Welcome back to the Deep Dive. It is Monday,
February 2nd, 2026. And we have a big one today.
We really do. We are opening up a file that honestly,
it serves as the ultimate Rorschach test for
how you view modern capitalism. That's a great
way to put it. We're looking at a figure who
has been in the public eye for nearly two decades
now. Someone who essentially rewrote the playbook
on monetization, influence and the very concept
of reality. We are talking, of course, about
Kylie Jenner. We are. And, you know, it is a
fascinating time to be having this conversation.
Sitting here in early 2026, Kylie is 28 years
old. Right. And she is currently navigating what
is, I think, arguably the most dangerous pivot
of her career. The acting move. The acting move.
She's moved away from the King Kylie era of pure
influencer marketing. Yeah. And is attempting
to break into serious acting with her role in
the moment. A huge gamble. A massive one. Yeah.
But understand, if this gamble is going to pay
off, we have to go back. We have to understand
the machine that got her here in the first place.
Exactly. I think a lot of people see the Instagram
grid, the Met Gala looks, you know, the headlines,
and they just see celebrity. But when you actually
dig into the stack of reports we have here, and
we have a lot, the SEC filings from the Cordy
deal, the trademark court transcripts, the supply
chain audits, you realize this isn't just fluff.
This is a case study in really aggressive business
strategy. It really is. And our mission today
is to unpack that strategy. We're going to look
at how the youngest sibling, who was effectively
a background character in the early days of Keeping
Up with the Kardashians. She really was just
sort of there. Leveraged a specific physical
insecurity into a billion dollar conversation.
And as I said, conversation, not necessarily
billion dollar bank account. Yes. Because we
are definitely going to get into the weeds of
that Forbes scandal. The web of lies. We are
absolutely going there. I can't wait. But before
we get to the billions and the scandals, let's
unpack the origin story. You have to. Because
to understand Kylie in 2026, you have to remember
who she was in, like, 2010. You have to go back
to what I call the bundled era. The bundled era.
That is such a good way to put it. Explain that.
Well, think about it. She was born in 1997. The
show premieres in 2007. She's nine years old.
A child. A literal child. So for the first five
or six years of her fame, she didn't have a solo
identity in the marketplace. She was a package
deal. It was always Kendall and Kylie. Always.
I was looking through the notes on their early
ventures and it is a trip down memory lane. I
mean, they were throwing everything at the wall.
Everything. You had the clothing line with PacSun
in 2013, the Kendall and Kylie collection. Which
for a mall brand was actually pretty successful.
It was. Then you had the jewelry line with Glam
House. They even had that ghost written sci -fi
novel. Rebels. City of Indra. A classic of the
genre. Yes. I completely forgot about this. It's
such a fascinating artifact of celebrity branding.
It was released in 2014. And you have to remember
the context. Dystopia was huge because of the
Hunger Games. Oh, it was everything. So, of course,
they tried to capitalize on that trend. But the
critical reception was, let's just call it brutal.
Brutal is kind. I think it sold something like
13 ,000 copies in the first four months. Which,
for a celebrity book of that level, is a flop.
And the controversy wasn't just that the book
was, you know, not very good. It was the authorship.
All right. That was the real issue. It was marketed
very heavily as a novel by Kendall and Kylie
Jenner. Their names were huge on the cover. Right.
But then it came out that a writer named Maya
Sloan was the actual author, the ghostwriter.
Now, ghostwriting is totally standard in the
industry. That's not the issue. Not at all. But
usually, the celebrity provides the meat of the
story, the characters, the plot points. In this
case, the Jenner camp's defense was that the
girls had, and this is a direct quote, numerous
Skype and FaceTime calls with the writer. Numerous
Skype calls. That is a very, very low bar for
putting your name on the cover of a novel. It
is, but it highlights the strategy of that whole
era, brand slapping. Explain that. The idea was
that the name Jenner was the value add, regardless
of the product quality. The name itself was the
asset. So it didn't matter if it was nail polish
or a book. Exactly. Whether it was OPI nail polish
or a sci -fi book, the product was secondary
to the label. But the problem for Kylie was she
didn't have her own label yet. She was just Kendall's
sister. Kendall's little sister. Which brings
us to the pivot point. I mean, this is the moment
that changed the trajectory of the entire family
business, really. It did. We're talking 2014
and 2015. We're talking about the lips. This
is the aha moment. And it's so fascinating because
it's rooted in a very human, very relatable insecurity.
