Career Resilience, Risk and Reinvention with the Force Behind Gap & J.Crew

If you’ve ever shopped at Gap, Old Navy, J.Crew or Madewell, you’ve experienced the influence of 'Mickey' Drexler. A retail visionary and former CEO of both Gap and J.Crew, Mickey is known for transforming American brands into global icons through bold decisions, deep customer insight, and fearless leadership. His career is defined by reinvention, not just of the companies he led, but of himself. In this exclusive fireside chat, Mickey reflects on decades at the helm of iconic brands, unpacking the risks that paid off, insights from his time on Apple's board alongside Steve Jobs, and how he continues to shape the fashion industry as Chairman of Alex Mill. Whether you're navigating change, building staying power or stepping into greater leadership, you'll walk away with perspective-shifting lessons to help you move forward with clarity.

Learning objectives

• How Mickey rebuilt after a very public firing and the importance of finding momentum through uncertainty
• Lessons in risk-taking, fear, and knowing when it’s time to move on
• How to think like a CEO — building influence, making tough calls, and staying decisive
• How to spot trends early and apply that lens to stay ahead in your own industry