Jeremy Weisz 20:28
So if you like this story, also get the book. But seriously, there’s so many good stories and lessons learned, and that one in leadership and fairness, with your boss from the shoe store. So I want to fast so the, you know, the book should have been called Monkey Poop to Victoria’s Secret or something like that. Jeffrey, but let’s fast forward a little bit to University of Wisconsin and some lessons learned in building an actual fashion brand. And by the way, for people listening, Jeffrey was a philosophy major, so he was not majoring in design or anything like that at school. What were some of the lessons building up that company?
Jeffrey Madoff 21:16
Well, first of all, I believe everything you do informs everything else you do. So they’re not so desperate. You know, I had a double major in philosophy and psychology. Well, now a huge thing in business is behavioral economics. Why do people buy what they buy? Why do they decide what they decide? Why do they believe what they believe? Something I always found fascinating, but in the past 15 years that’s had tremendous applications in business, and it’s only growing. So, things aren’t necessarily as siloed as they initially seem to be. I learned so many lessons in terms of the fashion business, which apply to all businesses. And hiring people. And how do you hire people?
How do you settle disputes, how do you create really fruitful collaborations. What are the basic lessons in business? Because there’s so many self-help books out there, most of which I think are useless because you can’t replicate somebody else’s life and somebody else’s circumstances. So there’s best practices, which is really important in business but then it’s about relationships. And I think everything comes back to relationships, and relationships are so important, and that’s not taught in business school, and that’s not taught to you when you start working someplace, and the relationships have so much to do with one success in business. And I think ultimately, success in life is so based on that. But I learned so many things because they were so formative at a young time in my life that it’s hard to single out specific episodes.
Jeremy Weisz 21:21
It built the company up to over 100 people. What were some of the things you were selling just to give people an idea?
Jeffrey Madoff 23:35
So I designed men’s and women’s clothing. And pretty early on, I started getting a lot of publicity. I was in vogue and glamor and Esquire and Playboy gentleman’s quarterly glamor, all kinds of different magazines. And at that time, magazines were doing an iteration of what’s ended up being social media, which is getting word out there, creating followings and all of that. And so, my fashion business got known through the publicity that I got. And I was kind of an outlier, not being based in New York, but I sold to many of the best stores in New York.
So, it was interesting, but one of the big things that I learned, and I’m fortunate to have learned it young, is that I was employing like 120 people, and I realized I don’t want to do that. And so my film production company, when I transitioned to that, I had a core group, and then the film business is very much a freelance business. So there’s freelance cinematographers, production assistants, makeup artists, stylists, on and on and on. And I realized I like functioning like that much better than I like having a really big staff, because the bigger your staff gets, the further away you tend to get from the things you really enjoy doing and why you started the business in the first place.
So I learned that lesson really young, and that was a tremendously important lesson to learn. And there were just things that happened all the time that helped me inform myself and make better decisions as I moved forward.
Jeremy Weisz 25:26
What would be an example of something that was in the magazine, like, if we were to picture it?
Jeffrey Madoff 25:31
But yeah, it might be a picture of like, was a very big deal back then to be on the cover of Women’s Wear Daily, because that was the main fashion trade publication, and one of my designs, was the front page of that paper, which got me tremendous exposure very early on. So it was often a picture of an outfit or something like that. Sometimes I’d be interviewed. I made up insane stories during the interviews, like when I was chosen, I was chosen one of the top 10 young designers in the United States, and I was interviewed by a lot of press. I’d never been interviewed before, so I decided I want to have fun with this. What can I do? And so I made up an insane story about how I became a designer, which got published all over the place.
And my dad said to me, I showed him the article, and he said, you actually told him this shit? Yeah. And he laughed, and he said, and they wrote it. I said, well, you’re holding it, yeah. And it was very funny, and I learned lessons about public relations, and marketing that were kind of fun. But for me, it was really about the fun of it, not developing strategic thinking around it, because I tend to glaze over when it gets too academic like that, but creating stories, which is what a brand is, a brand is a good story that resonates emotionally with people, and that’s what good press is, and that’s what good stories are. So it was a lot of fun. So I learned about that.
