How does he have the nerve to do something like this? I want to be this bold. How can I?

My best friend is a guy. I really dont think he's gay but I really don't care. He's my best friend. Anyways, he's a cosmetic artist at the M.A.C. Store. He's amazing at it too. He does my makeup for big events. I've seen him make 40 year old women look like they're 25. He stands there proudly while pickup truck cowboys (who know nothing about masculinity) point and laugh. How is he this confident and brave?