
Loading summary
Mickey Drexler
What I do, I have a photograph in my mind. I go into a shop, it paints a picture or it doesn't. One bad color in a great painting that changes, throws off the whole painting. It's like the wheels, the ugly wheels on a Mustang. And I mean that. Every car now has ugly wheels. I can't get over it. You know, you see the wheels. It's like having a bad button on a sweater like this. This is one of our best sellers, and if you put an ugly button on this, that's what you notice. And I say, never give a customer a reason not to buy something.
Shane Parrish
Welcome to the Knowledge Project. I'm your host, Shtane Parish. In a world where knowledge is power, this podcast is your toolkit for mastering the best of what other people have already figured out. Most people think retail is about selling things. Mickey Drexler proved it's about selling dreams. As the CEO of Gap and J. Crew, he understood something profound about the American aspiration. People don't just want clothes. They want to become someone through what they wear. A boy from the Bronx who transformed into retail's merchant prince, Drexler could walk into a room with a hundred samples and instantly spot the three winners because he saw what Americans wanted to become before they knew it themselves. From advising Steve Jobs on Apple's retail strategy to building Old Navy from scratch, Drexler's career traces a remarkable journey of seeing opportunities that others missed. In this conversation, he shares the insights and instincts that let him repeatedly predict and shape American taste. Whether you're building a brand, leading a team, or trying to see around corners in your own industry, you'll learn how one of the retail's greatest minds thinks about the psychology of consumer desire, the principles of brand building, and the art of knowing what people want, often before they do. It's time to listen and learn.
Unknown Interviewer
Let's start at the beginning. You said your father was a model of what you didn't want.
Mickey Drexler
He didn't fit my job description of what I thought a good father should be. Yeah, I didn't know what I wanted then. I didn't know. You know, when you're a kid like you, moving all over the place, you don't know what's right and what's not right. You learn over time.
Unknown Interviewer
What was that relationship like?
Mickey Drexler
It wasn't good. He wasn't a sensitive guy. He had no emotion. He didn't treat my mom well, who died. You know, she had cancer the year I was born. And what was it like? I didn't know any Better at all. And I thought, this is what a father is like. And over the years I learned that this is not what a good father is like. And he never, he was an angry, bitter guy, was not successful. And you know, he always talked. He wanted to be a big shot. So in my family he acted like a big shot with my mom's three sisters and my seven cousins. And by the way, the irony is none of them liked him because he wasn't a warm, fuzzy, nice person. But I didn't know that when I was growing up.
Unknown Interviewer
How did that affect you?
Mickey Drexler
I think my ambition comes from being the opposite of him. I think I always lived in my fantasies escaping where I am. And Peggy, my wife, said, you know, maybe that's where your creativity comes from. I don't believe it came from that because I think creativity is part of your DNA and I don't think it can be taught. But, you know, it affected me. He never took any pleasure in my success and he just never did.
Unknown Interviewer
Was there a moment when you realized he wasn't a big shot?
Mickey Drexler
Well, I'll tell you, it's an interesting story. I used to work. He worked in a garment coat company. He worked buttons. He had kind of a low level, ish job, although I didn't want to face that. And he, they asked me to take the payroll. I was 16. He said, take the payroll to the bank. What do I do? I duck out the freight entrance on West 37th street and 8th Avenue, go into the neighboring freight entrance. I look through all the pay stubs or whatever it is. He was one of the lowest paid people there relative to his peer group who he would always put down and whatever. That was a reality for me. So it was a cold reality. So my thoughts of him being whatever disappeared then. And as I grew, he wasn't a good dad. So when I lived there, I was going to City College. I was miserable and I was, you know, I used to go subways, Long Island Railroad. And I'd had to escape from the house. So I luckily got into, I didn't know where to apply. State University of Buffalo. The first some guy I knew went, wasn't even a close friend I got in. So I escaped to Buffalo for two years. But it was, you know, never took any. He was competitive with me in an ironic way. And, you know, I was getting a lot of press when I, you know, I worked 12 years in the department stores and then I was very lucky, fortunate. I was called to run Ann Taylor then in 1980. I was a young Guy, you know, I don't know. I said okay because I didn't know what I would do next. After 12 years in the department stores, I couldn't find the stimulation and the excitement or whatever you call it of the organizations. And I don't think they're much different. Political suck up. I didn't know how to articulate this, but I think in most big companies people are always sucking up to their bosses. That's my own experience. And these develop over time because the boss reviews you, the boss promotes you. I've learned over the last number of years the best judge of a boss is the person who works for the boss.
Unknown Interviewer
And tell me more about that.
Mickey Drexler
Well, it's my own thing, I think in corporations and well, look at all the CEOs out there. I don't know all of them, but I think safe, they went to the right schools. I couldn't care less where anyone goes to school. I like to see a college degree, but I also like to see a work history. But if you're a safe choice and you know, it's again, it's an editorial on what I think people would argue if they went to a fancy school here and a fancy school there. And now it starts and I was guilty when my son was 5 years old going to a nursery school. I didn't have any connections. I thought it was a fancy one, it wasn't a good choice. But I think if you look at people, you know, like everyone, all these earnings reports, I know the public relations people write that, they script them and safe, you have a good education, you don't want to take a risk on picking the wrong boss or senior executives. And I think there's a lot of self interested people in this world, plenty of them.
Unknown Interviewer
Why do you think we're so risk averse?
