👕 “American Crew” — Interview with Mickey Drexler, ex-CEO of The Gap & J.Crew

0:01Mickey Drexler: Yetis, untuck your T's and cut off your quarter zips. Because today's guest is the former CEO of The Gap, J.Crew, and the Apple Store, basically. That's right. We're interviewing Mickey Drexler, the inventor of all American style. Old Navy? He launched it. Made well jeans? He created it. Outdoor voices? Yeah, he chairmaned it. If George Washington needed corduroys, he'd probably call Mickey D. The Mickey D, because Mickey's style is so fundamentally American, he makes Ralph Lauren look Canadian. Besties, no one in business has influenced our national wardrobe quite like this man. So when Steve Jobs launched the Apple Store, he asked Mickey for design advice.

0:38Mickey Drexler: And no big deal? Yeah. Mickey was on Apple's board for 16 years. 16. So he was basically Steve Jobs' boss. And in the age of AI, his tastemaker status has never been higher. Because this is the mind who made khakis cooler than jeans by tweaking a stitch. So today, on top of his wild career story, Mickey will tell us how we got the American uniform we are all wearing right now. And he'll tell us why ignoring the data is the patriotic thing to do. Oh, and how to beat AI? You gotta be cool. He's the pharaoh of fashion, the chairman of chinos, the prince of the popped collar. Jack, how about Miranda Priestly of American Prep?

1:12Mickey Drexler: I'll take that. Does that work? That works? Besties, please welcome Mickey Drexler to the best one yet. This interview is the best looking one yet. Mickey great to have you with us I mean that is exciting high energy and I'm I'm in it we gotta print that on some leather turn that into a purse so we did some research on you Mickey and the thing that jumped right out to us is that you made a cameo on the Breaking Bad TV show how do you pull that off that was my proudest moment I'll tell you the story you edit a lot of this stuff anyway so I'm having lunch with a friend years ago. And he said, do you ever hear of Breaking Bad?

1:54He says, watch it. So I watch it and I'm in love. I'm addicted. So I call a friend of mine who then worked for Sony who owned the whatever. And I said, Rob, this is the greatest show in the world. Does anyone know about this he said well it's doing very well i said it's fantastic so he introduces me to the ceo of whatever the entertainment company was got a little friendly with him and after about a year or so he says would you like to do a cameo on breaking bad sold i said no a year later you're like i don't want to go to new mexico it's hot because i get nervous about things like that And he said again, I said, why not?

2:44It could be fun. So I go to New Mexico. I go to the trailer, and I was in the trailer. Nine takes. I was a customer in the car wash.

2:55Mickey Drexler: Customer number two. Yeah, and the irony is. Wait, were you a customer to get your car washed? Yeah, I was getting my car washed. Okay. Or for the other business. The real car wash place. And I was getting the car washed. and I went to pay and it took nine takes. Only two were my fault. And she gave me the people that were laundering the money. Yeah. You know, her and Bryan Cranston. So she says, oh, excuse me, you gave me too much money and she gave me back the overpayment. And these are people who have the cash loaded in the safe at the car wash. So the irony is she was honest with me. Yeah.

3:38And so that's it. Not bad. Not too shabby for a fashion guy. It was fun. Well, I'm not a fashion guy. I am who I am, you know. Now, a quick word from our sponsor.

3:52Mickey Drexler: Gusto. One sec, Yetis. We just need to take a break from the pod for a moment to find that I-9C3 IRS tax form for each employee. And then, Jack, we got to make sure each coworker is countersigned, I think. Oh, yeah, yeah. And then we have to track down each employee and make sure they know their health insurance options. Oh, right. Did everyone know open enrollment ends tomorrow? Nope, no one did. Yetis, we are just podcast hosts. We also run a media company here and full-time employees mean full-time benefits too. Which means roughly 46 ,000 forms, documents, and tasks to process for each team member.

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6:09Mickey Drexler: So you're a New Yorker is what you are. And we're interviewing right now in New York City, home of Jay Peterman, fictional fashion guy from Seinfeld. Jay Peterman, I thought he was from Chicago, but he was fantastic. Well, he's also Elaine's boss in Seinfeld. And he's famous for the urban sombrero. Remember that? Yes. Oh, he was amazing. And Ralph Lauren, famous for the polo shirt. So what article of clothing is Mickey Draxler famous for? And I should point out, Jack is famous for the linen shirt ever since he got back from his Italy vacation. It's all he's been wearing. I'll tell you what I'm most proudest and hope I've become famous for.

6:47we, Alex Mill, is the lanyard holding the iPhone and the leather is Italian leather. The phone lanyard. Yes. Yetis for everyone just listening right now, not watching on YouTube, Mickey's wearing a extremely fashionable leather strap around his neck, like a necklace that's holding his iPhone. It's an alternative to a fanny pack. It's part of my uniform in a way. It's a manny pack. And I never leave home without this. it's on and around all day every day because or else I misplace my iPhone.

7:22Mickey Drexler: Brilliant. Speaking of Ralph Lauren, he's one of what Nick and I are calling the Bronx Bombers. Yeah, yeah, yeah. You, Calvin Klein, and Ralph Lauren all born in the same borough of New York City within five years of each other. So what was it about that moment and that place that led to three of the most iconic names in American fashion? Well, you know, I appreciate that, but I never planned it and still even today I have a hard time. Did your parents plan? My parents, my role model, no. And, you know, I did a little research on Calvin and I found that interesting story because I always, those were the two, they were the ones.

