The unvarnished story of Glossier CEO Emily Weisss rise and why shes so resilient.
At a startup like Glossier,a surprise department-wide meeting means one of two things: layoffs or treats.
As the man began seeking volunteers for card tricks, several employees fled via the back exit.

Others scrambled to look busy, classic tech introverts desperately hoping to avoid forced interaction.
They had been struggling for years to marshal disparate ideas for Glossiers tech future.
(Was it an app?

A shoppable social web link?)
And Emily knows that something like Glossier is a cultural phenomenon.
So if you dont create new ways of becoming huge, you just become a morbidity of the past.

How was Glossier going to become huge?
Glossier made some mistakes, she wrote to the staff.
Looked at one way, the tech debacle was another story of a startup pivoting and losing its way.
Looked at another way, the layoffs were a sign of Glossiers and Weiss maturity.
The beauty company was giving up on its biggest dreams to make it double down on its attainable ones.
Her brain just works differently from other peoples, says Youn Chang, Glossiers former head of supply chain.
She has this magical element.
Chang was a fan of Weiss before she was her employee.
In 2015, Chang was a global supply chain manager at Apple and moonlighting as a beauty blogger.
Glossier was sold out of everything and Chang wrote to ask if they needed supply chain advice.
I love Glossier, but not that much to dye my hair for this interview, Chang told her.
As Weiss did with many candidates, she asked about Changs horoscope.
Weiss had every reason to be confident.
Customers had bought a years worth in five months and Glossier couldnt make them fast enough.
But I think about it a little bit like, how are religions scaled?
(As Weiss wouldlater write in her letterintroducing Glossier: Snobby isnt cool, happy is cool.)
Soon, ITG had a signature Warhol-esque photography style and an engaged community of product obsessives.
She had gotten so busy shed missed a few days, she admitted.
It was endearing, says an early employee.
It made you want to go to war for her.
Here, Weiss workplace vision was fully realized.
Fashion and art world-beloved florist BRRCH supplied frequently-changing floral installations.
Coconut waters, little cheeses, and fancy yogurts were meticulously arranged in the double-door, clear glass refrigerators.
The smell of burning sage after-hours was no cause for concern.
At some startups, luxury design and amenities might be evidence of reckless spending.
At Glossier, the company was simply living up to its brand values of beauty and community.
My positive experience at Glossier helped me create my brand, says Chang.
Weiss may be a formerVoguestaffer, but she is the anti-Anna Wintour.
Dont get bleach on the floor, she said.
and is shockingly approachable for someone who has admitted on a podcast that she flew to Copenhagen for highlights.
She would say, Oh, you dont know how to do warehouse distribution?
Lets just find a warehouse.
She made it look, not easy, but she made it look really kind of achievable.
Plus, Weiss was in it for the long haul.
I dont have any plans to go away anytime soon.
At each stage of Glossiers growth,Weiss proved her genius for devising beautiful, surprising moments.
Masarin, now the founder and CEO of non-alcoholic spirit company Ghia, says Weiss was immediately on board.
Emily said, I dont really understand this but I trust you, so go for it.
At times, opening stores seemed to take precedence over selling stuff.
The customers werent the only ones making pilgrimages.
I dont know how they managed that, just moving around-wise, she says.
Hats off to them.
Maintaining Glossiers cool required saying no to anything off-brand, and on this front Weiss was decisive.
She was exacting about the products, too.
When customers complained about the Generation G lipstick breaking, Weiss made reformulating and repackaging it a top priority.
Creatively, Weiss is a generational talent.
And if Play did need its own site, how long would that take to build?
Production and photography cost $1.5 million, says a source.
Weiss shut down Play less than a year later.
But talking to former employees, its not an exaggeration to say it remains a source of collective trauma.
Play was a flop,butGlossier had never been stronger.
It required users to give their star sign when they signed up.
Building such an ecosystem proved to be a personnel challenge.
The process really is all driven by Emily, says Capelo.
She values her own intuition more than any expert advice.
Sources say that Peiris lasted barely six months.
He was replaced by Maykel Loomans, from Facebook, who also barely lasted a year.
Engineers say they didnt feel set up for success at a company whose strength was image-making.
The walls looked amazing, but they couldnt be written on.
On the tech front, says Staugas, Weiss wanted to listen and learn.
Weiss could be decisive, but she could be just as quick to reverse her decision.
And just because she sought advice didnt mean it was given to her candidly.
Employees openly wondered: Was love of one brand enough to sustain a whole social data pipe?
But would it only recognize Glossier products or would Glossier start selling other brands?
They probably realized that saying tech was increasing their valuation, he says.
All startups kind of do that.
Its buzzword bingo, and it worked.
Around this time, no amount of palo santo could cleanse the atmosphere.
Members of the tech team began slowing their pace if they saw Weiss getting into an elevator.
There was a lot of doom and gloom and general jaded-ness and people over their jobs, says Staugas.
And Emily was very optimistic about things, almost ignorantly so.
says one former employee), and the company cut back on shipping inventory via air.
Weiss taste remained exact.
Our consumer base wasnt luxury.
Its supposed to be inclusive, says a former employee.
Glossiers behind-the-scenes strugglesmade what played out publicly in 2020 even more remarkable.
I still respect her.
The criticism came at a vulnerable moment.
But if Weiss was rattled, she didnt show it.
She didnt over-apologize, and instead announced steps Glossier would take and how the company would account for them.
Nobody interviewed for this story was surprised that Weiss withstood the blowback.
Internally, few sawthe tech department layoffs coming.
Glossier was still filling tech positions in November 2021, says a source with direct knowledge.
But to those watching the space, Glossiers un-pivoting made sense.
Venture investment in cash-burning direct-to-consumer companies has slowed down, according to PitchBook, especially after some high-profile disasters.
Many venture capitalists have moved on, some to software-as-service bang out companies.
(Green did not respond to interview requests.)
A return to in-real-life shopping experiences plays to Weiss strengths as a CEO.
Shes an effective saleswoman of, well, everything.
(Says Staugas, who is not a fangirl: Every time Emily talks, it is inspiring.)
Her cultural antennae remain perfectly tuned, and she has been as always listening.
Within a week, it was nearly sold out.
Back at corporate, Glossier was making another commitment to the physical world.