Leap Academy with Ilana Golan - The Powerhouse Behind MAC, Tom Ford Beauty & More: John Demsey’s Untold Career Lessons | E136

Episode Date: December 2, 2025

John Demsey didn’t become a powerhouse in the beauty industry by a mere stroke of luck; he built that influence on retail floors, taking on scrappy roles while learning the business in ways no MBA could ever teach. This helped him scale MAC Cosmetics into a global cultural movement, shape some of the most iconic beauty brands of our time, and ultimately rise to Group President of Estée Lauder Companies. In this episode, John joins Ilana to reveal how to build a career from the ground up, reinvent after setbacks, and lead with the kind of creativity that transforms industries. John D. Demsey is the former Executive Group President of Estée Lauder Companies, where he helped build and scale iconic brands like MAC Cosmetics, Tom Ford Beauty, and more into a multi-billion-dollar global powerhouse. In this episode, Ilana and John will discuss: (00:00) Introduction  (02:38) His Early Exposure to Fashion and Design (06:36) Choosing Stanford Over the Ivy Leagues (09:26) Getting Started in the Beauty Industry (15:35) The Power of Learning Every Role in the Business (24:11) Joining Estee Lauder and Moving to LA (28:42) Building MAC Cosmetics into a Global Powerhouse  (36:02) How John Landed Celebrity Endorsements (42:56) Working with Tom Ford and Revolutionizing Fragrances (52:58) Navigating Controversy and Reinventing Himself (1:01:17) His New Ventures and Future Plans John D. Demsey is the former Executive Group President of Estée Lauder Companies, where he helped build and scale iconic brands like MAC Cosmetics, Tom Ford Beauty, Smashbox, Clinique, and Jo Malone London. Over his 30-year career at Estée Lauder, he played a pivotal role in expanding the company into a multi-billion-dollar business across both established and emerging markets. He is the author of Behind the Blue Door, a visual memoir capturing his bold lifestyle, vibrant career, and personal journey. Connect with John: John’s Instagram: instagram.com/jdemsey  John’s LinkedIn: linkedin.com/in/john-demsey  Resources Mentioned: John’s Book, Behind the Blue Door: A Maximalist Mantra: https://www.amazon.com/dp/0865654344  LEAP E57 with Dan Ariely: https://podcasts.apple.com/us/podcast/surviving-lies-rumors-and-digital-hate-dan-arielys/id1701718200?i=1000678512628  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

Wow, this show is going to be incredible. So buckle up, and I'm sure you're going to enjoy it. But before we get started, I want to ask you for a favor. See, it's really, really important for me to help millions of people elevate their career, fast-track to leadership, land dream rules, jump to entrepreneurship, or create portfolio careers. And this podcast is all about enabling this for millions of people to see a map of what it actually takes for big leaders to reach success. So subscribe and download.

ever miss it. Plus, it really, really helps me continue to bring amazing guests. Okay, so let's dive in. I didn't want a life just to do a job. I wanted a life that I could change things, shift the culture, shift the narrative. And I'm still very lucky, but I'm still able to do it. John Dempsey is the former executive group president of Esty Lauder companies where he built and scale some of the world's most iconic brands, including Mac cosmetics and Tom Ford Beauty. My personal story is all about leaps. I was working in a lot of jobs being people's number two for 15 years. I was not an overnight sensation.

I took Matt from a niche indie beauty brand to what its high watermark was the largest color cosmetic brand in the world. When you run something so big, there's usually some very hard challenge that come with it. I had two challenges. First of all, the large corporations, of the world that were used to the more mass merchandise techniques, they don't work the same way anymore. There's been such an evolution and so much disruption in the beauty business because I wanted to lean in because I want us to hear what does it actually take to lead and grow a multi-billion dollar beauty giant.

John Dempsey is the former executive group president of Esty Lauder Companies where he built and scale some of the world's most iconic brands, including Mac the Cosmetics and Tom Ford Beauty and Joe Malone. And I actually know my daughter would have loved to be here instead of me. But John is also the author of Behind the Blue Door. a stunning visual memoir. And today we're diving into really the pivotal moment that shaped his journey, the biggest challenges, the most fascinating lessons, and what he's still hungry to create next.

And he's up to some really big things and we're going to announce all of them. So I have to start, first of all, from a funny and fun fact, John. How many dogs did you just say you have? I have 12 dogs and two cats. So 14 animals living in the house, along with a 17-year-old daughter. Who gets more attention?

The daughter or the... You know what? The daughter gets the attention because how we ended up with the dogs. Good answer. So, John, I want to take you back in time because I want us to start understanding who is John and how does John grow up in tiny Ohio, if you will, not in L.A., not in New York. and eventually goes and reshapes an industry that is huge, and it's a lot about connections.

So how did you grow up, and what intrigued you about the space? It didn't seem tiny at the time that I grew up there. I grew up in Cleveland, Ohio. My father was an industrialist in the steel business. My mother was a painter. I grew up in a fairly small community with a fairly average normal life. I was very fortunate that my parents were incredibly generous, fabulous, and wanted me to have all the

opportunities that maybe they didn't have and to be able to see the world and to push the boundaries of what I could be or become. And, you know, growing up in a fairly normal place, I went to public school. I went to prep school. I grew up in the Jewish community. My father was first generation. My mother was second generation. So growing up in sort of that generational dynamic of coming from the old country or learning how to fit in or being American or being second generation or third generation defined a lot of who I was. And I always was a very, active mind-wondering sort of kid. I always had dreams. I lost myself in the movies, reading books, reading magazines, watching TV, listening to music, because I always felt

