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Wonder. I'm David Brown, and this is Business Wars. When you think of the Gap, what comes to mind? You picture the iconic navy blue drawstring shopping bags. Or maybe Sharon Stone wearing a Gap sweater on the red carpet. Or perhaps you're calling up the scent of their dream perfume. For many elder millennials, memories of the Gap call up fond nostalgic feelings. But for the teens coming of age in the mid-2000s, well, the gap was just another store at the mall, often passed over for the fast fashion trailblazers like Forever 21 or H& M. And for Gen Z. The company's hoping that this new generation thinks of it as the brand behind the viral ads with the hottest celebrities. The most recent that Better in denim dance ad from this past August that got nearly 400 million views in its first few days. Everyone online was trying to learn the choreography, which was set to milkshake by khalees.
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We go 5, 6, 7, 8, 1.
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And 2 and 3 and roll down middle and tap, tap. Gap even posted its own dance tutorial with instructions from the original choreographer, and that, too, blew up.
C
Hey, guys, it's Robbie Blue, and I'm going to teach you my choreo to milkshake. Here we go.
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The company's CEO, Richard Dixon, is behind the push to regain cultural relevance. Dixon joined the company in 2023, and so far, his approach seems to be working. Dixon is the mastermind behind the revival of the Barbie brand, and the question on everyone's minds is whether he can lead Gap to a similar comeback. Joining us to talk about that, Jordan Holman, a retail reporter at the New York Times. She's helping us analyze whether Gap can keep this energy going and return it to the powerhouse it once was. Later, we're diving deeper into Gap Incorporated's biggest moneymaker. Old Navy retail executive Aubrey Avery Jr. Was part of the team that built the brand back in the 1990s. During his tenure, Old Navy became the first retailer to hit $1 billion in sales in its first four years. He also expanded the Gap's footprint, bringing shops into underserved communities and new markets. Aubrey worked with former Gap CEO Mickey Drexler and Old Navy's original founders to turn the store into a household name. And today, he's walking down memory lane with us and sharing the strategies that shape Gap Inc's golden age. Stay with us. When planning for your future, you want someone with a history of keeping their word year after year. For nearly 160 years, Pacific Life has been a trusted name in the industry. But that isn't just a number. It's experience that matters. It's 160 years of promises held, helping generations retire with confidence, protect their loved ones, and plan for whatever comes next. Whether you're looking for life insurance, employee benefits, or retirement income solutions, when your future is on the line, you want history on your side. And believe me, Pacific Life has been there, always there, through changing times, always focused on your needs, ready to secure your tomorrow. Ask a financial professional how Pacific Life can help you feel prepared for what's next. Pacific Life Insurance Company, Omaha, Nebraska. And in New York, Pacific Life and Annuity, Phoenix, Arizona. Because with Pacific Life, you're not just planning for the future. You're partnering with trusted experience. Let's say hypothetically, or maybe not so much. I'm developing a new podcast that needs an assistant producer, someone who knows how to brainstorm subjects to talk about, find guests to bring in. That's a tall order. In other words, it's a job for Indeed. Sponsored Jobs. Spend more time interviewing candidates who check all your boxes and, you know, listeners of this show will get a $75 sponsored job credit to help you get your job premium status it deserves@inn Indeed.com businesswars just go to indeed.com businesswars right now and support our show by saying you heard about Indeed on this podcast. Indeed.combusinesswars terms and conditions apply. Hiring do it the Right Way with Indeed. Jordan Holman. Welcome back to Business Wars.
C
Thanks for having me.
A
Have you fallen into the Gap? Were you one of those Gap people? When you go to the, you know, to the mall, were you hitting up the Gap?
C
You know, I did go to the Gap, but you would probably see me more often in Old Navy.
B
Oh, really?
A
Okay.
C
Remember, they're like $1 flip flops and their, you know, American T shirts. Like, that's really where I was shopping at. But of course, I would have to walk by the Gap to go there.
A
Okay, I gotta ask, because I've never been a fan of the Gap. It's not, not that there's anything that I don't like about the Gap. It's just that it never really has had anything that I really particularly was never any real reason to go to the Gap. Old Navy. You're talking about some casual basics, right? Things that you gotta have in your wardrobe. What's your sense of why someone would go to the Gap?
