Weiss moved to New York at 18 to study at New York University, majoring in studio art. It was at this point that she made her first foray into the fashion and beauty realm by taking up a three-day-a-week internship at Teen Vogue during her studies.
After graduating in 2007, Weiss worked briefly for W magazine before moving to Vogue, where she worked as a fashion assistant.
While working as a fashion assistant, Weiss set up her beauty blog, Into The Gloss, spotting a gap in the market for beauty product coverage.
“I was surrounded by so much magic … All these models and makeup [artists],” she said in an interview with Fashionista in 2015.
“That was the inspiration for Into the Gloss, wanting to know more about these women who were so cool and interesting for all these different reasons.”