My first interaction with Emily Weiss was via email, around 2010 (maybe the beginning of 2011). I didn’t watch The Hills—I gave up on reality TV after The Real World: Las Vegas—but I knew of Emily through fashion. (At the time, she was assisting a stylist named Elissa Santisi, known for wearing good trousers.) I heard Emily was launching some sort of beauty news blog—independent, but more polished than the rest. I want to say that she already had an office at 611 Broadway—one of those shabby-if-serviceable buildings in Soho, on the corner of Houston & Broadway, where the grown children of billionaires would enter to meet with Basil Walter about redoing their five story townhouses—just a couple of floors down from Breaking Media and Fashionista.com, which I was editing at the time.

Fashionista was a teeny site with a teeny budget, and I was desperate to hire a graphic design intern to zhuzh it up, so I posted an advertisement in our job listings section. I didn’t get many bites, but I did get an email from Emily Weiss, introducing herself, and asking if I wouldn’t mind passing along any discarded resumes. She, too, was in need of a graphic design intern for her new, yet-to-be-launched website. Perhaps this says as much about me as it says about Emily, but I sort of couldn’t believe she had the gall to send an email like that. Fashionista classifieds were something like $50 a pop, she could have posted in stealth mode, and what would she see in my rejects that I hadn’t? 

I don’t believe I forwarded her any applications, because from what I remember we got, like, two. But I never forgot that email. Emily was so successful in her early years of entrepreneurship because she wasn’t afraid to ask—whether she was wrangling a celebrity for Into the Gloss’s most popular feature, Top Shelf, or convincing advertisers like Lancôme to buy website banners pre-launch, or raising more than $266 million in funding for Glossier, the beauty line she launched in 2014, with products conceived and formulated based on reader feedback. That gall might have been her greatest asset, and the reason she makes for such a compelling protagonist in the journalist Marisa Meltzer’s new book, Glossy: Ambition, Beauty, and the Inside Story of Emily Weiss’s Glossier.