Episode 38 (Part 1): Mickey Drexler - Former CEO of The GAP & J. Crew

This week on Generating Alpha, I’m joined by Mickey Drexler — one of the most legendary figures in modern retail. Best known for transforming Gap into a global powerhouse and later reinventing J.Crew into a cultural phenomenon, Drexler has earned the nickname “The Merchant Prince” for his unparalleled ability to read consumers, build brands, and shape culture. Over decades, his vision has not only changed how America shops, but also redefined what it means to lead with instinct and creativity in business.

In this first part of our conversation, Mickey reflects on his childhood in the Bronx, including his tough relationship with his father and the values that came from growing up in a working-class family. He shares how those early struggles instilled resilience, independence, and a relentless drive to prove himself — qualities that became central to his career.We trace his unlikely entry into retail, beginning with his very first job at a department store, where he developed a fascination with customers and the details of the shopping experience. From there, Mickey rose through the ranks of the fashion world, eventually becoming CEO of Ann Taylor, where he sharpened the instincts and discipline that would later serve as the foundation for his industry-defining work at Gap and J.Crew.We also dive into Mickey’s people philosophy — why he believes in being brutally honest, how he quickly assesses whether someone is the right fit, and why it rarely takes him more than a few minutes to form a judgment. His candid perspective on leadership and human behavior offers timeless lessons for anyone navigating business, management, or life.