Cracked Editor-in-Chief Jack O’Brien joins Adam for a repeat Wolf Den appearance. On his first time guesting (episode #32 in 2011) Jack met Jeff Ullrich for the first time, and didn’t even have a podcast yet. Now he hosts the Cracked Podcast, a successful Earwolf show.  Jack explains how he became Cracked’s Editor-in-Chief and then the host of that podcast. He also reveals the user-focused strategy behind Cracked’s addictive and shareable articles and how that style gets translated to popular video and podcasts. They wrap up by discussing the similarities between podcast ads and branded content, and why honesty is an important factor for both.