Jeremy Weisz 26:28
How did you originally, what was the kind of inception of getting covered in this? I imagine someone discovered you somehow or the clothing. Do you remember one of those key moments? And why did they even contact you?
Jeffrey Madoff 27:47
Well, they have a job to do, and the job is to give readers a reason back in that time, now it’s to revisit your Instagram account, or that sort of thing. But in those days, it was to come back and buy the publication, so they knew who their audience was, and so they wanted to refresh all the time to give you a reason to buy it the next month and the next month or the next day, in the sense of Women’s Wear Daily. So they’re always on the lookout for new ideas, new designers, new products, all of that sort of a thing. So I was a novelty because I was selling to Bloomingdale’s, which at that time was a top department store in the United States, to some of the top specialty stores in the United States.
Yet I’m some kid from Wisconsin at that time. It was right after college, and so I was a novelty. And then I’d come into New York for some of the shows, the trade shows to sell the clothes, and buyers would come in, and they all talk to each other, because the fashion press would talk to the influential buyers, and there’s just all this crosstalk that goes on. And then people reach out. There is a guy from AMC stores, which is one of the largest department store groups in the United States, it’s no longer the case. They were huge. And I get a phone call. And my factory, by the way, was in foot Ville, Wisconsin. I’m sure you’ve heard of it,
Jeremy Weisz 29:23
Been there. Been there many times.
Jeffrey Madoff 29:26
Yes, it’s right near. It’s a left turn from ankleville. But anyhow, this guy calls me, and I didn’t know who he was, and he was, at that time, the most influential department store buyer in the country, and he said he gets me on the phone, and he had tracked me down, and he said I was walking in San Francisco, and I see this guy wearing a shirt I thought was amazing. And I wanted to find out what, who made that shirt, whose shirt is that? And the guy must have thought I was crazy.
I stopped him, and I said, Who made your shirt? Whose shirt is that? He said, It’s my shirt. He said, No, who’s who made it? Who let me look? And he turns the guy around, and the guy doesn’t know what’s going on. And he looks at the label, Billy Whiskers, which was the name of my company. Where’d you get this? And so the guy thought he was nuts. And he said, yet, that store, mentions the store wherever it was, in San Francisco. And he said, So I tracked you down in Foothill, Wisconsin, where the hell is Footville, Wisconsin. And so I listened to this guy talk for like three minutes, as if he had had 17 cups of coffee injected into his carotid artery. And I said to him, who is this?
Jeremy Weisz 30:52
By the way?
Jeffrey Madoff 30:54
And he said, yeah, by the way, who are you? And so he said, I’m Bernie Ozer. And he was, Bernie was like, a very big deal in the world at that time. And he was quite a character. And he said, why aren’t you proud of me? I found out where you are. This is great detective work, you know, finding out Footville, Wisconsin, where in the hell is that, that sort of the thing. And so he invited me to his office. My next trip to New York invited me to dinner first, and it was with Andy Warhol’s group of people, people from the factory. And, I mean, it was crazy. This is in the late 60s, early 70s, and it was amazing, but people discovery was a huge part of the fashion business now, just like it’s very parallel, by the way, to the independent film business, which, in the 70s, boomed, with Scorsese and Coppola and just these great directors telling unique stories that were outside the studio system.
Well, that’s what the design world was like. And then, like the film world got basically co-opted and bought by major studios, the clothing companies in the last 15, 20 years have been bought by major companies, and so a lot of the really interesting creative edge is gone. But at that time, there was a whole lot to do with the joy of discovery, and everybody was on the hunt for something that was new and cool. So it was really a fascinating time. Same thing happened in the music business, by the way. The Beatles demonstrated that music could be a huge business.
