After graduating from NYU with a degree in studio arts, Weiss worked briefly as a fashion assistant at W Magazine, and later as a styling assistant at Vogue. In 2010, she created the blog, Into The Gloss. Born out of a desire to give an inside look into the beauty routines of celebrities and those in the fashion industry, Into The Gloss represented a more conversational approach to the beauty market. Simultaneously managing her blog and her work at Vogue, Weiss allocated her morning hours, between 4 a.m. and 8 a.m, to the former, and the rest of the day to the latter. Weiss continued to build connections and improve her blog, and it eventually reached 10 million pages view per month. By 2013, the company had raised $2 million in venture capital funding. A year later, in 2014,
Glossier was created.