Welcome back to the Deep Dive. Today, we're taking
a swing at a figure who is, frankly, just unavoidable.
And I have to admit, when I saw this topic come
up in our stack, I rolled my eyes a little. Oh,
I saw that eye roll. I did. Because usually,
you know, we're tackling hard science or these
huge historical turning points, economic shifts.
And today... We're talking about Kris Jenner.
And I get it. I really do. It's so easy to just
dismiss her as the queen of tabloids or, you
know, the woman who made a fortune off her family's
dirty laundry. Right. That's the public image.
But hear me out. If you strip away the vocal
fry and the salad shaking and all the memes.
Yeah. You are looking at one of the most effective
business operators of the last 50 years. OK,
hold on. That is a massive claim. Business operator.
That implies strategy, spreadsheets, forecasting.
I think most people think her strategy is just
turn on the camera and wait for someone to cry.
And that's exactly why we need to do this deep
dive, because that perception, that right there,
that's part of the product. It's February 2026.
Kris Jenner is 70 years old. She's not just a
reality TV star anymore. She is the architect
of a multigenerational billion -dollar conglomerate
that has completely disrupted the cosmetics industry,
the beverage industry, the fashion industry,
and the media landscape itself. 70. Wow. Yeah.
That's wild to think about. It is. She started
as a flight attendant in 1976. Now, 50 years
later, she's basically the CEO of a family corporation
that has a higher GDP than some small countries.
That's insane. So the mission today isn't to
recap who dated who. I honestly do not care about
the gossip. Thank you. I want to reverse engineer
the machine. How does she actually do it? How
do you turn 15 minutes of fame, which is what
everyone, and I mean everyone, said this was
back in 2007, into a 20 -year dynasty? That is
the part that gets me. It's the longevity. We've
seen so many reality stars just... Burn bright
and then completely vanish? Oh, for sure. The
Jersey Shore cast, the Real Housewives, they
have a peak and then they fade. The Kardashian
-Jenner machine, it just seems to reload. So,
okay. I'm willing to be convinced if this is
a master class in branding. Where does the syllabus
even start? We have to go back to the beginning.
And I don't mean the start of the show. We need
to look at the origin story because it explains
the hunger. You don't build an empire like this
because you're comfortable. You do it because
you're terrified of losing everything. Okay,
so we're talking San Diego, 1955. Correct. Born
Kristen Mary Houghton. Her father, Bob, he was
an engineer. And her mom, Mary Jo MJ, who, you
know, fans of the show definitely know. Oh, yeah,
MJ. She ran a children's clothing store. The
foundational trauma, it happens really early.
Her parents divorce when she's just seven years
old. Seven. That's tough. Her dad essentially
just disappears from her daily life. And then
this is the really tragic part. He dies in a
car crash down in Mexico when she's 19. 19. That's
such a brutal age to lose a parent. You're just
kind of becoming an adult. And then, boom, the
safety net is just gone. It forces a kind of
an accelerated maturity. By 1976, she's working
for American Airlines as a flight attendant.
And I really want to pause here because people
gloss over this part. They just see it as a line
on her resume. Exactly. Just a job she had. But
you have to think about what being a flight attendant
in the 70s actually entailed. It wasn't just
serving peanuts, right? It was still the golden
age of travel. But it was also incredibly demanding.
Yeah. The appearance, the demeanor, all of that.
It was grueling. emotional labor. I mean, think
about it. You are stuck in a metal tube with
demanding, often wealthy people, and your job
is to make them feel comfortable, to handle their
tantrums, to maintain a perfect aesthetic, and
to never, ever crack. You're managing personalities
at 30 ,000 feet. Right. If that isn't the perfect
training for managing Kim, Courtney, and Chloe,
I honestly don't know what is. That's a really
interesting point. It's high stakes customer
service. You have to learn to read a room instantly.
Precisely. And she also worked in her mother's
store, Shannon and Company. So she had the service
element and the retail element completely dialed
in before she was even 22 years old. But then,
then she meets Robert Kardashian. The lawyer.
