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On to today’s deep dive!

Emily Weiss

Emily Weiss, the Founder of Glossier, turned her popular blog, Into The Gloss, into a billion-dollar beauty brand.

It took less than nine years.

In the process, she created one of the darling direct-to-consumer companies, one with a cult-like following.

How’d she do it?

How’d she transform from a 15-year-old intern at Ralph Lauren to the Founder of a billion-dollar company?

There’s a lot to unpack.

Let’s get to it.

Early Days

Emily Weiss grew up in Wilton, Connecticut where her father was an executive at Pitney Bowes and her mother was a homemaker.

She described herself as “really weird” and a “theater nerd” growing up, with a love for animals as well, having a number of different pets, from iguanas to turtles to guppies.

More importantly for our story today, she was interested in clothes from a young age, whether that was the butterfly costume she made for a school play or her imitation “Clueless” outfit she wore to school.

She even wrote a letter to Vogue as a seventh grader:

This interest in fashion would eventually lead to a deeper involvement in the beauty industry and, eventually, the power of storytelling.

But how’d she find her way into the industry in the first place?

Through a neighbor, who Emily babysat for and who one day she found out worked for Ralph Lauren:

Emily started a summer internship at Ralph Lauren when she was 15 and certainly made the most of it:

She ended up interning for two summers and absolutely loved it.

But she wasn’t a great student:

It’s just like another founder I recently wrote about, Dave Portnoy of Barstool Sports, and how he got into Michigan by applying to the nursing school.

These entrepreneurs, I tell you, are just like how Paul Graham described, being relentlessly resourceful. Yes, this is a small thing, finding a different way into their school of choice, but it’s an early sign of their willingness to do things differently.

For Emily, getting into NYU and, more importantly, being in New York, proved important.

She got an internship at Teen Vogue while in college, working three days a week in a number of departments and it was during this time she would famously be called “Super Intern” on the MTV show The Hills.

And her dream around that time?

One day becoming an Editor-in-Chief, aspiring to the likes of Anna Wintour, who has been the Editor-in-Chief at Vogue since 1988.

After graduating from NYU in 2007, Emily had a couple of roles at Condé Nast, working at W for 8 months and then at Vogue, during which time she started the blog that would become the foundation of her beauty empire.

Into The Gloss

In June 2010, Emily published her first beauty article in Vogue. She was hooked right away:

That summer, while at a beach in Connecticut with her family, she conceived the idea for a beauty blog, Into The Gloss:

Emily spent about $1,000 on a Canon DSLR camera and a domain for intothegloss.com, creating the blog on WordPress.

The first post went live in September 2010 and Emily’s “Top Shelf” column, chronicling the grooming routines of famous people and others, quickly grew in popularity.

For context, Instagram launched on October 6, 2010, which Emily would soon take full advantage of.

Reflecting later in 2017 about launching the site, Emily talked about how she thought about the site in the early days, from the content to the technology platform:

And how did Emily find people to feature on the blog?

Of course, not everyone said yes to being interviewed by Emily.

She mentioned how 80% of people said no, but the people she was able to feature helped her get more people to feature.

And remember, she was still working full-time at Vogue at the time, so she made time for Into The Gloss when she could:

It was a slow build at first, but she eventually landed her first sponsor, Lancôme, with a $5,000 brand deal. Kerry Diamond shared how it went down:

The $5,000 was also more money than Emily had ever seen in her bank account before.

She stayed at Vogue for another year after starting Into The Gloss, until October 2011, when it became apparent she had to choose one of them to work on full-time. With the growth of Into The Gloss, she chose to go all-in.

Then, in 2012, she got Nick Axelrod, a former Elle employee whom she previously worked across the hall from, to join her as the editorial director.

Nick would help Emily grow the site from under 100,000 unique monthly visitors to 1 million by the time he left in July 2014.

What helped fuel that growth?

Going from 3 posts per week when it was just Emily to 3-4 posts per day.

Into The Gloss would have more than 200,000 unique visitors per month by early 2012 and 4.5 million monthly pageviews.

A November 2012 profile in the Business of Fashion explained why Emily’s content stood out:

As Into The Gloss grew, it was also building a base of avid readers:

As the readership for Into The Gloss grew, Emily had plenty of directions she could’ve gone with the site, but she chose to stay focused:

In 2013, that would all change.

Starting Glossier

With the hundreds of thousands of potential customers visiting Into The Gloss each month, Emily had the foundation to build her own beauty brand.

In 2013, she took the first step towards making that happen by going out to raise capital to create her own products.

She thought she needed a million dollars to start Glossier. What was this number based on? Absolutely nothing as she’d say reflecting back on the early days of Glossier.

And raising venture capital proved challenging.

After numerous rejections, she was finally able to land her first investor, Kirsten Green of Forerunner Ventures, and ended up closing a $2 million round of funding.

The funding would go towards 8-10 new hires across design, technology, and editorial.

Emily’s initial goal with Glossier was simple: create a beauty brand she’d actually want to wear a sweatshirt of:

Obviously, that was a simple goal for the type of brand she wanted to create.

When it came to creating the actual products, here’s how she thought about it:

Emily was meticulous about the details around Glossier’s October 6, 2014 launch.

Having embraced Instagram soon after it launched in 2010, she had built her personal Instagram to 75,000 and Into The Gloss’s followers to more than 186,000 by 2014.

It makes sense - everyone around her was on Instagram multiple times a day.

The Glossier Instagram account, which Emily had teased over a few weeks, had 13,000 followers by the time her Glossier products were available online, jumping to 18,000+ only a day later.

She teased Glossier’s brand for four weeks before the official launch, with the WSJ detailing her preparations and how she worked with influencers as well:

Initially, Glossier had four different products available for sale: a moisturizer, sheer foundation, face mist, and a lip balm called Balm Dotcom.

