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

Summary

Podcast Summary: “American Crew” – Interview with Mickey Drexler, ex-CEO of The Gap & J.Crew

The Best One Yet | Nick & Jack Studios – July 2, 2026
Guest: Mickey Drexler (fmr. CEO, The Gap & J.Crew, Apple board member)
Hosts: Jack Crivici-Kramer & Nick Martell
Theme: Dissecting the story, style, and mindset behind the man who shaped what Americans wear, featuring untold stories from Gap, Old Navy, J.Crew, Apple—and Drexler’s philosophy on creativity, data, and staying relevant in the age of AI.

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Episode Overview

On America's 250th birthday, hosts Jack and Nick welcome Mickey Drexler, the “pharaoh of fashion” whose influence on the American wardrobe is legendary—from overseeing The Gap’s meteoric rise to inventing Old Navy, reviving J.Crew, and helping Steve Jobs bring the Apple Store to life. The conversation explores Drexler’s journey from the Bronx to boardrooms, his eye for style (and business), the importance of emotion in fashion, building enduring brands, and his take on fads, reinvention, and why ignoring data is sometimes “patriotic.”

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1. The Drexler Legend: Setting the Stage

• Introductions and accolades:
  • Mickey Drexler credited as shaping “All American Style,” launching Old Navy, revitalizing J.Crew, creating Madewell Jeans, and advising Apple.
  • Hosts dub Drexler “the chairman of chinos, prince of the popped collar,” stating:

    “No one in business has influenced our national wardrobe quite like this man.” (00:30, Nick)

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2. Mickey’s Story: From Bronx Beginnings to Fashion Icon

Early Life and Influences

• Bronx upbringing / garment industry roots (06:10–11:08)
  • “I always cared about how things looked...I lived in my fantasies a lot. Because I didn't like living in my home a lot.” (09:16, Mickey)
  • Entry into fashion: forced by his father to work in the shipping room; entrepreneurial side hustles selling razor blades.

Early Career Moments

• Moments of fate:
  • Securing a job after an offer at Abraham and Strauss for less than a classmate, which pushed him towards Bloomingdale’s—where “the energy” of the place drove his decision.

The Power of a Muse

• Jackie Kennedy as inspiration:
  • “Jackie Kennedy, you know...to me, she was who I felt I wanted us to be dress, you know.” (14:44, Mickey)
  • On finding muses: “A muse is someone who inspires you. It's emotional.” (15:20, Mickey)

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3. Gap Years: Transforming an Industry

Taking Over The Gap

• From Ann Taylor CEO to Gap turnaround (16:02–23:07)
  • Describes initial culture shock, challenges moving from NYC to San Bruno, CA, and public company pressures.
  • First steps: travel to stores, recognize rampant discounting, need to simplify and focus.
    • “Everything was discounted...So what I did, I always do this: get together with the team, look at all the merchandise.” (20:52, Mickey)
    • Instituted “Keep It Simple, Stupid” (KISS) plaques on employees’ desks.

Gut Decisions, Purge & Reinvention

• Cut unproductive inventory, convinced Gap to adopt washed Levi’s, launched Gap Kids (which he admits was “a big mistake” financially):
  • “To make a kids shirt in kids sizes...didn't work. And kids is very much a discounty kind of business.” (25:33)

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4. The Birth of Old Navy: Disrupting the Market

Spotting Opportunity and Acting Fast

• Old Navy’s origin story (26:11–34:10)
  • Triggered by a New York Times article about a Target competitor (“Everyday Hero”) aiming to undercut Gap.
  • Key realization: Gap jeans were priced far above 80% of the under-30 market.
  • Sent team members with $200 to shop at discount competitors; learned customers wanted value, clean stores, and respect.
  • “At the end of that meeting...I said to Jeff, I said, we're doing this. And that was the beginning of Old Navy.” (30:57, Mickey)

On Naming and Brand Identity

• Name “Old Navy” spotted on a Paris dive bar sign:
  • “I saw ahead...a movie marquee...I said to Maggie, ‘that’s the name. Old Navy.’” (31:23, Mickey)
  • Fought board resistance (“Gap Warehouse” was almost approved) to keep Old Navy distinct.
  • “I said, there will be no Gap in five years if you call it Gap Warehouse.” (33:27, Mickey)

Creating Treasure Hunts

• Notable ideas: Selling Schwinn bikes at Old Navy’s Manhattan store—unexpected “treasures” drive excitement and loyalty.
• “Always better than the expected in anything.” (34:10, Mickey)

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5. The Madewell Move & The Art of Branding

Acquiring and Building Madewell

• Bought the dormant “Madewell” name for $125,000 just because he loved it (36:03–37:24).
• On naming brands/products:
  • “If you think about the name...I want every name to be personal in a sense, because they’re your friend, if you remember it.” (37:37, Mickey)
• Everything is about evoking feeling and connection.

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6. Designing the Apple Store: Collaboration with Steve Jobs

Friendship and Boardroom Politics

• Steve Jobs recruits Mickey to Apple’s board; Mickey, in turn, brings Jobs onto Gap’s board (41:18–43:44).
  • “If you join my board...I'll join the Gap board. I said, deal.” (42:30, Mickey)
• Jobs and Drexler both known as “micromanagers.”