Jeremy Weisz 32:40
Just to give people a sense. Jeffrey, at that time, when you’re running the clothing business, how old are you at the time?
Jeffrey Madoff 32:46
I started the company when I was, I think I was 21. And young people doing they weren’t called startups. But young people doing business was not a thing that was unusual. But my parents are entrepreneurs. My sister is an entrepreneur. She’s had her own business for almost 50 years. So I didn’t grow up thinking, God, I’d really like to land a good job. It was always to be that I just start a business. I never thought about ever getting a job? What’d your parents do? They were retailers. They had Women’s and Children’s fashion companies, the fashion retail, so very young when my parents had me come into the store and I would receive merchandise, and check the quantities against the packing order and then their original order.
And all that I did learn things, markup from wholesale to retail. And even when I was a young kid, I was learning things about business by osmosis because I’d worked in my parents’ store. My sister went into fashion retail herself, I took a totally different direction, but everything I learned helped inform me and prepare me for what I did.
Jeremy Weisz 34:05
The next piece is the content and video piece. How did you eventually get hooked up with Victoria’s Secret?
Jeffrey Madoff 34:17
It was funny. Things happen through a kind of serendipity, oftentimes, like you and I meeting, we knew so many people in common, but we didn’t know each other, which is kind of wild. And the person that I knew most recently, Bill Cates, is the one you knew most recently, and he’s the one that ended up introducing us, so you never know as things ricochet around and pinball around how things are going to happen? Well, enter the E channel, which was relatively new at that time, was going to be doing, they wanted to do a special documentary on the making of the Victoria’s Secret Fashion Show, which was not a big deal then, but this was going to be Victoria’s Secret’s first show in New York.
So it’s this brand out of Columbus, Ohio, that coined the term supermodels that was going to be doing a fashion show at, I think it was at the Plaza Hotel in New York, whole new venture. So I was contacted by the E channel because of the work I did with Ralph Lauren and with Halston, they wanted me to direct this special and so I went to a meeting. I was invited to a meeting that Victoria Secret was having with the people who were producing their first show. And the two people from Victoria Secret were interested in what my point of view was and asked me some things because they didn’t quite understand what they were being pitched by these other people, and I said to them, I’m just here as an observer. It’s not appropriate for me to give you any opinions of what I think of what they’re doing.
And I was like, what? And so after the meeting, they said, We want to meet with you separately. And so we met at my studio. They saw some of my work, really liked it, and then nothing happened for, like, six months, and then I got a call that they wanted me to do their next show, and we met and hit it off, and I worked with them for 26 years. They were a client.
Jeremy Weisz 36:46
One of my favorite stories of the book Jeffrey is about expectations, okay, because you were kind of ahead of your time as far as they did an online launch, and it was interesting, because the same outcome could have happened, and everyone would have been upset, but because you set expectations, they were thrilled. So can you just talk about what you did there when you set expectations for that online launch?
Jeffrey Madoff 37:17
Yeah, we were going to do the first live streaming fashion show. And this is back in I think it was like 1997 or something like that. So the largest event that had been online was and by the way, there wasn’t broadband at that point. Video quality was crappy, but the largest event, which I think had 350,000 viewers, was John Glenn when he went back into space. So we met at Victoria Secrets offices in New York. We met with Yahoo and AOL to talk to them about, because nobody had enough bandwidth to stream a live show, so they had to join together in order to do that. And so I had done my research, and I knew also what the expectation was of Victoria’s Secret.
So I said to people, I think was Seth Groden was with Yahoo, so that he and I met then, I forget the person from AOL, and I said, tell them what’s going to happen if they meet their numbers, because they said they’d get more than a million people, which is, three times more than the John Glenn thing had, and there wasn’t enough capacity for that. And they didn’t say anything. And I said, tell them what’s going to happen. And they didn’t say anything. And then Ed Rezac from Victoria’s Secret said to me, well, what’s going to happen? And I said, your site’s going to crash. They said, oh my God. What is horrible? Is that true? And they said, yeah, that probably is true. What are we gonna do about it? And I said, what you’re gonna do about is the concert sold out. You make it a positive that there was such demand. You crash the internet? That’s a much bigger story than if everything went well, because nobody cares. Just streaming on the internet yet.