C
Well, I think the Gap for the longest time did kind of lean into the basics. Like, here's your blue jeans. Here's your, like, you know, it could Be a white T shirt or a cream T shirt. That's what I think of for the Gap, but then also khakis. But I think you're hitting on a tough place that Gap has been in. A lot of places can sell you those clothes, and that is a struggle. So it's like, why go to the Gap when you could go. Even Old Navy sells that as well.
A
That's one of the things that always seemed kind of confusing to me, because you're right, they have been, at least in their past, a go to for blue jeans and T shirts. But it's not the kind of place that I think about, you know, when I'm. When I need that sort of thing. I am thinking about Old Navy, and I'm wondering what happened there. What do you think?
C
Right. So historically, if we really go back, like, yes, you could always buy your blue jeans from somewhere else. You could always get that cream shirt from somewhere else. But what Gap did, did was they hit on culture, they hit on music and photography. And so you weren't necessarily going to the Gap because they had the most amazing quality jeans. But it was cool and it was ever present and it was at every mall. And it felt like a stop that you had to hit along your, like, shopping journey. And what fell off was that cultural impact. They fell out of the conversation. So I think that's the biggest thing for the Gap. Yes. You can get these clothes or these of clothes from everywhere. Yeah, but the conversation and that, you know, the commercials and the music, that's really like that magic of Gap back in the day.
A
When do you think of the Gap's heyday?
C
Well, you know, I cover, you know, malls for a long time. So I think about the 90s and the gap in the mall all as one that the Gap rose up as malls became ever present in America. It was a place that you could get your first job. There was a lot of references in sitcoms and even rap songs referenced the Gap. So I really think about that period. And probably when you even look at the numbers, like, financially for gap, the early 2000s was really its peak.
A
Oh, that's interesting. How much of a powerhouse were they? Is there any way that you can sort of describe that?
C
Yeah. Annual revenue back then was around $15 billion. And for comparison, now, like, Old Navy is around 8 billion.
A
Wow. So that's a huge difference. Yeah. That's amazing. You know, I think of the Gap as having a certain style component that maybe some other stores didn't have. You gotta love the shopping bags with Their drawstring handles. Right. I mean, they just had that little edge that maybe you wouldn't find in other stores. And maybe you can say more about this sort of cultural role that the Gap served, because there was this connection to, you know, music and celebrity culture, too, that not everyone can tap into.
C
Yes. I think about the Individuals of Style campaign, which was very, you know, photography heavy. Very. It was the cultural conversation I was talking about where you had Spike Lee and Joan Didion, and I think even Whoopi Goldberg, you know, was in their jeans. And, sure, they're selling us the jeans, but it's like, look at all these cool people who are making art in our culture also being associated with the Gap.
A
That's interesting. So in a way, the Gap had a little bit of that cultural cool. When did its star begin to fall? And I wonder why.
C
So during this period, it was run by a man named Mickey Drexler, who was considered like the merchant prince. He just knew what to put in front of you, and people would buy it. And, you know, was really thinking about the commercials, the marketing. He was just kind of genius. He left the company abruptly in the early 2000s. A lot of people, you know, use that as a marker of. Then the Gap started to change, but it wasn't just what was happening inside the company. That's the same time that the rise of fast fashion happened. I think Uniqlo came to America around that time. You get H and M, you get all of these other competitors that were competing on the same type of wardrobe. They were offering people the same type of wardrobe that the Gap was. And at the same time that the Gap was not hitting those commercials and weren't ever present in people's lives. So I think they just fell out of the conversation.
A
You know, you were talking about how, you know, you had some of these fast fashion brands, H and M, Zara. Isn't it interesting that they sort of ran themselves like a tech company in a way, instead of a clothing brand? They were very quick to jump on trends and mass produce the latest thing. Gap didn't seem to care.
C
Yeah, they were operating like the rest of the traditional retail industry, and companies like Zara and H and M just kind of came in like a pool in the china store. It's like, hey, we're switching it up. And maybe for too long, companies like Gap saw those companies on a different track compared to stealing their same consumers.
A
It was almost as if the Gap bought into the idea that they are brick and mortar and sort of didn't Keep up. So they tried to revive the brand's relevance. Shall we go ahead and jump into its partnership with. Yeah.
C
Yes.
A
You might almost think that that was an inspired idea once upon a time, but.
C
Oh, absolutely. I remember the day they announced this. So clearly. It was a Friday in June, in 2020, so it was still lockdown time. It was still the time when a lot of Gap stores were closed because of the COVID pandemic, as were most retailers. And so when it was announced, it was like, wow, this is a fresh idea. This is exciting. Maybe they've landed on that cultural moment that analysts and people have been waiting for. And I remember the day they announced that the stock went up, like, 40%, the most in decades.
