Lessons from Steve Jobs, Gap & J.Crew

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Mickey Drexler: He lived up to being Steve Jobs. He was irreverent, critical. He was just smart and not easy, but I don’t know of any real bosses who are easy. If they’re easy, they’re not great bosses. The corporate world today, it’s like a friend’s club. Now, a CEO, they don’t want anyone who’s going to give them a hassle. Someone has got to tell people what they love, what they believe in.

Bob Safian: That’s Mickey Drexler, one of the most iconic CEOs of a generation. Mickey redefined the retail industry by radically remaking first The GAP and then J.Crew. He was also a 16-year board member at Apple working alongside Steve Jobs and helping to guide the creation of the Apple Store. I wanted to catch up with Mickey to get his assessment of the retail landscape today. As tariffs roll through and an uncertain economic environment presses the industry, Mickey is as feisty as ever, critiquing corporate boardrooms, poking at AI, and exhorting leaders to follow their gut or get out of the way. There’s no one who cuts through the noise quite like Mickey, so let’s get to it. 

[THEME MUSIC]

I’m Bob Safian. I’m here with Mickey Drexler, former CEO of J.Crew and of GAP, Inc. founder of Old Navy and Madewell, and now chair of clothing brand Alex Mill. Mickey, great to chat with you as always.

DREXLER: Nice to see you, Bob. Been a long time.

Copy LinkThe state of retail in 2025

SAFIAN: There are several topics I’m eager to ask you about. The challenges of leadership in 2025, lessons you’ve learned in building and operating business. You’ve had an extraordinary career. I want to start with the state of retail.

DREXLER: Okay.

SAFIAN: In many ways you helped create the modern playbook at GAP, at J.Crew. What’s your assessment of what the state of retail is right now?

DREXLER: Well, I’m a very tough critic since forever. I find retail now, it’s a whole different world. I think the merchant has gone out of the business a bit. A lot of people who lead the companies in my opinion are not true-born whatever merchants, and it’s about numbers, it’s about earnings, but at the end of the day, the most important issue in any business is the product, the goods. And I don’t think a lot of people really pay that much attention to the goods or in fact aren’t comfortable with the goods. And with investors, in my experience, it’s all about the earnings, all about the money, mercenary in terms of money, money, money.

SAFIAN: The irony of that is your approach has always been as much about getting the style as about the mechanics of the business, and yet that has led to more profits and a more profitable, more money, right?

DREXLER: Yeah.

SAFIAN: Like the quest for money doesn’t necessarily lead to that money?

DREXLER: Not at all. I think it’s true of every business. Now, I’m not an expert on all this stuff. I’m an observer of the world. And you don’t have to be an expert to be a customer or an observer of the world. I look at the cars out there. I used to love cars. I can’t tell the difference between the brands at this point. And if you don’t have the creativity, you then can’t move forward in the business because creative is inventive.

Copy LinkThe limitations of AI in retail

SAFIAN: I mean, you always loved walking through physical stores. I remember you taking me along. We went to a J.Crew and to a Madewell, and you were pointing out sort of why some displays worked and what things didn’t and how sometimes you even saw the product differently once it was out on the floor.

DREXLER: Yeah.

SAFIAN: Today, of course, so much happens online in these direct-to-consumer channels. Does that in-person experience still matter the same way? Can digital be just as effective?

DREXLER: It’s a really good question. The store is easy. I go in, it takes a minute to know if we look good or not. Online, I find, and I always complain about a lot of things, but I find that websites are never-ending and a customer doesn’t need that many choices. What do you love? What message do you want to give?

SAFIAN: And being a merchant is as much about trusting your gut. It’s like you’re a curator, really, right?

DREXLER: Beyond right. I had a big debate the other night. There were 10 of us at dinner and the subject of AI came up. One woman was on the board of AI and they were all my friends, but I get a little passionate and my wife says, “Calm down.” They said, “Well, it’s going to cost a lot of jobs. It’s going to do this, this and that.” I said, “I’m not really concerned with AI. I don’t think AI will be able to pick colors. I don’t think AI will know how to invest in merchandise. I don’t think AI is going to know how to negotiate with a factory owner worldwide.”

