The Man Who Dressed America: Fashion Legend Mickey Drexler

Summary

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The Messy Parts with Maryam Banikarim

Episode: The Man Who Dressed America: Fashion Legend Mickey Drexler

Date: February 16, 2026

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Episode Overview

This episode of The Messy Parts features a candid, wide-ranging conversation with fashion icon Mickey Drexler, the legendary CEO behind The Gap, J.Crew, and currently, Alex Mill. Renowned for his sharp instinct and creative drive, Drexler reflects on his unconventional journey to the top, the hardships and personal histories that shaped his resilience, and the many 'messy parts' along the way—including seismic firings, family dynamics, and his philosophy about what it really takes to build innovative brands and enduring careers.

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Key Discussion Points & Insights

Early Life and Upbringing ([03:39]–[06:11])

• Mickey discusses growing up in the Bronx, losing his mother at 16, and a difficult relationship with his father, who worked in the garment industry but was “not a nice person.”
  • Quote: “He didn’t fit the job description of a dad. … The only thing he did well, good for me, was force me to work.” —Mickey Drexler [03:42]
• He credits his complicated home life and adversity with instilling a "million percent" of his drive. He notes a preference for people who've come through adversity.

Education, Early Career, and Mentorship ([06:12]–[08:16])

• Mickey describes his disdain for purely academic achievements, including MBAs (“It’s a waste of time.” [06:15]), and his lack of early mentors or role models, making his own way.
• The importance of being "Hamisha" (down to earth) and a "Mensch" (good person) in business; he strives to return calls and not act like the “big shots” he disliked.

Major Breakthroughs: Ann Taylor, Gap, and Leadership Style ([09:17]–[13:22])

• Mickey recounts turning down the Ann Taylor CEO job twice before taking crucial advice from a more senior friend—“Better off being the CEO of a $25 million company than the VP of a $500 million company.” [10:05]
• Early lessons in corporate politics and recognizing undervaluation shaped his subsequent choices.

Gap Years: Turning a Business into a Juggernaut ([13:22]–[20:47])

• Mickey led Gap’s transformation, founding Old Navy and tripling down on instinct-driven, customer-centric strategy rather than bureaucracy.
  • Quote: “I marry a company, and it’s always long term.” —Mickey Drexler [12:54]
• He describes the experience and instinct that made him successful, emphasizing daily learning and intuition.

The Firing at Gap: Betrayal, Politics, and Resilience ([14:01]–[21:50])

• Drexler details being abruptly fired after 18 years—even after taking revenues from $400 million to $15 billion—via a terse note from Don Fisher with no “thank you” ([20:43]).
  • Quote:
    • Host: “When you came in, what was the revenue of the company?”
    • Mickey: “$400 million.”
    • Host: “And what was it at 18 years later?”
    • Mickey: “$15 billion.” [00:01, 00:05 and again at 20:13-20:16]
• Steve Jobs privately warned him beforehand; Mickey attributes his ability to see around corners to his instinct.
  • Quote: “The instinct and intuition is the most important traits I have. I see around corners.” [14:44]

On Termination and Corporate Culture ([21:50]–[23:06])

• Mickey reflects on corporate mercenaries, private equity, and the lack of empathy in major companies.
  • Quote: “I don’t like big corporations unless there’s a real person running them.” —Mickey Drexler [22:21]
• He contrasts his own style of firing (with respect and openness) to the cold treatment he received.

Reinventing with J.Crew and Beyond ([23:06]–[27:37])

• Fueled by “fury” at how he was dismissed, Drexler took on J.Crew, owned a stake in Madewell, and re-energized the brand, notably spotlighting creative director Jenna Lyons.
  • Quote: “I couldn’t have done it without her [Jenna Lyons].” [24:41]
• He describes subsequent painful experiences with Outdoor Voices’ dysfunction and with launching Alex Mill, his current venture started by his son.

Starting Over with Alex Mill ([27:45]–[28:50])

• Lessons on startup life: Unlike the critical mass at Gap or J.Crew, Alex Mill began as “total unknown.” Funding and attention were far harder to secure; the business had to grow organically through improving its product.
  • Quote: “I didn’t have the bank of Gap or J.Crew, you know, and I was funding it. … But what happened is the goods got better and better and better.” [28:29–28:50]

Career Advice and Reflections ([29:04]–[32:44])

• Key advice for young people:
  • Hire your boss: Trust your “instinct, trust your judgment.”
  • Be careful who you partner with.
  • Don’t overrate “fancy degrees, fancy colleges.” [31:20]
• On firing: “Be direct, be kind—a lot of times, somebody just outgrows a job.” [22:52–23:03]
• On confidence crises: Assess if you have confidence in the person first; general advice is less useful.