B
Wow.
C
A lot of people anticipated that this would be a cool thing. Kanye had his deal with Adidas, and that was working well. And so it's like, great. You're gonna make clothes and bring in a whole different, you know, type of demographic, younger people, that quickly fell apart, as we all remember.
A
Yes. Alas, I think a lot of us know what happened with it sort of crashing and burning. And, you know, you look back at that, and you sort of think, what were they thinking with this partnership with Kanye West? You gotta remember, I mean, he was hot. When the Gap plugged into that, do you think that had Kanye west not, you know, made all sorts of incendiary statements and in a way, almost undermined the partnership in a sense that. That had a real chance of getting the Gap back on track. Could it have worked?
C
I think it could have, because after Mickey Drexler left, I feel like every CEO was chasing relevancy, like, making sure that the Gap could be relevant. And Kanye was that. It came out of left field. It was like, whoa, you guys are making big swings. Like, that's a whole different, you know, category that you guys are going into. And I think that going back to the question was an inspired choice. It's like, hey, what we've been doing for the past decade has not been working. How about we try to switch it up in a big way?
A
So as the Gap was trying to navigate a comeback, it brought in a new CEO, Richard Dixon. Tell us about Dixon. I think he joined in August of 2023. Ex Mattel, right? A toy executive.
C
Yes. Okay. Yes. But we have to go back to summer 2023, also known as the Summer Barbie. Remember all the commercials? You could not not see pink.
A
I remember.
C
And so Richard Dixon at Mattel, he was their coo, I believe, and he was very instrumental in Making sure we all saw Pink and Barbie.
A
Mission accomplished. My gosh.
C
Exactly. And he was known for revitalizing other brands within the Mattel, you know, family. So Gap wanted him because he's a brand guy. He knows how to bring brands back to their relevancy. And so he had been on their board before. And then when he stepped into the CEO role, he could quickly get moving, identify the problems, and start addressing them with real solutions.
A
How do you think he's doing? I mean, it's hard to take a brand like the Gap and do with it what he was able to do with Barbie at Mattel.
C
Yeah. And a lot of people had questions about it. Could it be a one for one? Is Barbie so different than clothes? In his background, he had worked at retailers, so it wasn't a completely new industry. But what we're seeing from the Gap now is commercials. The music, their content comes up on my TikTok. You know, they're back in this conversation. They hired Zac Posen as artistic director, I believe is his title. And so they're on the red carpet at the Met gala. There's this back in a conversation, which I think it sounds simple, but it's a big thing to even have a newer generation talk about Gap in the today compared to back in the day.
A
So maybe what he's doing is he's sort of reinventing the Gap, bringing it back to its roots as a pop culture brand. Do you remember that ad with the singer Tyla that sort of focused on the linen collection, Right?
C
Yeah.
A
That seemed to be huge for the Gap.
C
I even went back to look at that ad on TikTok, and one of the comments was like, idk what you're selling me, but I'm sold.
A
You know, like, see, that's what you want. That's what you want.
C
She never says, and buy, you know, these jeans. She's dancing. It's fun, it's cool. The choreography keeps your eye. Like, people just want to see what they're selling. And it opens. At least it opens the door. You don't know if you got that customer, but it opens the door for them to even think about you when you know they're thinking about Zara, H and M and all the other places.
A
Have you seen the Gap ad that came out more recently about denim with Kelis?
C
Yeah, Kelis Milkshake.
A
Yeah, yeah, yeah, yeah. Was it Cat's Eye?
C
Yes. Once again, thinking about. Okay, what feels very relevant for today, while also hearkening back to, like, the glory days. So there's this cool dotted line that they did within that commercial of, like, hey, we're playing music from that time that you're probably thinking of the Gap, but here we're putting Cat's eye in front of you. And maybe half of the people watching this don't know who Cat's eye is.
A
Yeah.
C
But the other half do and might not know about Gap's glory. So then you kind of COVID like, two demographics.
A
And the ones who do have a wallet that's got some money in it. I mean, that's the thing, right. They're getting in front of people, playing on the whole nostalgia thing, and again, making something that mom and dad might be more familiar with. Cool again, man. That's solid gold.
C
Mm. But it's so important to get the young people now. Cause we say Gen Z, and we're probably thinking about teenagers, but the oldest Gen Z is, like, late 20s. So the time is now to be, like, putting in front of them their artists and their rappers, because they do they have some money. Not all the money, but they have some money.
