I don't know why but when I say this guy's name I got to add an F bomb in the middle of it. I know you've been doing it every time. Mickey [ __ ] Drexler. This guy, 18 years a CEO of the Gap, took it from 400 million in revenue to 14 billion. He creates Old Navy, he creates Madewell, he develops... he basically takes J.Crew private. This guy is the Godfather of retail. And when you think about iconic CEOs in any industry, Mickey Drexler, Mickey [ __ ] Drexler's name always comes up. And he's full of stories and huts but on audacity, and he just goes into these incredible stories and anecdotes about working with Steve Jobs. I mean, he was on the board of Apple for like 10 or 15 years.
Well, they call him the Merchant Prince for a reason. He is. And what really struck me about Mickey is his sense of urgency. Right? He almost thinks it's riskier to not make a decision than to make the wrong decision.
Well, he said he has this very simple heuristic for how he gauges when he's interviewing someone, whether or not he's going to hire them or not. When you hear the heuristic, it's simple and brilliant. And I think I'm going to use that from now on. But he goes into details of how he built the Gap, he talks about how he created Old Navy, he talks about where the name came from, he talks about why Steve Jobs and he developed this relationship and what Steve Jobs taught him. It's an unbelievable interview. And I think Mickey Drexler epitomizes everything there is about big shot that we love so very much.
100%. You know, he was really into his gut. What's his gut telling him? But there's a method to it, right? As the interview unfolds, you start to see how he thinks about when to use his gut and when to get enough information and how to process it. I thought he gave us some really important tips he does.
Then he tells this story of 18 years into being the CEO of the Gap, he gets this call late at night from Steve Jobs that will totally change his life forever. Yeah, and he explains exactly what happens on that phone call. Ladies and gentlemen, Mickey [ __ ] Drexler.
Started from the bottom, now the whole team here. Start from the bottom, now we here. Start from the bottom, now my team start bottom. Now start bottom the team... Oh [ __ ], no, not that. He... Oh no, never mind. You're good.
It was an emergency. What's the emergency? Now it's gone. It was a chip... of a potato chip. So thank you, thank you, and sorry we had a chip emergency. But I'm looking... I need the yellow get on me. All right, I'm going to win an Emmy for this one.
When people mention Mickey Drexler, they think of a couple things. They think about you running the Gap for 18 years, taking it from 400 million in sales to 14 billion. They think about you founding Old Navy. They think about you taking J.Crew private, founding Madewell, founding Alex Mill.
Nope, my son started. Sorry. Helping to build Alex Mill with your son. My son is Alex.
I figured as much. But I actually want to go back. I want to go back to the one-bedroom apartment in the Bronx and I want to start there, okay? And I want to talk about what it was like growing up there.
Okay. Well, I didn't know what other people... how other people lived. That didn't bother me much. Even if I slept in the living room or who knew, because in the Bronx we were all on equal footing in that regard. And I never knew anyone who was a big shot—which, no pun intended—or a perceived big shot. The worst thing about that was my father growing up, because he didn't meet my job description of what I thought a father should be.
What do you think a father should be?
Nice. Affectionate. Not talking to me... I think I told you to tell the other, maybe I didn't. Anyway. What should be encouraging, not angry all the time, and caring. And he was none of those things. He couldn't check the box on any of them. My mom had cancer the year I was born, and he wasn't nice to her. And he just wasn't a nice man. And my validation was my seven cousins—Jewish cousins who lived down the street. I didn't know they all disliked him. My mother's sisters, my aunts, disliked him. And someone—I don't know, someone asked me the other day, did he have any friends? And he really didn't. And all the big shots in his life were people who he bought goods from—Spoober and Shapiro—and I grew up thinking... well, I didn't want to face that he was, in fact, what he was, because you want your dad to be this. You put him on a pedestal.
Yeah, I did. But I kind of started to know. But I kind of wished I had a rich dad. Why? I'm glad I didn't, because here we are. And it's different now. You're the rich dad.
I am, but I never think of that, okay? Because the Bronx gives you a certain value system.