And then the fireworks started. And you know what I said? I gave up after a while, but I knew that none of them were creatives. And when you work with creatives like Steve Jobs, who was the best in the world, you’ve got to say to yourself, I love that idea. I love this. I love that. The instinct and gut for me drives the business. And I’ve been wrong. Who’s not wrong? You make mistakes, but that’s my feeling. My best friend is what I feel.

SAFIAN: You mentioned Steve Jobs. You worked with Steve as he grew Apple into a juggernaut. You were on the Apple Board for over a decade-

DREXLER: 16 years, yeah.

SAFIAN: What do you think Steve would think of today’s AI craze? Would he be into it?

DREXLER: I guess he’d have to be into it. Steve saw the future and he died way too young and the world misses Steve, but what he wanted to do, then his last thing and then he passed away, he wanted to do an electric car and he wanted to design it. And when he brought up the first Tesla as an example, the ugly two-seater, and I said, “Steve, that car is really ugly.” He looked at me with disdain, which I loved when he got mad or whatever, disagreed. He said, “It’s not about the design of the car.” He said, “Anyone could design a nice car. It’s about what’s inside the engine, et cetera.” He was just smart, really smart and not easy, but I don’t know of any real bosses who are easy. If they’re easy, they’re not great bosses. Demanding you have to do better and be as competitive as anyone in the world.

Copy LinkWhy Mickey Drexler believes “less is more”

SAFIAN: You started Alex Mill with your son. You told me, “I’ve learned more at Alex Mill than I’ve ever learned in all my jobs.” That’s a big statement. What have you learned and what makes it different?

DREXLER: What I learned is really, follow my gut. Really this year, I mean, I am going nuts on “less is more.” I like to pick on the cereal aisles. You can count 15 or 20 boxes of choice. The choices in America, in the world are well beyond what one needs. You need to follow your gut and you need to act quickly.

SAFIAN: When you talk about less being more, I mean in some ways it’s counter to the way the marketplace and culture is moving because we’re personalizing everything to everyone’s needs, and you can get anything you want anytime in any way. And a lot of people think, oh, that’s great. That’s a great thing about the modern world. And you, you’re shaking your head no.

DREXLER: No, because someone has got to tell people what they love, what they believe in. You don’t need 50 brands of a TV. Do the best of the breed, market it and sell it, and make sure it’s high quality, which I think has left the world to a degree also. What separates great product from all other copycats is quality. I’m proud to be a micromanager. It’s not micromanaging, it’s setting a tone and teaching people. To me it’s simple. We say, “You buy one and you own it forever. You don’t need more clothes. You need the right clothes.” I don’t know what you’re wearing underneath. Is that a sweater?

SAFIAN: It’s just a T-shirt.

DREXLER: Yeah. T-shirts. T-shirts last forever. And a classic style that you can wear forever.

Copy LinkHow the leadership landscape has changed

SAFIAN: I want to broaden out a bit to the leadership landscape right now for CEOs and others in business. CEO turnover stats are quite high, maybe higher than ever. Has the role of a CEO gotten harder and riskier in 2025?

DREXLER: Well, I don’t know. I think, well, I have an opinion about CEOs and boards of directors. Every one of your best friends can qualify as an independent director. When I was on GAP’s board, I didn’t have any vote except when I invited Steve Jobs on the board, we made a deal. I wouldn’t go on his board, I was stupid or whatever. After a year, he said to me, I’ll never forget this, “You go on my board, I’m joining The GAP board.” And I said, “We have a deal.” And he lived up to be Steve Jobs. 

He was irreverent, critical. The corporate world today is, I think it’s an old, it’s like a friend’s club. Now, a CEO, and I understand they don’t want anyone who’s going to give them a hassle. There’s a company Outdoor Voices I was the chairman of for a year between J.Crew and Alex Mill, and I said, “This would be a Lululemon competitor.” But the board and I was saying, “You need to make a management change.” They didn’t care. Couldn’t care less. Really, someone needs to have a course on no bullshit.

