[4][5] While interning at Teen Vogue in college, she appeared on The Hills on a three-episode arc with Lauren Conrad and Whitney Port.

[5] She stayed at her day job at Vogue and worked on Into the Gloss in the mornings between the hours of 4 a.m. and 8 a.m.[5] A popular series on the blog is Top Shelf, where subjects are interviewed in their bathrooms and photos of their shelves and medicine cabinets are featured.

[7] After Weiss reached 10 million page views per month and acquired corporate partnerships for the site and a small staff, she quit her job at Vogue to focus on her own business.

[5] In 2014, Weiss started approaching venture capitalists with ideas for expansion, including a potential Into the Gloss-curated e-commerce platform.

[10] In February 2018, Weiss released that Glossier had successfully raised an additional $52 million in a Series C round of funding.

[11] In March 2019, Weiss announced that Glossier had officially raised $100 million in a Series D round of funding and was valued at $1.2 billion.