T-Bob Hebert spent eight years building a radio career in Baton Rouge. When his contract came up at 104.5 ESPN, he knew what he wanted to make. The station had a different number in mind.
Hebert pitched what he thought was fair compensation for morning drive. Guarantee Media, which owns 104.5, runs one of the few radio operations in the country that’s actually thriving while the industry collapses everywhere else. They have full staffs. They pay well. But they weren’t going to meet Hebert’s ask.
The station told him that if he could find better, go ahead and look. So at 36 years old with three young kids, Hebert had a decision to make. He could stay in Baton Rouge and be happy. Or he could take what might be his last real shot at something bigger.
“You feel the weight of time,” Hebert said on the Awful Announcing Podcast. “And OK, if I’m gonna take a shot, contract up, 36 years old, three kids that are young… this is kind of maybe the last opportunity to take a big shot.”
Hebert had built relationships with Big Cat (Dan Katz) and others at Barstool over the years. Two people who’d been on his show had already made the jump. Megan Making Money (Megan Nunez) was a gambling contributor on Off The Bench before going to Barstool. Same with Ben Mintz. They’d both made the move from being on his show to working at Barstool. The path was there if he wanted to take it.
He talked to his wife first. They agreed that once they started down this road, if Barstool said yes, they had to be willing to take it. The opportunity wouldn’t come again.
Then one morning at the station, something minor happened. Hebert described it as a “minor annoyance,” the straw that broke the camel’s back. Whatever it was, it pushed him to finally send the text.
He texted Dan Katz. Here’s what I’ve done, here’s my résumé, I host a daily show in Baton Rouge. Hebert laid out his experience and made his case. He told Katz he’d work his ass off. It was the standard pitch you make when you’re trying to convince someone to hire you.
Katz texted back interested. That response started a process that would stretch across multiple months. Barstool was coming to town for the Super Bowl that February. Hebert got a chance to meet Dave Portnoy face-to-face during that trip. It wasn’t a formal interview, just a chance to get in front of the founder and make an impression.
From there, it was the usual back-and-forth of contract talks. Little interactions here and there as both sides figured out if this could work. Hebert was still hosting mornings in Baton Rouge while all of this played out in the background. Eventually, Barstool made him an offer he couldn’t turn down.
Hebert announced in May that he was leaving Baton Rouge for Barstool’s Chicago office. His final show at 104.5 aired May 16. He’d spent the last four years co-hosting Off The Bench with Jacob Hester.
Here’s what Hebert didn’t know during any of that process: Barstool was launching a morning show on FS1.
He walked into the Chicago office on his first day with show ideas ready to pitch. Digital content he wanted to create. Concepts he’d been working on. Then, Big Cat called him into his office.
“I have, like, all these pitches ready to go in terms of like shows I can do and what I want to do,” Hebert said. “And I get called into Dan’s office, and he’s basically like, ‘Hey, you know, we’re kind of working on this FS1 show, and we think you’d be a good fit for it.'”
The FS1 deal was still being finalized when Hebert arrived. Fox and Barstool were in the middle of hammering out the details. But Katz told him they wanted him for it. Hebert had walked in ready to pitch digital shows. Instead, he was being offered a seat at the table for a national morning television program that didn’t even exist yet. He’d spent months negotiating what he thought was a digital media job. He’d moved his wife and three kids from Louisiana to Chicago for podcast and video work. The entire time, Barstool and Fox were working on the TV deal. Nobody told him until he walked through the door.
“I mean that, that’s the sort of pinch myself sh*t where it’s like you can’t help but be grateful and and and just recognize how lucky you are that sh*t’s breaking your way,” Hebert said. “That you walk into this new job, and on day one, when I wanted to pitch a morning show, they’re like, ‘ Oh, actually, we have a morning TV show that we think you’d be good to host. Like that’s insane.”
Wake Up Barstool premiered Sept. 2 on FS1. The show airs 8-10 a.m. from Barstool’s Chicago headquarters. Hebert told Barrett Media in August he’d be on the show “most days.”
Hebert brings college football expertise to the show. He was an offensive lineman at LSU before getting into media. His father, Bobby Hebert, was a quarterback at LSU and later in the NFL, including with the New Orleans Saints. The younger Hebert spent 13 years in local radio before Barstool.
“But no, I had no idea. I had no idea about it until my first day of work,” Hebert said. “And maybe that’s why they hired me, you know. I don’t know. I don’t know. But, again, it’s just, f*ck, it’s just lucky man. It’s just crazy, crazy, crazy lucky.”
Listen to the full episode of the Awful Announcing Podcast featuring T-Bob Herbert beginning Thursday, Jan. 22. Subscribe to the show on Apple Podcasts, Spotify, and wherever you get your podcasts. For more content, subscribe to AA’s YouTube page.
About Sam Neumann
Since the beginning of 2023, Sam has been a staff writer for Awful Announcing and The Comeback. A 2021 graduate of Temple University, Sam is a Charlotte native, who currently calls Greenville, South Carolina his home. He also has a love/hate relationship with the New York Mets and Jets.