And what is that value? Well, for me, it's identifying with people that have nuts. And I don't mean 'have nuts' just financially. You know, they work hard, they do whatever. And I say, I get away from the woman who cleans the building, and she knows—she does every day. And like this morning on the way here, the elevator opens, she gives me a big wave and a smile. And that makes my day. Because I never liked big shots. Because my father wanted to be one, and I confirmed that he wasn't when I took the payroll—because I used to work in the shipping room to the bank when I was 16. I'll never forget, I tucked into the alcove out the freight door. I went through every envelope, and I saw his salary.
So just to set the stage here, so you were working at the same company your father was?
He used to... The good thing he did was he made me work. Not nicely or with any charm, but 'get out of bed, you're sleeping late' and whatever. So I went to work in the shipping room of this company.
What was he? He didn't own the company? He was an employee there?
So wait a second. So you were in the shipping room, he had a boss, you're working there, and you were able to see all the pay stubs?
No, they asked me to take it to the bank. So you had the pay stubs in my hand and obviously your father's pay stub is there. I looked at all of them.
You looked. And then what did you see when you looked at your father's?
I saw that he was one of the lowest paid people in the shipping room and in general. And he always acted like he was, because he bought expensive clothes and whatever. And it turned out he actually wasn't making very much money. But he acted to the family, the aunts and the like, that he was a big shot. And, you know, he was Uncle Charlie. They didn't like him much at all.
What did you see when you saw that your dad, who acted like a bit of a big shot to family and other people, how did you feel when you found out that he was the lowest paid person?
I was devastated. Because it broke... it eliminated the fantasy I kept with about him.
When you realized you didn't want to be a big shot, because you said 'I didn't want to be like him'?
Oh, I... well, part of it. Because anyone who had those days... it might have been a Cadillac convertible or a doctor, it was a big shot for him. Or CPAs, they were professionals. And he was just not a nice... he had no emotional measurement whatsoever. No matter how bad things might be with other people, whatever I did well, I gave trying to tell him, because he never really was nice as I was growing and doing better.
I always have a tell. There's one great... it's not a great story, it's what I lived with. There's a really good article. When I was early days, I started to get some really nice articles. This is when I was at the Gap, yeah. And it was a really good article, happened to be in Vogue, but it wasn't a fashion-y article. And the writer was great—it always matters who the writer is. And I said, 'Hi, by the way, there's a really good article in Vogue.' Nastily, he says, 'You've seen them one, you've seen them all.' Wow. And here you thought, look, you're at the Gap, they're writing a great article about you, it's in Vogue, a big magazine, you want your dad to be proud of you. And he says, 'Well, you've seen them one, you see them all.' Like that. He says, 'You've seen one...' and you know something like... were there ever any moments where you remember him fondly, where you got something out of the relationship?
Except he worked hard, maybe 'get out of bed, go work.' And part of what you get in hindsight is it develops an escape drive. You want to get out of your environment. And I think I said the other day, you live in your imagination, you live in a fantasy. You want to escape.
What was your fantasy at that time? Once you realized... well, you know... it's a good question.
Just not being there. Oh, having siblings. My mother died when I was young, couldn't have them. And luckily because... and having a bedroom. And then beyond that, not living... it was okay where I lived, but once I met a friend who lived in Riverdale, that's the fancy part of the Bronx, he had a three-bedroom apartment, a maid. And I'm thinking, 'Oh my God, this is a good life.' It was like another world. Like 'I want this.' Well, that was certainly a stepping stone to other people. Or if I went away to sleepaway camp in bungalow colonies for a number of years, and if someone had a Cadillac, wow. Because I was playing off my dad's values in a way. And you know when you live with someone like that, bitter, angry, and all that stuff, and not nice to my mother, and she was sick when I was growing up... And so I realized as I got older that first of all, I wanted to be successful. I never said 'I want to be...' I never had a... the first day at Bloomingdale's on a training program, they went around, 'What do you want to do?' I don't know what I said. Some one guy says, 'I want to be a vice president of this joint.' I look at this schmuck. He was a lucky sperm cell.
By the way, just to define 'lucky sperm cell,' meaning that his parents were somebody?
Yeah. And it was a low bar to be lucky in my definition. But, you know, I never thought about being the way I am. I mean, whatever success is called, but I never went there because it was one step at a time. I guess I always had a good sense of decision or instinct and gut. And I always say my best friend: gut instinct. And if I think it, I accept it. And then if I'm wrong, I'm wrong. I always had that gut about all my bosses. I think I mentioned this one, Katie Murphy. She adopted me. She was a fashion director—this is at Bloomingdale's. At Bloomingdale's, I was very lucky. I was on a fast track.