Instinct vs. Artificial Intelligence ([31:52]–[32:04])

• Mickey has just started using ChatGPT. He debates whether AI will “kill instinct,” but voices skepticism.
  • Quote: “I’ve had a big argument on that. I think [AI] will.” [32:04]

Working with and Learning from Steve Jobs ([32:08]–[32:44])

• Learned “no fear” from Jobs—utter confidence and cultural omnivorousness.
  • Quote: “He just didn’t let anything stop him. … He was a great salesperson and a genius, and he was the smartest guy in the room.” —Mickey Drexler [32:08]

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Notable Quotes & Memorable Moments

• On instinct and adversity:

  “I was born with a drive to be the opposite of my father. … I think all good things come out of depression and whatever.” —Mickey Drexler [15:26, 16:31]

• On being fired:

  “To be fired the way I was fired was the messiest and bad taste and bad style.” —Mickey Drexler [31:09]

• On taking meetings and curiosity:

  “I spend every day speaking to strangers and like friends of people I know, the sons of this. You’re always taking input. … I always learn something.” [30:02–30:17]

• On starting over:

  “You know, you can’t fix bad people.” —Mickey Drexler, on Outdoor Voices [27:37]

• On what makes the difference:

  “If you don’t take the shot, you can’t score.” —Mickey Drexler [26:37]

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Rapid Fire Segment Highlights ([30:26]–[32:56])

• Biggest mistake: “Be careful who you partner with.” [30:29]
• Habit to change: “Not trusting as much as I trusted.” [30:45]
• Career myth: “Fancy degrees, fancy colleges.” [31:20]
• Messiest moment: “Being fired with no notice—a 10 out of 10.” [31:09]

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Conclusion & Takeaways

Mickey Drexler’s journey demonstrates that the path to success is often nonlinear—full of adversity, political missteps, and necessary reinvention. His hallmark is combining instinct, curiosity, and hands-on humility, refusing to be shaped by the bureaucracy that ousted him. For aspiring leaders or creative professionals, Drexler’s key advice is direct: Trust your gut, learn constantly, don’t idolize credentials, and—above all—be a mensch.

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Most Memorable Quote:

“I never had anyone who mentored me. … My best compliment is two Yiddish words, which are Hamisha and a mensch.” —Mickey Drexler [06:03–08:16]

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For further insights—and the full, characterful dialogue—listen to the episode for Drexler’s signature authenticity, humor, and candor.

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Transcript

[A]

When you came in, what was the revenue of the company?

[B]

The revenue of $400 million.

[A]

And what was it at 18 years later?

[B]

$15 billion.

[A]

I know you don't like the word turnaround, but you really like hockey stick their business up. You go in to see Don and he gives you a card with one line, basically letting you know, like, thank you so much. Here's the door. I guess what I want to know is how did that feel?

[B]

How did it feel? Well, it was what the.

[A]

Today on the messy parts, we're going to have on Mickey Drexler. He was the CEO of the Gap in the 80s, then went on to turn around J. Crew, and today he runs Alex Mill. The reason I love that Mickey Drexler came on is because when I was in college, he had a campaign running for the Gap called Individuals of Style. It was an iconic campaign, so iconic that Richard Dixon and his team have brought it back today at the Gap.

[B]

And.

[A]

And I had this idea of combining a travel guide that I did, which was an insider guide to cities, with his campaign. I mock it up, I mail it to him because this is pre Internet and it's the finals in my business school class. And the phone rings and it's Mickey Drexler. This led to me meeting Mickey Drexler. And in fact, I often say Mickey Drexler started me on my career in marketing because I wasn't looking for a job at the Gap. I just wanted them to do the guide. And he said to me, this is a marketing idea. You should go into marketing. He is a man who is all about creativity and instinct, which makes a lot of sense when you think about the fact that him and Steve Jobs, they were so tight, they actually convinced each other to be on each other's board. This is a conversation that is all kinds of things, but you're going to want to listen. And partly, I want you to know that Charlie, he really did think Mickey was a dog whisperer. So he was very active, and I think he hit the spilkes, which is a word that Mickey talks about. I can't wait for you to hear. I can't tell you, Mickey, how excited I am to have you here in the house on the blue couch. You and I have a funny backstory, which is that you were CEO of the Gap, the Individuals of Style campaign, which is kind of back, you know, however many years later. I created a mock up of that ad campaign and mailed it to you. And it was the middle of the finals, and the phone rang and you.

