The Rise of the Feminist-Adjacent Startup

Karen Young showed up at the CoLab-Factory with a one-minute speech in her head. Pitching has always freaked her out. Even the most casual coffee meetups are enough to frazzle her. But today’s was another level. Her audience would be somewhere around 40 women — the competition — and three judges. And she had just one minute. One minute to explain what she’d been working on for the past three years. By now she knew the drill: pick a text, don’t ramble, winnow your life’s work down to bullet points, smile. So as women filtered into the room, she clutched her rose-gold iPhone like a safety blanket, staring at the single paragraph she’d stayed up memorizing the night before. It had been just two days since she’d clicked on a Facebook link advertising this event. She was, above all else, tired.

Like all the other women filing into the Downtown Brooklyn coworking space that June evening, Young was participating in the “InnovateHER: Innovating for Women Business Challenge.” The Small Business Administration created the event two years ago to support female entrepreneurs, who still have a much harder time raising venture capital than men do. Before the event, each participant was asked to submit a comprehensive business plan, which, alongside a one-minute pitch, would be evaluated by the judges based on a point system. The winner of the regional contest would then go on to compete on the national stage for a first-place prize of $40,000 (with $20,000 for second place and $10,000 for third) to put toward a business.

To most major venture capital firms in the Bay Area, that sum would be considered a pittance. But the people gathered that evening were not who you’d usually spot in the halls of legendary Sand Hill Road venture capital firm Kleiner Perkins Caufield & Byers. For one, they were women. And a diverse group of them, at that. They ranged from their early 20s to late 60s, wore hijabs and baseball caps; some spoke with thick accents. They were black, white, Latina, Korean, Chinese, Middle Eastern. Their pitch-day uniforms ranged from shift dresses to athleisure. As they filed into row after row of plastic chairs, their fundraising war stories filled the room: Was the Shark Tank application process worth it? How much cash were they giving out for those WeWork Creator Awards this year? Have you tried talking to so-and-so?

In the crowd was the energetic founder of a self-described “Dollar Shave Club for your uterus” who had spent the day driving up from Washington, D.C. Toward the front of the room, a swan-necked former Phantom of the Opera dancer was fine-tuning the explanation of her website, an “OpenTable for boutique fitness classes.” And next to her, in a leather tank top, gray skinny jeans, and flats, was Young. The measured 38-year-old Guyanese American was there to pitch Oui Shave, a startup that sells safety razors — metal contraptions with sharp, replaceable blades — for women.

“It’s so nice to see so many women business owners,” said Ebonique Ellis, an event organizer and a local business development executive, before introducing her two fellow judges on the panel, both male. “One of you will be a Fortune 500 one day, and I’ll say I helped.” For the next three hours, the contestants cycled through their business ideas in random order and fielded questions from investors. When it came time for Young to make her case, she stood at the front of the room, adjusted her square-rimmed glasses, and delivered her paragraph:

“Hi, I’m Karen Young,” she said calmly, though she swears she was shaking. “I’m the CEO and founder of Oui Shave. … In 2015 I launched Oui Shave to provide a better solution for women that actually meets and caters to our needs. So Oui Shave offers high-quality razors, blades, and grooming products that are actually catered to women, and created for and by women.” As Young rattled off achievements like 300 percent growth last year, partnerships with stores, and media coverage, Ellis flashed her 10 fingers to signify 10 seconds left, but Young barely flinched. “And most important, our customers describe the experience of using our brand as ‘life-changing.’”

A new class of female founders is emerging, despite the various institutional traps that await them. Last year the Kauffman Foundation, which focuses on entrepreneurial advancement, found from 2015 data that women comprise about 41 percent of new entrepreneurs — a number that has been slowly rising over the last decade. But as more women and gender-nonconforming people start businesses, they face significant challenges. First and foremost, they must navigate a fundraising system that, as research shows, is still heavily controlled by men. According to Ethan Mollick, an assistant professor of management at the University of Pennsylvania’s Wharton School, only between 2 and 6 percent of female founders receive VC funding. More broadly, they must also fight for respect within a capitalist system that doesn’t typically reward their gender. As more women-run companies emerge, the messaging of their brands — and how they relate to women — is just as important as raising venture capital.

