Watch How to Make It in America Season 1 Episode 1. Pilot Episode. I wasn't sure what to expect going into the first episode of How to Make It in America. I guess I was looking for a sort of Entourage-like series that it was being marketed as. And it was. Dozens of similarities could be drawn between How to Make It in America and Entourage, but here's the difference: lack of Ari Gold notwithstanding, America is funnier than Entourage.