A
Now, Jordan, here's a warning, because what Jordan Holman says when Jordan Holman speaks, people listen. So here we go. Do you think. Do you, Jordan Holman, think that the Gap has regained its mojo? No pressure.
C
Oh, David, you know, I'm gonna go, yes, here. Because as someone who's covered the Gap since before the pandemic, their performance was always choppy. You know, they might have one good quarter. Everyone's like, oh, maybe this is good. They come back, and then it would be sales decline the next quarter. But what Richard Dixon has done since his time is had consecutive quarters of growth. And me having covered this company, I know that has been a challenge. And so for that reason and with the good commercials, I'm going to say I think they have their mojo back.
A
Ooh, I like it. I like it. Yeah, you got to plant that flag, Jordan. All right, so do you think that viral ads are enough to keep this brand cool now that it's cool again, or does Richard have to have some other tricks up his sleeves?
C
Do you think ads aren't enough? It definitely will have to come down to the clothes, the merchandising, the quality, like we were just discussing. Yeah, ads get you in the door to have a conversation with people, but it certainly doesn't, like, close the deal. Any retail chief knows this. He knows this. So I would say that, like, ads are great, but what's the clothes looking like?
A
You think they look good?
C
I have to still see, you know, I think what's cool that I'm seeing from them now is how they're showing how to style. I think that's another advantage that they have. It's like, okay, these things can go together. You might have not thought of them together. And that goes back to like having that artistic direction and the red carpet. It just already elevates it in your mind.
A
Jordan Holman is a retail reporter for the New York Times. Jordan, great to talk with you again. Thanks so much for speaking with us on Business Wars.
C
I love coming here. Thanks for having me.
B
Coming up, if it had not been for Old Navy, the question becomes where would the Gap be?
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Today we'll talk with a true veteran of the Gap story with a behind the scenes look at the launch of a brand that's become a household name and Gap's biggest moneymaker. Stay with us. Closing the books, getting your people paid and bringing on new hires Running a small or mid sized business can be exciting and also a little chaotic. Workday Go makes simplifying your business well, simple. Imagine all the important aspects of your company, hr, finance and payroll, or all on the AI platform. No more juggling multiple systems, no more worrying about growing too fast. Just the full power of Workday Go, helping small to mid sized businesses like yours scale and run more smoothly. Think about what that means. Seamless onboarding for new team members, real time insights at your fingertips, and payroll that works perfectly every single time so you can focus on the big picture and go after your big ambitions. And with Workday you can activate quickly in as little as 30 to 60 business days. So simplify your business. Go for growth. Go with Workday Go.
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Welcome back to Business wars. In the mid aughts, the shining star of Gap Inc. Was not its namesake. Instead, it was the new kid on the block, Old Navy. Gap Inc. Built this brand from the ground up in 1994 to provide a more affordable alternative to the Gap itself. And people couldn't get enough. Old Navy hit 1 billion in sales in its first four years, becoming the first retailer to do so. And even as Gap's popularity waned, Old Navy's performance stayed steady. They considered making it its own entity in 2019, but reversed that decision by 2020. Today we're joined by the man who helped build Old Navy into the powerhouse it is today. Aubrey Avery Jr. Has nearly 50 years of experience in the retail world. He had already made quite the name for himself by the time Gap Inc. Recruited him to helped jumpstart their newest property in 1994, a store called Old Navy that had only two locations at the time. Once Old Navy was a household name, Gap Inc. CEO Mickey Drexler assigned Opry to identify where new Gap Inc. Stores should be placed based on customer feedback and community need. This coming at a time when most retailers just stuck to the malls. Aubrey had quite the tenure at Gap Inc. And he joins us now to talk about what it was like during that golden era. Aubrey, welcome to Business Wars.
B
Thank you so much. I'm really, really excited to be here.
A
Yeah. Let's talk about your experience in retail. Do you remember your first retail job?
B
Absolutely. My first retail job was in a place called Kalamazoo, Michigan. I worked for a small men's and boys specialty store. And interestingly enough, Kalamazoo was dubbed the mall city. It was the first pedestrian mall ever built in the United States. And I had an opportun to work with a great gentleman by the name of Judd Knapper from the Netherlands. He chose me to be a part of his team. And at 16, 17 years old, I was hired at my first job really to unload trucks and clean bathrooms. And I remember one Saturday it got exceptionally busy and they said, aubrey, we need you on the floor. I went out to the sales floor and my boss said, hey, clean up and go out to the floor and we're going to teach you how to sell. So I had a grandmother and I sold her a spray, a suit, and a tie for her grandson. And they said, this is the biggest sale we've had today. Starting off and they said, if you can do this, you can do anything in retail.