The funding gender gap can be blamed on many things: Societal forces have produced a smaller population of women with technical skills and conditioned them to be less forthcoming in touting their accomplishments with the same confidence as a man. There’s also the frequent occurrence of male investors making sexual advances at pitch meetings. But often this well-documented lack of interest by investors in female-led companies is intertwined with the product itself. Anecdotally, female founders who started businesses that mainly target female consumers have vented that their struggle to raise funds stems from a fundamental misunderstanding among genders. Though there have always been exceptions, men are often uninterested in funding a product that they don’t understand or can’t personally use.

After years of investors shunning female-centric products, the pitch meeting became its own ground for challenging the gender gap. Not only was there potential for a real scalable market (women make up more than half of the U.S. population and drive 70 to 80 percent of all consumer purchasing globally), but pushing for new and innovative ways for women to shave, catch period blood, or dress their plus-size bodies became a form of advocacy in itself. Out of this funding vacuum grew a new ideological trend helpful for both board-room interactions and the bottom line: startup feminism. Rather than privately battle with issues of their gender’s representation, an emerging generation of founders begun to embrace it publicly, integrating messages of female empowerment into their product campaigns and their own personal brands. And in doing so, some have perpetuated a quasi-feminism that reads as hypocritical.

Startup feminism owes its beginnings to figures like Sheryl Sandberg, a woman who excelled at navigating the man-made corporate structures of major tech companies, and publicly addressed gender inequalities in the workplace (even if her advice placed the onus on individuals to do more, and earned her criticism for being a white feminist). And more recently, a handful of younger female founders have risen to fame by launching companies from nothing while touting their unapologetically bold business dealings. In 2006 Nasty Gal CEO Sophia Amoruso began building an e-commerce empire that sold edgy, vintage-inspired clothing designs. By the time it began making real money, she’d styled her hair in a signature businesswoman bob and developed a reputation for persistent negotiation tactics, refusing to take no for an answer when approaching designers to collaborate. She has built her brand of Girlboss feminism off of her origin story in the form of a self-help book and a (recently canceled) Netflix series. Miki Agrawal spread the word about her period panty company Thinx in part by telling the story of how she turned a male VC into an investor after making him try on a pad. When the New York subway system initially refused to run her company’s ads — some of which depicted a grapefruit that resembled a vagina — she complained to the press about the taboos that surround periods, and the story spread. The campaign was eventually approved, and her company emerged as a prominent vehicle in the fight for normalizing conversations about menstruation.

But Amoruso and Agrawal intertwined their identities so tightly with proclamations of female empowerment that their personal brands fell apart and their companies’ reputations were damaged the moment there was a whiff of hypocrisy. Amoruso’s unraveling began in 2015, when one lawsuit alleged her company fired multiple employees prior to or during their parental leave, and another accused her of laying off an employee who was suffering from advanced kidney failure. A Jezebel investigation described a miserable work environment and Amoruso as self-obsessed and vindictive. She eventually left the company, which went bankrupt in 2016. She is currently running her foundation, which she launched in 2014, in line with her Girlboss brand.

A similar fate befell Agrawal this year, when a report from Racked revealed that many of the company’s employees were apparently offered “substandard pay, flimsy benefits, and scarce perks,” all while enduring an abusive workplace environment. A few days later, a former employee accused Agrawal of sexual harassment, specifically alleging that she had a propensity to discuss the shape of and touch her employee’s breasts, as well as details of her sexual experiences and her desire to sleep with one of her employees, among other things. She stepped down from her CEO role just before the Racked report and lawsuit came out while grasping at the self-appointed title of “SHE-EO.” In June she emerged from a brief press hiatus to speak at an event in New York called “The Truth About Leadership.” An invite sent to the press promised her “awesomely unabashed” point of view on “fantastically taboo subjects: transparency, truth-telling, and the tests that teach us.”

Revelations about these two founders hit hard, particularly because they were living reminders that when you pit feminism against capitalism, the latter tends to prevail. “In a cruel twist of fate, I fear that the movement for women’s liberation has become entangled in a dangerous liaison with neoliberal efforts to build a free-market society,” Nancy Fraser, a professor of philosophy and politics at the New School for Social Research, warned in a 2013 Guardian column. “… Where feminists once criticised a society that promoted careerism, they now advise women to ‘lean in.’ A movement that once prioritised social solidarity now celebrates female entrepreneurs. A perspective that once valorised ‘care’ and interdependence now encourages individual advancement and meritocracy.” Even if a new generation of women were building successful businesses, they were still operating within the confines of a system that was created by men. And in many cases, that system works to the disadvantage of women and minorities.

