WEBVTT

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Welcome back to the Deep Dive. It is Monday,

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February 2nd, 2026. And we have a big one today.

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We really do. We are opening up a file that honestly,

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it serves as the ultimate Rorschach test for

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how you view modern capitalism. That's a great

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way to put it. We're looking at a figure who

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has been in the public eye for nearly two decades

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now. Someone who essentially rewrote the playbook

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on monetization, influence and the very concept

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of reality. We are talking, of course, about

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Kylie Jenner. We are. And, you know, it is a

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fascinating time to be having this conversation.

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Sitting here in early 2026, Kylie is 28 years

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old. Right. And she is currently navigating what

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is, I think, arguably the most dangerous pivot

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of her career. The acting move. The acting move.

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She's moved away from the King Kylie era of pure

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influencer marketing. Yeah. And is attempting

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to break into serious acting with her role in

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the moment. A huge gamble. A massive one. Yeah.

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But understand, if this gamble is going to pay

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off, we have to go back. We have to understand

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the machine that got her here in the first place.

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Exactly. I think a lot of people see the Instagram

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grid, the Met Gala looks, you know, the headlines,

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and they just see celebrity. But when you actually

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dig into the stack of reports we have here, and

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we have a lot, the SEC filings from the Cordy

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deal, the trademark court transcripts, the supply

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chain audits, you realize this isn't just fluff.

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This is a case study in really aggressive business

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strategy. It really is. And our mission today

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is to unpack that strategy. We're going to look

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at how the youngest sibling, who was effectively

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a background character in the early days of Keeping

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Up with the Kardashians. She really was just

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sort of there. Leveraged a specific physical

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insecurity into a billion dollar conversation.

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And as I said, conversation, not necessarily

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billion dollar bank account. Yes. Because we

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are definitely going to get into the weeds of

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that Forbes scandal. The web of lies. We are

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absolutely going there. I can't wait. But before

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we get to the billions and the scandals, let's

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unpack the origin story. You have to. Because

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to understand Kylie in 2026, you have to remember

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who she was in, like, 2010. You have to go back

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to what I call the bundled era. The bundled era.

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That is such a good way to put it. Explain that.

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Well, think about it. She was born in 1997. The

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show premieres in 2007. She's nine years old.

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A child. A literal child. So for the first five

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or six years of her fame, she didn't have a solo

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identity in the marketplace. She was a package

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deal. It was always Kendall and Kylie. Always.

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I was looking through the notes on their early

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ventures and it is a trip down memory lane. I

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mean, they were throwing everything at the wall.

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Everything. You had the clothing line with PacSun

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in 2013, the Kendall and Kylie collection. Which

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for a mall brand was actually pretty successful.

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It was. Then you had the jewelry line with Glam

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House. They even had that ghost written sci -fi

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novel. Rebels. City of Indra. A classic of the

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genre. Yes. I completely forgot about this. It's

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such a fascinating artifact of celebrity branding.

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It was released in 2014. And you have to remember

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the context. Dystopia was huge because of the

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Hunger Games. Oh, it was everything. So, of course,

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they tried to capitalize on that trend. But the

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critical reception was, let's just call it brutal.

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Brutal is kind. I think it sold something like

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13 ,000 copies in the first four months. Which,

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for a celebrity book of that level, is a flop.

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And the controversy wasn't just that the book

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was, you know, not very good. It was the authorship.

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All right. That was the real issue. It was marketed

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very heavily as a novel by Kendall and Kylie

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Jenner. Their names were huge on the cover. Right.

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But then it came out that a writer named Maya

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Sloan was the actual author, the ghostwriter.

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Now, ghostwriting is totally standard in the

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industry. That's not the issue. Not at all. But

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usually, the celebrity provides the meat of the

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story, the characters, the plot points. In this

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case, the Jenner camp's defense was that the

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girls had, and this is a direct quote, numerous

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Skype and FaceTime calls with the writer. Numerous

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Skype calls. That is a very, very low bar for

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putting your name on the cover of a novel. It

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is, but it highlights the strategy of that whole

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era, brand slapping. Explain that. The idea was

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that the name Jenner was the value add, regardless

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of the product quality. The name itself was the

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asset. So it didn't matter if it was nail polish

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or a book. Exactly. Whether it was OPI nail polish

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or a sci -fi book, the product was secondary

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to the label. But the problem for Kylie was she

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didn't have her own label yet. She was just Kendall's

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sister. Kendall's little sister. Which brings

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us to the pivot point. I mean, this is the moment

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that changed the trajectory of the entire family

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business, really. It did. We're talking 2014

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and 2015. We're talking about the lips. This

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is the aha moment. And it's so fascinating because

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it's rooted in a very human, very relatable insecurity.

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I remember this so vividly. Her face started

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changing on Instagram. Her lips got significantly

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bigger and it happened like overnight. It was

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very sudden. And the media obsession shifted

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from what is she wearing to what did she do to

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her face? That was the only question anyone was

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asking. And for a long, long time, the strategy

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was denial. Complete and total denial. She claimed

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it was just lip liner. The overlining trick?

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She said she was overlining her lips to create

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an optical illusion. She gave tutorials on it.

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Which, I don't know if it was inadvertent or

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not, but it triggered the Kylie Jenner challenge.

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Oh, it wasn't inadvertent, the effect at least.