The OJ connection. Eventually, yes. But in 1978,
when they got married, he was just a very successful,
very wealthy lawyer. She stepped into this role
of the Beverly Hills socialite. Living the good
life. The good life. She had the four kids, Kourtney,
Kim, Khloe, Rob. and live this very very comfortable
life but and this is the first major pivot point
she blew it all up The affair. The affair. In
1990, she had an affair with a soccer player,
a guy named Todd Waterman. Robert found out and
he filed for divorce. And I really want to emphasize
the financial reality here. She went from having,
you know, basically unlimited credit cards in
a mansion to being a single mom of four with
a very, very uncertain financial future. She's
talked about this openly, how she couldn't even
buy a tomato at the grocery store without worrying
about the cost. So the hustle. Yeah. It wasn't
born out of ambition at first. It was born out
of panic. Panic is a powerful, powerful motivator.
She saw the cliff edge. And that experience of
almost losing the lifestyle she had grown accustomed
to, I think that is the engine that drives that
entire family to this day. The fear. The fear
that it could all just go away tomorrow. Which
leads us directly to the rebound. Or, I guess,
the second act. She marries Bruce Jenner. Like,
immediately. One month. One month after her divorce
was final. April 1991. Now, we look back at Bruce
Jenner, Caitlyn now, of course, as this huge
celebrity. Right. But in 1991. Wheaties box was
a long time ago. A long time ago. The gold medal
was 1976. Bruce was sort of a former celebrity
at that point. He was doing the lecture circuit,
but the money wasn't flowing like crazy. So you
have Chris bringing four kids into the marriage.
Bruce is bringing his kids from previous marriages.
Right. Then they have Kendall and Kylie. That
is a massive household to feed. It's like the
Brady Bunch, but with way, way higher overhead.
And this is really where Chris starts to cut
her teeth as a manager. She realized Bruce had
this amazing name, but it wasn't being monetized
efficiently. He was under leverage. Totally.
So she started revamping his press kit. pushing
for more speaking gigs. But the real light bulb
moment, the thing that I think is the Rosetta
Stone for their entire future, was the exercise
equipment. Wait, like the infomercials? Yes,
specifically QVC. In the 90s, Chris and Bruce
were on QVC all the time selling exercise equipment.
It's funny. I feel like people look down on QVC
as this kind of bargain bin TV. Yeah. But the
numbers they do are insane. It is the ultimate
training ground for modern influence. Seriously,
think about the mechanics of it. You have a product,
you have a camera, and you have to talk directly
to the consumer for 10, 20 minutes straight.
You have to create urgency. Urgency, intimacy.
You have to make them feel like they know you.
And because they know you, they should trust
you. And because they trust you, they should
absolutely buy this stair stepper. It's the proto
-influencer model. It's literally link in bio
before the internet. Spot on. She learned right
then that she could move units by leveraging
personality. But by the mid -2000s, things were
getting paid again. The kids were growing up.
The lecture circuit was drying up. And then in
2007, she takes a meeting with Ryan Seacrest.
This is the moment. The big bang of the whole
Kardashian universe. It really is. Seacrest was
looking for a new Osbournes. You remember that
show, Ozzy and Sharon? Oh, of course. It was
huge because it was just so chaotic and dysfunctional.
That's the energy he wanted. And Kris pitched
her family. But the pitch wasn't we are talented
or we are interesting. The pitch was we are crazy.
She literally told him, quote, it would be natural.
She knew her house was a pressure cooker. You
had the older girls running wild in L .A. You
had the Olympian dad trying to maintain some
semblance of order. You had the little kids running
around. She realized that her liability, the
chaos of her blended family, was actually an
asset if she framed it right. And Keeping Up
with the Kardashians launches in October 2007.
And the ratings were immediate. But here is where
the business operator distinction really comes
in. A normal person would have been thrilled
with a hit show. They would have taken the appearance
fees and just enjoyed the ride. Sure. Kris Jenner
did something totally different. She treated
the show not as the product, but as the commercial.