8:06Calvin and Ralph. And then there was Perry Ellis and a few other people who were amazing. And Calvin's grandmother was a dressmaker. Okay. She sewed, she tailored, she was a dressmaker. Checks out. His mother was extremely stylish and had a lot of style and taste. And his first job was working for a coat manufacturer in New York. And he was in a freight elevator one day with the coats on a rack. A woman from Bonwet Teller who was a merchant buyer said, I love those coats. Where can I get them for Bonwet Teller? He said the name of the company, and she said, who designed them? And he said, I did.

8:53Wow. So that was that. He quit his job. He went to start this company, a design company with his partner then, and that's the beginning of it. But then you were a Bronx kid who's into math. You went to Bronx Science, which is like the ultimate math public school in New York City. How did you get into that same industry? I don't know. I always cared. I don't know where this came from, but I always cared about how things looked. And I think it's because I lived in my fantasies a lot because I didn't like living in my home a lot. And I'd run to my cousins down the street. I was always escaping my environment.

9:34and I think part of the creativity comes from the fantasy and the escape because I didn't want to be there and my mom was ill my father was what he was and so it was very depressing for me so I always like daydreamed a lot in school I was in I never liked school I daydreamed in school about things and how things maybe should be. So in terms of getting in, I worked in the garment. One good thing my dad did is he not graciously made me work. Yeah. And I worked in the shipping room of the coat company and I put tickets on, coats on the buttons, and I worked hard. I went to get coffee, a chop full of nuts.

10:21I did whatever they wanted, and I always took my work, as I do today, very seriously. And I pushed myself. I didn't know all this then. And so I was in a Garmento world. I sold razor blades. First time I ever did an entrepreneurial thing. There's Wilkinson sword razor blades then.

10:41Mickey Drexler: The razor blade was called a sword? No, Wilkinson sword. It put a sword on your face. It could have run with that. And I don't know where I found this out, but they were the best razor blade. You could hardly get them. It's kind of like Coors Beer. Mickey's a good salesman. I'm interested in this razor blade now. So I sold them on the street because I bought them, I don't know where. And I had a little side hustle. Nice. Anyway, that was a minor thing. So I did that and I worked always Saturdays and I always was forced to work. But it was good. It was very good. And so I'm a worker. And I never give up on things now, now, a million years later.

11:25but getting into the business I did that and when I was in college I got a summer job at Abraham and Strauss a now defunct department store group they're part of the Bloomingdale's group etc and I went and I had nice summer salary it was in Brooklyn and I loved Ken Hirsch the buyer of jeans and I had a great time I was working all day being part of the mix I had to do a project and why millinery was going out of style. I did that. And I did seriously. So after that, they liked me a lot. And this is interesting. In your life, a moment or two will change your life. So having worked at Abraham and Strauss, I thought, oh, when I finish college, they all liked me.

12:17I knew the team. I'll work here. So I interviewed. And then a guy in my class, I don't even remember his name, said oh can you set me up with an interview at abraham strauss so i called the head of uh hr who i knew and uh he said oh sure so i run into the guy later on i was back at school or whatever he says well thank you i got a job offer at abraham strauss for eleven thousand five hundred a year. I was offered$11 ,000. I was effing furious and I couldn't explain to myself why, but that led to me interviewing at Bloomingdale's, taking the job. And that was 11 ,500. Now, $500 was no small thing for me.

13:08I had no money, but I liked the interviewing. I liked the environment. I liked the people I met and there was a great energy. And by the way, I always tell people, you got to feel that for a company you want to work for. Oh, you're a competitive guy. Actually, one thing Jack and I noticed was you had these early insights in the fashion industry. Like when you get your big break at Ann Taylor, you said that your muse when you were having clothes made and designed was Jackie Kennedy. What is a muse exactly? We've referenced it on the pod and should every business, no matter the industry, have a muse?

13:43I have, she was in those days, the fashionista with her sister, whose name Lee Razawil. And I would, she, her kid went to school in the upper, well, her kid who I knew then, went to school in the Upper East Side at Brearley. And I lived on East.

14:04Mickey Drexler: Is her kid JFK Jr.? No, no, it was her daughter. Okay. Carolyn. Yeah. And, but she was in that neighborhood and I lived in those days in a not nice apartment on East end in 81st street, a little, you know, whatever. And I would see her once in a while around the neighborhood. I followed her once because Jackie Kennedy, you know? Yeah. And I always, and I sent her, I knew she lived at 1045th Avenue. So she was on the catalog list. She never bought a thing from us. But you'd still send her the catalogs. Oh yeah, of course. Even though you knew they were getting rejected every time. It doesn't matter.

14:45You know, to me, she was who I felt I wanted us to be. And that's what a muse is. And that's what a muse is, yeah. And does every industry need that? Like every business, should you have a muse who you're designing for one person? I can't answer it because a muse has a lot of different definitions. She was an inspiration. And then over time you have inspirational people. It's not a democratic process on who becomes a muse. It's someone who inspires you. It's what they do. It's what they design. It's emotional. Yeah. An emotion to me has always been the driver of my world and the world. And I always say to people, emotional is – they say, why do you like someone or something?

15:36I said, I can't explain it. I said, why don't you like chopped liver? It's like, how do you explain it?