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And that challenge was a sociologically fascinating,

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if horrifying, Phenomenon. Horrifying is the

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word. You had thousands of teenagers, mostly

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young girls, suctioning their lips into shot

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glasses or water bottles to induce swelling,

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trying to mimic that look. People were bruising

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themselves, bursting blood vessels. It was actually

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dangerous. The photos were all over the Internet.

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It was incredibly dangerous. But from a business

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perspective, what did that tell her team? It's

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a proof of concept. It's hard data. It proved

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that her influence was so potent that people

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were willing to physically harm themselves to

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emulate her. That is a level of engagement that

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traditional advertising simply cannot buy. No

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amount of money gets you that. It showed that

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the market demand for being Kylie was astronomical.

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So after months of denial, she finally confesses

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in May 2015 on the show. She admits to the fillers.

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She does. And here is where the genius kicks

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in. Most publicists in that situation would say,

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OK. apologize for the lie, go quiet, let the

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news cycle turn. Disappear for a while. Right.

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Let people forget. Kylie's team, led by Kris

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Jenner, did the opposite. They operationalized

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the scandal. They monetized the insecurity. Exactly.

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Three months after the confession, three months,

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in August 2015, she announces the Kylie lip kit.

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It's so fast. She essentially said, you've been

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talking about my lips for a year. Fine. Here's

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the exact product to get them. She took ownership

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of the narrative. It turned the biggest tabloid

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negative into a product feature. It's brilliant

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marketing. And the execution of the launch was

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flawless. They used what we call the DRAP model,

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which was, as you said, borrowed from streetwear

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brands like Supreme. Right. They launched in

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November 2015 with an intentionally limited inventory

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to 15 ,000 kits. And they sold out in, what was

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it, under a minute. Seconds. Literally seconds.

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And because they sold out so fast, the narrative

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wasn't Kylie sells makeup. The narrative was

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Kylie breaks the Internet. The scarcity was the

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story. Precisely. That scarcity created panic

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buying for the next drop and the drop after that.

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By February 2016, she rebrands from the Simple

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Lip Kit to the full Kylie Cosmetics and Scales

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production, up to 500 ,000 kits. That is a massive

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scale -up in just a few months. It's an incredible

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jump. I want to talk about the cost structure

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here, because from the outside, the margins on

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this must have been insane. They were incredible.

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And this is key to understanding her wealth accumulation.

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This was a very lean, very asset light business

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model. What do you mean by that? She didn't build

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a factory. She didn't hire a massive logistics

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team or an R &amp;D department. Yeah. She's a white

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label manufacturer. So a company that already

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makes makeup for other people. Exactly. A company

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called Spatz Laboratories. And she used a company

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called Seed Beauty for the product development

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and fulfillment. She basically outsourced the

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entire back end of the business. So her overhead

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was tiny. Minimal. Her main cost was the cost

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of goods sold and her marketing cost. Effectively

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zero. She didn't buy TV ads. She didn't buy billboards.

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She just posted on Snapchat and Instagram to

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her tens of millions of followers. The glosses

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video. That's a perfect example. I remember that.

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It was like a little movie. Directed by a major

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music video director, Colin Tilly. It wasn't

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a commercial. It was a three -minute action movie

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where she's driving a Rolls Royce in the desert.

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There's a heist. It was content. Right. It blurred

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the line between entertainment and advertising

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in a way that was at the time really revolutionary

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for a cosmetics brand. So she has low overhead,

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zero marketing costs, and a product that sells

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out instantly. She is, for all intents and purposes,

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printing money. Which leads us directly to the

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magazine cover that started a war. Here we go.

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Part two. The billionaire wars. I feel like this

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is where the story gets really technical and

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really messy. It does, because we're moving from

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social media hype into the world of audited financials

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and SEC regulations. It's a whole different beast.

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It is. So fast forward to August 2018. Kylie

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is on the cover of Forbes. The headline estimates

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her net worth at $900 million. And she's only

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20 years old at this point. It's an unbelievable

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number. And then by March 2019. Forbes follows

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up and officially declares her the world's youngest

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self -made billionaire at age 21. She beat Mark

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Zuckerberg. That was the headline everywhere.

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Younger than the founder of Facebook. On paper,

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yes. Yeah. And this announcement sparked two

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massive simultaneous debates. The first was the

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cultural debate over the term self -made. Oh,

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people were furious. I remember the tweets. I

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remember the think pieces. How can you be self

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-made when you're born a Kardashian? It's a valid

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semantic argument. You know, critics argue that

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she was born on third base and thought she hit

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a triple. Right. She had inherited fame, capital

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from her family, a reality show platform, and

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a safety net that 99 .9 % of entrepreneurs just

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do not have. But her family and even people like

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Paris Hilton came out to defend her. They made

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the argument that she didn't inherit the business.

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She built the business using the platform she

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was given. Which is true. But that platform is

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a priceless asset. You can't separate the two.

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However, that entire cultural debate became secondary

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to the financial reality. It did. Because in

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May 2020, Forbes released a bombshell retraction.

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An entire article dedicated to walking it back.

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The headline was incredible. Inside Kylie Jenner's

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web of lies. You can't get much more direct than

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that. They didn't just walk back the number.

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They accused the Jenner camp of actively participating

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in financial engineering and deception. Okay,

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walk us through this. This is where it gets complicated.

