Mike and Jeb discuss the struggles that a lot of young men face today trying to come to terms what it means to "be a man" in today's culture. Speaking mainly on the discussions put forth by Prof Scott Galloway as well as Mike Rowe and Jonathon Haidt, the episode revolves around social media, following your passion vs purpose, and how Machiavellian manipulators are coopting the ideas of masculinity to take advantage of young men who feel lost.

Mike and Jeb go deep into their own pasts and how their upbringing shaped their ideas on money and how those ideas can change with more transparency and honest conversations.