Dated but Not Forgotten: Let’s Revisit the GIRLBOSS Era

What can we learn from the rise & fall of prominent millennial entrepreneurs?

By Haniya Khalid | September 23, 2023

The room is bathed in a soft, warm glow. Velvety sofas in soft shades of pink are arranged in inviting clusters. Clear stools line gleaming marble bars: not an aged wood or jewel tone in sight. Young women wear pastel power suits or Nikes contrasted against summery dresses. 80s hip-hop plays in the background as you’re served a vegan matcha latte. GOOD VIBES ONLY shouts in neon from a wall that’s papered with geo-ambiguous palm fronds. Lettering is modern and minimalist. Puns run rampant, just beyond your tamest office bullpen fantasy. It’s 2016 and you’ve entered the Girlboss era.

You might think that I dislike what I just described, but that’s not the case. In fact, like many young women, I found the millennial pink aesthetic soothing, a gentler conduit to explore femininity than the bedazzled hot pink of the 2000s that had inadvertently nudged me towards the ‘pick-me’ end of the self-expression spectrum. The quieter, seemingly inclusive approach felt like a new and necessary chapter of empowerment: women no longer had to adopt masculine traits to be taken seriously in the business world. For bookish girls who harbored ambitious career goals but (and!) also cared about the perfect blowout or lip balm, there was finally a gap to squeeze into. I had always known that if the buts of a life rich with incongruities could slowly become ands, the world would split open for women everywhere – juicy and ripe and teeming with opportunities. It seemed like it was finally happening.

I liked what was sold to me: women taking care of themselves and each other, prioritizing career growth and self-care, working outside-in to feel refreshed and productive. Having previously steered with the vaguely South Asian philosophy that all efforts must come from the inside-out, and that the longest, toughest way to get somewhere was the only worthwhile way, I welcomed this foreign, breezy way of things.

I memorized Emily Weiss’s infamous pre-wedding grooming ritual, impressed by her loyalty to colonics and chocolate croissants, in full agreement with a need for both (not at the same time, though! Ouch.). I copied her short, baby blue nails and swatched NARS’ Hep Loo lip crayon on my eyelids (a choice I later regretted thanks to my sensitive skin). I bought Glossier products during their phased-launch days when they were sold in packs of threes. I was too young for the first wave of Clinique’s Black Honey craze, so Glossier’s Jam became my daily balmy-but-matte lip product. I opened each translucent pink Ziploc with curious fascination, decidedly confused at the sheet of stickers that came with the cosmetics. I hadn’t used stickers since I was in grade school, if then. Per the status quo of my South Asian-dominant school, I had wrapped my schoolbooks in the ugliest beige paper I could find, thick and sharp – bloody papercuts favored over any semblance of aesthetic or utility.

“What use does a Girlboss have for stickers?” I wondered.

“To decorate your journal in a quirky yet approachable manner, of course!” said a voice in my head, the same voice that kept telling me to order matcha drinks that tasted more and more like dirt that was somehow both wet and dry at the same time.

Determined, I decorated my plain journals in a quirky yet approachable manner. My lips were coated in sheer layers of Jam and my far-apart eyebrows were acceptably symmetrical thanks to Boy Brow brow wax. After many half-discarded lattes, I finally developed a taste for matcha. It was a few days shy of my 26th birthday. I had arrived.

Glossier

“Democratizing beauty”

This is what Emily Weiss claimed quite often during early Glossier days: that it was a tech company, not a beauty company and that their mission was to democratize beauty. It sounded incredible, especially for an industry that at its worst, capitalized off of women’s insecurities to sell them things they didn’t always need. It’s a powerful statement: to democratize something is to make it available to everyone, so it’s fair to assume that Weiss meant the concept of beauty, not the actual product itself (with its price point and limited shade range, democratic isn’t the first word that springs to mind). How can you make beauty accessible to everyone? By creating a rich, diverse community of women. They share their most prized beauty secret. They reach for the same sparkly tubes to achieve an effortless, “me but better” look. They exchange tips on achieving work-life balance. They read the same magazines and follow the same influencers. Above all else, they prioritize their wellbeing. They set career goals and fearlessly march towards them, foamy coffees in tow. In an ironic twist of fate, this community turned out to be the Achilles Heel of the very ideologies that Glossier had been preaching since its inception.