A
But of course, your reputation really began to precede you because you became very successful at turning some low performing stores into top sellers. Was there ever a time when you entered a place you had a job to do to turn this place around and you thought, I can't pull this one off.
B
Oh my God, I would be dishonest if I didn't say yes on that. Because of all of the places that I worked throughout my career, I always had underperforming stores, stores that had major operational challenges, merchandising challenges and people challenges in terms of not having the adequate teams and staff in place. And actually at first I said, am I being punished because of this? But the reality is I wasn't being punished. And I feel like if I can go in and assess, talk to the teams, understand what has worked and what hasn't worked, I can find a way collectively with partnerships to learn how to turn stores around. So yes, it's a lot of work, but you learn and you take every skill set from point A to point B.
A
Well, eventually, after all these successes, you, you're recruited to help launch Old Navy. And this was at a time when they only had two stores. I got to ask, what was that interview process like?
B
Oh my gosh, two to three stores in the Bay Area, coma Pittsburgh, California. It was probably something that is so memorable. I had to interview, and this is a true story, with 15 people, I was able to be officially a regional manager for Old Navy. And I had never had that experience. And I said, is this company so great that I need to interview with 15 people? But I interview with the two co leaders at that time, which was Jenny Ming, who later on became the president of Old Navy. Kevin Lonigan, which was her counterpart. He was the stores operations guy and probably every HR person and, you know, operational people that there were. But I interviewed with Kevin last because he was in charge of stores and operations. And I remember my last interview with him was in a fitting room in one of our new stores. And he was another tough guy. And I. And he goes, aubrey, you have a great diverse background, but this, this thing that you're getting involved in now, this is going to be fast. Can you run that fast? And I say, well, I've never run that fast, but I'm sure I can learn. And I said with, I said, with your tenacity and your drive, I have no doubt that we can do it together.
A
So long as you got the support. That's really what it comes down to.
B
Yes.
A
So did you, deep down inside, did you really feel confident, or did you feel like you were in over your head? I mean, did you feel like, look, I got the experience, I've got this down. I'm just sort of wondering if there was something in your past that made you think, hey, I can do this. I can take on this challenge of Old Navy, because that's a huge undertaking.
B
There was definitely some times of doubt, like, could I really do this? My experience said I could, but at this level and this pace, you know, going from three stores to 59 stores in the matter of a few years and generating a billion dollars in business, and just thinking about the fact of, how can we hire people fast enough to run these stores and operate them. It was a lot of support from leadership, and to this day, I still stay in touch with so many colleagues from every aspect of the business. And one of the greatest things about Old Navy was the fact that the teams that were there in the early days, they all became great merchants with other companies. As they grew, they became CEOs and presidents and CFOs, and it's just phenomenal.
A
Was it clear where Old Navy would fit into the retail mix, though? Because, you know, of course, you're going to have different areas that are going to be dominated by different retailers. Old Navy's coming out in the mid-90s. Was it clear that what that gap, no pun intended, that you were trying to fill, what that was going to.
B
Be, really great point. Old Navy came about at a time when there was a need within the corporation. So Old Navy was about family, it was about fun, and it was about price, and that was exceptionally critical. And to be honest with you, there were times that those of us who were in Old Navy in the early stage, you know, we didn't always necessarily feel like we were really a part of the parent company because we were the new kid on the block. We were still learning. Our product wasn't at the highest level of quality initially, as the company was being started, but we figured it out and we grew, and we were hungry, and we wanted to make an impression on our parent company and our two sister division.
A
Interesting. Wow. So internally, you were trying to make a mark, too?
B
Yes, yes. And I remember being asked many years ago, did you feel like you were kind of a little bit of a stepchild within the corporation? And the question. The answer was, yes, we did. We didn't have all the flair and the bells and whistles yet, but what we did have was drive and tenacity under Kevin's and Jenny's leadership. And so as a result of that, the numbers speak for themselves and our excessive and extensive growth really speaks for the industry.
A
It's time for a short break. Our guest is Aubrey Avery Jr. Retail executive producer who helped launch Old Navy from the ground up. And when we come back, we're going to talk more about gaps, glory days and the CEO who took it to the top. Stay with us.