that the world had so much to offer and that I wanted to be the person that had something to offer to the world. And it didn't happen by grand design. It happened organically. I was a painter. I took art classes. I traveled around the world every summer. It was either on a European tour or tennis camp in the south of France or climbing Mount Fuji in Japan on a study tour. But from the age of 12, my parents allowed me basically to leave and to explore and to immerse myself outside of my comfort zone and to be exposed to different people, different culture, and different aspects of life from all socioeconomic backgrounds. At that point, when you're a kid or a teen, if you will, do you know that you're going to be

drawn to fashion or did that just stumbled on you? I always with somebody that loved the escapism of music and film and magazines, are really going to date myself here. My parents were pretty fashionable, actually, considering where I grew up, my mother's father was in the yarn business, and his father had started a company in Jamestown, New York, called National Spinning. And my mother, they were the manufacturers of Rudy Gerenwright. So growing up in Shaker Heights, Ohio, my mother was walking around in the mall in Rudy Gernright, not the topless bikini. My mother was really fashionable. And my father loved architecture and design. So I was exposed to it and things that you wouldn't expect a kid to be exposed to growing up in Ohio. So I was very fortunate to have had enlightened parents who always were curious and

wanted to know and pushed me to be the same kind of person. And then he went to college? Unconventional choice at the time, in retrospect, brilliant choice. I went to Stanford University. At the time, my final three years of high school, I went to a prep school in Cleveland called University School, which was 100 kids, which most of the legacy students went on to Ivy League or East Coast or Midwestern Pillar Schools. And I chose to go to California and I chose to go to Stanford because it was not the traditional

choice. Stanford was and is even more so an amazing educational institution, but I wanted to do something different than everybody else. And at that time, people didn't even know that Stanford wasn't in Connecticut. We're talking a while back, or now it's the top-rated university. You know, in the country, it was an unconventional choice to go far away from home, to go to a place that was not within my social circle and to experience life in a different way. It was a great experience. In retrospect, my choice of going there and the type of things that I'm interested in, in those years, Stanford was really famous for engineering, computer technology, foreign policy. it actually was not as strong in the arts, the humanities, liberal arts. So I discovered the fact that actually I was interested in the arts and creative, in style, in fashion, in filmmaking, and entertainment, and photography,

in an environment where all the Silicon Valley legends were incubating while I was in school. This was the time period in the 70s where the student would quit his job. junior year, hire his professor and start a multi-billion-dollar technology. I was not that tech person. I was not an engineer, but I was there in this moment where the Bay Area and particularly the peninsula in Silicon Valley became the building blocks of the society that we live in right now. And it's fascinating times to be around, I'm sure. You know, Texas instruments in Hewlett-Packard were the touch on IBM. Apple computer was just starting. Facebook would happen two or three or four years later. But all these things and all these people and all that thought process was

incubating in that academic environment. So I was there on the ground floor, not by grand design, by instinct. Instincts count a lot in business. We'll talk about it, but you started as an artist and in sales, Rflon and Macy's and Bloomingdale and Sacks and Benton. How did you get to some of these and what shaped you? I studied undergraduate. I studied French literature and economics

because I had to reconcile the ethereal creative side of myself and the need to report something to make money and have a career. I'm reconciling my artistic mother and my business-minded father. When I graduated from Stanford, I'd lived a year in Paris as part of my senior year. And when I arrived in Paris, it was a program that was between Stanford University and NYU. And I chose not to live with a family, but I found an apartment in the International Herald Tribune because I wanted to live by myself. and the apartment that I found was the Chambre de Bonn or the maids room in a hotel particularly air that was the epicenter of Andy Warhol's factory.

So growing up in Cleveland, people were wearing duck pants and the Crepe Handbook and all that other jazz, I arrive in Paris studying, living in this building with the Brandolini family and Andy Warhol and the founder of ClubMed, on Ruta Sher Shmidi, and this was the beginning of my personal enlightenment or understanding the world that I did not know existed. And being there as a student, I was in the middle of watching the entire factory underground scene of those years were everyone could be famous for 15 minutes, and it had a huge impact on me. And by being in Paris in those years, I got to know a lot of people in the fragrance business, in retail, in fashion, and in the arts. And I grew to learn that actually that was a business and something I was

actually interested in. Wow. So at that point, though, John, just to lean into this for a second, is that overwhelming? Is that scary? Is that exciting? It should have been overwhelming. Many of the things in my career, I should have been scared because I actually known what I was up against or known what I was walking into. I may not have had the guts or the drive to actually understand what could go wrong or why I could not succeed. And this one other side backstory for the beauty business that dovetails into this. My grandmother's first cousin was a man named Bernie Mitchell, who had made it killing after World War II selling air conditioning units in Chicago.

And he was trying to develop an entrepreneurial business. And he discovered that there were great gross margin profits in the fragrance business. And he created Jovan. So Jovan Musk was the pheromone musk sex fragrance of the 70s and the 80s. So I had a cousin, a third cousin, but a cousin who had become very successful in the beauty industry, creating something that was part of the family. So it gave you the seed. It gave you a seed that is possible. Anything is possible.

But if you don't expose yourself to a lot of things, I guess this is my first life last. You don't know what you don't know, and you don't know what you don't like until you try it. And I've always been a person that's tried not to have preconceived notions and to push myself to learn things and be places that maybe I would like or maybe that I wouldn't like, but how would I know unless I exposed myself to it? So having the experience of spending a lot of time internationally growing up, studying abroad, and being touched by the bug of this dreammaker's sort of iconography of fashion and art and beauty and entertainment, these things really spoke to me. So I went to Paris, graduated Stanford, came home. I remember coming off the plane in Cleveland, and I, at the time, the Brashe thing to do in France was to have your collar up.

