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Mickey Drexler
CEO of Drexler Ventures, Drexler Ventures

Retail Legend Mickey Drexler: From Building Gap & Old Navy to Running Alex Mill Like a Startup

📅 May 06, 2026 The Retail Pilot - Leaders & Legends Podcast 69 MIN 5 VIEWS 133 SEGMENTS · 3 SPEAKERS
Retail icon Mickey Drexler built Gap into a $14 billion empire, founded Old Navy, and revitalized J.Crew. Now at 80, he's running Alex Mill like a scrappy startup—and he's never been happier. In this episode, Mickey reveals: ✓ Why he got FIRED from Gap after building a $14B business (and what he should've done) ✓ The "white space" strategy he used at Ann Taylor, Gap, and Alex Mill ✓ Why focus groups are "the enemy" and led to his biggest mistakes ✓ How he runs Alex Mill with only 30 people (vs. hundreds at Gap) ✓ His weekend update ritual: clipping magazines and finding inspiration everywhere...

What Mickey Drexler said

Written from the verified transcript and checked against it. Every figure links to the moment it was said.

Mickey Drexler, chairman of Alex Mill, discussed the brand's growth from a small startup to a business with two stores, Soho and Upper East Side, and about 30 wholesale accounts. He emphasized the importance of owning the brand, citing lessons from Ann Taylor and Brooks Brothers. He reflected on his career, including transforming Gap into a $14 billion company, launching Old Navy, and his firing from Gap with no notice. He highlighted Alex Mill's small team, less-is-more assortment strategy, and the role of mentorship and intuition in retail. He also talked about his weekend update meetings, marketing integration, and the balance between designers and merchants, stressing data's role but not over-reliance.

Key takeaways

  1. Alex Mill has two stores, Soho and Upper East Side, with about 30 wholesale accounts, and the business has recently gained traction after five difficult years.
  2. I made a mistake opening Hemisphere and hiring wrong senior executives, but Old Navy more than made up for it.
  3. I was fired from Gap with no notice, and the next day Don Fisher told me he made a mistake, but I never confronted the board.
  4. I lost interest in international expansion at Gap and J.Crew because focus groups reinforced what I didn't want to do.
  5. The David jacket at Alex Mill got buzz from word-of-mouth and influencer mentions, leading to attempts to offer it in both men's and women's.

Numbers and commitments

FigureWhat it refers toTypeAt
14 billion Gap's revenue at peak, still same today metric 1:11
about 30 Wholesale accounts for Alex Mill metric 1:59
20ish Team size at Alex Mill earlier, now 30-ish metric 1:59
$295 Retail price of Alex Mill's cotton blazer price 28:22
$225 Price of sold-out painted totes (20 sold in two days) price 40:28
33% to 35% Share of Levi's goods at Gap when Drexler joined metric 17:32
25 million to 75 million Ann Taylor sales growth during Drexler's tenure metric 7:56
20 to 50 Ann Taylor store count growth metric 7:56

Chapters

  1. 0:00Alex Mill business overview
  2. 7:56Early career and Ann Taylor lessons
  3. 17:32Gap transformation and Levi's exit
  4. 22:43Small company management style
  5. 28:04Assortment planning and less is more
  6. 35:03Weekend update meetings
  7. 40:28Marketing and tote bag story
  8. 49:24Mistakes and regrets
  9. 53:57Dealing with contrarians and hiring
  10. 58:23Designers vs merchants and advice

