I recently interviewed Mickey Drexler on my podcast, Thirty Minute Mentors. Here is a transcript of our interview:

Adam: Our guest today is a legend in the world of retail. A former Fortune 500 CEO, Mickey Drexler was the CEO of a guy who was the CEO of J.Crew, and is the CEO of Alex Mill. Mickey, thank you for joining us.

Mickey: It’s fun to be here. Thanks for having me.

Adam: Your biography often starts with your time as CEO of The Gap, but that ignores the first 50 years of your life. How did you become a Fortune 500 CEO? What were the key experiences and lessons that fueled your rise from growing up in the Bronx to making it into the C suite of a Fortune 500 company?

Mickey: A lot of it has to do with how you grow up; your background, your work ethic, your intelligence about running a business, your emotional IQ, and what might in fact, the DNA given in a sense or not, because I do believe in nature versus nurture, to a large degree in my world. Anyway, my first job was at Bloomingdale's as a buyer. And I did that. And I moved on to Macy's. I did six years at Bloomingdale's, one year at Macy's, four years at Abraham and Straus. And I said I've had it with working for a bureaucratic department store business. And to me by definition, most big companies are bureaucratic, anti-creative, and I was never really satisfied with what I did. That being said, I'm not sure I was that satisfied ever. I grew up in not great circumstances in my home. My mom was ill until she passed away at a young age. My dad was a loving, supportive dad, he was always wanting to be successful, do better. And that in itself, I think drives someone to try to perhaps do better than he or she might do. But I always had a drive to do something well, so I moved to Ann Taylor having said no for a while. But I took over a $25 million business. I loved what I was doing. My bosses were in Washington, DC, so they really weren't around ever. And I got my training, maybe self-taught and I'm a big believer, self-taught or mentoring if you have the right person to mentor you. The most important person I ever worked with was at Bloomingdale's. Second day, their third day, a woman named Katie Murthy was assigned to me, but we went to Europe together. I practiced my craft with her. We went to factories, this is all Italy then. And we were very compatible. Good looking goods, good color, good pricing, and you're going to probably be a successful Jewish family in the Bronx. And you know, only once after that I spent eight years kind of doing my job and not being thrown out. I took over Ann Taylor and ran it until it was, unfortunately, bought out by a big bureaucratic department store company called Allied stores. But I stayed for years because it was a great learning experience- self-taught, again, with the greats and business zoomed. We did what people talk about today, every minute of every day was direct to the consumer. It was very clear to me because in the future the business was not buying goods that everyone else carried. And I learned that lesson, believe it or not, from Brooks Brothers who was owned by the same parent company, high profits, very high profits, and then a good company until it didn't become a good company, but they own their label and they own their distribution. And then there was Benetton- same thing on their label, on their distribution. And that's what we did. We switched from a multi-branded company to an Ann Taylor company, into a studio. We changed the name, then rolled out our own designs and we hooked up with two or three vendors who did our own collection, did that for four years, and then realized that working with Allied stores long-term will get me nowhere, wasn't fun. And I was looking for an entrepreneurial environment where I could have a piece of the company and more of an incentive and where I felt I could make a difference. And along comes Don Fisher at Gap. Don wanted me to start a company. I said, I won't move to California. But I had a list of things that ,essentially in my mind, before I met Don, that would, in fact, become what I thought Gap should be and what America needed. And I eventually said to Don, I can't do this in New York, because Gap will go out of business. Before you know it. He agreed, by the way. He said move to California. Again, long story short, I decided to move for a few years, starting at 18 years, and a very tough three years or four years first for public companies, the stock tanking. And culturally, it was not what I do. It was 57th and 5th to San Bruno California overlooking the airport, the highway, and the cemetery. And I had a really tough time adjusting psychologically to living there. And to the culture in the company- it was so opposite of everything I've known as a New Yorker.

Adam: In many ways, you not only reinvented The Gap, but reinvented retail. And I wanted to ask you, looking back, what were the most important steps that you personally, as a leader took to help drive Gap’s enormous growth?