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What exactly do Forbes accuse her of? So the

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primary source for that billionaire valuation,

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going back to the 2018 article, was tax returns

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and revenue figures provided directly by Kylie's

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team, specifically her mother and manager, Kris

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Jenner. Okay, so they were handing over documents.

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They were. And these documents claimed the business

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was generating somewhere between $360 million

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and $400 million a year in revenue. Massive numbers.

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And Forbes, a reputable financial magazine, believed

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them. They did. They published the numbers. The

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problem arose when Kylie sold a majority stake

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in her company. In November 2019, she sold a

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51 % stake in Kylie Cosmetics to the beauty conglomerate

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Coty. And she sold it for $600 million. A massive

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exit. $600 million in cash. On the surface, that

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seems to validate the billion -dollar valuation,

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right? A $600 million sale for 51 % values the

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company at roughly $1 .2 billion. Exactly. So

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what was the issue? Here's the catch. Cody is

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a publicly traded company. They are regulated

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by the SEC. They cannot lie to their shareholders

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about the financials of a company they just bought.

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It's illegal. So when Cody released their shareholder

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reports and their investor presentations about

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the acquisition, the real verified audited numbers

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for Kylie Cosmetics came out. And what were the

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real numbers? Kylie Cosmetics wasn't doing $360

00:12:26.399 --> 00:12:29.480
million a year. In 2018, for instance, it did

00:12:29.480 --> 00:12:33.240
about $125 million. Wow. That is that is a significant

00:12:33.240 --> 00:12:35.340
discrepancy. Less than half of what they were

00:12:35.340 --> 00:12:36.940
claiming. It's not even the same ballpark. So

00:12:36.940 --> 00:12:39.200
the implication from Forbes was that for years,

00:12:39.500 --> 00:12:41.860
the Jenner team had been inflating the numbers

00:12:41.860 --> 00:12:43.679
they were giving to the media. That was the direct

00:12:43.679 --> 00:12:46.379
accusation that they had fabricated revenue figures

00:12:46.379 --> 00:12:48.960
and forged tax documents to create the perception

00:12:48.960 --> 00:12:51.559
of a billion dollar brand. So the question is,

00:12:51.580 --> 00:12:54.500
why do that? She was already incredibly rich.

00:12:54.720 --> 00:12:58.039
Why risk fraud accusations just for a title?

00:12:58.179 --> 00:13:00.899
Because in the influencer economy. Perception

00:13:00.899 --> 00:13:04.399
is reality. The title billionaire is a marketing

00:13:04.399 --> 00:13:06.980
tool. It's the ultimate validation for the brand.

00:13:07.200 --> 00:13:09.539
It makes the product seem more desirable. It

00:13:09.539 --> 00:13:11.840
does. It signals to the world this is the winner.

00:13:11.980 --> 00:13:14.600
It creates a mythology around the founder that,

00:13:14.639 --> 00:13:18.519
in turn, drives sales. Being a billionaire wasn't

00:13:18.519 --> 00:13:20.500
just about her bank account. It was about the

00:13:20.500 --> 00:13:23.320
brand's story. So Forbes officially strips the

00:13:23.320 --> 00:13:27.320
title. How did Kylie respond to this Web of Lies

00:13:27.320 --> 00:13:30.350
article? She went straight to Twitter, now X,

00:13:30.429 --> 00:13:32.509
of course. Yeah. She posted a series of tweets

00:13:32.509 --> 00:13:34.450
denying that she'd ever asked for the title and

00:13:34.450 --> 00:13:36.409
denying that she'd ever lied. What was the quote?

00:13:36.610 --> 00:13:39.029
She wrote, I've never asked for any title or

00:13:39.029 --> 00:13:42.409
tried to lie my way there ever, period. But she

00:13:42.409 --> 00:13:44.289
didn't dispute the numbers from the Cotty deal?

00:13:44.450 --> 00:13:46.129
She couldn't. They were in public filings. So

00:13:46.129 --> 00:13:48.370
she sort of sidestepped the core accusation.

00:13:48.409 --> 00:13:50.289
But at the end of the day, she kept the $600

00:13:50.289 --> 00:13:53.309
million from Cotty. And frankly, even after the

00:13:53.309 --> 00:13:56.250
retraction. Forbes re -estimated her net worth

00:13:56.250 --> 00:13:59.830
at around $700 million. So while she wasn't a

00:13:59.830 --> 00:14:02.350
billionaire, she was still snaggeringly successful.

00:14:02.929 --> 00:14:07.129
But the web of lies story, it cracked the armor.

00:14:07.350 --> 00:14:09.730
It showed that the machine wasn't as invincible

00:14:09.730 --> 00:14:12.029
as it looked. And speaking of cracks in the armor,

00:14:12.169 --> 00:14:14.750
let's talk about the diversification phase. Because

00:14:14.750 --> 00:14:17.710
after the wild success of the lip kits, she tried

00:14:17.710 --> 00:14:21.090
to launch everything. This is a classic business

00:14:21.090 --> 00:14:23.519
race. It's called brand dilution. When you have

00:14:23.519 --> 00:14:26.159
a massive hit, the temptation is to slap that

00:14:26.159 --> 00:14:28.340
logo on every product category you can think

00:14:28.340 --> 00:14:30.539
of. And she definitely tried. We had Kylie Skin

00:14:30.539 --> 00:14:33.720
in 2019. Which did, okay, right. It had some

00:14:33.720 --> 00:14:36.259
initial controversy with the walnut scrub, which

00:14:36.259 --> 00:14:38.639
dermatologists panned. Oh, I remember that. People

00:14:38.639 --> 00:14:40.840
were saying it causes micro tears in your skin.

