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It's a Matter of...Performance

The Consummate Creative

August 24, 2021 BeautyMatter
August 24, 2021
FYFE Beauty

The most prolific creatives not only have ideas that many would consider to be “out of the box”but they have the ability to execute on them. The most diligent creatives are also builders turning them into real tangible things - they simply can’t help themselves. They commit an insane amount of time to their work without holding back.

Jillian Dempsey the legendary makeup artist, sculptor, painter, entrepreneur and animal activist shares with Kelly how she is constantly searching for innovative approaches and fresh perspectives to beauty.


[beginning of recorded audio]

Jillian Dempsey [00:00:11]: Hi, I’m Jillian Dempsey, a Los Angeles-based celebrity makeup artist. And to me, it’s a matter of performance.

Kelly Kovack [00:00:22]: Thinker, maker, doer. I’m Kelly Kovack, the Founder of BeautyMatter. The most prolific creatives not only have ideas that many would consider to be out of a box, but they also have the ability to execute on them. The most diligent creatives are also builders, turning them into real, tangible things; they simply can’t help themselves. They commit an insane amount of tiem to their work without holding back. Jillian Demspey, the legendary makeup artist, sculptor, painter, entrepreneur, and animal activist is in a perpetual search of innovative approaches and fresh perspectives to beauty.

So, Jillian, thank you so much for joining us today. I’m super excited for this conversation because I feel like I’ve known of you and your brands for so long and we’ve never met. So thank you for taking the time today.

Jillian Dempsey [00:01:13]: Thank you for having me onboard, it’s been a journey already. 

Kelly Kovack [00:01:18]: I know. So the first line of your bio kind of summed it up for me. You are a prolific creative, legendary makeup artist, sculptor, painter, entrepreneur, animal activist, and it says in constant search of innovative approaches and a fresh perspective to beauty. Can you share how you got your start in the beauty industry? Because you’re one of those people who sort of started at a very young age your passion for beauty.

Jillian Dempsey [00:01:45]: I was selling private label cosmetics in high school and already creating lash oil and cutting hair before I should have been cutting hair. I like change, so I feel like I’m very attracted to balance and scale, as well as color. I’m very interested in oh, what would that look like? It all kind of falls very much into this arena of seeing things outside of a certain way. I don’t think I have the narrow vision. I think see things outside and I like to try them. Maybe it’s a little bit of a risk, I’m a little bit of a risk taker, but in very controlled way. That might sum me up.

Kelly Kovack [00:02:29]: I think even just how you kind of started in the kind of the brand world, so while this is the first time we’re meeting, I used to carry the Deluxe brand, which was your first beauty brand, and also your Jing Jang cream, which still, honestly, like you could sell that today and it would be totally relevant.

Jillian Dempsey [00:02:53]: Honestly, the organic preservative would probably still be fine and smell okay if you opened up today what you purchased back then.

Kelly Kovack [00:03:03]: Yeah, but you know, you were really part of the first indie beauty revolution that happened in kind of the late ‘90s, early ‘00s, and I was working at Bliss at the time and then I went on to launch an advisory shop and Deluxe was kind of – and Jing Jang was kind of our go-to for assortments because it’s when Bobbi Brown and NARS had already sold, so you had to commit to $250,000 of sales, which for an independent retailer, not possible. But you guys were always so easy to work with and it was also so innovative. But reflecting back on what the beauty landscape was kind of at that time, what was the impetus for launching Deluxe?

Jillian Dempsey [00:03:50]: Well, you know, I did have a West Hollywood beauty parlor that was designed to be half makeup and half hair because, let’s face it, I think from that time, I know how to color hair, cut hair, makeup, you kind of had to have everything under your belt in terms of what you could provide as a service. So Deluxe Beauty was an indie brand that I designed along with my sister, Kristin Mason, and we just rolled with it. It all started because the West Hollywood salon had a very retro kind of ‘50s vibe. It didn’t really look like anything from the outside, but once you stepped in, it had four shades of pink, it had black linoleum floors, you might hear Slayer hearing in the background. Or you could in at a time when you’d hear Frank Sinatra. It really was like you’d walk in and it was like, what is going on in this beauty parlor? 