[B]

Called that's what I do.

[A]

Which I now know is totally what you do. And we ended up.

[B]

You never know when you make the.

[A]

Call that would have been in 1991. And you never know because here you are on my couch, many years later. And while I never sounds like you're.

[B]

A psychiatrist, here I am on your couch.

[A]

But which I know, your wife Peggy's a psycho. It's just a whole full circle moment here.

[B]

Well, now she's a documentary maker.

[A]

Okay. All right. Well, so we've already covered a lot of ground in this conversation, but I remember so distinctly that phone call. Cause it was really, I say, before the Internet, I'd mailed you a book, and you called. And I have often said in interviews that that exchange. And you're introducing me to Susan Cooper, who was. Was head of recruiting for you, really started me on my career because you both said to me, this is a marketing idea. You should go into marketing. And so here we are. Now, I'm a podcaster, so who knows? I obviously know about your incredibly iconic career, but what I want to talk about a little bit is sort of how you started, right? You grew up in the Bronx. I read that you lost your mom when you were 16. I lost my father when I was 17, which you may not know. And, you know, you had a complicated relationship with your dad.

[B]

That's a nice way to put it.

[A]

Well, how would you put it?

[B]

He didn't fit the job description of a dad. And he wasn't that nice to my mom. He wasn't nice to me. And I kind of give him credit for my success today to a degree. But, you know, he wanted to be successful. He acted like a big shot. We lived in the ground floor apartment in the Bronx. I slept in the foyer area, the entry area, and he worked in the garment business. He always acted like, you know, he had a lot of bills and all that, but wherever that came from. But he worked in the shipping room, and he was just not a nice person. The only thing he did well, good for me, was force me to work. As a kid, I used to work in the shipping room where he worked at a junior coat manufacturer in the garment business. So I had a work ethic. And my mom was very depressed. She had lived with cancer for many years.

[A]

So you think that sort of that complicated upbringing was part of your drive?

[B]

A million %? Not even 100%. I like people who have had adversity. I skewed towards them in who I like meeting. Because today, you know, it's A different environment, a different generation because I had to do certain things. You know, I went to public schools. I went to Bronx Science, which made a difference in my life. I went to City College and then I kind of got out of town. College grades, board scores, I couldn't care less. I like a college degree, but on the other end, there's a lot of successful people who haven't had them. I grew up kind of being anti fancy people. Even today I am kind of that.

[A]

Way. Although now you might be a fancy.

[B]

Person. Well, you know, it's interesting. People respond to me like that and. But I respond to them, I call them back. And that's the same old me because I never had anyone who mentored me. I didn't have role models. Eight cousins. I'm the only one who went to college. Jewish in the 60s. Pretty amazing because the educational ethic wasn't.

[A]

There. So you didn't go to business school and I did. Did you go to business school.

[B]

To stay out of the.

[A]

Draft? Oh, I didn't find.

[B]

That. That was my.

[A]

Mission. Okay, but did you think business school helped.

[B]

You? No. It's a waste of.

[A]

Time. Do you still think that? Yeah, because all these kids who are graduating and we're not quite sure what the job market's going to look.

[B]

Like. You have an.

[A]

Mba. I.

[B]

Do. Yeah. I.

[A]

Know. That's when I met.

[B]

You. Did it help.

[A]

You? It did. Well, first of all, if I hadn't been there, I wouldn't have known you came to speak at Columbia and I wouldn't have met you. So maybe. So it's interesting you have two.

[B]

Children.

[A]

Yes. And I assume they did not have the kind of adversity you had growing.

[B]

Up.

[A]

No. Do you worry about them? Because I think about that I also had adversity growing up. And I worry about how you pass that resilience on because I think that that dysfunction is part of my journey and.

[B]

Success. I think no one escapes from whatever it is. You know, people can say this, that my son grew up and he works with me now, which is not easy for him. I had a good trainer in my dad to not ever be like him. In fact, I say that about people I work for. I mostly learn from people. I really don't find that. I never had a boss I really admired in my first 12 years. I think my kids, they have their issues, but who.

[A]

Doesn'T? Who.

