Kylie Jenner is the Kardashian most closely molded in Kim’s image, both in style (they share a fondness for neutral color palettes and Balmain) and in her business acumen: WWD projected, in an analysis released Wednesday, that Kylie Cosmetics will bring in $1 billion per year by 2022. (It took Lancôme 80 years to reach this milestone.) But like Kim—and like all the Kardashians—this wide reach also means Kylie has confronted substantial criticism across her various ventures during her short-but-illustrious career. She was embroiled in controversy over a recent Puma campaign; her one-time relationship with the rapper Tyga was subject to intense scrutiny; and most recently, she was roundly criticized for collaborating with her brother Rob Kardashian just after his former girlfriend Blac Chyna was granted a restraining order against him. And that’s just the start: On the young entrepreneur’s 20th birthday, we look back on her first two decades of drama—not that she’s letting that hold her back.