So I designed a line of nail polish that looked a little bit retro; that was the very first product that I launched. And it’s funny because the chemist that I used at the time made a mistake. He designed what was known as Cosmopolitan, which I don’t know if you remember that shade. It was one of the most popular shades, it was kind of a watermelon stain for the nails. And it came in this big paint gallon and I opened it up and I said, what is this watery mess? What is this? But then I started painting it on my nails and then I quickly discovered, this is incredible. This is a topcoat with color. And so in my mind I thought, I love this, but what would I call this? How would I explain what this is? How would I tell the consumer what you are getting? Because everyone needed to know what they are purchasing. And so that’s when I did what I wanted to design at that time. It came in as a mistake and then it was quickly redirected into something that I feel very proud about because it was a mistake that turned into something really clever and useful and popular at the time. Heather Graham, that was one of her favorite shades.

Kelly Kovack [00:06:09]: I love that you took what could have been kind of a disaster for a small business and kind of rolled with it.

Jillian Dempsey [00:06:18]: Yes, absolutely. I feel like a lot of creativity you have to see what others might not see. Like, I count how many clicks, I see how it snaps, I look at the scale. I like to feel the product. I like to know what the product is about. When you launch a product, you really are responsible for that product, especially if your name is on it or you’re associated with it or you have to talk to press about it. And it’s a little bit embarrassing if you know that you have delivered a product that doesn’t make sense. And if you also design a product that everyone else has, it isn’t really innovative in some kind of way. And so I always like to bear in mind, what do I really want to talk about? What is interesting? What have I already seen, been there, done that? And what can be useful, mindful, and operational out there for people? What serves people? And what makes a job easy and what fits into people’s lifestyle?

Kelly Kovack [00:07:21]: And you work sort of as a professional makeup artist and have for a very long time. How does that work sort of…I guess, is it part of your process? Do you play with things? And does sort of innovation come out of kind of needs that you have? Because I know with Deluxe Beauty, one of the things was that you could apply it with your fingers. And I know that’s a big thing for you.

Jillian Dempsey [00:07:44]: It is a big thing for me. I have this love/hate with brushes for some reason. As I mentioned to you before, I love to paint. Whenever I’m using a canvas, like a real canvas to paint, my hands always manage to find their way on to that canvas and they like to mess it up. Because I need to sort of feel it. I need to feel bone structure. I want to feel the balance on your face. Sometimes brushes, especially now, are more sanitary than your hands at times. I have no nails on purpose. I like to keep everything very clean. I like a clean shop. Presentation, sanitation, the whole thing, it hasn’t changed, even though now we’ve entered the land of COVID. Finger-friendly, lazy girl makeup, those are all the little taglines you can hit with me. And really, the honest truth is when you hand someone a product, unless it’s kind of like an easy lip balm, ChapStick, there’s no guarantee that person on the other end will know how to use it. People do not like to read directions. People want to just get the product and know how it operates, and sometimes you just have to get the message across: look, this isn’t complicated at all. We have just really taken out any of the guesswork for you. At least I try to, because I like to be considerate to others and I feel like I don’t want to mess up your world with makeup. I’d like to contribute to making it a better journey. I’d like to contribute to giving you an easier way to apply beauty so that it becomes your friend, not your enemy. And especially not a time-sucker for you.

Kelly Kovack [00:09:37]: No, I mean, I am totally in line with your style of makeup, because I’m much more of a skincare girl. I’m a little bit of a disaster when it comes to makeup. So that whole soft of Instagram contouring, baking, all of that stuff was lost on me. I’m like yeah, it does not compute.

Jillian Dempsey [00:09:57]: There is an audience for everything. It’s entertainment value, really, if you think about it. Because if you have two-plus hours to do your face, congratulations because you’ve really made it. I don’t think that I have that much time to spend on this face every single day. And if you can give me the Cliff Notes and shortcuts to get a version of me, then I’m so excited about that.

