In episode 19, Kevin chats with Bryan Curtis, an editor-at-large at The Ringer and co-host of the media podcast, "The Press Box," one of the podcasts that helped inspire this one. Curtis got his start as an intern at the New Republic before heading to Slate. He then got an opportunity to write the media column for Play, a magazine inside the New York Times. Curtis discusses how he got comfortable writing columns about sports media, a special article he wrote about his grandfather playing softball, and how "breaking in" to media has — or hasn't — changed over the years. Hear how Bryan Curtis broke in.

In episode 18, Kevin chats with Jori Epstein, who has covered the NFL at Yahoo since 2022. Prior to that, she worked for USA Today with a focus on the Dallas Cowboys. She won the Terez A. Paylor Emerging Writer Award in 2022 as voted on by the Pro Football Writers of America, recognized as a rising star in the industry. Epstein's origin story begins at the University of Texas. Learn about the unique way she covered Longhorns football, her experience interning at Sports Illustrated, and how she managed the night shift at her first job at the Dallas Morning News. Hear how Jori Epstein broke in.

In episode 17, Kevin chats with Adam Rittenberg, who has covered college football at ESPN full-time since 2008, but has been affiliated with ESPN dot com dating back to an internship in 2001. Rittenberg's journalism career even dates back to his youth, when he worked for a children's news service as an 11-year-old. Rittenberg details what ESPN.com was like in the early days, how he got his start at the Daily Herald in Chicago, and what he tells his journalism students. Hear how Adam Rittenberg broke in.

In episode 16, Kevin chats with Jimmy Traina, a longtime writer at Sports Illustrated and host of “SI Media with Jimmy Traina.” Traina’s podcast helped inspire the one you’re listening to now, as he has interviewed some of the biggest names in sports media about their career journeys. As someone who covers sports media, Traina has unique insight into the industry, and tells the story of his start, from recording score updates for “SportsPhone” to how his popular column “Hot Clicks” began. Hear how Jimmy Traina broke in.

In episode 15, Kevin chats with Michele Steele, who does it all for ESPN, from reporting at big events to being in-studio at ESPN anchoring SportsCenter. The path to what has been a decade and a half at ESPN began as a business reporter. Steele discusses her college journalism career and where it took her, her first job at Bloomberg and how she got on the Tiger Woods beat, which ultimately led to ESPN. Hear how Michele Steele broke in.

In episode 14, Kevin chats with Tyler Kepner, who has covered Major League Baseball for more than 30 years, dating back to when he made a baseball magazine out of his house as a high schooler. Kepner, who has authored "K: A History of Baseball in Ten Pitches" and "The Grandest Stage: A History of The World Series" covered baseball for the New York Times from 2000-23. His origin story begins with that magazine, which opened doors with his hometown Phillies, before he got his first professional job covering the Angels, and then the Mariners. He tells those stories, and what he learned from writing about some of the biggest names in baseball. Hear how Tyler Kepner broke in.

In episode 13, Kevin chats with Adam Amin, the voice of the Chicago Bulls on Chicago Sports Network, and a play-by-play broadcaster for Fox doing NFL and Major League Baseball. Amin was voted the 2021 Illinois Sportscaster of the Year. A graduate from Valparaiso, Amin discusses how he first got into broadcasting before taking his first job at a radio station in Spirit Lake, Iowa. Amin reflects on what he learned from that challenging experience, how he got his first minor league job, and how that led him to ESPN. Hear how Adam Amin broke in.

In episode 12, Kevin chats with Vinnie Goodwill, senior reporter at Yahoo covering the NBA. He's been there since 2018, following a few seasons covering the Bulls at NBC Sports Chicago. Vinnie got his start on the NBA beat with the Pistons at the Detroit News, and he describes his origin story as a "villain" origin story. He battled some doubters in his efforts to move from freelancer to full-time beat writer. Learn about the English teacher who set Vinnie on the path to journalism, what "agate" is, and an angry Richard Hamilton. Hear how Vincent Goodwill broke in.

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.