[B]

Doesn'T? But they're nice kids. They're nice. Well, kid Alex is 47. Katherine's in her mid-30s, but they're they're nice, and they have good.

[A]

Values. Okay, so you do 12 years. You're definitely known for paying attention to lots of details, including, obviously, picking up the phone and calling.

[B]

Everybody. It's very important, because I never want to be the big shot, because I didn't get a lot of calls back. I didn't get the big shots. When I went up the escalator in Bloomingdale's. Hi. I said to myself, well, I work for you. Hello. They didn't say hi. But I. I don't want to be that person. And in my opinion today, most of those people are. Are that.

[A]

Person. Who's most of those.

[B]

People? CEOs, CEOs, chairmans, bureaucrats. But I didn't want to be like them, because my best compliment is two Yiddish words, which are Hamisha and a.

[A]

Mensch. Oh, I know what mensch.

[B]

Is.

[A]

Yeah. I don't know what Hamish.

[B]

Is. Down to earth, you know, if you look it up, you'll see what the exact definition.

[A]

Is. Okay, so that was clearly always part of your personality. You get to the Gap, and it's a big.

[B]

Turnaround. Well, I'll tell you my personality. I was painfully.

[A]

Shy.

[B]

What?

[A]

Yes.

[B]

When? As a kid growing up, I was always shy. Into my 20s, actually, probably in my 30s. I was always, like, reticent. But I worked a lot hard. I worked hard, and I guess I worked very smart at Bloomingdale's, but it didn't come out of my shell. I was.

[A]

Older. So were you at the Gap at this.

[B]

Point? I was at the Gap. I was at Ann Taylor when I was 35, became the CEO. I turned down the job twice. CEO of Ann Taylor. I was 35. Worked in a department store job, which I hated. And I.

[A]

Always. Why did you hate that.

[B]

Job? Bureaucratic. And I was looking for someone I admired to work for. Yeah. I mean, and I had this sense, and, you know, I admired Bloomingdale's. My first boss, two levels up. I really liked him a lot, but I liked him because he liked me, and we had a nice relationship. But in terms of the business, no, I never, never had someone I really.

[A]

Liked. You take the job at the.

[B]

Gap? No, first Ann.

[A]

Taylor. Ann.

[B]

Taylor. I was having dinner at home with someone who was much older and more successful. You know, you have friends when you're young, like, they're big shots sometimes. He was a big shot. I told him what was going on. I said, well, I was offered the head of Ann Taylor job, and I said, I've turned it down. Twice he said that night, take the job. Better off being the CEO of a $25 million company, then the vice president of a $500 million company. And the next morning, I was so nervous, I called the president of the corporation, Manny, and I said, is the job still open? He said, yes. And I said, I'll take it. Changed my.

[A]

Life. So he was right. Your friend was right about.

[B]

That. Yeah, I don't talk to him anymore, but it did change my.

[A]

Life. But he gave you good.

[B]

Advice. That was it. That the advice was that it was like it made sense. When you're a young person, you don't think you're what you think is necessarily right. I worked at A and S on a summer MBA job. I did great. So I thought I fell in love with the job and the environment. And so when they came to offer me a job out of graduate school, they offered me $11,000. And I was going to take it, of course, and whatever. And. And guy I knew in the class, I wasn't even friendly with him, said, can you fix me up with ans? I said, sure. I called the head of hr. He interviews, and when I ran into him later, he says, oh, I got the job. Thank you. They're paying me 11,500. I was fucking furious. There was something there that I didn't.

[A]

Like. What was.

[B]

It? What makes him better than me? I worked there for three months. I did a great job. I was well liked. And they give him $500 more. It was a signal to me, a tell. I interviewed at Bloomingdale's. I really had good interviews. I liked the vibe of the company. They were pretty desirable then. And so I took the job there and then. I was very lucky because the first day I was in housewares, whatever, I didn't know what a pot in the pan was. And the second day, they put me into a junior sportswear shop as the buyer because Barbara, the buyer, was on maternity leave. And I ran it. I did that for six months. I loved it. I was on my own.

[A]

Completely. So you go to the Gap to do a.

[B]

Turnaround? Well, I don't call anything a turnaround. I.

[A]

Went.

[B]

Really? Yeah. I.

[A]

Don'T. Because you did a turnaround at.

[B]

J. Crew. I don't use the word turnaround.

[A]

Ever. Why.