Mickey Drexler
Well, I can't answer for others. I think you know why. I think you have to be creative to move any business forward, any institution. And that's what I think. And it's really based on my own personal experience. And also in the sector I'm in, fashion and all that. Creative drives the engines. And so why are they risk? It's a good question. Well, salary. They don't want to risk that. They don't want to risk that. I mean they get very wealthy these days. Becoming a CEO.
Unknown Interviewer
When you transformed the gap, you renovated all 430 stores at the same time with no focus group, nothing.
Mickey Drexler
Oh my God. If you take over something, you gotta get rid of the old merchandise because it ties up a lot of cash. And Don, bless his heart, was nervous about the earnings. I get emotional, you know, my stomach speaks for me a lot. But, you know, business got tough. For the first year, the Stock dropped probably 50%. You know, I never, I worked hard and I was scared. After a year, I'll never forget, we were talking about, it was a year and a half, we were in Carmel and we're sitting there, we come up with kind of a bankruptcy plan. That's when I started to get nervous. And I've been there a year and a half. Don redid the 400 plus stores. I redid all the merchandise. I threw it all out. And that's where he was concerned. But you gotta take and you gotta get the cash out of bad goods. It's like rotten fish or whatever. So we redid the stores.
Unknown Advertiser
Would you wear the same shoes for every occasion or rock the same outfit seven days a week? Of course not. Your style is better with options. Your investments could be too. CBOE index options give you access to various contract sizes, global trading hours, and potential tax advantages. That's a good look for any portfolio. If you're ready to invest in style, head to betterwithoptions.com There are risks associated with CBOE Company products. Review the disclosures and disclaimers@cboe.com USDISclaimers this.
Episode is brought to you by Indeed. When your computer breaks, you don't wait for it to magically start working again. You fix the problem. So why wait to hire the people your company desperately needs? Use indeed sponsored jobs to hire top talent fast. And even better, you only pay for results. There's no need to wait. Speed up your hiring with a $75 sponsored job credit@ Indeed.com podcast. Terms and conditions apply.
Unknown Interviewer
What gave you the confidence to do that? I mean, this was like a. Was it. We're basically going to go extinct. So that's the base case.
Mickey Drexler
Those two or three years, even when it turned around, was like, oh, but I worked my ass off. I kept. No one taught me how to run Ann Taylor. I just did it without any supervision because the headquarters $25 million business. But I just went in there day one and you know, corporate, a lot of people, they leave you alone or they don't leave you alone. But there I was. And the threat was, if I don't turn this. I was under pressure. I didn't make money there. They didn't pay me, I didn't negotiate, whatever. But it is what it is. So I always depended upon my gut, my instinct, and in Hindsight, I did. I knew who was good person, not a good person. I knew who was full of it and down to earth. And in the department store's 12 years, I kept looking for the right place to go.
Unknown Interviewer
You mentioned you could tell the difference between who was a good person, who was a bad person, who knew what they were talking about, who didn't. What are the tells? How would you teach somebody to do that?
Mickey Drexler
You can't teach anyone. I am a huge proponent and I never could say, like, Jesus, they're the president, they're the CEO, they're the this. And I'm thinking, I'm not impressed privately. And I can name drop some of the big shots of the time in the retail business. And I would say something like, not a merchant. And they look at me, that I could tell. And because I was a merchant, I guess my first, second day at Bloomingdale's, they put me in charge of a department because the buyer barber was on maternity leave. Stan Stern, who I loved dearly, he was a great boss. I was on my own and I just did it.
Unknown Interviewer
What does it mean to be a merchant?
Mickey Drexler
What it means to me is, and it's not a lot. I think it means to have know from what's going to sell well, from what's not going to maybe sell well. Focus, make sure it's on brand. Now, this is what I do. No rear view mirror. Most people do rear view mirror and they say, well, we sold last year. This. Sometimes it's going to go this way a lot. So you chase what's over in post peak. It means to me to be a merchant is having a sense of what's going to sell. Knowing that, like, I always had an instinct, I guess, on what I loved and I learned later on if I think it is non negotiable.
Unknown Interviewer
The word that comes to mind though is like taste.
Mickey Drexler
Well, that's a good question.
Unknown Interviewer
What's the difference between.
Mickey Drexler
Well, you know, for me, I use that word a lot, but it's in the eyes of the beholder. I have a friend, he's very successful. I was talking about the ugly merchandise in one of the companies he's involved with. He said, well, to the customer, it's not ugly. To me, it's ugly. Now I know what I know and I don't know where my eye came from, but it came from somewhere. But taste and style and fair value and moving forward and having a vision, those are the key ingredients that I think now when people say, well, look how good that company is, Doing I. I said, that's not what I like to do. I like to be proud of the merchandise. I like it to be fit my standards. I don't say it that way of what it is vision. And I liked. I like. I can always tell when something's not on brand. I remember in some of my jobs, I remember looking at something, it was a big tell. And I said, oh. And I didn't follow my instinct and really hurt one of the companies. You know, there's people involved. But it means to be a good merchant is. You can't define it, but you know when you know, you know it when you see it.
Unknown Interviewer
So if we were to like walk outside and walk in a store and you had five minutes to like walk me through how you evaluate the merchandise.