Like it was very new way. Like the movies. And my father, the first thing he did when I got off the plane was put my collar down. He said, you need to put your collar down. And I said, why are you asking me to put my collar down? He said, everybody in Paris wears their collar this way. And he said to me, you're not in Paris anymore. That was the first thing.

that I had, back to reality. I needed to get on a dodge and that my future was not going to be in Cleveland, Ohio. Wow. And that I needed to venture out into the world with some preconceived notions of what I wanted out of it. But I didn't have a master plan. I just knew I wanted to do something that was creative, inventive, exciting, that was not the standard path that all my friends took. When I graduated from Stanford, people went on to get their law degrees or they went to Blue Chip investment banking firms or worked on Wall Street or worked in Kellogg's or big, big P&G sort of marketing backgrounds. I went to NYU Business School. I went to Stern. I studied finance and marketing. Once again, trying to bridge that making a living and doing something more

creative and more brand-oriented. And when I graduated from business school in 1982 at Stern, I had to get a job. And I applied to a lot of advertising agencies. And I applied to some beauty companies and some entertainment companies on things that I was interested in. And my dad told me, if I didn't get a job, I'd have to come back to Cleveland and to go into the family steel business. So a friend of a friend of the family knew Rosemary Bravo. And Rosemary Bravo, who went on to become the CEO of Burberry and was actually on the board of Establer, or gave me my first job. And I went into the executive training program of Macy's in 1982, in retail.

It was a great retail training program, but I never knew that I never had any inkling of going into retail. And everything I ever learned or was exposed to in business. business began there, starting on the floor, starting as an assistant buyer, a trainee, learning the business from entrepreneurs and for people actually in the business of selling things and merchandising things. And I'm the guy who never could hold a job for longer than a year and a half for the first 11 years of my life, the guy that never left the job. So for the first 10 years of my career. I was at Macy's. I was at Bloomingdale's. I was at Saks Fifth Avenue. I was a fragrance buyer, an assistant beauty buyer. And I met every entrepreneur from Estee

Lauder to Charles Revson to Garillane family, the Arames family. And I got to be part of sort of the 80s beauty, zeitgeist, when all this sort of new beauty, particularly in fragrance with Georgia and Beverly Hills and Bijon fragrances and sort of the first wave of indie brands. And I got my metal there and then went and did an assignment, which I had no idea what I was doing, which worked for Luciano Benetton. And at the time, which was based in Treviso, and on a startup of bringing fragrance and beauty products into Benetton stores, which was way ahead of anybody doing anything like that, was there for a short while, then went to work for Revlon in the prestige division, which is just the time that Ron Perlman

had taken control of Revlon, and Revlon still was a major prestige player. And so for 12 years, I get a lot of scrappy job. I met amazing people that inspired me and taught me things and gave me breaks. And I can say that after my Macy's job, I never looked for a job ever again. It always came to me based on my work in my experience. What we call the hidden market, basically people brought you in because they've seen you. And one of the things that goes back and everything connects in some weird sort of way, when I worked at Bloomingdale's as an assistant, you had to work on Sundays. And on Sundays,

in those years, the buying floor was right off of the sales floor. And on Sundays, Estee Lauder, who at that time was in her 80s, would walk into Bloomingdale's 59th Street. And they would say that Estée Lauder is here, we need to go get her customers because she wants to start doing some makeovers. So I got to know Estee Lauder and actually Leonard Lauder and the Lauder family in the years actually when I was on the shop Ford Bloomingdale's and saw this legend actually come in and actually interact and touch customers every single time that you would come in. If you're feeling stuck, underpaid or unappreciated, or you're simply ready to take your career in life to the next level, I have the perfect solution for you. We have a program.

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slash free hyphen training. The link is in the show notes. Now back to the show. What an incredible experience. So wait, so Estee Lauder herself would actually make people's makeup herself. She would walk in and say, where are my girls?

That's how she referred to her sales staff. She goes, I want people in the chair. I want to show them how they can be beautiful. And being exposed to all this entrepreneurship in retail and all these people in independent businesses and giant multinational companies and working in skin care, makeup and fragrance and marketing and advertising, this was the best

experience better than any education anyone ever could have. And when I think about what would my life have looked like had I gotten into Harvard Business School right out of school or not done this type of path or had ended up in a big corporation and a big training program in a big way, would I have had the experiences or the exposure to what I had? And the answer most likely is not. No, right. And my advice that I tell people when they start is that you need to explore everything. And you need to see it from every touch point, whether it's from a manufacturing side,

the retail side, a customer side, development side, an international side. But exposing yourself to all the spokes in the wheel have, for me, been probably the greatest gift. My finding a way to marshal those experiences and to make them into a career that I was able to develop and bring something of myself that was different than everybody else has been sort of the underpinning of what my business success has been. And that's incredible. I just want to stop here for a second and for the listeners. is a lot of times we hear people that are scared that are too generalists. And I think if you really lean in and you hear this,

actually the fact that John touched every single one of these roles is a big reason why you were able to overarch and understand the bigger picture. You're hearing me completely right because I had the respect and understanding of everybody's job. And you know what? being in New York as an outsider, because when you're not from New York, you're not from New York. And being in New York as an outsider and growing up in a Midwestern environment and going to California for college, I saw the world a little bit differently than people that grew up in privileged Ivy League, Eastern Seaboard. So I've been exposed to a lot and exposed to a lot of

different people. And I never would have known what I was good at or not good at if I was I had stuck with a preconceived notion. So my advice to anybody is figure out what you love, what you're passionate about, and figure out how you fit into that world and how you can carve out your unique space or to say something individual or unique. And the only way to find this out is by experimenting, just like you did. You're not just going to know, but you're going to experiment with different things. I had good jobs and bad jobs.