00:14:41.000 --> 00:14:43.179
Exactly. So it wasn't a runaway success like

00:14:43.179 --> 00:14:45.500
the cosmetics line, but it established a foothold.

00:14:45.799 --> 00:14:48.720
Then we had Kylie Baby in 2021. Which made a

00:14:48.720 --> 00:14:50.740
lot of sense from a branding perspective. She

00:14:50.740 --> 00:14:53.120
had pivoted to this motherhood persona, so a

00:14:53.120 --> 00:14:55.360
baby line felt like a natural extension. It did.

00:14:55.519 --> 00:15:00.019
But then we had Kylie Swim. Kylie Swim. September

00:15:00.019 --> 00:15:04.929
2021. This is widely considered her first catastrophic,

00:15:05.190 --> 00:15:07.909
undeniable business failure. The reviews were

00:15:07.909 --> 00:15:10.750
savage. I mean, truly savage. I remember watching

00:15:10.750 --> 00:15:13.789
TikToks of girls opening the packages and the

00:15:13.789 --> 00:15:15.809
fabric was basically sheer. You could see right

00:15:15.809 --> 00:15:19.039
through it. It was described as paper thin. The

00:15:19.039 --> 00:15:21.879
stitching was crooked and uneven. The cuts were

00:15:21.879 --> 00:15:24.740
bizarrely impractical. If you moved even slightly,

00:15:24.980 --> 00:15:27.399
you are at risk of being exposed. The consensus

00:15:27.399 --> 00:15:29.679
critique was that it was swimwear for Instagram

00:15:29.679 --> 00:15:32.899
photos, not for actual swimming. Which kind of

00:15:32.899 --> 00:15:35.059
sums up the whole aesthetic, doesn't it? It does,

00:15:35.320 --> 00:15:37.840
but it also showed the limits of her power. You

00:15:37.840 --> 00:15:39.960
can hype a product to your 300 million followers,

00:15:40.220 --> 00:15:42.980
but if the quality is visibly terrible, the backlash

00:15:42.980 --> 00:15:45.389
is instant and overwhelming. It showed that her

00:15:45.389 --> 00:15:47.970
fans weren't just mindless drones. They expected

00:15:47.970 --> 00:15:50.409
a certain level of value for their money. And

00:15:50.409 --> 00:15:53.070
Kylie Swim did not deliver, to put it mildly.

00:15:53.129 --> 00:15:54.529
And she didn't stop there with the launches.

00:15:54.570 --> 00:15:56.169
We have to mention the more recent ventures.

00:15:56.230 --> 00:15:59.629
In late 2024, she launched Kai. Her clothing

00:15:59.629 --> 00:16:02.330
line. And this was an interesting pivot because

00:16:02.330 --> 00:16:04.809
she seemed to be aiming higher. She collaborated

00:16:04.809 --> 00:16:07.830
with respected designers like Antonin Tron. Right.

00:16:07.909 --> 00:16:09.929
It wasn't just merch with her name on it. Exactly.

00:16:10.149 --> 00:16:12.129
It was an attempt to be taken more seriously

00:16:12.129 --> 00:16:14.870
in the high fashion world, moving from mall brand

00:16:14.870 --> 00:16:17.529
to designer. And then just last year, Sprinter.

00:16:18.289 --> 00:16:21.490
The canned cocktails? The vodka soda in a can,

00:16:21.669 --> 00:16:24.190
which again is just monetizing the lifestyle.

00:16:24.649 --> 00:16:27.009
Drink what Kylie drinks at her parties. It's

00:16:27.009 --> 00:16:30.049
a very low barrier to entry product with extremely

00:16:30.049 --> 00:16:32.950
high margins. One of the things that always fascinates

00:16:32.950 --> 00:16:35.450
me about our business strategy is the aggression

00:16:35.450 --> 00:16:38.259
regarding trademarks. She tries to own words,

00:16:38.440 --> 00:16:41.220
common words. The trademark machine is relentless.

