How I navigated my pregnancy as a Series A founder

The news of Emily Weiss moving to the role of chairwoman of Glossier from her former position as CEO was riddled with gender biases in how it was covered by the media.

Even the more balanced coverage still highlighted that she is currently pregnant, as if it inevitably played a factor in her decision, even though Weiss’ official statement on the matter made no mention of family, pregnancy or children.

There certainly has been progress in recent years, but we cannot deny that we still harbor biases and assumptions about pregnant women in business. “How much time off will they take?” “Are they going to come back?” “Will they work as hard as they did before?” “Who’s going to watch their baby?”

I learned I was pregnant a few weeks after my health tech company raised a $14 million Series A in January 2021. And as someone who had previously experienced the trauma of a miscarriage, I had utterly thrown myself into my other baby — my company. The news of another pregnancy meant I needed to take care of myself and my company in a new way.

While the experience wildly varies and there is no ‘correct’ path to take, I want to share what worked for me while I was a pregnant founder and CEO. Kelsey Mellard

While the experience wildly varies from woman to woman, and there is no “correct” path to take, I want to share what worked for me while I was a pregnant founder and CEO. Women come up to me at conferences or catch me at events seeking specific and actionable advice, so I’m here to share what worked for me.

First and foremost, I decided to be honest with my investors and not delay the news or withhold any information. I hadn’t even told some of my family before I chose to tell my investors — I needed to share the news. Going into the call, I was incredibly nervous, so I decided to not begin with any small talk. My first words were: “I’m excited to share that George and I are having a baby.”

I am lucky enough to have chosen partners like Bryan Roberts and Dr. Bob Kocher from Venrock, Stephen Renfro at Optum Ventures, Hunter Walk at Homebrew and the team at First Round Capital, and they all were incredibly supportive. In the middle of the pandemic, when things looked so bleak, their faces lit up when they heard the news.

Investors are your business partners; they are people with whom you’ll have a relationship that’ll last several years, so it’s important to understand their stance on topics outside of work before you take a check. My investors had chosen to bet on me. So now, me having a baby was going to become part of our new game plan, and they understood that.

How the myth of the ‘girlboss’ harms emerging women in tech

On Lafayette Street in SoHo, young, fashionable women lined up around the block to enter a minimalist, millennial oasis, the most perfect Instagram feed brought to life. Staff members glided around the store in pastel pink suits, each embodying the kind of girl that Glossier made us all want to be: beautiful, yet effortless.

“We want to inspire, but we also want to be realistic and show beauty in real life,” Glossier founder and CEO Emily Weiss said in a 2017 interview with Inc, just as the brand had reached what Weiss herself described as “cult status.” Even Chrissy Teigen and Reese Witherspoon wore Glossier’s signature Cloud Paint blush to the Oscars

We understood the irony of the message as we sampled their sheer, almost-not-there lipgloss, then looked into a mirror decorated with white vinyl letters in the bustling pop-up shop: you look good, our reflection told us. Glossier affirmed our inherent beauty, then reminded us that we can be even more beautiful if we buy their “Boy Brow” pomade, which sold one tube every 32 seconds by 2018.

Glossier’s commoditized feminism aside, it’s no easy task to launch a $1.8 billion company in the brutally competitive beauty industry, especially one with such broad appeal. After all, Glossier’s founder and CEO Emily Weiss is very, very far from the first entrepreneur to profit off of our desire to look good. And who cares? That Cloud Paint is pretty magical, if we’re being honest. Like with many consumer brands geared toward women, we buy in not just because of the marketing, but because of the product itself.

Glossier founder Emily Weiss speaks at TechCrunch Disrupt in 2018

Glossier founder Emily Weiss speaks at TechCrunch Disrupt in 2018 Image Credits: TechCrunch

But as Weiss steps down from her current role and prepares for maternity leave, her success and subsequently typical choice to become her company’s board chairperson has been co-opted as the end of the “girlboss” era.