So that’s, in fact, what happened is that it did crash. It became, it’s written up in the Wall Street Journal. It was all over the place. Victoria’s Secret crashes the internet. They didn’t really crash the internet. They crashed that particular aspect of it. And so that ended up being a real story. And that’s where marketing and PR come in is, how do you spin that story to the advantage of the company? I mean, that’s what PR is.
Jeremy Weisz 39:59
Another piece that struck me in the book is Ralph Lauren, and that you would have pushed back, actually, on you were creating a video for Ralph and 50th anniversary, I believe.
Jeffrey Madoff 40:24
His lifetime achievement?
Jeremy Weisz 40:25
Lifetime achievement? Yeah. And the interesting part to me was, I don’t know if people are used to pushing back on Ralph Lauren or not, but you definitely wanted a specific story, and it wasn’t received with necessarily open arms. Okay, so can you talk about your thought process on just continuing to push back on what you thought should be created for this.
Jeffrey Madoff 40:55
Well, as a general principle, I believe that if you hire me, you’re interested in my opinions. Otherwise, why hire me? So that was and relationships, as you well know, are based on trust. And so I had been working with Ralph. This one you’re showing is the 50th anniversary, which I directed. The fashion journal was huge in Central Park, but Ralph’s Lifetime Achievement Award was a very big deal. It was held at Lincoln Center. Audrey Hepburn was going to introduce the film, and I was at Ralph’s home for dinner with he and his wife, and we were talking about what kind of film to create for the lifetime achievement award ceremony.
And I saw these photo albums that he had, beautifully bound photo albums that showed him when he was a kid and his relatives and things that nobody had ever seen before. And I said, I want to use this, these images to start it off. And he said, no. And I said, no, I think you’ve got all these beautiful images out there, but they’re all advertising images, even the shots with your family. These are shots that Bruce Weber did, and they’re beautiful. But I want to show the humanity of who you are. This is a lifetime achievement award, so let’s show who you are. And he said, now, and so coincidentally, and it was truly a coincidence, I had a DVD of the video that I had made for my parents 50th anniversary, because we’re going back to now, like 1991 or two, and I showed Ralph and Ricky, his wife, the video I did for my parents, and at the end of it, they’re crying.
And Ralph said, I’m crying. I don’t even know these people. And I said, well, I want to do that for you, and the only way I can do that and not just make it look like a commercial, is to use those pictures. He said, okay, and one it’s interesting, because one of Ralph’s metrics for whether something really works or not is if it hits him emotionally. So he had a very sensitive Gage. And by the way, I worked with Ralph for 38 years, I never had a contract. And I felt like, as long as I can keep bringing value to what you’re doing and you want me great, but if I’m not, then get somebody else. So we had a real trust, and I was able to convince him to do that. And then I’m sitting in the audience at Lincoln Center, and Audrey Hepburn comes out, and she gives us wonderful introduction, and the room goes black, and I knew that it would be the first image, which is Ralph as a baby.
This is either going to work or it’s going to bomb. And the fashion industry is a pretty jaded group of people. It’s a tough, tough audience, and so I’m just sitting there, and it seemed like quite a while waiting as the lights faded out, the screen lights up, and you see this picture of Ralph as a baby, and he’s one of these people that had the same face since he was a little kid. There are some people you can just recognize, and some people Bear NO. Resemblance to what they look like as a little kid. Well, he looked like that. And when the picture came up, there was this collective oh, from the audience, and I knew I nailed it. And it was great. And it was very, very well received. And I think that whenever you’re in a job situation, if you’re hired to do something, and you believe strongly in what it is you’re offering make the case for it.
