Can Richard Dickson, the newly empowered C.E.O. of Gap, succeed where every other leader has failed by cleaning house? “That’s the only thing that can save the company,” says one former executive. “Fire everyone and bring new people in.”

Mickey Drexler, the legendary merchant and former impresario of Gap, J. Crew, Ann Taylor, and more, is now the chairman of Alex Mill, which operates off of his own personal investment. We chatted while Mickey was on vacation—because you’re never really on vacation when it’s your money on the line.