Josh and Derek dig into money, success, and what people should do once they’ve “made it,” unpacking why hoarding wealth feels broken and why giving back should be part of the endgame. That spirals into Josh teasing his upcoming 40th birthday roast, which promises radical honesty, emotional casualties, and zero safe words.
From there, the conversation swings to fantasy football championship chaos, league ethics, and the urgent need for a proper trophy or belt, plus a truly cruel loser punishment involving Packers gear. The episode closes with music documentary talk, a very casual Christina Applegate sighting in Laurel Canyon, Counting Crows discourse, and half-serious plans to hit a bowl game or rivalry matchup in the future.
Equal parts reflection, rivalry, and unearned confidence. Just how we like it.