What even is a ”girlboss” anymore? Once a vaguely aspirational term of praise reserved only for affluent white women, the moniker now reflects the maddening contradiction of workplace feminism: we know that it’s not enough to just be a woman in power, and that what we do with that power matters far more than simply wielding it. Yet women founders and CEOs remain frustratingly rare as Silicon Valley’s glass ceiling persists, almost impenetrable – venture capitalists (only 13% of whom are women in the U.S.) allocate 98% of their funding to startups helmed by men. It’s no wonder, then, how we’ve ended up with the paradox of the “girlboss.” 

The making (and unraveling) of the ‘girlboss’ myth

Nasty Gal CEO Sophia Amoruso is credited with coining the term in the title of her 2014 memoir, “#Girlboss,” which chronicled her rags-to-riches success and was adapted into a Netflix show. The following year, she stepped down as CEO, and by 2016, her company filed for bankruptcy and was purchased by Boohoo. Then, Amoruso started a company called Girlboss that was likened to “Linkedin for Women.” She stepped down from that company in 2020.

“Girlboss” originally gained popularity beyond Amoruso’s book as a form of praise, according to Kirsten Green, co-founder and investor at Forerunner Ventures. Green has spent her career bankrolling the companies that define what’s cool, including Glossier, Outdoor Voices and Away, whose founders are often cited as the archetypal examples of “girlbosses.”

“I truly believe the ‘girlboss’ term was created to celebrate an emerging wave of female leaders – which is still rare in business, and was even rarer around 10 years ago when the phrase was popularized,” Green told TechCrunch in an email. 

The term itself, though, hasn’t aged nearly as well as Green’s portfolio. Years later, even Amoruso herself has expressed discomfort with the phrase.

“It’s not a compliment. It’s more of a mockery,” said Isa Watson, founder and CEO of social media app Squad. Watson, who holds an MBA from the Massachusetts Institute of Technology, has raised $4.5 million for her app, placing Squad in the mere 0.34% of companies funded last year with a Black woman founder.

The idea of the “girlboss” today is shrouded in privilege. Since its debut, the term has come to represent a small cohort of white, affluent millennial women who rise up into positions of power, preach the gospel of feminism, then ultimately fumble the millenial pink ball and fall from grace when it turns out that their politics just aren’t that transformative.

“[The term “girlboss”] feels disconnected from reality, which is that there are very few women that have had this label applied to them,” said Sruti Bharat, who most recently worked as interim CEO at All Raise, a venture fund supporting women and non-binary founders. “They all seem to have slightly similar journeys, like they run consumer brands, maybe [have] slightly problematic racial politics, and some kind of takedown piece [is written about them]. That’s like the PR trope.”

Unlike the glowy skin depicted on Glossier’s Instagram, the reputation of its founder and CEO Emily Weiss is not without blemishes. Glossier’s management has faced well-deserved scrutiny for failing to support members of its retail staff, leaving them to endure racist treatment from customers. (Following the complaints, Weiss issued a public apology, and Glossier donated $1 million – half to organizations fighting racial injustice, and half to Black-owned beauty businesses). 

Then, when the pandemic hit, Glossier laid off all of its retail employees and shut down its physical stores. But just a year later, the beauty brand raised an $80 million Series E round at a $1.8 billion valuation to open up permanent retail stores in Seattle, Los Angeles and London, capitalizing on the dewy fairytale of its Manhattan flagship store.

Mandela SH Dixon, All Raise's recently appointed CEO

Mandela SH Dixon, All Raise’s current CEO Image Credits: All Raise

Early this year, the company slashed staff yet again. Glossier laid off one-third of its corporate employees, mostly on its tech team, as Weiss admitted to staff that the company got “distracted” from its core beauty business and got ahead of itself with hiring. Weiss’ recent departure from the CEO role, along with that of her CMO from the company altogether, only amplified the scrutiny – fairly or not.

Although a select few white women have been able to rise through the ranks of startup success, tech leadership is far from reflecting the populations its products serve. Even All Raise, which was founded with the explicit mission of supporting diverse founders, just recently appointed a Black woman, Mandela Schumacher-Hodge Dixon, as its long-term CEO. Dixon is setting out to broaden the nonprofit’s definition of inclusion after it was helmed by its white, female founder Pam Kostka for three years.  

‘They’re not collecting stats on that’

“The end of the girlboss era? What does that even mean?” asked Rosie Nguyen in a conversation with TechCrunch. Nguyen is founder and CMO of Fanhouse, a creator platform that just raised $25 million from Andreessen Horowitz. 