15:43Mickey Drexler: How do I explain why I like linen shirts? Yeah, you don't have to. So, Mickey, you're a hardworking kid from the Bronx. You're emotional. You fantasize about things you don't have. You basically started in the mailroom. You worked six days a week. And eventually, you become the CEO of Ann Taylor at the age of 39? 35. 35. But what makes you famous to the American public, to the fashion industry, to the business pages of the Wall Street Journal, is you take over the Gap. Yes. The famously 1969 Gap jeans in San Francisco, California. And you were the turnaround artist. Well, I don't like that word, but go ahead.

16:23Mickey Drexler: Tell us what was happening at The Gap and what you did to fix the company. You fixed it from$400 million in sales to$14 billion by the time you left. I didn't leave voluntarily. Spoiler. Right. I was fired with one day notice. First of all, the first three years I was there, we went from an apartment on the Upper East Side to San Francisco. It was Peggy. My son, Alex, was then six years old. Last day at Ann Taylor was a Friday. I was on a flight Sunday, checked into a hotel there. And I'm thinking, I was so nervous, anxious, ended up being quite depressed for the first few years, adjusting to the environment, the culture, and San Francisco.

17:15go. I stayed at Campton Place. I take a cab who knew from Ubers or cars. And it wasn't like I had an apartment, which is was fine. I was checking in and out of a hotel every weekend for six months. Oh, I don't know. But I never thought about, you know, negotiating the big shot move that people, oh, I got an apartment. So I went to the office. Now, this is the other cultural shock. Ann Taylor office was on 57th Street at the corner of Fifth Avenue above the Ann Taylor store. I go to San Bruno office park. First time I was there and like. Is that south of the city? Yeah, it's south. Oh, and the view is the airport.

17:59Not glamorous. No. And it hit me. What the F am I doing? And it was extraordinarily difficult for me and for Peggy to adjust. And then working in San Bruno in a strange culture, and the gap was fall into the gap. I used to remember it on the ads. And there I was. I fell into the gap. Yeah. And I got there, and I can only say the adjustment. Personally, I was very depressed adjusting. to this public company where the stock was dropping because I was taking markdowns, where the founder was my partner across the hall reminding me, you can't take this. And he was okay, and he built all the stores.

18:49It's a great partner. But I would commute to the city and back, and the people in the company, they say, oh, there's the noon flight to Hong Kong. Because he could see the airport. No one would believe this. You need the airport schedule. And I'm looking out and I was there Monday through Friday. I started Thanksgiving week and my family and my – Peggy and Alex moved in June. And I would commute every week.

19:23Mickey Drexler: And it was like, oh, my God. So back then, the company had$400 million in annual sales. That's a little more than Allbirds did. I never really thought of it as a famous name, as I felt about J.Crew. Fall into the Gap was crappy, but famous. And I didn't like it. You know, at age, I didn't know from anything other than what I thought. So what was the first thing you did at the Gap? I sized up the culture very quickly. In fact, the first visit I took, I went to, and this says it all in a little way. So I travel around. So I rented a car. I rented cars. I was in Houston, Texas. I wanted to see the stores.

20:11You have to talk to people on the ground with customers. But for some reason, I end up in Houston Galleria. It wasn't fun to travel. But there's a drive I always had, and I wanted to win the race and get there. So I walk in. So I'm in the parking lot. I see windshield flyers on every windshield. So I look at it and says, today only 30 % off at the gap. Oh, boy. That tells you everything. So I walked in. Hector was the store manager. I'll never forget. I, Hector, I'm Mickey, da, da, da. I said, what's with the 30 % off? Oh, we do that when business gets slow. That's all you need to know. Discounting desk by all that.

20:52Everything was discounted. Fall into the gap. Levi's two for 26. Everything was on sale. So what I did, I always do this. I mean, I get together with team and I look at all the merchandise. I do that first and I meet the people because without the right team, I can't do this alone. No one can do anything alone. So I religiously, intensively went through every single style we owned. And I knew what I was up against. I mean, but I didn't, you know, but all I could think of what has to get done, I didn't think about what the fuck am I doing here. Yeah. But it was part of that. And I was miserable because the challenges and the culture and everything about it and having a founder across the hall where the company's stock is dropping.

21:45And he said to me once, he said, well, you know, we're going to have a terrible earnings report for the first quarter because you're taking all these markdowns. I get emotional and I, you know, but he was okay. He didn't mind. I said, if we don't take markdowns, we'll have no cash to pay the bills and buy fresh goods. You've got to convert it anyway. So the stock dropped, it probably dropped in half. and now I'm running a public company and it was a nightmare. It was pure. So what did I do? I had a list. The first thing I did there is every time I spoke to someone, I had no idea what they were talking about.

22:26And I knew that if I don't know what they're talking about, then no one does. Yeah, that's a different language. So I put on every desk in headquarters, you know, there's a keep it simple, stupid. I put K-I-S, keep it simple. Yeah. a plaque on everyone's desk. I don't know if it did any good or not, but I said, I don't understand what you're saying. And so I just day by day dug in through great personal difficulties more than anything. And I just did what I had to do. You purged the bad inventory that wasn't selling. That was your first move. And I went to Levi's and said everyone in the world was buying washed Levi's except Gap, who started on Levi's only.

23:14And they're doing rigid washed Levi's, two for 26. And I went to Levi's and I just changed. I said, we're buying the washed goods. So you improve the jeans to be Levi's quality at least.

