This episode will transform how you think about style, aspiration, and the art of knowing what people want before they know it themselves. From working in department stores to advising Steve Jobs on Apple’s retail strategy when it didn’t have retail at all, Drexler’s career traces the evolution of American retail itself: from local shops to mall dominance, from catalog to digital, from mass market to personalization. Whether you’re an aspiring entrepreneur, a retail enthusiast, or someone looking to build a brand that stands the test of time, Mickey shares invaluable insights on what separates truly successful brands from the rest.

Mickey Drexler is the chairman of Alex Mill. Before that, he was the CEO of J. Crew and sat on the Board of Directors of Apple. He founded Old Navy and Madewell, and served as the CEO of Gap from 1983–2002.

Learn why gaining real-world insights—and not just reports or data—is crucial to staying ahead of the competition.

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Watch on YouTube: @tkppodcast

(02:16) How Mickey Drexler became Mickey Drexler

(07:04) Lessons from redefining Gap

(12:47) Merchant, defined

(15:17) How Drexler evaluates stores

(19:20) Lessons from running Gap

(21:19) On Old Navy

(27:26) On Steve Jobs and Working with Apple

(33:00) Re-making J. Crew

(37:00) Drexler's superpower

(43:40) Current-day retailers who are great

(45:10) How Drexler got "Madewell"

(47:15) What makes something a classic look?

(50:20) On success

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