00:16:41.460 --> 00:16:43.860
It's a core part of the business model. The rise

00:16:43.860 --> 00:16:46.200
and shine moment is the perfect example. It really

00:16:46.200 --> 00:16:50.100
is. So October 2019, a simple clip of her walking

00:16:50.100 --> 00:16:52.000
into Stormy's room and seeing rise and shine

00:16:52.000 --> 00:16:54.740
goes viral, becomes a huge meme. It was everywhere

00:16:54.740 --> 00:16:58.500
for like a week. And within days, her team files

00:16:58.500 --> 00:17:02.019
to trademark the phrase rise and shine for use

00:17:02.019 --> 00:17:04.720
on cosmetics and clothing. She even filed for

00:17:04.720 --> 00:17:07.500
a raise in Sheeny with the dragged out spelling

00:17:07.500 --> 00:17:11.259
to cover all her bases. It shows how reactive

00:17:11.259 --> 00:17:14.119
her business team is. I see a flicker of a meme

00:17:14.119 --> 00:17:16.660
and the immediate instinct is to try and legally

00:17:16.660 --> 00:17:19.240
own it and monetize it. But she doesn't always

00:17:19.240 --> 00:17:21.279
win these battles. We have to talk about the

00:17:21.279 --> 00:17:23.759
battle of the Kylies. Kylie Minogue versus Kylie

00:17:23.759 --> 00:17:27.170
Jenner. A true... Clash of the Titans. This is

00:17:27.170 --> 00:17:29.589
my favorite of her legal battles, I think. It's

00:17:29.589 --> 00:17:32.589
a great one. So in 2015, Jenner's team filed

00:17:32.589 --> 00:17:35.329
to trademark the name Kylie, just the first name,

00:17:35.450 --> 00:17:38.230
for advertising and endorsement services. A pretty

00:17:38.230 --> 00:17:40.609
bold move. Very gold. And Kylie Minogue's legal

00:17:40.609 --> 00:17:44.349
team was not having it. They were not. They filed

00:17:44.349 --> 00:17:47.250
a formal opposition. And the language they used

00:17:47.250 --> 00:17:49.809
in the filing was just brutal. They referred

00:17:49.809 --> 00:17:53.109
to Kylie Jenner as a secondary reality. television

00:17:53.109 --> 00:17:56.369
personality. Secondary? That is just devastatingly

00:17:56.369 --> 00:17:58.769
shady. And then in the same document, they described

00:17:58.769 --> 00:18:01.910
their client, Kylie Minogue, as an internationally

00:18:01.910 --> 00:18:04.549
acclaimed recording artist, humanitarian, and

00:18:04.549 --> 00:18:06.490
breast cancer activist. Drawing a very clear

00:18:06.490 --> 00:18:09.730
line in the sand. And Minogue won. In February

00:18:09.730 --> 00:18:13.450
2017, the U .S. Patent and Trademark Office rejected

00:18:13.450 --> 00:18:16.130
Jenner's claim. I love that. It's a reality check.

00:18:16.349 --> 00:18:18.630
You might be the most famous person on Instagram,

00:18:18.750 --> 00:18:22.039
but you do not own the name Kylie. And it also

00:18:22.039 --> 00:18:24.720
highlights this interesting friction between

00:18:24.720 --> 00:18:29.859
new fame, internet fame, and legacy fame, which

00:18:29.859 --> 00:18:32.519
is built over decades. It wasn't just trademarks,

00:18:32.519 --> 00:18:34.640
though. There were some really serious accusations

00:18:34.640 --> 00:18:37.660
of stealing ideas from other artists. Intellectual

00:18:37.660 --> 00:18:39.900
property disputes are incredibly common in the

00:18:39.900 --> 00:18:42.380
fashion and beauty industries. But Kylie seemed

00:18:42.380 --> 00:18:44.200
to have a lot of them in a short period. There

00:18:44.200 --> 00:18:47.920
was the Vlada Hagerty case in 2017. Right. Vlada

00:18:47.920 --> 00:18:50.380
was a makeup artist who was known for this very

00:18:50.380 --> 00:18:53.140
specific aesthetic of dripping gloss lips and

00:18:53.140 --> 00:18:55.759
hands painted with metallic colors. She posted

00:18:55.759 --> 00:18:57.779
a photo of gold -painted fingers and a dripping

00:18:57.779 --> 00:19:00.180
red lip. And a few weeks later, Kylie Cosmetics

00:19:00.180 --> 00:19:02.819
posted an image for a holiday campaign that looked

00:19:02.819 --> 00:19:04.819
almost identical. It was strikingly similar.

00:19:04.940 --> 00:19:07.079
The composition, the colors, everything. Flotta

00:19:07.079 --> 00:19:09.799
sued, and unlike most of these cases that just

00:19:09.799 --> 00:19:12.339
disappear, this one resulted in a public outcome.

00:19:12.579 --> 00:19:14.700
What happened? They reached an undisclosed settlement.

00:19:14.859 --> 00:19:17.099
But part of it was that Kylie actually had to

00:19:17.099 --> 00:19:20.200
credit Flotta on her social media. She posted

00:19:20.200 --> 00:19:23.339
the original image and tagged the artist. which

00:19:23.339 --> 00:19:25.440
is a rare admission that they essentially got

00:19:25.440 --> 00:19:27.539
caught listing the aesthetic. And then the Seed

00:19:27.539 --> 00:19:30.880
Beauty lawsuit. This one feels much more corporate

00:19:30.880 --> 00:19:33.940
and complex. This is the heavy stuff. This goes

00:19:33.940 --> 00:19:36.779
back to the Cody deal. So Seed Beauty was the

00:19:36.779 --> 00:19:38.839
manufacturer, the company that actually made

00:19:38.839 --> 00:19:41.099
the lip kits and fulfilled the orders. The engine

00:19:41.099 --> 00:19:44.019
behind the whole operation. Exactly. When Kylie

00:19:44.019 --> 00:19:47.839
sold to Cody, Seed sued them both. They alleged

00:19:47.839 --> 00:19:50.740
that the entire deal was a subterfuge. That was

00:19:50.740 --> 00:19:53.480
the word they used. A scheme to steal their trade

00:19:53.480 --> 00:19:55.859
secrets and hand them over to Cody, which is

00:19:55.859 --> 00:19:57.599
one of the biggest beauty companies in the world.

00:19:57.779 --> 00:20:00.400
So Seed was essentially saying, we built your

00:20:00.400 --> 00:20:02.819
entire product line and now you're selling our

00:20:02.819 --> 00:20:05.900
secret recipes to our biggest competitor. Precisely.

