Photo Illustration: Aaron J. Thornton/Getty; Angela Weiss/Getty; Aïda Amer/Axios
The big picture: Jenner and her family have always had complete control over her image and her work product. As someone who made over $100 million by the age of 21, Jenner was under no pressure to sell the company that was generating all those profits, which meant that she could wait for a suitably desperate suitor to come along.
- Swift, by contrast, signed a six-album deal with Big Machine when she was 15 years old. While her father was smart enough to buy some equity in Big Machine as part of that deal, he's no Kris Jenner, and Swift herself didn't have megastar sisters blazing a trail in front of her.
- The result was that Swift had very little leverage earlier this year when she tried to regain control of her early music. In the end, Big Machine was sold to her arch-enemy Scooter Braun, who bought the label with the assistance of private-equity giant Carlyle Group.
Jenner was a trailblazer in her category, more or less inventing the concept of an asset-light, direct-to-consumer company making products sold primarily to her millions of Instagram followers.
- While her older sisters largely monetized their celebrity the old-fashioned way — being paid by brands to endorse or model products — Jenner realized that she could make much more money by creating her own brand and owning it 100%.
- Swift is more old-fashioned (and, arguably, talented). She was fighting Spotify, for instance, insisting on the primacy of album sales — long after almost all other artists had embraced streaming.
The capitalists on the other side of these deals also differ greatly.
- Coty, the French cosmetics giant, has made a very public bet on Jenner's future. Its interests are aligned with hers, and Jenner continues to hold all the cards. After all, if she gets bored or annoyed with the direction of Kylie Cosmetics, she can stop publicizing it and move on to the next thing. Coty can't move on: It's already $600 million in the hole and needs Kylie Cosmetics to continue to grow if it's going to reap a return on its investment.
- Carlyle made a bet on Swift's past, rather than her future — and did so by teaming up with her music industry enemy. That move ended up drawing the ire of Elizabeth Warren and also irked Swift so much that she now states that she wants to re-record all those old albums, thereby depriving Braun and Carlyle of much future income.
The bottom line: If you want to buy someone's entire life's work, it's best to do it with their consent.