23:27Mickey Drexler: Then you eventually launch Gap Kids. And, you know, it's funny. I'm a Gap Kids alum. And it's popular these days to say that you grew up chubby. People think it's like a cool thing for – yeah, they do. They really do. Jack keeps telling me this. Especially when you're handsome, good-looking, and great shape. I was chubby. So I have a litmus test to see if people were really chubby when they were young. Here's the trivia question, which I hope you know because you launched Gap Kids. What is the largest boy's jean size that Gap Kids makes? Every childhood Husky kid knows the answer to this question.

24:00I don't know the answer.

24:01Mickey Drexler: 16 Husky. That's big.

24:07Mickey Drexler: I clung to those 16 huskies because I didn't want to go to the men's department I was only like 11 we started Gap Kids for the following reason and it was a big mistake we made no money in that business really? even with Jack's family? he has three brothers who are in this husky boat crew cuts both mistakes hard to make money too distracting on kid stuff I thought parents would be willing to pay. We thought that was a profit puppy. The reason I did Gap Kids, I used to take Alex shopping. Your son. Six years old. Every, before nursery school, I got him his wardrobe. It was always an Oshkosh by gosh overall, which still would be great if they have, and a plaid shirt.

24:51So I went to Emporium, which was no more. It was a department store in San Francisco. doing the back to school shopping, I guess in September or August with Alex, who was going into the first grade, I couldn't find anything to buy, nothing. And I had a meeting back at the office and part of it's the white space. You don't learn this, how to do this. So I got together, the mothers, because most of them were women and mothers, a couple of fathers. And I said, is everyone tell me about your experience buying kids clothes at the end of the meeting i said to myself we're doing gap kids so why did that not work to make a kids say you want that shirt in kid sizes it's expensive all the details are the same except it's less fabric it didn't work and kids is very much a kind of a discounty kind of business yeah but in the early days we should have stopped at 10 or 15 shops, maybe.

25:54And then it's a distraction. The more things that you have to do, the main thing is the main thing, and kids wasn't the main thing. Interesting. Same thing with J.Crew, in hindsight.

26:08Mickey Drexler: So after Gap Kids, you would go on to launch something that worked really well. Oh, yeah. This was like the OG disruptor of fashion. It became the fastest fashion brand to hit$1 billion of sales. First brand to feel like 50 bucks, but really cost 15. Old Navy. Yeah. Old Navy. This is a very interesting story and it could take up the whole podcast. I'm serious. That's my favorite. Well, Madewell too was another interesting story and all of it's about how I felt. I don't want to hear negativity on this, that. So one day I used to read the New York Times business section when it was worth reading.

26:48It's 25 years ago, whatever. And there was an article in it buried, maybe page four. It was, there was a quote, Dayton Hudson, now Target, was starting a company called Everyday Hero. And it would have prices named, someone was quoted cheaper, less expensive than Gap. Oh boy. So it's basically a Gap knockoff. A dupe. I get on an airplane the first week it opened in mall of america i said i want to see what's coming here because you know i i'm always threatened by it this is a great story i want to reset the scene

27:23Mickey Drexler: here talk to me so the predecessor to target was launching something that was obviously intended to undercut the gap a gap dupe the early gap dupe and so you went to target's home state of minnesota read the article yep because only because you read the article page four of the And if they didn't have that quote, there'd be no old neighbor. And you're the first guy to scope the product and say, this is a threat to the gap. So you kind of faced the innovator's dilemma there. No, this is a threat. No, when I walked in after 10 seconds, I then said, I'm not worried. Okay. But Dayton Hudson, because we were part of the same buying group at Bloomingdale's or wherever, they always did a lot of research.

28:07focus groups this that i don't do any of that because i don't believe in it i said you know dayton hudson does a lot of research to myself you talk to yourself i said i wonder what went on with this thing and i stopped off in chicago on the way back to saint sent one day and i visited two stores that were in lower demographic locations i wanted to visit the stores and i schmooze. So I went into the first shop and this wasn't a planned strategy. It was just, oh, I'm going to go to a little detour on the trip to the Midwest. I always speak to the store people. I said, why do you have so many markdowns here?

28:48She goes, as people said, they can't afford our clothes. And I said, wow, bingo. Did the second store in another Chicago area. Same thing. bingo. Get back on an airplane. And when I got back, I don't know how I found out this statistic. Gap genes were 3450. Every other gene in America under 30 was 80 % of the marketplace. And we didn't play in that arena. We were 3450, maybe to 4450. That was a bingo. And then when I got back, because you want to know from the people. So I gave, I don't know, it was a lot of years ago, I think maybe 200 bucks to 10 people of demographic salary and all that who worked at the Gap.

29:35It was a big corporation. And I assigned them discount stores. And I said, go and shop Mervyn's. Kmart was then. Walmart. Shop. And it was stores that are out of business. Just go spend money. And I said, spend it. And I think I gave them a category. I'm not sure. About a week or two later, they're back. And I had, you know, it was 10 of them or so. And I went around the table and I said, report now every experience you had. They all talked about clean stores. I asked them, I used to say, Walmart used to have 987, 1322. I said, does it matter that they have odd prices? Weird pricing, yeah. We don't care.