Mickey: Well, I had a photograph in my mind of what Gap could or shouldn't be. And it was a pretty consistent photograph in terms of what I thought America needed, and what Gap should be. I’ve always found- maybe this is because I grew up in the Bronx- they always found clothes a little too expensive for me. And it goes back to really the double markup thing that went on in America in a dominant way. You know, I'm a maker of goods, I sell to you, I double my price, you double your price. And there you go. So a $100 item should be 60 or $70. It's the very simplistic direct-to-consumer thing, which everyone uses so commonly now. But that was part of it. The other thing, execute on a vision. I brought in three people who would make a very big difference from my Intel days. I brought in a head of marketing, because when it comes to taste, style and intuition, either they have it or they don't. And the culture of Gap was very simple, cheap on sale, and ugly goods. Now, did they purposely buy ugly goods? No, but they didn't know the difference between ugly and not. I went through every single style the company eliminated. I guess we were marking down and liquidating most things. So with me taking these huge markups, Don, I'll never forget, calls me into his office. He says this is a disaster. We're gonna have a horrible quarter. And I said, of course, we obviously must liquidate bad goods and turn it into cash and buy good goods. But when things like that happen, I never say it calmly. I can't become, you know, I said, look, Don, if I can't do this... It's not like I wanted to be fired. I was there for a month. I said I can't do this if I can't take markdowns. And it's to this day, it's a rule about bad inventory. You've got to liquidate it. August 1985. I started November ‘83. And usually, it takes about a year and a half to get something turned around. We're sitting in Carmel, California, and we have started to develop a plan, like a bankruptcy plan. What happens if this thing didn't work? We redid 400+ stores. We redid that refix strip redesign but simple. We put all new goods in 400+ stores. And then you start to think of a nightmare if it doesn't work. And that was probably my most anxious period of my entire career. We got back from Carmel in the middle of August. New goods are all in the stores and we set up a new advertising campaign. Day one was wild. I'll never forget this. I mean, I probably wasn't- I’m not that comfortable. because you're always up against the fingers, middle of August, very near my birthday, two or three days sauce, this is nice if the business went like a rocket. And it was very exciting to see. And very relieved, and everything. The stock was like a rocket. And it was unbelievable. And that was the beginning. August 1985. And it was a simple concept. To me, it was simple. Great goods, great color, simple. And it's been kind of what I do all the time, you know? Simple, good value. And it just took off. And for the first 10 years, I think we were number one on the New York Stock Exchange or some crazy outstanding number of businesses- it was wild. ‘87 stock. When we say ‘87- the crash- stock went from 78 to 18. Not fun, but as I said to the Wall Street Journal, as I look back long term and building. So that was the beginning. And that was the key on Gap. And ‘87 we turned it around again because the economy got better. And probably by 90, it was rocking again.

Adam: Mickey, you highlighted a few really important characteristics of what makes leaders great; vision, adaptability, making difficult decisions. Can you expand on that, in your view? What are the key characteristics of a great leader? And what can anyone do to become a better leader?

Mickey: I think leadership goes along with some pain and suffering you might have felt as a young person. In my case, I just had a thing about doing the job well. And I think intuition and instinct is so important, along with drive and frankly, hunger, you know? I grew up, you know, being hungry. And I kept seven or eight dollars in my drawer. I didn't have a bedroom. And I have a huge curiosity, by the way. I go to work every day thinking that I don't really know that much. And I could learn by reading the New York Times. I was reading page three or five and a New York Times article said Target started a company called Everyday Hero copying a cheaper version of The Gap. And I said, you know, Target’s a company that does a lot of research. So I could write it off in my mind, or I could see what they're doing. So I flew to the Mall of America. And I looked at Everyday Hero. And it took me- like going to a store for three minutes- you get the vibe, you get the feel of that and I walked out saying it’s a really bad version of Gap. They even said in the article, a cheaper version of The Gap. So of course you get competitive. I stopped in Chicago. Long story short, I visited two Gap stores that were in a lower demographic and I spoke to the store managers or spoke to a waiter. I speak to anyone who can teach me. If you're curious and you learn all the time.. The two store managers said we're too expensive for this market. I said, too expensive? I said our prices are really fair. They said well, we're expensively perceived by our customers. When I went back to San Francisco I did some checking around. The Gap’s jeans started 30, 40 50. 80% of the jeans in America were sold for less than $30 Oh my god- voila. Second thing is I gave 10 people $200 each 25 years ago, maybe 400. Today, I said, go shopping in the discount stores. I assigned a store, I assigned categories. I said come back and talk to us. They did that. And two weeks later, I said now this is vision, taking a risk and having a partner who's willing to take the risk. I said we're gonna start a new company. And we did and it was what is today Old Navy, and the rest was history. And now it's the reason that Gap exists.

