Intro

This chapter explores the career of a notable retail leader, focusing on his impactful role at The Gap and the development of brands like Old Navy and Madewell. It shares insightful anecdotes from his experience on Apple's board and lessons learned from Steve Jobs, highlighting his distinctive decision-making and hiring approach.

Transcript

chevron_right

Play full episode

chevron_right

Transcript

Episode notes

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!

—

In This Episode We Cover:

(02:53) Welcome Mickey Drexler

(03:29) Mickey’s childhood in the Bronx

(12:40) The traits Mickey looks for in people he’s hiring

(14:56) Why Mickey values kindness and treating others fairly, regardless of their status

(16:40) Why the best training is doing the job

(18:40) Mickey’s high standards, obsession with data, and the importance of instinct

(28:39) How Steve Jobs persuaded Mickey to join Apple’s board

(32:33) What Mickey admired about Steve Jobs

(34:20) Why a bad decision is better than indecision

(36:34) What makes a great website