SAFIAN: No bull, indeed. Mickey doesn’t mince his words. Corporate boards aren’t courageous. Retail is too mercenary, and AI isn’t all that in part because it can’t pick colors. There is a reason Mickey and Steve Jobs got along. They each did things their own way. So what does Mickey think about American Eagle’s Sydney Sweeney campaign? Why is he an advocate for in-office work? And which of his previous companies does he refer to as schlock heaven? We’ll talk about that and more after the break. Stay with us.

[AD BREAK]

Before the break, retail icon, Mickey Drexler, gave us his unvarnished view of the retail industry. Now he talks about American Eagle’s Sydney Sweeney campaign and what he calls “brand right,” his old school hack at J.Crew for combating bureaucracy, and why he’s skeptical about retail manufacturing coming back to the US. Let’s jump back.

Copy LinkMickey Drexler on Sydney Sweeney’s American Eagle ad

SAFIAN: In conversations that I’ve had with CEOs, mostly off the record, they talk about worrying about how something could inadvertently spark a social media firestorm or they could inadvertently do something and become a target of the government, that they just feel like they can’t exercise their creativity or follow their gut necessarily the same way.

DREXLER: If they were creative and had a gut, one of the most important jobs we all have is judgment, knowing what’s on brand, off brand. There was this thing with Sydney Sweeney lately. Say something.

SAFIAN: Yeah, I was going to ask you about that. What did he think about that American Eagle ad campaign and the back and forth about it?

DREXLER: When I first saw it, I said, “Gee, this must cost a fortune because she’s a hot commodity.” And then they talked about the G-E-N-E-S versus J-E… I thought that they should have, and they did not talk to the issue. Went silent. And that created more news. But if I were, “Sorry, I screwed up. All right? We learned the lesson.” And when you screw up, you learn lessons.

SAFIAN: It seems so tricky now for brands to define themselves without sparking controversy. I mean, you want as big a pool of customers as possible, right? Or is controversy okay? Consumers want to see their favorite brands connected to things.

DREXLER: I talked about that as being, there’s a very important job I have and we have. Brand right. And I say of something, “It’s off brand.” And it starts there. It’s not difficult to be right with your brand if in fact you have the judgment, the beer thing, Budweiser, whatever. How do you allow that to –

I’ll tell you how it happens there. I’m sure the CEO had no clue what was going on. The big challenge really is you are running a country when you run those big companies. How far removed is the CEO from the selling floor, from the factory floor? I don’t think it’s good. How do you perfect a business without loving the products and the brand and caring?

Copy LinkWhy Mickey installed an office-wide loudspeaker system at J.Crew

SAFIAN: Another big leadership challenge these days is leading a workforce and balancing things like in-office versus remote work. I assume that you are an in-office champion.

DREXLER: You’re right. I’m looking at things every day, goods. You’re also providing leadership. You’re providing cultural learnings. You are giving feedback. As a boss, yeah, I am against it. We have a policy here. If you don’t come in, you’re not employed.

SAFIAN: I remember at J.Crew you used this office-wide loudspeaker to share messages with the team. Who needs email or Slack, right?

DREXLER: Right.

SAFIAN: Now that was a leadership decision that certainly made the place feel more open and transparent. Was that the goal? How calculated were you about that? Or was that, again, just gut?

DREXLER: Well, I’ll tell you the reason I did it. So I get there. They had an enclosed office as the two prior CEOs had. I’m sitting in the office, I’m bored. And every time I call someone, I get a voicemail. And this company was going like this, literally bankrupt-ish. After two or three days, I’m thinking no one calls back. And I love urgency. It’s part of everyone’s job description. So I said, “Put in a loudspeaker.” There was no thinking. How do I get to people? We had three floors. I don’t know a thousand people. Who knows how many? I didn’t really know most of them, but my voice met them. And then I use them as resources. I’d ask if there’s a shopping mall in Nebraska, “Who lives near the shopping mall? What’s it like? I have open office hours. Come in, if we had some VIP visiting, if you want to say hello to whoever.” But it made it very small because I was very familiar, and I was allergic to the bureaucrats.