Despite the prevalence of the “girlboss” in pop culture, the reality on the ground for women entrepreneurs has played out much differently. Less than 2% of venture capital funding went to all-female founding teams in 2021, marking a five-year low. 

There’s a disconnect between the evolution of feminism in the outside world, juxtaposed with the frustratingly slow rate at which Silicon Valley realizes that a woman CEO shouldn’t be a novelty. Outside of work, women fight for an intersectional feminism that’s trans-inclusive, uplifts people of color and advocates for disability rights. But in startup culture, just being a woman in and of itself is seen as subversive.

“As a female founder, it kind of stops there, because that’s impressive enough to people, but I’m like, well actually, I’m also a Vietnamese immigrant,” said Nguyen. “I was born in Vietnam. I’m Southeast Asian. Like, do you know any Vietnamese immigrant female founders in a Series A startup? I don’t know, maybe I’m the only one, but they’re not collecting stats on that… Or, alright, I’m queer, I’m bisexual, but right now, everything is so white and male that anything else is already impressive to people.”  

The confusion around what “girlboss” actually means stems from its application to a broad range of poor management decisions, from the ignorance Weiss displayed about racism in Glossier stores (unfortunately, this is rather common amongst white CEOs) to the dangerous, life-threatening fraud perpetrated by Theranos’ Elizabeth Holmes. 

The “girlboss” stereotype poisons the image of the woman CEO as more and more companies run by white men earn the overwhelming majority venture funding. And of course, those startups are by no means innocent when it comes to bad management.

“If you look at someone like Adam Neumann and WeWork for example, he was covered [in the media] in a very flattering light until the very moment when it all came tumbling down,” said Watson. “I mean, there’s a number of things that went wrong throughout the course of his tenure that were never brought up. And so when you have female founders that have simple management missteps, I just feel like they’re brutalized by the media, and the culture is anxiety-inducing.”

As it is, very few women founders even have the chance to ascend to the top of their field, and those who do are largely white women who come from privileged backgrounds. The female entrepreneurs who succeed by traditional measures are vilified as “girlbosses,” while women of color seem to be left out of the discourse entirely. That’s part of why Bharat, a woman of color with South Asian heritage, says she has never identified with the term.

If Weiss, the founder who built a makeup brand that’s been hailed as the next generation’s Estee Lauder, who pioneered the blueprint for several DTC brands that came after hers, is portrayed as a failure for taking maternity leave and switching executive roles at the company she created simply because she’s a woman, that doesn’t bode well for underrepresented founders without Weiss’s advantages. 

“I think it’s like second- or third-wave feminism, like ‘lean in,” Nguyen said, referencing the catch phrase of controversial, longtime Meta COO Sheryl Sandberg, who just stepped down. “It’s the whole concept of feminism as like, why aren’t more billionaires women? It became laughable to people because the point is not having more female billionaires, the point is having less income inequality.”

The pitfalls of corporatized feminism

While the women who have been branded as archetypal “girlbosses” have largely failed to deliver on the promise of empowering women through selling makeup (or suitcases, or athletic gear), it’s worth examining why they’re even expected to do so in the first place.

“Just because a woman has been oppressed, or has been marginalized, or treated differently, doesn’t mean that she is also aware of how to fix it, or how to speak about it or is not perpetuating it herself. We’re always advocating for women to be icons … but the reality of that is it takes actual advocacy work and movement building and policy,” Bharat said.

The bar is higher for women entrepreneurs not only in terms of financial results they’re expected to deliver (cough cough, Elon Musk), or the thin margin of error they’re afforded, but also in terms of what their job description implicitly includes. The industry doesn’t look to white male founders to serve as perfect advocates for social justice issues. Indeed, the reality of our economic system is that it’s not their job, and whether we like it or not, corporate feminism isn’t going to save us from difficult ethical dilemmas either.

“I really feel for some of these leaders who are trying to learn as they are very much in the public eye,” Bharat said. “There’s very little room for error for women, and I’m not saying there weren’t mistakes. There definitely have been, but the room to recover is completely limited.”

