The Knowledge Project with Shane Parrish - Mickey Drexler: The Art of Selling with Retail's Merchant Prince

Episode Date: February 4, 2025

This episode will transform how you think about style, aspiration, and the art of knowing what people want before they know it themselves. From working in department stores to advising Steve Jobs on Apple’s retail strategy when it didn’t have retail at all, Drexler’s career traces the evolution of American retail itself: from local shops to mall dominance, from catalog to digital, from mass market to personalization. Whether you’re an aspiring entrepreneur, a retail enthusiast, or someone looking to build a brand that stands the test of time, Mickey shares invaluable insights on what separates truly successful brands from the rest. Mickey Drexler is the chairman of Alex Mill. Before that, he was the CEO of J. Crew and sat on the Board of Directors of Apple. He founded Old Navy and Madewell, and served as the CEO of Gap from 1983–2002. Learn why gaining real-world insights—and not just reports or data—is crucial to staying ahead of the competition. Newsletter - The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at fs.blog/newsletter Upgrade — If you want to hear my thoughts and reflections at the end of the episode, join our membership: ⁠⁠⁠⁠⁠⁠⁠fs.blog/membership⁠⁠ and get your own private feed. Watch on YouTube: @tkppodcast (02:16) How Mickey Drexler became Mickey Drexler (07:04) Lessons from redefining Gap (12:47) Merchant, defined (15:17) How Drexler evaluates stores (19:20) Lessons from running Gap (21:19) On Old Navy (27:26) On Steve Jobs and Working with Apple (33:00) Re-making J. Crew (37:00) Drexler's superpower (43:40) Current-day retailers who are great (45:10) How Drexler got "Madewell" (47:15) What makes something a classic look? (50:20) On success Learn more about your ad choices. Visit megaphone.fm/adchoices

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 is 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. I'm your host, Shane Parrish. 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 prints, Drexler could walk into a room with 100 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 opportunity 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.

Let's start at the beginning. You said your father was a model of what you didn't want. 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 when you're a kid,

like you moving all over the place, you don't know what. right and what's not right. You learn over time. What was that relationship like? He was, 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? It was, I didn't know any better at all. And I thought this is what the father is like. And over the years, I learned that this is not what a good father is like. And he was an angry, bitter guy.

He was not successful. And 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 ironies, 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. How did that affect you?

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. So, but, you know, it affected me. He never took any pleasure in my success. And I, he just never did. Was there a moment when you realized he wasn't a big shot? Well, I'll tell you, it's an interesting story. I used to work, he worked in the garment coat company. He worked buttons. He had kind of a low-levelish job. Well, I didn't want to face

that. And he, they asked me to take the payroll of 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 looked 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 just got subways, the Long Island Railroad, and I had to escape from the house. So I luckily got into, I didn't know where to apply, State University of Buffalo, some guy I knew when, there 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 a department stores. And then I was very lucky, fortunate. I was called to run Ann Taylor then in 1980. I was a young guy. 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,

you know, 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. And tell me more about that. 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 in 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 five 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, this, 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-interest in people in this world, plenty of them. Why do you think we're so risk-averse? Well, I can't answer for others. I think, you know, Why? I don't, 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. And they, well, salary, they don't want to risk that. They don't want to risk, I mean, they get very wealthy these days becoming a CEO. When you transformed the gap, you renovated all 430 stores at the same time with no focus group, nothing. Oh, my God. If you take over something, you've got to 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, and I'll never forget. We were talking about, it was a year and a half, we were in Carmel, and we were sitting there, we come up with a kind of a bankruptcy plan. That's when I started to get nervous.

And I've been there a year and a half. We, 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 got to take and you got to get the cash out of bad goods. It's like rotten fish or whatever. So we redid the stores. With Amex Platinum, access to exclusive Amex pre-sale tickets can score you a spot track side. So being a fan for life

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No powders, no blenders, no shakers. Starting at 17 grams per medium latte, Tim's new protein lattes, protein without all the work, at participating restaurants in Canada. What gave you the confidence to do that? I mean, this was like a, we're basically going to go extinct, so that's the base case.

Those two or three years, even when it turned around, was like, uh-oh, but I worked my ass off. I kept, no one taught me how to run anti. Taylor, I just did it without any supervision because the headquarter, it was $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 I, in the department stores 12 years, I kept looking for the right place to go. 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 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, Barbara, 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. What does it mean to be a merchant?

What it means to me is, and it's not a lot, I think. It means to have no, 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 rearview mirror. Most people do rearview 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. The word that comes to mind, though, is, like, taste. Well, that's a good question. What's the difference between? 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 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.

what it is vision right 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 uh-oh and I didn't follow my instinct and really hurt one of the companies you know there's people involved so 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. 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 merchandising the store. Five minutes. Three minutes.