I remember this so vividly. Her face started
changing on Instagram. Her lips got significantly
bigger and it happened like overnight. It was
very sudden. And the media obsession shifted
from what is she wearing to what did she do to
her face? That was the only question anyone was
asking. And for a long, long time, the strategy
was denial. Complete and total denial. She claimed
it was just lip liner. The overlining trick?
She said she was overlining her lips to create
an optical illusion. She gave tutorials on it.
Which, I don't know if it was inadvertent or
not, but it triggered the Kylie Jenner challenge.
Oh, it wasn't inadvertent, the effect at least.
And that challenge was a sociologically fascinating,
if horrifying, Phenomenon. Horrifying is the
word. You had thousands of teenagers, mostly
young girls, suctioning their lips into shot
glasses or water bottles to induce swelling,
trying to mimic that look. People were bruising
themselves, bursting blood vessels. It was actually
dangerous. The photos were all over the Internet.
It was incredibly dangerous. But from a business
perspective, what did that tell her team? It's
a proof of concept. It's hard data. It proved
that her influence was so potent that people
were willing to physically harm themselves to
emulate her. That is a level of engagement that
traditional advertising simply cannot buy. No
amount of money gets you that. It showed that
the market demand for being Kylie was astronomical.
So after months of denial, she finally confesses
in May 2015 on the show. She admits to the fillers.
She does. And here is where the genius kicks
in. Most publicists in that situation would say,
OK. apologize for the lie, go quiet, let the
news cycle turn. Disappear for a while. Right.
Let people forget. Kylie's team, led by Kris
Jenner, did the opposite. They operationalized
the scandal. They monetized the insecurity. Exactly.
Three months after the confession, three months,
in August 2015, she announces the Kylie lip kit.
It's so fast. She essentially said, you've been
talking about my lips for a year. Fine. Here's
the exact product to get them. She took ownership
of the narrative. It turned the biggest tabloid
negative into a product feature. It's brilliant
marketing. And the execution of the launch was
flawless. They used what we call the DRAP model,
which was, as you said, borrowed from streetwear
brands like Supreme. Right. They launched in
November 2015 with an intentionally limited inventory
to 15 ,000 kits. And they sold out in, what was
it, under a minute. Seconds. Literally seconds.
And because they sold out so fast, the narrative
wasn't Kylie sells makeup. The narrative was
Kylie breaks the Internet. The scarcity was the
story. Precisely. That scarcity created panic
buying for the next drop and the drop after that.
By February 2016, she rebrands from the Simple
Lip Kit to the full Kylie Cosmetics and Scales
production, up to 500 ,000 kits. That is a massive
scale -up in just a few months. It's an incredible
jump. I want to talk about the cost structure
here, because from the outside, the margins on
this must have been insane. They were incredible.
And this is key to understanding her wealth accumulation.
This was a very lean, very asset light business
model. What do you mean by that? She didn't build
a factory. She didn't hire a massive logistics
team or an R &D department. Yeah. She's a white
label manufacturer. So a company that already
makes makeup for other people. Exactly. A company
called Spatz Laboratories. And she used a company
called Seed Beauty for the product development
and fulfillment. She basically outsourced the
entire back end of the business. So her overhead
was tiny. Minimal. Her main cost was the cost
of goods sold and her marketing cost. Effectively
zero. She didn't buy TV ads. She didn't buy billboards.
She just posted on Snapchat and Instagram to
her tens of millions of followers. The glosses
video. That's a perfect example. I remember that.
It was like a little movie. Directed by a major
music video director, Colin Tilly. It wasn't
a commercial. It was a three -minute action movie
where she's driving a Rolls Royce in the desert.
There's a heist. It was content. Right. It blurred
the line between entertainment and advertising
in a way that was at the time really revolutionary
for a cosmetics brand. So she has low overhead,
zero marketing costs, and a product that sells
out instantly. She is, for all intents and purposes,
printing money. Which leads us directly to the
magazine cover that started a war. Here we go.
Part two. The billionaire wars. I feel like this
is where the story gets really technical and
really messy. It does, because we're moving from
social media hype into the world of audited financials
and SEC regulations. It's a whole different beast.