The “Girlboss” label harms all women because it’s a reductive stereotype that detracts from the conversation around real issues in corporate culture and society. It’s a distraction that uses emerging women founders as a scapegoat for systemic issues instead of opening up a productive discussion on how we can reform workplaces to function better for all people, particularly members of marginalized communities.

By conflating all management mistakes as equal, we lose sight of each individual issue we’re trying to remedy – and by calling Weiss a “girlboss,” we risk discouraging women in leadership roles from taking risks, learning and growing. We also perpetuate the erasure of women of color in tech.

This isn’t the end of the woman founder and CEO. Instead, let’s make it the end of unrealistic expectations for women who run companies, and the hollow, corporatized feminism that comes as a result.

TechCrunch+ roundup: The Kindbody TC-1, Glossier’s mistakes, calculating startup runway

Historically, people who have difficulty conceiving children have been stigmatized.

A 2020 UCLA study found that approximately 15% of couples will have trouble getting pregnant, but Kindbody, which has spun up a network of fertility clinics since its founding in 2018, has taken a holistic approach to the issue.

With a focus on education that addresses the fragmentation associated with infertility care, Kindbody is growing at a remarkable pace, but it’s also helping many patients feel seen and heard for the first time.

Full TechCrunch+ articles are only available to members
Use discount code TCPLUSROUNDUP to save 20% off a one- or two-year subscription

In a three-part series, reporter Rae Witte explores Kindbody’s origins, its business, and how it is changing the face of fertility treatments through interviews with its founding team, who have set out to transform and improve the experience of trying to have a child.

With 12 outlets in 10 U.S. cities and unicorn status, Kindbody is poised for growth, having raised more than $154 million.

“We believe very much in the consumerism of healthcare, and what that means is you have to build healthcare around the consumer,” says founder and chairwoman Gina Bartasi.

  • Part 1: How compassion and inclusivity are helping Kindbody change the fertility industry
  • Part 2: Why focusing on holistic care helped Kindbody triple its revenue in 2021
  • Part 3: Chipping away at the problems of reproductive healthcare, one patient at a time

Thanks for reading and have a good week!

Ram Iyer
Editor, TechCrunch+

Does your startup have enough runway? 5 factors to consider

A closeup of a fuel-level indicator from a car dashboard indicating empty..

Image Credits: Jasmin Merdan (opens in a new window) / Getty Images

Myriad factors, like fuel load, ambient temperature and sea level, determine how much runway a 747 requires to reach takeoff speed.

Startups are similar: If the landlord hikes your office rent, a very comfortable 18-month runway could easily shorten to a year. Would that still leave you enough time to get off the ground?

In her latest TC+ post, angel investor Marjorie Radlo-Zandi shares five factors early-stage founders should bear in mind when managing resources, including her simple burn-rate calculator.

“Having 12-18 months of runway between funding rounds gives you time to implement your plans,” she says. “It’s a careful balance of keeping burn rate at a minimum while investing in key areas.”

Mayfield’s Arvind Gupta discusses startup fundraising during a downturn

a rubber duck sits in a lonely puddle

Image Credits: diephosi (opens in a new window) / Getty Images (Image has been modified)

Arvind Gupta, an investor at Mayfield Fund and founder of accelerator IndieBio, reviews several hundred pitch decks each year.

“In 10 days, I can do the primary research and work with the founders to come to a conclusion there. For a larger Series A check. It could take a little bit longer than that, but not that much.”

In a TechCrunch+ Twitter Space last week with Senior Editor Walter Thompson, Gupta talked about how the downturn is affecting seed- and early-stage funding, what he’s looking for, and candid advice for first-time founders trying to raise during a correction.

“You can still finance hopes and dreams, but just with smaller dollars, and you’re generally going to give up a little bit more of your company in terms of dilution during an economic downturn,” said Gupta.

“I expect that to start happening as well in the next year.”

What Glossier got wrong

Technology startup valuations are robust, so it’s only natural that entrepreneurs and investors would want to position firms as a straight tech play, regardless of the underlying business they’re in.

Once public, however, the markets will value you according to the sector in which you actually operate, writes Evan J. Zimmerman, the founder and CEO of Drift.

“The fundamental disconnect is that software-enabled businesses don’t necessarily monetize the same way that software-based businesses do,” Zimmerman says.