Questions asked in this interview

12
  1. 7:33... those with whom I speak you're in the minority I hear more things around challenges the customers slowing down people are concerned with what they're buying but you're realizing success where are you seeing the success within the business?
  2. 17:27Wait, were you were you were you researching the company at this time or were you working?
  3. 29:14What did you see that's exciting and reinforces things?
  4. 44:58How do you work with the teams to really understand what fits in the store and the story you're going to tell in the store and how product is going to speak to the customer?
  5. 47:44And it's the question of how do you know?
  6. 52:28Is that related to just how much we did around opening stores and how aggressively we grew the business?
  7. 53:28Do you have one on the team?
  8. 53:59... think it's this.' Do you have somebody that can bring you back because you can be very passionate, very compelling, you've got a point of view, more, more, more, edit, edit, edit, and then someone says, 'No, I like this.' Do you have that?
  9. 58:23There was no report out, 'We need an iPhone.' And all of a sudden, there was an iPhone. It was what was next?
  10. 1:03:12Number one, what are you streaming now? What are you watching?
  11. 1:03:49So what do you like? What show?
  12. 1:06:40When getting dressed, what item do you start with?
Ken Pilot 0:04 ↗
Rock helps retailers make more of every transaction. When someone is already buying online or in-app, Rock makes it possible to show relevant ads and offer content in that moment like subscriptions, upgrades, or loyalty perks. So instead of interruptive advertising, customers see something more useful and more timely. For retailers, that creates more value from the transaction. For customers, it creates a better experience. That's Rocked. Making every transaction more valuable. Welcome back to the Retail Pilot. I am lucky to have my good friend and retail icon Mickey Drexler back on the podcast today. Mickey began his career at Bloomingdale's, reinvented Ann Taylor, the man who dressed America, transformed Gap into a 14 billion cultural icon, founding Old Navy, then revitalized J.Crew and launched Madewell, now chairman of Alex Mill. This Bronx-born merchant prince shaped decades of American style. Mickey, welcome back.
Mickey Drexler 1:06 ↗
Thank you, Ken. Nice to be here and thank you for that very kind introduction.
Ken Pilot 1:11 ↗
Well, I mean, I don't even know if you need an introduction, but for those who don't know what you've done, which is a lot, now they know. And it's also interesting to note, Mickey, that it says here it was a $14 billion business. That was back in 2001, 2002. It's still a 14 billion dollar business today, but that's for we'll talk about that later. Okay. So Mickey, Alex Mill, it sounds like you've been riding a little bit of a wave. You've got some wind in your sail. Tell us a little bit about the business, but I'd love for you to start at a high level to explain the business in total in terms of where it's coming from, wholesale, stores, and online.
Mickey Drexler 1:59 ↗
Well, it's hard to explain without saying what it was six or so years ago, but in any case, it was only a thought in our minds of what it could be and should be. And frankly, right now, we're starting to get some of the good traction that I always like to see, although it took a bit of time. We are current well it was tiny with no stores when we started Alex and I and Samsac is the third relaunch person and a founder in the relaunch. So there's the three of us and what it was and what it is it's a long way from that. It was just a feeling about vision etc. on what it could be and now we're getting close although you never get 100% because you're always climbing the mountain. Anyway, we have now two stores. We had a third store was not successful. But we tried hard and maybe not hard enough. So, we have a store in Soho. We have one on the Upper East Side. We sell wholesale to about 30 or so accounts. And the reason we do and there are positives to it but we did it because we did not have enough orders quantities to meet minimums from factories worldwide but mostly overseas of course Asia overseas etc. So we needed to have the minimums rounded up with wholesale. So that's been the initial vision. Wholesale is not in I guess whatever my toolbox if that's the right word, but and it's not anything that I'm terribly involved in other than pushing and doing whatever I do and getting bigger orders. But the positive is that it's good exposure for us with only two shops and what was a very small and flattish growth business to have people see who we are and help them go online and buy our goods. So in any case the business over the last year or so finally and I'm very happy about it got traction. It was a very difficult five or so years because I wasn't used to doing what I do in terms of the smallness of the team of the company and in many cases the need for improvement among the work we do. But in hindsight I don't think we could have accomplished what we are accomplishing without the fact that it was small and we all had multiple tasks. There were about 20ish maybe now we have 30-ish team members. The irony is we have three designers all from the old place who came from a team of probably 20 to 30 designers designing the same amount of SKUs. Much more edited upfront, but it shows you what talent and what the reality can be. I never would have planned that, but for the fact that it was a necessity, payroll, finding the right people, but it works well. And it works well because we're a little shop here and we're always we have it's kind of like it's like whatever I envisioned the startup to be in the old days it's what it is. There's if you walked out of this our only conference room the only private space you will see lots of people and you walk through 5 seconds and you're seeing everything and anything. All the boards are up always. You're listening in. You're eavesdropping. You're calling from my desk. I don't have a deskish table to the other team members. And that's very hard to do if and I never did that. Although Ann Taylor was quite small when I started, but nothing was this small and nothing I wasn't nearly as driven to be successful. I guess I always was. So that's not true. But so that's a great advantage. You pick up all these little things on the calls, on this on listening to customers, which is much easier to do here because we only have two shops. You walk in and every week as a necessity and a good practice is you speak could be every day to the store team members and they tell you things that either act upon or we don't act upon. But it's a small business growing bigger now but in fact I hope that characteristic never changes here.