[B]

Not? I'll tell you why. I think it's a short term word. People say I turn companies around. I don't. I. I marry a company, and it's always long term. Now, at Ann Taylor, we were taken over by Allied Stores. Anytime a big corporate company takes over creative company, they strip it of all cultural ways and they don't understand creativity. I'm allergic to big.

[A]

Corporations. You were the CEO of a big.

[B]

Corporation. Different. And that's why I did well, because I never forgot or forget who I was. But I was in the stores every week. Because who do you learn from more than a salesperson who's dealing with a customer? God forbid, at Bloomingdale's, Macy's, A and S, someone would walk on the floor to talk to the associates who work there. Anyway, I was 18 years at Gap, started Old Navy, and they owned Banana Republic. I think you know, I was fired one.

[A]

Day. Yes, I. I.

[B]

Remember.

[A]

Right. Because we lost touch. And I called you after that news because I remembered that you'd been seminal to me. And I feel like moments when bad things happen, those are sort of the moments you reach out. But by the way, I also remember that Steve Jobs gave you the heads up.

[B]

Because.

[A]

Yep. You were on his board and he was on the Gap.

[B]

Board. And they wouldn't tell him until they legally had to tell because.

[A]

They. So he. He got it and he sort of gave you the call like, hey, heads.

[B]

Up. I came back from a board dinner. I'll never forget. We had a bad year. Who doesn't? Might even been a recession. And I knew the turn was in. You could feel.

[A]

It. I just want to say we all feel it before it.

[B]

Comes. Right, Exactly. It's the.

[A]

Instinct. I've been.

[B]

There. No, the instinct and intuition is the most important traits I have. I see around corners. We had this young guy came in. I knew his father had Uggs, worked with me. Can you speak to my son? So he sends me a list of 10 or 15 questions. Today I spent about an hour with him, Olga's dad, you know, I know him. And the. And the questions were, how do I get to be a merchant? How do I do that? I have them on the email if you want to see them. But what am I going to tell him? And I say this. There is something you're born.

[A]

With. What were you born.

[B]

With? Well, besides misery and anxiety.

[A]

Yes. Well, those are things that, you know, we can put to good use.

[B]

Apparently. Right. I was born with a drive to be the opposite of my father. I didn't know that until, in hindsight, he was bitter, he was angry, and he wasn't a nice person. And when I did the payroll once in the code company, he'd act like a big shot all the time. I was 16. Take the payroll to the bank. I said, wow. So I get down the freight elevator, I walk out into the next freight elevator and I go through every pay.

[A]

Stub. So he found out how much.

[B]

He made and he was one of the lowest paid guys there. And it devastated me because he dressed very well always and he acted like a big shot. We didn't live like big shots live. I'll never forget how depressed I was from that. But I think all good things come out of depression and whatever.

[A]

Else. What was the instinct that you think you were born with? Because you talk about that a lot. Because when we met you were like, I don't believe in marketing or research. It's just.

[B]

Instinct. This is a strange story. And I. I didn't realize it. When I was 10 years old, my father bought a new Buick Special Two Door. And he ordered it red with a white top. And then we went to pick up the car. I'll never forget this. I look at the car and it's red with a cream top. I was so upset and I hated that car because the top was the wrong color. I remember that as kind of a telling moment for me. I never thought about it as a kid, but you kind of look back in hindsight. What the.

[A]

Heck? Okay, so I'm going to go back to the story because we digress, which we're good.

[B]

At. I digress a.

[A]

Lot. Well, that's what we do. I think it's a sign of creativity, so. Or at least I'll go with that. So you have an instinct. You sort of know things are not great on the business. So you're not completely surprised when Steve Jobs calls you to give you the heads.

[B]

Up? No, I wish I wasn't surprised because I was looking for new president of the Gap division. So they have me interview at my home in San Francisco on a Saturday. Woman who was the chief merchant at JC Penney. She came in and for me, I really have a thing about. I like them or I don't with people. Interviews, five minutes. In fact. I just know about people. Magus. I spent my whole life either living in my fantasies or thinking about people or whatever. Then I get a call from a director. Now, this is the Chief Merchant at.

[A]

JCPenney. Yeah. Why is a director calling you about.

[B]

That? He wanted to know what I thought of her. I knew something was up. They're looking for her to replace me. Wow, that was a.

[A]

Feeling. Had you gotten the call from Steve.