30:20We just want a good value, good price, and nice clothes, clean stores. And we went around and I'm thinking, and the white space I felt early on was respect to all customers, no matter if it's discounting or not, treat people with the respect or whatever you call it. And at the end of that meeting, I was sitting there with a fellow I worked with, Jeff. I didn't talk to the company about this. It was kind of my own little project. and I said to Jeff, I said, we're doing this. And that was the beginning of Old Navy. And how'd you come up with the name? So we didn't have a name. I'm in Paris. Have you heard the story?

31:05No. So I used to go to Europe. You get ideas. Being creative is exposing yourself and seeing things that inspire you in everything. and that's why I was inspired by this thing for need. The phone lantern. The phone lantern on your shirt. I was in Paris driving back to the airport with a woman I worked with. I'm in the back seat of the taxi or whatever on Rue Saint-Germain and I saw a head like a movie marquee with lots of little neon bulbs and we just drove by. I said to Maggie, I say, that's the name, Old Navy. That's what was on. It's a dive bar. Old Navy's named after a dive bar in Paris. Yes.

31:56That you saw in a taxi ride. And I checked the next day back in New York or California. Call your lawyers up. No one owned it. Yeah. So I registered immediately. Now, we talk about things in corporations. The board didn't like them. Oh, boy.

32:15Mickey Drexler: you know and the board the board's your boss yeah right right they can fire you and they probably want to do a focus group on the name yeah it's totally common yeah hire consultants i mean it's totally common in that sense but you won that battle i'll tell you how i i battled for a lot of things when you have a family controlled business i say they were great partners but it wasn't always so easy as so the gap was a publicly traded company yeah but but a san francisco family The lock was controlled by the family. And I'm still friendly with the three sons of the founder. But so they didn't like the name Old Navy.

32:58And then they said they – I'm not mentioning names because there are names involved here. That's fair. And they said, well, the gap's famous and no one's going to know what Old Navy is. I said long story short you know what the store opened up being called? What? Gap Warehouse Old Navy That was the original name I don't like I don't like Gap Warehouse It's very wordy and it does not roll off And I said there will be no gap in five years Yeah You called the Pepsi the Coke and dot dot dot

33:34Mickey Drexler: Yeah This kind of reminds me of J.Crew Factory which I also don't like because because I bought For the record When I was strapped for cash, I bought J.Crew factory sweaters thinking they'd be J.Crew quality. But it wasn't. No. Never. And I think a similar thing could have happened to the Gap there. If it was called the Gap warehouse and people bought it. Oh, of course. Then the Gap… You're cannibalizing your business. That would have cannibalized it. Right. And it was a different thing too because the Old Navy did have more surprising things. Like I have a bag that's made out of basketball leather.

34:05Like it has the little dots on it from the Old Navy. That never would have been a Gap product. I still have it. I still get compliments on it. You know, and this is one of the things I'm most proud of at Old Navy. The first store that opened in Manhattan was on 18th and 6th Avenue. And I fell in love then with Schwinn bicycles. They were all very retro. They were this. So we had a Schwinn bike department around the escalator. At Old Navy? Yeah. Sold out probably the first three or four days. Wow. And then I knew the owner of Schwinn Corporation. They said, we can't sell you anymore because the Schwinn dealers want people to take the bikes back to them.

34:51The Schwinn's, they're all yellow. So I still have one in my garage. Sold out. But that's the kind of thing. The unexpected is always better than the expected in anything. My family went to that Sixth Avenue store and did like, we would do hauls. And you could spend like six hours there finding something like a bag shaped like a basketball.

35:10Mickey Drexler: Did old baby have shopping carts or were there big bags? I'm remembering big bags. It's a good question. I don't remember. Or you were getting all the Husky clothes. Your family was loading up with the four sons. I did make a mistake. I always wanted to have a little coffee shop in a shop. So we put on the second floor. We got together with this restaurant guy who I'm still friendly with. We opened up a coffee shop. Well, launching kind of cooler sister brands Underneath the big parent companies. Kind of your thing. Yeah, like Madewell is like a multi-billion dollar jeans brand. All American brand right now.

35:44But it started in this insane way with you like personally buying the name.

35:50Mickey Drexler: TLDR. Mickey moves on from the Gap to J.Crew. And Madewell is his baby. But before you started J.Crew, you personally acquired the name Madewell. How did that go down? Well, I have a friend, may he rest in peace, Dave Mullen. Great guy. He was a wash expert in jeans. He worked with us at Gap and then J.Crew. Terrific. His job was, he was a wash expert. He's a ripped jeans connoisseur. I have a faux tear in my back pocket. Yeah. That was precision that he did. That was his art and his sign. So David calls me one day. We met and he shows me a wooden sign with Madewell logo. It's wood. And since 1937, he said, what do you think of the name?

36:47I said, I love that. Madewell. Madewell. It was an old workwear company, defunct, in New Bedford, Mass. Wow. So he said, would you want to buy it? I said, depends on the price, because he wasn't in a position to do anything with it. And I said, yeah, I would like to buy it. Oh, and the price? That was very - Can you share the price? It was$125 ,000. So you bought the name Madewell, which was based off a factory in New Bedford, Massachusetts, for$125 ,000. You personally just bought it because you liked the sound of the name. And finding a great name like Old Navy, it's a great name. Yeah. A name has to belong to the product.

