Kylie Jenner

Growing up on Keeping Up with the Kardashians meant most people watched her get braces and bad haircuts. What they didn't expect was what she'd do with a lip filler controversy. In 2014, her fuller lips became tabloid fodder; she denied it for months, then admitted it, then used the entire saga as market research. The Kylie Lip Kits launched November 2015 with $250,000 of her own modeling money and 15,000 units. They sold out almost instantly and generated $420,000 in revenue. By end of 2016, the brand had cleared $300 million with no factories, no warehouses, just 400 million social media followers.

The Forbes 'youngest self-made billionaire' cover came in March 2019. Forbes took it back in May 2020, alleging her team had submitted inflated or falsified financial documents. The real 2018 revenue was reportedly closer to $125 million, not the $360 million she claimed. None of that stopped Coty from paying $600 million for a 51% stake in Kylie Cosmetics just months before the retraction. She retains a 44% stake. Forbes estimates her at around $670 million, which is still an absurd amount of money for someone who turned a lip filler admission into an empire before she turned 25.

When she tried to trademark her first name in 2015, the pop star who already owned it had objections. Kylie Minogue successfully blocked the application, citing brand confusion. She and Kendall co-authored a dystopian novel, Rebels: City of Indra, but ghostwriter Maya Sloan confirmed the Jenners wrote only a two-page outline and Sloan did the rest. The person who turned a lip filler admission into a $600 million brand deal reportedly goes completely bare-faced most days.