<p>In today’s episode of <em>Big Shot</em>, we’re joined by retail legend Mickey Drexler, whose transformative leadership reshaped some of the biggest names in fashion. </p> <p>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. </p> <p>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: </p> <ul> <li>Mickey’s humble beginnings in a one-bedroom apartment in The Bronx</li> <li>Mickey’s heuristic for hiring and what draws him to people</li> <li>Mickey’s friendship with Steve Jobs and what it was like serving on each other’s boards</li> <li>The importance of urgency and why a bad decision is better than indecision</li> <li>How Mickey does market research, and his process behind both The Gap and Old Navy</li> <li>Mickey’s thoughts on entrepreneurship, his family, and much more!</li> </ul> <p>—</p> <p><strong>In This Episode We Cover:</strong></p> <p>(02:53) Welcome Mickey Drexler</p> <p>(03:29) Mickey’s childhood in the Bronx</p> <p>(12:40) The traits Mickey looks for in people he’s hiring</p> <p>(14:56) Why Mickey values kindness and treating others fairly, regardless of their status </p> <p>(16:40) Why the best training is doing the job</p> <p>(18:40) Mickey’s high standards, obsession with data, and the importance of instinct </p> <p>(28:39) How Steve Jobs persuaded Mickey to join Apple’s board</p> <p>(32:33) What Mickey admired about Steve Jobs</p> <p>(34:20) Why a bad decision is better than indecision</p> <p>(36:34) What makes a great website</p> <p>(39:43) Mickey’s process for helping The Gap standout</p> <p>(46:32) Why Mickey calls the fashion business a commodity business</p> <p>(47:20) How Dayton Hudson’s Target stores inspired Mickey to build Old Navy</p> <p>(54:15) How Mickey got the name for Old Navy</p> <p>(57:42) The challenges Mickey faced opening Old Navy </p> <p>(1:00:20) How the meaning of value depends on the individual customer</p> <p>(1:05:29) The call from Steve Jobs that marked an end to Mickey’s time at The Gap</p> <p>(1:11:20) Mickey’s wife, Peggy’s background</p> <p>(1:13:22) Mickey’s experience taking J. Crew private</p> <p>(1:18:17) How Mickey balances work and family </p> <p>(1:20:03) Mickey’s thoughts on Jewish entrepreneurship, especially in the fashion industry</p> <p>(1:21:52) Mickey’s parting advice on learning entrepreneurship thoughts on school</p> <p>(1:23:37) What David learned at school, and Harley’s learnings from Mickey</p> <p><br /></p> <p><strong>Where To Find Mickey Drexler</strong></p> <p>• X: <a href="https://twitter.com/millarddrexler" rel="ugc noopener noreferrer" target="_blank">https://twitter.com/millarddrexler</a></p> <p>• Instagram: <a href="https://www.instagram.com/mickeydrexler/" rel="ugc noopener noreferrer" target="_blank">https://www.instagram.com/mickeydrexler</a></p> <p>• LinkedIn: <a href="https://www.linkedin.com/in/millard-mickey-drexler-1b00a9269/" rel="ugc noopener noreferrer" target="_blank">https://www.linkedin.com/in/millard-mickey-drexler-1b00a9269/</a></p> <p><br /></p> <p><strong>Where To Find Big Shot: </strong></p> <p>• Website: <a href="https://bigshot.show/" rel="ugc noopener noreferrer" target="_blank">⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠</a><a href="https://www.bigshot.show/" rel="ugc noopener noreferrer" target="_blank">⁠⁠⁠⁠⁠⁠https://www.bigshot.show/⁠⁠⁠⁠⁠⁠</a></p> <p>• YouTube: ⁠<a href="https://www.youtube.com/@bigshotpodcast" rel="ugc noopener noreferrer" target="_blank">⁠⁠⁠⁠⁠⁠https://www.youtube.com/@bigshotpodcast⁠⁠⁠⁠⁠⁠</a>⁠  </p> <p>• TikTok: <a href="https://www.tiktok.com/@bigshotshow" rel="ugc noopener noreferrer" target="_blank">⁠⁠⁠⁠⁠⁠https://www.tiktok.com/@bigshotshow⁠⁠⁠⁠⁠⁠</a></p> <p>• Instagram: ⁠<a href="https://www.instagram.com/bigshotshow" rel="ugc noopener noreferrer" target="_blank">⁠⁠⁠⁠⁠⁠https://www.instagram.com/bigshotshow/⁠⁠⁠⁠⁠⁠</a>⁠  </p> <p>• Harley Finkelstein: <a href="https://twitter.com/harleyf" rel="ugc noopener noreferrer" target="_blank">⁠⁠⁠⁠⁠⁠⁠https://twitter.com/harleyf⁠⁠⁠⁠⁠⁠⁠</a> </p> <p>• David Segal: <a href="https://twitter.com/tea_maverick" rel="ugc noopener noreferrer" target="_blank">⁠⁠⁠⁠⁠⁠⁠https://twitter.com/tea_maverick⁠⁠⁠⁠⁠⁠⁠</a></p> <p>• Production and Marketing: <a href="https://penname.co/" rel="ugc noopener noreferrer" target="_blank">⁠⁠⁠⁠⁠⁠⁠⁠https://penname.co⁠</a></p>