C
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Power so your business can spend more and earn more. Steven, Brandon and Bruno, the business owners of Sandcloud, reinvested their 2% cash back to help build the company's retail presence. Capital One, what's in your wallet? Find out more@capital1.com SparkCash + Termsupply Introducing Family Freedom from T Mobile we'll pay off four phones up to $3200 and give you four free phones, all on America's largest 5G network. Visit T Mobile FamilyFreedom up to 800 per line via virtual prepaid card typically takes 15 days. Free phone via 24 monthly bill credits with finance agreement. Example Apple iPhone 16128 gigs 829.99 eligible trade in. Example iPhone 11 Pro for well qualified credits end and balance due if you pay off early or cancel. Contact us. Hey, welcome back to business. My guest is Aubrey Avery Jr. A retailer who rolled up his sleeves to help turn Old Navy into a household name. Aubrey, you worked with a lot of the top dogs at Gap, including former CEO Mickey Drexler, who gets a lot of credit for the brand's golden age in the 1990s. What was Mickey Drexler like to work with?
B
You know, it was working with Mickey was like working with a legend that you could walk beside. Mickey was creative. He was innovative. He was exceptionally intuitive. If you think back about how Wall street saw Mickey, the term that they used was the prince of Wall Street. He was really a retail prodigy, for the lack of a better way to say it. I had the opportunity when I was a regional manager, the early years of Old Navy, to join him on store visits and market visits and things of that. But what impressed me is that when Mickey visited stores, he would go to the stock room first and he would talk to the sales associates and he would ask them questions. He goes, what do you think about this merchandise? Is it great? Is it going to work? Or is it going to be a markdown. And so he always positioned himself to know what the internal team within our companies, what they thought.
A
And he was sincere about that. You think he was really? He wanted to know what folks behind the scenes thought of the stuff that they were doing.
B
Absolutely. Absolutely. It was not a front. That was genuinely who he was. And some people just get it in terms of understanding the customer that we serve. And Mickey was one of those individuals, and he had a close relationship with the buying teams in the Bay Area, the home office. One of the other things that I think that he did exceptionally well is he would always want to know what the customer thought. And so I think that is a great opportunity for companies to continue to look at as they move forward.
A
How important was Old Navy to Gap's portfolio at the time? And I'm curious why Mickey seemed to be so invested in the success of Old Navy back then.
B
Well, it was really his baby in terms of creating other pathways to expand Gap Inc's platform. When you can create a company that is focused on the entire family, men, women and kids, and then later on, other businesses within that, you get the entire family right, and you make it an experience. And when sometimes people in the retail industry said, this Old Navy thing is probably not going to work. But Mickey is a visionary. And when he selected Jenny Ming with her incredible merchandising skills, Kevin with his incredible operational skills, they just built a powerhouse team around the organization to make it successful. And so as a result of that, Mickey did something in history that no other retailer, which you spoke about earlier yourself, achieved the kind of financial performance that no one in retail history has ever done, even to this day. So he understood the future strategy long term for Old Navy.
A
How did your relationship with Mickey evolve over the years? Do you have any specific memories of what that was like? Sure.
B
Every company that I work with, I was a part of the diversity board. Right. And when you get into larger companies, it was important to know what we were missing in business in terms of our customer and our geography. So I happened to be on a store visit with him in New York. I think it was Fordham Road in the Bronx. We were opening in a new Gap store on Fordham Roads. And so he was going through talking to all the customers. And there was a group of us, probably 10 or 12 of us, that were traveling with him. And one of the things he was asking customers is, what did you think of our new store? And people had a lot of really positive things about the location and things like that. But one customer said it took Me, two trains and a bus to get to this location. And so Mickey asked questions further around that. And so what he understood was that we have a huge opportunity to create some ways to develop stores in non traditional markets. And I happened to be present when that happened. And later on, as a result of that, Mickey created this position called Director of Urban Real Estate Development Strategies, and myself and one of my colleagues were selected to do that.
A
Now, I understand in this role, you helped Gap, Inc. Expand into Harlem, but there was some pushback at first. How did you eventually bring the story into the community?
