Few people are paid to be funny, or at least recognize funny. Jack O'Brien is one of them. He’s the Creative Director and Head of Comedy at the iHeart Podcast Network. O’Brien is also the cohost of The Daily Zeitgeist podcast along with Miles Gray. Before joining Stuff Media in 2017, which is now part of the iHeart Podcast Network, O’Brien launched the humor website Cracked.com in 2006 and was a driving force behind the site’s editorial and video content until he left to work in podcasting.