Will Cain has made a career out of saying what he really thinks, and this conversation was no different. We talked about faith, family, and the power of conviction in a world that constantly demands you choose a side. Will shared how growing up in Texas shaped his worldview, what he learned from leaving ESPN for Fox News, and why he believes truth and empathy can still coexist in today's media landscape. We also discussed marriage, fatherhood, and the importance of raising boys who are strong, kind, and grounded. Will opened up about the pressure that comes with public life, how he handles criticism, and what it means to lead with both humility and courage. This was real and unfiltered, an honest look at what it means to hold onto your values when the spotlight never turns off. BTS on Patreon: http://bit.ly/4nLmOSk Chapters: 0:00 Intro 4:04 Life as a Cowboy in Montana 12:19 The Sudden Passing of Will Cain's Father 16:04 Mental Health 18:52 Will Cain's Upbringing 23:44 Will Cain's Early Days on TV 28:55 Will Cain Was in the Quinceañera Business? 33:28 Will Cain's TV Pilot 35:44 First Time on TV 42:11 When Sage Met Will Cain at ESPN 49:18 Skip Bayless Story 51:56 Lessons Learned at ESPN 54:01 Will Cain's Time at CNN 1:02:03 When ESPN "Turned" 1:11:55 Charlie Kirk 1:14:13 Hope for ESPN? 1:19:03 Second Attempt at a "Lip Pillow" 1:23:20 Fox & Friends 1:26:28 Hawaii 1:33:01 Relationship with Pete Hegseth 1:35:24 Is Fox News Propaganda? 1:38:12 Moving Back to Texas Learn more about your ad choices. Visit megaphone.fm/adchoices