Mickey Drexler
Five minutes, three minutes. What would you look at the picture painted. Because when I just always. It's a really interesting question because I don't know how to explain what I look at, but I look at. Color's very important. When I did Gap, I had a list of styles I was trying to start something I was looking for, for my vision. I always admired Ralph Lauren, but I always thought I couldn't afford his clothes. He was a Bronx guy ahead of me and, you know, he always had a point of view and I admired him. I used to buy his clothes wholesale. Why? Because a friend of mine's cousin was his secretary. So I got it half off, whatever. But I always liked his taste. And it's still the same today. And there's not a lot of people who do that.
Unknown Interviewer
So it's interesting coming back to your friend's comment about. Well, the customer is deciding what we sell. If you're selling, if your game, I guess, is to sell the most product at the lowest prices, you're going to be selling the same thing that everybody else was selling. But you're telling me you wanted to create a different vision, one that escaped the competition in a way.
Mickey Drexler
What I do, I didn't say this is my plan. I look for white space. This is in hindsight. So Ann Taylor was hugely successful. I left after four years because my bosses were bureaucrats and I didn't like it there. And I also was at the stage in my life where I have to have something I wanted to do where I could feel not compensated the right. I was very happy with what I earned, but I faced the realities of living in Manhattan anyway. I always had. Ann Taylor was purely instinctive. But I did learn there that I didn't want to sell brand A, B, C, D. And today you can get every brand at a discount. And TJ Maxx, my friend there, Carolyn, she's the best. You can go to TJ Maxx and trust, but they're the biggest customers of most brands. So I didn't want to carry because Alexander's taught me the lesson. I was maybe 25 years old and I said, Jesus, something's wrong here. And you know, you kind of. I'm self taught. And then I'm also very curious. When I joined Ann Taylor Brooks Brothers and I saw it decline dramatically then because, you know, no merchants running it. The quality, they would take quality out to maintain price. But they had a protective device about competitors. They owned their name, they didn't sell wholesale. No one could take a markdown. So what I did at Ann Taylor is we did, I found some manufacturers today you get your own. But who can make goods? We design them with them. And we had Ann Taylor Studio label. Now no one told me to do that, but you know, do, do, do.
Unknown Interviewer
It's the white space.
Mickey Drexler
It's a. Well, yeah. And then I don't have to worry about meeting the competition. What's going on in the business today, by the way, is if you look at pricing, first of all, everything's on sale. I always give advice when I'm on a. Whatever I say before you give them the credit card, Google the item you want to buy. You'll find it somewhere most of the time.
Unknown Interviewer
Let's go back to the gap before we get to the end of the gap. So you were the CEO from 95 to 2002. How did you prevent the bureaucracy from building up over those seven years?
Mickey Drexler
Well, the bureaucracy is I'm all over everything. I took every call from a customer and they'd be surprised about, you know, and I say, if I can do it, you have to do it, you know. But today, you know, it doesn't always work. I tell every story, customer stories. I would call customers if they. Anyone who called me, I got back to them and you know, now I do that. It's a little bit of a payback because I never had anyone like that.
Unknown Interviewer
What were the key learnings from the Gap? Like what are the key lessons?
Mickey Drexler
Oh, every day, the key learnings. You must have a vision. You must be whatever's defined as a good merchant. You must be spot on and be a pain in the ass because the best bosses, and I always say, hire your boss because that's the one. And I never had bosses who I thought were the best, especially In. Yeah. But I became the boss. Other than Don was my boss there. And I had to play that game with him. Because if you do what I do, and I always use Steve does and you do what maybe all these other people do, you are always competing. You have to be competing. It's relentless and it goes with it. And if you're not, a lot of people don't compete. I know friends who run companies. They're bureaucrats. I know because I know them. So Old Navy. You know how I started that? One of my favorite stories so in the New York Times. I used to read it when it was a decent paper. Business section. I always liked to read about business because I wanted to be who they all were. And then I realized. Well, I didn't realize for a long time who they were, but not what I wanted to be. So there was a little article buried on page four or five about now. It was then called Dayton Hudson. Very bureaucratic company that I knew that they did a lot of research and a lot of this and a lot of that. And then someone was quoted as saying it pretty much going to be a cheaper version of gap week. The store opened. I flew out to Mall of America that week. I didn't even tell anyone, but I said, well, fuck them. And I went out Mall of America. I walked in the store, I was there no more than five minutes, and I said to myself, you gotta. Only the paranoid survive.
Unknown Interviewer
Well, that's interesting, right? Because it's a story of only the paranoid survive. And it's.
Mickey Drexler
And Andy Grove is the one who wrote that book.
Unknown Interviewer
But it's also a story of making sure that you're touching the medium. So when you're talking to customers, there's no filter between you and the feedback. When you're flying to the store, there's no filter, but you're looking at the terrain. Somebody's not telling you what it is.
Mickey Drexler
In corporations, most of the brass, they're in their ivory tower. I remember in the department stores, they're so far disconnected. Go on the selling floor, speak to someone. Plus, it's decent people for me. I identify with those people who aren't the fancy people.
Unknown Interviewer
Funny story about this. I bought an Xbox for my kids. It must have been, I don't know, seven years ago for Christmas. And we're opening it and we're setting it up on Christmas. And I was like, the person who designed this Xbox experience doesn't have kids. It took an hour and a half to play a game. From the time we plugged it in and turned it. It's like, first, you got to do updates. Second, you got to sign up for all these simple.