Adam: When you're CEO of the Gap you created Old Navy. When you were CEO of J.Crew you created Madewell. How can leaders foster creativity, innovation, and intrapreneurship

Mickey: I hate to say this, but I don't think they can unless the leader bets on site. Don, he was the Chairman CEO, he really was the controlling shareholder. He bet on me and we had a good relationship where else I probably wouldn't have stayed there so long. But how can leaders... It depends on how you define a leader. For me, if he or she is creative. If they have a good instinct, if they have vision, then they'll get the job done, if they have a boss or not. But if you are the one who drives those decisions, if you don't get it in your body, then you can't do it.

Adam: Mentorship has been a central theme of your career, you're talking about a key mentor who really fueled your success. And you've mentored so many people who've gone on to become highly successful business leaders. What did you look for when you're identifying individuals within your company or within your industry to decide to mentor? And how did you develop them as leaders?

Mickey: Well, you know, they show up for me. Mentoring is, you know, it's a funny word. It's funny how many people call me their mentor, and I usually feel complimented by that. If I really like their brain, if I like their thoughts, if I think they're hard-working with common sense and have an instinct, I use that word a lot, instinct, then they will pass the test. So I'll spend more time with them. They'll get promoted more quickly. And, they're going to be more successful. Curiosity, speed, urgency, imagination, risk-taking ability, and a gut feeling.

Adam: Along those lines, what are your best tips for listeners on the topic of hiring? Can you talk a little bit more about what you look for and what you would recommend other leaders to focus on when they're trying to build their company?

Mickey: Well, it’s how fast they walk. Okay, it's true. If there's sauntering in my office- it is always open- if it's sauntering around towards the office, it's, you know, I wanted to come in, I want to be a little nervous. I don't want to be palsy. Well see. And then I want to get a sense with conversation about what's up and what's going on. I don't want to do the typical SEO or whatever questions, you know, because you feel it when you have a good interview. I look at resumes, but I want someone who was a waiter,or a waitress or worked real jobs, and worked at Starbucks and did whatever. And I always know in finance, 90% of them got the jobs through connections, which is okay, nothing wrong with them. My kids went through that. But I look at the resume, and then I start to chat. And I want to know, if they work in that environment, what would you do differently if you were the CEO? I always ask that question. What would you change tomorrow? I want to hear a change, I want to hear what the common sense tells them should be different about the company they work in, or the college they went to, or the high school they want to. I want to know if they're thinking out of the box if they have opinions about certain things.

Adam: Something that you focus on, which I love, is trying to understand what is it that they would have changed about a job that they had in the past? And you've been a change agent over the course of your career and I'd love to know if you could share with listeners what advice you have on how anyone can become an agent of change and how anyone can become a transformational leader.

Mickey: Well, you know, agents of change are interesting. They can differ in the wrong environment. For example, when I worked in the department stores, I used to make suggestions. No one listened except one or two bosses I had. Stan Stern listened and after that, Katie Murphy listened. But you have to be in an environment where they listen and value your opinion. And I think most large corporations are filled with people who don't necessarily get their opinions valued. I'm a change agent because I needed to be in a position where I had the ability and the power as, say, the CEO of Ann Taylor to make those changes. But you need to find the right boss. If you can hire your boss, then you're in great shape. If you can't, then you have to evaluate the company. And I think there's a lot of people today who just don't like where they work.

Adam: I agree with everything you said. And a question that I'm often asked is, how do I evaluate the company that I'm looking into working for? What are the kinds of things that I should do when I'm assessing whether this is the right company for me? Is this the right environment for me? Is this the right job for me? How would you answer that?

Mickey: Well, it's a good question because it's kind of the same way you might evaluate a fancy school. I don't want to say fancy- a great college. I'll tell you what happened to me when- this is a million years ago- I'm touring JC Penney when they were in New York, and the head of HR said something to me, that was if you don't feel right, in terms of being here, if it doesn't feel like it's a place you want to work, then you shouldn't be here. I walked right out. That was it and I said to myself, am I doing the right thing? I don't want to be in this big building with people who make ugly clothes, you know what I mean? I just didn't want to walk down. And I went through that, actually, a second interview with AMS, which is no longer, it's now Macy's. And I ended up working at Bloomingdale's, which was the best early decision I made because it was a creative environment. And you know, even though it was a big company, I didn't feel any bureaucracy, and I really liked the people. And then within a few years, you know, things settled in, I was always meant, I think, to want things the way I think they should be. And I couldn't help myself, you know, but I also had to make a living. So for 12 years, I was afraid. In fact, I kept turning down Ann Taylor, until a friend of mine who was older, wiser, and rich, said at dinner one night, he said, take the job at Ann Taylor. He said, “You're much better off being the CEO of a $25 million company than a vice president of a $500 million company.” Next day, I called the president of the corporation. And I said, I'm in, I'm gonna take the job, and it changed my career path in a major way. And you have to have good radar. You can put someone in a company for a day, they have to have the right radar to see if the people are the right kind of people and ask the right questions. Go to school, see everyone, and pick brains. And it's not easy. So you gotta work hard. I never had a mentor at all, ever. And every young person I think has mentors. And I would suggest they get mentors who don't grow up the same. Get some street people to mentor you on what it's like in the streets. What are these people like? What are these fancy companies like, you know? Working for some companies, oh, I work at so and so and so and so, you know, doesn't mean anything, if your boss is great, and the company has a great future, and you like the culture, and you order like the product. Now for me, it's the product. Then you take a shot, and you can make a few mistakes.