“So much of corporate feminist initiatives now don’t necessarily have to do with changing the system of startup culture or venture capital culture,” Bitch cofounder and We Were Feminists Once author Andi Zeisler told me. “They just have to do with women benefiting from those spaces and then sort of replicating the same corporate culture or power dynamics.”

In the midst of Amoruso’s and Agrawal’s controversies, the media questioned whether it was wise to make the next generation of feminist leaders women who were capitalists first. The Guardian’s Arwa Mahdawi declared that “capitalism has turned feminism into a meaningless lifestyle choice we can all buy our way into.” BuzzFeed’s Doree Shafrir wondered: “Is it possible to be a committed feminist and a committed capitalist at the same time? And why are we still so surprised when these women — who have built brands on saying the things we want to hear — turn out to be just as flawed as their male peers?”

The jury is out on Agrawal and Amoruso, but the business world’s ability to push for gender equality isn’t entirely doomed. More and more female-run startups are angling to disrupt the mainstream consumer market by identifying classic consumer staples for women, improving them, and dignifying the way they’re marketed to the masses. But if feminism is the pursuit of social, political, and economic equality among genders, then these companies fall somewhat short of the cause. Even if they’re finding respectful ways to talk to women about their bodies, they aren’t necessarily leading the political movement to upend the systems that strive to control them. Nevertheless, they are pushing to eliminate the judgmental gaze on women’s bodies in whatever capacity they can. The result is an emerging almost-feminist consumerist movement that customers have embraced. And even if these businesses have a limited effect on the continued fight for women’s liberation, Zeisler said that they still allow feminist advocates to invest dollars in companies that profess to respect women.

“There are certain things that I have to purchase, just as part of living my life as a human in the world,” she said. “Among those things might be menstrual products or deodorant, or razors or whatever. If there is a choice between something that is mass-produced, made by a company that doesn’t seem to care about its employees and what they’re selling, or a smaller company that’s founded by a woman, that sources their ingredients and packaging responsibly, there is a sense that this is one small way that I can live my larger ethical belief.”

To better understand the limitations and benefits of these feminist-adjacent enterprises, I spent time with three women running startups: Young of Oui Shave, Lauren Schulte of The Flex Company, which sells menstrual discs, and Nadia Boujarwah, who runs the plus-size-clothing subscription startup Dia&Co. All three are in different stages of funding, with staffs that span from five to 300 and their own unique operational issues to tackle. But most important of all: They’re women making products that appeal to the market beyond cisgender men. Their ambitions have, by default, led them to both represent progress in gender equality and use it as a branding strategy. Their company messages are part of an apolitical startup trend that demands women be placed on a level consumerist playing field with men.

I first became intrigued by the precarious position of the female startup founder after attending a dinner with Schulte in October 2016. I’d interviewed her for a story on Silicon Valley’s quest to disrupt periods, and she’d invited me to celebrate the launch of her company at The Little Beet Table in New York. The crowd was largely blond and attractive women, a smartly dressed set of entrepreneurs who sipped wine and picked at family plates of roasted vegetables and quinoa while discussing their personal discoveries at Burning Man. Some were alumni of the all-powerful Y Combinator program that Schulte and her cofounder, Erika Jensen, graduated from in August. (Agrawal was invited but did not attend.) Schulte later sent a follow-up email after the dinner that read, “Consider yourselves the first official members of the #UTERATI girl gang.”

Schulte’s dinner felt like a deliberate answer to Silicon Valley’s all-male power-player networks, which are known to bond over pickup basketball games, ski trips to Vail, and all-male dinners with Al Gore. Here was an informal gathering where influential women could have a few casual glasses of wine with the bonus of maybe making a business connection. As inclusive as her intentions were, the dinner also felt like the accidental makings of its own elite culture, one in which the largely white population of former industry executives, Ivy League grads, and prestigious incubator alumni consolidate their own power.

Nearly eight months later, when I sat down with Schulte on the rooftop patio of Flex’s airy, three-floor Venice Beach office, that was the first thing she brought up. The weekend before she’d been one of 200-something people who attended a garden party at the Los Angeles–based early-stage VC fund CrossCut Ventures, an annual event put on by the firm to support women in tech.

“It was so crazy walking in there because Erika and I looked at each other and we were like, ‘We’re all blonde,’” Schulte told me. “Most people were under 30. It was this really stark, kind of upsetting, unsettling thing. You hear it. To see it is like: Oh, if you’re pretty and blond, you get funding more than if you aren’t.”

