In episode 7, Kevin chats with Courtney Cronin, who has covered the Chicago Bears for ESPN's NFL Nation since 2022. Prior to that, she was ESPN's Vikings reporter starting in 2017. Cronin also has appeared on — and hosted — "Around the Horn," which will have its final show this week. She hosts a weekly national radio show on Sunday mornings on ESPN while also appearing locally on ESPN 1000. Before she was all over the airwaves, Cronin got her start in Jackson, Mississippi, as a video journalist for the Clarion-Ledger covering the top recruits in the area. Her story of persistence and patience in getting that first job, and the fearlessness she learned in Mississippi, has helped lead her to ESPN. Hear how Cronin broke in, and, before it leaves the air, what "Around the Horn" has meant to her.

In episode 6, Kevin chats with Bruce Arthur, who’s been a columnist at the Toronto Star since 2014. He was named the sports writer of the year by Sports Media Canada and his work was included in the 2023 edition of “The Year’s Best Sportswriting.” Arthur has covered the NBA, NHL and nine Olympics, along with covering the COVID-19 pandemic starting in 2020 when sports shut down. Before Arthur was profiling Blackhawks star Conor Bedard, he wasn't sure what he was going to do in life, and got his journalism start at a college paper … when he wasn’t yet enrolled in that college. This is how he broke in.

In Episode 5, Kevin chats with David Aldridge, senior columnist at the Athletic and 2016 winner of the Curt Gowdy Media Award from the Naismith Memorial Basketball Hall of Fame. Before he began his 30 years covering the NBA, David got his start at the Washington Post as a general assignment reporter, and then on the Baltimore Orioles beat. Hear why he calls his career "preposterous" and how he broke in.