Origin: Into the Gloss, a beauty blog founded in 2010 that peeked into the cabinets of women from varying professions and industries 

Founder: Emily Weiss

Founded: 2014

Model: D2C (direct-to-consumer) beauty & skincare products

Present leadership: Kyle Leahy (CEO)

Funding: $266.4M (seed round, series A, B, C, D and E) from venture capitalist firms like Sequoia Capital and Thrive Capital

Timeline of key events:

  • March 2019 – Valued at $1.2B, Glossier reaches Unicorn status.
  • Aug 2020 – Glossier shuts down two-thirds of its stores and lays off all retail employees; cites COVID-19 pandemic as reason.
  • Aug 2020 – Outta the Gloss, a collective of ex-employees goes public and publishes:
    • An open letter to leadership detailing harassment and racially driven behavior from customers and employees
    • A set of demands for Weiss and senior staff
    • A response to Glossier’s plan of action
  • Aug 2020 – Emily Weiss issues apology via Instagram, promising an equitable employee experience going forward.
  • Sep 2020 – Outta the Gloss starts “Boycott Glossier” campaign.
  • July 2021 – Glossier raises $80M in a round of funding for new stores; announces international expansion.
  • Jan 2022 – Glossier fires 80 tech employees, a third of their total staff.
  • May 2022 – Emily Weiss steps down as CEO and announces Kyle Leahy as her successor.

The Wing

Would you trust Marnie Michaels to run your co-working space?

Marnie Michaels, at times beautiful and alluring, other times toothy and manic, can be many things. Nurturing and empathic do not come to mind, but ambitious and presentable do. The fictional character on the HBO show GIRLS was in part inspired by The Wing founder Audrey Gelman, a close friend of writer Lena Dunham (Gelman even guest starred as Michaels’s mustard-selling, headband-wearing rival on the show). The Wing was a co-working space that ran from 2016 to 2022, making Gelman one of the more well-known faces of the Girlboss era. The Wing was originally marketed as a female-only co-working space for post-Trump era women (it was eventually forced to update its policy to allow men). With a membership fee of $2.5-3K per year (not including food and drinks), it featured conference rooms, changing rooms, and kitchens. The Wing sponsored trips to the Women’s March and regularly conducted mental health workshops. It served as the perfect space for the millennial working woman, a utopian hideaway where you could work on presentations and re-apply your lipstick. That is until accusations of racially driven behavior and performative activism resulted in its permanent closure in 2022. The Wing had always marketed itself as a socially and politically conscious brand, and the timeline of significant global events directly affected both its formation and its eventual fate, making The Wing — perhaps more than any other case discussed — a direct product of its time.

Founders: Audrey Gelman & Lauren Kassan 

Founded: 2016

Model: Club membership (co-working space & events)

Present status: Closed

Funding:

  • $117.5M over 5 rounds (2 rounds of seed funding, Series A, B & C)
  • Investors included Julie Rice (SoulCycle), Haylee Berna (Birchbox), and Airbnb
  • Celebrity investors included Kerry Washington and Mindy Kaling


Timeline of key events:

  • Jan 2019 – The Wing revises no-men policy after facing a $12M gender discrimination lawsuit.
  • End 2019 – By this time The Wing has expanded to 11 locations with 10,000 members.
  • March 2020 The New York Times publishes a report on behavioral and cultural misalignments.
  • April 2020 – The Wing lays off 300+ employees over Zoom; an employee relief fund (a stipend of $500) can be granted, pending acceptance. Checks never arrive for some.
  • June 2020 – The Wing announces that they will donate $200K to BLM causes following the murder of George Floyd in May 2020.
  • June 2020 – Jezebel publishes a report on toxic behavior disguised by performative activism.
  • June 2020 – CEO & co-founder Audrey Gelman resigns amid employee protests.
  • July 2020 – Ex-employee Roxanne Fequiere writes in Elle Magazine about her experience staging “walk-outs” and protests during her time at The Wing.
  • Feb 2021 – IWG buys majority stake of The Wing.
  • Aug 2022 – The Wing announces closure of final 6 locations, citing the COVID-19 pandemic as the main reason.
  • Oct 2022 – The Wing and Audrey Gelman sued for $1.2M for back rent.
  • Dec 2022 – Two more New York landlords sue The Wing for $133K for back rent & unpaid fees.

Man Repeller

Dressing to divert the male gaze 

Man Repeller was born out of fashion necessity. Millennial women longed for better style representation — especially those who didn’t feel an affinity for the hyper-glamorous fashion that was typical of its time. Just as Herve Ledger bandage dresses, Roland Mouret space dresses, oversized diamond watches and velour tracksuits reached peak popularity, so did a contrarian style, a whimsical sort of anti-glamor. Think Zooey Deschanel: Peter Pan collars, headbands, prescriptionless eyeglasses, and throwbacks to the 50s and 60s. This was quickly followed by the Tumblr / Alexa Chung era: brogues, short shorts, drainpipe jeans, trilbies, and throwbacks to 70s icons — all to look like an accessible, friendly rocker chick (it physically hurt me to write rocker chick; I do this for you!). Fresh out of New School, Leandra Medine Cohen was shopping with a friend when the idea of Man Repeller was conceived. Because of her unique eye and effortless ability to captivate an audience, she became one of the first-ever influencers before it was an official term. The millennial popularity of arm candy, “ugly” shoes, and playful silhouettes can at least partially be attributed to Cohen championing wacky, mismatched dressing. Cohen was a skillful writer with a self-deprecating and disarming editorial voice. She furthered the careers of many designers including Rosie Assoulin and Wes Gordon. Ultimately, accusations of misguided internal management and poor treatment of POC employees resulted in Man Repeller’s permanent closure in 2020, leaving behind a legacy that was not as inclusive or representative of its followers as it appeared to be.

