161. – Mickey Drexler

Mickey Drexler is a master of retail. He’s the former Chairman and CEO of The Gap and J Crew, served on the board at Apple for 16 years with Steve Jobs, started Old Navy, and now runs Alex Mill with his son. He’s an investor and advisor for many others. We chat about infrared saunas, walking across New York, keeping a short haircut, why a Hermes saddle makes the perfect gift, growing up in The Bronx, our favorite malls in America, buying clothes and keeping them forever, what it takes for a clothing store to turn him on, how Steve Jobs got him to join the board at Apple, his favorite cars through the years, and how Chris plans to follow Mickey in his footsteps.

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