Before GirlBoss was a book or a Netflix show or a hashtag, Sophia Amoruso was running NastyGal and reticent to even sit on stage and be interviewed. She finally relented, and this was one of the first she’d ever done.

This interview was situated almost exactly between a five-year, almost effortless success story of growth, and a five-year slog that ultimately ended in bankruptcy.

But while NastyGal ultimately didn’t work, Amoruso continues to find ways to productize her unique attitude, style and eye. In addition to executive producing the Netflix show based on her life, she’s recently launched a media company for women called GirlBoss Media.

I have mixed feelings on the show and the direction of her media company, as a woman who doesn’t pa...