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

https://is1-ssl.mzstatic.com/image/thumb/Podcasts116/v4/51/f1/45/51f145d4-c6fb-b9c6-d779-11c646b19c83/mza_1430463201855669484.jpg/600x600bb.jpg

Big Shot

32 episodes

1 week ago

If the walls of Kosher delis could speak, they would (schm)ooze invaluable wisdom and endless laughs. Harley Finkelstein (Shopify) and David Segal (DAVIDsTEA) are Jewish entrepreneurs influenced by the greats who came before them. But, they realized no one was archiving the best behind-the-scenes stories ever told. Before time was up, they set out on a passion project to preserve the memories, mishaps, and wins of the people who have seen it all. Big Shot tells the stories of the people that shaped an entire generation.

Entrepreneurship

Business

RSS

All content for Big Shot is the property of Big Shot and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.

Entrepreneurship

Business

https://d3t3ozftmdmh3i.cloudfront.net/staging/podcast_uploaded_episode/36791457/36791457-1729541506425-ef98d572c54ea.jpg

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

Big Shot

1 hour 25 minutes 14 seconds

1 year ago

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

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