00:20:06.019 --> 00:20:09.059
The lawsuit revealed just how much Kylie's business

00:20:09.059 --> 00:20:11.980
was really a shell built on top of Seed's proprietary

00:20:11.980 --> 00:20:14.859
technology and processes. We also have to touch

00:20:14.859 --> 00:20:17.119
on the supply chain issues, the global brands

00:20:17.119 --> 00:20:20.230
group controversy back in 2020. This was a significant

00:20:20.230 --> 00:20:22.509
reputational risk, and it happened right in the

00:20:22.509 --> 00:20:24.789
middle of the pandemic. Reports surfaced that

00:20:24.789 --> 00:20:27.430
Global Brands Group, a company that listed the

00:20:27.430 --> 00:20:29.970
Kendall plus Kylie brand on its website as a

00:20:29.970 --> 00:20:32.630
partner, was failing to pay its garment workers

00:20:32.630 --> 00:20:34.769
in Bangladesh for orders that were canceled.

00:20:34.970 --> 00:20:37.829
This was part of the big hashtag pay up campaign

00:20:37.829 --> 00:20:39.890
on social media. Right. And the Jenner response

00:20:39.890 --> 00:20:44.369
was very corporate. Yeah. Very legal. They issued

00:20:44.369 --> 00:20:46.109
a statement saying their brand was technically

00:20:46.109 --> 00:20:48.759
owned by a separate entity. a numbered company,

00:20:48.960 --> 00:20:53.680
3072541 Canada Inc. So creating distance. And

00:20:53.680 --> 00:20:55.819
they said they had no current relationship with

00:20:55.819 --> 00:20:58.059
Global Brands Group, even though they had worked

00:20:58.059 --> 00:21:00.539
with them in sales in the past. It was an attempt

00:21:00.539 --> 00:21:02.400
to distance themselves from the manufacturing

00:21:02.400 --> 00:21:05.049
liability. That's not us anymore. Essentially.

00:21:05.589 --> 00:21:08.509
It highlights the complex and often opaque web

00:21:08.509 --> 00:21:10.670
of licensing deals that make up these celebrity

00:21:10.670 --> 00:21:13.509
brands. It's often incredibly hard to tell who

00:21:13.509 --> 00:21:15.450
is actually responsible for the worker on the

00:21:15.450 --> 00:21:18.410
factory floor. It really is. So, okay, we've

00:21:18.410 --> 00:21:20.289
covered the business, the scandals, the legal

00:21:20.289 --> 00:21:23.170
battles, but we can't do a deep dive on Kylie

00:21:23.170 --> 00:21:25.210
without talking about her personal life. You

00:21:25.210 --> 00:21:27.349
can't. Because in this ecosystem, the personal

00:21:27.349 --> 00:21:29.670
life is the business strategy. They are one and

00:21:29.670 --> 00:21:32.329
the same. We call them content pillars in the

00:21:32.329 --> 00:21:35.670
branding world. And if you track her major relationships,

00:21:35.970 --> 00:21:38.269
they align almost perfectly with her brand evolution

00:21:38.269 --> 00:21:41.150
and her attempts to expand into new demographics.

00:21:41.470 --> 00:21:43.910
Let's start with Tyga. The Tyga era, roughly

00:21:43.910 --> 00:21:47.650
2014 to 2017. This was controversial from the

00:21:47.650 --> 00:21:49.589
start because of the age gap. Right. She was

00:21:49.589 --> 00:21:52.490
17 when they met and he was in his mid -20s.

00:21:52.630 --> 00:21:55.109
They didn't go official until she was 18. Exactly.

00:21:55.660 --> 00:21:58.539
But from a brand perspective, Tyga served a very

00:21:58.539 --> 00:22:01.400
specific purpose. He was her entry point into

00:22:01.400 --> 00:22:03.500
the hip -hop world. She was in his music videos,

00:22:03.759 --> 00:22:07.259
stimulated, doped up. It shifted her image away

00:22:07.259 --> 00:22:09.599
from the little sister on a family reality show

00:22:09.599 --> 00:22:12.579
to something more like a video vixen. It gave

00:22:12.579 --> 00:22:14.920
her an edge that appealed to a cooler, younger,

00:22:15.039 --> 00:22:18.720
more urban demographic that KUWTK wasn't reaching.

00:22:18.859 --> 00:22:21.740
And then after Tyga came Travis Scott. A major

00:22:21.740 --> 00:22:24.970
upgrade in terms of cultural cachet. They met

00:22:24.970 --> 00:22:28.730
at Coachella in 2017. This solidified her status

00:22:28.730 --> 00:22:31.750
in the A -list music world. But the defining

00:22:31.750 --> 00:22:33.710
moment of that relationship wasn't the relationship

00:22:33.710 --> 00:22:37.140
itself, it was the pregnancy. The secret pregnancy.

00:22:37.579 --> 00:22:40.160
I still think this is one of the most impressive

00:22:40.160 --> 00:22:43.119
feats of PR in the last decade. I mean, for a

00:22:43.119 --> 00:22:45.220
member of that family to disappear completely.