Ken Pilot 7:33 ↗
Where are you seeing some of the momentum and you've told me over the past months you're actually seeing businesses doing quite well and I would say from those with whom I speak you're in the minority I hear more things around challenges the customers slowing down people are concerned with what they're buying but you're realizing success where are you seeing the success within the business?
Mickey Drexler 7:56 ↗
Well you know I'm going to give you not a specific answer yet because it's the whole business. I felt and in all my experiences in other jobs that I'm always looking for white space meaning a space that I and we feel has an opportunity to grow and so the beginnings of this were that the opportunity to grow and I see out there and it's my own opinion no one told me we didn't do research I saw what was and it's the same thing happened at Ann Taylor and Gap a million years ago. What was a white space that we could go after and fill or tried to and it's never that easy especially when you're reinventing or you're starting something but it always began and it started because you asked me about how you form a strategy. When I worked at A&S, my last department store job, I always wanted to have I made up a list was in my drawer in the right hand side because I wasn't having fun and I did have time to take notes, but I did my job, but whatever. And I had a list of things that if I was going to start a business, it would have the following list. And that was really the list that was the formation of Gap. Ann Taylor happened to come along. I took the job because I learned how to kind of run the business. You never learn everything. But the list was a Gap appropriate list. Ann Taylor was a fashion business novelty. But I also felt there was a white space there because you always got to believe in something. Even if you're wrong, you got to have a vision and a point of view that drives you. Got to Taylor and just went to school after 12 years in three department stores. I went to school and I the self-taught learning learning from the team around you learning from customers always and we built kind of a really nice business that for me was very not nice when 6 months after a job I loved was taken over by a very large bureaucratic department store no longer around called Allied Stores. I'm not a big fan and even though I've maybe created some big companies, but bureaucracies are the enemy. Lots of people in lots of layers of the enemy. But so I'll never forget the Sunday I got the call that Allied Stores won the bid to Ann Taylor. And I was immediately upset, depressed. There goes what I what do I do for the rest of my life again? I was all 35 years old then. But I stayed for almost five years for a couple of reasons. How you know practical, how to make a living, pay the rent, do this, do that. And I loved what I did and I wanted to learn. And frankly, there weren't there's not a lot of great jobs out there. Unless you're in a position of creating a great job. So I left after five years of dealing with bureaucracy. Someone does this, you have to do that. The one thing I always remember is they asked me Ann Taylor became a hot business. It was hot before it had Soho Shakuerie first one with a restaurant 57 and fifth Joan and Dave shoes and the shoe thing the restaurant thing that's probably where the traffic was for the first year. But then I learned, and I know this is long stuff, we'll do your editing, but I learned pretty quickly at Ann Taylor that if you don't own your own brand, you're subject to the whims and ways of your competitor, on sale, on sale here, that that and the other thing. Then of course, well, of course not. But at Bloomingdale's, I learned meet the price of your competition. It was a very religious lesson. And Brooks Brothers, which then was a different Brooks Brothers than it is today for sure, had their own label, Brooks Brothers. They never had to worry about competitive markdowns. Never had, you know, they had the wall, the moat built around their brand. And I took a page out of their book and said the only way I would like to for our company protect ourselves is to have our own brand. They call it private label. I don't call it that. I call it goods that we design ourselves, formulate, have a vision for that. You know other companies have designers doing that. But we have designers frankly who are also in the merchandising business. And so immediately well within a short time when I learned went to school at Brooks Brothers we hired well we had two vendors Irving and oh I'm forgetting the other name Irving Benson and whatever and they were big resources to us and we went to them and said we'd like you to design with us a collection for Ann Taylor and we called it Ann Taylor Studio and pretty much after the 5 years or so that became the biggest part of our business couldn't have done it alone. Needed experts needed people who know the marketplace production as you well know Ken is critical and so Ann Taylor turned it turned very quickly. It went from 25 million to 75 million in those days. you could add a couple of digits and we went from 20 stores to maybe 50. And you know, you go in, you do what you think is right. You try to pick and I had a very close friend who did the real estate with me. Allied had a big real estate department, but Dick, my close friend, was the real estate department. Always call on those who know more. And for example, in the old days, he taught me, you know, count Mercedes in the parking lots for high class