[B]

Already? No, I got home at 9. Yeah, Steve was never. He didn't go to the board Meetings. Never went anywhere with them. Anyway, I got the call at night. He goes, you're getting fired tomorrow. Go call Don. I said, you know, I said, no wonder they. They couldn't look at me. And I called him. He got nervous because they do lawyers coming to see me at 8 in the morning. Hands me one note. It says, effective today or tomorrow. Not a nice note, just a one sentence. This is your last.

[A]

Day. You were fired. Via sticky. That's.

[B]

Amazing. Via. What did you call.

[A]

It? Sticky. A little sticky.

[B]

Note. Oh, no, it was that. Yeah. Oh, sticky. I call them stick.

[A]

Ons. Oh, stick.

[B]

On. It's funny. And I'm looking at this, and then I said, I managed your assets for 18 years. What did I do wrong? Whatever. So.

[A]

He. Did he have an.

[B]

Answer? No. No, he was, you know, Don Fisher was not a warm, fuzzy.

[A]

Man. How long did that conversation last? 10.

[B]

Minutes? 3.

[A]

Minutes. 3 minutes. And you were out of the.

[B]

Office? No, I said, I want to see the board. So I went in to see the board. None of them looked at me again. I guess maybe they thought I was contagious. I don't know. And he came back. He says, well, we're gonna let you stay till we hire your.

[A]

Replacement. You stayed from May through.

[B]

September? September.

[A]

26Th. Why'd you.

[B]

Stay? Well, I wanted to finish my.

[A]

Job. Can I just go back for a.

[B]

Second? Yeah, go.

[A]

Ahead. You get this little card. You've been there 18 years. When you came in, what was the revenue of the.

[B]

Company? The revenue for 400.

[A]

Million. And what was it at 18 years.

[B]

Later? 15 billion. Okay, so there was no Old Navy either, which is Now, I think, 11 billion of this. Still 15.

[A]

Billion. I know you don't like the word turnaround, but you really like hockey, Stick their business.

[B]

Up. Well, yeah, I mean, I.

[A]

Did. Yeah. Okay, so on the heels of that, you know, bad year, you go in to see Don and he gives you a card with one line, basically letting you know, like, thank you so much. You know, here's the.

[B]

Door. No, I didn't get a thank.

[A]

You. No, no, thank you. Just gave you a.

[B]

Car. You're.

[A]

Right. So I guess what I want to know is how did that.

[B]

Feel? How did it feel? Well, it was. What.

[A]

The. Yeah.

[B]

Shitty. Well, it felt like.

[A]

Holy. Like a gut.

[B]

Punch. Don was not a warm, fuzzy guy. He's one guy. He gave you a million dollar raise. You still tell him to go himself. He wasn't gracious, he wasn't nice, and he was never really appreciative. You know, he Made billions of dollars. And so I was really pissed.

[A]

Internally. But you held it together, as we all do in those moments. I just want to.

[B]

Say. So I was on Charlie Rose probably a year after that, when Charlie Rose still had a show, whatever. And he said, how did it feel getting fired like that? I said, you know how it felt. It's their opinion. And they were wrong. You know, now I really feel that way about things. But politics and big companies. Few people didn't like me. Why? Because I knew who they were and they knew I.

[A]

Knew. That's my least favorite part of corporate.

[B]

Jobs.

[A]

Yep. So definitely, many years later, you still think about.

[B]

It. You know what I think about the mercenaries in this world? I think about private equity bankrupting J. Crew, bankrupting the company. I think about them not calling one member of the senior executive team when I left or when they hired a new CEO. That's what I remember about. I don't like big corporations unless there's a real person running.

[A]

Them. I interviewed Bobby Brown the other.

[B]

Day. I love.

[A]

Bobby. And she loves you. Of course. You all know each other. And she was telling the story about basically being.

[B]

Fired. When she was fired, I was her counsel in a way, because I went through it two or three years before her. In fact, I read in her book. I just called her Sunday. I said, bobby, your father was really handsome. And I said, also, the way they fired you was.

[A]

Awful. Is there a good way to fire.

[B]

Someone? Yes. I fired many people in my.

[A]

Life. What's the good.

[B]

Way? I sit down, it's not working out. I'm sorry. And I'm friendly with all them except one.

[A]

Guy. Because. What? Sometimes somebody just outgrows a job.

[B]

A lot of times.

[A]

Yeah. You leave there and then what makes you decide to go again with.

[B]

J. Crew? I was furious at how I was.

[A]

Treated.

[B]

Understandably. And Don said he made a mistake. He said, I made a mistake. I shouldn't have done what I did. I'm looking at this. And then he said, my family and I would like to back you in a new.