I had great successes. I had failures. I had people that wished me well. I had people that did not wish me well. I learned probably more from the people that didn't wish me well, from the people who were there nurturing me to wish me well. Life is messy. Working in business and in careers is about dealing with all different types of people

from all different types of walks of life. And you need to know and learn how to negotiate that. and growing up a bit of a protected kid, no one prepares you for that. No one tells you what are the watchouts. So my experience has been grounded in real life, and my real life grounded experience led me to a career of high glamour, high fashion, trend, and aspiration that I actually had a chance to be part of the culture and influence it. So for a kid who grew up as an observer looking through the window to the world of other people doing great things, I actually was able to establish myself as somebody who actually was making those decisions

and doing them myself. And once again, it sounds a bit foxy, but it's true. So tell us how you got to Mac and some of those early lessons. Early 90s, I'm approached by the Estee Lauder companies. S. Day Lauder is still alive. And at the time, I was like VP. of sales in a commercial role for Princess Marcella Borgesa and the specialty division of Rovalon. And I was offered the opportunity to go to work for the mothership brand, Estee Lauder, and to take a lesser job in title, a lateral position to go run the West Coast office for the Estee Lauder brand.

So in 1991, I moved to L.A., left my comfort zone in New York City after a decade, and went to work for what was then a privately held company. And once again, events that changed my life forever. Because when I arrived in L.A. in the early 90s, which was a really good period to be in Los Angeles, I got connected in with the entertainment world. And I got connected in with the entire worlds of music and film and photography and production and agents and the creators of yesteryear, it was life-changing for me because all of a sudden I was plugged into Hollywood, not by grand design, but because of the role and the exposure that I got, I got to sit at the table or be part of a community that normally I never would have been part of. And that had an

impact. And I think at that point, and correct me from wrong, but Mac created this movement, Right? They were bold. They drove collaborations with pop stars. Take me on the journey. Early 90s, I stay in L.A. a year and a half. I brought back to New York. I'm the number two executive at the S. Dale Order brand reporting to Robin Burns and Leonard Lauder. I get an offer from Paris for a hot shit brand with a globally recognized luxury company. I thought, well, I think I'll go, move to Paris. And Leonard Lauder told me, you're not leaving. I said, well, What do you mean? I said, you can't leave. We've invested too much in you and you've invested too much in us. And he said, well, I'd like you to become the president of prescriptives,

which was Estee Lauder's indie brand that was developed internally. And I said, I'm sorry, I don't think that's the right job because I don't think it has a great future. And at that time, Estee Lauder went public in 1995 and Leonard had actually invested in Mac Cosmetics from the original two founders, Frank Toskin and Frank Angelo. And by 1998, when the company had taken over Mac, it was a $60 million business. Frank Angelo had passed away. Frank Toskin was there. The business was based in Toronto, Canada.

And Leonard said, what about Mac? And I said, you know what? I'm in. I had no idea what I was in for. I knew the brand was cool. I knew the brand was counterculture, I took a place in Toronto, and the only piece of advice I was given was go make Mac more Mac than it ever was. So when I arrived in this business, people were terrified. Here was this guy in the navy blue suit, the suit from Estee Lauder,

coming to this brand that was counterculture driven by makeup artists and people living on the fringe wearing black and I went from the men in blue suits to the men and women in black and I always loved pop music and I always loved the art scene but here I was in an alternative world

and in an alternative universe so where Estée Lauder was you know Philharmonic or Lincoln Center or doing things that were you know more traditional or the Southern Women Show or doing things in more traditional beauty paradigms. Here I was in a... Almost opposite.

Where gender fluidity and standards of beauty were completely a 180 from what I had been exposed to. And I embraced it. And I took all those people who were afraid that I would destroy what made this thing so unique and special. And my lifelong mantra is, is the answer is always in the room. You don't have to leave the room. When I walked into Mac and I met the people who built that business, I built the business off of the authenticity, the ethics, the values, and the unconventional embrace of things that might be disturbing or different for the more conservative parts of the world. And I took Mac from a niche indie beauty brand to what its high watermark was the largest color cosmetic brand in the world. And that job, which once again, I mean, yes,

I knew what I was doing, but did I know how to run a factory? No. Did I know how to do R&D? No. Did I know who do product development? No. Was I a PR expert? No. Did I like fashion as a customer? I like entertainment as a viewer? Yes, but I all of a sudden was in a position to do something. And I took that experience and it took that opportunity to define the path for Mac, which went on for 24 years and created something granted on the incredible foundations of the founders of that brand and the incredible value system of that brand, but so much so that people think I'm from Canada. I was synonymous with the success of Mac,

and I didn't get Mac until I was 39 years old. So I was working in a lot of jobs for a lot of people being people's number two for, you know, 15 years. I was not an overnight sensation, and I was always the same person I always was. but there I was in a position to actually do something. Let me ask you, John, because one thing, when you run something so big and you try to create such a big transformation,

there are usually some very hard challenge that come with it. Can you share something? Well, I had two challenges. First of all, I had the challenge of going someplace that was 180 degrees from the company that was working for. And I needed to, first of all, prove my worth to the people actually who built that business and that I wasn't just riding on somebody's coattails, but actually that I did have a vision and I could take this business forward to be a global player and to embrace its inclusivity

and its diversity in a way that made a difference. At the same time, I had to deal with my senior management who had no idea what I was talking about or what these people were doing. They knew they were very successful and they wanted part of that financial success, but they had no idea how fundamentally different it was to the way that they ran all their other businesses. And that was a challenge because I needed to prove myself to people who didn't think I could. could understand and defend myself to people who wanted me to deliver what they wanted, and I needed to bridge the two worlds. And I needed to have a point of view. And it's always about people. I have always surrounded myself by great people, young people, older people with experience. And at Mac, my personal assistant became the personal assistant who was the founder's personal assistant

from the beginning of the company, Beverly. I took the makeup artist that created the brand. I found the makeup artist who worked in the UK, on Princess Diana's makeup. And I brought these people in that were the unsung heroes of Mac, and I brought them into the tent with me. I moved the business to New York.