business. We drove to Plano one day in Dallas looking at the store halfway through on the Texas freeway. He says, 'Turn the car around. We ain't opening up out here.' So, you know, it's common sense. And a lot of it is common sense in this world. So, I did that for almost five years. got a call from an old friend at Rose Wells who was consulting at the Gap and she said they're looking for someone to run it. I could have been you know many there were few of us on this list prior they went through two or three presidents and I never wanted to move out in New York but I started chatting with Don Fisher. I was also in my career chatting with Les Wexner quite regularly. they were the two big mockers in the business you know specialty business so worst case I was going to learn a lot which I did best case you never know turned out to be best case in a sense and so I decided after lots of thinking that well I was talking about starting a company with Don and I realized after a few months of chats I would never want them to start a company funding me because I didn't think they Gap was going to be around forever based on what I learned pretty quickly. Discount here to fall into the Gap. Everything was a discount and decide I'll never forget I was visiting Houston, Texas. I visit the stores a lot certainly at the beginning parked in Houston. I must have been there a month. I said, 'What the hell am I doing in Houston, Texas?' But that was a personal thing. It was very difficult to adjust to a new culture as you well know because you went through the same thing as I did. So I parked the car at Houston Galleria. I see there's windshield flyers flyers on every windshield. So I get out of the car, rented car, no fancy whatever. And I get out and I take a flyer off the window and it said this today only 30% off of all things at on retail at Gap was a sale with windshield wipers probably a little off brand and so I walked in the store Hector was the I think he was then the store manager became a regional I said Hector what's going on and I sometimes get a little testy on that, but he wasn't his fault. He took Maybe it was I don't know. I said, 'You can't do this.'
Ken Pilot 17:27 ↗
Wait, were you were you were you researching the company at this time or were you working?
Mickey Drexler 17:32 ↗
I was the new president of Gap. And I you know, and the first thing you do is you visit stores. Not that I wanted to go to Houston. I grew up in New York City, the Bronx, and all everything was foreign. San Francisco was foreign to me. But you do what you have to do and you if you thought about it, you really don't want to do a lot of the things you have to do, but that's life. And I was very driven, still am. And not no pun intended because when I drive to shopping malls, I have to drive there. And so so I left that and of course I'm on the phone all the time, but it was a weekend. I don't know. No one was answering. But that was that was just a notch in the points you had to deal with. The culture was a discount culture. The goods were was a Levi's only company and we were then 33 35% Levi's. And you know, they're my friends, but I didn't like doing business with people who were trying to sell us more goods. Eventually, they didn't like us either. I guess it was me. And they fired us at a long lunch that they said, 'We're not going to sell you anymore.' And the only thing I'm thinking is you should have said that at the appetizer level because you know it's like an hour hour and a half we're discussing it. So, we went fully Gap brand and we had 20 different brands and they did surveys on everything and the biggest most popular brand. I'll never forget a lot of this stuff. It women's pants were all called Foxtails. That was the name. And then they say, well, it was the most popular name in our focus group. Don't get me started on focus groups. Anyway, A to Z at Gap. A to Z, no matter what. I brought in the head of marketing from Ann Taylor in New York. She moved to California. I brought in the chief creative. Same thing. Moved to San Francisco. Well, no, they stayed in New York because the creative was in New York as you know because San Francisco, you know, New York and maybe it's still the same business garments. There's a thing about New York water that creates the creative environment, whether it's in creative marketing and dot dot dot and bagels. Bagels and pizza also, you can't do it without New York water. That's right. And of course Silicon Valley became the New York of you know technical and so on and so forth. So I know these are long answers but the question was Gap grew like crazy vision list of the goods that we wanted that was in my desk drawer and that big headline was good taste and good style shouldn't be expensive or more expensive and if you look today designer clothes are whatever but you know we we are we do designer clothes happens to be our designers and our merchants. Merchants are critical and and the prices are fair and stylish and that's what we do.
Ken Pilot 20:57 ↗
You know, Mickey, you mentioned big company versus small company. And from what I recall, even though Gap was a pretty big company, again, growing to 14 billion, which is not small, I do recall the way you operated even within a big company was as if it were small. And by that I mean you you tended to manage by wandering. You could you could pop up in an office at any time. You threw yourself into many meetings. You were always curious about what people thought. Always known to talk to the new people who joined the company and pick their brain on what they thought was most compelling that Gap was doing. Give it thought and see how it applied or did not. But it was your curiosity, your managing your management style and how you got involved at many different levels and layers. And I'm curious to know today with Alex Mill obviously being small as you discussed earlier, how you are still managing to organize your time, show up at key meetings, and at the same time overhearing what's happening at one table or grabbing someone from another room or having a Mickey meeting break out when no one was planning it. So I I I went kind of behind the scenes to get an idea of just some of the meetings that typically take place and would love to understand how you see the importance of the meetings and what you really impart on the teams. So first and I don't know if you're still doing this but is there an inspiration trip or a vision trip that you go on because we used to go on those to just see what was out there in the world, what was new and fresh.
