Mickey Drexler

Millard “Mickey” Drexler is in a different kind of work space, so to speak.

He’s outside the corporate environment and involved at Alex Mill, the fashion firm started by his son, Alex, five years ago. He’s not so manic in that micro-managing style he’s demonstrated over the decades and no longer with the loudspeaker system he had at J. Crew Group to grab the attention of the staff.

“I am a micro manager in everything that a customer sees. Now for the first time, at Alex Mills I am a strategic adviser, so I’m not as detailed,” Drexler said Tuesday evening, during a conversation with Derek Blasberg, YouTube’s director of fashion and beauty, held at Made by We (formerly WeWork) at 902 Broadway in Manhattan.

The former chief executive officer of J. Crew Group and Gap Inc., founder of Madewell and Old Navy, chairman of Outdoor Voices, who has an investment company, is now also an investor in Alex Mill, which was what he was most inclined to discuss at the event. Alex Mill, which emphasizes timeless, not trendy, core styles that aren’t “overthought,” next week is opening its first store, which will be in Manhattan at 63 Greene Street in SoHo.

“Right now, I am focused on Alex Mill, which my son started four, five years ago. It’s a wholesale brand. I thought it would be fun to take on something again. Here is a start-up where it’s your own money, versus the bank of Gap Corp. or the bank of J. Crew Corp.,” said Drexler, 74.

Compared to working at big corporations, at Alex Mill, “You are watching every penny, but then there are times, for me as the investor, we are going to take a risk and go for it. It’s a different experience from when you have a bunch of money to spend on things. Eventually we might raise funds.

“Now I don’t need loudspeakers. There are only 10 of us.”

“Frankly, one of the reasons we are doing our little business at Alex Mill is we think there is need for, as silly as it sounds, really nice clothes that you don’t have to take a mortgage out on,” Drexler said. “I’m stunned at the prices for nice quality clothes.

“I can be helpful, I am a mentor, I don’t know if you would call me a mentor, or a pain in the ass. In my business days running companies, anything and everything a customer saw, I felt responsible for. In my Gap days, when I saw too many sweatshirts, I said cut the production in half. It’s not doing the brand any good. You could logo yourself to death.”

Drexler, a self-described “chief kibitzer,” while speaking to about 300 mostly Millennials at the event, called out a few key players on the Alex Mill team, including Somsack Sikhounmuong, former head of design at Madewell and head designer at J. Crew, now creative director of women’s and a partner in Alex Mill. Drexler’s son was also present, as was Husein Jafferjee. “We have a one day a week chief operating officer, Husein. We can’t afford him five days a week. In all due respect, he’s always available. We have other part-timers,” said Drexler.

In the hourlong, wide-ranging conversation, Drexler spoke of growing up in the Bronx; what got him into fashion; the importance of controlling the product you sell from the design and development to the final sale; Steve Jobs, and feeling devastated getting fired from the Gap, despite having grown the business exponentially and launching Old Navy, the corporation’s enduring cash cow.

And Drexler explained why he installed a loudspeaker system at J. Crew, indicating that when he joined the brand in 2003, “it was kind of going bankrupt” and he felt tucked away working in an enclosed office.

“Every time I called somebody, I got a voice mail, or this is so-and-so’s office.” The company was “getting its ass kicked” by the competition, so Drexler had to create a sense of urgency. “It wasn’t there. So I put in a loudspeaker system. It instilled a huge urgency. If you are running a business nothing can wait if you deem it important.”

The loudspeaker, Drexler added, was a tool to communicate to the 1,500 to 1,700 people at J. Crew headquarters. “I’d say things I thought were relevant…I would ask about real estate, like is anyone from Lincoln, Nebraska, and where do you shop in Lincoln, Nebraska? So when you are opening up all these stores, you want to learn as much as you can about the shopping habits of someone who lives there.” Or he would ask, “How many of you like a certain style, or how many are wearing the downtown field jacket? It’s constant feedback. I was always doing a lot of research.”

Once a week at least, anyone who had an idea or suggestion for the business could see Drexler. “It was called ‘open office hours.’ I want to know every day what people think we could do better.”

Drexler admitted he grew up “looking for the wrong in things. I’m known to be a bit of a kvetch. I like to find things that are wrong in other businesses. In business it actually helps. Sometimes in your personal life, it’s a pain in the ass.”

And one of his big pet peeves is fashion. “Not enough beauty, not enough good product, not enough attention to detail.”

While running a high-profile fashion business has its glamorous sides, Drexler suggested it’s not all it seems from the outside. “You go through your life building companies and running companies, it’s not like you are euphoric when you do well,” Drexler said. “You always feel the pressure or the anxiety of keeping it going, keeping it going on earnings and for all the people who work for you. You keep inventing and reinventing. You are never sitting back, for people I know who run, create and are passionate about their companies, it’s never that easy to feel that great about what you create.”

And in an apparent reference to his bittersweet departures from Gap and J. Crew, Drexler said, “It’s hard to walk to away and feel [the businesses] are being sustained and maintained the way you would have done it.”

Here are other “memories from Mickey”:

• On Steve Jobs and why he wanted Drexler on the Apple board: “I loved Steve. He was the most seductive human being. When he wanted something, he got it. I kept saying I don’t want to join the Apple board, essentially I found most boards boring. It was a stupid decision on my part, Steve wasn’t boring. After a year, he said, ‘If you join my board, I will join your board’ and I said ‘you have a deal.’ He had an agenda. He actually wanted to do what the Gap was doing in terms of creating his own stores — to be a retailer. Steve wanted to learn how to build stores. He said he couldn’t deal with Apple being poorly presented in stores around America. He wanted to have articulation of his brand. That’s what we did at the Gap. That’s what I try to do for a living. We built an Apple store. It looked pretty similar to the [Apple] stores today — timeless design.”

On the learnings from Ann Taylor: “I was 35 years old, a president in training. No one bothered me ever. I just followed my instinct. I learned if you don’t control your own product, you are screwed. I don’t want to be in a business where I don’t rule my product. We created Ann Taylor Studio to design all of our goods. The advantage of being young and not knowing anything is that you will try something. Over the next three or four years, the company rocketed. That was the beginning of me not wanting to get up in the mornings and be dependent on someone else owning my goods at a lower price.”

On getting fired from Gap: “At Gap, we had a really bad two years. When I got there, it was $400 million making $12 million a year. When I left it was $14 billion making a $1 billion a year. Steve Jobs called me the night before and said I was getting fired. I was devastated. I was hurt. I was not feeling good. My family wasn’t feeling good, but it happened. Just when I left, the company turned around. I knew it was going to turn around [because of the changes he made]. In the fashion business, you are guaranteed to hit a wall, you always hit a wall. Sometimes you can’t recover. It’s too big or it’s time to get out.”

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