And that was really your first or one of your first jobs?
That was my first full-time job.
Wait, I mean, he says here's this guy wants to be vice president, and you say, 'Look at this schmuck.' Why? Why was he a schmuck?
Because I'm a human being. It's a schmuck thing to say. If we go off the record, I'll tell you another story.
We're on the record, brother.
I don't... yeah, no. When you start to meet people, and I try to give it to young people—don't have the confidence. I was in my late 20s, early 30s. You have a radar to immediately who you like or don't like. And then I always tell people, you know, sometimes I've repeated this like yesterday, but I always tell people when they say, 'Oh, he's a terrific guy'—and I know a lot of terrific guys because everyone's nice to me now. I remember those that weren't. Not that I see them—be a fly on the wall, watch how they treat family help, whoever. And that's who's nice.
You once told me a story that I love. I repeated it to David this morning in preparation, which is that when you were interviewing somebody, you would ask your receptionist how they treated her. Like, when the interview came in, how did they treat you? As opposed to obviously they're going to be nice to you, you're Mickey Drexler. Like, they're going to be, of course, nice to you. But how do they treat the receptionist? And the other thing you mentioned to me that I led David with, which I love, is how quickly do they walk? And I think that 'how quickly do they walk' is a fantastic proxy for someone that just wants to get [ __ ] done.
Yep. I love that. Tell you what, no, it just... you know, it's kind of... I learn and then I look, and I have these ideas. I say, 'This is what I do.' I also another thing: I like people who are nervous when they interview with me. Because it's a natural thing. You got to be a little nervous. I always can tell—the neck turns a little red. That was my sign. And I like them. And when they come in, I hate know-it-alls. Today, I... oh, they... we, my friend Stephanie Greenfield and I, we called them—this is years ago, she started coaching. She's still a good friend and advisor. We say, 'Oh, they're an authority.' That was the nickname for the 'authorities in their own mind,' right? Trying to impress you.
Where did you get the idea to treat everyone with respect regardless of their station?
You know, it's a really good question. I developed... I was never treated... I would say I was treated okay, but I never knew I'd be becoming what I'd become. And I always, always wished I would get a little 'hello, nice' from... like in Bloomingdale's or at my summer jobs. You never wanted the big shots. No, I always use that word. You never wanted... you wanted the big shots to give you a smile or 'how are you?' Be warm. In fact, that was the entry level for me of liking people. And I'll never forget the chairman of Bloomingdale's, Harold Krensky, was a lovely guy. I have no idea if he did his job well, but he was the chairman and nice. His successor, Harvard Business School... I hope there's no one listening... oh, might be big shots from Harvard. Anyway, you know, the people carry their credentials on their sleeve like a uniform. 'You know, Harvard...' Yeah, it's like when I lived in California, 'Stanford' first... the second sentence. And it doesn't mean anything to me at all now. Then I kind of was longing for, like, 'Oh my God,' but now it's no more.
When you were at Bloomingdale's, you weren't a big boss there. You were in the training program.
Well, I never was... see, the reality is, first of all, I say just pick a good boss. Training programs, you learn nothing. Okay, someone stands up there... well, school I learned nothing too. They stand up there and they talk. And working is training. Life is training. So I never actually was in it, because they... I was very lucky. They, you know, life is about these incidences that happen. My first day, I was in house. I didn't know what the hell I was doing, a pot of pan. And Tim Morgan, I think he was a cool guy, but he was nice. And then the next day, they assigned me to be a buyer of a department because Barbara was out on maternity leave. So I became the boss. And a lot of bosses pay no attention, just don't. And that was most of the world. They left me alone. Stan Stern was my boss, and he was a terrific guy. Very supportive, nice. He was a good person. Just passed away a couple of years ago. Stan was kind. But I went out to the market on my own. I went to all the showrooms and I bought goods. I reordered. My best seller was an Arthur Bell elephant pant, and it was only one store even though Bloomingdale's had six stores. And I just... I didn't think about it. There wasn't data involved. You just saw it and you liked it.
How many? No, data is always important. How many do I own? How many did I sell?
