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Fresh (Richfresh, Henry Mask) is a fashion designer based in Los Angeles. Fresh joins the Armchair Expert to talk about getting into fashion in middle school because he was told he didn’t dress well, teaching himself how to tailor suits because no one would apprentice him, and being the youngest and only black tailor in most shops in New York. Fresh explains how he ended up in a homeless shelter because of his drug addiction, raising a daughter on his own, and becoming a symbol of alpha male culture which he later rejected. Fresh talks about how his father’s passing affected his outlook on life, that he used to blame everyone else for his misfortunes, and how he identified the sacrifices he needed to make to achieve success.