Some people call that pushing back, but I do it out of what I believe is going to be successful for my client. It’s not an ego exercise. It’s this is going to work, and here’s why I think it’s going to work, and I have reasons for it. If I hadn’t had my parents 50th anniversary DVD with me, I would not have been able to sell the show.
Jeremy Weisz 45:51
Why do you think he resisted at first to that suggestion?
Jeffrey Madoff 45:59
That’s a great question, because I think this is something that permeates our culture, which is he has a certain brand image of who he is, and this is letting people behind the mask. It’s like a vulnerability thing, yes, and most people do not want to be vulnerable in that way. He could have been in his mind potentially, and that says my conjecture humiliated by that. Why is Ralph showing a baby picture? That kind of a thing, because that’s like that. But fortunately, he had the trust in me, and I was able to give him a compelling reason why this would work, and it worked gloriously, and that’s because he trusted me and I think again, seeing my parents thing he thought of it more of as a movie, and it had an emotional connection to him, and that’s how Ralph gages that.
Jeremy Weisz 47:08
I love that story. So thanks for sharing some lessons from Dan Sullivan. What are some of the things that you’ve learned? I know your friends colleagues with Dan, and you even have podcast episodes together, and you talk about them. What’s something that sticks out with Dan that you’ve taken away or learned.
Jeffrey Madoff 47:35
Dan and I, we do a podcast together once a month, and we really enjoy talking to each other. And we both have many divergent ideas, but the thing that’s interesting about it is that we are both very open. We’re both very curious. We both always hear each other out, and we spark off of each other in a really wonderful way, and it’s really great. And I can’t say that I’ve learned anything specifically, in terms of lessons, because we just really enjoy talking to each other and seeing where that takes us. But, I knew that in terms of curiosity and the importance of it, the importance of being open, all of those things, Dan, though, does have certain phrases that I love, like he one of those things with the play.
And Dan is an investor in my play, and one of the things about the play is he said, I love what you’re doing, and I love the play. And he has an itch about theater that this scratches, and it helps him be involved, or allows him to be involved in something that he finds really interesting. But he said, you’re doing something that is bigger than you have ever done before. And he said, I believe, and this is the part that I love. And he said, I believe in making your future bigger than your past. And Dan has some of these kinds of phrases which just really nail it in a really cool way. And that was very cool and very succinct, because that is, in fact, true. This is the biggest thing I’ve ever embarked on. It’s the biggest creative, intellectual and business challenge that I have undertaken, and it’s the biggest expression of what I believe to be my talents and my capabilities.
And Dan also has another phrase which I really love, which is unique ability. That’s kind of the cornerstone of his thoughts. And defining one’s unique ability is so important to, in terms of building your business and even your own self-esteem and personal success. So Dan has concepts that I wouldn’t really call lessons, but concepts that I think are really valuable, and we spark to those and and play off of each other in a really wonderful way, which I have tremendous gratitude for. And when he approached me to do the podcast, it was based on the fact that when he and I get together, we have great conversations and we enjoy each other. So that’s how the podcast came about, and those are the things from Dan that he has codified that I really like. And it’s great to explore those ideas.
Jeremy Weisz 50:54
Jeffrey, why write a play? It’s, again, another difficult undertaking, like the fashion business. It’s not just writing a play, it’s actually producing it, getting it out there. It’s a whole separate commercial endeavor. What made you decide to go on that path?
Jeffrey Madoff 51:13
I met Lloyd Price and here’s an example of what I mean about serendipity. I did the 75th anniversary film for Radio City Music Hall, which was really cool as part of the Christmas Spectacular. And they ended up using it for seven years. It was just going to be for one year. And it was very cool to do the project and shoot the Rockettes and shoot in Radio City, the executive producer, John Bonanni, who hired me, we got along great and established a really nice relationship. He left Radio City, but we stayed friends. And he called me up and said, do you know who Lloyd Price is? I said, Mr. Personality. Yeah, I know who he is.
