In today’s episode of Big Shot, we’re joined by retail legend Mickey Drexler, whose transformative leadership reshaped some of the biggest names in fashion.

Over his 18-year tenure at The Gap, Mickey took the company from $400 million to $14 billion in revenue, revolutionizing casual wear and spotting a new retail opportunity that led to the creation of Old Navy.

His influence extends far beyond The Gap—he also founded Madewell, served on Apple’s board for over a decade, and now works alongside his son Alex on the growing success of Alex Mill. In our conversation today, we cover:

Mickey’s humble beginnings in a one-bedroom apartment in The Bronx
Mickey’s heuristic for hiring and what draws him to people
Mickey’s friendship with Steve Jobs and what it was like serving on each other’s boards
The importance of urgency and why a bad decision is better than indecision
How Mickey does market research, and his process behind both The Gap and Old Navy
Mickey’s thoughts on entrepreneurship, his family, and much more!