Mickey Drexler
American businessman
11
APPEARANCES
9
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Jul 2, 2026
🇺🇸👕 “American Crew” — Interview with Mickey Drexler, ex-CEO of The Gap & J.Crew
8:43
8:53
9:05
Mickey DrexlerGUEST
So I sold them on the street because I bought them, I don't know where, and I had a little side hustle.
Mickey DrexlerGUEST
Anyway, that was a minor thing, but I, so I did that and I worked always Saturdays and I always was forced to work, but it was good.
Mickey DrexlerGUEST
And so I'm a worker and I never give up on things now, now a million years later, but getting into the business, I did that.
17 MINS LATER
Mickey Drexler — The Death of Taste
36:17
36:23
36:29
Mickey DrexlerGUEST
So I said, "Why?" I mean, I said, "Where's the integrity?" I got ushered right out.
Mickey DrexlerGUEST
And then after the press conference [laughs] the next day-Uh, Don said to me, "You know, I made a mistake.
Mickey DrexlerGUEST
Now it's all over the papers, my family was just..." "Oh, okay, you made a mistake." And he said to me, um...
20 MINS LATER
Retail Legend Mickey Drexler: From Building Gap & Old Navy to Running Alex Mill Like a Startup
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K
2:55Ken PilotHOST
Tell us a little bit about the business, but I- I'd love for you to stop, to start at a high level to explain the business in total in terms of where it's coming from, wholesale, stores, and online.
Mickey DrexlerGUEST
Well, uh, it's hard to explain without saying what it was six or so years ago, but in any case, it was only a thought in our minds of what it could be and should be.
Mickey DrexlerGUEST
And frankly, right now we're starting to, uh, get some of the good traction that I always like to see, although it took a bit of time.
Mickey DrexlerGUEST
Well, it was tiny with, uh, no stores when, uh, we started, Alex and I, and, uh, Somsack is the third, uh, relaunch person and, and a founder, uh, in the relaunch.
Mickey DrexlerGUEST
So there's the three of us, uh, and what it was and what it is, it's a long way from that.
Mickey DrexlerGUEST
Um, it was, uh, just a feeling about, uh, vision, uh, et cetera, on what it could be, and now we're getting close, although you never get 100% 'cause you're always climbing the mountain.
Episode 38 (Part 2): Mickey Drexler - Former CEO of The GAP and J.Crew
A
17:05AmirHOST
I have, yeah.
20 MINS LATER
A
37:40AmirHOST
So I'd love for you to just put into words, what do you see the role of a CEO as? Or a leader in any sense?
Episode 38 (Part 1): Mickey Drexler - Former CEO of The GAP & J. Crew
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A
1:57AmirHOST
Yes.
Mickey DrexlerGUEST
And I lived very, you know, now it's not the way you say a lot of people live.
Mickey DrexlerGUEST
But then the Bronx, Barnes Avenue was a very kind of, I don't want to call it a working class family neighborhood, but it was mostly Jews and Italians.
Mickey DrexlerGUEST
One elevated stop north of Pelham Parkway, which most people know because Bronx Zoo, a hospital.
17 MINS LATER
A
19:23AmirHOST
Yeah, but throughout your career, after your kind of childhood, whether that be Gap, Old Navy, J.Crew, Alex Miller, what are your biggest thoughts?
Closing Bell: Debating the Market’s Next Move 8/28/25
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34:37
Scott WapnerHOST
Are you eating the cost of higher goods? Are you passing it on? How do you deal with it?
Mickey DrexlerGUEST
How do we deal with it? You know, use our judgment, our intuition, our gut, which are three important characteristics.
Scott WapnerHOST
Do you hesitate to do anything that could cause a storm on one side of the political aisle or the
Lessons from Steve Jobs, Gap & J.Crew, with retail icon Mickey Drexler
7:19
19:18
Mickey DrexlerGUEST
One woman was on the board of AI, and they were all my friends, but I get a little passionate.
12 MINS LATER

Bob SafianHOST
Was that the goal? Like, how calculated were you about that? Or was that, again, just gut?
Closing Bell: The Momentum Mess 2/20/25
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Mickey DrexlerGUEST
There's price issues out there, which, you know, some of the prices are whatever.
Mickey DrexlerGUEST
And the people, I think, this is a personal opinion, it's not such a big deal to wear designer clothes.