Kelly Kovack [00:10:24]: Yeah, I think that’s the world most people live in. So you had a great run with Deluxe Beauty, and once again, you’re sort of at the center of another beauty revolution. Very different this time because I think so much has changed from a technology standpoint, and even sort of what’s possible and what consumers want. But the new line is also distinctly different and it is sort of perfectly in tune with kind of the beauty landscape today. Can you share a little bit about your impetus for launching another brand? And I think you launched it in 2014, so I feel like the industry has evolved even sort of since then. And sort of what your goal was this time around.

Jillian Dempsey [00:11:06]: So there is another Patrick in my life, not my husband, Patrick Mason, and he is my brother-in-law, and we have little nicknames for each other, Ma and Pa, and that was in 2014 – that’s how we sort of started, in a way. I’m addicted to eye liner. That is something that I’m very addicted to. I think if you’re packing an eye liner, you can do just everything with an eye liner, and I’ve always felt that way. That’s why they write songs about eyeliner. Maybe it’s not for everyone, but it is certainly for me. And so having a soft, really smudgy, easy to maneuver eyeliner, if I just get a little smudge of eye liner on, I am so happy. It can blend out into anything. It can add a little definition. It just makes me happy. So I think that I wanted to continue on with my eye liner from Deluxe Beauty days, but in a natural way. 

And I set out to – this time around – to try and really be mindful. I knew I could design an entire line from A to Z, but if I did that, I knew that I could not control and do that well and also I was very aware of seasonal shades and I knew I never would be able to keep up with the larger companies, and nor did I really feel like that was necessary. It’s not always necessary to come up with, like, another red lipstick if it’s another red lipstick. And so if it has a different feeling, a finish, a way that it performs, I’m all in. But if it’s just another red lipstick, okay, I feel like I would want to design a red lipstick that I knew I maybe had three things in the back of my head that would be different from all the rest, and then that would make me excited about the process. Because I have to also, as a designer, I have to feel inspired in order to get other people to feel inspired about my products. And if I don’t believe in my products, then I’m not being honest. And if I’m not being honest with you, then why am I doing it? Why waste my time or anyone’s else’s time for that matter?

Kelly Kovack [00:13:26]: Well, also, I think what’s possible from sort of a clean, natural perspective, especially kind of in the color category, has come such a long way. I remember those early kind of natural color lines and I had a client who launched a color engine, and I was like, it drags, there’s no payoff. She’s like, but it’s natural! And I’m like, who cares? It doesn’t work.

Jillian Dempsey [00:13:53]: Yeah, you don’t have the payoff. Wow, when I designed the lid tints for eyes, I remember I went back and forth. I probably drove Patrick Mason really crazy. I have a very good relationship with the lab and the head chemist and founder there, I’m like, I’m begging you, please think about this like it is espresso. It’s a shot of espresso and we are going to add a little cream and then we want to have the mass tone with a sheer payoff so it’s like a little bit of a wash. And she’s looking at me like, sure, we can do that. I’m like, great. You go back and forth and back and forth and back and forth and you look at all the details, you ask the questions, at least I do, because I want to know what’s in this product, how will it perform, who will this work on, and what’s the best way to get it out there? And the messaging is very important. And if you get it, you get it. If you don’t get it, it’s not right for you and you can buy another line. And I’m fine with that because I don’t know that the lid tint would be anyone’s cup of tea or espresso, but I feel like it really works for my lifestyle, and I can say that even today I do my face with my lid tints and my cheek tints, the whole thing, and my eyeliners, I use my hydrating eye mask, my gold bar, I was trying to use it this morning to just iron out some of my face today. So I think I have a really nice range that’s useful. And again, I feel like I like to design in a creative way that makes sense for the customer and is really service-based, because that’s what I do for a living. When I show up to a job, that’s what I’m doing. I am there to perform a job. 

You don’t know if the person sitting in your chair just came back from a tropical vacation and has a sunburn, which we all know as makeup artists, it’s the kiss of death. It’s the hardest thing to cover. You can’t apply any makeup to it. It’s really challenging. You have to think really quick how you will get that person to set and impress the client and make the client feel amazing and get the person on set so that the team that you’re – whatever you’re shooting that day is happy with your role as the makeup artist. That’s a lot of pressure, especially when you arrive and you don’t know what you’re going to get for the day.