It is. So fast forward to August 2018. Kylie
is on the cover of Forbes. The headline estimates
her net worth at $900 million. And she's only
20 years old at this point. It's an unbelievable
number. And then by March 2019. Forbes follows
up and officially declares her the world's youngest
self -made billionaire at age 21. She beat Mark
Zuckerberg. That was the headline everywhere.
Younger than the founder of Facebook. On paper,
yes. Yeah. And this announcement sparked two
massive simultaneous debates. The first was the
cultural debate over the term self -made. Oh,
people were furious. I remember the tweets. I
remember the think pieces. How can you be self
-made when you're born a Kardashian? It's a valid
semantic argument. You know, critics argue that
she was born on third base and thought she hit
a triple. Right. She had inherited fame, capital
from her family, a reality show platform, and
a safety net that 99 .9 % of entrepreneurs just
do not have. But her family and even people like
Paris Hilton came out to defend her. They made
the argument that she didn't inherit the business.
She built the business using the platform she
was given. Which is true. But that platform is
a priceless asset. You can't separate the two.
However, that entire cultural debate became secondary
to the financial reality. It did. Because in
May 2020, Forbes released a bombshell retraction.
An entire article dedicated to walking it back.
The headline was incredible. Inside Kylie Jenner's
web of lies. You can't get much more direct than
that. They didn't just walk back the number.
They accused the Jenner camp of actively participating
in financial engineering and deception. Okay,
walk us through this. This is where it gets complicated.
What exactly do Forbes accuse her of? So the
primary source for that billionaire valuation,
going back to the 2018 article, was tax returns
and revenue figures provided directly by Kylie's
team, specifically her mother and manager, Kris
Jenner. Okay, so they were handing over documents.
They were. And these documents claimed the business
was generating somewhere between $360 million
and $400 million a year in revenue. Massive numbers.
And Forbes, a reputable financial magazine, believed
them. They did. They published the numbers. The
problem arose when Kylie sold a majority stake
in her company. In November 2019, she sold a
51 % stake in Kylie Cosmetics to the beauty conglomerate
Coty. And she sold it for $600 million. A massive
exit. $600 million in cash. On the surface, that
seems to validate the billion -dollar valuation,
right? A $600 million sale for 51 % values the
company at roughly $1 .2 billion. Exactly. So
what was the issue? Here's the catch. Cody is
a publicly traded company. They are regulated
by the SEC. They cannot lie to their shareholders
about the financials of a company they just bought.
It's illegal. So when Cody released their shareholder
reports and their investor presentations about
the acquisition, the real verified audited numbers
for Kylie Cosmetics came out. And what were the
real numbers? Kylie Cosmetics wasn't doing $360
million a year. In 2018, for instance, it did
about $125 million. Wow. That is that is a significant
discrepancy. Less than half of what they were
claiming. It's not even the same ballpark. So
the implication from Forbes was that for years,
the Jenner team had been inflating the numbers
they were giving to the media. That was the direct
accusation that they had fabricated revenue figures
and forged tax documents to create the perception
of a billion dollar brand. So the question is,
why do that? She was already incredibly rich.
Why risk fraud accusations just for a title?
Because in the influencer economy. Perception
is reality. The title billionaire is a marketing
tool. It's the ultimate validation for the brand.
It makes the product seem more desirable. It
does. It signals to the world this is the winner.
It creates a mythology around the founder that,
in turn, drives sales. Being a billionaire wasn't
just about her bank account. It was about the
brand's story. So Forbes officially strips the
title. How did Kylie respond to this Web of Lies
article? She went straight to Twitter, now X,
of course. Yeah. She posted a series of tweets
denying that she'd ever asked for the title and
denying that she'd ever lied. What was the quote?
She wrote, I've never asked for any title or
tried to lie my way there ever, period. But she
didn't dispute the numbers from the Cotty deal?
She couldn't. They were in public filings. So
she sort of sidestepped the core accusation.
But at the end of the day, she kept the $600
million from Cotty. And frankly, even after the
retraction. Forbes re -estimated her net worth
at around $700 million. So while she wasn't a
billionaire, she was still snaggeringly successful.
But the web of lies story, it cracked the armor.
