If you listen to Kanye's music, he is highly self-critical and introspective at many times. I think this is a type of fearlessness, specifically the ability to be so publicly vulnerable (though I don't know if that's what GP had in mind).
Kanye's public image is reflective more of the pressures of his industry and how our celebrity culture depicts famous artists. However I think it goes beyond that to broader social and economic factors. Consider how many conversations there are on HN about dealing with imposter syndrome; if you compare Kanye's media portrayal and his music, I think there are strong parallels many people here could identify with.
Kanye's public image is reflective more of the pressures of his industry and how our celebrity culture depicts famous artists. However I think it goes beyond that to broader social and economic factors. Consider how many conversations there are on HN about dealing with imposter syndrome; if you compare Kanye's media portrayal and his music, I think there are strong parallels many people here could identify with.