Kelly Kovack [00:16:38]: Thinkers. Innovators. Experts. Generating ideas for the business of beauty. BeautyMatter has built its reputation as a must-ead resource for beauty industry insiders, delivering future-focused insights and actionable solutions. With the speed of innovation and increased competition in the category, access to the right analysis and intelligence is more critical than ever. Make an investment in yourself and unlock a competitive edge with a subscription to BeautyMatter. Head over to to check out our content. And as a listener to our podcast, use the code UNLOCK25 for a 25% discount.

I’m curious your perspective of how kind of the role of the makeup artist, or you could even say the hair stylist, in this day of Instagram and influencers, a lot of these artists are kind of celebrities in their own right, where before, the artists were kind of in the background. Like, have you seen a difference in I guess not even in the role or just the makeup of kind of the professional landscape?

Jillian Dempsey [00:17:56]: I mean, I have a few different thoughts about the industry. At the moment, I think due to the circumstances, it’s really forced a lot of makeup artists who were once traveling extensively and working on whether it’s shows, magazine covers, traveling doing press junkets, globally they’re on different time zones, they are working, working, working. And they don’t have all of that time to necessarily devote to an Instagram page. So their numbers could be down, but at the same time, that’s an incredible artist right there. And I say artist because I truly mean the word artist. A lot of the industry players that work very hard have worked with their craft, whether it’s in hair, makeup, nails, hair color, they sometimes now have to take this backseat. And if you complain about it, then you are considered to be, like, well, the other people are doing something right? They are doing their face and they’re showing you and they’re telling you their opinion, and I think that’s one way to look at in a positive way. There is an audience and there’s something for everyone. But the industry people who do the work behind the scenes like myself, we tend to be a little more camera shy. We tend to not be as great working on our own face because we are so engaged trying to figure out the other face and the other formulas, techniques, balancing, and I am always trying to find the scale of brows and figure out, like, what the hairstylist is doing and what the client is wearing and how are we all collaborating? There’s so many different work families out there. 

In fact, Kelly, I really wanted to talk about agencies that represent hair and makeup and the beauty field in general. I think that that’s an important thing for people to really know. I don’t think enough people know that we’re represented by agencies that actually take a phone call on our behalf and they organize and orchestrate all of where we are to arrive and the call times, the call sheets. I feel like sometimes when I say, oh no, I can’t be there tomorrow, my call time on my call sheet, people are like, what are you talking about right now? So that’s an education right there. I have been with an agency since I was around in my early, early 20s. I did a lot of my early days in London. I spent a year there developing my book, which is now – we don’t do books anymore, we don’t do portfolios other than maybe a scroll on Instagram that might be your new portfolio for some people. It’s important for people to understand that agencies book that talent and the talent are the industry players, and the industry players are the people who service – getting back to that work, service the talent, and the talent would be the actress, the singer, the actor. There’s men’s grooming. There’s an endless line, and the difference between an agency and say someone who works on movies, that’s a union, there’s a huge difference there. And I don’t think enough people are really aware of the agencies and the industry people, and that’s why I wanted to quickly get – and I say quickly four years in, my app, Fyfe Beauty, I wanted to get the app up in order to focus on the industry players.

Kelly Kovack [00:21:46]: Can we just back up, Jillian, and can you share a little bit about the app? Because, you know, it’s interesting, I read about it and then I went onto it and I was like, oh wow, this more than an app. It’s actually kind of content and community and consumer-facing and professional. It’s really quite fascinating.

