Big Shot

The Merchant Prince: The Man Behind The Gap, Old Navy, and J. Crew | Mickey Drexler

Oct 24, 2024

Mickey Drexler, a retail legend, transformed brands like The Gap and Old Navy. He shares insights from his humble Bronx beginnings and emphasizes the importance of people skills in hiring. Mickey discusses his unique decision-making style, valuing urgency over indecision, and reflects on his friendship with Steve Jobs. Listeners learn about the emotional aspects of fashion and Mickey's innovative approach to market research. His journey highlights resilience, the impact of mentorship, and a deep passion for retail.

01:25:14

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Mickey Drexler

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Quick takeaways

Mickey Drexler's leadership at The Gap transformed the company from $400 million to $14 billion, showcasing his innovative retail strategies.

His collaboration with Steve Jobs taught him the importance of urgency in decision-making and trusting gut instincts over prolonged deliberation.

Drexler's humble beginnings in the Bronx instilled in him a sense of empathy and resilience, which he values in both business and hiring.

Deep dives

The Impact of Mickey Drexler on Retail

Mickey Drexler significantly transformed the retail industry, serving as the CEO of The Gap for 18 years and elevating its revenue from $400 million to $14 billion. He was instrumental in the creation of renowned brands such as Old Navy and Madewell, demonstrating a keen understanding of market gaps and consumer needs. His entrepreneurial spirit is reflected in his ability to innovate within the competitive landscape of retail, often attributing his success to gut feelings and instinctual decision-making. Drexler is often referred to as the 'godfather of retail' due to his lasting influence and iconic status in the business world.

Intro

2min

From the Bronx to Success

11min

Navigating Career Choices and Leadership

28min

The Rise of Old Navy

20min

The Emotional Value of Fashion: Beyond Pricing

3min

The Art and Competition of Retail Passion

2min

Turning Points and Personal Triumphs

15min

Threads of Entrepreneurship

5min

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!

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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