My lunch with Millard S. Drexler, the 67-year-old chief executive of J. Crew, the American clothing brand made world famous by its First Client Michelle Obama, turns out not to be a lunch. Or to be more specific: not just a lunch. It’s lunch, followed by a short walk, a couple of emails and two phone conversations.
It begins as just a lunch (a nice, two-hour one at Pulino’s pizzeria in New York) but later Drexler, known as Mickey, emails to say he realises he hasn’t answered one of my questions, has given it some thought and would be happy to discuss it if I want to have a phone chat.
This, I have to admit, startles me. After all, the question in question was: “What was your biggest mistake?” and Drexler had answered it, sort of, during our lunch. At the time – we were well into our food – he said, “It’s hard to answer, because I see all mistakes as learning opportunities,” a comment I chalked up to typical management speak, of the anodyne “turn all negatives into positives” kind. But this subsequent call back, in my experience, was not typical.
Typically I find that chief executives of $1.7bn companies such as J. Crew, with its 3,887 employees, 235 stores and its own hipper line, Madewell (face: British model and TV presenter Alexa Chung), are happy to give you the allotted hour and a half or so, then cross you off their to-do list. But Drexler, it turns out, is very consciously not that sort of chief executive.
He grew up in the Bronx, an only child with a father in the garment business and a mother who was a secretary; has been married to the same woman (Peggy, a psychologist) for 42 years; and last summer started doing SoulCycle indoor cycling classes with his daughter, who is in college. His son, who is out of school, works in clothing manufacturing. His favourite pastime is not playing the market or buying art but checking out property: his investments are all homes (an apartment on the Upper East Side, four estates in the Hamptons, including Andy Warhol’s old Montauk place, which he reportedly bought for about $30m) and a few other places.
This could sound very tycoon-like, were it not for his explanation: “Growing up, I always wanted a bedroom of my own.” Given his intelligence and his wife’s profession, it’s hard not to think he knows this is psychologically facile but doesn’t care. He is the sort of chief executive who in other times would have been called “folksy.” He famously has a loudspeaker system in the J. Crew headquarters in New York that allows him to constantly “talk” to everyone he works with and, occasionally, pipe in customers or store managers to talk to them too. He is not, in other words, likely to buy a $1,200 wastebasket for his office, à la former Merrill Lynch chief executive John Thain, which makes him a model chief executive for these Occupy Wall Street times.
Indeed, Drexler’s usual working uniform is a pair of jeans, a “relaxed” (ie wrinkly) button-down shirt, a grey T-shirt and a navy blazer, all of which he sports when he arrives at Pulino’s and all of which, as he shows me later by twisting around and otherwise contorting himself, are from J. Crew.
Drexler likes Pulino’s for a number of reasons. First, it is a few blocks from his office. Second, it is a Keith McNally pizza joint on the corner of Bowery and Houston with iron tables and a chequerboard floor; which is to say it is owned by a hipster restaurateur who gets the importance of neighbourhood, good food and low attitude. Third, it serves pizza, which Drexler is “addicted to. I love that thin crust! Do you love pizza?” he asks. I allow that I do. He looks pleased. He also looks at the waiter, who is hovering and wants to tell us about the specials.
Drexler wants the Marinara. “It’s not on the menu, but you know what I mean, right?” The waiter nods. “But no olives, OK? Take the olives off. And let’s have some of the meatballs – want to try the meatballs?” he looks at me; I nod. “And some prosciutto.” The waiter asks if he wants the ham first. “No – bring it all when she gets her food,” says Drexler, referring to my asparagus and tomato and mozzarella salad. “Bring it all at once,” he says, waving his hands at the table, then amending it to: “Bring it whenever it comes.”
“You know,” he says, leaning in, “wherever I go I always ask what the bestseller is. I was just in London, and I went to the Wolseley – have you been there?” I nod; whenever Drexler makes a reference, he always checks to see if you are familiar with it. “Great place, right? Well I was there for breakfast and lunch, and I asked the waiter what the most popular dishes are. Guess what he said?” he looks at me expectantly. I hazard: “Hamburger?”