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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:

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