Creating Retail’s Gold Standard

• Jobs presents a first Apple Store concept, Drexler deems it “ugly.” Advocates for simplicity:
  • “Let it be timeless and let the product speak.” (43:55, Mickey)
  • “Timeless for me, in clothes, in design, never goes out of style.” (44:23, Mickey)
• Store design hasn't changed in 20 years—testament to universal, emotional, and simple design.

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7. On Fads, Nostalgia & Reinvention

The “Three Fs” Vulnerability

• Hosts: Fitness, Food, Fashion most prone to fads (50:10–52:49).
• Drexler:
  • “I blew it on this, I blew it...But I don’t think that way. If I did, I’d get into trouble.” (51:22)
  • Cites Levi’s 501 as a timeless, unkillable product.

Scarcity, Logos, and Constant Evolution

• Warns of logo fatigue and overexposure:
  • “A logo unscarces. I mean, you know...But now what's unique is scarcity.” (52:43, Mickey)
• Must balance reinvention and focus:
  • “The hard thing about this business is you gotta keep doing it.” (53:08, Mickey)

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8. Data, Intuition, and Decision-Making in Fashion

• Drexler mixes instinct with rigor:
  • “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.” (53:34–54:49)
  • 90% of decisions are data-driven, but “then there’s a gut...Bring this back.” (54:52)
• “It’s not a democracy when it comes to colors or things you sell. What's the most famous color for men? Navy.” (54:42, Mickey)

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9. Can AI Be Cool?

• Why AI can’t replace human style:
  • “AI will not write songs that move us. It doesn’t have emotion. It can have taste.” (55:54, Mickey)
  • “Beating AI is about being cool.” (01:05, Nick [earlier teaser])

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10. Quick Hits & Takeaways

Rapid Fire with Mickey

• Timeless must-haves: “Five pocket pair of jeans that fits him in the right wash. White shirts. Classic blue and white striped shirts.” (56:33, Mickey)
• Best fashion brand Mickey didn’t work for: T.J. Maxx—“They have real prices.” (57:45)
• Best business book: Phil Knight’s Shoe Dog—“I’m not a big reader, but I like that.” (58:12)
• Most admired business leader: “I loved Steve [Jobs]. The best. He cared about the products.” (58:37)
• Stock ticker for ‘Mickey Drexler Inc.’: “SMPL (Simple).” (59:25)
• Main takeaway:
  • “I never had a grand plan to be who I am today...Every day I have to beat myself and what I did yesterday. 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.” (59:41–60:11, Mickey)

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Notable Quotes & Moments

• “Keep it simple, stupid.” (multiple points, Drexler)
• On fashion: “Style never goes out of fashion. Fashion can go out of style because fashion’s of the moment.” (44:56, Mickey)
• On reinventing: “What's old is new today. Give them old and it’s new.” (49:37, Mickey)
• “Emotion is the most important...my heart, the bell goes off.” (38:12, Mickey)
• On Disneyfication: “If you call it Gap Warehouse, there will be no Gap in five years.” (33:27, Mickey)
• On being a micromanager: “I am proud to be a micromanager.” (47:33, Mickey)

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Timestamps for Key Segments

• Mickey’s Bronx roots, early career: 06:10–13:22
• Gap: arrival, turnaround, first moves: 16:02–23:07
• Founding Old Navy: 26:11–34:10
• Madewell acquisition: 36:03–38:01
• Apple Store creation: 41:18–44:29
• Fads vs. timelessness: 50:10–52:49
• Data vs. intuition: 53:13–55:41
• AI & style: 55:41–56:05
• Rapid fire/takeaways: 56:21–60:13

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In Drexler’s words:

“Every day I want to beat myself. Not beat, but every day I need to do better than I did yesterday. Every day.” (60:13)

Takeaway: Mickey Drexler’s success was never a matter of plan or perfection, but an ongoing battle with himself to be better—to combine emotion, relentless curiosity, and a sharp eye for simplicity and reinvention. He credits every breakthrough not to trends or focus groups, but to finding “the feeling,” keeping it simple, and honoring “the main thing.” The lesson: in business, as in style, what lasts is what moves us.

Transcript

[Jack]

Yetis, untuck your tees and cut off

[Nick]

your quarter zips, because today's guest is the former CEO of the Gap, J. Crew and the Apple Store.

[Jack]

Basically, we're interviewing Mickey Drexler, the inventor of All American Style Old Navy. He launched it.

[Nick]

Madewell Jeans.

[Jack]

He created it.

[Nick]

Outdoor voices.

[Jack]

Yeah, he chairmaned it.

[Nick]

If George Washington needed corduroys, he'd probably

[Jack]

call Mickey D. The Mickey D. Because Mickey's style is so fundamentally American, he makes Ralph Lauren look Canadian besties.

[Nick]

No one in business has influenced our national wardrobe quite like this man.

[Jack]

So when Steve Jobs launched the Apple Store, he asked Mickey for design advice.

[Nick]

And no big deal. Mickey was on Apple's board for 16 years.

[Jack]

Sixteen.

[Nick]

So he was basically Steve Jobs boss.

[Jack]

And in the age of AI, his tastemaker status has never been higher.

[Nick]

Because this is the mind who made khakis cooler than jeans by tweaking a stitch.

[Jack]

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.

[Nick]

And he'll tell us why. Ignoring the data is the patriotic thing to do.