Mickey Drexler 22:43 ↗
Well, that's a good question. You have to do what you can afford to do in a sense. You know, in the big companies, they were banks. You know, Ann Taylor was a bank. Gap had a big bank. And right now, the bank is it's me, it's Alex, and S is the third anointed founder with a important stake along with everyone else who has stakes. But you know, you make do what you have to make do with. And for me, I don't take those trips. S and his two partners, Alice and Jordan do. And when I go, which is not often, you always get ideas. You can shop New York and get the same thing out of a trip in New York. I can be in an elevator with someone. Everything I see registers. A woman this weekend said she loved the reversible coat she was wearing and she said, 'Do we have any?' So, I checked out this morning. I was just curious. No, we have a reversible jacket on order for spring. Oh, no. She wanted a bucket hat. So, it was a bucket hat, which is always never goes out of style, but we do we did talk about it, not because of her, but we have one on order for next spring. But you're a constant student. You can't you know, I could see things no matter where they are that I apply every weekend. I look at the Financial Times because it's a good Saturday newspaper and like I cut out pictures. Today at 1:00 we have our weekend update, not like in Saturday Night Live, but I cut out pictures monthly from all the magazines. You never know. And you're roaming and and that's why I'm addicted to detective stories because if you find a clue, you keep chasing it. And there's a lot of clues out there all day long and you find them and then you try to chase them. It's not always easy, especially in a small company like this.
Ken Pilot 25:03 ↗
So Mickey, when when the team the team comes back and they've done this inspiration trip, you you sit with a group and see you look at the goods. I know you're a goods guy. You want to be you're in the room with the goods.
Mickey Drexler 25:15 ↗
I'll tell you what I'm doing. I'll be right back. So here we are, Ken. Yep. now. And here's Jordan and Sam is there. But Jordan, hello. Hey guys. I think you know Ken Pilot, right? Yeah. So, if if you look at this, these are boards. Yep. Now, Tom, you know, of course. Now, these are pant colors for next to this summer's men's spring wash pants. Now they do this and I don't use the word meeting because I'm an interferer. What is it called when you walk around anyway? So these are all the pant colors. And so here I don't have to call a meeting because you know I just toured corporate headquarters here in about 8 seconds. But you look at this and then it gets inspiring for me and they're inspired already. And then you try to figure out how many colors do I want? And I always love colors. Love. And to me it's a painting. Now this is kind of special. These are all vintage scarves. That might look familiar. Are these coming from your neck, Mickey? I've seen a few of you. Well, no, Ken. Yeah. Well, well, these scarves are Michael Drake's straight from Mickey's neck. Yeah. my but they're 30 I mean Michael Drake was a friend when I was at Ann Taylor and he was in my opinion by the way I meet a lot of people and I'll make a lot of mistakes but Michael had scarves and I probably purchased wholesale I will say all of his painted well these are photographs of all the scarves that he had there's a point of view here we're not going to do them all sometimes we change other times we don't But you know, that's why people say vintage is so good today. But you can't find a scarf like this even at Michael Drake's today that in our opinion has this point of view like I don't like this one so much. But you know there my favorite one in the world by the way is this. And people say well why is it your favorite? I said why don't you like chopped liver or something? You know how do you explain what your favorite is? So, so Ken's asking about you go to Europe. Well, he and Alice just came back. I don't know what the hell they were doing there. Sabbatical for how many days in London in Paris, but what did you come back with in a way? Because he's asking, you know, the inspiration that has come from.
Jordan 28:04 ↗
Yeah. So, I mean, we we did a lot of vintage shopping. We went to all the different stores, the new stores, and just soaked up. We took tons of photographs. Hey, Ken. We took tons of photographs and got inspired for the next two seasons basically.
Mickey Drexler 28:22 ↗
Yeah. And and it's all, you know, our newest blazer. Well, we we get inspired. You know, the designers get inspired. They go to vintage, which business is great today for a lot of reasons. But you know, you find out what's interesting and style for us never goes out of style. So, I'm wearing an 8-year-old blazer from Alex Mill before my time, and it's it's a blazer, but you don't need anything that's $10,000. This retails for $295. And it's cotton. It's simple. It's easy. But that's what we do. It's logical. It's how do you think people should look and what doesn't in fact go out of style.
Ken Pilot 29:14 ↗
So now as so Mickey as you guys are planning this is for again summer 2027. We're still looking almost a year out or spring 2027. Are you using the the data, the sales, the business of today to think about next year, the hindsight meeting that we used to do to see what's working and what's missing. But we see you remember you call it meetings here. They're not meetings per se. You can go around and gather like these shirts. Well, this one's 10 years old. And I have shirts blue and white striped never go out of style. So you know you're going to always have blue and white stripes in stock. You're looking what's new this year? I mean what do you think without giving away secrets? What did you see that's exciting and reinforces things?
