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Snapchat has long positioned itself as the place for advertisers to reach millennials while its closest competitor, Facebook, is stuck with the olds. But on Thursday, Snap executives got a lesson in the terrifying, fickle nature of its young influencers, to the tune of a $1.3 billion loss.

Snap, the parent company of Snapchat, saw its stock price drop from $19.02 per share to $17.14 over the last 24 hours. Taking a look at the company’s pricing chart, you can see that it has been on a slight downturn all week after users complained about the app’s redesign and CEO Evan Spiegel responded that the complaints just “reinforce” the philosophy behind the changes. On Wednesday, the company released a more diplomatic response that included a reassurance that it “will always listen closely to find new ways to make the service better for everyone.” Suddenly, the stock price saw an uptick. Then, Kylie tweeted.

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“Ugh.” “Sad.” No words from the mouth of a young reality TV star could be more damning. Snapchat is so over. Jenner followed up with the backhanded compliment, “still love you tho snap ... my first love.” God, it’s even worse. It’s like Jenner sees Snapchat as the Friendster of the 2010s, something to wax nostalgic about but never go back to.

First, Snapchat organized its celebrity influencers into a different feed than users’ average everyday friends, and users complained that it felt like the celebrities were no longer their friends. Spiegel correctly pointed out that these celebrities aren’t your friend. And now, celebrity Kylie Jenner, with her 24 million Twitter followers, is no longer Snapchat’s friend.

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Snap lost a little over a billion dollars from its market value, but the company announced on Thursday that Spiegel will receive a $636.6 million stock grant for... I don’t know. The dancing hot dog, I guess.