[Jack]

Oh, and how to beat AI you gotta be cool.

[Nick]

He's the pharaoh of fashion, the chairman of chinos, the prince of the popped collar, Jack.

[Jack]

How about Miranda Priestley of American Prep? I'll take that. Does that work? That works.

[Nick]

Besties, please welcome Mickey Drexler to the best one yet.

[Jack]

This interview is the best looking one yet. Mickey, great to have you with us.

[Mickey Drexler]

I mean, that is exciting, high energy, and I'm. I'm in it. Thank you.

[Jack]

We gotta print that on some leather. Turn that into a purse.

[Nick]

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.

[Jack]

You starred on Breaking Bad. How do you pull that off?

[Mickey Drexler]

That was my proudest moment. I'll tell you the story. And you've added a lot of this stuff anyway. Yeah, so I'm having lunch with a friend years ago, and he said, do you ever hear of Breaking Bad? He 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. For Sony, who owned 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. Unbreaking bad. Sold. I said, no. A year later, you're like, I don't

[Nick]

want to go to New Mexico. It's hot.

[Mickey Drexler]

Because I get nervous about things like that. And he said again, I said, why not? It could be fun. So I go to New Mexico, I go to the trailer, and I was in the trailer. Nine takes. I was customer in the car wash.

[Jack]

Customer number two.

[Mickey Drexler]

Yeah. And the irony is.

[Nick]

Wait, were you a customer to get your car washed?

[Mickey Drexler]

I was getting my car washed. 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 a cash loaded in the safe at the car wash. So the irony is, she was honest with.

[Nick]

Yeah.

[Mickey Drexler]

And so that's it.

[Jack]

And not bad. Not too shabby for. For a fashion guy.

[Mickey Drexler]

Well, I'm not a fashion guy. I'm who I am, you know?

[Jack]

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[Nick]

Oh, yeah, yeah. Then we have to track down each employee and make sure they know their health insurance options.

[Jack]

Oh, right.

[Nick]

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[Jack]

Nope. No one did. Yetis. We are just podcast hosts. We also run a media company here. And full time employees mean full time

[Nick]

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[Jack]

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[Nick]

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[Nick]

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[Jack]

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[Nick]

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[Jack]

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[Nick]

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[Jack]

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[Nick]

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[Nick]

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[Jack]

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[Jack]

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[Nick]

So you're a New Yorker is what you are. We're interviewing right now in New York City, home of Jay Peterman, fictional fashion guy from Seinfeld.

[Mickey Drexler]

Jay Peterman. I thought he was from Chicago, but he was fantastic.

[Nick]

Well, he's also Elaine's boss in Seinfeld, and he's famous for the urban sombrero.

[Jack]

Remember that? Yes.

[Mickey Drexler]

Oh, he was amazing.

[Jack]

And Ralph Lauren famous for the polo shirt.

[Nick]

So what article of clothing is Mickey Drexler famous?

[Jack]

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.

[Mickey Drexler]

Linen. I'll tell you what I'm most proudest and hope become. I become famous for. We Alex Mill.

[Nick]

Yeah.

[Mickey Drexler]

Is the lanyard holding the iPhone? And the leather is Italian leather.

[Nick]

The phone lanyard.

[Jack]

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.

[Nick]

It's an alternative to a fanny pack.

[Mickey Drexler]

It's part of my uniform in a way.

[Jack]

It's a mani pack.

[Mickey Drexler]

And I never leave home without this. It's on and around all day, every day because or else I misplace my iPhone.

[Nick]

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.

[Jack]

So what was it about that moment and that place that led to three of the most iconic names in American fashion?

[Mickey Drexler]

Well, you know, I appreciate that, but I never planned it. And still, even today, I have a hard time.

[Nick]

Did your parents plan it?

[Mickey Drexler]

My parents, my. My role model. No. And, you know, I did a little research on Calvin and I found that interesting story. Cause I always. Those were the two guys. They were the ones.

[Nick]

Calvin and Ralph.

[Mickey Drexler]

Yeah. And then there was Perry Ellis and a few other people who were amazing. And Calvin's grandmother was a dressmaker.

[Jack]

Okay.

[Mickey Drexler]

She sewed, she tailored. She was a dressmaker.

[Jack]

Checks out.

[Mickey Drexler]

His mother was extremely stylish and had a lot of style and taste. And his first job was working for coat manufacturer in New York. And he was in a freight elevator one day with the coats on a rack. A woman from Bonwitteller who was a merchandiser. I love those coats. Where can I get them for Bonwit Teller. He said the name of the company and she said, who designed them? And he said, I did.

[Jack]

Wow.

[Mickey Drexler]

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.

[Jack]

But then you are 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?

[Mickey Drexler]

Well, 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. And 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. I never liked school. I daydreamed in school about things and how things maybe should be. So I. In terms of getting in, I worked in the garment. One good thing my dad did is he not. Not graciously made me work.

[Jack]

Yeah.

[Mickey Drexler]

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 chock full of nuts. I 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.

[Nick]

Wait, the razor blade was called a sword?

[Mickey Drexler]

No, Wilkinson Sword.

[Nick]

It put a sword on your face.

[Jack]

Could have run with that.

[Mickey Drexler]

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.

[Jack]

Mickey's a good salesman. I'm interested in this razor blade now.