Adam: Mickey, you've had so many incredible highs over the course of your career. You've also had your fair share of lows, including a tough exit from The Gap and stepping aside from J.Crew during a period of declining cells. A common theme, though, has been your ability to bounce back and bounce back quickly. And when you were the CEO of The Gap, you went from The Gap to J.Crew and now you're leading Alex Mill which was founded by your son. How did you manage these rough moments in your career? And what advice do you have for listeners on how to manage theirs?

Mickey: Well, it's a really good question. I grew up persevering my whole life. I had more tough personal moments than most people grow up with, from a very old mother to a father who didn't pay attention to things like that. I had great training as a kid. I really did. My training, not in business, but in life, was really strong. It was a bounceback life that I lived, I had a very tough, emotional childhood. And I think that created for me, a bounce back. I never gave up on anything. And I always worked hard. And I always wanted things to be different or better. And I'm very competitive. I grew up being competitive quietly. I never was that person in the company who is competitive, but quietly, I did it. I wasn't obnoxious. I never had that. Bloomingdale's, the first day, everyone said, what do you want to do? One guy said he was a fancy guy, and his father ran a big corporation and said I'd like to be vice president here within five years. I said to myself, what a schmuck. Don't say that to all of us.

Adam: Mickey, before we go, I want to ask you a few rapid-fire questions. What are your best tips on the topic of branding?

Mickey: Have a little team that you trust implicitly on creativity, and you go to them to check out what you're thinking. And I've had that every company I've worked in, you know, I might leave the group. But branding is a very personal thing. Very personal. And now there are few people who get it and understand it. But then you've got to find the person who really gets it, who's doing the copy, doing the photography, doing the whatever.

Adam: What are your best tips for retailers? How can retailers succeed today and in the future?

Mickey: Well, the only way they can succeed, in my opinion, is to have the right goods. And what does that mean? The right goods are not defined by the right goods, it’s someone who has a style, a vision and a point of view that starts with the product. But even if it's not the right product, if it appeals to customers, then it's the right product. It's all about product long term, it's not about statistics. And I was doing whatever that word is on statistics when I was 23, I just had a different word. I mean, you've got to be good at numbers, no matter what. And numbers are important. It's investing your cash in the right goods. But there's got to be a point of view on the goods, it's got to stand for something, whether it's not a matter of good looking, bad looking, a point of view, and something that makes sense.

Adam: What can anyone listening do to become more successful personally, and professionally?

Mickey: Personally, just kind of live a good life or have a nice family if you want to have a family, or there's many definitions these days of that as we know. But personally, you know, personal is hard, because a lot of people I know are so demanding of themselves. That personal, sometimes crosses over, but I have a wonderful, supportive wife, and kids, and I'm very happy about that. And career-wise, it's the right partners, you've got to have the right partners. You've got to work with the right people who get you and understand you and appreciate what you do well. Find a great partner who has something you think you can help with and will make a difference with one other thing. I always say if you're thinking something about someone, or an idea, go with your gut. You’re usually right when you're thinking something about people and usually write about an idea. And then you’ve got to test yourself and take the shot on the idea. If you're not willing to make a mistake, then you can't be successful. This is all part of learning and you’ve got to have a partner who's letting you make mistakes.

Adam: Mickey, I love it. Thank you for all the great advice and thank you for being a part of Thirty Minute Mentors.

Mickey: Thank you, Adam. Good to see you.


Adam Mendler is the CEO of The Veloz Group, where he co-founded and oversees ventures across a wide variety of industries. Adam is also the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal winning athletes, political and military leaders - for intimate half-hour conversations each week. Adam has written extensively on leadership, management, entrepreneurship, marketing and sales, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities and non-profit organizations.

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