And that, he says, is what beauty brand Glossier got wrong, which led to it laying off about 80 staffers, most of whom were from its engineering team.

“That is ultimately the problem that hit Glossier: it forgot what business it’s in.”

Unpacking SailPoint’s $6.9B sale to private equity firm Thoma Bravo

Enterprise security products maker SailPoint’s agreement to be acquired by private equity firm Thoma Bravo lent a sliver of hope to tech startups looking for positive signs in a down market.

But the fact that its valuation sits at roughly 15x ARR could be mixed news for startups looking for an exit, wrote Alex Wilhelm in The Exchange.

“Yes, it is a piece of good news for unicorns worth less than $10 billion because they can benchmark against a recent sale — one that could help them defend double-digit multiples of their ARR. But also no, because companies sell for a premium when they exit to private equity.”

Crypto is altering the investing landscape for even the most disciplined VCs

Image of abstract data visualization on purple background.

Image Credits: Andriy Onufriyenko (opens in a new window) / Getty Images

With more than $32 billion invested last year, and over $11.3 billion so far in 2022, fundraising at crypto startups is showing no signs of slowing, market downturn be damned.

But behind all the fervor, there is a fundamental difference in how investors write checks for startups in the space and what they get in return, reported Jacquelyn Melinek and Natasha Mascarenhas.

“In traditional equity investing, you want to have a Series A or seed-stage investor have 20% to 30% ownership of the company. But having 20% to 30% ownership of a token or of a network is very bad and frowned upon by the community. And web3 is all about the community,” Yida Gao, general partner at Shima Capital, said.

What Glossier got wrong

In recent weeks, Glossier has laid off about 80 employees (or a third of its corporate workforce), most of whom were on its tech team.

Although the company focused on technology when it was really a beauty business, it is not hard to see these layoffs in the light of the public market tech meltdown.

Many venture-backed companies believe they are tech companies — indeed, they were born that way — when in fact they are not. Leaders at these companies need to learn the business they are actually in, what makes those companies good, and direct their technical efforts towards those ends.

The fundamental disconnect: Software-enabled businesses don’t necessarily monetize the same way that software-based businesses do.

Technology companies get the richest valuations and are endowed with the highest multiples of any sector. Pursuing those higher multiples means going to great lengths to show, both operationally and financially, that you “look” like a tech company.

For a firm like Glossier, looking like a tech company is the difference between having a price-to-sales ratio of 5.44, like Estée Lauder, or 31.6, like MongoDB. Glossier founder and CEO Emily Weiss knows it, and her investors do, too.

Tech companies are highly valued for a reason: when they work, they have high growth rates and very high margins. Companies therefore often make product decisions to achieve a tech business profile — like investing in engineering or eschewing margin-hitting operations.

Hunter Walk, for example, pointed out that pursuing software margins may be one reason social media companies avoid the cost center of human moderation.

The difficulty with these types of decisions is that you will direct your technical talent at the wrong problems.

But the narration changes once you go public. The markets work by taking companies, categorizing them, and then evaluating them on well-known metrics. You don’t get to decide what kind of company you are.

You might market yourself as a tech company, and you may very well use technology, but if the public markets decide you’re a beauty company then, well, you’re a beauty company (at least for valuation purposes) until you prove otherwise.

Glossier just laid off one-third of its corporate employees, mostly in tech

Glossier, the popular beauty brand led by former blogger Emily Weiss, let go of 80 of its corporate employees today, according to an internal email obtained by Modern Retail. The cuts, which amount to around one-third of Glossier’s corporate workforce, will primarily impact the company’s technology team.

“[W]e are shifting our technology strategy to leverage external partners for parts of our platform that we’re currently maintaining internally,” Weiss wrote in the email announcing the layoffs to staff.

The email recounts some of the company’s recent mistakes, including prioritizing strategic projects that “distracted” the company from its core beauty business and that executives “got ahead of ourselves on hiring.”

The tech team layoffs are notable for a beauty retailer that has often described it as a technology company. In numerous interviews throughout the past two years, Weiss and other executives have emphasized the company’s focus on its direct-to-consumer online shipping model and obsession with iterating the customer experience based on feedback.