Jillian Dempsey [00:22:03]: Well, can I just tell you thank you very much for the compliment, but it has been quite the ride for me. Every day I get up and if I’m not freelancing, which I haven’t been lately that much, but I am full on Fyfe. I live a Fyfe life. I also design my products. I work off of my gut feeling and I started off with a little sketchbook of, like, a rough idea of little drawings of how I could bring beauty and technology together in order to provide a service for people. Almost as if – you know, there isn’t a really cool beauty and grooming app that you can just click into and go on and capture an essence of something. You might learn something from the app, you might be able to study the technique or the hand or even build the confidence to work something out on your face in the privacy of your home, and no one’s watching and no one cares and no one knows where you have been on the app. And for me, it’s just a beauty playground. I don’t really have any ideas of moving it into every different department, that’s confusing, and I like to stick in my beauty lane. But the beauty lane is huge because we just launched 20 men’s grooming tutorials. We have nails, as you probably have seen. We have a colorist on board. We have hair dressers and makeup artists and we haven’t even started to cover all of the turf. And we’ve only been able to do the west coast because of COVID, but I think that this is a really nice and comfortable platform for the industry players and you know, I’m not alienating other people. It’s just if you can work on a face and you know your way around a face or hair or whatever it is you’ve spent the last however many years on crafting, jump on board because it’s exciting. I even learned things. Tracy Cunningham, I often go on the app to refer to like, wait, she uses ten-volume to cover gray hair? I always thought you used 40-volume because you wanted to expand the cuticle and have the depositing time and you leave it on for over an hour, but no. Tracy Cunningham says ten-volume, always, to cover gray hair. My 40-volume went out the window.

Kelly Kovack [00:24:31]: It is interesting because makeup, hair, skin, it is a craft. Like, you can’t come out of school and sort of be a master. It happens with age and with sort of the more people you touch and it evolves and someone else that we had on the show who is a friend of mine is Matin Maulawizada, but we had the same conversation where some of these true artists, they’re busy working and don’t have time to create content for an Instagram feed, but yet in my mind are true influencers because true influencers are experts.

Jillian Dempsey [00:25:10]: That’s right. If you have a lot of time to build Instagram, you’re not probably spending a lot of time doing the craft.

Kelly Kovack [00:25:17]: I mean, listen, there’s a place for that, but I love what you’re building because it’s sort of from an industry perspective and it’s such a wonderful way for people who have sort of honed their craft to sort of pass that knowledge along in a way that’s scalable.

Jillian Dempsey [00:25:37]: Yes, the capturing the essence of the artist, to me, and the storytelling and understanding, where did you learn to draw that line? Like, which way – my eyeliner stroke may be going out, Kate Lee, she may bring her stroke in, in terms of the liner. We have different styles. We may use the same product, and we might use it in two different ways. That’s so interesting for me, and also I think other beauty enthusiasts to look at, and even for if you are wanting to enter into the business and the industry to see the hands of others who have done this and it wasn’t brand new, there’s something to that and there’s also something to the newer way of doing things as well. Like, the gen z – one of my kids does makeup and thinks he’s better than me. That’s okay. He thinks his eyeliner is better than mine. It could be, I don’t know. But the point is – we might have a Karen moment there. 

Kelly Kovack [00:26:42]: You can decide later.

Jillian Dempsey [00:26:44]: We’ll decide later. I just think that I like to stay open-minded and I like to listen to the team around me and then pull everything in and then make the best decisions from there. And I think that other industry people really relate to me because they’ve seen me on jobs. They’ve seen me around. We’ve all been in those press junket hallways together, we’ve all been jetlagged together, you have little work families you’ve traveled with, you’ve shared experiences with, and there’s a lovely part of that story that has been my entire life. And so sharing that and bringing some people who are industry players that maybe haven’t had the opportunity to share their story or to actually capture a little bit of their art, that is so incredible to have and to learn and to observe and just to be able to quickly access, too. People, like let’s face it. You may not want to visit an app unless there’s something in it for you. If there is something that you might feel compelled either that you need or you want or you’re interested in, it’s sort of like eh, why bother? I don’t need to go there. That’s why I like to throw curve balls. You just never know what you’re going to see on the app, but it will be something very interesting in beauty and we are cooking so much up over here. Just wait.

Kelly Kovack [00:28:24]: Now I am totally hooked on it. I love conversations with sort of true creatives, and you seem to be so prolific. Like, where do you get your inspiration? And do you ever get stuck? And in those moments, how do you get unstuck?