Walk me through that. What does that mean? The
show was the marketing funnel. The goal wasn't
just to get viewers. The goal was to drive those
viewers to go buy things. But to do that, you
need more inventory. You can't just have one
show on the air. You need to dominate the shelf
space. The spinoffs. The spinoff machine. Kourtney
and Kim, take Miami. Take New York. Chloe and
Lamar. Rob and Chyna. Life of Kylie. For about
15 years, there was almost never a week where
some version of a Kardashian wasn't on the E!
Network. Wow. She created an ubiquity that just
made them impossible to ignore. It feels like
she was hedging her bets, too. You know, if Kim
becomes unpopular for a minute, you push Khloe.
If Kourtney wants a break, you push Kendall.
It's a portfolio management strategy. It really
is. She treats her children like assets in a
diversified fund. If one sector is down, you
just lean into another. She wrote about this
in her memoir. She used a chessboard metaphor.
A chessboard? Yeah. She said she wakes up every
day and asks herself, what move do I need to
make today? It's not reactive. It's proactive
resource allocation. She even founded her own
production company, Jenner Communications, to
manage it all. She even tried to trademark Momager,
right? She did. And released a Momager lip kit.
She monetizes everything. But hold on. I want
to challenge this idea that she's some kind of
chess grandmaster who never loses a piece. Because
she has had some serious flops. We tend to forget
them because the wins are so astronomical. But
there were some disasters. Oh, absolutely. And
the failures are actually... in some ways more
instructive than the successes. Okay, let's talk
about them. Let's talk about the talk show. Chris,
the daytime talk show. 2013. Fox gives her a
six -week trial run. They built this set that
looked exactly like her famous black -and -white
foyer. The thinking was, people love watching
her in her kitchen on the reality show, so they'll
love watching her interview guests. And they
did not. It tanked. It was stiff. It felt totally
inauthentic. And that's a crucial distinction
on Keeping Up. She plays the character of the
homomager, you know, a little frantic, overbearing,
funny. Right. On a talk show, you have to be
a host. You have to listen. You have to yield
the spotlight to your guest. And she really struggled
with that format. It was just too traditional
for her. It's so ironic, isn't it? She basically
reinvented the concept of celebrity. But when
she tried to do the old school celebrity job
hosting a daytime show, it just didn't work.
It proves that her brand power is very, very
specific. It works best when she's controlling
the narrative from the inside, not trying to
facilitate someone else's. There were businesses
that failed, too. Yeah. Remember Smooch? Vaguely.
A kid's store. A children's boutique she opened
with Kourtney in 2004. It was standard retail.
You know, low margins, high rent. It closed in
2009. She learned a valuable lesson. Brick -and
-mortar retail is hard, and it's not scalable
in the way she needed. So if brick and mortar
is out and traditional TV hosting is out, that
really only leaves digital. Which brings us to
the billion dollar pivot. Kylie Cosmetics. This
is the one. This is the case study that will
be taught in business schools for decades. So
it's 2015. Kylie is a teenager. She has this
massive. well -documented insecurity about her
lips, which she eventually admits to filling.
And the media is completely obsessed with them.
Obsessed. I remember this, the Kylie Jenner lip
challenge. Oh, God, that was awful. People were
sucking on shot glasses to swell their lips up.
It was dangerous and just ridiculous. It was.
Now, a regular parent might have said, stop looking
at the Internet. This is unhealthy. Let's give
you some therapy. Right. Kris Jenner said, there's
a massive global demand for your lips. Let's
sell them. That is. So dark, but also so, so
profitable. It is the ultimate capitalization
on insecurity. But the business structure is
what's truly genius. They didn't go out and build
a factory. They didn't hire a team of chemists.
They found a company called Seed Beauty. Okay,
explain Seed Beauty. Because that name comes
up a lot in the beauty industry now with ColourPop
and everything else. Seed Beauty, which is run
by the Nelson siblings, is essentially a white
label manufacturer. Basically, they have the
labs, the factories, the packaging, the logistics.
They can make a lipstick, package it, and ship
it for you. Turnkey. Totally turnkey. So Chris
and Kylie struck a deal. Seed handles the entire
back end, all the hard stuff, and Kylie just
handles the front end, which is the marketing.
So Kylie's job is just to post a selfie on Snapchat.