Mickey Drexler
Stupid is the greatest lesson. My first week at the Gap, I put up signs. Keep it simple. I took out the stupid. Every desk in the corporation, people would talk a language to me. I didn't know the language. I'll never forget this. This one woman, she's in charge of whatever planning and something. I didn't know what she was talking about. And I just said, keep it simple to the point you have to bring everything to its simplest common denominator.
Unknown Interviewer
And the best way to do that is to actually use your own product.
Mickey Drexler
Yeah, yeah. We did the pjimmy's pajama thing, which is a really fun thing. It's gonna be very good for him and us long term. And there's a. They call a boxer short. Well, their name for it was a short pajama pant. And they show me their new version now. It's the third after the pant and the pajama set. They're calling it the long. The Short Pajama pant, number three seller. And they show me this thing that they're changing it. Now. This is typical of what goes on. And I said, it's the third bestseller. You want to change it? I said, and it's called a boxer short. It's not called. I get a little impatient a lot. And then I do a little survey. I go around just to. I say, what do you call this? It's a boxer short. When you say the word boxer short, you don't have to describe is what.
Unknown Interviewer
Everybody has an idea of what it is.
Mickey Drexler
Of course, everyone knows it's an elastic waist. And I said, continue that, and you're not doing this, whatever it was. And that's what I do. And it's funny. And they call things. I like to name things that say what it is. And I go through this all the time. They confuse people. I said, there's certain names that you know what it is.
Unknown Interviewer
Everybody wants to come up with something.
Mickey Drexler
They don't know, but they're not logical. They don't.
Unknown Interviewer
So what happened at the end of the gap in your tenure there? Steve Jobs, Just to frame the conversation here. So Steve Jobs is on the board. He calls you. Take me through this.
Mickey Drexler
Well, Steve Jobs joined the board. He was recruiting me to join his board about a year. Steve is very seductive. He doesn't give up, like a lot of people who do what he does. And he called me one day and he said, I'll join the Gap board if you join my board. Deal. Because I knew Steve, you know, there's no such thing as an independent director. You know, there's a litmus test. Not a relative. They don't do business with you, but they ought to have on the test. Not a close friend, not a college roommate, not a cousin, not whatever. Unless it's, you know, if it's a controlled company, you can do what you want, but independent directors. So I said, didn't even think deal. I knew he would be Steve Jobs. He's irreverent, he challenges things. He might be late, but I love the guy.
Unknown Interviewer
What was he like as a board member?
Mickey Drexler
He was a troublemaker because he brought up things. I'd sit there, thank God, but he alienated people because, you know, it's okay to alienate people. He had he. But he didn't. He really wasn't a very paid attention board member. But I didn't care. So he was on the board only about a year and he wasn't very popular. But I just, you know, guy was, he was dying. I just so admired him. And I really admired him a lot. And Johnny, I was his lunch mate and I had, you know, Johnny and I became good friends and Steve was whatever. So there's a board meeting. I knew there was something going on. People all of a sudden, you know, when you have corporate and they don't. First of all, I never had a director who really understood the goods, you know. And you know, if they came in, they didn't like the name Old Navy. I got it off a bar in Paris. I was driving to the airport. I was fortunately in the backseat on the left. I'm looking out. I said to Maggie, she was in marketing. I go to Paris. You know, you go to shop, you get ideas, creative. So I see marquee with a lot of neon lights and it says Old Navy. I said, Maggie, that's the name. We needed a name for Old Navy, which, by the way, is about $11 billion business today.
Unknown Interviewer
Yeah, it's huge.
Mickey Drexler
That's the name. They didn't like the name. Long story short, I don't like agencies and I don't like consultants. And the Old Navy, by the way, that was started, it's a whole other story.
Unknown Interviewer
So let's go back to the firing. So Jobs is calling you.
Mickey Drexler
Okay, so this is. We had a bad year. So Jobs was not at that board meeting. I presented at that board meeting, the turnaround assortment, right? I looked at Banana Republic, Gap and Old Navy. It Was a tough year. I think in the marketplace. They weren't looking at me. I get home about nine. He says, don just told me you're getting fired. They had to tell him. He said they didn't tell me until now because they were worried I would tell you and of course I would tell you so. But nine was the deadline they had for whatever. And I called. Don't brushed me off very quickly. Come in at 8 o'clock, da da da. It was a board meeting. The next day he hands me a one note, whatever. That was my last day.
Unknown Interviewer
So you end up going on the Apple board. Steve recruited you, he seduced you for over a year to join the Apple board.
Mickey Drexler
Yeah. And I say that with all fondness for him.
Unknown Interviewer
What was the Apple board meetings like and what contributions did you make to retail there?
Mickey Drexler
Well, you know, I designed the first store with him because he designed an ugly store. And we went in and I told him, get a warehouse, build a store so we can design it together. So we did a Gap. You have a store before you open it up. So I went in. It was very simple. I said it was too tchotchked. He said, simple. A screen to show the movie or whatever it is. So we designed the store and that's the store. It's still the same store today.
Unknown Interviewer
And the stores became iconic. What's the difference between the first version and the one that we sort of.
Mickey Drexler
Oh no, the first version you never opened up.
Unknown Interviewer
No, but I mean the first version you saw like what it's like comparing.
Mickey Drexler
Apples and oranges or to.
Unknown Interviewer
But I always like to talk about this because we always see sort of the end product. You know, we never see the messiness of the.