SAFIAN: What was the most important cultural shift you had to lead in an organization? Was that at J.Crew?

DREXLER: GAP was. I fly out to San Francisco, I stay in a hotel, I take a taxi to San Bruno. We had two buildings, parking lot overlooking the airport, the cemetery and highway to AD. The company was schlock heaven. Everything was on sale. There was no feeling of quality. It was a miserable two years. And the company was going like this, and I had to get rid of horrible inventory. I was 39 years old. And then the chairman, Don, calls me one Sunday or he says, “What are you taking all these markdowns for? We’re going to have a horrible quarter.” And I got mad. I mean, I can’t control. And I said, “If you don’t turn the goods into cash, we’re going to have even a worse quarter because we’re not going to have money to buy good goods.” And the culture at GAP, oh my God. You have to change their thinking. I was difficult. You have to be, especially on a turnaround.

Copy LinkTrump tariffs and the future of retail

SAFIAN: This era that we’re in seems so chaotic and uncertain. Are there specific stories or situations from your career, from your life that you find yourself reflecting on as we move through this uncertain time?

DREXLER: I’ve never ever been in this kind of environment. This tariff. I mean, we’re flying blind. You can plan the business. The tariffs have cost us, have damaged our cash flow. It’s going to put small companies out of business, and it’s also going to hurt a lot of big companies. China is actually the headquarters for all American factories.

SAFIAN: And the goal of the administration to bring manufacturing back to the U.S., certainly in the retail areas that you’re dealing with, you just think it’s just not realistic.

DREXLER: There’s no factories, there’s no trained sewers. LA makes great jeans, but no, we have to raise prices. It’s really difficult, and it’s the biggest worry I have.

SAFIAN: When you were at GAP and at J.Crew, how much did you respond to the external economy in operating and adjusting your strategy, in terms of what was in your control and what you have to be reactive to?

DREXLER: Well, what I was reactive to always is how it affected the team. You are there to calm people, to let them know that the future will be okay, but you don’t change your business standards. You always go through a bad year. That’s a given. You might buy less inventory, but you didn’t do much. I wasn’t different. You have to get more supportive. And I think people need to, I know I always needed to relate to someone I worked with, and a lot of people don’t do that.

SAFIAN: You still, clearly, you still have passion for this topic and this area. And at the same time though, you’re never satisfied.

DREXLER: You are right. People say, “Why are you still working?” I say, “It’s a sport. What else would I do? It drives me.” And I love the creative, I love the people. I used to ski, used to play tennis. This is my sport and I’m really enjoying it.

SAFIAN: Well, Mickey, this has been great. Thank you so much for doing it.

DREXLER: You’re very welcome.

SAFIAN: Talking with Mickey is always a bit of a roller coaster. I’m never quite sure where he’s leading me, but there are plenty of thrills along the way. At core, he keeps things pretty simple. Work hard, be passionate, trust your gut, and keep learning. Those principles are as modern as ever. If there’s one insight I keep coming back to, it’s his edict at Alex Mill to provide fewer customer options, fewer choices. It sounds like sacrilege today when we all want exactly what we want now, immediately. But the ethos of “less is more” is precisely what sets the best businesses apart to focus on what they do well and become well-known for it.

Something people often forget about Steve Jobs, when he returned to Apple as CEO the second time after being forced out of the company he created, one of his key first moves was to dramatically cut back on the number of products that Apple offered. He focused on a few things that were exceptional, and it helped define an Apple ecosystem that continues to engender loyalty to this day. And as Mickey says, “You can’t focus on a few things without trusting your gut.” So take a deep breath and try to remind yourself, what makes your business different and special, what matters most to you. That’s probably where your future should be pointed. I’m Bob Safian. Thanks for listening.