Though it wasn’t necessarily easy for Schulte to raise funding at first, she does fit that description. The 31-year-old Georgia native has sandy blond hair, a bright grin, and a tendency to burst into small, joyous fits over minor company victories. She’s tall and lanky, which contributes to her self-proclaimed clumsiness around the office. Her wardrobe appears as if plucked from the chic boutiques that line the office’s neighboring Abbot Kinney Boulevard: airy tank tops, distressed jeans, loose knit sweaters, and stylish tennis shoes. She built her career in marketing at companies like IBM and Coca-Cola, and, as an homage to her brand, she wears a delicate gold necklace with a charm in the shape of a uterus. On most days her outfits seamlessly blend with the packaging and website of Flex itself: a mix of blacks, creams, golds, and beiges that are, as the company brand book dictates, “inspired by the beauty of cycles in nature.”

Schulte developed the disposable Flex disc — which fits under a woman’s cervix to catch menstrual blood — because she was getting yeast infections from tampons and didn’t like the other menstrual-cup options out there. When she started the business in 2015, her hypothesis was: Tampons offered a poor user experience, and women had simply learned to deal with them. But in the early days of raising money for Flex, Schulte quickly learned that the only way she would be able to convince male investors that there was a market was to get as detailed as possible.

“Women will say to men: ‘Oh, I’m on my period. I hate my period.’ But we don’t say, ‘Oh I’m carrying this hard phallic scratchy wet piece of cotton between my legs for four to seven days and I feel fucking miserable,’” Schulte said. “A lot of guys are surprised when I get that blunt with them about it. But I have to get very specific with them around the pain points, because a lot of men just didn’t believe me that tampons were a problem because they’re so ubiquitous.”

But Schulte’s mission to normalize periods doesn’t stop at conversations with male investors. In the same way more of them likely never imagined how annoying periods could be, she has found that women rarely question whether there are better alternatives to the products they grew up using. She insists dissatisfied women are out there and that it’s her duty to help them. “I always say, ‘I didn’t know I hated tampons until Lauren told me I did,’” her cofounder, Jensen, wrote in a Medium post last year.

Schulte’s team must constantly investigate new avenues from which to draw users who might not even know they want the product. Aside from Facebook referrals, which can sometimes be inconsistent, her company has also worked with YouTube influencers and established referral programs, and they’re also testing street teams and in-person events.

“You have to start with people who have problems with tampons, who know they have problems with tampons,” Schulte told me over lunch at a neighborhood healthy salad shop (the one that serves chlorophyll in its water). “It’s hard to find those people, because, as women, we just suck it up. We’re not looking for menstrual alternatives. We can’t advertise on Google because people aren’t looking for it.”

Menstrual products have an inherently gendered history. Not only have decades worth of advertising characterized periods as embarrassing, but the government’s failure to regulate tampon manufacturing in the early ’80s resulted in thousands of toxic-shock-syndrome-related deaths and lawsuits. Even today, grassroots women’s rights groups have organized to demand that various states drop their tampon taxes and tampon manufacturers be more transparent about their ingredients. To Zeisler, advocating for open conversations about periods is a welcome shift in the way companies engage with customers who menstruate.

“It’s possible to talk about removing the shame from menstrual products in advertising, and putting forth an idea of well, this is just what happens, and this is something that makes it easier,” she said. “Without any sense of like, this is going to make you free, it’s going to make you feel beautiful, it’s going to make you want to twirl on the beach. That is certainly an improvement on the ways in which menstrual products and services have been advertised in the past.”

In Schulte’s mind, her company can thrive only if people feel more comfortable talking about not just periods, but period blood specifically. Even if she doesn’t throw around the F-word as loosely as Agrawal did, the Flex headquarters is ground zero for a movement that feels vaguely feminist. Schulte’s slick white desk is decorated with a gold name card placard that reads, “What Would Beyoncé Do?” The wall directly behind it displays a purple-and-black mural of two naked women holding a flower, flanked by cactuses, a piece she commissioned from local artist Alisha Sofia. Schulte’s laptop and T-shirts worn by her employees are branded with a uterus drawn in the style of a sacred geometric shape, a company logo that came to her “in a dream.” To tie into her company mission of helping with body positivity, she recently featured an essay by a sex worker in The Fixx, her company’s new quarterly print magazine. The week I visited, Schulte was considering commissioning a series from a photographer who takes close-up pictures of menstruating subjects. At one point, the company’s COO (who is also Schulte’s fiancé) whipped out a tampon from his backpack, something he’d used for a photo shoot. “You know you work here when you just randomly find one of these in your bag,” he quipped.