Mickey Drexler
What I do, I try to explain this. I have a photograph in my mind. I go into a shop, it paints a picture or it doesn't. One bad color in a great painting. I'm not a big art collector. I love nice pictures, but that changes, throws off the whole painting. It's like the wheels, the ugly wheels on a Mustang. And I mean that every car now has ugly wheels. I can't get over it. You know, you see the wheels. It's like having a bad button on a sweater like this. This is one of our best sellers. And if you put an ugly button on this, that's what you notice. And I say, never give a customer a reason not to buy something. It's one of my rules to, you.
Unknown Interviewer
Know, so why do people buy? Or is it they just don't have a reason not to Buy.
Mickey Drexler
Most people, they don't get it. You know, the logo business. And by the way, I learned this last week, they call it dupes. You know that all the designer copies are called dupes, like in duplicates. Hot business today. Because people say. Well, they don't, you know, the LVs. Who the hell knows if it's a real or fake. You look at all, you know.
Unknown Interviewer
Well, it's interesting because you sort of had. I don't want to say envied, because that's the wrong word, but you liked Ralph Lauren, who had logos. And at J. Crew, you did away with logos.
Mickey Drexler
Yeah, well, Ralph had the horse. And that was. I remember I was a buyer, Bloomingdale's. Ralph had the horse when he just started. And it was prestigious. The horse was prestigious.
Unknown Interviewer
With J. Crew, one of the most fascinating things to me is you took. You did something that's incredibly rare in retail, which was. You took a brand that was known for discounting. Same with Gap, and you made it high end.
Mickey Drexler
Well, Gap was the Gap. Was.
Unknown Interviewer
Was it. I don't know, the early part of the Gap.
Mickey Drexler
Well, you probably. I started there in 19.
Unknown Interviewer
Yeah.
Mickey Drexler
Yeah. I don't know that it was a shithole with the flood. A disaster, culturally, in every other way. It was all on sale.
Unknown Interviewer
What's the Playbook then? To take? I mean, they did it with Restoration Hardware, too. There's a couple of other brands.
Mickey Drexler
Gary.
Unknown Interviewer
I know Gary, but the base rate of success is pretty close to zero in doing this.
Mickey Drexler
It's vision, imagination. Don't have any. Doctor Knows. I call him doctor Knows. Telling you it's not going to work. Look, Old Navy. I went out and I did it.
Unknown Interviewer
It's interesting. You make decisions mostly on your gut.
Mickey Drexler
And research backing it up.
Unknown Interviewer
Well, I was just going to say. But you're always gathering information. Are you pattern matching when you make decisions?
Mickey Drexler
Well, it's funny you use that word. The whole business is recognizing patterns. You know, there's patterns that go on. And for me, I have to preempt the pattern and then I push the team. Like right now, personalization. Two years ago, we had painted dogs on a tote bag. 18 of them that day gone. Two years ago. I have still in the last two years. I want personalization to be what we do. It personalizes the goods. So we have. I don't have my bag here, but painted initials. Cool. The dogs. Painted dogs. But I'm trying to get people to move and it's hard.
Unknown Interviewer
Is the reason that focus groups are so difficult in retail because People are telling you what they want, but they actually have to be led.
Mickey Drexler
They're difficult for me. Everyone else does them, but they don't seem to work.
Unknown Interviewer
Or do they? I don't know.
Mickey Drexler
Look, I don't know. It's not what I do for a living. I do. I say see around corners you have to have a vision.
Unknown Interviewer
It's interesting because the outliers on both ends, positive and negative, don't use focus groups. But everybody's sort of in the. So it's almost like a guaranteed average in a way the world.
Mickey Drexler
This is funny. A friend sends me 20 plus page article 2 weeks ago talking about how average the world is to today. I totally. I called him, I said, wow, you are on. He talked about cars, he talked about designs, he talked this article, he didn't write it. But the world's average and you have to be not average if you want to do what you do. You kind of. For me, you break the rules. But the rules are, you know, common knowledge. Isn't that common, as you know it isn't. And I'm an anti authority guy. I don't like that. I don't like to. I'll never forget when I used to work in the shipping room, I had an idea. You know, I used to ticket. You know how you see those hang tags on buttons. So I used to walk around bending down with the racks of coats like this. I took a rolling chair and I'm going down the aisle. It was like my father got so angry at me. He wasn't my. Who knows who my boss was. But that's what happens in corporations. No one wants to change the rules in a way. Not that he was a corporate guy.
Unknown Interviewer
Well, this is interesting, this is a fascinating sort of like nuance here because in a corporation you can't get fired for following the rules. Rules. I just follow what you told me to do. So I'm absolved of all responsibility or judgment, right? Like nobody's going to get fired for following the rules. I mean, you do at the CEO level, but aside from that, you're basically.
Mickey Drexler
Well, you have to. You can follow the rules. On the other hand, you have to have a drive in you that's creative and can make changes. When I worked at the department stores, you know, I'll never forget I had some simple ideas for the financial person. You know, none of them, they didn't ask people. I asked people. You know, they know young people don't have any baggage.
Unknown Interviewer
Well, this is fascinating because you say you're anti authority. But when you say that, what I hear is you're not anti authority. You're really a rule breaker who's constantly questioning things which comes across as anti authority. But you're vacuuming up information from every available source.