[Mickey Drexler]

So I sold them on the street because I bought them I don't know where. And I, you know, had a little side hustle.

[Nick]

Nice.

[Mickey Drexler]

Anyway, that was a minor thing, but I. 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, million years later. But 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 were part of the Bloomingdales group, et cetera. 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 like me. I 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 and Strauss? So I called the head of hr, who I knew, and 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 $11,500 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. I 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 gotta feel that for a company you want to work for, you're a competitive guy.

[Jack]

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 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?

[Mickey Drexler]

I have. She was in those days the fashionist with her sister, whose name Lee Radziwill. 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. Brilliant. And I lived on east. Is your kid JFK Jr. No, it was her daughter.

[Nick]

Okay.

[Mickey Drexler]

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. I. And I sent her. I knew she lived at 1040 Fifth Avenue. So she was on the catalog list. She never bought a thing from us.

[Jack]

But you'd still send her the catalogs.

[Mickey Drexler]

Oh, yeah, of course.

[Jack]

Even though you knew they were getting rejected every time.

[Mickey Drexler]

It doesn't matter. You know, to me, she was who I felt I wanted us to be dress, you know.

[Nick]

And that's what amuse is.

[Jack]

And that's what amuses.

[Nick]

Yeah.

[Jack]

And does every industry need that, like every business should? You have a muse, you're designing for one person.

[Mickey Drexler]

I can't answer it because amuse has a lot of different definitions. She was an inspiration. Now and then over time, you have inspirational people. You vary. 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.

[Nick]

It's emotional.

[Mickey Drexler]

Yeah. It's all 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? Something I said, I can't explain it. I said, why don't you like chopped liver? It's like, how do you explain it? How do I explain why I like linen shirts?

[Jack]

Yeah. You don't have to.

[Nick]

So, Mickey, you're a hard working 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.

[Mickey Drexler]

35.

[Nick]

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, San Francisco, California.

[Jack]

And you were the turnaround artist.

[Mickey Drexler]

Well, I don't like that word, but

[Nick]

go ahead, tell us what was happening at the Gap and what you did to fix the company.

[Jack]

You fixed it from $400 million in sales to 14 billion by the time you left.

[Mickey Drexler]

But 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. 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. 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. And 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.

[Nick]

Not glamorous now.

[Mickey Drexler]

And it hit me, what the f am I doing here? 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.

[Jack]

Yeah.

[Mickey Drexler]

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 as a great partner. But I would commute to the city and back. And the people in the company, they. They say, oh, there's the noon flight to Hong Kong taking off.

[Nick]

Because he could see the Airport.

[Mickey Drexler]

No one would believe this.

[Jack]

You knew the air.

[Mickey Drexler]

I'm looking out. And I was there Monday through Friday from. I started Thanksgiving week, and my family and my Peggy and Alex moved in June, and I would commute every week, and it was like, oh, my God.

[Nick]

So back then, the company had 400 million in annual sales. That's a little more than allbirds did.

[Mickey Drexler]

I never really thought of. I 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 the age I didn't know from anything other than what I thought.

[Jack]

So what was the first thing you did at the Gap?

[Mickey Drexler]

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 rent cars. I was in Houston, Texas. I wanted to see the stores. You have to talk to people on the ground and work 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. It says, today, only 30% off at the Gap. Oh, boy, that tells you everything. So I walked in. Hector was the store manager. I hecked around, 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.

[Nick]

Yeah, yeah.

[Jack]

Discounting deaths, bottle of debt.

[Mickey Drexler]

Everything was discounted. Fall into the gap. Levi's, 2 for 26. Everything was on sale. So what I did, I always do this. I mean, I get together with the 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. It, 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 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. And 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 you know. But he was okay in 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 drops. 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. And I knew that if I don't know what they're talking about, then no one does. Yeah, it's a different language desk in headquarters. You know, there's a Keep it simple, stupid. I put K I s keep it simple on the 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.

[Nick]

You purged the bad inventory. That wasn't selling.

[Jack]

That was your first move.

[Mickey Drexler]

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 and they're doing rigid washed Levi's. 2 for 26. And I went to Levi's and I just changed. I said, we're buying the washed goods

[Nick]

so you improve the jeans to be Levi's quality. At least 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.

[Mickey Drexler]

They really do.

[Jack]

Jack keeps telling me this, especially when

[Mickey Drexler]

you're handsome, good looking and great shirt. I was chubby.

[Nick]

So I have a litmus test to see if people were really chubby when they were young. Here's the trivia question. I hope you know because you launched Gap Kids, what is the largest boy's gene size that Gap Kids makes? Every childhood husky kid knows the answer to this question.

[Mickey Drexler]

I don't know.

[Nick]

Sixteen husky.

[Mickey Drexler]

That's big.

[Nick]

I, I like, I clung to those 16 huskies because I didn't want to go to, like, the men's department. I was only like, 11.

[Mickey Drexler]

We started Gap Kids for the following reason, and it was a big mistake. You can't really. We made no money in that business.

[Jack]

Really. Even with Jack's family. He has three brothers who are in this husky boat.

[Mickey Drexler]

Jake, crew cuts. Both mistakes. Hard to make money. Too distracting on kids stuff.

[Jack]

I thought parents would be willing to pay. We thought that was a profit Puppy.