Big Shot

Big Shot

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

OCT 24, 202485 MIN
Big Shot

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

OCT 24, 202485 MIN

Description

<p>In today’s episode of <em>Big Shot</em>, we’re joined by retail legend Mickey Drexler, whose transformative leadership reshaped some of the biggest names in fashion. </p> <p>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. </p> <p>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: </p> <ul> <li>Mickey’s humble beginnings in a one-bedroom apartment in The Bronx</li> <li>Mickey’s heuristic for hiring and what draws him to people</li> <li>Mickey’s friendship with Steve Jobs and what it was like serving on each other’s boards</li> <li>The importance of urgency and why a bad decision is better than indecision</li> <li>How Mickey does market research, and his process behind both The Gap and Old Navy</li> <li>Mickey’s thoughts on entrepreneurship, his family, and much more!</li> </ul> <p>—</p> <p><strong>In This Episode We Cover:</strong></p> <p>(02:53) Welcome Mickey Drexler</p> <p>(03:29) Mickey’s childhood in the Bronx</p> <p>(12:40) The traits Mickey looks for in people he’s hiring</p> <p>(14:56) Why Mickey values kindness and treating others fairly, regardless of their status </p> <p>(16:40) Why the best training is doing the job</p> <p>(18:40) Mickey’s high standards, obsession with data, and the importance of instinct </p> <p>(28:39) How Steve Jobs persuaded Mickey to join Apple’s board</p> <p>(32:33) What Mickey admired about Steve Jobs</p> <p>(34:20) Why a bad decision is better than indecision</p> <p>(36:34) What makes a great website</p> <p>(39:43) Mickey’s process for helping The Gap standout</p> <p>(46:32) Why Mickey calls the fashion business a commodity business</p> <p>(47:20) How Dayton Hudson’s Target stores inspired Mickey to build Old Navy</p> <p>(54:15) How Mickey got the name for Old Navy</p> <p>(57:42) The challenges Mickey faced opening Old Navy </p> <p>(1:00:20) How the meaning of value depends on the individual customer</p> <p>(1:05:29) The call from Steve Jobs that marked an end to Mickey’s time at The Gap</p> <p>(1:11:20) Mickey’s wife, Peggy’s background</p> <p>(1:13:22) Mickey’s experience taking J. Crew private</p> <p>(1:18:17) How Mickey balances work and family </p> <p>(1:20:03) Mickey’s thoughts on Jewish entrepreneurship, especially in the fashion industry</p> <p>(1:21:52) Mickey’s parting advice on learning entrepreneurship thoughts on school</p> <p>(1:23:37) What David learned at school, and Harley’s learnings from Mickey</p> <p><br /></p> <p><strong>Where To Find Mickey Drexler</strong></p> <p>• X: <a href="https://twitter.com/millarddrexler" rel="ugc noopener noreferrer" target="_blank">https://twitter.com/millarddrexler</a></p> <p>• Instagram: <a href="https://www.instagram.com/mickeydrexler/" rel="ugc noopener noreferrer" target="_blank">https://www.instagram.com/mickeydrexler</a></p> <p>• LinkedIn: <a href="https://www.linkedin.com/in/millard-mickey-drexler-1b00a9269/" rel="ugc noopener noreferrer" target="_blank">https://www.linkedin.com/in/millard-mickey-drexler-1b00a9269/</a></p> <p><br /></p> <p><strong>Where To Find Big Shot: </strong></p> <p>• Website: <a href="https://bigshot.show/" rel="ugc noopener noreferrer" target="_blank">⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠</a><a href="https://www.bigshot.show/" rel="ugc noopener noreferrer" target="_blank">⁠⁠⁠⁠⁠⁠https://www.bigshot.show/⁠⁠⁠⁠⁠⁠</a></p> <p>• YouTube: ⁠<a href="https://www.youtube.com/@bigshotpodcast" rel="ugc noopener noreferrer" target="_blank">⁠⁠⁠⁠⁠⁠https://www.youtube.com/@bigshotpodcast⁠⁠⁠⁠⁠⁠</a>⁠  </p> <p>• TikTok: <a href="https://www.tiktok.com/@bigshotshow" rel="ugc noopener noreferrer" target="_blank">⁠⁠⁠⁠⁠⁠https://www.tiktok.com/@bigshotshow⁠⁠⁠⁠⁠⁠</a></p> <p>• Instagram: ⁠<a href="https://www.instagram.com/bigshotshow" rel="ugc noopener noreferrer" target="_blank">⁠⁠⁠⁠⁠⁠https://www.instagram.com/bigshotshow/⁠⁠⁠⁠⁠⁠</a>⁠  </p> <p>• Harley Finkelstein: <a href="https://twitter.com/harleyf" rel="ugc noopener noreferrer" target="_blank">⁠⁠⁠⁠⁠⁠⁠https://twitter.com/harleyf⁠⁠⁠⁠⁠⁠⁠</a> </p> <p>• David Segal: <a href="https://twitter.com/tea_maverick" rel="ugc noopener noreferrer" target="_blank">⁠⁠⁠⁠⁠⁠⁠https://twitter.com/tea_maverick⁠⁠⁠⁠⁠⁠⁠</a></p> <p>• Production and Marketing: <a href="https://penname.co/" rel="ugc noopener noreferrer" target="_blank">⁠⁠⁠⁠⁠⁠⁠⁠https://penname.co⁠</a></p>