It showed that the machine wasn't as invincible
as it looked. And speaking of cracks in the armor,
let's talk about the diversification phase. Because
after the wild success of the lip kits, she tried
to launch everything. This is a classic business
race. It's called brand dilution. When you have
a massive hit, the temptation is to slap that
logo on every product category you can think
of. And she definitely tried. We had Kylie Skin
in 2019. Which did, okay, right. It had some
initial controversy with the walnut scrub, which
dermatologists panned. Oh, I remember that. People
were saying it causes micro tears in your skin.
Exactly. So it wasn't a runaway success like
the cosmetics line, but it established a foothold.
Then we had Kylie Baby in 2021. Which made a
lot of sense from a branding perspective. She
had pivoted to this motherhood persona, so a
baby line felt like a natural extension. It did.
But then we had Kylie Swim. Kylie Swim. September
2021. This is widely considered her first catastrophic,
undeniable business failure. The reviews were
savage. I mean, truly savage. I remember watching
TikToks of girls opening the packages and the
fabric was basically sheer. You could see right
through it. It was described as paper thin. The
stitching was crooked and uneven. The cuts were
bizarrely impractical. If you moved even slightly,
you are at risk of being exposed. The consensus
critique was that it was swimwear for Instagram
photos, not for actual swimming. Which kind of
sums up the whole aesthetic, doesn't it? It does,
but it also showed the limits of her power. You
can hype a product to your 300 million followers,
but if the quality is visibly terrible, the backlash
is instant and overwhelming. It showed that her
fans weren't just mindless drones. They expected
a certain level of value for their money. And
Kylie Swim did not deliver, to put it mildly.
And she didn't stop there with the launches.
We have to mention the more recent ventures.
In late 2024, she launched Kai. Her clothing
line. And this was an interesting pivot because
she seemed to be aiming higher. She collaborated
with respected designers like Antonin Tron. Right.
It wasn't just merch with her name on it. Exactly.
It was an attempt to be taken more seriously
in the high fashion world, moving from mall brand
to designer. And then just last year, Sprinter.
The canned cocktails? The vodka soda in a can,
which again is just monetizing the lifestyle.
Drink what Kylie drinks at her parties. It's
a very low barrier to entry product with extremely
high margins. One of the things that always fascinates
me about our business strategy is the aggression
regarding trademarks. She tries to own words,
common words. The trademark machine is relentless.
It's a core part of the business model. The rise
and shine moment is the perfect example. It really
is. So October 2019, a simple clip of her walking
into Stormy's room and seeing rise and shine
goes viral, becomes a huge meme. It was everywhere
for like a week. And within days, her team files
to trademark the phrase rise and shine for use
on cosmetics and clothing. She even filed for
a raise in Sheeny with the dragged out spelling
to cover all her bases. It shows how reactive
her business team is. I see a flicker of a meme
and the immediate instinct is to try and legally
own it and monetize it. But she doesn't always
win these battles. We have to talk about the
battle of the Kylies. Kylie Minogue versus Kylie
Jenner. A true... Clash of the Titans. This is
my favorite of her legal battles, I think. It's
a great one. So in 2015, Jenner's team filed
to trademark the name Kylie, just the first name,
for advertising and endorsement services. A pretty
bold move. Very gold. And Kylie Minogue's legal
team was not having it. They were not. They filed
a formal opposition. And the language they used
in the filing was just brutal. They referred
to Kylie Jenner as a secondary reality. television
personality. Secondary? That is just devastatingly
shady. And then in the same document, they described
their client, Kylie Minogue, as an internationally
acclaimed recording artist, humanitarian, and
breast cancer activist. Drawing a very clear
line in the sand. And Minogue won. In February
2017, the U .S. Patent and Trademark Office rejected
Jenner's claim. I love that. It's a reality check.
You might be the most famous person on Instagram,
but you do not own the name Kylie. And it also
highlights this interesting friction between
new fame, internet fame, and legacy fame, which
is built over decades. It wasn't just trademarks,
though. There were some really serious accusations
of stealing ideas from other artists. Intellectual
property disputes are incredibly common in the
fashion and beauty industries. But Kylie seemed
to have a lot of them in a short period. There
was the Vlada Hagerty case in 2017. Right. Vlada
was a makeup artist who was known for this very
specific aesthetic of dripping gloss lips and
hands painted with metallic colors. She posted
a photo of gold -painted fingers and a dripping
red lip. And a few weeks later, Kylie Cosmetics
posted an image for a holiday campaign that looked
almost identical. It was strikingly similar.
