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Jason Barrett Is Doing It Big

“If you’re going to do something, you might as well do it big or don’t do it at all. It’s the same way I programmed a radio station; are we here just to talk and fill time, or are we here to maximize minutes?”

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It’s funny, looking back now. I once had a role in putting together a small event at a local radio station. I thought it’d be easy. It didn’t take long to notice that all of the coordinating, communicating, and moving parts were far more in-depth than I ever anticipated.

With that in mind, I don’t even want to know how many grease fires need to be attended to while piecing together the latest BSM Summit. It has to be like an IKEA project on steroids and HGH at the same time.

That’s one of the things I respect most about Jason Barrett; the guy doesn’t shy away from a challenge. The president of Barrett Sports Media holds an event that benefits the entire sports radio industry, regardless of the workload. How can you not admire that? He truly has a passion and a genuine love for the industry. If sports radio were a car on the side of the road, JB would either be pushing it or changing a tire like a NASCAR pit crew member.

NFL Draft analyst Bucky Brooks has a great saying that quarterbacks are either trucks or trailers; some guys carry a team while others are carried by the squad. It works the same way in sports radio. JB isn’t a guy who is carried by the industry; he’s got a trucker hat on.

JB also represents what the industry needs; sports radio needs people that look beyond what they can get out of it and instead focus on what they can put into it. Sports radio improves when people look to boost the format, not just their bank accounts.

The purpose of this interview isn’t about highlighting JB as the All-American guy. It’s about focusing on how the Summit can impact the mission to make sports radio bigger and better. JB and I also chat about the biggest difficulty he faces while putting the conference together and the impact of COVID on this year’s event. He also shares a few thoughts on radio’s greatest challenges and opportunities going forward. Enjoy!

Brian Noe: First off, why do you choose to run the event?

Jason Barrett: That’s a good question to start. I would say first of all, one of the biggest holes our industry has had for a long time is that every company is focused on what their strategies are, what they think is the best for reaching an audience, selling advertising, all of that.

But I remember I would go to these workshops and people would be in the room and everybody spoke the same language. I bonded with some people who thought like me. Everyone would be saying the key to this is teasing, playing the hits, and all the same bullshit we’ve heard forever.

But then I just listened to Tom Tolbert talk for 25 minutes about barbecuing and playing badminton in the backyard, and he kicked the shit out of me for three quarter-hours doing something that all of us in the room would’ve said is not playing the hits. Then I would listen to Mike Francesa not play sound, not tease, take an interview 40 minutes, and he’d be number one. I’d say, but the room I’m in, everybody said this is the path to be successful.

As you get more and more of those examples you just start to realize, there’s so much information out there, and so many people who succeed doing it differently, that I think you become smarter and more successful as a professional the more you surround yourself with other smart professionals. If I can learn one thing from an iHeart guy, an Audacy guy, a Bonneville, Beasley, and Hubbard guy, I’ve got five keys now in my tool belt that’s going to make me better at what I do.

On top of that, let’s face it, if you work in the business, we’ve all read about each other. We follow a lot of each other’s brands and we go, oh yeah, I heard the Hub is really good. You know what? Do you know why they’re good outside of one time you hit a stream button? What if you met some of these people?

I just looked at it as hey, I’m fortunate that we’ve built this up pretty well over the last six-plus years. You’ve been a big part of that Brian. In doing so, if we can use this platform to bring an industry together, to share ideas and information so we all get out of there with some things that will help us, that’s the goal.

I don’t forget that 80% of the country still listens to music. When we think about, oh, I’ve got to knock this sports station out, I’m like, no, you need them to thrive too. We’ve got four out of five people listening to a music station. We need to pull some of that over so we all win in a bigger way. That’s really the motivation for it.

Then beyond that, look, we all personally like to meet each other, spend some time, and enjoy two days. I think right now, coming off of what we’ve all just went through for the last two years, I think the industry could use it.

BN: What do you hope people gain from the event when they walk away?

JB: I think if there are three things, it would be one — the first and foremost — I hope you come out of there with information. If you don’t leave there in 16 hours of being in that theater with a few things that make you better, then you probably haven’t been paying attention, or you were just hanging out at the after-party getting smashed. [Laughs] That’s number one; I want people to learn something about the business.

Number two, I think it’s great for people to make relationships because those extend beyond the two days. People lose sight of this, Bri, you go to an event and you go, oh yeah, that’s that PD over there. I have no connection to that market. Then a year later, I’ll give you a perfect example, at the last Summit, Rod Lakin is presenting on stage for Phoenix. I’m sure a lot of people were like, oh, West Coast PD, Rod’s really sharp but I’m on the East Coast. What does that have to do with me?

Then all of a sudden, the news comes out two years later Rod Lakin’s now running WIP. I go, did you take time to say hello at the event? It’s always better to build a face-to-face connection because you have no idea where this business is going to take you in five years. The more friends you have, the more likely you are to continue working and the more of a network you have, the better it is to serve you.

If there’s a last takeaway beyond information and making relationships, I think the last part would be celebrating. It’s honoring people at the awards ceremony. It’s shaking someone’s hand who was on stage for a session and saying, hey man, that was really good.

We are all so competitive and we spend 52 weeks in a year trying to stay ahead of competition. We’re battling so many damn choices for the ear these days — or the eyes, we’re not just audio anymore. Sometimes it’s okay to say, hey man, this is a pretty cool damn business to be in.

If you were in L.A., holy shit, I met Colin Cowherd. He’s cool as hell. I went to New York; I met Craig Carton and Fred Toucher. These guys are highly successful personalities in the business. I think if we could celebrate our industry, give people some information, and at the same time, make a few connections, that puts everybody in a good spot.

BN: What’s the biggest difficulty you deal with when you’re putting a conference together like this?

JB: The biggest difficulty is literally being the organizer, executive producer, and host of it. I’m also the lead sales person on it. I’m also the one who goes down to the theater to talk to the manager and make sure the tech is going to be okay. I’m the designer of every image that you’re going to see on that stage, aside from those that I ask to create things because it’s part of their session. It becomes a bear putting the show together.

One of the things I’m proud of is that people see the final agenda and they’ll say, that’s damn good. What they don’t see are the people that I talked to that couldn’t be here. I talked to people for nine months. When I started, I was having dialogue with Mark Cuban because I thought we were going to do a virtual conference. Then literally, the event pivoted to being live and virtual. I knew, okay, I’m not going to be able to get Mark to fly in for this. So okay, we’ll cross that bridge down the road.

You go through a lot of those things because ultimately I look at it as this: if you’re going to do something, you might as well do it big or don’t do it at all. It’s the same way I programmed a radio station; are we here just to talk and fill time, or are we here to maximize minutes and create unforgettable moments? It’s the same with an event. I want people to walk out of there and go, that guy did a damn good job. He’s got a great team around him.

I couldn’t focus on this Summit if our website wasn’t fresh and the social wasn’t on point. In the past, I had to do that too; it doesn’t work. Now I’ve got people like yourself writing content, Demetri is scheduling social. People forget I have to do the top 20 at this time too, the biggest thing we do of the year, next to the Summit. You’ve got all of this going on and there is a reason why I’m up at seven and I go to bed at two.

I’ve got clients to serve but at the same time, I’ve also got to put on a kick-ass show. Otherwise, people aren’t going to find it valuable. If someone’s getting on a plane to come spend two days in a theater, and especially coming off of COVID and all of the stuff we’ve dealt with, I owe them the best experience possible. That’s what my focus is.

BN: What are your concerns related to putting on an event when COVID is still a part of our lives?

JB: Look, I’ll be honest — early January, I was terrified. I thought there was a possibility this would have to get moved back because Omicron started to rear its ugly head and everybody rightfully so was worried about their health and safety. As much as I like getting people together and celebrating the business, I don’t want people to leave here sick, exposing their family to stuff, so that was very much a concern.

New York in general, if you’re going to go to an event, you’ve got to be vaccinated. I knew that was one part of this, but people are vaccinated and have still gotten COVID. I can’t control what the world does.

I think one thing that’s made it a lot easier and the way I’ve communicated this to some around me has been, look, I get it, there are going to be some concerns for some people that maybe they’re not comfortable being in a theater. My answer to them is, well, then buy the virtual ticket. Don’t come. It’s okay, you’re not going to hurt my feelings if you can’t make it because I respect that. I don’t want anyone to feel uncomfortable being somewhere. If they feel that way, they should buy the virtual ticket and take it in that way.

I went to Madison Square Garden in January with my son. There were 15,000 people. Some had masks on, some had masks off. At some point you just say, look, as an adult I’m going to make a decision. I’m either okay being here or I’m not okay being here. I chose to go there. I wouldn’t have done that a year earlier. I did. I came out of it. I’ve been okay.

I flew out to Los Angeles for The Volume’s party. Shook hands, gave a few bro hugs, thought to myself, crap, this would be really bad if I came out of this party and got COVID a month before the Summit. But am I not going to support people who supported me? No, I have to do that. It’s the right thing for business. It’s the right thing for relationships.

I think if we can go to venues where there are 15,000 people and enjoy a sporting event, we should be able to go to a theater with 200 and get through it. I don’t promise anything because I know none of us are health experts. We’re trusting that the air around us is going to be okay and that we’re not in a bad spot. Everyone’s got to make that choice for themselves and if they choose to come or not come, I respect it either way.

There are different ways this time to enjoy the show. Those who are comfortable will be there, those who are not will go online and hopefully down the road, we’ll be in a spot where everyone’s comfortable being together.

BN: What’s the biggest fire you’ve had to put out in the past or just the craziest scenario you’ve encountered?

JB: Honestly, I’ve been lucky to dodge some major fires. Back in Los Angeles, we were scheduled to have Daryl Morey be part of the esports panel. I was really looking forward to that because I think he’s brilliant. He’s just got a really sharp mind for business.

On the morning of, I was notified that he couldn’t make it. They sent in his place their head of Clutch Gaming at the time when Daryl was with the Rockets, Sebastian Park. Now you know our audience, and Sebastian was great, but people want Daryl Morey.

Fortunately, that same morning I had connected with Eric Shanks. I hadn’t told people that Eric was going to be there because I wasn’t planning on him being there. He literally said I will come to the GRAMMY Museum to say a few words on behalf of Tony Bruno. When I took the stage to tell people I’ve got some good news and some bad news, Daryl Morey — and I heard the collective sigh — then I said but we’ve added FOX Sports President and CEO Eric Shanks, everyone went that’s pretty damn good.

I’ve been lucky to get through it but, look, it’s like when a band goes on stage, you can rehearse the songs, you could know what each other is supposed to do, what positions you’re supposed to be in, and then literally some roadie in the back knocks over a set of speakers that falls on the drummer and the whole show is changed. [Laughs] I’m lucky we haven’t had a roadie knock the speakers over yet.

But when you’re doing 16 hours of live programming, you’re always one step away from chaos. I pray that we’re not dealing with a major fire. It would be great if we could do this every year and not have one because once it happens, you just don’t want the building to burn down.

BN: What do you see as radio’s greatest challenges and opportunities going forward?

JB: First of all, the biggest opportunity is that audio listening is at a record high. Especially if you look over the last seven years, the growth of spoken word and listening is through the roof. There’s a lot of options out there for people.

I think that also presents the biggest obstacle. More people are creating content than ever before. More people are listening because of technology. We all have phones. We’ve got smart speakers. The opportunities to consume audio, everybody’s got earbuds in their ears, or they’ve got a phone nearby, or a computer, or if they’re in the car, the radio.

I think the real challenge — and what’s going to be interesting to follow in the next decade — is going to be the shift from the radio to streaming. We were already seeing it, but when you look at some of the rapid growth; I remember two years ago, and this is something I’m going to talk about at the show, Spotify CEO Daniel Ek had said radio is their biggest competitor. He’s interested in basically making sure linear dies. At the time — obviously as a radio guy, you’re a lifer like myself — you go, man, this is a great business, I don’t want to see linear die.

It’s not that it’s dying, it’s moving to different places. Whether it’s Pardon My Take being offered through podcasting platforms or through a terrestrial speaker, it’s still a show that we’re all going to enjoy and listen to. It’s just how you listen. The real challenge going forward is if that shifts, does the advertising shift with it? That’s going to be hard to replicate. We’ve been so dependent on the terrestrial model.

The other part of this is measuring it and finding it. Discovering where content lives is easy when you’re ESPN and you’ve got the world’s biggest reach and everyone knows they’ve got ESPN, ESPN2, ESPN+, or ESPN podcasts. You’re going to find them everywhere, but what do you do if you’re in a local market in Indianapolis, Kansas City, Salt Lake, how do you break through on the charts so people know your stuff?

At the same time, how do you turn those advertisers who’ve been spending money for the radio space and convince them to shift to a digital plan when you can’t even show the digital measurement the way you’ve shown radio measurement?

There’s a lot of things that are going to change. Who knows where we’re at in 20 years, Bri. Facebook became Meta. Pretty soon, we’re going to have artificial intelligence shows going on. This world is going to be crazy. I’m just glad that it’ll be my son’s problem to deal with in 20 years, not mine.

BN: I hear you, man. Do you have a final message you’d like to convey with the Summit set to begin?

JB: I’m grateful for everybody making the trip into New York. Especially thankful for the support we’ve had from our sponsors on it. This is the best year we’ve had with it and coming off of COVID, it’s really rejuvenated me to see that people care about their business enough to put their support behind It.

I just want people to come to New York, learn, laugh, have a good time, and ultimately walk out of there with some information to make their brands better. If we can accomplish that in 16 hours, I’ll feel we’ve done our job. Then we take a little reprieve before focusing on the next one.

Barrett Blogs

Would Local Radio Benefit From Hosting An Annual Upfront?

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How many times have you heard this sentence uttered at conferences or in one of the trades; radio has to do a better job of telling its story. Sounds reasonable enough right? After all, your brands and companies stand a better chance of being more consumed and invested in the more that others know about them.

But what specifically about your brand’s story matters to those listening or spending money on it? Which outlets are you supposed to share that news with to grow your listenership and advertising? And who is telling the story? Is it someone who works for your company and has a motive to advance a professional agenda, or someone who’s independent and may point out a few holes in your strategy, execution, and results?

As professionals working in the media business, we’re supposed to be experts in the field of communications. But are we? We’re good at relaying news when it makes us look good or highlights a competitor coming up short. How do we respond though when the story isn’t told the we want it to? Better yet, how many times do sports/news talk brands relay information that isn’t tied to quarterly ratings, revenue or a new contract being signed? We like to celebrate the numbers that matter to us and our teams, but we don’t spend much time thinking about if those numbers matter to the right groups – the audience and the advertisers.

Having covered the sports and news media business for the past seven years, and published nearly eighteen thousand pieces of content, you’d be stunned if you saw how many nuggets of information get sent to us from industry folks looking for publicity vs. having to chase people down for details or read things on social media or listen to or watch shows to promote relevant material. Spoiler alert, most of what we produce comes from digging. There are a handful of outlets and PR folks who are great, and five or six PD’s who do an excellent job consistently promoting news or cool things associated with their brands and people. Some talent are good too at sharing content or tips that our website may have an interest in.

Whether I give the green light to publish the material or not, I appreciate that folks look for ways to keep their brands and shows on everyone’s radar. Brand leaders and marketing directors should be battling daily in my opinion for recognition anywhere and everywhere it’s available. If nobody is talking about your brand then you have to give them a reason to.

I’m writing this column today because I just spent a day in New York City at the Disney Upfront, which was attended by a few thousand advertising professionals. Though I’d have preferred a greater focus on ESPN than what was offered, I understand that a company the size of Disney with so many rich content offerings is going to have to condense things or they’d literally need a full week of Upfronts to cover it all. They’re also trying to reach buyers and advertising professionals who have interests in more than just sports.

What stood out to me while I was in attendance was how much detail went into putting on a show to inform, entertain, and engage advertising professionals. Disney understands the value of telling its story to the right crowd, and they rolled out the heavy hitters for it. There was a strong mix of stars, executives, promotion of upcoming shows, breaking news about network deals, access to the people responsible for bringing advertising to life, and of course, free drinks. It was easy for everyone in the room to gain an understanding of the company’s culture, vision, success, and plans to capture more market share.

As I sat in my seat, I wondered ‘why doesn’t radio do this on a local level‘? I’m not talking about entertaining clients in a suite, having a business dinner for a small group of clients or inviting business owners and agency reps to the office for a rollout of forthcoming plans. I’m talking about creating an annual event that showcases the power of a cluster, the stars who are connected to the company’s various brands, unveiling new shows, promotions and deals, and using the event as a driver to attract more business.

Too often I see our industry rely on things that have worked in the past. We assume that if it worked before there’s no need to reinvent the wheel for the client. Sometimes that’s even true. Maybe the advertiser likes to keep things simple and communicate by phone, email or in-person lunch meetings. Maybe a creative powerpoint presentation is all you need to get them to say yes. If it’s working and you feel that’s the best way forward to close business, continue with that approach. There’s more than one way to reach the finish line.

But I believe that most people like being exposed to fresh ideas, and given a peak behind the curtain. The word ‘new’ excites people. Why do you think Apple introduces a new iPhone each year or two. We lose sight sometimes of how important our brands and people are to those not inside the walls of our offices. We forget that whether a client spends ten thousand or ten million dollars per year with our company, they still like to be entertained. When you allow business people to feel the excitement associated with your brand’s upcoming events, see the presentations on a screen, and hear from and interact with the stars involved in it, you make them feel more special. I think you stand a better chance of closing deals and building stronger relationships that way.

Given that many local clusters have relationships with hotels, theaters, teams, restaurants, etc. there’s no reason you can’t find a central location, and put together an advertiser appreciation day that makes partners feel valued. You don’t have to rent out Pier 36 like Disney or secure the field at a baseball stadium to make a strong impression. We show listeners they’re valued regularly by giving away tickets, cash, fan appreciation parties, etc. and guess what, it works! Yes there are expenses involved putting on events, and no manager wants to hear about spending money without feeling confident they’ll generate a return on investment. That said, taking calculated risks is essential to growing a business. Every day that goes by where you operate with a ‘relying on the past’ mindset, and refuse to invest in growth opportunities, is one that leaves open the door for others to make sure your future is less promising.

There are likely a few examples of groups doing a smaller scaled version of what I’m suggesting. If you’re doing this already, I’d love to hear about it. Hit me up through email at JBarrett@sportsradiopd.com. By and large though, I don’t see a lot of must-see, must-discuss events like this created that lead to a surplus of press, increased relationships, and most importantly, increased sales. Yet it can be done. Judging from some of the feedback I received yesterday talking to people in the room, it makes an impression, and it matters.

I don’t claim to know how many ad agency executives and buyers returned to the office from the Disney Upfront and reached out to sign new advertising deals with the company. What I am confident in is that Disney wouldn’t invest resources in creating this event nor would other national groups like NBC, FOX, CBS, WarnerMedia, etc. if they didn’t feel it was beneficial to their business. Rather than relying on ratings and revenue stories that serve our own interests, maybe we’d help ourselves more by allowing our partners and potential clients to experience what makes our brands special. It works with our listeners, and can work with advertisers too.

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BSM Writers

Brandon Kiley Doesn’t Pretend To Be Someone He’s Not

“There was a time where the audience probably said, this guy isn’t a St Louisan. But this is home for me now and I’ve adopted it.”

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There must have been something about Brandon Kiley that everyone saw as a young aspiring sports radio host. Nick Wright saw enough to bring him to Houston at SportsRadio 610 as an intern for a summer. Will Palaszczuk saw enough to urge him to apply for his old job in Columbia, MO at KTGR. Ben Heisler saw enough to know he’d fit perfectly with Carrington Harrison in afternoon drive at 610 Sports in Kansas City. 

Maybe you can chalk it up to Kiley being able to make such great contacts. Or maybe it’s just that he was supremely talented at a young age. Odds are it’s a combination of both. But he was destined to be a sports talk host somewhere, it just turns out he’s having success over the air in a city he never imagined he’d work in. 

A Kansas City kid, Kiley knew at 16 years old he wanted to be a sports radio host. He was even more sure of it when he started doing college radio at Mizzou. But it was in Houston where he got his real taste of what sports radio was like.

“I went to 610 in Houston for the morning show with Nick Wright,” Kiley said. “He basically just assigned me as an extra producer. We had known about each other through Twitter and I had a little bit of a relationship with him beforehand. I think he knew I was willing and able to take on more tasks than a typical intern would usually do. Essentially, I became an extra guest booker, cut audio for them, and came up with topics at night. It was like he had an extra producer for the summer and it was my first real experience doing something like that.”