[Mickey Drexler]

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 was always an Oshkosh by gosh overall, which still would be great if they have and a plaid shirt. So 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 isn't you don't learn this. How to do this. So I got together the mothers because most of them were women and mothers or 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.

[Nick]

So why did that not work?

[Mickey Drexler]

To make a kids say, you want that shirt in kids 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. But in the early days we should have stopped at 10 or 15 shops maybe, but. And then it's a distraction. You know, the more things that you have to do, you know, the main thing is the main thing. And kids wasn't the main thing.

[Nick]

Interesting.

[Mickey Drexler]

Same thing with J. Crew in hindsight.

[Nick]

So after Gap Kids you would go on to launch something that worked really well.

[Jack]

Oh yeah. This was like the OG disruptor.

[Nick]

It became the fastest fashion brand to hit $1 billion of sales.

[Jack]

First brand to feel like 50 bucks, but really cost 15.

[Nick]

Old Navy.

[Jack]

Yeah, Old Navy.

[Mickey Drexler]

This is a very interesting story and it could take up the whole podcast. I'm serious. That's my favorite. Well, madewell too is 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. It'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 who's quoted cheaper, less expensive than Gap.

[Jack]

Oh boy.

[Mickey Drexler]

So it's basically a Gap knockoff, a dupe. I get on an airplane first week it opened in Mall of America. I said, I want to see what's coming here, because, you know, I'm always threatened by it.

[Nick]

This is a great start. I want to reset the scene here.

[Jack]

Talk to me.

[Nick]

So the predecessor to Target was launching something that was obviously intended to undercut the Gap.

[Jack]

A Gap dupe. The early Gap dupe.

[Nick]

And so you went to Target's home state of Minnesota.

[Mickey Drexler]

Only because I read the article.

[Jack]

Yep.

[Nick]

Only because you read the article on

[Jack]

page four of the Times.

[Mickey Drexler]

And if they didn't have that quote, there'd be no old name.

[Nick]

And you're the first guy to scope the product and say, this is a threat to the Gap. So you kind of face the innovator's dilemma there.

[Mickey Drexler]

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, focus 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 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 gonna go

[Jack]

to a little detour. On the trip to Midwest speaking, I

[Mickey Drexler]

always speak to the store people. I said, why do you have so many markdowns here? She 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 3000, 450. Every other gene in America under 30 was 80% of the marketplace. And we didn't play in that arena. We were 3,450, maybe to 4,450. 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 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

[Jack]

of business, just go spend money.

[Mickey Drexler]

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. We just want a good value, good price, and nice, close, 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 was the only. 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.

[Jack]

And how'd you come up with the name?

[Mickey Drexler]

So we didn't have a name. I'm in Paris. Have you heard the story?

[Jack]

No.

[Mickey Drexler]

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?

[Jack]

The phone lanyard on your shirt.

[Mickey Drexler]

I was in Paris, driving back to the airport with a woman I worked with. I'm in the backseat of the taxi or whatever on Rue St. Germain, and I saw ahead, like a movie marquee with lots of little neon bulbs. And we. We just drove by. I said to Maggie, I say, that's the name. Old Navy.

[Jack]

That's what was.

[Mickey Drexler]

Dive bar.

[Jack]

He's named after a dive bar in Paris.

[Mickey Drexler]

Yes.

[Jack]

That you saw in a taxi ride.

[Mickey Drexler]

And I checked the next day in back in New York or California.

[Jack]

Call your lawyers up about.

[Mickey Drexler]

No one owned it.

[Jack]

Yeah.

[Mickey Drexler]

So I registered it immediately. Now, you talk about things in corporations. The board didn't like them.

[Jack]

Oh, boy.

[Mickey Drexler]

You know, and the board.

[Nick]

The board's your boss.

[Jack]

Yeah.

[Nick]

Right, right. They can fire you.

[Jack]

And they probably want to do a focus group on the name.

[Mickey Drexler]

Yeah, it's totally common. Yeah.

[Jack]

Hire consultants.

[Mickey Drexler]

I mean, it's totally common in that

[Jack]

sense, but you won that battle.

[Mickey Drexler]

I'll Tell you how 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.

[Nick]

So the Gap was a publicly traded company.

[Mickey Drexler]

Yeah, but.

[Nick]

But a San Francisco family controlled by the family.

[Mickey Drexler]

And they had. And I'm so friendly with the three sons of the founder, but. So they didn't like the name Old Navy. And then they said, they. I'm not mentioning names because there are names involved here.

[Jack]

That's fair. That's fair.

[Mickey Drexler]

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?

[Jack]

What?

[Mickey Drexler]

Gap Warehouse. Old Navy.

[Jack]

That was the original name.

[Nick]

I don't like. I don't like Gap Warehouse.

[Jack]

That's very wordy. It does not roll off the floor.

[Mickey Drexler]

And I said, there will be no Gap in five years. You call the Pepsi the Coke and that.

[Jack]

Yeah.

[Nick]

This kind of reminds me of J. Crew Factory, which I also don't like because.

[Jack]

Because I bought the record when I

[Nick]

was strapped for cash. I bought J. Crew Factory sweaters thinking they'd be J. Crew quality.

[Jack]

But it wasn't.

[Mickey Drexler]

No, never. Yeah.