Origin: While shopping with a friend, Cohen realized the clothes they were shopping for were “man-repellant” – thus planting the seed for the ethos of Man Repeller

Founder: Leandra Medine Cohen

Founded: 2010

Business model: Blog (sponsorships, affiliate links, native advertising / collabs)

Present status: Closed

Timeline of key events:

  • Over the years: Man Repeller expands to a staff of 16 including editors, social media managers and visual directors.
  • Summer 2020: Employees voice issues regarding exclusionary behavior and content that lacked representation.
  • June 2020: Leandra Medine Cohen steps down from leadership, responding to criticism of treatment of POC & Black employees. Her announcement has been deleted from Instagram.
  • Sep 2020: Leadership team announces a rebrand to Repeller (dropping the ‘Man’ and promising new and evolved content).
  • Oct 2020: Man Repeller announces closure without detailing the reasons for not proceeding with the re-brand.
  • Dec 2020: GQ publishes an in-depth exploration of Man Repeller’s downfall.

A lot can be said about organizations whose growth coincided with the rapid, successive boom of apps like Instagram and Tik-Tok. First is a prioritization of aesthetic through outward expression. Typically, aesthetic is a by-product of sub-culture, not an initiator of it. This started to change around the mid-2010s. Instagram and Tik-Tok encouraged users to represent their sensibilities by simply looking the part, resulting in the explosion of everything-core (normcore, ballet-core, the list goes on). Savvy business leaders picked up on an evolving mode of self-expression, aptly realizing that younger generations wanted to deliberately curate a mood, vibe or fantasy through their lifestyle choices. There is something arguably inspiring about cosplaying your way to your dream life; hundreds of dreams can be brought to life through thoughtfully executed product and design.

Brands like Glossier and mattress start-up Casper spearheaded a shift in marketing strategy that was quickly followed by other business leaders who wanted to stay ahead of the curve. UGI (User Generated Content), influencer sponsorships, digital marketing campaigns, pop-up shops, and an online community was identified as the most effective way to reach the target consumer base. Staying personally connected with the customer through social media was the best way to maintain that consumer base – during the early Glossier days, Emily Weiss would personally like every single Glossier-tagged photo on Instagram, including mine. Casper and Glossier both reached Unicorn* status in 2019 (*when a private startup is valued at $1B or more). In other words, their market dominance was nothing short of remarkable. Their understanding of their consumer? Borderline prophetic.

You rarely hear the expression Girlboss anymore – it had barely entered the household vernacular before quietly crawling right back out, leaving behind the not-so-pleasant implications that tainted the once powerful concept. The problems that caused the perception shift were not new, though: discrimination against POC and LGBTQIA+ employees through tokenization, micro-aggressions, and false promises of growth and development.

What’s left behind is a fossilized reminder of a shared past, one that should compel business leaders to simply do better. To set clear, comprehensive HR policies and ensure that all employees adhere to them through regular audits and manager reviews. To pay attention if an employee complains about harassment and take immediate action when necessary. Take 30 extra seconds out of their day to learn a name that is foreign to them. To never forget that foreignness is a two-way street… if it feels one-way, it’s because one person has made a discreet effort to narrow that gap.

Millennial pink is fading into whatever is next on the trend cycle but what sustains a business is quality product and an honest set of values. In a decidedly digital world, it’s tempting for visionaries to sell the idea over and over again, without delivering on those promised values. Digital markets and ideas are both intangible, but people aren’t, so lofty, idea-centric transactions are simply not enough. Consumers and employees alike deserve more – more attention, importance and credibility.

What can we – specifically women of color — learn from this uniquely tumultuous period? What Emily Weiss accomplished with Glossier is undoubtedly impressive, and her absolute, undeterred faith in her own idea should serve as an inspiration to everyone, especially women of color. In the New World of user-driven media, you can be your biggest spokesperson: in other words, nothing is impossible. Maybe that’s the sign we need to distribute across business-minded women trying to carve a space for themselves in emerging markets and/or emerging regions where venture capital funding is not within the realm of possibility.

If there’s one thing we have collectively learned, there’s nothing quite like a cliché piped in glowing neon to remind us of our unfulfilled potential.

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