You know anything about him? I said, no, but, I mean, I love personality. I love Stagger Lee, and I love Lottie, Miss Claudia, but no, I don’t know anything about him. And he goes, Well, we go to the same eye doctor. I’m here in the waiting room with him, and we were talking, and we want to do a short documentary about him. I think you two would really hit it off. When we finish here, can we come over to your office? Sure. So I met Lloyd. We did really hit it off. We ended up becoming very, very close friends, and when I did this documentary and I researched him, I realized, God, there’s an amazing story here, and it needs to be told because it’s about things that are very important to me. It’s about human rights, race, music, popular culture, all of these things that I find very, very interesting and fruitful to explore. And Lloyd’s story, he was an unsung hero.
He broke down the wall that was called Race records, where he could only buy records that were done by black artists in black owned record stores. But his first song back in 1952 Lottie Miss Claudie was the first song by a teenager that sold over a million copies. So nobody is Lloyd is black, nobody’s prejudice against green, which is money. And so he really opened the floodgates, and it’s one of the cornerstone figures of rock and roll, because prior to that, the music business was an adult business. Kids didn’t buy records because an amazing story. And people said to me, I love your question. Because people said to me, well, why don’t you make a film? You know how to make films. Why a play? And I said, I love film, but I love the immediacy of live and how when I see theater, it makes me feel. And I sort of dug deeper into that, in the sense that I think in live presentations. And this is true in sports. It’s true in music. It’s true, of course, on stage, on plays, but probably the biggest example, or best example, is a comedian. The feedback is immediate.
So if you tell a joke and people don’t laugh, you better learn how to recover quick. And I think any live performance, there’s a high element of risk, because things can go wrong. So you have to be nimble. You have to be quick. How can you do that? And so I wanted to write it as a play, and I’ve never let my ignorance. I didn’t know anything about fashion design either. I didn’t know anything about filmmaking before I started doing it. So I never let ignorance stop me, because if you’re stupid, it’s forever. If you’re ignorant, you can learn. And learning is something that I love. And again, it goes back to curiosity being the main fuel to creativity. And so I wanted to do a play and the reason I’m producing it is because nobody is going to produce a play by me. I was total unknown.
Nobody knew anything about it, and I had to change the perception of me from, well, who the hell is Jeff Madoff to, who the hell is Jeff Madoff? And because I’ve attracted Tony award winning talent, really fantastically gifted people that I work with to bring this to life, and it’s been fantastic, and that’s actually one of the things Dan Sullivan and I have explored a lot because he’s seen every iteration of the play is how business and theater are so much aligned that’s really interesting. So that’s why I wanted to do a play. I wanted to make people feel like I feel when I am emotionally moved by a great piece of theater. And that’s a core thing to me, because that feeling is wonderful, and I love it, and it’s different every night, which is really cool.
Jeremy Weisz 51:25
Jeffrey, I want to be the first one to thank you. Thanks for sharing your journey, your lessons. I want to encourage people to check out, you could see on the screen here, acreativecareer.com to learn more, you can check out the book and you can go get it wherever you buy books, and it’s amazing. I listen to the whole thing. Creative Careers: Making a Living With Your Ideas. If you are listening to this, and you know of someone, or you yourself, are looking for a speaker to your organization or Keynote, Jeffrey takes some selective items of those engagements throughout the year, so feel free to contact him, but check out acreativecareer.com. And Jeffrey, I’m gonna be the first one to thank you so much.
Jeffrey Madoff 57:31
Other one on here. So who else could thank you? I’d like to thank myself for being here.
Jeremy Weisz 57:36
Exactly. Thanks for sharing everything.
Jeffrey Madoff 57:40
Thanks for having me on, it was a lot of fun. Thanks Jeremy.
