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

Описание: 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:
(00:00) 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
(39:43) Mickey’s process for helping The Gap standout
(46:32) Why Mickey calls the fashion business a commodity business
(47:20) How Dayton Hudson’s Target stores inspired Mickey to build Old Navy
(54:15) How Mickey got the name for Old Navy
(57:42) The challenges Mickey faced opening Old Navy
(1:00:20) How the meaning of value depends on the individual customer
(1:05:29) The call from Steve Jobs that marked an end to Mickey’s time at The Gap
(1:11:20) Mickey’s wife, Peggy’s background
(1:13:22) Mickey’s experience taking J. Crew private
(1:18:17) How Mickey balances work and family
(1:20:03) Mickey’s thoughts on Jewish entrepreneurship, especially in the fashion industry
(1:21:52) Mickey’s parting advice on learning entrepreneurship thoughts on school
(1:23:37) What David learned at school, and Harley’s learnings from Mickey

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Where to Find Mickey Drexler:
• X:   / millarddrexler  
• Instagram:   / mickeydrexler  
• LinkedIn:   / millard-mickey-drexler-1b00a9269  

Where To Find Big Shot:
• Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.bigshot.show/⁠⁠⁠⁠
• YouTube: ⁠⁠⁠⁠⁠   / @bigshotpodcast  
• TikTok: ⁠⁠⁠⁠  / bigshotshow⁠⁠⁠⁠  
• Instagram: ⁠⁠⁠⁠⁠  / bigshotshow  
• Harley Finkelstein: ⁠⁠⁠⁠⁠  / harleyf⁠⁠⁠⁠⁠  
• David Segal: ⁠⁠⁠⁠⁠  / tea_maverick⁠⁠⁠⁠⁠  
• Production and Marketing: ⁠⁠⁠⁠⁠⁠https://penname.co⁠