00:22:45.619 --> 00:22:49.200
It was a master class in strategic silence. In

00:22:49.200 --> 00:22:51.440
an attention economy, when you are constantly

00:22:51.440 --> 00:22:53.960
overexposed, the most valuable thing you can

00:22:53.960 --> 00:22:56.160
offer your audience is mystery. She created a

00:22:56.160 --> 00:22:58.789
vacuum. A total vacuum. Everyone wanted to know

00:22:58.789 --> 00:23:01.630
where she was. Speculation was rampant. It drove

00:23:01.630 --> 00:23:03.410
engagement through the roof without her having

00:23:03.410 --> 00:23:05.329
to post a single thing. And when she finally

00:23:05.329 --> 00:23:08.349
dropped that video to her daughter in February

00:23:08.349 --> 00:23:12.069
2018, after Stormi was born. It broke the internet

00:23:12.069 --> 00:23:14.769
all over again. And notice the rebrand that happened

00:23:14.769 --> 00:23:16.630
in that moment. She went from the wild child

00:23:16.630 --> 00:23:18.309
with the lip fillers and the rapper boyfriend

00:23:18.309 --> 00:23:21.890
to Stormi's mom. It softened her image instantly.

00:23:22.230 --> 00:23:24.089
And of course, it laid the commercial groundwork

00:23:24.089 --> 00:23:26.170
for Kylie Baby, which would launch a few years

00:23:26.170 --> 00:23:28.470
later. Always selling. It's always about the

00:23:28.470 --> 00:23:31.329
next product. They had a second child, Air, in

00:23:31.329 --> 00:23:33.930
2022, but their relationship with Travis was

00:23:33.930 --> 00:23:37.630
famously on and off. Very much so. And that final

00:23:37.630 --> 00:23:41.630
off status in early 2023 opened the door for

00:23:41.630 --> 00:23:44.559
the current era. the timothy chalamet era i remember

00:23:44.559 --> 00:23:47.400
when the rumors started in april 2023 i thought

00:23:47.400 --> 00:23:48.920
it was a joke i thought it was a fan fiction

00:23:48.920 --> 00:23:51.819
headline timothy chalamet the indie darling the

00:23:51.819 --> 00:23:55.119
dune guy and kylie jenner on paper it seemed

00:23:55.119 --> 00:23:58.059
like a complete mismatch of brands he represents

00:23:58.059 --> 00:24:01.099
high art and prestige cinema She represents commercial

00:24:01.099 --> 00:24:03.599
reality TV and influencer culture. Two different

00:24:03.599 --> 00:24:05.640
universes. But when they stepped out publicly,

00:24:05.839 --> 00:24:08.640
especially at the Golden Globes in 2024, it sent

00:24:08.640 --> 00:24:11.180
a very clear signal. What was the signal? The

00:24:11.180 --> 00:24:14.680
signal was, I am not just an influencer. I am

00:24:14.680 --> 00:24:17.519
Hollywood. Dating Timothee Chalamet creates a

00:24:17.519 --> 00:24:20.630
proximity to prestige that money can't buy. It

00:24:20.630 --> 00:24:22.950
legitimizes her in circles that previously might

00:24:22.950 --> 00:24:25.029
have looked down on the Kardashians. It's a strategic

00:24:25.029 --> 00:24:27.869
social move that has business implications. Absolutely.

00:24:27.970 --> 00:24:29.750
Which brings us perfectly to where we are right

00:24:29.750 --> 00:24:33.450
now in 2026, because she is making this massive

00:24:33.450 --> 00:24:36.680
career change. She is acting. She is. She has

00:24:36.680 --> 00:24:39.079
a starring role in the film The Moment, which

00:24:39.079 --> 00:24:41.259
is set to come out this year. And it's not like

00:24:41.259 --> 00:24:43.559
a throwaway comedy or a cameo. It's produced

00:24:43.559 --> 00:24:47.880
by Charlie XCX and Studio 365. It has this indie

00:24:47.880 --> 00:24:50.839
cool girl vibe to it. This is a very significant

00:24:50.839 --> 00:24:53.539
move. Yeah. You know, Kim Kardashian tried to

00:24:53.539 --> 00:24:56.140
act. And while she had some moments in Tyler

00:24:56.140 --> 00:24:59.079
Perry movies, she never fully crossed over into

00:24:59.079 --> 00:25:01.970
being considered a thespian. Right. Kylie is

00:25:01.970 --> 00:25:03.470
trying to make that jump. She wants to be taken

00:25:03.470 --> 00:25:05.950
seriously as a talent, not just a personality.

00:25:06.250 --> 00:25:08.170
Do you think she can pull it off? Can she actually

00:25:08.170 --> 00:25:10.630
act? That is the billion -dollar question, isn't

00:25:10.630 --> 00:25:12.569
it? She has spent her entire life performing

00:25:12.569 --> 00:25:14.970
for a camera, so she's comfortable there. But

00:25:14.970 --> 00:25:17.309
reality TV performance is very, very different

00:25:17.309 --> 00:25:19.450
from scripted character work. A completely different

00:25:19.450 --> 00:25:22.369
skill set. If she succeeds, if she gets good

00:25:22.369 --> 00:25:24.869
reviews, she extends her career by decades. If

00:25:24.869 --> 00:25:27.529
she fails, if she's panned, it just reinforces

00:25:27.529 --> 00:25:29.970
the trashy reality star stereotype she's been

00:25:29.970 --> 00:25:32.380
trying to escape. She's also still breaking records

00:25:32.380 --> 00:25:34.559
on social media, which is kind of mind -boggling.

00:25:34.619 --> 00:25:37.859
She was the first woman to hit 300 million followers

00:25:37.859 --> 00:25:40.720
on Instagram back in 2022. And just holding that

00:25:40.720 --> 00:25:43.380
level of attention for nearly 20 years is unprecedented.

