In this episode of The Uncomfortable Chat, host Steve Wheatcroft interviews former NFL head coach Jay Gruden. They discuss Gruden's journey from a sports family to coaching in the NFL, his experiences with the Washington Redskins, and the challenges of motivating players. Gruden shares insights on the stress of coaching, the treatment of retired players in the NFL, and the importance of mental health for athletes transitioning out of sports. The conversation concludes with a fun segment of rapid-fire questions, revealing Gruden's personality and humor.