I set up a pro shop with the founder of the company. And I learned the fashion, culture, makeup game on the ground, building the brand and building relationships. And not only did I do it in the U.S. and Canada, I opened up almost every single international market in the

world. The brand had been established in London and Paris and Hong Kong and Milan, but I would go and I would understand this is before social media. This is before the internet. It's kind of interesting. 1998, the year that I took control,

is the year that the internet was born. That's when MySpace started arriving. And the early days of the dial-up of AOL on your computer or not even a laptop, on your desktop, and I would travel around the world and I would learn the culture of beauty, fashion, and humanity on the ground everywhere I went, whether it was in Shanghai or Tokyo or Paris or Amsterdam or Quinn or South Africa or Brazil. And that experience of being able to be on the ground floor of defining culture and using a brand that was based on inclusion and diversity and democratic pricing was an unbelievable opportunity. And the other thing was there was this little general.

of a charity that was there called the Mac AIDS Fund. And when I arrived, they had a product called VivaGlam, and the Viva Glam lipstick was an overstock product that they created a campaign around to raise money for men, women, and children affected by HIV and AIDS. And the first spokesperson for that campaign was Rupal, and then it was Katie Lang. So when I arrived in 1998, the MAC AIDS Fund had raised a million dollars off of the sale of this.

lipstick and was talking about AIDS and sex and things that people were uncomfortable of and behavior and disenfranchised communities and people left behind. And I knew that I had been given this opportunity by divine intervention that I could do something. I took that MAC AIDS fund over the course of 20-something odd years and I became the largest non-farma funder of HIV AIDS on the ground programs in the world. I raised a half a billion dollars. I associated myself with bold-faced, outspoken, sometimes polarizing celebrities who were talented and were not afraid to speak their mind. And it was that embracing of uncomfortable topics and things that mattered and things that affected people in the world

that I knew I could make a difference. And the more I did with Viva Glam and raising the money and raising the voice of the brand, the more successful the brand was, the more successful the company was, and the most successful I was. And the interactions of the people, I'm the guy who made hip-hop the reference point for beauty

going into the early 2000s. In 1998, the number one song in the world was by T.O. L.C. It was called Unpity. And the song sang about, it doesn't matter how much Mac do you wear. And it was the MTV years and Ozzy Osbourne and Sharon Osbourne and Kelly Osbourne were wearing Mac. And we were in MTV. And we were in the making of the band. And I was giving money to artists like Amy Winehouse. Take me there. How did you do you? you even get to these artists? I think some people would love to hear. First of all, the brand still does, has incredible products with products that pay off that were developed by and used

by makeup artists. And Madonna, when she did her Truth or Dare film, actually was one of the first people to wear Mac. And it was the combination of Madonna and Linda Vangelista, who grew up in the suburbs of Toronto, near, actually, Niagara Falls, who took her spice lip pencil. And when she became the supermodel of the world in the 90s, she brought these Canadian makeup products, along with Naomi Campbell and along with Christy Turlington, who also was Canadian, and they took them around the world.

And everybody wanted to know, what is this Mac? Who is it? What is it about it? And theoretically speaking, it shouldn't have worked because it was a brand that was 100% experiential. It embraced core values and inclusivity and diversity before it was even discussed, dealt with uncomfortable issues and supported a lot of artists who were flawed individuals of great talent. and being a brand that had the humanity to embrace the flaws in others and to find the beauty of the difference was what made the brand a global phenomenon.

Let me double click on this just for one second, though, John. I know a lot of people are like, I would love to be able to reach out to some of these influencers or celebrities or pop artists. And again, when you have a brand, it's easier to already, or when you have Madonna, you can already name drop. But share a story for a second from one of the first ones that you try to reach out, or maybe there was a rejection.

Like, the first ones are always the hardest to get them to say yes. So I zoned myself first on who loved us. Who loved the brand? And the people who love the brand were drag queens and people of color. because there were no shades for people of color. And the beauty industry did not embrace black artists and black celebrities. So I tried to, like everybody else, whoever was the movie star or the model of the day, and people would say, well, I don't want to do that.

That's too risky. There were a lot of very famous people that said, no, that I want to be associated with something like this. And I met Mary J. Blige and Little Kim because they were wearing Mac. And so it began. And every single person that I met and developed an association with the company one didn't come from an agent. It came from my actually networking and working with fashion designers, backstage and shows, film production, movie production, video production, being involved with the MTV Awards and the VMAs or much music in Toronto. But I did it myself. and I had an amazing communications partner.

Her name is Michelle Feeney, who lives in London now. She has a brand called Flower Street. But I did it with an amazing creative director, James Gager and Karen Bouglisi, who did the commercial side. And I did it because I was fearless. If I had known what everybody else was paying or what everybody else was doing, I would have been too afraid to walk in the room and even ask. I had the audacity to walk in and to ask, and I never accepted no phone answer. I don't even know if it could happen that way anymore today.

