In episode 11, Kevin chats with Emily Kaplan, who's covered the NHL for ESPN since 2017. In addition to breaking news and writing about hockey, Kaplan is the between-the-glass reporter for ESPN's biggest games, interviewing the star of the game afterward. Before becoming one of the preeminent voices in the hockey world, Kaplan got her first job at Sports Illustrated, covering the NFL at the MMQB. She'll share how she got her way to SI from internships at the Boston Globe and Philadelphia Inquirer, the impact of her dad on her interest in hockey, and how Peter King's mentorship helped set her up for success. Hear how Emily Kaplan broke in.

In episode 10, Kevin chats with Mark Potash, who has spent 38 years as a sportswriter at the Chicago Sun-Times. Before he helped chronicle the Bulls dynasty, covered the Blackhawks Stanley Cups and worked on the Bears beat, Potash was a college student covering Marv Levy's Kansas City Chiefs. Then he was off to Little Rock, Arkansas, where he covered high school sports. The 2024 Illinois Sportswriter of the Year is full of stories about covering sports in the '80's. Hear how Mark Potash broke in.

In episode 9, Kevin chats with Paul Pabst, executive producer of The Dan Patrick Show. "Paulie," as he's known on the show, has worked with Dan Patrick dating back to 2002. As the show has taken off, with its simulcast on Peacock, Pabst has been everywhere from Super Bowls to Final Fours to even an upcoming episode of "Family Feud." He's been in sports media for more than 30 years, getting his start at the same place as Kevin — Pro Football Weekly. A chance meeting in a New York City bar helped land Paul his first radio job, and soon he was working with Jim Nantz before heading to ESPN. Hear how Paul Pabst broke in.

In episode 8, Kevin chats with Mirin Fader, senior staff writer at the Ringer and the New York Times best-selling author of “Giannis” and “Dream,” her latest book on the life and legacy of Hakeem Olajuwon. Fader has become one of the country’s preeminent sports profile writers, and she got her start writing several stories a week for the Orange County Register. Mirin discusses the work ethic that went into that job, the difficult conversations with editors, and how she persevered in a tough industry to keep going after her goal of writing meaningful sports stories. Hear how Mirin broke in.

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.

In Episode 4, Kevin chats with Jayson Stark, the 2019 BBWAA Career Excellence Award winner and 2024 National Sports Media Association Hall of Fame inductee. Jayson, who hosts the "Starkville" podcast, has been covering baseball since 1979, including stints at the Philadelphia Inquirer and ESPN. Long before he was on "Baseball Tonight," Jayson was a news reporter at the Providence Journal, covering city hall meetings. This is how he broke in.