Jordan 30:10 ↗
I mean we saw so many people in like funnel neck bombers for example. Like everyone on the street was wearing funnel neck bombers kind of like Yeah.
Mickey Drexler 30:19 ↗
Now you see it and and you have to have the kind of the genes to make that register in a way but you see repetitiveness in a sense drives things. You know three years ago we recognize every cool woman and some guys wearing long overcoats. You see that you can't help you observe in the elevator here at our office, you know, it's it's three or four fashion companies and elevator shopping here is actually it's actually very helpful. Then you you know, you say, 'Hey, I like that.' And then you sometimes invite them in there. There's it's fun. That's why I love what I do in the big company. Yeah. with with this now you have you have concept you have vision off off the design team goes and begins working on product and samples when will be the next when will you sit down again not in a meeting but when will you discuss what the buy looks like oh well June by well when June June the end of June end of June but it it's you kind of it's it evolves into the high or the investments as they call it here. But the end of June we we go through everything very finely and we'll do it a couple of times. Key issue today. Less is more for customers. Everyone has too much assortment. Now we would never have an assortment this big. Hold up. If you see no right. But like Mickey, you have you have an assortment there. Let's call it 12 prints. You might get down to three. Oh, four. One, two, three, six, 30. 32 prints. Um here. Oh, actually, I'm sorry. One, two, three. No, they're divided by two. It's It's just each one of these represents one. They're just long. So, 1 2 3 4 5 6 7 8 9 10 11. So, there's 11. We'll probably do three maybe. Got it. Yeah, I would say I haven't seen it, but I'd say three and maybe five. Well, we're not going to develop all these. We just wanted to photocopy Mickey's to kind of have an archive. But but but I think there's no right or wrong answer on three, four, or five. What I like is you have the best two or three for all the money and you invest more in them and then you have two that you might think are special, unique, and aren't going to be best sellers, but for example, this red will sell. Well, here's the red, too. You know, it's a matter of investing like you would look at stock market or shorts or longs or whatever and and figure it out. But see, I would have said here you need five. I don't know to to make some kind of statement. Sure. Because you know, most people make two bigger statements. You go to the supermarkets today. Oh my god. This no one's assorting in a way. They have old deals too. And when you think about this, this could be it could be a scarf. It could be a lining. It it could be a print shirt. I mean, there's there's not no limitation to what you can do with these patterns. See, now that's a great idea because these could all be linings and whatever else. And clearly these are all silk and quite expensive on a basis, but you can adapt and have an artist paint some of these. They'd be great linings. Yeah. And we were in a tie business. We're not might say that. But it it's you know, and the mission that we have, and it's something I've never done well enough. Less less less to choose from. You go into a supermarket today. You go into a shop, the assortments are painful to try to figure out 30 cereals. Give me 10 of the best ones maybe. And but don't have 30, but they're buying every vendor, I think. And a lot of companies do that.
Ken Pilot 34:45 ↗
Well, you've always been known to be to be very focused the and specifically on curation, making sure there's a point of view. Tell me more about your weekend update meeting. What what happens with that meeting? What are you looking for besides getting the buzz? I mean, what feedback are you getting in the in your weekend update?
Mickey Drexler 35:03 ↗
Just to answer, I've tried to be I've never been focused enough on a simple product assortment basis. Weekday
Updates. It's kind of that's what we call it. But I have on Saturdays and Sundays, well, Saturdays, it's not just that. The weekend update is everything that happened the prior week that I think or feel would be something that the team should consider or design into, or it was a service example we had, or it could be anything. And I just take pictures and I bring them in Monday morning and we photograph the meetings at 1 and I just, it's very informalish.
Oh, CVS are a lot of weeks but to get a message across. Wall Street Journal. Now you can always learn something. I like the concept of the power suit. I would never call it that. You remember at what we did with one suit at J Crew? What did we...
Ken Pilot 36:23 ↗
Lello.
Mickey Drexler 36:24 ↗
The Lello suit.
Ken Pilot 36:27 ↗
These are all weekend updates.
Mickey Drexler 36:32 ↗
So we go through like I said.
Ken Pilot 36:35 ↗
So, for those I'm just going to point out for those that may just be listening and not watching, Mickey's holding up the off-duty section of the Wall Street Journal, which is a great read on every weekend because it just ain't all about business. It's about the creative part of the business as well.
Mickey Drexler 36:51 ↗
Yeah. And what came from this for me was I want one suit. Kind of reminds me of Lello in a way. And then we all add and add until there's too many flavors of the ice cream or whatever it is. But that's just one thing. Color. Yeah. This is now, this, the only reason I did this is she's wearing a cashmere top and a cashmere crew neck with a white shirt. We have a great cashmere business. And this, we have scarves and I thought we should be painting. We have state and city scarves and we have, and I love children's art if that's children's art. And I thought the team, now this is not dictatorial. Color orange, we loved it for the last six months. It's the most popular color on the streets of New York because all the signs are caution. You know, they're all orange signs. You see more of those than anything. And then color, things written down. Nice clothes for nice people is a touch. That's what we do. And I think it's an important thing. Marketing critical. You have to match up marketing with goods. And we're learning that more and more. Which means these are all ever. Oh, hello. I'm not going to tell you what this was about, but there's an item here that you can't see that is amazing. I'll tell you later. It's one thing she's wearing. This is what, there's a magazine that does this. It's all about accessories. It's all about a color story. It's all about that. Very important.