The company built its own point-of-sale system and commerce APIs in-house, allowing them to deliver a “seamless” customer experience, former Glossier CTO Bryan Mahoney said in 2018.

Founded in 2014, Glossier is widely touted as one of the earliest breakout successes of the DTC model, and raised its Series E last July at a $1.8 billion valuation from Lone Pine Capital, Sequoia, Forerunner Ventures, and others. E-commerce sales typically account for 80% of Glossier’s revenue, the Business of Fashion reported last July. 

Despite its fundraising success, Glossier’s ascent has oftentimes been far from smooth. The company laid off its entire retail staff and closed all its physical locations, including its flagship New York City store, in August 2020. It also grappled with the fallout from an open letter written by some of its employees of color sharing their experiences of enduring racism from managers in its stores, prompting a public apology from Weiss.

Nearly a year later, the company seemed to change course on its decision to double down on e-commerce alone, saying it planned to use the Series E funding to open three new permanent physical stores in Seattle, Los Angeles, and London – as well as reopen its New York City location. It hoped to use the retail locations to build brand awareness and encourage customers to create content, areas Glossier became well-known for in its early days through its distinctive, millennial-pink aesthetic and clever use of social media marketing.

The company’s website currently says customers should “stay tuned” for more retail store openings this year.

Extra Crunch Live: Join Anu Duggal for a live Q&A on August 20 at 11am PT/2pm ET

Rent the Runway and Glossier became unicorns within the same week in June 2019. That same year, only 2.7% of venture capital dollars went toward female-founded companies.

Silicon Valley’s disconnect between the monetary success of female-founded companies and funding them in the first place is disheartening. The conversation is there, but the dollar sign momentum remains missing.

Anu Duggal founded the Female Founders Fund before both were even a tangible reality. In 2014, the entrepreneur launched her first fund to invest in female-led startups. It took her 700 meetings over two years to make that first close, she said. Years later, venture capital has slightly taken note. But the Female Founders Fund, or “F Cubed,” has tracked female-led wins and bet big on the underestimated asset class.

Her early focus on female founders hasn’t evolved, but the landscape has. And in an unprecedented world of remote deals and democratization of venture capital, we’re even more excited to have Duggal join us on Extra Crunch Live this upcoming Thursday at 11 a.m. PT/2 p.m. EST/6 p.m. GMT

Those tuning in and taking notes are encouraged to ask questions, but you have to be an Extra Crunch member to access the chat. If you still haven’t signed up, now’s your chance! With the subscription, you’ll also be able to check out all of our stellar previous guests on-demand (watch those episodes here).

Female Founders Fund has provided seed institutional capital to entrepreneurs with over $3 billion in enterprise value. The firm has cut checks into women-led companies such as Rent the Runway, Billie, Tala, Peanut, Thrive Global and Zola. The fund has also attracted limited partners like Melinda Gates and Girls Who Code founder Reshma Saujani.

Duggal herself has a fascinating trajectory into technology investing. At 25, she started a wine bar in Bombay called The Tasting Room. She went on to get an MBA from London Business School, and co-founded, an e-commerce company that got acquired by Indian fashion e-commerce company Myntra in 2011.

Hear from Duggal on August 20 about how the investment landscape has changed for female founders, what she thinks of as a success story and if 2020 feels different than 2014. And Extra Crunch fam, make sure to bring your thoughtful questions for me to ask her live on air.

You can find the full details of the conversation below the jump.

Lyft’s IPO is hot, YC demo day, two new unicorns, and what’s Boy Brow?

Hello and welcome back to Equity, TechCrunch’s venture capital-focused podcast, where we unpack the numbers behind the headlines.

This week Kate Clark and Alex Wilhelm took us through an IPO, a big round, 943 startup pitches, two new unicorns, and some scooter news. A very 2019 mix, really.

Up first we took a peek at the latest from the Lyft IPO saga. Recall that Lyft is beating Uber to the public markets, and we can report that it’s having a good time doing so. The popular ride-hailing company, second-place by market share in its domestic market, is oversubscribed at an already-healthy valuation. If the company will raise its price or the number of shares that it sells isn’t yet known, but early indications hint that Lyft timed its IPO well.