Mickey Drexler
And when I hear something two or three times, I bring it to work immediately. Every weekend I have a Monday morning weekend update. What is it? It's a combination of me seeing things that are an idea I look through. Not that I like the fashion magazines, but I look through every picture on monthly. And if there's a picture I like, I cut it out last weekend. It was a great picture. It was a designer. I think it was Fendi. And they just showed the women's heads and they had a sweatshirt on each of them in four, in bright colors. So I cut that out and I said, this is something we will do while we are doing hooded sweatshirts in bright colors. And then I, you know, I always do detective work. I'm addicted to detective shows. Great, great detectives solve cold cases. There's such a difference. Anyway, I, then I asked someone who I know, I said, are there any companies we can do a collaboration with? We do collaborations with. We get together. And, you know, when we did it at Jake, we kind of invented it. Now everyone's, they're all collaborating with all the famous brands. So it doesn't make it unique. But anyway, so she mentioned this company in England. I went online, looked at it, and they had a hoodie hat, a Bacalava, whatever it's called. So I said, we're going to do that hat. We sell a million casualties. We are hats. We're famous for that. And by the way, being famous for something drives businesses because you're dominant.
Unknown Interviewer
But Hermes uses this with the Birkin bag. I mean, that drives almost all their.
Mickey Drexler
Other businesses, I think. Well, it's funny, with Hermes, I used to get Peggy when I could afford it. And I was a young guy who had money and I started to afford things in my 40s, which is young now to me. But I collected for Peggy twice a year, anniversary and birthday. I got Birkin bags or Kelly bag or whatever. And. But people, you know, I think designers. So anyway, she has a beautiful collection. Now she doesn't wear them because she thinks they're old ladyish, although she's an old lady and she doesn't want to wear them on the streets today. You know, like watches, they see your watch and they come up to you. But anyway, Birkin bags, now they're dupes of that. And I said, now Growing up in the Bronx, I didn't know from fancy, but growing up in the Bronx, I, you know, liked things. When I bought my first pair of Gucci buckle loafers, I was probably early 30s. I used to go to the factories. So I went to the Gucci store in Florence. I got those shoes. Boom, Bada bing. Now you don't know the difference between a dupe and the real and you get ripped off.
Unknown Interviewer
How much of retail do you think is theater?
Mickey Drexler
Theater? Well, Stanley Marcus, Neiman Marcus was known for that. I don't think it's, you know, the hottest supermarket in America now. Erewhon. Yeah, I was in one in LA about three or four weeks ago. I don't call anything theater. Theater is great product. Looking like a painting and going in. For me, I never had Old Navy, by the way. It was an amazing business in its day. I had Schwinn bikes around the escalator. We sold out of them very quickly. And then the guy I knew who owned, he's an investor, not a close friend. But Schwinn decided not to sell us because we weren't buying them from dealer, but the business. First apparel business to hit a. What was the number? I think they hit a billion dollars. That's the first one in apparel. But now I'm sure there's many others. But I just followed the guidance of. Yeah, but I also absorb detectives. I always come in every day, I say I see these. I'm addicted to true crimes.
Unknown Interviewer
You're always gathering information. You're always looking, you're always questioning patterns and probing, which helps you develop the patterns.
Mickey Drexler
And I see a picture.
Unknown Interviewer
Yeah, Who. Who do you think are the great retailers today?
Mickey Drexler
I don't like to name competitors, but I'll tell you some. Well, TJ Maxx, I always name Carol because Carol Meyerowitz. TJ Maxx is the honest discounter and she's a great merchant. The only thing is you have to keep changing. Act's the wrong word, but you gotta keep changing and seeing down the road. And I have these ideas, but you.
Unknown Interviewer
Can only do that if you touch the territory. Like when you hopped on the plane, you went to the store. When you're constantly talking to everybody, when you're getting all the information sources, that's how you rapidly adjust because you're not looking at a.
Mickey Drexler
If you are not curious. In any field, whether it's non profit, profit selling cars and all that, any field product is always driving and product is about emotion, in my opinion. Someone said this the other day and I kind of took it on myself to say it. I have a love affair with the companies that I've been involved with. You know, madewell. You know what happened, how I got that name?
Unknown Interviewer
Yeah.
Mickey Drexler
So David Mullen, who's worked. He's a great wash guy. Unfortunately, I was old friend. Friend. Ten or 15 years ago, I was a J. Crew. Well, you know, how Old Navy and the whole concept. I told you. So David has a logo, Madewell since 1937. He shows it to me. It was actually the logo. He said, what do you think? I said, it's fantastic. He said, well, do you want to buy it? I said, if the price, yeah. What about you? We can't afford. I bought the name. I owned the name. And when we went public at J. Crew, then we did madewell. And I had a vision. I loved work clothes then, like Carhartt and all that, but I had a vision for it. But you can't do anything well unless you have the right team. So we struggled for the first three or four years. We're going to do men's and women's, and I decided, let's get rid of men's now. I didn't have anyone to talk to about this other than myself, but I never thought about it that way. So we got rid of men's. And then Somsack, who works with me and us, creative guy was at J. Crew for 15 years. And he left for a year, hired him back. He became the creative director of madewell. Boom, boom, boom. And madewell was a great company until it wasn't, you know, when we had a $2 billion. Well, don't even get me started with selling companies because the mercenaries. And by the way, at Gap, you know, when I left there, I didn't say that no one called me on the board. 18 years. Hello.
Unknown Interviewer
Wow.
Mickey Drexler
Can you believe that?
Unknown Interviewer
Except for Steve, who didn't think you should be fired in the first place.
