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 (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