Cowboy Ventures' Aileen Lee on pioneering diversity in tech & VC, lessons from backing winners | E988

Jason Calacanis chats with Aileen Lee about her journey from MIT to San Francisco, her experience at GAP during the internet's early days, and working under Mary Meeker. They discuss the appeal of WeWork to early investors, the market's growth bias, and SoftBank's role in increasing valuations. Aileen shares her involvement with Dollar Shave Club, her time at Kleiner Perkins, and the launch of Cowboy Ventures. They also touch on the diversity issue in tech and All Raise's current projects.