a band that performs humorous original songs about technical topics. Their debut album Backtrace topped the iTunes comedy charts in the US, UK, and Canada, and reached #5 on the Billboard comedy album chart.