VIOLET GREY profiles female beauty entrepreneurs who are considered industry game changers for their individual approach to business. Each one entered the conversation in her own manner and maintained a steady, if not unparalleled, trajectory with her indomitable spirit. Here, we talk to Jillian Dempsey, the makeup artist and founder of her eponymous all-natural color line.

Known for her down-to-earth, forthright personality (don’t be surprised if she suggests you need a brow tweeze), makeup artist Jillian Dempsey has earned her stripes when it comes to painting the faces of Hollywood’s elite (including Jennifer Lawrence, Kristen Stewart, and Kirsten Dunst). Her passion for maquillage dates back to childhood, when she applied makeup to her dolls. And then, “In high school I sold a private label brand of makeup to my friends and their mothers,” Dempsey says. “I practiced on anyone I could get my hands on.” In 1988, Dempsey, an LA native, attended The Charles Ross School of Beauty in southern California. Back then she had to excel at both hair and makeup. “I know how to cut, style, and color hair,” says Dempsey. “You would lose work unless you knew how to do both. But in the mid-nineties I had to decide whether I wanted to go into the hair or makeup department.”

Ultimately, makeup artistry was her passion, and her talent landed her in the big leagues, working with photographers like Mario Testino and Julian Broad. “I was in Paris, staying with Milla Jovovich and her manager, Chris, and they were able to put me on some jobs,” says Dempsey. “I wasn’t even an assistant. I would go on what they called a ‘go-see.’ I would show whatever imagery I had to photographers, meet with them, and I would get jobs.”

She moved to back to Los Angeles, signed with Smashbox Studios, and landed her big break in 1993, when she did Brooke Shields’ makeup for a double-page spread in Vanity Fair. “I developed a relationship with Vanity Fair and started doing covers with Annie Leibovitz,” she recalls. “I remember doing a Johnny Depp cover in 1999, and I did some of the Hollywood Women covers way back when. I also met Drew Barrymore at a Vanity Fair shoot, and she and I became fast friends. I worked with her and traveled all over the world with her for seven or eight years.”

Dempsey’s latest endeavor is her flourishing namesake makeup brand, which comprises lid tints and kohl eyeliner. When conceiving her smudgy lid tints, Dempsey drew inspiration from longtime client Kristen Stewart and her cool-girl style (think: T-shirt, bedhead hair, and dark eyes). The sheer, all-natural grape-seed oil–based tints have a balmy consistency and instantly deliver a uniquely smooth, glossy wash of color whether applied with fingers or an eyeshadow brush. “I wanted to make something that everyone would know how to use without an instruction pamphlet,” says Dempsey. “I think eyes should look lived in, like a watercolor. The color should complement your face. I like to make what I want to use on my clients and what is not typical to the marketplace. I go for what I feel is authentic: easy, mistake-proof, finger-friendly, and as natural and organic as possible.”

JILLIAN BEFORE 10AM

BEDROOM

What is the atmosphere of your bedroom?
Tranquil, but sometimes dominated by our 10-year-old twin boys!

Please describe your bed and your favorite thing about it.
It’s a custom Beautyrest mattress created with the intention of kids jumping into it, so it’s massive.

What time do you wake up?
6:37 a.m.

How many hours of sleep do you require?
Seven, but I’d love more.

Any bedside beauty essentials?
Nuxe Honey lip balm and Susanne Kaufmann hand lotion.

BODY

Do you drink coffee or tea, eat breakfast?
Typically coffee, but certain days I love PG Tips black tea. Breakfast always varies, but it’s healthy and light. I like a little yogurt, granola, goji berries, and blueberries. My 15-year-old daughter, Talula, makes delicious breakfast recipes.

Do you work out in the a.m.?
If I’m not on a job, then yes, absolutely. I like to rotate between SoulCycle, Gloveworx Boxing, and Pure Barre. I typically take my kids to school first, then exercise.

BEAUTY

What is your morning skincare regimen?
I wash my face using iS Clinical Cleansing Complex or JK 7 Foaming Face Wash in patchouli & ylang ylang. Then I apply Dr. Barbara Sturm hyaluronic acid ampoules and tap around my eye area for hydration, followed by Dr. Barbara Sturm face cream. I let this soak in, and then I add SPF, which varies, but I use EltaMD SPF broad spectrum often. What makeup and products do you use on a daily basis? I have to get out the door fast each day, so I like easy, effortless makeup. I use Jung Saem Mool concealer palette under my eyes and to spot cover any redness. For eyelid tint, my organic formula has a light hint of color that illuminates my lids. I choose one of the six shades and swipe it on. Sometimes I smudge it with a layer of my Rich Brown khôl eyeliner. Typically I can do most of my makeup with finger application. I also use Laura Mercier Crème Cheek Colour in Canyon, Troy Surratt Blonde eyebrow rechargeable pencil, Koji eyelash curler, and Chanel Le Volume Noir or Shiseido water-resistant black mascara.

What’s your hair situation in the a.m.?
I don’t do anything but brush it and twist in some Oribe Crème. My hair is super low maintenance, aside from getting color with Tracey Cunningham.

BUSINESS

What’s the first thing you read each morning?
NPR news app for top stories, then emails and Instagram.

What business do you conduct before 10:00 a.m.?
It’s different every day, so that would be hard to define, but I’m always working on developing my product line and constantly testing out all categories of makeup and skincare.

What time do you head to your office?
I live in it—it has four wheels.