B
I can remember it as if it was yesterday in the corporate office. Someone called and said this kind of a fire happening in Harlem, and wasn't a literal fire, but it was a community fire. And so Gap had started marketing on billboards in Harlem before we actually even build a store in Harlem. And so the call came that Harlem is in an uproar because the people of Harlem are very upset with Gap because they put this billboard up and there were no people of color on that billboard. And Harlem is not a place you want to go and not have representation. So the call gets down to us, and they said, well, does anybody know anybody in Harlem? And so none of us knew anybody in Harlem. So we were able to reach out to Magic Johnson and Ken Lombard. Of course, everyone knows Magic Johnson. Ken Lombard was the president, Magic Johnson's Development Corporation. So I got a chance to run down to Beverly Hills, got an appointment with Mr. Johnson and Mr. Lombard, and since they had a presence in Harlem and other markets that we weren't in yet, he said, reach out to Abyssinian Baptist Church and Reverend Calvin Butts. That's the person, if you want to know the pulse of heart, that's where you go.
A
That's some deep intel right there.
B
Yes. So we did that. And Reverend Butts, who is well known around the world and around the country at that time, introduced us to his niece because they were very involved in Harlem's growth and development. And we got the situations resolved, and it gave us a foothold by understanding the community. And then later on, we built our first Old Navy store in Harlem. So it pays to know the communities, know the players, talk to the communities. When you go in, you just can't go in because you're a brand name company. You really have to know the market and understand what's important for the market.
A
I want to fast forward to the early 2000s. What was going on at the company then, And I'm just curious how that affected your ultimate decision to leave the company. Could you say more about that?
B
Sure, absolutely. I have spent all of my time in stores, operations, and the last couple years with the Ho Irvin real estate development strategy. And so they said, aubrey, business is getting tough, which it was. And of course, whenever you create new concepts, those are the concepts that generally are affected immediately. So we were closing stores, the sales weren't as strong, and I really wanted to look at doing some other things. So I actually took a couple years off, travel around. I, I, I can almost say travel around the world because I did. And I did consulting for the International Council of Shopping Centers. I did consulting for the city of Los Angeles on, wow, several projects. And I just wanted to expand my own personal growth just based on the new things that I've learned in this long journey. Yeah, yeah.
A
Well, now, right after you left, Gaps Star began to fall. I know Mickey left in 2002, I believe it was. How did you view what was going on with the Gap since you now had some distance from it?
B
Well, I think one of the challenges that was so hard hitting for all of us was the fact that our sales were plummeting. We were having to close stores in different geographies around the world. We kind of lost our focus and our path in terms of merchandising. The customers were not responding positively to it. It was a tough time. It's hard to go when you've been on top of the world until you slip and then you got to figure out, how do we regrow, redevelop our company going forward? It was a very sad time. But at the same time, like every great company, if you do it right, you go back and you try to reinvent yourselves, it just may take longer than it did initially.
A
Seemed like Old Navy sort of was able to hold on to more of its mojo than the Gap did, I guess. What do you think was going on?
B
Well, I think Old Navy had a position in the retail industry that was appropriate for its time. Old Navy had the whole family under one umbrella. And so it wasn't just the mom taking the kids to Old Navy. It was the dad, it was the grandmother. It was the uniqueness of this company. And when you look back and they, you know, they're doing 54, 56% of the whole corporation's business.
A
Yeah.
B
When at one point, they were going to be sold off and operated as a separate company. And if it had not been for Old Navy, the question becomes, where would the Gap be today?
A
Seems like after some tough years, the Gap brand is back on the upswing under their new CEO, Richard Dickson. You see any parallels to the Mickey Drexler years by any chance?
B
Absolutely. When you look at Richard and you look at Mattel and Barbie and all of the things he did in that industry and in his earlier years at Jones, if I were to do a comparison between Mickey and Richard is it's like running a race. So if you run a relay, it depends on how the baton is passed to person two, three and four. And I think Mickey did an incredible job of building the foundation of a phenomenal company. I think Richard is going to take that foundation. He'll be at the end of the baton, the last pass. I think he's going to take it to a whole nother level. I think it's about digital, it's about music, it's about AI, it's about understanding who your customer is. Now, he seems to be very people oriented as well. I think they both are specialists in their genre of skills and I like the energy that's coming out of Old Navy. It's actually reminding me of the early energy of Old Navy from the beginning.
A
Aubrey Avery Jr. Is a retired executive who's led teams at Gap Inc, TJ Maxx, Ralph Lauren and other retail giants. It's been a real honor and privilege to get to say hello to you, Mr. Avery. Thank you so much for joining us on Business wars and congratulations on, I mean, what a career.
B
Thank you so much. It has been an absolute pleasure.