During my visit, she’d recruited Jesse Draper, Flex’s first female investor, to swing by the office and film a testimonial. If Silicon Valley had such thing as venture-capitalist royalty, Draper would be a Bay Area princess. Her great-grandfather was considered the first professional VC on the West Coast, and her grandfather, Bill, followed in stride to secure a legacy for the family. A child Nickelodeon star, Draper formerly hosted a peppy, regionally aired talk show called The Valley Girl Show in which she once hula-hooped with the CEO of a payments startup called WePay and ate escargot with Elon Musk. These days, she runs the L.A.-based Halogen Ventures, an early-stage venture capital fund that invests in female-founded consumer technology companies. She connected with Schulte through her dad, who — after receiving a thorough demonstration of the company’s product via a plastic vagina named Gina — recommended his daughter check out the company.

“I just told this story on a panel with my dad, actually,” Draper said. “He’s like, ‘You gotta go talk to this girl, it’s like, a period thing?’ I was just like, ‘I don’t know if I could use a menstrual cup.’ And he’s like, ‘Why not?’ It got to the point where I was like, ‘OK, I’ll go talk to her.’ I went into that meeting, and she blew my mind. I’m a convert. I use it all the time. I’m obsessed.”

“Can you talk a little bit about that? Body positivity, being yourself,” the director asked as Draper shot her testimonial.

“As a female investor, I think Flex ties into all of my values,” she said in an almost-immediate reply. “I support women in every single way that I can, as does Flex. It makes it not shameful to talk about your period. You shouldn’t be ashamed. All women have one. I think we should make it a much more open conversation, and I think that’s something Flex has opened the doors for. More open conversation in this space.”

The business of “body positivity” has proved to be a profitable one. Beyond occupying brick-and-mortar locations and hosting slow websites, some legacy brands have struggled to resonate with younger generations because their messaging has been aspirational, rather than relatable. Traditional marketing campaigns have long been criticized for instilling a sense of insecurity, rather than confidence, in their customers. And many female-led startups have succeeded in positioning themselves against the advertising world’s unseemly history with women.

Take Dia&Co. The Manhattan-based plus-size-clothing subscription startup sends out five items of clothing per box for customers to keep or send back. These days, their market is a lucrative one. A 2012 study reported that plus-size women are estimated to make up 67 percent of the U.S. female population, a demographic that has grown faster than any other apparel category. Not only does the plus-size industry have a long history of being underserved by high-end designers, but critics like Tim Gunn will tell you that designers have rarely made an effort to understand these customers. Subtle references to this deficiency are tucked everywhere in Dia&Co’s branding. Click around its site and you’ll find a video titled #mybodyfirst, in which CEO Nadia Boujarwah and a handful of other employees describe the negative emotional effects of trying on ill-fitting clothes. “It always seems as though when I try something on and it doesn’t quite fit, that I just need to be a little bit different, that if one part of me were smaller, or another part of me was shaped differently, then I could wear the clothes,” Boujarwah says solemnly, as B-roll runs of her holding a pair of jeans up to her hips in the mirror. “What that feels like, never really gets easier.”

The same way that Agrawal once plastered her controversial ad campaign throughout New York City’s subway system, or Schulte has hired artists to make period-centric art, Boujarwah took on the mainstream fashion industry in a full-page New York Times ad. Timed to New York Fashion Week in February, it was a simple page of text that read, in bold black letters, “Fashion she can’t wear is becoming a bit unfashionable,” above a statistic that counted 100 million plus-size women in the U.S. The company scanned it and sent it out to news outlets as part of its #movefashionforward campaign, which aimed “to shift the ongoing conversation on size inclusivity from talk to action.”

“It’s so clear to us that her relationship with fashion is so misunderstood by so many people,” Boujarwah told me when I visited Dia&Co’s colorful Tribeca offices in April, referring to the mythical “her” that she strives to serve each day. “There came a moment where we had to really decide: What are we going to do? We are her biggest advocates and will continue to be the loudest voice in the room on her behalf.”

