If You Know, You Know | Mickey Drexler on Intuition, Gut, & Seeing Around Corners

Often referred to as “the merchant prince”, Mickey Drexler has defined multiple eras in American fashion. He took Gap’s revenue from $400M to nearly $15B, created iconic brands, Old Navy and Madewell, reinvented J.Crew and took it public in 2006, and today serves as Chairman of Alex Mill and head of Drexler Ventures. Named Retailer of the Decade by WWD, honored by the CFDA, and once described by Steve Jobs as “the best retailer in the world”, Mickey’s career is a masterclass in vision, creativity, and leadership.

In this episode, we explore:

• Authenticity and adversity: Why money was never his motivator, and what truly drives his turnarounds.

• Personal journey: Growing up in the Bronx, living in imagination, and lessons from being fired at Gap.

• Creativity + business: How he balanced merchant instincts with CEO responsibilities, and why creative-led brands often win.

• Mentorship and influence: His friendship with Steve Jobs, recognizing talent and good design

• Merchant mindset: Trusting your gut, simplicity as luxury, and the art of brand building.

• Legacy + future: the state of fashion today, advice for young people and women, and what excites him most at Alex Mill.

Follow Mickey: https://www.linkedin.com/in/millard-mickey-drexler-1b00a9269/ and https://www.instagram.com/mickeydrexler/?hl=en 

Alex Mill: https://www.alexmill.com/ 

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