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