Mickey Drexler is the former CEO of Ann Taylor, The Gap, J. Crew, and is a former board member of Apple and Warby Parker. He is currently the CEO of Alex Mill, a digitally native vertical brand, founded by his son Alex Drexler. He has been dubbed the “Merchant Prince” for his successful turn around of Ann Taylor, and his dramatic transformation of The Gap. In this broad ranging interview, we cover his distinguished career, his opinion about the recent direct to consumer trends, and much more.