When it comes to turning fame into fortune, no family does it better than the Kardashians and Jenners. But behind the headlines, billion-dollar brands, and social media firestorms are three women whose business instincts, risk-taking, and relentless work ethic have redefined what it means to be a celebrity CEO. From Kim Kardashian’s shapewear empire to Khloé Kardashian’s denim revolution and Kylie Jenner’s meteoric rise in beauty, we’re breaking down their most iconic business moves—complete with all the drama, anxiety, and hustle you never see on Instagram.
Kim Kardashian: From Reality Queen to Shapewear Mogul
For Kim Kardashian, the seeds of her shapewear brand were planted long before the world knew her as a business tycoon. “Kimono is my shapewear brand. It’s been at least a decade in the making,” Kim reveals. “I’ve been making my own for so long—literally getting fabrics and making my own with a seamstress.” That hands-on approach would soon become the blueprint for Skims, a brand that would turn the shapewear industry upside down.
But even the best-laid plans can hit a snag. As Kim prepared to launch, she was faced with a branding crisis: her original name, “Kimono,” sparked backlash for appropriating a traditional Japanese garment. “Reading that letter from the mayor of Kyoto, I felt an understanding,” Kim says. “Kimono is a traditional ethnic dress and truly symbolizes the sense of beauty, spirit, and values of Japanese culture.” The solution? A total rebrand—on a tight timeline.
With just weeks to go, Kim and her team scrambled to relabel, repackage, and remarket the entire launch as “Skims.” “Can we make the September launch timeline at this point?” her team wonders. “By the skin of our teeth.” Kim’s perfectionism and creative control are legendary—she oversees every detail, from campaign shoots to viral marketing ideas. “For the launch, it should be funny commercials we can launch through social media—like a mock infomercial,” she brainstorms, channeling her mom Kris Jenner’s iconic TV energy.
Despite the chaos, Kim’s vision prevails. Skims launches to massive fanfare and quickly becomes a billion-dollar brand, proving that adaptability, self-awareness, and a little humor can turn even a PR disaster into a business masterstroke.
Khloé Kardashian: Denim, Doubt, and Defying the Odds
While Kim was busy reshaping the world of shapewear, Khloé Kardashian was facing her own set of challenges in the cutthroat world of fashion. “There is so much stuff to do to prep for the launch of Good American,” Khloé confides, her anxiety palpable. “Emma made me really nervous telling me about this number and how hard it is to get to that number. Now I’m nervous I’m not going to make my investors and my business partner happy.”
Khloé’s journey hasn’t been easy. For years, she was labeled “the fat sister”—a stigma she’s determined to leave behind. “Now that I’m over that, I don’t want to be known as the failing sister,” she admits. The pressure is on: Good American’s launch numbers are unprecedented in the denim industry. “Emma said it’s never happened in denim history,” Khloé says. “But you’re going to make denim history,” her family encourages.
The stakes are high, and so are the emotions. “I woke up yesterday at 4:30 a.m. for press. Last night, I didn’t go to bed till 3:45 a.m. Ever since Emma told me we need to sell X amount of units, I have so much anxiety.” But Khloé’s vulnerability is matched by her grit. “Sometimes you need to just be present and go, you know what, I can do this and people back me in this because I do turn out.”
Good American launches to a sold-out frenzy, shattering records and silencing the critics. Khloé’s authenticity, transparency about her insecurities, and refusal to give up have made her a role model for women everywhere—and a force to be reckoned with in the business world.
Kylie Jenner: The Billionaire Beauty Wunderkind
If there’s one Kardashian-Jenner who embodies the power of social media, it’s Kylie Jenner. At just 19, Kylie took her biggest insecurity—her lips—and turned it into a global beauty empire. “Ever since I was probably 15, I’ve been obsessed with lipstick and I was insecure about my lips,” Kylie shares. “I would just overline my lips as much as I could, but I could never find a lip liner and a lipstick that were the perfect, perfect match. So that’s how Kylie Lip Kits started.”
What happened next was nothing short of historic. “Kylie Jenner’s lipstick line went on sale at 9:00 a.m. Pacific Standard Time and the kits literally sold out within minutes,” the family recalls. “265,000 people on the site.” Kylie’s genius? She leveraged Snapchat and Instagram for all her advertising. “Social media has been a really big blessing to me because I don’t pay for advertising. All the advertising I do is literally on Snapchat and Instagram.”
But Kylie’s business moves weren’t just about numbers—they were about connection. “Popups are my favorite thing because doing something my fans can go to, interact with, and I could see them—it really is amazing,” she says. Her vision was always bigger than just selling lipstick. “One of Kylie’s dreams when we first started this journey was that she wanted to have an entire line of makeup products one day. I don’t think we ever dreamed that it would happen so fast.”
Kylie Cosmetics exploded, making her the world’s youngest self-made billionaire. Her story is a masterclass in leveraging authenticity, vulnerability, and digital influence to build an empire.
The Hustle, the Drama, and the Sisterhood
Of course, no Kardashian-Jenner business story is complete without a little drama. Whether it’s a branding crisis, sibling rivalry, or the pressure to prove themselves, these women never shy away from the hard conversations. “I don’t want to hear this narrative anymore about this work ethic and she’s the only one with work ethic and she’s doing this, this, and this as if she’s better because she works more,” Khloé snaps during a heated family meeting. “We don’t all have to do things the same way. If I wanted to be a stay-at-home mom, that’s fine too.”
But beneath the feuds and the headlines is an unbreakable bond. They celebrate each other’s wins, push through the setbacks, and remind each other to “just bask for five seconds in something great.” Their success isn’t just about money or fame—it’s about rewriting the rules, supporting each other, and proving that you can build something extraordinary on your own terms.
The Takeaway: More Than Just a Pretty Face
Kim, Khloé, and Kylie have faced criticism, self-doubt, and public scrutiny every step of the way. But their willingness to take risks, adapt to challenges, and stay true to their vision has made them icons—not just of pop culture, but of modern entrepreneurship.
From shapewear to denim to lipstick, their brands are more than products—they’re statements of confidence, resilience, and the power of reinvention. And in the end, that’s the real secret to the Kardashian-Jenner business empire: it’s not just about what you sell, but how you own your story.