It happened the old-fashioned way, working hard, being there, being on the ground, but also willing to take risks, business risks, personal risks, reputational risks, doing things that were wildly commercial or wildly uncommercial. And the thing that's sort of interesting, I'll flash forward to a Mac's story, early tens, talking about the girl next door. And I went back to Cleveland, and we were talking about all these influencers, and all the thing that was going on on Instagram and YouTube and all these new stars and selling makeup, which was the explosion of what took place.

And everybody used to say, well, this brand is successful because, that's the girl next door. And I thought, well, who do you live next door to? And I went to the supermarket in Ohio and the checkout girl had her makeup done full on Kim Kardashian with false eyelashes and contouring and lips and, you know, all glittered up. And I thought, that is the girl next door. The girl next door went from fringe and niche to being the girl next door. and the girl next door went to fringe. So the whole orientation of the world and the way that the internet and online and social media started to mash up all these different cultures, changed the real world order of actually

what's beauty, what's shopping, what's discovery, what's aspirational. And it was a very, very, very, very exciting time. I discussed the fact that I was at Stanford during the beginning of Silicon Valley, being in the beauty business and the advent of the internet and social media and being a first responder and participant in it built the success of the brand. And I couldn't have asked for a better synthesis of the type of person I am or my philosophy of discovering and taking risk. to have had the opportunity of Mac. But Mac was not enough. And because of my success, I was tapped on the shoulder.

And I was given, in addition to my Mac responsibilities, the mothership ran Estée Lauder, which I had to deal with a more conservative, conventional beauty archetype. This is coming off of nine years of in black, full on Mac, full on raging at the clubs and the concerts. And this was the time in early 2003-4 when Estee Lauder had passed away.

And one of the people that I had met in my Mac years was Tom Ford. He had tried to hire me to run Yves Saint Laurent when he was there. And I used to send him brow products for he and his partner Richard because they liked the Mac brow gel. And he had not started his fashion brand yet. And I had had the idea with Leonard Lauder's full support that I wanted to bring Tom Ford in to guest at it Estee Lauder to remind the equity of what Estee Lauder did in the 1940s and 50s with Euse Thu and Azare. So I had a collaboration with Tom Ford that basically reframed the Estee Lauder brand in a completely different way. And in return, we promised to build a brand for Tom Ford. And at the time, everybody thought that Leonard and I were out of our mind.

Why would you commit to this, to this world famous designer who did not have a standalone brand yet and put the money and resources behind it? I believed in Tom Ford. And I believed he had something to say. How scary is it at a point, John? It was not scary then. When I reflect upon it, I should have been scared to death. when I started working on that, I was actually doing products that I wanted to buy. And when we

started doing fragrance and started doing makeup and all the ideas and concepts and things that we worked on, we didn't do any market research. I said, I want to just do the best. And I want to see the inclusivity and diversity in luxury that I saw in a democratic way from Mac. So the fragrances that Tom Ford and the Tom Ford team created were created based on architecture. types of people around the world. So I did the most over-the-top oud that spoke to a Middle Eastern customer. I did the most gourmand slugs of vanilla for Latinas or jasmine. I did the most ethically spicy fragrances for the urban community. I did intellectual, artistic. fragrances that were appreciated by bourgeois people that don't even want people to know they're

wearing fragrances. And the idea was to just bring out, along with Black Orchid, 12 fragrances that were unisex called Private Blend. And they were done based on the archetype of satisfying and bringing the best luxury product to audiences that were underserved. And that caused a revolution. changed the fragrance business. The whole idea of designer fragrances from yesteryear or niche fragrance brands or all that you see with the successes of Bayrato or the successes of Diptec or Dess and Durga or Lil Labo or Joe Malon or on and on and on. This was a paradigm shift because it went from doing a business that was just based on advertising and marketing where actually the money was in the product, the experience, and the juice.

And it revolutionized the fragrance business. At first, it was not that successful, but when it moved, the success of Tom Ford actually began in London. And all these people came and fell in love with the brand. And it created an entire industry of 50, 60 or 70 other brands. that have used that playbook. For somebody that doesn't know enough about the fragrance business,

how do you even test it? Do you have a test group to tell you if this is good or bad? Do you just guess? I've looked at love at every side. I've done commercial fragrances that are done with a lot of marketing rigor and consumer insights and testing

and analytics and data. When I did Tom Ford, I don't even know if I'd be allowed to do that right now. When I did Tom Ford, did it based on a quest to push boundaries and to just serve up the best, just the best. And some of them were very polarizing and not commercial. The things that we did that were commercial that were like Dior and Chanel didn't sell. The things that we did that took a risk or push boundaries redefined the entire industry.

So marketing or product development or knowledge, a lot of times, it helps you do the right thing for the right customer and the right business type and other things it tells you what you don't want to do. So to play against the commercial tendencies or playing against them. Because for everything that's successful, there's something bubbling up that's going to emerge to displace it. So those two work experiences on the luxury and on the makeup side and makeup artistry brands and artisanal niche fragrance brands along with luxury skin care and the whole dermatological aesthetics aspect of the business are probably the three biggest trends that have affected beauty for the last 40 years. And I was lucky because I got to

participate and I learned on the job. But I also learned from everybody else. I learned from people who no one talked to. I learned from the experts. I learned from the legends. And I always referred back to history. Because if something worked 20 or 30 years ago, there was a reason. And to understand what that reason was and to understand that reason of why it would work today, it evolves and changes. And my ability to rapid prototype or adapt myself as the world has become more polarized, more digital first, with more emerging consumer, more fragmented, more fragmented, more niche, I've had to learn on how to remain current and relevant is I get years and years older and my target customer is getting years and years younger. And a lot of executives

have a very difficult time reconciling how to stay current. Now, I'm lucky. These past 17 years, I've been able to grow up with a daughter. And I could start with Dora the Explorer and Peppa Pig and go all the way up to TikTok insanity right now. I can see the world through her eyes. I can see the world through my 32-year-old niece Molly's eyes. I can see the world through my mother 93-year-old eyes. But to be able to understand that in this digitized world that's community-oriented, you have to understand these communities.

