With the launch of her lip kits — and the aid of Kris Jenner's business acumen — Kylie Jenner emerges as the biggest earner in the family. Kylie Cosmetics sells millions of dollars worth of makeup, and puts her on track to become the youngest self-made billionaire ever. But the family is facing setbacks. When Caitlyn Jenner (formerly Bruce) comes out as a transgender woman, the partnership that launched the Kardashian-Jenner dynasty ends, as Caitlyn and Kris go their separate ways. And the Kardashians come under increasing fire for their record of cultural appropriation, which reaches fever pitch when Kendall Jenner stars in an ill-conceived Pepsi commercial.