00:00 Fresh eyes, rare yeses and startup reality 00:45 Welcome to Alexandra Wilkis Wilson 02:25 New York childhood and Cuban roots 03:43 Girls, ambition and the lessons of sport 09:30 Building Gilt and daily shopping habits 14:08 GlamSquad and the on-demand economy 19:40 Why shared experiences matter 20:47 AI styling and the move into Allergan 24:55 Partnering with Lisa Myers and raising a fund 28:58 From founder to investor 31:10 Wellness through a consumer-investing lens 33:44 Wellness events and community 36:29 Better-for-you beverages 37:32 Founder advantage and Smash Kitchen 39:38 Racket sports: the limits of watch data 42:13 An early sports-data demonstration 48:08 Closing advice for young women