Hollywood Knows Who Cassandra Grey Is. Do You?

From ELLE

Cassandra Grey is a curator. She curates spaces, people and, most influentially, the luxury beauty store Violet Grey. Online and on Melrose Place, Violet Grey sells only products that are beloved by celebrities and their makeup artists, stringently edited in accordance with Grey’s own beauty philosophy: less but better.

Grey, who started the company in 2013, recently edited down her own belongings. She was preparing to move into her new home, a classic Los Angeles modernist glass cube designed by Richard Neutra. The new house is all air and light, perched on a hillside in a remote canyon and overlooking an aqua blue swimming pool and the Hollywood hills. It doesn’t require much in the way of furnishings. Among the items that made the cut: a Christopher Wool word painting, a large photo of Jackie Kennedy and her second husband Aristotle Onassis, and a rug designed by Virgil Abloh’s Off-White that says “GREY,” a gift from her girlfriend, DJ Samantha Ronson.

When I meet Grey there in November, she greets me at the door wearing leopard print leggings and a ripped black t-shirt with sneakers. Her black hair is in a pixie cut, and her doe-eyed face is bare except for black eyeliner and mascara, giving her the air of a goth Audrey Hepburn.

Grey, 41, has been busy expanding her beauty empire, most recently, introducing the world to The Cream, a $265 moisturizer from German dermatologist Augustinus Bader. Melanie Griffith turned Grey onto The Cream; Violet Grey started stocking The Cream; The Cream achieved cult status.

At the same time, Grey has also been undergoing a private recalibration. It’s been nearly two years since the death of Grey’s husband, Hollywood mogul Brad Grey. The couple lived on the Westside, on Frank Sinatra’s former property, and were married there in 2011 with stars like Brad Pitt, Jennifer Lopez, and then couple Tom Cruise and Katie Holmes in attendance. The house was demolished to make way for The Grey Estate, a rambling 12-bathroom mansion Grey sold in May for around $68 M.

“I [was] basically like the CEO of my house,” Grey says of her life then. Not that she’s complaining, but it felt like running a hotel, or a overseeing military operation. There was a stretch of years in which she never pumped gas, went to the ATM, or did the dishes. In her new life, Grey has eschewed a staff in favor of a single assistant.

Just a few months into her new, pared-down, canyon surroundings, does she feel settled?

“Kind of,” Grey says. Moving to a new house in a new part of town makes her feel settled in the sense that things feel different. “I have a lot to do here, but it feels like…”

A new chapter?

“Yeah, definitely.”

The daughter of a hippy and a former hippy who divorced when she was a baby, Grey grew up in San Francisco with her father and all over the country with her “free-spirited” mom. Her first meaningful job was at a children’s clothing store, where she learned “the buying and the books and the sales and the windows.” Grey quickly made a name for herself as a branding expert, first for San Francisco realtors during the 90s tech boom, and then in New York, where she threw in-store events for a hip lingerie line and was asked to “curate cool people” for the Norwood Club on 14th Street.

She came up with the idea for Violet Grey one night in New York, and wrote out a seven-page business plan. “As somebody who is obsessed with human behavior and emotional connectivity, there’s just so much to work with [in beauty],” she says. “There’s self-esteem and sexuality and power and vulnerability.” She imagined the company would be a shopping platform with a personal touch. Today, it’s the beauty world equivalent of Net-a-Porter: top shelf products alongside chicly art directed celebrity profiles.

But first, she met Brad Grey, in a romantic scenario right out of a Hollywood movie. At a dinner party in Los Angeles, she recalls, “He noticed me. I noticed him.” The executive who had a hand in The Departed and Transformers was twenty years older than she and had three kids. Cassandra had a boyfriend, and nothing happened that night. “Then he started pursuing me, relentlessly.” Once the two started spending time together, she says, it was an “inseparable, kind of really big love affair.” She had never dated an older man or someone with children, but the biggest deterrent was that he lived in Los Angeles. “I didn’t want to be with someone from Los Angeles. Coming from San Francisco you have this misconception of Los Angeles. Now I love it.”

Grey’s assimilation to Hollywood wasn’t painless. “I think at the beginning, when we were first together” Grey says, some people saw her as “a gold-digging whore.” She didn’t see her relationship that way, but she was accustomed to feeling misunderstood. She weathered a minor scandal in 2012, when the Los Angeles Times reported that Hollywood executives were passing around an Italian Vogue video of Grey, channeling Marlene Dietrich with a head wrap and cigarette, holding forth about life and style (title: “The Princess of Bel Air”). With characteristic good humor, Grey told the Times that the attempt at self-parody had flopped: “I am proud of the work that I do behind the scenes, which is where I belong.”

Talking about that time now, Grey is sensitive about the threat relationships like hers and Brad’s represented. “It’s a cliché and it’s a cliché for a reason,” she says. She credits a group of older “ladies of Hollywood” for making her feel welcome. “They really embraced me,” she says. “They could see that I was a unique, individual, independent person.” Some credit must also go to Grey’s work ethic. From her perch among Hollywood royalty, Grey became obsessed with the people backstage: “Make-up artists, hair stylists, and stylists. All the people who are behind image.” She closely studied the red carpet, “the whole racket and business transactional part of it.” She correctly predicted celebrity makeup artists would be the next celebrity chefs, and tapped them to make Violet Grey “the gold standard for product recommendation.” “I worked like crazy,” she says, eventually raising Violet Grey’s $2 M seed round of funding in 2013. “It was kind of hard to label me as the trophy wife.”