Dia&Co’s ad was also a play to heighten the company’s profile, generate press, and expand its customer base. But oftentimes businesses that can afford to fund stuntlike advertising campaigns are some of the most effective messengers, at least according to Mala Matacin, an associate professor at University of Hartford’s psychology department who specializes in body positivity.

“In some ways, these companies are the ones who have the access and the money to produce campaigns like this,” Matacin said. “And they have the ability to get it out in mainstream media and ensure people see it. Some people can’t afford to go to college and learn about this stuff. In that sense, I’m very appreciative.”

Dia&Co is by no means the first or only brand advocating for the plus-size population. In 2016 designer Christian Siriano sent five plus-size models down the runway and partnered with Lane Bryant to sell clothing for curvier body types to the masses. Rachel Roy did the same in a collaboration with Macy’s. And a Dia&Co competitor named Gwynnie Bee launched a collaboration with Tracy Reese on a plus-size line. But even as more options open up, Zeisler said companies in the plus-size market still face challenges trying to preach body positivity to customers.

“As with menstrual products, there’s a history of shame,” she said. “That plus-sized women don’t deserve nice clothes, and when they finally size down and lose the weight, then they can reward themselves with nice clothes. These are narratives that have lived in our culture and been perpetuated for decades, so a company like this is a little more political.”

That’s perhaps why Boujarwah’s personal story is so important to the brand. Just as Schulte became a menstrual-disc evangelist via her own journey through tampon hell, the Harvard Business graduate is armed with a lifetime’s worth of experiences rifling through baggy, boring, boxy clothing that she said was ill-suited for her body and style. And, like Schulte, Boujarwah’s willingness to discuss the nitty-gritty details of her reality is a major part of the company’s marketing strategy. The day I visited the office, I witnessed as much. During a styling preview for an upcoming spring campaign, she walked by each piece of clothing on the rack before her touching it in the same emotionless, surgical manner as Anna Wintour in The September Issue. Bourjarwah’s questions, which she steadily shoots at her staff in every visual presentation, range in detail from the pull of a fabric at the waist, to the looseness of a dress’s sleeves, to the lining and hug of a skirt.

Boujarwah is fiercely dedicated to her company’s message of body positivity partly because she has firsthand experience being attacked for what she looks like. In 2014, long before Dia&Co had secured a $20 million investment led by Sequoia Capital, the company was mostly broke. Boujarwah shopped personally for each customer, rifling through clothing racks in Herald Square and sending her finds via free cardboard boxes she got at the post office. So, rather than spend money on models to feature in the company’s Facebook ads, she starred in them herself. The moment the ads went up, a cloud of trolls began leaving nasty comments to cut her down. It was a moment that Boujarwah said catalyzed her crusade for plus-size acceptance.

“It was this bizarre kind of out-of-body experience where you realize that, oh, shit, the work that we’re doing is so important,” she said. “All it did was deepen our commitment to the importance of the work we’re doing.”

That Boujarwah once simultaneously functioned as Dia&Co’s CEO, personal shopper, and model makes sense once you meet her. During my April visit, she rushed in late from getting caught in the torrential rain after a dentist appointment, impeccably dressed in a leather jacket and a flowery, navy-blue jumpsuit, her long voluminous black hair in a casual ponytail. Despite her tardiness, she emitted an inherent calm, a Zen, no-nonsense poker face that added to the glamour of her outfit.

Her consistently fashionable wardrobe tends to come in handy for one of Dia&Co’s main forms of outreach: social media broadcasts. After finding early support among communities of YouTube unboxers, beauty vloggers, and plus-size lovers of fashion, and the active online plus-size community, Dia&Co began hosting its own closet walk-throughs, styling sessions, and unboxing videos on Facebook and Instagram. They offer the same styling tips for vacation, or work, or how to “chambray three ways” that the average fashion blog might. The only real difference is these Facebook Live sessions are always hosted by plus-size women. Even if the messaging in that strategy comes short of advocating for women’s liberation, these campaigns reinforce Boujarwah’s reigning principle: Representation matters.

Boujarwah believes in representing Dia&Co customers so deeply that she has integrated them into the company’s workforce. Her company is 83 percent female. And of that group, around 70 percent of them identify as plus-size. She often hires from the online fan base that helped launch her company. It is a practice that has resulted in a small army of surrogate spokespeople — all impeccably dressed and ready at a moment’s notice to pop on camera and offer tips on how to wear a flowery print or off-the-shoulder top.