[Nick]

And I think a similar thing could have happened to the Gap there. If it was called the Gap Warehouse

[Mickey Drexler]

and people bought it, then the Gap cannibalizing your business.

[Nick]

That would have cannibalized.

[Jack]

Right. And it was a different thing, too, because the Old Navy did have more surprising things. Like, I have a. A bag that's made out of basketball leather. Like, 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

[Mickey Drexler]

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 I. 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. The Schwins, they were all yellow. So I still have one in my garage. Sold out. But that's the kind of thing, the unexpected, the treasure hunt. Always better than the expected in anything.

[Jack]

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, shooting a basketball.

[Nick]

Did Old Navy have shopping carts or were there big bags?

[Mickey Drexler]

I'm remembering big bags. It's a good question. I don't remember.

[Jack]

Well, you were getting all the husky clothes, Jack. Your family was loading up with the four sons.

[Mickey Drexler]

It didn't make them 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 so friendly with, and we opened up a coffee shop.

[Nick]

Well, launching kind of cooler sister brands underneath the big parent company is kind of your thing.

[Jack]

Yeah, like, madewell is like a multi billion dollar jeans brand, all American brand right now. But it started in this insane way with you, like personally buying TL.

[Nick]

Dr. Mickey moves on from the Gap to J. Crew, and Madewell is his baby. But before you started J. Crew, you personally acquire the name Madewell. How did that go down?

[Mickey Drexler]

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.

[Jack]

His job was. He was a wash expert. He's a ripped jeans connoisseur.

[Nick]

I have a faux tear in my back pocket.

[Jack]

Yeah, that was precision that he did. That was his art and his science.

[Mickey Drexler]

So David calls me one day, we met. He shows me a wooden sign with Madewell logo. It's wood and since 1937, he said, what do you think of the name? I said, I love that Made. Well, 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. But. And I said, yeah, I would like to buy it. Oh, and the price, that was very.

[Jack]

Can you share the price?

[Mickey Drexler]

It was 125,000.

[Jack]

So you bought. You bought the name Madewell, which was based off a factory in New Bedford, Massachusetts, for 125 grand. You personally just bought it because you liked the sound of the name.

[Mickey Drexler]

And finding a great name like Old Navy. It's a great name. Yeah. A name has to belong to the product name Storming. And it's what you call it, Name Storming.

[Jack]

Yeah. Coming up with the name.

[Mickey Drexler]

But. 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 we did Ludlow suits at J. Crew. It was Ludlow Street.

[Jack]

Yeah. On Lower east side.

[Mickey Drexler]

And you know, I want things to be named after streets, after this, after names that connect.

[Jack]

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. And each of those names, you don't need to know what they sell. They give you a feeling no matter what.

[Mickey Drexler]

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.

[Jack]

Now a quick word from our sponsor,

[Nick]

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[Jack]

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[Jack]

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[Nick]

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[Jack]

so, Mickey, you have gotten your big break at Ann Taylor, Jack's mom's favorite brand. You've transformed the publicly traded Gap Co. Into a $14 billion from a loser

[Nick]

to a winner behemoth.

[Jack]

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.

[Nick]

Yeah, 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.

[Jack]

Yeah. Because you'd just been at a wine party in Napa wining and dining and schmoozing with the guy Steve.

[Mickey Drexler]

Who? 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 Napa. We had a home there. He was at the party and we schmoozed. And I'm thinking, you know Steve Jobs. You know, we schmooze that.

[Jack]

Dot, dot, dot. Was a lot of cool stuff happening.

[Nick]

Was his black turtleneck a Gap?

[Jack]

No.

[Mickey Drexler]

No.

[Jack]

Was he wearing it at the wine party?

[Mickey Drexler]

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.

[Nick]

So you two bond over both being micromanagers, right?

[Mickey Drexler]

Well, his mission. He had a mission and he. For a year we chatted and I said no about joining his board. Because, you know, at that point I was stupid.

[Jack]

Steve, wait, Steve Jobs asked you to join the Apple board?

[Nick]

And he said. He said no. That is stupid.

[Jack]

You said, you denied Steve Job.

[Nick]

As far as I'm aware, being a board member of a publicly traded company is three to six hundred thousand dollars a year in salary.

[Jack]

It's a good gig for six to

[Nick]

twelve meetings a year. Am I summarizing this incorrectly?

[Mickey Drexler]

There's all the stock there, options, but not too shabby I was very fortunate. 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 were 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. And it only lasted until I was fired. It was about a year. And he's the one. So anyway, he wanted. We designed the store.

[Nick]

What store?

[Mickey Drexler]

The first Apples. He had a story show me was really ugly.

[Jack]

So Steve Jobs shows you a design for this Apple Store concept and you think it's ugly.

[Mickey Drexler]

It was ugly.

[Nick]

Wow.

[Mickey Drexler]

And I said, it'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.

[Jack]

Yeah.

[Mickey Drexler]

Because timeless for me, in clothes, in design never goes out of style.

[Jack]

But I gotta ask you, we've all been to the Apple Store. The Apple Store has not changed in decades.

[Nick]

At this point, it's the same wooden tables, white walls, a lot of beautiful glass everywhere.

[Mickey Drexler]

Yeah.

[Jack]

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 you designed it.

[Mickey Drexler]

You know, it's kind of like the chopped liver question. There's no answer to that. It's kind of. You feel 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, you 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. 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.