What would you look at? The picture painted because when I, 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 colors very important. And when I did Gap, I had a list of styles. I was trying to start something. I was looking 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.

So it's interesting. Coming back to your friend's comment about, well, the customers deciding what we sell, if you're selling, if your game, I guess, is to sell the most product of 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's like escape the competition in a way. 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 are. 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 T.J. Max, my friend there, Caroline, she's the best.

You can go to T.J. Max 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, I'm self-taught. And then I'm also very curious. When I joined Ann Taylor, Brooks Brothers, and I saw it declined 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 mark down. 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 designed them with them. And we had Ann Taylor Studio label. Now, no one told me to do that, but, you know, do, do, do. It's the white space. It's, 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. 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 their seven years?

You know, well, the bureaucracy is, I'm all over everything. They, they, I took every call from a customer and they'd be surprised. about, you know, if, 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.

Yeah. And, you know, now I do that. It's a little bit of a payback because I never had anyone like that. What were the key learnings from the gap? Like, what are the key lessons that you take away? 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, it 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 you know how I started that it's my favorite 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 like to read about business

because I wanted to be who they all were yeah and then I realized well I didn't realize for a long time who they were but not what I wanted to be so that There was a little article buried on page four or five about Target. 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 know, because you got to, you know, only the paranoid survive. Well, that's interesting, right? Because it's a story of only the paranoid survive. And Andy Grove is the one

who wrote, that book. But it's also a story of making sure that you're touching the mediums. 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. 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. You know, people, for me, I identify with those people who aren't the fancy people. You know, a 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, The time we plugged it in and turned it. It's like first you've got to do updates. Second, you've got to sign up for all these accounts. Keep it simple.

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. And the best way to do that is to actually use your own product. Yeah, yeah. We did the PGME's pajama thing, which is a really fun thing. It's going to 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 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 it. It is what it is.

Everybody has an idea of what it is. Of course. Everyone knows it's an elastic waste. And I said, continue that, and you're not doing this, whatever it was. And that's what I do. Yeah. 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. Everybody wants to come up with something new. They don't know, but they're not. logical they don't yeah so what happened at the end of the gap in your tenure there oh well you Steve Jobs like just to frame the conversation here so Steve Jobs is on the board he calls you yeah take me through this 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 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. What was he like as a board member? 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'll he wasn't very popular but I just you know guy was ill he was dying I just so admired him and I really admired him a lot and Johnny I was his lunch made 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, and 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 back seat 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 Marquis 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. That's the name. They didn't like the name. Long story short, two naming, I don't like agencies and I don't like consultants. And the Old Navy, by the way, that was started to a whole other story. So let's go back to the firing. So Jobs is calling you. 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. I looked at Eric. 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. But nine was the deadline they had for whatever. And I called Don. He brushed me off very quickly. Come in at 8 o'clock, dot, dot, dot. So board meeting the next day. He hands me a one note, whatever.

That was my last day. So you end up going on the Apple board. Steve recruited you. He seduced you for over a year to join the Apple board. Yeah. And I say that would all fondness for him. What was the Apple board meetings like and what contributions did you make to retail there? 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. We did a gap. You have a store before you open it up. So I went in. It's very simple. I said it was too chocky. 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. And the stores became iconic. What's the difference between the first version and the one that we sort of? Oh, no, the first version, you never opened up. No, but I mean the first version you saw, like, whoa. It's like comparing apples and oranges or tomatoes. But I always like to talk about this, because. Because we always see sort of the end product.

You know, we never see the messiness of the... What I do, I try to explain this. I have a photograph in my mind. It's... 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 is 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, you know. and you can now get almost anything you need for your sunny days delivered with Uber Eats. What do we mean by almost? Well, you can't get a well-groom lawn delivered, but you can get a chicken parmesan delivered. A cabana? That's a no, but a banana, that's a yes.

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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. Do 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 real or fake? Nobody knows. You look at all, you know.

Well, it's interesting because you see. 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. Yeah, well, Ralph had the horse, and that was, I remember, I was a buyer of Bloomingdale's, Ralph had the horse when he just started, and it was prestigious. Right. The horse was prestigious. 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 well gap was it was it i don't know the early part of the gap well you probably i started there in 1984 yeah yeah

i don't know that it was a shithole with the flat a disaster culturally in every other way it was all on sale What's the playbook then to take, I mean, they did it with Restoration Hardware 2. There's a couple of other burns. Gary, I know Gary. But the base rate of success is pretty close to zero in doing this. It's vision, imagination, don't have any doctor knows. I call them Dr. Nose telling you it's not going to work. If I look, Old Navy, I went out and I did it.