The day I visited, Boujarwah was slated to do a livestreamed unboxing of clothing curated by Megan Murphy, an executive assistant at Dia&Co who was one of the company’s first customers. Over lunch Boujarwah proudly told me the story of Megan’s hiring. She brought up a YouTube video between bites of salad. It was a 12-minute unboxing clip posted on Christmas Eve 2014. The company was still in its infancy, and the box that Murphy dissected was filled by Boujarwah herself. The video drew more than 17,000 views and, according to Boujarwah, resulted in something like 2,000 orders. It was only a matter of time before Murphy was recruited to intern at the company and later landed a job there. To this day, Boujarwah refers to her video as “The Christmas Miracle.”

Boujarwah made her way to a bright, upcycled nook on the far end of the office and took a seat next to Murphy at a white table. Today she would be opening a box that Murphy had made for her, for what would be her first personal Instagram Story. A cluster of women with smartphones and cameras trailed behind. After applying lipstick, fluffing her hair, and posing for a few behind-the-scenes photos, she signaled to her social media manager to start.

“Hello Instagram, welcome to my first Insta story with longtime Dia stylist, Megan C. Murphy,” she said smoothly, her voice only slightly higher than her usual monotone delivery. “Megan styled me a box … I feel like a couple of weeks ago? Spring refresh.”

For the next 20 minutes, Boujarwah pulled garment after garment from the container, stopping and starting in 15-second spurts to describe the clothing and declare her love for it. There was a soft, airy top with a “fun twist” detail at the hem, a pink-and-navy, patterned A-line skirt that was simply “beautiful,” and a colorful scarf from Printed Village — which Boujarwah noted makes an excellent beach accessory.

When there was nothing left to unpack, she promised to post a photo of her final look, then moved on to a meeting to discuss the logistics of an upcoming piece The New York Times has in the works about her Sunday routine. All in a day’s work.

Young of Oui Shave didn’t end up winning the InnovateHER pitch competition. She came in second place, after a company called Goals Genius, which streamlined the compliance forms required of special-education teachers. She was happy for the winner, but walking home from the competition, she couldn’t help but feel a little lost.

“It makes it feel like, ‘OK, well, what choices do I have as an entrepreneur?’” she said. “There’s bootstrapping, and then there’s these wiley kind of pitch competitions in the middle. Then there’s venture capital.”

In the same vein as Schulte and Boujarwah, Young founded Oui Shave to solve a personal problem. “Oui Shave started selfishly,” she told me the first time we met at a café near where she and her fiancé live in Flatbush. She’d always had issues with ingrown hairs and razor burn. One day, she was getting a pedicure with some friends and rolled up her jeans. “What the hell happened?” her friend asked. She had become so accustomed to the burns and ingrown hairs that came along with shaving that she’d become numb to the experience.

“Like many women, I just really assumed that OK, well that’s just the side effect of shaving,” she said. “It sucks.”

At first, Young tried nearly every shaving product she could get her hands on: the traditional Venus razors, the big, double-bladed ones, the kind surrounded in smoothing strips. When she still couldn’t find a women’s product she liked, she started digging deeper into the history of the shaving industry. After seeing iteration after iteration of flimsy pink, plastic shaving equipment, she discovered the safety razor: a sturdy metal handle with replaceable blades. Immediately the image reminded her of the contraption she’d watch her uncle shave with when she visited Guyana as a kid. (He always had beautiful skin.) She wondered why such a superior product, though first introduced to women in 1915, was marketed mostly to men. As she dug a little bit more, she also found herself wading through ad after ad that shamed women for being hairy and sold a smooth body as the best way to please a man.

“I thought, not only are the razors bad, but the whole history has been so degrading to women, the entire history of shaving,” she said. “So on top of the fact that the razors are not giving us the best experience, there’s also this sort of continual undertone. I just found that even the advertising and sort of how they spoke to women was still so degrading.”

Just as Schulte and Boujarwah had sought to disrupt female-centric industries whose evolution was steeped in gender inequality and body politics, Young had found her capitalist cause in body hair. More than 99 percent of American women voluntarily smooth their bodies. And those who shave will spend more than $10,000 on related products over the course of their lives. The history of shaving products in America is similarly plagued with a history of lax regulation and insulting marketing practices. In the late 1960s, a woman’s choice to grow out her armpit hair was akin to burning a bra — and even today it’s an aesthetic choice that is far from accepted in mainstream media and pop culture. “Hair removal, at its core, is a form of gendered social control,” an Atlantic piece argued this year. Even if Young couldn’t inspire a generation of women to throw out those products, she figured she could at least sell them in a more dignified way.