And I used to... my nickname was 'Stubs.' 'Stubs.' I'll tell you why. Because in those days, they had a spindle, you know, with the price tags on it. So they tore them off, they put them on the spindle, and I'd stand at the register even every day and start looking through the stubs. And it gives you a clue. It's a tell. So as the buyer, you want to know, is your product selling that minute, that minute, that minute? No one teaches you this, right? I mean, you get this break, you're there, and you intuitively feel a sense of confidence in what to do. Where is it? Like, you know, I have no clue. But I've always been a bit obsessive about phone calls and all that. And I say, 'Kelsey, tell them I'm going to call in three hours or whatever.' And I have a rule in the company—most people don't listen: three-hour returns on every email. I really want an hour. I want it immediately. And people... you know, and then this morning, I said, 'Why don't you tell me about this issue?' I learned it from a competitor. They said, 'Well, we've been talking about it.' I don't care what you talk about. I said, 'I'm here to teach.' That's my mentor and mensch, my two favorite words. And I heard from a competitor—she was a friend of mine. She ran a really nice company. And we have a nice... she has... well, her two biggest—I guess it goes through Shopify—is affiliates and influencers. So I walked out of the small office. I said, 'Do we know the percent of our business by affiliates and influencers?' The answer is, 'We get it weekly.' And I'm saying, 'Oh really? What do you do with it? What do you do with a bestseller? What do you do if you see anything trending in your world? You go after it. It's a tell.' If you don't have the detective sense, then I called... well, she's the new president. I love Ally. I said, 'Ally, I don't care what you did, I care what you're looking at down the road, not rearview mirror. So what happened last week? What do you do with the information?' And then I called the guy who's in charge, and I mean because he's not in the office today. And I said, 'Kyle, what do you do with this?' 'Oh, we...' 'I don't ever want to hear you talked about it.' And I said to Ally, 'Ally, you look down the road to build something. You look at where it's going.' And it's like a selling report. You know, it's a religion. The selling report: how many do you sell, how many do you own? And then I'm just going to give a story. So this morning, I'm standing out... you know, I schmooze a lot. So I ran into a woman who knew me—I don't remember—but she works in the building. I sometimes recruit elevator people. I once recruited her to go to the office. I love the coat she was wearing. So she says hi. You say recruit? You met someone in the elevator? And there's a few fashion companies in our building. If I see a cool, friendly person—because they don't... you know, I don't like fusers—got to get a... so in this case, she says... I said, 'I'm sorry, I don't...' She goes, 'You remember, I work at so-and-so. I was wearing a coat, you brought me into the office and you gave me a VIP card.' She was with a sister. I'm schmoozing with her. So the designer comes in from the coffee shop next door. She's wearing an amazing-looking sweater. I loved it. I knew it was ours. And I said to Alice, and the two women said 'Love that.' I said, 'I love that sweater. Do we still have it? Do we own it?' Here's her answer, and she's terrific, but she says, 'No, because it didn't sell well.' I said, 'How do you know?' They told me? You know, you could figure out if you hide a sweater or you buy 10. They'll look at three months selling. I look at... I learned by myself at Bloomingdale's: how many do we sell in February each day? The first week on a T-shirt ended up being the biggest unit-bit. It's a long story. 30,000 biggest unit by... and then the chairman comes and says, 'Is that the right amount?' He's looking down at me. You know, went to City College or whatever. I could be a little nasty. I don't want to sound that way. I just have a high standard personally. So you won't... you guys will, but wait. The sweater didn't sell. It didn't. But I don't take anything at face value. What's her definition of 'didn't sell'? And I did say, I said, 'That's a great sweater.' So she says, 'We have something just like it, it's even better.' I busted her on that when we got to the office. And then, you know, when I got up to the office, I said, 'Alice, let's talk. Show me the better sweater.' I guess they get a little nervous maybe because I'm intense, but they know who I am. A lot of them... whatever. Anyway, went through it and I said, 'I want that sweater repeated.' She showed me what was similar, not at all. And then I looked at it and I say to myself, 'First look, that's what I think. Old Navy or whatever. I don't care. We're going to do that sweater. And if I'm wrong, I'm wrong. But this one, I'm right.'