Next, we took a look at the recent OpenDoor round that has been long-rumored. Tipping the scales at $300 million, and valuing the home-buying-and-selling startup at $3.8 billion, the company’s latest equity event was a bit higher than expected. There are other players in its space, and the firm isn’t yet recession-tested. All the same, a Murderers’ Row of capital lined up for the latest round.

Moving on, Kate went to Y Combinator’s Demo Day and got a closer look at the accelerator’s latest batch. There were a ton of two-minute pitches, many of which sounded the same, but chances are we’ll see a few unicorns emerge from the bunch. And, interesting tidbit, some of the companies actually forwent Demo Day and raised capital before they could hit the stage!

Later, we discuss two new unicorns. This week’s unicorns had a theme and one that was new to Equity. This time, both the billion-dollar businesses mentioned on the show were founded by women. As Kate noted, there aren’t too many of those, so to see two in the same week is great.

Glossier, founded by Emily Weiss, brought in a $100 million Series D led by Sequoia Capital . The round values the beauty business at a whopping $1.2 billion, tripling the valuation it garnered with a $52 million Series C in 2018. As for Rent The Runway, a startup founded by Jen Hyman and Jennifer Fleiss, it closed a $125 million round led by Franklin Templeton Investments and Bain Capital Ventures. This round values the company at $1 billion. Hyman took to Twitter to share some inspirational words on raising capital as a woman, a pregnant woman, in heels!

And finally, we took a look at a Parisian scooter tax. Mostly because Alex wanted to talk about Paris.

And that’s Equity for the week. We’ll see you soon!

Equity drops every Friday at 6:00 am PT, so subscribe to us on Apple PodcastsOvercast, Pocket Casts, Downcast and all the casts.

Glossier triples valuation, enters unicorn club with $100M round

Glossier, known for its flagship line of barely there beauty products, has landed a $100 million Series D led by Sequoia Capital. The round values Emily Weiss’ business at a whopping $1.2 billion, fully cementing the company as a startup “unicorn” and tripling the valuation it garnered with a $52 million Series C in 2018.

News of the round was first reported by The Wall Street Journal and later confirmed by Glossier.

“We are building an entirely new kind of beauty company: one that owns the distribution channel and makes customers our stakeholders,” founder and chief executive officer Emily Weiss said in a statement.

As part of the round, which included support from newcomers Tiger Global Management and Spark Capital and existing investors Forerunner Ventures, Thrive Capital, IVP and Index Ventures, Glossier has hired Vanessa Wittman as its chief financial officer. Wittman previously held the same role at Oath and Dropbox. She replaces Henry Davis, who left the direct-to-consumer makeup brand in late 2018. Other recent additions include Edith Chen, Glossier’s new vice president of supply chain operations, and Nick DeAngelo, vice president of operations.

To date, New York-based Glossier has brought in nearly $200 million in venture capital investment, making it one of the most well-funded privately held beauty businesses. What’s next for the company? Weiss tells The WSJ an initial public offering isn’t out of the question, but didn’t provide a timeline. It’s been about five years since Glossier went from blog to business; it still has plenty of time before investors are pushing for an IPO.

Since it launched as a beauty blog in 2010, Glossier has grown into a 200-person business with $100 million in annual revenue in 2018. It has established two brick-and-mortar shops and expanded from au naturel makeup to “dialed-up extras” fit for the Instagram crowd. The recent launch of its first spin-off brand, Glossier Play, hints at a future where Glossier is a multi-brand beauty empire competing with the likes of Ulta and Estée Lauder.

Makeup is a huge and growing industry venture capitalists have been sleeping on. Megan Quinn, a general partner at Spark Capital, who led the round in Glossier on the firm’s behalf, says online beauty sales are expected to reach $120 billion by 2024. She expects Glossier to win the beauty market as a result of its intimate connection with customers, word of mouth customer acquisition channel and community-building tactics.

“To say that [Weiss] is a force of nature obfuscates her true superpower: she is a fantastic listener,” Quinn writes in a blog post. “By weaving her unique point of view with the feedback loops of her community, she has built a platform to power additional brands that respond to her customer’s needs. More importantly, she has built a world-class team of product designers, supply chain experts, marketing muscle, and arguably one of the largest engineering teams in beauty to make it happen.”