[A]

Company. Did you take him up on.

[B]

It? Oh, yeah, right. I wanted him as a partner again. Right. And it was bad for the company, bad for him, bad in the.

[A]

Community. You worked from May through September. How did you keep showing up there? Because people must have known I.

[B]

Wanted to make sure that I fixed it. And I knew I was going.

[A]

To. It was personal for you staying.

[B]

To show them I had an obligation. I didn't want to.

[A]

Leave. Then they just fired.

[B]

You. In fact, Don said to Me, once goes, I'm surprised you're working so.

[A]

Hard. Yeah. Why are you working so.

[B]

Hard? Because that's what I.

[A]

Do. Who you are. So you decide to go again. You go into J.

[B]

Crew. Well, I went In, I bought 10% of the company, and then I realized the inventory was that much worse, so they reimbursed me for, you know, the bad inventory. Four years later, we went public. I owned the name madewell. And there's nightmare stories with them as my.

[A]

Partners. You know, one of the things you did at J. Crew that you didn't do at Gap, you made Jenna Lyons a.

[B]

Star.

[A]

Yep. You actually. Right. Like at the Gap, at Old Navy, at Banana, it was never about one person. In thinking about that, like, would you do that.

[B]

Again? I couldn't have done it without her. Early days. What I do when I get to the Gap, to there, to. I interview the whole team very quickly, and I. It's kind of like Sophie's Choice in a way with me. Yes. No. Yes. No. No. Yes. And I met Jenna. She's there 20 years, and I said, she's the.

[A]

One. Now, are you still good friends with.

[B]

Her? Yeah. I mean, when I say good, you know, those were bad days in a company, and she was a very critical part of the team. To turn around the company to use your word and then to grow it. And, yeah, we're still friends.

[A]

So. Also not a good ending. At.

[B]

J. Crew, the private equity groups and the venture groups. I had the same thing happen at Outdoor Voices. I was chairman, but that's a whole other.

[A]

Story. No, we're going to talk about Outdoor.

[B]

Voices. Okay, good. So we're going to have a series here. By the way, before I got to Gap, I had a list of things, actually, when I was at Abraham and Strauss, I just made a list of all the Gap items that I thought America needed at a fair price. Now, I always admired Ralph personally. I find him whatever, but because he always kind of accused me of copying him. But he was inspiration because he nailed it, and he still does nail it. His clothes are nice. They're normal. He was always too expensive for me as a young person. You know, I went to Ann Taylor. Well, I was in my early 30s. But I loved his clothes. I got it all wholesale because my college roommates. A cousin was his.

[A]

Secretary. So the list is what you took to J.

[B]

Crew. Alex Mill. There's always a white space out there, and, you know, if you don't take the shot, you can't.

[A]

Score. But Alex Mills was started by.

[B]

Your Son, he started it 10 years.

[A]

Ago. 12 years ago. Really? I mean, you weren't.

[B]

Involved. You had nothing to do with.

[A]

It, and then you stepped.

[B]

In. Well, when I left J. Crew, I was. I sat at a venture capital office. That's how I got involved with. That was a nightmare with Outdoor.

[A]

Voices because Outdoor Voices was on fire. I remember my daughter being obsessed with their workout.

[B]

Clothes. Well, it was on fire. And the reason I, I invested in it, I became the chairman and of course I had to be the CEO. Ish. Because Tyler Haney, she didn't like me from the get go because I was doing what a chairman and a co should do. She didn't let me do my job and they didn't care. I hired some people. She fired them.

[A]

All. So then that sounds like a.

[B]

Mess. It was a mess. You know, you can't fix bad.

[A]

People. Okay, so let's go to Alex Mill because here, here's your son. Right. And by the way, having the antithesis of your growing up experience on.

[B]

Purpose.

[A]

Yeah. He starts the company. What do you think it is that people don't understand about Alex.

[B]

Mill? Well, now they understand it.

[A]

Better. But what is it? What is it they didn't get.

[B]

Before? First of all, when you have a couple of stores, tiny. We weren't known at all. You know, when I took over the big companies, they had a critical mass of people, lots of stores, and they were famous. And Alex Mill was a total unknown. And now, now we're in the middle of this. I mean, I'm.

[A]

So. And what's causing.

[B]

That? Five years of pain and all that. But what's the.

[A]

Startup. Much harder than turning around or however you want.