Their tagline was: Skin first, makeup second, smile always.

When Emily went out to raise her seed round of funding, all the venture capitalists questioned whether anyone would buy beauty products online. Glossier would be a direct-to-consumer company and investors had their doubts.

Emily quickly suppressed those concerns after Glossier’s strong launch and, a month later, Emily announced another round of funding, this time a $8.4 million Series A led by Thrive Capital in November 2014.

By this time, Emily is leading a team of 25 people.

The next year, Glossier would launch Boy Brow in October, one of their most popular products, and Emily would ask a simple question on Into The Gloss: What’s your dream face wash?

This customer feedback would lead to another one of Glossier’s most popular products, launched in 2016.

With these two products, as well as others, Glossier’s growth would skyrocket, but not without a few challenges.

Growing Pains

Boy Brow was an instant hit for Glossier, so much so that Glossier sold out of its inventory in a number of months, growing a 10,000-person waitlist for the product.

When Milky Jelly Cleanser, the product of Emily’s simple question, was released in January 2016, a similar product obsession ensued from customers.

Demand was so crazy, that Glossier had to write an apology for why they were sold out of as many as 40% of their products, explaining how they had sold a year’s worth of products in the first three months of 2016.

By mid-2016 they had 60,000 customers signed up to be notified when products were back in stock.

Wild.

Emily had no idea the demand would be that crazy, but it was obvious this was an issue. A good issue to have, but an issue nonetheless.

So Emily brought in a Director from Apple, someone with experience in supply chain management, to help with the situation.

Then, in November 2016 Emily announced Glossier’s $24 million Series B led by IVP in a blog post on Into The Gloss, detailing her fundraising experience to date, including her plans with this raise:

Emily has a team of more than 55 people at this point and in December they opened their first permanent retail location, on the sixth floor at 123 Lafayette St. in New York City, calling it the Glossier Showroom.

The next year, in February 2017, Emily was asked if she could’ve launched Glossier before Into The Gloss:

The same year, Glossier launched a “rep” program, allowing people to get compensated for recommending Glossier products:

By September, Glossier had 110 employees in three countries and the next month officially announced their international plans.

The next year, Emily and Glossier would reach a huge milestone.

$1.2 Billion

By early 2018, Glossier’s showroom was generating, according to Emily, more sales per square foot than the average Apple store, and by this time their 22nd product, the Glossier You fragrance, had launched.

The store also was getting 50,000 visitors per month, just showing how popular it was in the city.

In 2018 Glossier made more than $100 million in revenue and had its fourth year in a row of triple-digit revenue growth.

By January of the following year, Glossier had 200 full-time employees and 100 part-time employees, with 29 products.

Then, in March, they announced a $100 million Series D round of funding led by Sequoia Capital.

The round valued Glossier at $1.2 billion.

And Emily’s ambition was way beyond beauty, as she told Vanity Fair when asked about what a hotel, something she’s wanted to create, would look like:

To help Glossier achieve those ambitions, Emily hired Melissa Eamer, a former VP of Sales and Marketing at Amazon, to be COO in September.

Around this time, she also hired a new CTO, CFO, and Chief People Officer.

And yet, not everything worked out well for Glossier.

In March 2019, Emily launched Glossier Play, a “brand of dialed-up beauty extras,“ that was a colorful departure from the typical Glossier brand.

Within a year, Emily hit pause on the sub-brand.

But why did it flop?

A big part of it was how it showed a disregard for sustainability, with excessive packaging and non-biodegradable glitter in one of the products.

Customers were less than enthused.

And shortly after?

The pandemic hit.

Pandemic Struggles

By 2020 Glossier had more than 200 employees and 3 million customers.

They also had 36 different products, significantly less than other beauty brands.

Why?

Glossier’s approach of creating one best-in-class product in whatever category they’re going after.

But then, in August 2020, an anonymous letter from Glossier retail employees came out during the Black Lives Matter protests with all the shortcomings of Glossier, alleging a racist, toxic culture at the retail stores.

The letter demanded that changes be made.

And Glossier’s image took a hit.

There was a great article in The Business of Business that detailed some of the effects, seeing Glossier’s Instagram followers decline and Twitter followers level off, on top of a decline in the business in 2021.

According to Bloomberg, Glossier’s sales were down 26% in 2021.

But Emily seemed to have weathered the storm, overcoming a global crisis and the employee turmoil.

Then, she had to make a difficult decision about the future of the company.

Difficult Decisions

In early 2022, Emily admitted a mistake - she had gotten distracted from the core of Glossier’s beauty business.

With that realization, she laid off more than 80 corporate employees, mostly from her tech team, in January.

While Emily once had grand plans for a technology platform to connect her beauty-enthused customers, it never came to fruition.

Then, in May 2022, Emily announced she was stepping down as CEO, moving into a role as Executive Chairwoman. In August, she introduced Kyle Leahy as the CEO:

In more than a year since Glossier has made a number of changes.

One of the big ones?

Working with third-party retailers.

Glossier is now available in all 600 Sephora stores in the U.S. and Canada, something that customers have been begging for.

And as far as what’s next for Emily?

Even though she stepped down as CEO of Glossier, she’s still very involved with the company and says she’s not going anywhere.

It’s remarkable what she built, she is clearly an incredible entrepreneur even if she had some missteps, and it’ll be fun to see if she stays with Glossier or decides to eventually start something new!

Emily’s Wisdom

In each edition of the Just Go Grind newsletter, I like to include a few more quotes at the end from my research into the founder who is featured, sharing their wisdom.

On what she wishes she’d known before starting Into The Gloss:

On not being afraid to go after what you want: