Former NFL quarterback Jay Cutler has called on a former Barstool Sports executive to help lead his new media brand.
Deirdre Lester is set to become the CEO of Outsider, a lifestyle company focused on sports culture. She was the chief revenue officer for Barstool and helped that company expand to over $200 million in revenue.
Cutler co-founded Outsider with entrepreneur Shannon Terry in 2020. The Nashville-based company employs more than 50 people full-time and continues to secure capital funding.
Lester told Front Office Sports the brand already has some podcasts in the can, including one hosted by ESPN’s Marty Smith (also a partner in Outsider), with plans to offer more unique content tailored to their specific audience.
“We will be producing more content shows that really speak to a variety of different areas of American entertainment and American culture that we feel have a theme of commonality – and embrace that Outsider mindset,” she told Front Office Sports’ Michael McCarthy.
Right now, the focus of content will be on NASCAR and country music, areas Lester says are key interests for their audience.
“We’re going deep on NASCAR in a way that a lot of the other sports media companies don’t,” she said. The company will also develop content centered on the outdoors.
Cutler will have a presence behind the microphone and in front of the camera, Terry said.
“He’s a one-liner extraordinaire. He’s really funny, and he’s interesting. At the end of the day, he’s memorable,” Terry said. “You may like him or you may dislike him, but he’s memorable. So he’s definitely going to help us on the media side.”
Jordan Bondurant is a features reporter for Barrett News Media. He also works for ABC8 News and Newsradio WRVA and 910 The Fan in Richmond, Virginia. His prior experiences include working for the Richmond Times-Dispatch, the Danville Register & Bee, Virginia Lawyers Weekly and iHeartradio Richmond. He can be reached by email at Jordan.E.Bondurant@gmail.com or follow him on Twitter @J__Bondurant.
Big Cat: Listening to ESPN Wisconsin After Packers Playoff Loss ‘Highlight of My NFL Season’
“For three hours, I sat in my car. I arrived home –it’s a 20-minute drive — I arrived home, and I sat for three hours listening to callers be like ‘blow up Lambeau!’, ‘get 12 (Rodgers) outta here!’, ‘we need to build a dome, this team isn’t built for the outside’, and that was the highlight of my NFL season. And I have no problem saying that.”
During a recent interview with Barstool Sports, Packers quarterback Aaron Rodgers had a poignant question for noted Chicago Bears fan Dan “Big Cat” Katz that he then used to slam the Packers quarterback while also expressing his enjoyment for Green Bay fans.
“Is it hard, for you as a Bears fan, that some of your greatest moments are cheering against me when the Bears aren’t playing?”, the Packers quarterback half-jokingly asked.
“Very good question,” Katz responded. “No, it’s actually great, because what I’ve told everyone is — I’m very realistic about the Bears — ‘not a great franchise, (the Bears) just don’t do the right things’ for the most part. Every year I look forward to the playoffs and the game that you’re going to lose. I’ve told this story on air, but, when you guys lost to San Francisco this year we were watching the game in New Jersey and I drove back to Brooklyn — brag — and I listened to (Mark) Tauscher. For three hours, I sat in my car. I arrived home –it’s a 20-minute drive — I arrived home, and I sat for three hours listening to callers be like ‘blow up Lambeau!’, ‘get 12 (Rodgers) outta here!’, ‘we need to build a dome, this team isn’t built for the outside’, and that was the highlight of my NFL season. And I have no problem saying that.”
Rodgers laughed at Big Cat as he delivered the message, seemingly getting genuine joy out of the conversation.
“I know I’m a loser,” Katz continued. “That’s the best part. I’ve come to grips with the fact that I’m a loser, so yes, watching you lose in the playoffs is…that’s my Super Bowl. And I’ve won a lot of Super Bowls if you do it that way. More than you.”
Michael Silver Joins San Francisco Chronicle
“I’m ecstatic to join forces with some of my favorite journalists and be part of a publication I’ve been devouring for decades — in the greatest region on Earth,” Silver told The Chronicle.
Veteran NFL reporter Michael Silver is joining The San Francisco Chronicle as their newest NFL columnist.
Silver will continue his work with The Volume, Bally Sports, and Backstage Media in addition to adding a column with the Chronicle.
“I’m ecstatic to join forces with some of my favorite journalists and be part of a publication I’ve been devouring for decades — in the greatest region on Earth,” Silver told The Chronicle. “It will be a thrill to write columns alongside Scott Ostler, a living legend, and my amazingly talented friend Ann Killion, who I’ve dreamed of working with since we were competing on the 49ers beat in the early ’90s. … As a native San Franciscan, this feels like home.
Silver has previously written for Sports Illustrated, Rolling Stone, GQ, NFL Network, and Yahoo! Sports, among others. He’s also authored books on Jerry Rice, Kurt Warner, and Dennis Rodman.
Skip Bayless Tries to Win Debate Rounds ‘Like Muhammad Ali’
“I must admit I have been known upon rare occasion to try to win a debate the way Ali won rounds with a flurry at the end trying to get the last word also going through the stop or wrap sign.”
When people watch debate shows, they sometimes don’t want the debate to end. However, bills have to get paid and commercials have to be shown. However, when is the right time for a debate show to air a commercial? On the latest episode of The Skip Bayless Show, Skip was asked in an email by a listener about when he and Shannon Sharpe know to go to a debate on UNDISPUTED on FS1. Bayless said the show has more room to roam in the first two hours, but eventually, he gets the signal from his line producer.
“We loosely plan on 22-23 minutes in what we call our A block. We block out 25-ish minutes for our B block, which is the only block in the show that has two topics in it.”
“Our line producer in the control room, Nick, who is in our ears. He tries to sense along the trail when we are winding down or when we are trying to push the clock too far. His first cue to us in our ears, he tries to avoid speaking when we are speaking, the first cue is ‘start to wrap’. Then, a minute or so later, he says ‘wrap’. If we continue to not wrap, maybe we get a much stronger ‘wrap’.”
However, it might not be easy for Bayless and Sharpe to end the debate, especially if they both want to be the one who wins the argument. So, sometimes, they can easily go past the hard wrap sign that is given.
“Sometimes the guy sitting across from me at the debate desk gets all worked up and barrels right through that stop sign. I must admit I have been known upon rare occasion to try to win a debate the way Ali won rounds with a flurry at the end trying to get the last word also going through the stop or wrap sign,” said Bayless.
If there is one thing that Bayless is proud of, it’s the fact that UNDISPUTED has never gone past the allotted time, which allows The HERD with Colin Cowherd to begin on schedule.
“I must tell you not in 6 years have we ever not finished a show right on time. Not once have we pushed Colin over the cliff as he begins his show. That is just not acceptable.”
Ricky Keeler is a reporter for BSM with a primary focus on sports media podcasts and national personalities. He is also an active podcaster with an interest in pursuing a career in sports media. You can find him on Twitter @Rickinator555 or reach him by email at RickJKeeler@gmail.com.