The Retail Pilot · 2026-05-06 · 1h 10m
Retail icon Mickey Drexler doesn't do retirement. At 80, the man who built Gap into a $14 billion empire, founded Old Navy, and revitalized J.Crew is running Alex Mill like a scrappy startup, and loving it. "I love what I do more now," Drexler says. "I don't have someone breathing down my neck." This is Mickey unfiltered: no corporate boards, no bureaucracy, no focus groups. Just 30 team members, two stores, and a merchant's eye as sharp as when he reinvented Ann Taylor in the 1980s. In this episode of The Retail Pilot, Ken goes behind the scenes at Alex Mill to explore how Mickey operates with startup intimacy and five decades of wisdom. They walk through design boards covered in vintage scarves, discuss why "a great store looks like it was bought by one person," and unpack Mickey's weekend update ritual - clipping magazines, photographing street style, bringing visual inspiration to the team every Monday.
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