Hello Monday with Jessi Hempel Mickey Drexler on Taste, Intuition, and Building Iconic Brands
Aug 18, 2025
Mickey Drexler, the legendary retail executive known as the “King of Retail,” has transformed iconic brands like Gap and J.Crew. In this conversation, he reveals why taste is crucial in business, arguing that AI can't replicate it. He emphasizes the importance of intuition and listening in fostering creativity and success. Mickey shares lessons on rebounding from setbacks and the emotional connections that drive effective branding. He also discusses how to cultivate one's own taste, regardless of the industry.
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Taste Is More Than Pattern Recognition
- Taste combines intuition, talent, and something ineffable beyond pattern recognition.
- AI can mimic patterns but lacks the emotional core that defines human taste.
Career Rebounds And New Ventures
- Mickey Drexler built Gap into a 1990s style powerhouse and invented Old Navy.
- After being fired he rebuilt his career by leading J.Crew, launching Madewell, and founding Alex Mill with his son.
Prioritize The Customer Benefit First
- Focus product messaging on what matters to the customer first, not jargon or irrelevant features.
- Lead with the emotional or functional benefit like fit, then show variants or fabrics.