and you have to show up and communicate differently to each and every one of them. So for the large corporations of the world that were used to the more mass merchandise techniques, they don't work the same way anymore. And that's why there's been such an evolution in so much disruption in the beauty business because nothing is permanent. The only thing that's consistent to me, and this is why the beauty business has been good to me is that beauty, it's a universal aspiration. I don't know one person who thinks they look too good. I don't know one person who doesn't think they shouldn't be more attractive. I don't

know one person who doesn't want to feel good in their skin or one person that maybe wishes they could take a couple of years off or not. No judgment. But it is an eternal quest. There's always a need. It's an unmet need. because no one ever feels complete. And the beauty business lives on that quest for that self-discovery. And, you know, some people think, am I in a business that monetizes people's insecurities or plays to stereotypes? Yes, there are aspects of the business that do do that.

Or give confidence. Depends how you look at it. But the way that I look at it, beauty is a tool. and it can be used to be whoever you want to be, if you want to be or not, no judgment. And when you look at beauty that way, the world of possibilities are endless because there are so many customers and so many consumers and so many populations and people that have their own communities that want to be seen and be heard. and what Instagram or YouTube or TikTok or now chatGBT does is you can actually be in that world

and talk to that world in their words in real time. You just need to have the product and the way to sell it that they want it. And as opposed to the old way of I'll make something, run some TV ads and some magazine ads and run some billboard advertising, and then they'll come to them all and they'll buy it and everything will be fine. So let me ask you, John, because at that point, you are with Tom Ford and then you overshattering the ST Louder brand and you see it grow to this mega, multi-billion dollar incredibly entity, around the 2020, you decide to leave or there's a situation there.

And I want to take you to a difficult topic because every single person that has done something big, there's going to be something, I think, somehow slamming their way. Talk to us a little bit about it. I made a mistake on something that I didn't understand fully. During COVID, I built my Instagram following from 10,000 people to 2 million people. And I would just repost grams. And I became sort of internet famous because people thought that my humor and my sarcastic wit and unique point of view was bringing joy and some happiness during a really, really, really, really, really dark time. So when people couldn't leave their house and, you know, it was really, really, really, really, really very sad. And as we came out of COVID,

because I've always been a person that has never been shy and has been bold and embraced things that are perhaps controversial. One day on my feed, there was a piece of content from a black content creator of a meme using the N-word in the context of COVID and Big Berg in the snufflewuckabas in a little red riding hood, granny kind of thing. And when I saw N. Dot.a, being the Midwestern older guy, Jewish, was somebody dressed up. and a granny outfit, n. Dot.A. was Nana. So someone screen grabs the post. And listen, when you're successful, not everybody wishes you well. No. Someone does a screen grab of the post. It goes on a vigilante site. And my PR lead calls me about 45 minutes later and said,

I don't think you understand what you just did. And she explained it. And I took it down immediately. It was just after George Floyd. It was the boiling moment in the entire world. And the narrative went from John Dempsey, the builder of inclusion and diversity and the champion of everybody and everything to being framed as an old, entitled, wealthy, racist, where everything had been handed to me on a silver platter.

I was working for a publicly traded company, I was not allowed to defend myself, I wasn't allowed to speak, and I needed to leave the job and the family that I loved for 32 and a half years. And to this very day, that false narrative on me still pops up from time to time. My daughter was cyber bullied by kids and people giving me attributes or a signing me personality traits or characteristics that have nothing to do with me at all. The mistake that I made is I had a big job. And with a big job comes big responsibility. And I should have been more careful that understanding that people could misunderstand what I said.

And I also learned that I didn't have permission to be 30 years old. I'm in my 60s. And these people have no idea who I am. these people have no idea what I did or what I did for these communities or how I supported people all these years and it was very hurtful and it was traumatic and my father and mother became ill and all of a sudden I'm not working I never had basically taken a day off my life was my job and my job was my life and I couldn't work and I was basically on a lockdown. And it was a trauma. And it took everything. Everything in my very inner soul to not lose

sight of the fact of who I was and that I was not going to be the canceled guy and allowed somebody else to define my narrative. And I want to go there for a second, John. I know that you're onto some big things now, but it took a lot of muscle to reinvent yourself and what I call leap. And I want to talk there a little bit because some people need to hear this. So first of all, I had to take inventory in myself. I had to bring myself in check. I was very successful. I was impulsive and down the rabbit hole in social media because I believe that social media

was where you sold products and that if you don't do it or live it, how can you possibly use it to build your brand? I went back home to Ohio, my father was dying, I went back to just being me, not being John Dempsey, the executive group president of Estee Lauder, or John Dempsey with Tom Ford or John Dempsey with Mac, just John Dempsey, a nice guy who's trying to do the right thing for his family from Ohio, who got the opportunity to build incredible success and notoriety for myself that was taken away from me in a day. And I was afraid to go out.

I couldn't even walk into a department store. I was physically ill. I felt guilty that somehow I'd let my company and my friends and people who believed in me down. At the same time, I was angry. At the same time, I felt persecuted. At the same time, I felt responsible. All these things very human. And I have a PR rabbi who helped actually organize this podcast with you who thought this would be a great format to talk about this.