It's interesting. You make decisions mostly on your gut. And research backing it up. Well, I was just going to say it, but you're always gathering information. Are you pattern matching when you make decisions? Well, it's funny you use that word. The whole business is recognizing patterns. It's, 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, who, what we do, it personalizes the goods, you know, 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 yeah so is the reason that focus groups are so difficult in retail because no people are

telling you what they want but they actually have to be led they're they're difficult for me everyone else does them but they don't seem to work I don't... Or do they? I don't know. Look, I don't know. It's not what I do for a living. I do...

I say, at the sea around corners, you have to have a vision. 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... This is funny. A friend sends me 20-plus-page article two weeks ago. talking about how average the world is 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 tick it, you know how you see those hang tags on buttons. So I used to walk around bending down with the racks of cars. 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. 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. You know, 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 well yeah 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 and when i worked in 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 ask people i ask people You know, they know young people don't have any baggage.

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. 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 woman'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. Well, we are doing hooded sweatsharts 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. 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 bakalava, whatever it's called. So I said, we're gonna do that hat. We sell a million cash and we are hats. We're famous for that. And by the way, being famous for something drives businesses because you're dominant.

How much of retail do you think is theater? Theater. Well, Stanley Marcus at Neiman Marcus, was known for that. I don't think it's, you know, the hottest supermarket in America now. You had an ear one? Yeah.

I was in one in L.A. 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, you know, 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 it. First one in apparel, but now I'm sure there's many others.

But I just follow the guidance of... Yeah. But I also absorb detectives. I always come in every... I see these... I'm addicted to true crimes. You're always gathering information. You're always looking.

You're always questioning and probing. Yeah. Which helps you develop the patterns. And I see a picture. Yeah. Who do you think are the great retailers today? I don't like to name competitors, but I'll tell you some names. Well, T.J. Max. I always named Carol, because Carol Myrovitz, T.J. Max is the honest discounter, and she's a great merchant. The only thing is you have to keep changing, acts the wrong word, but you got to keep changing.

and seeing down the road. And I have these ideas. But you 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... If you are not curious in any field,

whether it's nonprofit, profit, selling cars and all that, At 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, made well, you know what happened, how I got that name. So David Mullen, who's worked, he's a great wash guy, unfortunately. He's an old friend. 10 or 15 years ago, when I was a J-Crew,

well, you know how old Navy and the whole concept, I tell you. So David has a logo made well 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 prize, yeah, but what about you? We can't afford it. I bought the name. I owned the name, and when we went public at J. Crew, then we did Maine well. And I had a vision. I loved work clothes then, like Carhart 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 yeah but I never thought about it that way so we got rid of men's and then Somsak who is

works with me and us creative guy was at a jku for 15 years and he left for a year hired him back and became the creative director of made well boom boom boom and then made what 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, Gap, you know, when I left there, I didn't say, no one called me on the board, 18 years. Hello? Wow. Can you believe that? Except for Steve, who didn't think you should be fired in the first place. Right, exactly, exactly. What makes something a classic look? 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 probably 40 years ago, it was my favorite store, Fasenob, 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 and Jay 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. That's awesome. 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 is 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 them wholesale because, you know, and this sweater, this is our third year at Alex Mill, but forever. Yeah. And it's cashmere and our prices on cashmere. Oh, I only do vintage watches because I like vintage and old is new today. Yeah. 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 style now. That's a novelty. So, you know, I don't know. I love this idea clothes that have no expiration date. No expiration date. No expiration date. Farnham Street,

the website that I run is about knowledge that has no expiration date. Really? So it's timeless wisdom. 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, I don't, it's like if someone wears something. Oh, that's the guy with a purple shirt. Or that's the car with the ugly hubcaps. I like the street.

I like style. And I like a uniform. That's what I do. And I wear the same Alex Mill. You know, slub t-shirt blue every day. Perfect. You know, I've always had a uniform. We always end the interview with the same question, which is what does success look

like to you? 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 CMBC is when I'm called a mensch you know what that word is Why don't you explain it if everybody's everybody knows? MENCH is in Yiddish. Mench is like a nice person, normal. Hamisha, down to earth. And I like talking to people in a parallel way. And 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 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. Thanks for listening and learning with us. For a complete list of episodes, show notes, transcripts, and more go to fs.com. Or just Google. That's 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 slash membership, check out the show notes for a link, and you can sign 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 Farnham Street blog is also where you can learn more about my new book, Clear Thinking, 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. Learn more at fs.blog slash clear. Until next time. Thank you.