[B]

To. What causes it is. I didn't have the bank of Gap or J. Crew, you know, and I was funding it. I thought people would call and want to invest also. No one called. We're too small. We don't make any money. They said they had no interest. But what happened is the goods got better and better and.

[A]

Better. Okay, so I have a. I have a couple of questions. If you were starting out today, what advice would you have for somebody who's graduating from college? You've lived a rich life through a lot of journeys.

[B]

Here. Yeah, well, I, I tell them, hire your boss. I'd say you're going to make mistakes. Take a shot. If you instinct. You know, it's funny. I went to JC Penny to interview million years ago when I was finished with school. The, the HR guy touring us, it was in New York then. So the guy Says to the group of. Must have been 20 of us, you know, we passed the first interview. Whatever he said, you know, if you don't feel right about a place or it's not your kind of thing, you shouldn't be working there. I walked right out. So trust your instinct, trust your judgment. Pick the brains of people who know more than you do now. Speak to people who might, in fact, give you good advice. I spend every day speaking to strangers and like friends of people I know, the sons of.

[A]

This. You're always taking.

[B]

Input. I always. Well, I take every.

[A]

Meeting.

[B]

Yeah. And I always learn something. You never know. But, you know, I. I learn from every meeting because I, you know, I'm a.

[A]

Detective. I like D. You were always.

[B]

Curious. Always, always.

[A]

Curious. Okay, we're going to try rapid fire. This is going to be a test for you. I just want to say, because rapid fire may not be your thing, so. Okay, what's a mistake that taught you more than a.

[B]

Win? Oh, it's a series of.

[A]

Mistakes. You only get.

[B]

One. Be careful who you partner.

[A]

With. Okay. Like that one. Is there a habit or mindset you wish you'd adopted.

[B]

Earlier? You know, I'm pleased with where I am today, so just not trusting as much as I.

[A]

Trusted. If you think about the messiest moments in your career, and I love how many you've had, by the way, for you to be incredibly successful and had those many messes is amazing. What's the messiest moment on a scale of 1 to 10 that you've.

[B]

Had? The messiest was. Well, the shock was being fired with no notice. To be fired the way I was fired was the messiest and bad taste and bad.

[A]

Style. Is that a 10 on a scale of 1 to.

[B]

10? Oh, yeah. Oh, yeah. You don't do.

[A]

That. Last time you.

[B]

Cried. I don't.

[A]

Remember. Okay, that's fair. One career myth that you think is a waste of.

[B]

Time. Fancy degrees, fancy colleges, advice you'd.

[A]

Give to someone, and an MBA advice you'd give to someone who's having a confidence.

[B]

Crisis. Well, I have to know if I had confidence in them before I could give them.

[A]

Advice. If you were getting a performance review today, what advice would you give to someone as they head in to get that performance.

[B]

Review? I would say try not to be afraid. Say what you.

[A]

Think. You mentioned you use ChatGPT and you're all about.

[B]

Instinct. I just started, Chad. Just.

[A]

Started? You just started. Do you think that AI will kill.

[B]

Instinct? Well, I've had a big argument on that. I think will.

[A]

Definitely. What's the one thing you learned from Steve Jobs that surprised.

[B]

You? What I learned is no fear. He just didn't let anything stop him. I learned he was seductive. He's a great salesperson and a genius, and he was the smartest guy in the room. And we once had him over for a week. And my wife's pretty familiar with books and movies. He just intimidated the hell out of both of us. And it wasn't like he was bragging. He just knew every movie, every song, the books. Stunning. Very special human.

[A]

Being. What do you think of what's happening in the Gap.

[B]

Today? You think I can answer.

[A]

That? Yes, I do. You're.

[B]

Free. No. No. I. I could tell you, but not.

[A]

Publicly. Okay. All right, so let me ask you one final public.

[B]

Question. You can tell me the same with J. Crew. I cannot.

[A]

Answer. Then you can. No. Off the record. We'll have that conversation. You've made it to the end of the episode with Mickey Drexler. Mickey Drexler is an icon of the retail business. Anyone who's in retailing knows him because his impact has been outsized. But what I love about his story isn't just about his career. It's about the fact that he relies on his instinct and takes every meeting. Now, that is a lesson I think we can all take home. You never know what waits for you if you just take the meeting. Now, remember, if you enjoyed this episode, please like it, share it, and subscribe. And you can get us on all platforms from YouTube to Apple to Spotify or anywhere else. And remember, you can also follow us on Instagram and Tik.