[Nick]

That would have been such a great Instagram collab post when you and Steve Jobs announced you're moving into each other's boards.

[Jack]

Oh, yeah.

[Nick]

That would have been cool.

[Jack]

I can picture the photo out now. So, Vicki, you've 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.

[Mickey Drexler]

Steve called me first.

[Jack]

He did.

[Mickey Drexler]

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, whatever. So I get home at 9. He goes, Call Don, you're getting fired tomorrow morning.

[Jack]

Wow.

[Mickey Drexler]

I said, no wonder they didn't look at me at all tonight. We were showing the best goods. I knew it was a turn. You know, there's three companies and I looked 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.

[Jack]

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.

[Nick]

But all of the growth that you sustained at the Gap transitioned to J. Crew once you started there and the Gap started flatlining.

[Mickey Drexler]

Right. I think the Gap's still doing the same volume they did 20 years ago.

[Nick]

Yeah, about $16 billion.

[Jack]

The first thing you did at J. Crew, we noticed though, is you did something we've never seen another CEO do. You put a PA system into the headquarters.

[Nick]

Loudspeaker.

[Jack]

Loudspeakers, like on every floor. You know, this is Mickey chiming in

[Nick]

like the Princip in a middle school.

[Jack]

Happy Friday, everybody.

[Mickey Drexler]

Do it before. Why?

[Jack]

What is it? Why did you. Because that seems like a micromanager kind of move.

[Mickey Drexler]

I 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 loudspeaker, 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.

[Jack]

It feels like it's wasting time.

[Mickey Drexler]

And so I said, I moved my office into an open space right outside the closed office. Cause I hated being there alone. And I was in the middle, which I did a gap towards the end. And I said, I want a loudspeaker because no one's returning my call.

[Nick]

Well, Mickey, we're publishing this episode on America's 250th birthday.

[Jack]

Well, the annual tradition of the Old Navy American flag tee, that is literally American style because you splattered it right on there. But, you know, we see you as also the more general visionary of American style and fashion. So more broadly, like, what is American style? Mickey Drexler.

[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. Yeah, they 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 old fashioned one, you know, the Grand Wagoneer. I mean, the Woody. They should still be doing a Jeep Woody.

[Jack]

Oh, that would be classic.

[Mickey Drexler]

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?

[Jack]

It's like we say, the 20 year rule of nostalgia. You know, the nostalgia moment becomes novelty.

[Mickey Drexler]

I would love to have a Jeep brand. See, the same thing connects to Gap and J. Crew in a way. There's a sense of brand and emotion and what you have to do, try to bring it back.

[Jack]

Well, there is one catch there, and it's something Jack and I call the three Fs of fads.

[Nick]

We believe after studying business news for 10 years 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.

[Jack]

As a Lululemon shareholder, I can, I can tell you that firsthand. So we were curious. As a fashion leader, do you agree?

[Mickey Drexler]

I'm sick and tired. What was the vegetable that everyone was eating?

[Jack]

Was it Kale? Radicchio? Asking the production team.

[Mickey Drexler]

You know, but it's true. I don't like being in that.

[Jack]

Well, you're in that business, so how do you.

[Nick]

Yeah, 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.

[Mickey Drexler]

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.

[Jack]

It hasn't changed.

[Nick]

That's timeless. That's unique.

[Mickey Drexler]

But no, I, 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, I blew it. And then I have a bad year. Stock market punishes you with a bad week. Everyone's forecasting earnings. But I, I, I don't think that way. If I did, I'd get into trouble.

[Jack]

So if the way you defy fads is just constantly reinventing because I can, is that the answer?

[Mickey Drexler]

I'm trying to think what a fad is. There's a million of them out there. Like, I look at some without mentioning names. I look at names on a sweatshirt. It's a fad.

[Jack]

It'll die quickly if it's a name on a sweatshirt.

[Mickey Drexler]

The more you show. People love 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 designers, people not, not at that level anyway. You see it coming and going. When I was a kid, young guy, starting out was a big effing deal. When I bought my first pair of the Gucci buckle shoe in Florence, the slip on or whatever, I walked. I say, I'm rich now, you know, because it was. But now what's unique is scarcity.

[Jack]

And it's no longer scarce.

[Mickey Drexler]

Well, nothing. A logo unscarces. I mean, you know, But I can

[Jack]

see your style of reinvention right now, because for the yetis listening, Mickey's coming here impeccably dressed in a classic Alex Mille 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 designed for an iPhone case.

[Mickey Drexler]

And the hard thing about this business is you gotta keep doing it.

[Jack]

Okay, but then how do you make that decision? Cause 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, grasp versus guts. How much of it is imagining versus engineering? Do you go with your gut?

[Mickey Drexler]

All of the above. But it starts with vision. And look.

[Jack]

Did you look at the data?

[Mickey Drexler]

Basically, of course, the data tells me everything I need to know. I was very good in math. Not science, by the way. But, you know, if you look at, I don't know, If AI does this, if you feed in information that's today, it'll forecast it out. But 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 they 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, 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? I said, you should have bought at least 40% of the buy in this color. How do you know that? You know it.

[Jack]

So 90% of your decisions are database.

[Mickey Drexler]

They're always part of. Because it's DNA. I look at the information.