Is that the same type of philosophy you brought to the Gap? That sort of this gut instinct? I mean, because it's one thing to get lucky on one particular SKU or one particular product, but to get lucky over an 18-year period is quite abnormal. Do you credit your success running the Gap, making it a cultural icon, to your instinct?
No... well, yeah, well I credit anything... just you have to have an instinct. All of you doing what you do, or you have to trust it. And I always say—and I didn't do this when I was young as I didn't have the competence—if you're thinking it, it is. I knew when I was in grade school the bad teachers were what you think about. But this is very counterintuitive. I mean, the buzzword today is data-driven, right? Or better yet, data-informed. But here you are, you don't even care why it didn't sell. You're like, 'No, this is going to work. Let's repeat it.'
I don't... but what I look at is the data is critical. The only subject I excelled in was math. And I also have my most favorite grade school teacher, which goes hand in hand with wanting to learn, because the teachers... you know, chemistry, Miss Frank, what am I memorizing the chemistry codes for, the table of elements? Or calculus, just you know, I got by. But it's just to me, it's all logic trying to get a conclusion. And I do care. I care if they said they owned 400 and it was bad colors, yeah, then I'd say that's why it didn't sell. Do it anyway. Yesterday I saw a sweater. It was an email. And I looked at the sweater and I said in the email, 'Is this sweater in our language kind of going to be a key style we're going to sell a lot of?' So I get into the office. I've one senior, three people do merchandising—know the company's hundreds, did it. I said, 'Let me see the selling on that.' Boom. Two stripes, one solid. Stripes were by far better looking. The solid was a bad color in my opinion, but the customer validated that. So I said, 'What are you doing about this?' She says, 'Well, I haven't made a decision yet.' This is four weeks it's been around. I said, 'Let me hear the selling.' It blew out in four weeks. And then I get emotional. I don't know if it's called upset, but I said... and then I get her boss and I say, 'What's with the you haven't made a decision on a bestseller?' Second day, third day, it's a... but by the way, if it was a brand new sweater, it was a crewneck sweater in a boring color. Solids and stripes are major now. Funny story with stripes, you know.
But is that a lack of confidence? I mean, it's clearly a bestseller.
It's a lack of urgency. Yeah. Maybe not being driven. I mean, I... today, every day I have something where I want... I said, 'You know, I'm here to teach and have this as a long-term viable business.' Because in my stage of life, you got to do that. My son started it. I'd like him to be... you know, have a... this is Alex—we're talking Alex Mill. And I recruited people who used to work... they wanted to get out of the old company anyway, that was J.Crew. But that's a responsibility I have. You know, the 'independent parent' thing on boards is all [ __ ]. You know, they have to check the box of independent parent: who's your backup? Who's this?... Succession planning they call it. Exactly. Yeah. And then they have the consultant come in. 'Who's your... the guy with the badge?' Yeah. In other words, I make a lot of mistakes on people, but you have to act quickly. But that's why I want to help. That's right. And they leave out this important subject, like that sweater. So when I get back—this just happened—I'm going to look at the selling. It doesn't matter. But I'm... the two stripes that came... and also another... I'm sure they blew out. If you have two good colors out of six, I say every color is a panel because they lump everything together. But I'm always looking like I'm a detective, DNA. And you have to be. I love detective shows. Columbo. When I was... you know, he was a great detective. He always left the room saying, 'Um, by the way, one more thing.' That was always the question. It was. And I loved his style.
But I mean, at a place like the Gap or in fashion history, or the 'schmata' business as you and I like to call it, you can use that instinct. You were on the board of Apple for how long?
Okay. You were on the board of Apple, by far the most valuable company on the planet today. But Steve Jobs is probably the greatest product visionary I know. Steve Jobs is a very close friend of yours. We'll talk about Steve in just a bit. But talk a bit about how it was different, you running the Gap versus being on the board of Apple for 16 years. Because that to me seems like real precision. I mean, there's some gut instinct, of course. Steve obviously famously had this incredible gut instinct for design. But how were those different for you?
It was hugely different. First of all, I am to this day—I don't know... I couldn't get into the building. Kelsey gave me... yeah, you're not a great... technology is not your thing. Kelsey gave me this email: 'Just press this and I know what to do.' Why you and friends... God, there was... good. I used to have a BlackBerry in the meetings. This is Steve.