Glossier launches its first spin-off brand, a line of Instagram-friendly ‘dialed-up’ beauty extras

Glossier, known for its line of understated makeup products and a cult-following of millennial Instagrammers, is getting colorful with the launch of its first spin-off brand, Glossier Play.

The company — led by founder and chief executive officer Emily Weiss, who built the nearly $400 million business from a makeup blog called Into The Gloss — has raised a total of $92 million in venture capital funding from top-tier consumer investors Forerunner Ventures, Index Ventures and IVP. Stitch Fix founder Katrina Lake and Forerunner founder and general partner Kirsten Green, are among the company’s board members.

Weiss introduced Glossier in 2014 as a clean-skincare and natural beauty advocate. Today, the direct-to-consumer business boasts a growing line of barely there makeup, designed to mimic Weiss’s own subtle, au naturale vibe. The launch of Glossier Play, inspired by 1970s’ nostalgia, is its first foray into bright colors, glitter and, in the brand’s own words, “dialed-up extras.”

“We wanted to explore color the Glossier way,” a spokesperson for the company said. “This meant developing high-quality products without the moody, expert-centric rhetoric of most luxury brands. Glossier Play is all about fun and creative expression. These products were two years in the making, and just like Glossier’s modern essentials, they are designed to stand the test of time (not trend-driven or fast fashion).”

Glossier Play’s initial line-up of “extras” includes colored eyeliners ($15), highlighters ($20), multi-purpose glitter gel ($14) and the “Vinylic Lip” ($16). Customers can purchase “The Playground,” a set that includes each of the new products, for $60.

The advertising campaign for the Instagram -friendly line will be led by none other than Instagram star Donté Colley, as well as pop musician Troye Sivan. The new line and future spin-offs will help Glossier compete with beauty incumbents, Estée Lauder and L’Oréal, for example, in a market estimated to be worth $750 billion by 2024.

Glossier, headquartered in New York, counts 200 employees, meager in comparison to its nearly 2 million — and growing — social media following. The company surpassed $100 million in annual revenue in 2018, it tells TechCrunch, and acquired 1 million new customers. In total, Glossier retails 29 products across skincare, makeup, body, and fragrance.

The company won’t be introducing additional brands this year and clarified it is not a brand incubator.

Uppercase raises $3.5M to help e-tailers open brick-and-mortar stores

People like to say that brick-and-mortar retail is dead, but direct-to-consumer businesses continue to dabble with physical stores all the same.

Why? Because brick-and-mortar retail provides businesses with benefits an online shopping platform can’t, namely consumer experiences that create and sustain shopper’s relationships with brands. 

To help the next generation of digitally native stores expand into the physical world, Uppercase, formerly known as thisopenspace, is launching out of stealth with $3.5 million in venture capital funding. Lerer Hippeau has led the round, with participation from CRV and SV Angels.

Uppercase works with real estate agents, architects and designers to build stores for online brands in New York City, Los Angeles and Toronto.

Co-founder and CEO Yashar Nejati started the company after noticing that online brands were experimenting with pop-up shops then establishing permanent storefronts.

Men’s retailer Frank & Oak, which picked up a $16 million Series C this year, is a great example of that trend. The company began as an internet retailer and now has several stores throughout Canada. Luggage startup Away, trendy shoe company Allbirds and Emily Weiss’ makeup company Glossier have done the same.

“Anyone can launch an online brand,” Nejati told TechCrunch. “Brands truly stand out from the crowd once they grow beyond digital — we’re seeing this with Warby Parker, Casper and Indochino, who will have over 350 stores by the end of 2018. Uppercase is part of a modern growth strategy, providing tech-enabled flexible retail stores for brands to launch, analyze, and grow their retail presence.”

So far, Uppercase has built stores for furniture company Joybird and Venus et Fleur, which sells artfully arranged roses.

Early-stage investor Lerer Hippeau has backed a number of direct-to-consumer brands, including the aforementioned Allbirds and Casper.

“We’ve seen the importance of an omnichannel strategy as companies scale,” Lerer Hippeau Graham Brown told TechCrunch. “Uppercase is the perfect partner for brands born online looking to expand into the physical world.”