The composition, the colors, everything. Flotta
sued, and unlike most of these cases that just
disappear, this one resulted in a public outcome.
What happened? They reached an undisclosed settlement.
But part of it was that Kylie actually had to
credit Flotta on her social media. She posted
the original image and tagged the artist. which
is a rare admission that they essentially got
caught listing the aesthetic. And then the Seed
Beauty lawsuit. This one feels much more corporate
and complex. This is the heavy stuff. This goes
back to the Cody deal. So Seed Beauty was the
manufacturer, the company that actually made
the lip kits and fulfilled the orders. The engine
behind the whole operation. Exactly. When Kylie
sold to Cody, Seed sued them both. They alleged
that the entire deal was a subterfuge. That was
the word they used. A scheme to steal their trade
secrets and hand them over to Cody, which is
one of the biggest beauty companies in the world.
So Seed was essentially saying, we built your
entire product line and now you're selling our
secret recipes to our biggest competitor. Precisely.
The lawsuit revealed just how much Kylie's business
was really a shell built on top of Seed's proprietary
technology and processes. We also have to touch
on the supply chain issues, the global brands
group controversy back in 2020. This was a significant
reputational risk, and it happened right in the
middle of the pandemic. Reports surfaced that
Global Brands Group, a company that listed the
Kendall plus Kylie brand on its website as a
partner, was failing to pay its garment workers
in Bangladesh for orders that were canceled.
This was part of the big hashtag pay up campaign
on social media. Right. And the Jenner response
was very corporate. Yeah. Very legal. They issued
a statement saying their brand was technically
owned by a separate entity. a numbered company,
3072541 Canada Inc. So creating distance. And
they said they had no current relationship with
Global Brands Group, even though they had worked
with them in sales in the past. It was an attempt
to distance themselves from the manufacturing
liability. That's not us anymore. Essentially.
It highlights the complex and often opaque web
of licensing deals that make up these celebrity
brands. It's often incredibly hard to tell who
is actually responsible for the worker on the
factory floor. It really is. So, okay, we've
covered the business, the scandals, the legal
battles, but we can't do a deep dive on Kylie
without talking about her personal life. You
can't. Because in this ecosystem, the personal
life is the business strategy. They are one and
the same. We call them content pillars in the
branding world. And if you track her major relationships,
they align almost perfectly with her brand evolution
and her attempts to expand into new demographics.
Let's start with Tyga. The Tyga era, roughly
2014 to 2017. This was controversial from the
start because of the age gap. Right. She was
17 when they met and he was in his mid -20s.
They didn't go official until she was 18. Exactly.
But from a brand perspective, Tyga served a very
specific purpose. He was her entry point into
the hip -hop world. She was in his music videos,
stimulated, doped up. It shifted her image away
from the little sister on a family reality show
to something more like a video vixen. It gave
her an edge that appealed to a cooler, younger,
more urban demographic that KUWTK wasn't reaching.
And then after Tyga came Travis Scott. A major
upgrade in terms of cultural cachet. They met
at Coachella in 2017. This solidified her status
in the A -list music world. But the defining
moment of that relationship wasn't the relationship
itself, it was the pregnancy. The secret pregnancy.
I still think this is one of the most impressive
feats of PR in the last decade. I mean, for a
member of that family to disappear completely.
It was a master class in strategic silence. In
an attention economy, when you are constantly
overexposed, the most valuable thing you can
offer your audience is mystery. She created a
vacuum. A total vacuum. Everyone wanted to know
where she was. Speculation was rampant. It drove
engagement through the roof without her having
to post a single thing. And when she finally
dropped that video to her daughter in February
2018, after Stormi was born. It broke the internet
all over again. And notice the rebrand that happened
in that moment. She went from the wild child
with the lip fillers and the rapper boyfriend
to Stormi's mom. It softened her image instantly.
