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
(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
Where To Find Mickey Drexler
• X: https://twitter.com/millarddrexler
• Instagram: https://www.instagram.com/mickeydrexler
• LinkedIn: https://www.linkedin.com/in/millard-mickey-drexler-1b00a9269/
Where To Find Big Shot:
• Website: https://www.bigshot.show/
• YouTube: https://www.youtube.com/@bigshotpodcast
• TikTok: https://www.tiktok.com/@bigshotshow
• Instagram: https://www.instagram.com/bigshotshow/
• Harley Finkelstein: https://twitter.com/harleyf
• David Segal: https://twitter.com/tea_maverick
• Production and Marketing: https://penname.co
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