Episode 38 (Part 2): Mickey Drexler - Former CEO of The GAP and J.Crew

This week on Generating Alpha, I’m joined once again by Mickey Drexler—the legendary “Merchant Prince” who reshaped modern retail through his leadership at Gap and J.Crew.

In part two of our conversation, Mickey shares his unfiltered perspective on why he’s always had a distaste for corporate America, and how bureaucracy, complacency, and ego often kill creativity. We dive into his definition of good taste—how intuition, curiosity, and emotional intelligence drive product decisions—and the mindset that helped him scale Gap from $400 million to $14 billion while turning it into one of the most recognizable brands in the world.

Mickey also opens up about his leadership philosophy—why he values brutal honesty, how he quickly reads people to know if they’re the right fit, and what it really takes to build an organization fueled by passion and excellence.It’s a candid, wide-ranging conversation that goes beyond fashion—about culture, leadership, and the relentless pursuit of quality. Few people see the world like Mickey Drexler, and his lessons resonate with anyone building something meant to last.

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