37:32Namestorming. And it's, what do you call it? Namestorming. I like that. Yeah, coming up with the names. But if you think about the name, even when we name products, I want every name to be personal in a sense. Because they're your friend if you remember it. And I'm trying to get the team to now just say, like when we did Ludlow Suits at J.Crew, it was Ludlow Street. Yeah, in Lower East Side. And, you know, I want things to be named after streets, after this, after names that connect. It reminds me when we interviewed the Harry's founder, he said branding is attention and it's a feeling at the end of the day.

38:08And each of those names, you don't need to know what they sell. They give you a feeling no matter what. Everything is emotion if you look at something that you want to buy. I measure. I said emotion is the most important. I don't know if it's a secret sauce. Yeah. But my heart, I said I have something inside here that tells me the bell goes off or whatever. Now, a quick word from our sponsor. Walmart business. Yetis, we cover business trends on our show, and they move faster than you can spell GPU.

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40:28Mickey Drexler: Ready to transform your customer support? Go to decagon.ai slash tboy to get a personalized demo and see what Decagon can do for your team. Check Decagon out at decagon.ai slash tboy. That's decagon.ai slash tboy. So, Mickey, you have gotten your big break at Ann Taylor, Jack's mom's favorite brand. You've transformed the publicly traded Gap Company into a$14 billion - From a loser to a winner. Behemoth. Then you launched, created, invented Old Navy after a taxi ride in Paris, and you personally bought the Madewell name and turned it into the coolest jeans brand in history. But we want to talk about perhaps the coolest moment we're aware of of your career, which is a phone call you get from Steve Jobs.

41:18Yeah, because you've just been at a wine party in Napa, whining and dining and schmoozing with the guy. You know, Steve. And to this day, I couldn't love him more. And just so smart, driven. And we lost a great asset in this world from him. So we met at a birthday party in that, but we had a home there. He was at the party, dot, dot, dot. And we schmoozed. And I'm thinking, you know, Steve Jobs, you know, we're schmoozing. That dot, dot, dot was a lot of cool stuff happening.

41:56Mickey Drexler: Was his black turtleneck a gap? No, no. Was he wearing it at the wine party? He was a Japanese designer. He wore New Balance sneakers and Levi's 501 was his uniform. Okay. But we met. And, you know, Steve was, this is many years ago. So you two bond over both being micromanagers. Right. Well, his mission, he had a mission. And for a year, we chatted. And I said no about joining his board. Because, you know, at that point, I was stupid. Steve Jobs asked you to join the Apple board. And he said no. No, that is stupid. You said he denied the job. Because as far as I'm aware, being a board member of a publicly traded company is$300 ,000 to$600 ,000 a year in salary.

42:46Mickey Drexler: It's a good gig. For six to 12 meetings a year. Am I summarizing this incorrectly? There's all the stock there, options. Not too shabby. I'm always very fortunate and lucky. I didn't think about that part of it. But, you know, it's a real part. So after a year, he calls me up and says the magic words. He said, if you join my board, and he hated boards, I'll join the gaff board. I said, deal. And the reason is they're all insiders. I had no say. I knew Steve, if nothing else, would be Steve Jobs. Irreverent? A little rude? late or not showing up. Uh-huh. And it only lasted until I was fired. It was about a year.

43:39And he's the one. So anyway, he wanted me to design the store. What store? The first Apple. He had a story show and he was really ugly. So Steve Jobs shows you a design for this Apple store concept and you think it's ugly. It was ugly. Wow. And I said, there's too much going on. Keep it simple and let it be timeless. And let the product speak. So I suggested we get a warehouse and build a store in the warehouse. Like a real potential Apple store. Which we designed together. And he had an architect, whatever. And then we did it. And it was the same store as today. Yeah. Because timeless for me in clothes, in design, never goes out of style.

44:29But I got to ask you. we've all been to the Apple store. The Apple store has not changed in decades at this point. It's the same - Wooden tables, white walls, a lot of beautiful glass everywhere. Yeah. Jack and I always say retail's not dead, bad retail's dead. What is it about the Apple store that you designed? What resonated? What is the eternal deep feeling that we all get walking to an Apple store that's the reason that Apple hasn't changed them in the 20 years since he design you know it's kind of like the chopped liver question there's no answer to that it's kind of you feel it's it's it couldn't be simpler more classic and it'll never go out of style and style never goes out of fashion fashion can go out of style because fashion's of the moment You build something that looks right and perfect.

45:22You can't improve on the best. And I think I'm not saying, you know, because I designed it or whatever, but Steve and I, that was it. Let the product speak for itself and don't look at a busy background, this, that, and the other. Keep it simple, stupid is what I always say about everything.

45:42Mickey Drexler: That would have been such a great Instagram collab post. when you and Steve Jobs announced you're moving into each other's boards. Oh, yeah. That would have been great. I can picture the photo out there. So, Mickey, you brought Steve Jobs to the Gap board. He's brought you to Apple's board. And then the Gap fires you. They give you a one-day notice and you're gone. Steve called me first. He did? They wouldn't tell him because we were friends. And he, you know, as Steve is, he didn't go to the board dinner the night before where I show the goods. I knew the turnaround was in. We had a bad year or whatever.

46:18So I get home at 9. He goes, call Don. You're getting fired tomorrow morning. Wow. I said, no wonder they didn't look at me at all tonight. We were showing the best goods. I knew it was a turnaround. You know, and there's three companies, you know, and I looked at all that. And, of course, so I go and I get handed a one-sentence piece of paper. whatever. Next day was my last day. But you bounce back from that and you kind of get the last laugh because you end up at J.Crew and you end up taking them public eventually.