A
Coming up, the pharmaceutical giant Novo Nordisk launched a blockbuster drug called Ozempic, but that didn't guarantee success forever. Now the company has to reckon with its biggest competitor, Eli Lilly, as well as a host of copycats. Make sure to join us next time time on Business wars from Wondery. This is episode three of Gaps Revival for Business Wars. I'm your host, David Brown Kelly. Kyle produced this episode. Our lead sound designer is Kyle Randall. Our producer is Tristan Donovan. Our audio engineer is Sergio Enriquez. Our managing producer is Desi Blaylock. Our senior producers are Jenny Bloom and Emily Frost. Our executive producers are Jenny Lauer Beckman and Marshall Louie. For wondering attacked by a bear and left for dead, hear the true story that inspired the Revenant starring Leonardo DiCaprio. Can Hugh Glass crawl hundreds of miles to safety to confront the scoundrels who abandoned him? I'm Ray Winston and this is History's Toughest Heroes from the BBC. Listen to History's Toughest Heroes on BBC.com or wherever you get your podcasts.
Original Airdate: November 13, 2025
Host: David Brown (A)
Guests: Jordan Holman, NYT retail reporter (C); Aubrey Avery Jr., former Gap Inc. executive (B)
This episode examines the dramatic efforts to revive Gap, one of America’s iconic retail brands, after years of decline. Host David Brown, with guests Jordan Holman and Aubrey Avery Jr., traces Gap’s historical “cool,” its struggles against fast fashion, its viral new campaigns, and the enduring power of Old Navy, Gap Inc.’s sleeper success story. The discussion weaves between nostalgia and strategy as Gap’s new leadership tries to recapture relevancy with new tactics and a return to its roots in culture and community.
(00:01-05:15)
"I did go to the Gap, but you would probably see me more often in Old Navy...remember, their $1 flip flops and, you know, American T shirts." (C, 04:57)
(05:16-10:54)
"What Gap did was they hit on culture, they hit on music and photography...it was cool and ever present and it was at every mall." (C, 06:27)
"It's like, hey, we're switching it up. And maybe for too long, companies like Gap saw those companies on a different track compared to stealing their same consumers." (C, 10:31)
(11:10-13:20)
"It came out of left field. It was like, whoa, you guys are making big swings...what we've been doing for the past decade has not been working. How about we try to switch it up in a big way?" (C, 12:45)
(13:20-15:38)
"There's this back in a conversation, which I think it sounds simple, but it’s a big thing to even have a newer generation talk about Gap in the today compared to back in the day." (C, 14:48)
"I even went back to look at that ad on TikTok, and one of the comments was like, idk what you're selling me, but I'm sold." (C, 15:25)
(17:19-19:15)
"What Richard Dixon has done since his time is had consecutive quarters of growth...and so for that reason and with the good commercials, I'm going to say I think they have their mojo back." (C, 17:39)
"Ads are great, but what's the clothes looking like?" (C, 18:28)
(21:59-28:52)
"Going from three stores to 59 stores in the matter of a few years and generating a billion dollars...you just kind of grow, and we were hungry." (B, 27:59)
(28:52-30:46)
"We didn't have all the flair and the bells and whistles yet, but what we did have was drive and tenacity...our excessive and extensive growth really speaks for the industry." (B, 30:12)
(32:33-36:56)
“He would always position himself to know what the internal team within our companies, what they thought.” (B, 33:33)
(36:56-39:11)
“So we did that. And Reverend Butts...introduced us to his niece...and we got the situations resolved, and it gave us a foothold by understanding the community.” (B, 38:31)
(39:11-41:55)
"It's hard to go when you've been on top of the world until you slip and then you got to figure out, how do we regrow, redevelop our company going forward? It was a very sad time." (B, 40:32)
(42:06-43:24)
"...If you run a relay, it depends on how the baton is passed to person two, three and four. And I think Mickey did an incredible job of building the foundation of a phenomenal company. I think Richard is going to take that foundation...to a whole other level." (B, 42:18)
The episode mixes business analysis, behind-the-scenes stories, and cultural nostalgia. There’s optimism about Gap Inc’s future thanks to Dixon’s renewed focus on cultural relevance, viral campaigns, and product direction. Old Navy’s legacy as an industry disruptor and community connector is celebrated. The guests’ candid reflections, especially on leadership and learning from failures, add human depth to the story.
[For anyone who missed the episode, this summary captures the rich interplay between retail history, branding, and leadership—and why the next chapter of Gap Inc. is one worth watching.]