[Jack]

That's your gut.

[Mickey Drexler]

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. But on this one, it was once you. We got it. It was database. 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. 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. And it's not a science, but you have to forecast how many you think would sell. And then you have to. And then you have to protect the downside. But data is absolutely for me, religion.

[Jack]

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?

[Mickey Drexler]

It doesn't have emotion. It can have taste.

[Jack]

Well, one thing AI could not do is play a salesman on Breaking Bad season two. It couldn't have pulled that off?

[Mickey Drexler]

Never. And I only heard bucks for that.

[Jack]

And the residuals keep coming in the checks.

[Nick]

So, Mickey, to wrap up your epically fashionable resume, Abraham and Strauss, Bloomingdales, Ann Taylor, the Gap, Gap Kids, Old Navy crew.

[Jack]

You've covered every generation here.

[Nick]

We'd love to wrap it up with some rapid fire questions.

[Jack]

Yeah, we got some special ones whipped up for you.

[Nick]

What is a timeless fashion piece that every man needs five pocket pair of

[Mickey Drexler]

jeans that fits him in the right wash. He needs white shirts. See, I wear this shirt 2014.

[Nick]

You bought that in 2014.

[Mickey Drexler]

Still wearing 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.

[Jack]

The best timeless fashion piece every woman needs.

[Mickey Drexler]

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 don't. I'm not qualified to say that. I know it when I see it.

[Nick]

Always.

[Mickey Drexler]

But, you know, I like things that are forever.

[Nick]

What's the best fashion brand? That's not one of the ones you've

[Jack]

worked for, which doesn't leave many. By process of elimination, I'll tell you

[Mickey Drexler]

who I say the best fashion brand is. T.J. maxx. Oh, you know what? $60 billion. They have real prices. And if you look at our industry, 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.

[Jack]

Best business book you've ever read.

[Mickey Drexler]

You know, I just finished Phil Knight's book ten years too late.

[Jack]

True dog. Great book.

[Mickey Drexler]

I'm not a big reader, but I. I like that. I like to stick the detail.

[Nick]

What's the best restaurant in New York City?

[Mickey Drexler]

I have none. Best. I don't have the best.

[Jack]

Best restaurant in the Bronx.

[Mickey Drexler]

Well, it's probably on Arthur Avenue, but I don't go there anymore.

[Jack]

What about the restaurant where you control the playlist?

[Mickey Drexler]

Oh, Saint Ambrose.

[Jack]

Oh, lovely.

[Mickey Drexler]

I like that.

[Jack]

Principesa cake.

[Mickey Drexler]

Yeah.

[Jack]

You know that's best business leader you admire?

[Mickey Drexler]

Well, I loved Steve. Steve the best. And he was quirky and difficult, but he cared about the products. That was first and foremost. Foremost in every board meeting. He cover it with a gray cloth. And then he'd make the presentation. Wow. So he was. And look what he's done. I miss him.

[Nick]

We miss him, too. And if you, Mickey Drexler, were a stock and we're gonna IPO you personally, what would be your three or four letter ticker symbol on the stock market?

[Mickey Drexler]

That's a hard one.

[Nick]

You know, Shoe. I think we should tell everyone to drink every time he says simple. So maybe smpl.

[Mickey Drexler]

Yeah, that.

[Jack]

Yeah.

[Mickey Drexler]

Smp. Simple.

[Jack]

Coat. Coat Works too.

[Nick]

Yeah.

[Mickey Drexler]

Or Hamisha. That's too long.

[Jack]

And finally, Mickey, before any guest leaves, we always ask them to whip up the takeaway.

[Nick]

So, Jack, what's the takeaway on Mickey Drexler and American fans?

[Mickey Drexler]

I never had a grand plan to be who I am today. In fact, when I'm objective, I quite anxious about keeping it up. So 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.

[Jack]

But make today the best one yet.

[Mickey Drexler]

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.

[Jack]

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.

[Mickey Drexler]

Oh, really? Is that what you do?

[Jack]

Thank you, Mickey.

[Nick]

Bero premium non alcoholic beer.

[Jack]

All right. Yet he's a little behind the scenes here. Before our New York City live show back in April, Jack and I went sober for two weeks. True story.

[Nick]

Couldn't risk getting sick. I didn't want to be groggy. I couldn't afford a hangover. It was New York, baby.

[Jack]

Okay, But Jack, celebrating the wins is what we do. And so for our live shows, we crack open something special.

[Nick]

So we drank Bero, the premium non alcoholic beer brand co founded by Tom Holland.

[Jack]

Yeah, 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.

[Nick]

And if it's good enough for the actor who played Spider man, it's good enough for us.

[Jack]

You see, it pairs well with a pickleball game, a profitable earnings report, or we with the best podcast.

[Nick]

So, Yetis, if you wanna celebrate the wins with all the taste of a premium lager or ipa, but none of the alcohol, there's no better choice than beer.

[Jack]

Okay, pause the pod. Did we mention the can is straight up gold? This thing will stand out at every one of your next parties. Trust us, we've done it.

[Nick]

Only beer we know that actually upgrades the scene like a promotion.

[Jack]

So, Basties, if there's a win you're celebrating every day, Beero is the non alcoholic brew brand you gotta bring.

[Nick]

So use code t boy for 20% off your first [e-mail].