00:25:44.079 --> 00:25:46.480
Usually, internet fame has a half -life of about

00:25:46.480 --> 00:25:49.220
18 months. She has stayed relevant through the

00:25:49.220 --> 00:25:53.460
age of Vine, Snapchat, Instagram, TikTok. She

00:25:53.460 --> 00:25:55.519
adapts to the medium. Even with the music video

00:25:55.519 --> 00:25:58.579
cameos. I mean, she was in WAP with Cardi B and

00:25:58.579 --> 00:26:00.799
Megan Thee Stallion. Which sparked a petition

00:26:00.799 --> 00:26:03.019
with hundreds of thousands of signatures to have

00:26:03.019 --> 00:26:05.410
her removed from the video. People were furious.

00:26:05.769 --> 00:26:09.170
But again, controversy creates cash. It kept

00:26:09.170 --> 00:26:10.990
her name in the conversation. And more recently,

00:26:11.049 --> 00:26:13.410
appearing in A .G. Cook's video for Residue.

00:26:13.470 --> 00:26:16.069
A much more niche calculated move. Very. She

00:26:16.069 --> 00:26:18.430
is aligning herself with the hyper pop avant

00:26:18.430 --> 00:26:21.450
-garde crowd. It's a very specific rebranding

00:26:21.450 --> 00:26:24.109
strategy to appear culturally relevant to the

00:26:24.109 --> 00:26:26.650
Gen Z and Gen Alpha audience that might not watch

00:26:26.650 --> 00:26:29.460
her family show. So. Okay, if we step back and

00:26:29.460 --> 00:26:31.839
look at the whole picture, from the lip kits

00:26:31.839 --> 00:26:35.240
to the Forbes scandal to this acting pivot, what

00:26:35.240 --> 00:26:37.180
is the big takeaway? What's the lesson here?

00:26:37.380 --> 00:26:40.359
For me, it's that Kylie Jenner is a mirror for

00:26:40.359 --> 00:26:43.539
the modern economy. She proved that you can monetize

00:26:43.539 --> 00:26:46.279
anything, your face, your relationships, your

00:26:46.279 --> 00:26:48.759
children, even your own insecurities, if you

00:26:48.759 --> 00:26:51.619
package it right. I agree. She represents the

00:26:51.619 --> 00:26:54.759
attention as currency. thesis. She proved that

00:26:54.759 --> 00:26:57.380
in the 21st century, attention is more valuable

00:26:57.380 --> 00:27:00.180
than oil or gold. If you have the eyeballs, you

00:27:00.180 --> 00:27:03.880
can sell the product, but there's a but. The

00:27:03.880 --> 00:27:06.339
Forbes retraction and the Kylie Swim flop show

00:27:06.339 --> 00:27:08.259
that there is a limit. Yeah. You can bluff your

00:27:08.259 --> 00:27:10.500
way to a title and you can hype a bad swimsuit,

00:27:10.519 --> 00:27:12.579
but eventually the truth comes out. It comes

00:27:12.579 --> 00:27:14.940
out in the tax returns or the customer reviews.

00:27:15.019 --> 00:27:17.799
Exactly. You cannot fake quality or truth forever.

00:27:18.079 --> 00:27:20.460
Gravity always wins. And that's what makes this

00:27:20.460 --> 00:27:23.720
2026 acting pivot so interesting because you

00:27:23.720 --> 00:27:25.660
can't really fake acting, not in a serious film.

00:27:25.759 --> 00:27:28.160
The camera catches everything. It does. She is

00:27:28.160 --> 00:27:30.299
moving from an arena where she controls the edit,

00:27:30.339 --> 00:27:33.079
her Instagram feed, her reality show to an arena.

00:27:38.299 --> 00:27:41.380
So here is a provocative thought to leave you

00:27:41.380 --> 00:27:44.500
with as we wrap up. Kylie is clearly diversifying.

00:27:44.599 --> 00:27:47.059
She's moving away from just being Kylie the face.

00:27:47.279 --> 00:27:49.720
She's acting. She's doing clothing with Kai that

00:27:49.720 --> 00:27:53.279
focuses on design. She's doing Sprinter. Is she

00:27:53.279 --> 00:27:56.220
acknowledging? Maybe subconsciously that the

00:27:56.220 --> 00:27:59.160
influencer economy has a ceiling, that a personal

00:27:59.160 --> 00:28:01.720
brand built entirely on your own face and life

00:28:01.720 --> 00:28:04.380
has a shelf life. I think she is. I think she

00:28:04.380 --> 00:28:06.880
knows that King Kylie cannot reign forever. A

00:28:06.880 --> 00:28:09.500
meme can only last so long. She is trying to

00:28:09.500 --> 00:28:11.880
build a legacy that exists outside of just being

00:28:11.880 --> 00:28:14.559
the youngest sister. The real question is, will

00:28:14.559 --> 00:28:17.539
the audience let her evolve? Or is she trapped

00:28:17.539 --> 00:28:20.460
in the caricature she so brilliantly built? Something

00:28:20.460 --> 00:28:22.200
to think about. Thanks for diving in with us

00:28:22.200 --> 00:28:23.900
on this one. Always a pleasure. We'll catch you

00:28:23.900 --> 00:28:24.759
on the next deep dive.