Unknown Advertiser
Right?
Mickey Drexler
Exactly. Exactly.
Unknown Interviewer
What makes something a classic look?
Mickey Drexler
Yeah, it's a good question. I always say, if you know, you know, I wear clothes that have no expiration date. This shoe, I found it in Paris. It's Alden, an American company. And I must have been 40, probably 40 years ago. It was my favorite store, Fastenhob, until they were bought out by a big American department store. Then it's over. So this shoe is from Alden I've been wearing. Not this one shoe. We used to buy from Alden at J. Crew. And my good friend Todd Snyder, who's a men's Designer. He buys from Walden. And I asked him about a year ago, I said, can you ask them to do a special this shoe again for me? I ordered 10 of them.
Unknown Interviewer
That's awesome.
Mickey Drexler
I wear this and I wear another one. This jeans never go out of style, but as long as you don't wear the big ones, the skinny ones. These are cashmere socks that we started doing at J. Crew. They whatever. And now we do them. This is clothes. This scarf, it's 40 years old. Michael Drake was a good friend. I used to buy from him in London. His collection. There is a Michael Drake now, but it's not the same. I have about 20 versions of this. I bought him wholesale because, you know, and this sweater, this is our third year at Alex Mille, but forever. And it's cashmere. And our prices on cashmere are good. Oh, I only do vintage watches because I like vintage and old is new. Today, the vintage business is this way. And it's unique. You're not like, buying. You're not going to see. Well, a hooded sweatshirt never goes out of sale. Now that's a novelty. So, you know, I don't know.
Unknown Interviewer
I love this idea. Clothes that have no expiration date.
Mickey Drexler
No expiration date. Right.
Unknown Interviewer
No expiration date. Farnam street, the website that I run, is about knowledge that has no expiration date.
Mickey Drexler
Really.
Unknown Interviewer
So it's timeless wisdom.
Mickey Drexler
Timeless. And it's whatever I wear and it's things. And I didn't learn this. Everything I buy, and it's internal to me. You know, it's like if someone wears something, oh, that's the guy with the purple shirt, or that's the car with the ugly hubcaps. I like discreet, I like style, and I like a uniform. That's what I do. And I wear the same Alex Mill slub T shirt, blue, every day.
Unknown Interviewer
Perfect.
Mickey Drexler
No, I've always had a uniform.
Unknown Interviewer
We always end the interview with the same question, which is, what does success look like to you?
Mickey Drexler
I think what it looks like is a couple of things. If you can impact people's lives in a positive way, that to me is the most. The best sign of success. And of course. And if I could also be very pleased with myself, that's another sign. But I think the biggest compliments I get are from people. You know, we had that. I think you knew about the Gap reunion. Did you mention that to me? No. 150 or 60 people were there. Ken Pilot, who used to work with me. And I am. I don't. Success, it's not being rich, only it's not even being rich because I know successful scientists or successful whatever, but I think it's impacting people's lives. My biggest compliment, I say this, I've said it on cnbc, is when I'm called a mensch. You know what that word is?
Unknown Interviewer
Why don't you explain it for everybody?
Mickey Drexler
So everybody knows mensch is in Yiddish. Mensch is like a nice person, normal Hamisha, down to earth. And I like talking to people in a parallel way and not. I don't talk down to people because I appreciate who I am and what I do. Now. No one escapes. You know, I go through certain mood issues. Of course, I'm always trying to better myself, but I think success is. It's just not about money. Most people might say that, but you have to be. I'm very pleased with what I've done, more so over the last few years, because I have changed people's lives. I had a reunion two weeks ago last week with the field team at gap, you know, 15, 20 of us. And they all thanked me and they said they made their lives much better. And that's success.
Unknown Host
Thanks for listening and learning with us. For a complete list of episodes, show notes, transcripts and more, go to FS Blog Podcast or just Google the Knowledge Project. Recently I've started to record my reflections and thoughts about the interview. After the interview, I sit down, highlight the key moments that stood out for me, and I also talk about other connections to episodes and sort of what's got me pondering that I maybe haven't quite figured out. This is available to supporting members of the Knowledge Project. You can go to FS Blog membership, check out the show notes for a link and you can sign up up today and my Reflections will just be available in your private podcast feed. You'll also skip all the ads at the front of the episode. The Farnum Street Blog is also where you can learn more about my new book, Clear Turning Ordinary Moments into Extraordinary Results. It's a transformative guide that hands you the tools to master your fate, sharpen your decision making, and set yourself up for unparalleled success.
Unknown Interviewer
Learn.
Unknown Host
Learn more at FS Blog Clear. Until next time.
Summary of Episode #213: Mickey Drexler – The Art of Selling with Retail's Merchant Prince
The Knowledge Project with Shane Parrish features an insightful conversation with Mickey Drexler, a visionary leader in the retail industry. As the CEO of major brands like Gap and J. Crew, Drexler shares his profound understanding of consumer psychology, brand building, and the art of merchandising. This summary captures the key points, discussions, insights, and conclusions from their engaging dialogue.
Mickey Drexler begins by reflecting on his challenging relationship with his father, which significantly shaped his ambitions and personal drive.
Mickey Drexler [00:58]:
"I think my ambition comes from being the opposite of him. I think I always lived in my fantasies escaping where I am."
Drexler describes his father as emotionally distant and unsuccessful, contrasting sharply with Drexler's own aspirations. This tumultuous upbringing instilled in him a desire to excel and avoid replicating his father's shortcomings.
