"I got turned down by every major record label who I met with - including Sony (Legend's current record label) - and you know, I had to keep persisting despite the no's and wait till I got to yes," Legend said.
However, the Oscar-winning singer feels the rejection was "helpful" as he had already tasted the real world before becoming successful.
"I think it was helpful for me to become famous when I was an adult already; I was twenty-six years old. I think it's harder for people that become famous when they're a lot younger because you never had to be an adult without being in this very unrealistic world.
"It is unrealistic if you don't know what the real world is like and me having lived in the real world for a while was very helpful," he said.