Ken Pilot 39:04 ↗
Which magazine is that, Mickey?
Mickey Drexler 39:06 ↗
I don't want to say.
Ken Pilot 39:07 ↗
Okay.
Mickey Drexler 39:08 ↗
I'll tell you after.
Ken Pilot 39:09 ↗
All right.
Mickey Drexler 39:10 ↗
Okay. Trade secret. It's well, it isn't because, but that, it's part of their branding and I think it's terrific.
Ken Pilot 39:19 ↗
So Mickey, you mentioned marketing. I want to talk to you about that because you have a weekly marketing meeting and I'm going to assume...
Mickey Drexler 39:27 ↗
It's weekly but everything is every minute of every day.
Ken Pilot 39:32 ↗
Okay. Go ahead. But you have one, you do have some time blocked on the calendar to actually pull people together to talk about marketing.
Mickey Drexler 39:40 ↗
And we do that a lot at the weekend update.
Ken Pilot 39:44 ↗
I assume you're discussing not only what's happening at present, what's working, but also thinking about how to market what's coming in and the future.
Mickey Drexler 39:54 ↗
Always. But well, always future. If you're not planning to see around the corner what's coming, there's always something coming and there's always something inspirational out there.
Ken Pilot 40:10 ↗
It's interesting, Mickey. You know, you take a look at what you did with the tote bag, which was a very big push, strong focus. You had to be blind to not realize there was a tote moment happening. It's still happening at Alex Mill, but you put some strong marketing and some influencers behind it.
Mickey Drexler 40:28 ↗
Okay. I'm going to tell you the bad news on that. All right. Three years ago, we had a notion about, you know, totes are all over the place, but we had a notion about painting something on a tote. I'll never forget, this was on my pissed-off list for a very long time. They sold out, I won't even say what it was, but it wasn't initials. They sold out in two days, 20 of them at $225. All because of what we painted on them. And from then on the personalization thing started to be in our minds. Personalized, personal, took us, now part of it is, and I have no patience, but part of it is you don't have the kind of resources you have in the big companies. A lot of money is wasted but that's the way things are. But you might waste something and then you got a huge payoff on something else. But it took way too long to do it. Finally, I don't know how it happened. Maybe we had some people who came in to help. We were very short of the kind of help you, we just, you know, it wasn't easy. But now we're doing what I said last week. It's not just a weekend update. I said, I don't want to buy anything for us in our shops that we can't match with a marketing plan. We have great things. So, someone calls me and part of this is just a friend or a picture. We have, oh, you with the jacket, right?
Ken Pilot 42:21 ↗
Yeah. Me with the jacket. The David jacket.
Mickey Drexler 42:24 ↗
Right? You sent a picture or you said we have a, that's funny, it's you. So, we have a jacket called the David and Ken said it looked like whatever that brand was. That would be...
Ken Pilot 42:38 ↗
Stone Island. It looked like a Stone Island item.
Mickey Drexler 42:41 ↗
Yeah, Stone Island. I mean, it's missing a decimal. Anyway, it's a men's jacket, but then, so, you sent me the picture. Another guy who I met sent me, oh, that was another jacket. You sent me the day that I look at it. I try it on. I buy the David. And then a woman sends me, a very cool woman this week. I don't know if I told you this. We met her willy-nilly. She became our friend. She lives in Charlotte. She's kind of an influencer type. And she takes a picture of her in the David jacket. Now, one, two, three. All of a sudden, you know, and then you look at the selling. We didn't have much marketing for it. And I say, you got to match it. Now, here's our in-house model, meaning she's one of the team members. They model most of the stuff we do. And this is the David on a woman. And the woman from Charlotte said, 'Why don't you put this in men's and women's?' We're trying to do that. We haven't figured out how to. Hey, working a little like here.
Ken Pilot 43:58 ↗
Yeah.
Mickey Drexler 43:59 ↗
This, it's a men's jacket technically. We love it. It comes in blue, green, and red. And then it has like the elastic poles so you could like...
Ken Pilot 44:09 ↗
Scrunch it up. It's great. It's very cool.
Mickey Drexler 44:11 ↗
It's got a great, and for those that can't see it, it's got a great crinkle nylon that really, it's very supple the way it works. And there's a removable hood which buttons out. And you know, and if you don't show this it gets lost. And you know, that's why McDonald's was one of the greatest inventions. Hello hamburger. And you know, we have jackets. Yeah. Thank you very much. So, you know, but you know, you and then the other woman and then the third person and then I wear it and say, but that's, you know, that's how things happen. You know.
Ken Pilot 44:58 ↗
Mickey, how do you make sure, I mean, I get it, curation, less is more. How do you work with the teams to really understand what fits in the store and the story you're going to tell in the store and how product is going to speak to the customer?
Mickey Drexler 45:15 ↗
Well, it's a good question. And how do you tell them, you know, I said before I always these throwaway lines, why do I love this? Why do I love orange? Oh, here's an orange. But orange, I just gave you the answer to that question. Anyway, why did I love it? You look at it and part of the job of anyone is to know what's brand right. And I could mention companies that do and there less that don't in a way, but a brand company has a point of view. I'll mention my old friend Mr. Y and I. Look what that guy has done. I'm proud to say he copied everything we did at GAP in the mid-80s which he did once thank us for.