Effectively, yes. The overhead for the Jenners
was virtually zero. Kylie put up $250 ,000 of
her own money from modeling to fund the first
run of 15 ,000 kits. So if it failed, she was
out a quarter of a million dollars. Which is
a lot of money for a teenager, even a rich one.
It is. It was a real risk. But they launched,
and the kits sold out in seconds. I don't mean
minutes. I mean seconds. That's crazy. And because
the manufacturing was outsourced to Seed, they
could scale instantly. They just called them
up and said, make more. By the end of 2016, a
little over a year later, they had done $300
million in revenue. And Chris is taking her 10
% cut the whole time. The standard momager fee
is 10%, yes. But on these joint ventures where
she's a co -founder or an operating partner,
the equity split is likely much, much more significant.
She isn't just an agent taking a commission.
She is a partner building equity. And she didn't
just stop at the finances. She inserted herself
directly into the brand. Oh. The Momager collection.
When she hacked Kylie's Instagram. It was such
a brilliant marketing stunt. It was Mother's
Day 2018. Kris takes over the account, changes
the profile picture to her face, and releases
a collection called the Kris collection. I remember
this. There's a lip shade called Momager. and
a palette with names like i have one word for
tonight vodka it's so meta she's monetizing her
own catchphrases from the show through her daughter's
company which is promoted on the show it's an
ecosystem It's a completely closed loop. She
uses the show to promote the makeup, uses the
makeup to create drama for the show, uses social
media to sell the makeup, and then they talk
about the social media drama on this show. It's
a snake eating its own tail. And she replicated
this exact model with Skims for Kim, Good American
for Chloe, 818 Tequila for Kendall. But there's
a darker side to this level of control, isn't
there? I mean, you can manage a product launch,
but managing a massive family scandal is a totally
different ballgame. And they have had some of
the biggest scandals in pop culture history.
This is where we see the steel, the ability to
compartmentalize. And the biggest test of this,
obviously, was the O .J. Simpson trial. I feel
like younger people especially forget how absolutely
central she was to that entire story. It was
the defining cultural moment of the 1990s. And
Chris was best friends with Nicole Brown Simpson.
They were planning to open a business together.
They were inseparable. And then Nicole is murdered.
And Chris's ex -husband, Robert, the father of
her four children, is on the defense dream team
representing the man accused of killing her best
friend. The psychological toll of that. I just
can't imagine it. Sitting in that courtroom day
after day. She has described it as pure torture.
But look at how she handled it publicly. She
never wavered in standing by Nicole's memory.
She even gave Kendall the middle name Nicole
in her honor. But she didn't completely cut off
Robert. She managed to navigate the single most
polarizing event in modern American history without
being destroyed by it. For the sake of the kids.
For the sake of the kids and for the sake of,
well, sanity. And then you fast forward 20 years
and she has to navigate. The complete dissolution
of her second marriage to Bruce and Caitlyn's
transition. That was a totally different kind
of challenge because it was happening in the
age of social media and reality TV. The whole
world was watching in real time. Right. When
they first separated in 2013, Chris tried to
spin it as a simple growing apart. But when Caitlyn
came out on the cover of Vanity Fair in 2015,
the narrative control completely slipped away
from Chris, maybe for the first time ever. Caitlin
was very, very critical of Chris in that article
and then in her memoir, The Secrets of My Life.
She was. Caitlin accused Chris of knowing more
than she admitted about her gender identity,
of being controlling, of hoarding the family
money. It was ugly. Chris went on the show and
called the memoir all made up. So they were at
war. But, and this is the key, she didn't sue.
She didn't go scorched earth in the press. She
did something much smarter. She went on I Am
Kate, Caitlin's own reality show. Wait, she went
on her ex's show after being bashed in the press
like that? Yes. She showed up. She sat down.
She had the incredibly difficult conversation
on camera. She cried. She expressed her hurt.
Why? That says it was good content. It was great
content. And because keeping the family brand
somewhat intact, even if it's a dysfunctional
brand, is more valuable in the long run than
a clean break, she understands that the audience
craves resolution, or at the very least, confrontation.
