A 2021 Retrospective: What We Learned From The Rise of the Female Millennial Entrepreneur

In 2013, I observed a nascent movement bubbling in corporate America that would prove monumental in the years to come. This movement was helmed by young, enterprising millennial women who, while working full-time jobs, were hustling through their nights and weekends to turn their side-gigs into legitimate businesses. In retrospect, they were doing something radical. They were forgoing the traditional corporate ladder climb while laying out a different path for their future; architecting a new route towards success that would change the business landscape forever.

Based on our initial insights, my company, REAL Brand Strategy launched the first study in the U.S. in 2015 that exclusively focused on millennial female entrepreneurs (MFEs). At the time, very few industry insiders would pay attention to this segment as we predicted this cohort of women would defy popular stereotypes and emerge as the first generation of women to disrupt billion-dollar industries en masse. Six years later, these predictions have proven true. We now see MFEs’ unapologetic, collective rejection of the corporate 9-5 in exchange for entrepreneurship as something of a watershed moment, a flash in time that sparked a new culture, a new way of achieving success for ambitious women.

During our study, we spoke to hundreds of women who, at the time, were in the early stages of launching their own companies, including Jen Rubio and Stephanie Korey (Away), Jewel Burks Solomon (PartPic), Lauren Singer (Trash is for Tossers / The Simply Co. / Package Free), Meg He and Nina Faulhaber (ADAY), Eliza Blank (The Sill), and Katia Beauchamp (Birchbox). Every single woman we interviewed or surveyed had taken an ambitious leap forward and doubled down on the opportunities they saw before them, despite the fact that some had only a few years of corporate work experience under their belt.?

These women had big visions and audacious goals (e.g. superceding Victoria Secret) combined with a gut instinct that is difficult to quantify. They saw the potential to innovate in areas where corporate America either seemed to fall asleep at the wheel or discounted their ideas as amateurish, however, through such innovation, they eventually became its most formidable competitors. Their individual motivations differed?— some MFEs were advocates who built their businesses on the same white space opportunities they had tried to communicate to former bosses; others were sacrificial, outspoken feminists who turned gender into an industry. But there was one overarching unifier: They were all competing with corporate giants because embracing risks was, and is, woven into their DNA.?

Additionally, MFEs were the first generation to use social media as a tool to build online communities and hold dialogues that became integral to their brands. Instagram, which launched in 2010, became central to a company’s operations as it provided an immediate database, giving insight into the opinions and behaviors of the people they were attracting, and then provided a way to engage with that demographic directly, in many cases fueling a cult-like following. Many, through their radical transparency, tackled taboo topics that struck the right chord with their audience. Yet even before their online communities were crafted, MFEs were particularly skilled in identifying products and services their customers desired because the businesses they were creating were often catering to the wants of the founders themselves. Thus, many of the categories disrupted by MFEs were either those traditionally aimed towards women, such as lingerie and beauty, or categories like sexual wellness, which still had much scope for product innovation from a woman’s perspective.?

When Marissa Vosper founded (the aptly named) Negative Underwear in 2014, for example, she was purposefully offering the exact opposite of the then-lingerie category leader, Victoria’s Secret, which was still televising its annual Angels show. Vosper determined that the dominating brands weren’t paying attention to her peer’s demands for well-fitting, comfortable lingerie, so she started her own label comprising functional pieces made from high-quality material and ditched the rest. No lace, no padding, no bows nor decoration. At the time, no CEO at a corporation would have taken a leap of faith on this radical idea to shift from “sexy” to streamlined basics because the prospect for success was so low, particularly considering the attractive revenues lace generated. But thanks to bold visionaries like Vosper, the lingerie category looks very different today.

Kim Kardashian’s “solution-orientated” shapewear brand, Skims, is another groundbreaking brand that embraces inclusivity while addressing a modern woman's needs. Skims launched in 2019 and concentrates on innovative fabrics and simple, chic and comfortable fits that make all body types feel sexy and supported. Kardashian is perhaps the world leader in turning followers into loyal customers, yet the Skims launch was met with general skepticism – people failed to take her seriously as an entrepreneur. But, two years later and Skims is now worth $1.6 billion and was the official underwear brand for Team USA at the 2021 Olympics, which is about as big as stamps of approval get. Rihanna also demonstrates such savvy in her Savage x Fenty lingerie collections. While aesthetically her brand appears more in keeping with the lacey designs of Victoria’s Secret, the crucial difference between the two is that every single piece in Rihanna’s line is body-democratic. Nobody is left out. She openly, and loudly, celebrates and empowers all shapes and sizes; the wearer decides what looks and feels sexy on their body, rather than marketing strategies dictating who gets to be “sexy” and who doesn’t. The response to that approach has been epic — not only is her three-year-old brand now worth over $1 billion, but in February last year?Forbes?published an article headlined “Rihanna Delivers Victoria’s Secret Its Final Business Blow,” which outlined how the mogul was poised to overtake Victoria’s Secret to become a “frontrunner in the global lingerie market that’s expected to hit $325 billion by 2025.”?

?Elsewhere, entrepreneurs like Meika Hollender and her brand Sustain have led a wave of change in the sexual wellness category. In 2014, Hollender, then an NYU Stern grad, launched the first-ever natural, fair-trade condom brand. Within the next few years, she secured $2.5 million in funding and distribution in stores like Target and Whole Foods, was featured in Forbes’ 30 Under 30 list, and published her own book:?Get On Top of Your Pleasure, Sexuality & Wellness: A Vagina Revolution.?After significant investment from Combe (Vagisil) in 2019, Sustain’s offerings expanded to include tampons, pads, period-proof underwear, and period cups. And outside of gender-centered categories, Lauren Singer turned a personal challenge to live a waste-free lifestyle into a sustainable living empire, way before living sustainably became a household term. Now, her waste-free store, Package Free, is a multi-million dollar business, but its journey to fruition followed a similar trajectory to those founded by Singer’s MFE peers — her first company, The Simply Co., was funded via a Kickstarter because she didn’t think she’d get corporate backing.

That’s not the case anymore. Entrepreneurial millennials like Kardashian are among the many who proved that businesses founded by women should be taken seriously and can be extremely successful. Together, MFEs demonstrated that women are not only dominant buyers but innovators, equipped with the skill and tenacity to launch products, services, and ideas that disrupt and challenge mega industries and light fires under established corporate behemoths. In addition to e-commerce ventures, their vision spawned the rise of conferences, podcasts, mobile apps, private membership clubs, and so forth, all started by women for women. Collectively, they turned gender into an industry — and it’s booming.

MFEs did much more than formulate and launch innovative businesses; they spearheaded a change in mentality and behavior towards women in business as well as the career possibilities for generations of women to come.