And I said to him, well, should I take down my Instagram or should I do something differently? And he said, you're going to continue being you because that's all that you know how to do. And that's what made you successful. Your eyes are open. You understand the pitfalls. will you go be you, believe in you? And I took the time to do a book. I'm a passionate art collector and love decorative arts and photography. And I actually took my house and created a coffee table book called Behind the Blue Door. The book talks about living life to the max and discovering

and doing things for others and not being afraid to be bold and outspoken. And I used it as a declaration for me as a person, not for the job that I had. And the blue door almost was like a double entendre because I do have a Neve-Klein blue door, because Estee Laude was always referred to as big blue. And my point was, don't judge a book by its cover, or don't judge a book by the story that somebody tells as the unadulterated truth. And I didn't really talk about what happened to me. I just talked about it as sort of an intermezzo. But that was relaunching John Dempsey, the person, not the guy behind a lot of famous brands. And I learned a lot. I learned who my friends were. I learned who my friends were not. I understood people that were afraid to fraternize with me because

it put them at risk. I was understanding and had great empathy. I was incredibly sad. I worked on myself. I got myself in shape. I got myself more grounded with my family. I was there to be able to be there when my father died and to be there for my mother and, you know, things that I would not have been able to have done had I been in the rat race or the roundabout of the job that I was in. You're on to some big things, John. What do you want to share? I'm under a lot of really big things, but the things that I can talk about in a world of NDAs, the things that I can talk about is first at El Catterdon, I'm a senior advisor in beauty, and I was part of the deal team that bought a brand called Kiko Milano.

Kiko Milano is a makeup brand from Milan that is the largest independent makeup brand in the world. It had been in the U.S. and it failed. It's coming back. what I think is going to be a beauty revolution around the world. And then lastly, I was working as a consultant to The Gap Inc to imagine what beauty could represent the Gap. And it was announced publicly about a month ago. So I'm working on something in luxury with people I respect and admire on something

that sort of feeds my creative juices. So, John, based on everything you have, have. What would be one thing that you wish you would tell your younger self? Don't be in such a hurry. I was a guy who was always in a hurry, did impulsive, thinking that time was running out, I think to whether it's pushing a meme on Instagram before you took a second to reflect upon it, or thinking that you should be doing certain things at certain stages of your life or have a certain status. You got to know yourself. You need to know your strengths. You need to know what your value at is and where you make a difference if you want that kind of life. I didn't want a life just to do a

job. I wanted a life that I could change things, shift the culture, shift the narrative. And I'm still very lucky, but I'm still able to do it, even after an unfortunate pause. So I'm a guy that grew up, analog, listening to the radio, who transformed himself into the digital age, embracing all media, building brands on social media, interrupted professionally and personally by social media, and moving forward again. So my story is a story of... Always reinventing, always at the forefront. I do not think of myself. And people ask me, What gives me the right to do things for younger people? And the thing is that I don't think of myself as being my age.

That's an ageist way of looking at things. I think of myself as current as somebody 22 years old. Sometimes I think of myself as more current of some of these younger people that I've met. Because I never stop the hunt or the lust or the desire for understanding what's next, what's interesting, and what's new. And if you're not curious and you're not willing to take risks or you're not able to push yourself out of your comfort zone, you're not going to grow. And I guess from your philosophy of your business and your podcast, I understand why Matthew felt that I should speak with you with the Leap Academy because my personal story is all about Leaps. And sometimes with no one below me to catch me. And sometimes getting hurt, but never giving up.

That's the best advice I can give everybody is be focused and understand what it is that you're trying to do. Have a plan, but it's never going to end up the way you planned it. You need to be flexible and have the humility to know that God has a plan. and you don't always know it. So that's my overarching philosophy. Continue reinventing and leaping and doing big things with a big heart. I'm speaking to you today about something that I have not even spoken about this publicly up until about a week ago in the last three and a half years about my interruption.

I'm being my authentic self. I'm telling the story in my words in the way that I know that it happened. and if you're not going to like me, there's nothing I can do to make you change your mind. All that matters is that I'm true to myself, I'm good in the businesses that I'm part of, and making them successful, and making sure that all the stakeholders are enjoying it with me.

And I love that conversation, John. I think it's really, really important. I shared with you. We had Don Ariely on the show who had a lot of hate. When I kept my announcement of The Gap, which they were very proud. They knew everything. Everybody's very, everybody knows everything.

The haters came out. They started posting things. They posted things on the corporate website of the gap. They started posting things about. And I just thought, will this ever, ever, ever go away? And the reality of this, once it's online, it's forever. And all you can do is define yourself by your actions. and be a good person.

And that's why I wanted to shine an amazing light on you, John. I know you created incredible change. There's a lot more coming. There's always going to be haters. And we're going to change the world despite of them. So let's go, John. I wish I could talk to each and every one of them, apologize or try to explain my story.

But I need to look forward. I'm optimistic and love what I do every single day. And that's the key to success. Oh, and I want every single person that is listening to this to have the same sense of hunger and pride in what they do and to continue leaping again again to something great. So, John, thank you so much for opening up and to sharing your story and to continue changing the beauty industry. Thank you for having me and giving me the opportunity to talk about these things that I'm passionate about. I appreciate it. I hope you enjoyed this as much as I did.

If you did, please share it with friends. Now, also, if you're feeling stuck or simply want more from your own career, watch this 30-minute free training at leapacademy.com slash training. That's leapacademy.com slash training. See you in the next episode of the Leap Academy with Ilan and Godin show.