"I always thought my moment was just around the corner."

During this time he was rejected by all the major labels, sometimes more than once, Legend told UPenn students in 2014. "I played for all the giants of the business — Clive Davis, L.A. Reid, Jimmy Iovine, you name it. And all of them turned me down."

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“It's much cooler to be detached and apathetic, right? We all like a little snark and cynicism and irony, especially from our favorite artists and comedians and writers. I get it," Legend said at UPenn. "But that cool detachment only gets you so far. Passion gets you a lot further. It makes you a better entrepreneur, a better leader, a better philanthropist, a better friend, a better lover."