Jillian Dempsey [00:28:38]: Do I get stuck? Yes! And it’s frustrating. I have to remind myself that everyone goes through that land of feeling insecurity and feeling am I on the right path? Is this going somewhere? Am I making the right decisions every single day? What is driving me every single day of my life? And I could honestly tell you, and Patrick could tell you, I’ve never stopped working, never ever. And I think that the drive behind it is because I actually enjoy it, I love it, and I push right through just to get to where the sweet spot is. In terms of like, designing products, I have two projects which I can’t really talk about right now because Patrick might murder me, but I haven’t put them out into the marketplace because they require a little more messaging and I want the formula to be perfect, and I want not only for the formula to be perfect, but I want the convenience of it to be perfect. If I design something and I feel like this is new and innovative, if I give you something, Kelly, and you have one go at it and you’re frustrated, chances are, you’re never going to pick that up again.

Kelly Kovack [00:29:59]: Yeah, it doesn’t matter how innovative it is.

Jillian Dempsey [00:30:01]: That’s right. I want to get in front of that and I want to be – I’m Kelly, I’m opening my product right now, and I’m thinking, okay Kelly, if I’m not there to instruct you, maybe you could check it out on the app, sure. If I’m not there to instruct you, will it be a visual for you to understand exactly what I want you to do with this product in order to get the results?

Kelly Kovack [00:30:27]: And everyone learns differently, too.

Jillian Dempsey [00:30:30]: That’s right, and people feel more confident if they are told by a professional yes, I am bossy, this is the color for you. Yes, you need to wear this. This is for you. And I like to build the confidence in people to know that what you can expect is for you and not something that we’ve just phoned in and stamped a label on. I’ve really worked it out in a way that maybe you might not be interested in it or it’s not your color or it’s not the way you applied your makeup, but it is designed for a certain type of person and for a certain method of application. Does that makes sense?

Kelly Kovack [00:31:13]: That makes absolute sense. It’s sort of this clarity that it’s impossible to create products for everyone. And it’s really, I think – I mean, maybe you realize it or not, but it is that sort of very laser-focus of the intent of who the product is for and being okay with the fact that it’s not for everyone.

Jillian Dempsey [00:31:35]: Right. And I try not to be defensive about it because you can become very protective of the products you’ve designed if you truly have made that product. Sometimes if people complain about things you take it really personally and you’re like whoa, wait a minute, are you applying this properly? Oh, oh, well that’s different, you’re applying a primer that has a bunch of, like, gumminess to it beneath the lid tint? That’s not going to work out for you at all because I didn’t design that product and I can’t guarantee the results that you will arrive at after you’ve applied the lid tint. It’s a swipe, it’s a smudge, it’s an on-the-go, it’s an in-your-car, on whatever transportation you’re taking, on your walk, on your mask. It is however you’d like to incorporate it, but it’s meant to make your life a little easier.

Kelly Kovack [00:32:29]: Well, Jillian, I hope this isn’t the last conversation, it may be the first, but this has been so much fun.

Jillian Dempsey [00:32:36]: I’m very shy because I don’t – you never know what’s going to come out of here sometimes.

Kelly Kovack [00:32:41]: Well, this was fun. So thank you so much for sharing and taking the time today.

Jillian Dempsey [00:32:46]: Thank you, Kelly. Thank you for having me.

Kelly Kovack [00:32:53]: For Jillian, it’s a matter of performance. She has been working in the beauty industry her entire career. She started in high school and has never stopped, nor has her curiosity or excitement. She has perfected her craft, working behind the scenes for celebrities and editorial work for over two decades. She’s equal parts creative and savvy entrepreneur with an innate ability to be ahead of the beauty curve, making her the ultimate beauty expert. In addition to her namesake brand, she’s tapped into her collaborative spirit of knowledge sharing with a new virtual consultation app called Fyfe Beauty. Jillian’s love for beauty and excitement for what the future has in store is infectious. She may be an industry veteran, but she’s got big plans and she’s just getting started. So in the end, it’s a matter of performance, and that’s what matters. I’m Kelly Kovac, see you next time.

Jillian Dempsey [00:33:52]: Hi, I’m Jillian Dempsey, and to me what matters is performance. Ease of use and full transparency.

Kelly Kovack [00:34:02]: It’s A Matter Of is a production of BeautyMatter LLC. You can find more content and insights on and follow us on social media @BeautyMatterOfficial.



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