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Mickey Drexler on the state of retail in 2025 | Rapid Response

About Mickey

  • Transformed Gap from $400M to $14B in sales; founded Old Navy & Gap Kids
  • Served as Director of Apple Inc. (1999-2015); co-created iconic Apple Store
  • Chairman & CEO of J.Crew, elevating it to a premier specialty retailer
  • Founded Madewell, expanding J.Crew's brand portfolio
  • Advisor and investor at Alex Mill, continuing leadership in retail innovation

| 22:40

Mickey Drexler redefined retail by radically remaking Gap and J Crew, and working alongside Steve Jobs to guide the creation of the Apple Store. Drexler joins Rapid Response to assess some of the biggest stories in the retail industry today, from the weight of crippling tariffs and US manufacturing skepticism, to Sydney Sweeney’s controversial American Eagle campaign. Feisty as ever, Drexler shares his unvarnished view on in-office work, AI’s limitations, and why leaders need to follow their gut or get out of the way.

Chapters
00:00 Introducing Mickey Drexler
01:20 The state of retail in 2025
04:43 The limitations of AI in retail
07:39 Why Mickey Drexler believes “less is more”
09:40 How the leadership landscape has changed
12:00 Mickey Drexler on Sydney Sweeney’s American Eagle ad
15:13 Why Mickey installed an office-wide loudspeaker system at J.Crew
18:11 Trump tariffs and the future of retail

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Lessons from Steve Jobs, Gap & J.Crew
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