And of course, it laid the commercial groundwork
for Kylie Baby, which would launch a few years
later. Always selling. It's always about the
next product. They had a second child, Air, in
2022, but their relationship with Travis was
famously on and off. Very much so. And that final
off status in early 2023 opened the door for
the current era. the timothy chalamet era i remember
when the rumors started in april 2023 i thought
it was a joke i thought it was a fan fiction
headline timothy chalamet the indie darling the
dune guy and kylie jenner on paper it seemed
like a complete mismatch of brands he represents
high art and prestige cinema She represents commercial
reality TV and influencer culture. Two different
universes. But when they stepped out publicly,
especially at the Golden Globes in 2024, it sent
a very clear signal. What was the signal? The
signal was, I am not just an influencer. I am
Hollywood. Dating Timothee Chalamet creates a
proximity to prestige that money can't buy. It
legitimizes her in circles that previously might
have looked down on the Kardashians. It's a strategic
social move that has business implications. Absolutely.
Which brings us perfectly to where we are right
now in 2026, because she is making this massive
career change. She is acting. She is. She has
a starring role in the film The Moment, which
is set to come out this year. And it's not like
a throwaway comedy or a cameo. It's produced
by Charlie XCX and Studio 365. It has this indie
cool girl vibe to it. This is a very significant
move. Yeah. You know, Kim Kardashian tried to
act. And while she had some moments in Tyler
Perry movies, she never fully crossed over into
being considered a thespian. Right. Kylie is
trying to make that jump. She wants to be taken
seriously as a talent, not just a personality.
Do you think she can pull it off? Can she actually
act? That is the billion -dollar question, isn't
it? She has spent her entire life performing
for a camera, so she's comfortable there. But
reality TV performance is very, very different
from scripted character work. A completely different
skill set. If she succeeds, if she gets good
reviews, she extends her career by decades. If
she fails, if she's panned, it just reinforces
the trashy reality star stereotype she's been
trying to escape. She's also still breaking records
on social media, which is kind of mind -boggling.
She was the first woman to hit 300 million followers
on Instagram back in 2022. And just holding that
level of attention for nearly 20 years is unprecedented.
Usually, internet fame has a half -life of about
18 months. She has stayed relevant through the
age of Vine, Snapchat, Instagram, TikTok. She
adapts to the medium. Even with the music video
cameos. I mean, she was in WAP with Cardi B and
Megan Thee Stallion. Which sparked a petition
with hundreds of thousands of signatures to have
her removed from the video. People were furious.
But again, controversy creates cash. It kept
her name in the conversation. And more recently,
appearing in A .G. Cook's video for Residue.
A much more niche calculated move. Very. She
is aligning herself with the hyper pop avant
-garde crowd. It's a very specific rebranding
strategy to appear culturally relevant to the
Gen Z and Gen Alpha audience that might not watch
her family show. So. Okay, if we step back and
look at the whole picture, from the lip kits
to the Forbes scandal to this acting pivot, what
is the big takeaway? What's the lesson here?
For me, it's that Kylie Jenner is a mirror for
the modern economy. She proved that you can monetize
anything, your face, your relationships, your
children, even your own insecurities, if you
package it right. I agree. She represents the
attention as currency. thesis. She proved that
in the 21st century, attention is more valuable
than oil or gold. If you have the eyeballs, you
can sell the product, but there's a but. The
Forbes retraction and the Kylie Swim flop show
that there is a limit. Yeah. You can bluff your
way to a title and you can hype a bad swimsuit,
but eventually the truth comes out. It comes
out in the tax returns or the customer reviews.
Exactly. You cannot fake quality or truth forever.
Gravity always wins. And that's what makes this
2026 acting pivot so interesting because you
can't really fake acting, not in a serious film.
The camera catches everything. It does. She is
moving from an arena where she controls the edit,
her Instagram feed, her reality show to an arena.
So here is a provocative thought to leave you
with as we wrap up. Kylie is clearly diversifying.
She's moving away from just being Kylie the face.
She's acting. She's doing clothing with Kai that
focuses on design. She's doing Sprinter. Is she
acknowledging? Maybe subconsciously that the
influencer economy has a ceiling, that a personal
brand built entirely on your own face and life
has a shelf life. I think she is. I think she
knows that King Kylie cannot reign forever. A
meme can only last so long. She is trying to
build a legacy that exists outside of just being
the youngest sister. The real question is, will
the audience let her evolve? Or is she trapped
in the caricature she so brilliantly built? Something
to think about. Thanks for diving in with us
on this one. Always a pleasure. We'll catch you
on the next deep dive.