Drexler's career trajectory is marked by pivotal roles that transformed major retail brands. Starting with 12 years in department stores, he transitioned to leading Ann Taylor in 1980, where he navigated significant challenges without formal training.
Mickey Drexler [04:38]:
"After 12 years in the department stores, I couldn't find the stimulation and the excitement... I always depended upon my gut, my instinct."
His tenure at Gap from 1995 to 2002 was particularly transformative. Despite an initial stock drop of 50%, Drexler led a comprehensive renovation of all 430 stores, eliminating old merchandise to free up capital and reinvigorate the brand.
Mickey Drexler [10:42]:
"You have to take and you gotta get the cash out of bad goods. It's like rotten fish or whatever. So we redid the stores."
Drexler emphasizes that successful retail isn't merely about selling products but about selling dreams and aspirations. He believes customers seek to transform themselves through what they wear, aligning with deeper psychological desires.
Mickey Drexler [00:00]:
"What I do, I have a photograph in my mind. I go into a shop, it paints a picture or it doesn't."
This philosophy drives his meticulous attention to detail in merchandising, ensuring that every element of the store contributes to a cohesive and appealing vision for the customer.
Rejecting conventional methods like focus groups, Drexler relies on his instincts and pattern recognition to anticipate consumer desires. He advocates for vision and imagination as key drivers of innovation in retail.
Mickey Drexler [35:40]:
"It's vision, imagination. Don't have any... It's about having a sense of what's going to sell."
Drexler shares stories illustrating his approach, such as redesigning product names to be more intuitive and ensuring merchandise aligns with the brand's identity. For instance, he insisted on naming a pajama pant "boxer short" instead of a more convoluted term to maintain clarity and customer appeal.
Mickey Drexler [26:51]:
"You want to name things that say what it is. And I go through this all the time. They confuse people."
Drexler's collaboration with Steve Jobs highlights his ability to blend retail expertise with technological innovation. Together, they designed the first Apple store, focusing on simplicity and user experience.
Mickey Drexler [31:56]:
"I designed the first store with him because he designed an ugly store. So we did a Gap... We designed the store and that's the store. It's still the same store today."
This partnership underscores Drexler's commitment to creating iconic retail spaces that resonate with customers and stand the test of time.
Throughout his career, Drexler emphasizes the importance of surrounding himself with capable and genuine people. He values team members who are honest, creative, and aligned with the company's vision.
Mickey Drexler [13:10]:
"You can't teach anyone. I am a huge proponent and I never could say, like, Jesus, they're the president, they're the CEO, they're the this."
He believes in empowering his team to make decisions and trusts his instincts to identify talent, fostering an environment where creativity and innovation thrive.
Leading Gap through a turbulent period, Drexler learned critical lessons about maintaining vision and competitiveness. He stresses the necessity of being relentless in competition and continuously evolving to stay relevant.
Mickey Drexler [21:29]:
"You must have a vision. You must be whatever's defined as a good merchant. You must be spot on and be a pain in the ass because the best bosses, and I always say, hire your boss because that's the one."
His establishment of Old Navy exemplifies this approach, creating a distinct brand that capitalized on market gaps and consumer desires.
When discussing success, Drexler outlines a philosophy centered on positively impacting others' lives and maintaining personal integrity. For him, success isn't measured by wealth but by the meaningful contributions he makes.
Mickey Drexler [51:39]:
"If you can impact people's lives in a positive way, that to me is the most. The best sign of success."
He highlights the value of being recognized as a "mensch," a Yiddish term for a person of integrity and honor, underscoring his commitment to ethical leadership and genuine relationships.
Drexler advocates for timeless wisdom and continuous learning, drawing parallels between enduring fashion and perpetual knowledge. He believes in adopting uniformity and simplicity in both personal style and business practices to achieve lasting success.
Mickey Drexler [50:49]:
"It's timeless wisdom."
Mickey Drexler [50:51]:
"I wear the same Alex Mill slub T shirt, blue, every day."
His approach underscores the importance of consistency and adaptability, ensuring that both products and strategies remain relevant in a constantly evolving market.
Drexler concludes by emphasizing the importance of intuition and curiosity in driving innovation. By constantly seeking out new information and questioning established norms, he stays ahead of trends and fosters a culture of creativity.
Mickey Drexler [39:54]:
"I see a picture."
This relentless pursuit of knowledge and understanding solidifies his reputation as a merchant prince who not only anticipates market shifts but also shapes them.
On Vision in Retail:
"What I do, I have a photograph in my mind. I go into a shop, it paints a picture or it doesn't." [00:00]
On Ambition and Personal Drive:
"I think my ambition comes from being the opposite of him." [03:58]
On Merchandising Simplicity:
"Keep it simple. I took out the stupid." [24:59]
On Success:
"If you can impact people's lives in a positive way, that to me is the most. The best sign of success." [51:39]
On Timeless Wisdom:
"It's timeless wisdom." [50:49]
Mickey Drexler's insights offer invaluable lessons for anyone interested in retail, brand building, or leadership. His emphasis on vision, intuition, and genuine impact provides a roadmap for creating enduring success in business and beyond. By blending personal anecdotes with strategic wisdom, Drexler exemplifies the art of selling dreams and shaping consumer desires, making this episode a must-listen for aspiring entrepreneurs and seasoned professionals alike.