Sierra and Shan's former classmate and 30 Rock Soulmate Jacob Inman is on the freaking pod! He gives us a wonderful peek into the artistic and personal joys he's found in Chicago, the liberation of breaking the mold you've been put in by making your own creative work, and helps us bring back everyone's favorite type of hat. Jacob also shares his deep dive into ancient Roman Dynasties and fascination of the suppressed and powerful women of the era. Plus, we brainstorm a couple of new catchphrases for the show.