Ken Pilot 46:14 ↗
And Mr. Yanai is the founder of Uniqlo.
Mickey Drexler 46:17 ↗
Uniqlo may not know, may not know. He's not my friend. He doesn't talk to me. He's mad at me but whatever you know. So but you, if you know, you know. Look, this...
Ken Pilot 46:32 ↗
Mickey, I remember you saying to me, I'll never forget this, one of your quotes, although it hasn't turned up yet in LinkedIn but it'll get there. You can always tell a, something like, a great store looks like it was bought by one person.
Mickey Drexler 46:51 ↗
Because that was your quote. It's a strong point of view. It doesn't look disparate. It came out of one creative mind and it works together like an orchestra. And you know, when you walk through, when I walk through Alex Mill, it's not a big store, but it does look like it was assorted through one mind's eye, which is back to focus and point of view.
Ken Pilot 47:15 ↗
100%.
Mickey Drexler 47:16 ↗
You go to a lot of stores and you don't see that. You know, you have weak areas here, strong areas there, and they just fall short. And it's, I think it's an art that's lost. I think that there's so much going on today, and there's so much disruption in the process that you lose the perspective that's required to create a cohesive story or a great painting.
Ken Pilot 47:44 ↗
100%. And I remember things a million years ago that stuck in my mind. And I know you're going to edit a lot out, but that's good. But I'm telling you a lot of stories. But on the corner of Madison Avenue on 57th Street, when I worked at Anne Taylor, our office was up the block. Every night or every, yeah, every day I took the Uptown Madison Avenue bus home and there was a store on the corner there, French designer store called, oh man, I forget the name, Olivier, something like that. And he had 15 colors of cashmere in the window. I'll never forget the picture in my mind of that. And it's the question of how do you know? If you know, you know. You know, that's that saying, if you know, you know. And if you don't know, you don't know. And you try to figure out and I learn from everyone because and I've learned a whole new language because of the generational difference in my office. You know, I use kismet all the time. I had no idea the Yiddish term is bashert but you know I knew that term but kismet and you know things are meant to happen but it's exercising your brain constantly. And I have so many examples of what you did and what this one does and then I have so many mistakes, got a lot of mistakes out there also.
Let me ask you about that Mickey. If you had a, this, I'm going to put you on the spot here. If there was one thing, one mistake that you made over time, one thing that you did that you could take back and erase, what's top of mind for you?
Mickey Drexler 49:41 ↗
Well, you know, I have about four or five. I'm not going to mention the one that's financial.
Ken Pilot 49:49 ↗
Okay.
Mickey Drexler 49:50 ↗
What, this is not a, I mean, I made a mistake opening Hemisphere. I made a million merchandising mistakes. This is weird, but the one thing that I never did and I should have when I was fired at GAP. People might say, 'Why are you bringing it up?' Well, it was 20 plus years ago. When I was fired with no notice, I never said a word to the board. Well, I couldn't. And I don't know if I'm going to want this in there. You'll be the judge. But it was stunning that I had no notice. Stunning. And you know, I wouldn't include this. Steve Jobs was the one who called me. And I was thinking I should have gone into the board and say, 'What the fuck?' You know, I mean, give me a reason. Tell me why. I wasn't stealing. I wasn't doing this. I wasn't. And then the day after the press conference, I was told by Don, 'I made a mistake in firing you.' And I'm thinking, you're playing with my life. And this is in hindsight. You played with my life, my family. I lived in San Francisco. And I had a bad year. I had a bad year. Now, I had a lot of very good years, but that's the politics in my mind of large corporations. Not, and I was the CEO, but you know, everyone doesn't love you.
Ken Pilot 51:30 ↗
No, but that's what happened to you. It wasn't necessarily a decision that you made.
Mickey Drexler 51:34 ↗
No, I didn't make the, okay, that's right. I didn't make that decision. You're absolutely right.
Ken Pilot 51:42 ↗
You said Hemisphere was a mistake, but Old Navy was not a mistake. It more than made up for that mistake.
Mickey Drexler 51:48 ↗
Well, I'll tell you, I can't mention names. Okay. But the biggest mistakes I made hiring the wrong senior executives and you know a lot of them and I'll, you know, I can tell you who was but anyway that was the biggest mistake I made. Because a bad, you know, one bad ingredient can throw off the whole, you know, dish or the recipe and all that. So that was pretty much the ones that stay with me.
Ken Pilot 52:28 ↗
Is that related to just how much we did around opening stores and how aggressively we grew the business?
Mickey Drexler 52:39 ↗
Ridiculous.

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APA

Drexler, M. (2026, May 6). Retail Legend Mickey Drexler: From Building Gap & Old Navy to Running Alex Mill Like a Startup [Interview transcript]. The Retail Pilot - Leaders & Legends Podcast. CEOInterviews.AI. https://ceointerviews.ai/interview/889616/

MLA

Mickey Drexler. "Retail Legend Mickey Drexler: From Building Gap & Old Navy to Running Alex Mill Like a Startup." The Retail Pilot - Leaders & Legends Podcast, 6 May. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/889616/.

BibTeX
@misc{drexler2026_889616,
  author       = {Mickey Drexler},
  title        = {Retail Legend Mickey Drexler: From Building Gap \& Old Navy to Running Alex Mill Like a Startup},
  howpublished = {Interview transcript, The Retail Pilot - Leaders \& Legends Podcast. CEOInterviews.AI},
  year         = {2026},
  month        = {may},
  url          = {https://ceointerviews.ai/interview/889616/},
  note         = {Speaker-attributed transcript with timestamps}
}