Once back, she hit the ground running, teaming up with The 88, a self-described “bespoke creative agency” founded by downtown gadabout Harry Bee. There she learned the power of digital marketing while single-handedly managing The 88’s off-kilter brands. And of course, she threw killer parties.
In January, the same month she was named one of The New York Post’s “13 under 30” “It girls,” Ms. Reising broke off from The 88 and started Sydney Reising Creative. (She claims the split was amicable, despite taking most of the clients with her.) The timing was impeccable: weeks later, at Fashion Week, she scored a bona fide coup at the relatively small show by her client Hood by Air, a fashion line by Shayne Oliver. At the show, A$AP Rocky walked out for the final look. The spectacle dominated the fickle fashion world’s chatter for days.
“With Sydney, it’s a fam thing—we met and it was an instant ‘getting each other’ moment,” Mr. Oliver told The Observer. “She works with Rocky, I work with Rocky, so it was a perfect fit.”
Ms. Reising is rarely not working. Even her domestic life, which is supposed to exist in an aging building on Houston Street and Avenue D, features all the types she would represent or invite to her parties. A mutual friend dubbed it “The Hipster Melrose Place.” Former MTV kid Gideon Yago, Cobrasnake muse Cory Kennedy, fashionista filmmaker Crystal Moselle and a revolving cast of skateboarders, graffitists and artists have all spent time there, living a bohemian life on the last gritty edge of the East Village.
“I found that apartment on Craigslist,” she said, “and when I moved in, I realized I knew everybody.”
Ms. Reising lives alone—with her dog, Ruby, a constant presence on her Tumblr and her Twitter feed—and she’s decorated the place mostly with work-related material: a “Cuntier” (picture that word in the Cartier font) hat above a bookshelf, laminated press passes hanging from doorknobs, fliers from old parties. But there is also a talisman or two from her past, like the collage of cut-out pictures of friends from home, arranged as it might have been in the dorm room she never had.
“I have no regrets about not going to college,” she said. “Most of my clients didn’t, either.”
Throughout our conversation, Ms. Reising kept dabbing at her phone, which beeped nonstop with pop-up notifications. There were likes on Facebook, at-replies on Twitter, comments on Instagram, emails and texts from clients, calendar reminders and constant updates from her assistant.
“A lot of my business comes from Instagram,” she said. “People find me through social media. Every new business meeting I have, they say, ‘We’ve been watching you online.’ I like what I do; I’m proud of everything that I do, so if there’s a press clip, I Instagram it. Writers, they’ll send me their clip and say, ‘Sydney, Instagram it!’”
“But I do send my handwritten thank-you cards, too.”
A few days later, The Observer showed up an hour late for Ms. Reising’s party at the Armani flagship, celebrating a collaboration between Ben Pundole, the founder of travel startup A Hotel Life, and GQ. But the head of SRC was nowhere to be found.
“Lol I’m en route,” Ms. Reising texted. When she arrived, she announced with a sigh that she had been sleeping all day—the previous night had been devoted to announcing her latest venture, a collaboration between Scion A/V, the music collective under the umbrella of Toyota’s Scion line of cars, and Hood by Air, to be unveiled a week later in Los Angeles.
In the following days, Ms. Reising’s fingerprints were popping up seemingly wherever we went. At the Boom Boom Room, a young man who worked for VFiles, the YouTube channel-turned-boutique in Soho, was wearing a #BEEN #TRILL snapback collaboration with the brand 40oz. (“Very rare!” Ms. Reising said when we texted her.) Miley Cyrus posted on Instagram a photo of her mock-Cartier “Cuntier” hat, which Ms. Reising originally publicized. Drake posted pictures on Instagram, to his two million followers, of Polaroid pictures depicting him wearing Hood by Air. Cara Delevingne, the model anointed to be the next Kate Moss, wore ear cuffs by Genevieve Jones—a SRC client—to the Costume Institute Gala. Another client, male model Naleye Junior, deejayed a Met Ball after-party. The musician Grimes wore an octagonal pair of Cast Eyewear sunglasses to the Webby Awards. And so on.
The last time we saw Ms. Reising was at a cocktail party she hosted at ØDD, a boutique founded by 21-year-old designer and stylist Judson Harmon. Ms. Reising was standing in the back, her phone in the air, taking a video that she would post on the social network Vine.
“I’m still working on my Vine game,” she admitted.
After a couple glasses of bubbly, we left, and though we would not see Ms. Reising later that night, we did see her on our phone while watching her Vine video—swirling images of Mr. Harmon, of the champagne, of the punishing leather booths, of the security-camera feed, of another phone, of her hair and of the ØDD logo. On our phone, it kept playing, a recursive loop, over and over again.