That is... ruthless in a way to prioritize the
content over your own personal hurt. Or just
incredibly pragmatic. She knows that if she isn't
a part of the story, she can't control the ending.
She has to be in the room where it happens. Speaking
of which, she has admitted some regrets. The
affair with Todd Waterman, she's called that
one of her biggest. For sure. She sees it as
the thing that broke up her original family unit.
That's a consistent theme for her. So let's fast
forward to the now. The 2020s. The family leaves
E! after 20 seasons. This was a huge risk, right?
They were the entire face of that network. It
was a massive risk, but a calculated one. It
was about the shift from cable to streaming.
E! is linear TV. The audience is shrinking. It's
getting older. Hulu and Disney Plus is the future.
They signed a massive deal to launch the Kardashians
in 2022. Is the show actually different? Or is
it just the same thing with better lighting?
The production value is way higher. It looks
like a documentary now, you know, all these drone
shots of Calabasas. It's very cinematic. But
the underlying strategy is exactly the same.
The show serves as a living catalog for their
businesses. Right. In the new show, you see them
in board meetings for skims. You see Kendall
down in Mexico checking on the tequila vats for
818. It's all designed to legitimize them as
businesswomen, not just reality stars. And Chris
is still the executive producer on everything.
She is the gatekeeper. But look at her most recent
moves in 2025 and into this year. She's stepping
outside of unscripted TV. She's an executive
producer on All's Fair, that new Ryan Murphy
legal drama that stars Kim. This feels like a
quest for legitimacy, like we conquered reality
TV. Now we want an Emmy. That's exactly what
it is. Ryan Murphy is prestige TV. You know,
American Horror Story, Glee, Pose. Partnering
with him signals that they want to be taken seriously
in Hollywood, not just in Calabasas. And she's
embracing the internet culture, too. The Meghan
Trainor video cameo. The mother video from 2023,
it was brilliant. The internet has been calling
her mother for years. It's slang for an iconic,
powerful female figure. Right. And instead of
ignoring it or acting confused like some older
celebrities might, she cameos in a music video
literally dancing to a song called Mother. She's
in on the joke. It's disarming. It's really hard
to hate someone who is winking at you the whole
time. That's her superpower. She makes you feel
like you're part of the club even while she's
selling you the membership. We should also mention
her faith. People might not know she co -founded
a church. Yeah, the California Community Church
back in 2012. It's another layer to the brand,
this idea of faith and family that underpins
the whole operation, at least publicly. So we're
at the end of the deep dive. We've looked at
the tragedy, the hustle, the QVC years, the billion
-dollar cosmetic plays, the scandals. What is
the synthesis here? If you had to sum up the
Kris Jenner philosophy in one sentence, what
is it? I'd say this. Kris Jenner realized that
in the 21st century, attention is a natural resource.
And just like an oil baron, she figured out how
to drill for it, refine it, and sell it back
to us at a massive premium. She shifted the entire
paradigm from being famous to owning the rights
to your fame. That's a really powerful distinction.
Most famous people are employees. They work for
a studio or a record label. She made herself
the owner. And she made her children owners.
That is the legacy. But I want to leave you with
a question, something to chew on. We're seeing
the kids, Kim, Kylie, Kendall, they're becoming
institutions in their own right. They are billionaires
or close to it independently. The momager role
was absolutely essential when they were creating
the chessboard. But now that all the pieces are
kings and queens, is the game over? You mean,
do they still need her? Or, maybe more importantly,
does she need a new game? She's 70 years old.
She's producing scripted drama. She's still with
Corey Gamble. She's a grandmother to, what, 13
kids now? Yeah, a whole army. Is she looking
for a quiet retirement, or is she planning a
third act that we can't even see yet? Knowing
what we've just talked about. I wouldn't bet
on retirement. Neither would I. Not for a second.
Listeners, we want to hear from you on this one.
Do you see her as a cynical mastermind, a business
operator, exploiting her family for cash? Or
do you see a fiercely protective mother who built
a fortress to keep her children safe and rich
in a world that wanted to chew them up and spit
them out? Can she be both? That's the billion
-dollar question, isn't it? Thanks for diving
in with us. We'll see you next time.