How to Make It in America ★ back for season two After a quick teaser trailer, HBO’s How to Make It in America is back for season two with Ben Epstein and Cam Calderon looking to bring their new clothing brand to today’s competitive market. This season sees the return of Kid Cudi as Domingo Dean as well as the ventures by all of the characters. Expect appearances this season from Pusha T, Javier Nunez and Pharrell Williams, and be sure to tune into the show starting October 2 at 10:30 p.m.