46:56Mickey Drexler: But all of the growth that you sustained at The Gap transitioned to J.Crew once you started there. And The Gap started flatlining, right? I think The Gap's still doing the same volume they did 20 years ago. Yeah, about$16 billion. The first thing you did at J.Crew, we noticed, though, was you did something we've never seen another CEO do. You put a PA system into the headquarters. Loudspeakers. Loudspeakers. Like on every floor, you know, this is Mickey chiming in. Like the principal in the middle school. Happy Friday, everybody. I didn't do it before. Why? What is it? Because that seems like a micromanager kind of move.

47:32I am proud to be a micromanager. okay you do this and you speak to the people who speak to the customers now the thing with the the loud speaker what happened i get there they're ready to go whatever j crew a disaster and i get there and they have an office for me a closed office i sat there for a day i'm bored out of my fucking mind i'm trying to get people i call people voicemail this and that and you know something the clock was ticking there it feels like it's wasting time and so i said i moved my office into an open space right outside the closed office because i hated being there alone and i was in the middle which i did a gap towards the end and um i said i want a loud speaker because

48:25Mickey Drexler: no one's returning my call well mickey we're publishing this episode on america's 250th birthday. Well, the annual tradition of the Old Navy American flag tee, that is literally American style because you splattered it right on there. But we see you as also the more general visionary of American style and fashion. So more broadly, what is American style, Mickey Drexler? I don't know what it is. I know what style is. But about American style, I think to me, style is defined by what I feel or what this, you know, designing a store or designing a car. You know, look to me, the greatest brand in the world in cars is Jeep.

49:14They haven't, I mean, if you think about Jeep should be the number one car, utilitarian, a workhorse, you know, consistent. And, you know, the, the Jeeps, they redesign them except maybe for the uh old-fashioned one you know the grand wagon i mean the woody they should still be doing a jeep woody oh that would be classic what's old is new today give them old and it's new why do you think vintage clothes look like crazy yeah first of all why pay the prices look at designer clothes pricing and what do you get for it's like we say the 20-year rule of nostalgia you know the nostalgia moment becomes novelty i would love to have a jeep brand see The same thing connects to Gap and J.Crew in a way.

50:02There's a sense of brand and emotion and what you have to do, try to bring it back. Well, there is one catch there, and it's something Jack and I call the three Fs of fads. We believe, after studying business news for 10 years—

50:18Mickey Drexler: At daily shows, we've told you. That fitness, food, and fashion, the three Fs, are the three industries most vulnerable to fads. time and time again, we have seen that in fitness, food, and fashion, what's hot today probably won't be in a few years. As a Lululemon shareholder, I can tell you that firsthand. So we were curious, as a fashion leader, do you agree? I'm sick and tired. What was the vegetable that everyone was eating? Was it kale? Radicchio? Are Brussels sprouts still in? We're asking the production team. You know, just... But it's true. As you can't... I don't like being in that business.

50:55But you're in that business. So how do you, yeah.

50:58Mickey Drexler: You know, a lot of stock market investors might avoid these industries because it's seen that it's not possible to sustainably be profitable. You always hit a wall. But if you don't reinvent, but see, I look at products. Well, look at the Levi 501, 1849. You know, they can't kill it. It hasn't changed. That's timeless. That's unique. But no, I don't think that way. I think, look, I've hit fads. My mistakes. Fast fashion was a fad. I blew it on this. And then I have a bad year. Stock market punishes you with a bad week. Everyone's forecasting earnings. But I don't think that way. If I did, I'd get into trouble.

51:42So the way you defy fads is just constantly reinventing? Because I can, is that the answer? I'm trying to think what a fad is. There's a million of them out there. I look at some, without mentioning names, I look at names on a sweatshirt. It's a fad. It'll die quickly. If it's a name on a sweatshirt. Because the more you show people of scarcity and they don't want to see themselves coming and going. Look at the designer logo business. It used to be, in my opinion, all due respect to my friends who were designer people, not at that level anyway. You see it coming and going. When I was a kid, young guy, starting out, it was a big effing deal when I bought my first pair of the Gucci buckle shoe in Florence, the slip-on or whatever.

52:32I walked down saying, I'm rich now. You know, because it was, but now what's unique is scarcity. And it's no longer scarce? Well, nothing, a logo unscarces. I mean, you know. But I can see your style of reinvention right now because for the Yetis listening, Mickey's coming here impeccably dressed in a classic Alex Mill fashion style. But he's also wearing this leather lanyard to hold his iPhone, which you would never associate with that brand, but which they also sell. That's constant reinvention. In this case, you design for an iPhone case. And the hard thing about this business is you've got to keep doing it.

53:14Okay, but then how do you make that decision? Because what we find fascinating is Jack and I always ask our guests, you know, how do you make decisions? Metrics versus magic, information versus intuition, graphs versus guts. How much of it is imagining versus engineering? Do you go with your gut? All of the above. But it starts with vision. Do you look at the data, basically? Of course. The data tells me everything I need to know. I was very good in math, not science, probably. But, you know, if you look at, I don't know if AI does this, you feed in information that's today, it'll forecast it out.

