E297 - Ep. 296: From a Wisconsin Bedroom "News Set" to Podcast Empire: Richard Wilmore on Rosie O'Donnell, Coming Out & Building a Media Career

Richard Wilmore grew up in a tiny town at the top of Wisconsin, so far north he says people mistake Green Bay for "northern." He knew he was different by grade school, though he didn't come out until his twenties at UW Milwaukee, where a big, macho freshman-year roommate turned out to be entirely unbothered by it.

The real turning point came in the summer of 1997, when a 12-year-old Richard stumbled on a rerun of The Rosie O'Donnell Show and instantly rewired his life plan from elementary school teacher to talk show host. He describes the show's...