“I thought that was really where I could create something powerful,” Young said. “Because there’s never gonna be anything from Oui Shave that tells you, like, this is how you need to be.”

So in 2014 she drew from her experience working at Estée Lauder to build a female-focused company whose marketing approach was less aspirational and more relatable. Something she could turn into a multibillion-dollar brand. She named her razors — which cost between $48 and $85 — Carrie, Charlotte, and Samantha after Sex and the City characters so that, when women came to the site, they felt like they were “hanging out with their girlfriends.” She swapped the typical cake-frosting shaving cream aesthetic for brown-bottled shaving oils and lotions that smelled like lavender and contained none of the synthetic fragrances, phthalates, urea, and DEA that other brands often put in their products. And though her company is still too small to have launched any major advertising campaigns, she has steered clear of filling the site with imagery that fetishizes a hairless body. Her products might not exactly be “life-changing,” as Young has described them, but they remain authentic, matter-of-fact alternatives to more mainstream options.

So far, Oui Shave is a growing (and profitable, Young said) business. In 2016, the company saw 250 percent growth, in part due to a partnership with Anthropologie, Urban Outfitters, and Free People. It’s still a scrappy business. Young and her five employees work on the website remotely, and it is entirely self-funded. Now Young is in the process of casting a signature Oui Shave safety razor from scratch and reaching out to investors to help her take the business to the next level.

Young was raised by her immigrant parents “to be seen, not heard” — a lesson she carried through with her to public school in Brooklyn, where she was incredibly shy. As she grew up, she challenged herself to do more to command the attention of a room, whether it was by raising her hand, competing in a spelling bee, or joining the track team. But she’s aware that her nature — to be a soft-spoken, and generally “chill” presence in any room — may read as a lack of passion to male investors across the table.

“I kept trying to edge my way out, stick my foot out of the parameters of all the things I should not be doing as a woman,” she told me. “And now here I am, and it’s more than my foot. I’m literally trying to take a bat to the system.”

Young knows her brand’s messaging is inherently feminist-adjacent, but feels ambivalent about automatically accepting the label. Though she has been heartened by the outpour of support and advice she’s received from fellow women founders as she begins to court investors, she has also seen the limitations that await her as a black woman in the industry. Not only has she continually encountered all-white women tech panels and summits, but she’s also aware of her poor statistical chances at raising money. A 2016 study from Project Diane found that, from 2012 to 2014, only 0.2 percent of black female founders were awarded funding for their startups.

These are the numbers that were stuck in Young’s head in late April, when she learned she’d made it to the next class of Y Combinator. She was surreptitiously flown into the Bay Area for a 24-hour visit, the purpose of which was a 10-minute meeting with the incubator’s investors at their Mountain View headquarters. She took a Lyft to the office and sat in the company’s lobby waiting for her name to be called. There she watched other contestants, mostly white men, mostly in their 20s, wring their hands and pace back and forth, “wearing holes” into the building’s signature orange carpeting. When it was her turn, she sat across from three of the firm’s partners at a long table, presented her idea, and began to field the rapid-fire questions. When it became clear to her that some of the male partners she was pitching were unfamiliar with women’s shaving rituals, it dawned on Young just how much extra work she’d have to put in to communicate her business idea.

“As a woman and then a black woman, I have to put on, like, three times the game face,” Young said. “Get in there, know your shit, know your numbers, know your business, and also don’t let it get you down that a lot of women aren’t here, and certainly a lot of black people or black women aren’t here either. I think that was hugely frustrating for me. And so now I’m sitting here going: ‘Well, how the hell do I present this business to someone who doesn’t look like me, who doesn’t have my concerns?’”

Soon after the meeting, the investors informed her that she hadn’t made the cut. So she took a Lyft to her hotel, packed her things, and went to the airport. On the flight home, she wrapped her head in a scarf and slept the entire time.

That was Young’s first trip to Silicon Valley and a rude reminder of how the system functions. Before effecting change from within America’s profit-driven economy, she had to wrestle with the fact that someone like her wasn’t always welcome in it. But what choice did she have but to play along? Until the structure of the corporate world changes, the path to growing a business is just the same game, with different players.