53:52But what I do on every style, I say, what could you have sold if you didn't run out of your two best colors? Data is religious to me. Best sellers every single day tell me a story. Every day I'm nagging them to buy more of the best colors because it's not a democracy when it comes to colors or things you sell. And Navy, we're out of Navy some things. I said, what's the most famous popular color for men in the world? It's Navy. And then they buy, and I asked this morning, the first question I said, how many of these did you buy of this color? And I said, give me the numbers. And they said, well, how many?

54:40I said, you should have bought at least 40 % of the buy in this color. How do you know that? You know it. So 90 % of your decisions are data-based? They're always part of, because it's DNA. I look at the information. That's your gut. I always look at what's sold, even if it's three or four years old. And then there's a gut, bring this back. On this one, it was, once we got it, it was data-based. And if you sell 150 of something, you have to say, not forecasted, how many would I have sold if I didn't run out of stock in a week or two? And that's the data that you need to look at. It's the things you didn't have and you have to estimate.

55:26And it's not a science, but you have to forecast how many you think would sell. And then you have to protect the downside. But data is absolutely, for me, religion. Mickey, you mentioned AI a moment ago. And there's a quote, Jack, and I love that you said. You said, AI will not write songs that move us. So why can't style be automated? Can AI just not have taste?

55:54Mickey Drexler: It doesn't have emotion. It can have taste. Well, one thing AI could not do is play a salesman on Breaking Bad season two. It couldn't have pulled that off. Never. and I got$100 for that. And the residuals keep coming in. The checks keep coming in. So, Mickey, to wrap up your epically fashionable resume, Abraham and Strauss, Bloomingdale's, Ann Taylor, The Gap, Gap Kids, Old Navy, J.Crew. You've covered every generation here. We'd love to wrap it up with some rapid-fire questions. Yeah, we got some special ones whipped up, Riff. What is a timeless fashion piece that every man needs? Five pocket pair of jeans that fits him in the right wash.

56:36He needs white shirts. See, I wear this shirt. 2014.

56:46Mickey Drexler: You bought that in 2014? You still wear it? It's custom from Hong Kong. They need white shirts. They need classic blue and white striped shirts. I always have the argument, blue and white striped, men and women, they sell the best. He needs, I like fun socks now. The best timeless fashion piece every woman needs. You know, and I'm not a fashion designer. I think apparel, it's all about simple, elegant. No one wants to walk around saying, oh, they're wearing that purple shirt. You don't want to be the guy or the woman. Color is critical. and I'm not qualified to say that. I know it when I see it, always.

57:35But, you know, I like things that are forever.

57:38Mickey Drexler: What's the best fashion brand that's not one of the ones you've worked for? Which doesn't leave many by process of elimination. I'll tell you who I say the best fashion brand is. TJ Maxx. Oh. Stock's ripping. $60 billion. They have real prices. And if you look at our industry today, I always say, don't give them the credit card when you're buying something. Go online first to see where I can buy it for less. Best business book you've ever read? You know, I just finished Phil Knight's book, 10 Years Too Late. Shoot out great book. I'm not a big reader, but I like that. I like to stick with the detail.

58:18What's the best restaurant in New York City? I have none. Best. I don't have the best. Best restaurant in the Bronx? Well, it's probably on Arthur Avenue, but I don't go there anymore. What about the restaurant where you control the playlist? Oh, San Ambrose. Oh, lovely. I like that. Princhy Pace Cake. Yeah, you know, that's - Best business leader you admire? Well, I loved Steve. Steve, the best. And he was quirky and difficult, but he cared about the products that was first and foremost in every board meeting. He'd cover it with a gray cloth and then he'd make the presentation. Wow. And look what he's done.

58:59Mickey Drexler: I miss him. We miss him too. And if you, Mickey Drexler, were a stock and we're going to IPO, you personally, what would be your three or four-letter ticker symbol on the stock market? That's a hard one. You know, Shu, I think we should tell everyone to drink every time he says simple. So maybe SMPL. Yeah, SMP. Coat? Coat works too. Yeah. Or Hamishah. That's too long. And finally, Mickey, before any guest leaves, we always ask them to whip up the takeaway. So what's the takeaway on Mickey Drexler and American fashion? I never had a grand plan to be who I am today. In fact, when I'm objective, I'm quite anxious about keeping it up.

59:52so every day I have to beat myself and what I did yesterday so the takeaway is it ain't easy to do this and be true to the business and yourself and a lot of angst goes with what I am and what I do but make today the best one yet oh yeah like I every day I want to beat myself not beat, but every day I need to do better than I did yesterday. Every day. And I explain that to people. Well, Mickey, as a profound micromanager, we've agreed to hand over this recording to you so you can pick it apart and choose the parts that you prefer. Oh, really? Is that what you do? Thank you, Mickey.

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1:00:50Mickey Drexler: True story. Couldn't risk getting sick. I didn't want to be groggy. I couldn't afford a hangover. It was New York, baby. Okay, but Jack, celebrating the wins is what we do. And so for our live shows, we crack open something special. So we drank Biro, the premium non-alcoholic beer brand co-founded by Tom Holland. Yeah, I actually first saw it at my grocery store. Delicious tastes like a celebration. Feels fantastic and looks legit. More on the looks in a sec. And if it's good enough for the actor who played Spider-Man, it's good enough for us. You see, it pairs well with a pickleball game, a profitable earnings report, or with the best podcast.

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