One young lady of Hollywood, Lorraine Nicholson, met Grey through the late super-agent Sue Mengers. “Before I met Cassandra, she was a legend in my mind,” Nicholson writes in an email. “She was the person who had bedazzled Sue Menger's call button that she used to summon her maids.” The real Cassandra lived up to the legend, she says. “There's something about Cassandra that is at once completely sure of how the world should both look and work, while at the same time being open to collaboration and new ideas. She is mysterious and straightforward, elegant yet down to earth all at once. For me, it's Cassandra's contradictions that make her such a magnetic person and friend.”

April Uchitel, the CEO of Violet Grey also describes Cassandra’s effect on people in near-mystical terms. “We like to say Cassandra can bend reality to her will, but in a really great way because she's so inspiring.” How exactly does Grey bend spoons with her mind? “I mean, she's incredibly charming,” Uchitel says. “She is self-effacing in a way that you wouldn't expect. I think when you look at people who have built things, and put themselves as a face in front of those things, usually there's a guard and there's a certain persona you're trying to project at all times.” Grey, she says, is “very intuitive. I mean, she sees it.”

While Cassandra was building Violet Grey, Brad was diagnosed with metastatic lung cancer. Many patients with his diagnosis die within six months, Grey said; her husband lived five and a half more years. “When you’re living in it you don’t really realize how intense it is,” Grey says. “Kind of like how when you’re living in New York you don’t really realize that there’s 100,000 people on the street corner you’re standing on.” The couple had launched into marriage and then, during his illness, her start-up, home-building, pregnancy and child-rearing. Adding to the surreality, she says, Brad did not seem visibly sick. “We had incredible doctors, so it wasn’t really watching him suffer until the end, which was just the worst, other than suffering yourself, watching someone you love suffer is just horrific.” She made “zero plans” about facing life after the death of her husband. “It’s so weird because we never actually discussed death. I never actually thought he would die.”

When her husband died, Grey took about a month off from work. She was relieved to realize the team she had built at Violet Grey could function without her, and she came out of the other side of grief with a fairly bright outlook. “First of all, I feel him,” she says. “I can say with 100 percent certainty that we don’t just die. I’ve had a spiritual awakening where I feel very differently about death. I don’t look at it as negatively anymore. I’m not scared of it anymore. I don’t feel such an urgency to life. A lot of it is out of our control. We’re meant to just be experiencing and learning.” Her son, Jules, 3, kept her from fully sinking into depression. So did a team of healers: “shrinks, and AA and grief counseling. And astrology, I had never done astrology before, I’m very into astrology now. Psychics.”

The front door opens and Grey’s friend Carole Radziwill, the veteran journalist and former Real Housewives of New York City cast member enters. “I’ve known Cassandra since she was just a puppy,” she says, joining us on the couch.

The two women met over a decade ago in New York, where Grey pursued Radziwill as a friend, inviting her to poker nights. “I thought that was cool and thought it would make her think I’m cool.” A recovering alcoholic, Grey says she was “definitely a party girl” in those years. Radziwill herself was recently widowed and needed “young, fun girlfriends to pal around with.”

“You never had that time in your 20s when you’re dancing and making out and stuff,” Grey says.

“I made up for it though,” Radziwill says. “From the time I was 35 to 45.”

Grey no longer parties, but she first met her girlfriend Samantha Ronson at one. Six years ago, Grey hired Ronson to perform at Brad’s 55th birthday party. The attraction was instantaneous, Grey says, likening the moment to a high schooler meeting Justin Bieber. “I had never really been attracted to a girl like that… So much so that I told my husband. ‘I think I have a crush on this girl.’ He was like, ‘Well maybe you shouldn’t hang out with her.’”

“Brad was cool with it,” Radziwill says.

Grey didn’t see Ronson again until after Brad’s death. Still “super isolated and depressed and dark,” she had gotten in the habit of putting her son to bed at seven and then going to bed herself. Her shrink told her she had to get out of bed and leave the house, and a friend dragged her to a Make-A-Wish Foundation gala. She was uncomfortable, and then she saw Ronson. “I wasn’t attracted to her the way I was when I first met her. I wasn’t in that zone at all. First of all I didn’t even recognize her. I thought she was her sister or something because her hair was long. And then we started talking but it felt very familiar, just cool.” They bonded over their shared sobriety, stayed in touch, and started hanging out. “It just switched, in one moment, and now I’m in love with her...It feels like the part when I was falling in love with [Brad]....I fell so hard for him, that I just didn’t think it would ever happen again.” She is grateful she listened to her shrink and left the house to go to the party that night, although her astrologer probably wouldn’t discount the impact of the stars.

In a town where green light authority is social currency, it’s hard to deny that Grey’s life has changed since she has been widowed. But to hear it from Grey, it’s all part of a larger plan to do less. “There’s not as much ass-kissing as there was before,” Grey says. “If something happened in our lives, there would be like 15,000 gifts that arrived… now there’s like five.” But that’s 14,995 fewer things to find a place for in her new home, and 14,9995 fewer thank you notes to write. Though Grey admits she still doesn’t pump gas. “I actually have a Tesla,” she says, “so I don’t.”

('You Might Also Like',)

• 10 Pairs of White Sneakers That Go With Everything

• 50 Surprising Things You Never Knew About 'Sex and the City'

• 20 Serums to Solve All Your Skincare Problems