Imagine the confidence he left Houston with as he traveled back to Columbia for another year of college at Mizzou. Few, if any, on campus could have claimed the kind of summer Kiley just had. He parlayed that experience into a once-a-week show at KCOU, the student radio station. The following semester, he pitched the idea of doing a daily show

“I told them I’d take any time slot available,” Kiley said. “The one that I got was the very glamorous 6-7 am time slot. There weren’t a whole lot of college kids that wanted to wake up that early every morning. I ended up having a rotating cast of co-hosts and it ended up being super valuable because I learned how to work with a lot of types of personalities.”

He excelled as a host and found his style behind the mic, and soon after, he got his first big break. In March of 2014, Will Palaszczuk contacted Kiley and told him he was taking another radio job outside the market. The two knew of each other, seeing as both were in Columbia and covering the same games in town. Palacsuk told Kiley he needed to apply for the spot he was leaving at KTGR.

“There was literally one sports station and one sports show in town and it was that one,” Kiley said. “I applied to him the previous semester and said, hey man, if you guys have anything available I would love to come work there. It just so happened he got a job elsewhere and he called me up and said, ‘Hey man, I don’t know what your plans are, I’m about to take another job and they’re going to post my job available. I don’t know if they’re going to make it a producer or co-host gig, but I think you should apply because I think you’d be good at it’. Will’s good work helped a ton in terms of me landing the gig. I graduated and told them I wanted to make it full-time.I was essentially a producer and co-host for the afternoon show. I never even applied anywhere outside of Columbia”

For two years, Kiley stayed at KTGR and covered the Missouri Tigers. He was fresh out of college and living in a college town doing what he loved in his early 20’s. It wasn’t a bad life. But one night in Columbia changed his entire professional career. It just so happened it occurred on the rooftop at Harpo’s, one of the most well-known establishments in town.

“My roommate at the time, we both worked at the radio station in Columbia,” said Kiley. “He worked at the hit music station and I worked at the sports station. We all went out one night at Harpo’s and he said, ‘Hey, I just want to let you guys know I’m getting out of radio and moving to Kansas City.’ I was like, oh shit, what am I going to do? Our lease was up in two months, so the timing worked out well and I was looking at Barrett Sports Media looking where I could go next.”

“My girlfriend at the time, now my wife, was from St. Louis and there was a job available there. I had always thought, that’s not a place I want to live, why would I ever want to live in St. Louis? They didn’t have a football team, it just didn’t seem like a great fit for me. But my buddy tells me he’s moving and I’m like, St, Louis it is! That night I ended up applying for the job and got a call back from Chris “Hoss” Neupert, who at the time was the PD here, and asked if I would be interviewed with him and Kevin Wheeler, whose show I would be producing.”

So off to St. Louis he goes. For three and a half years, Kiley embraces his new city and tries to work his way up at 101 ESPN. 

But the Kansas City kid felt a pull back to his hometown. Oddly enough, Ben Heisler even reached out to tell him he was leaving the station to pursue another opportunity in sports. It felt like the perfect time to pursue his dream of doing sports radio at the station he grew up listening to.

“I’m from Kansas City and grew up listening to 610 Sports Radio,” Kiley said. “A guy I listened to growing up was Nick Wright. I also listened to a bunch of Carrington Harrison, Danny Parkins and Ben Heisler. Those guys had what I consider one of the best shows in Kansas City sports radio history. I got to know them through Twitter and Heisler sent me a text. He knows I’ve always been interested in moving to KC. He tells me he’s about to get out of radio and into more fantasy football stuff and his job is going to come open.

“I had applied for multiple other jobs in KC over the years and had never gotten any real consideration. When Heisler left, I knew Carrington and thought this might work out. I ended up getting in contact with their PD Steven Spector and it felt like a real opportunity. I got what I considered to be my dream job, producing in the afternoons and hosting a Saturday show at 610 Sports. I thought, what could there be more in life than this? This is the best.”

But life happened and he had to make a decision around three months after moving to Kansas City.

“2-3 months later it became clear, it was going to be difficult for my girlfriend, now wife, to move to Kansas City with all of the family ties she had in St. Louis,” said Kiley. “It was the decision of, do you stay in Kansas City and chase the dream or do we alter the dream, in terms of the job, and see if there’s anything in St. Louis?”

He never thought his best years and most successful years as a sports radio host would come in St. Louis but they have. It’s a city he loves and he’s worked hard in hopes it will love him back. But he’s also not going to pretend to be someone he’s not. Though it can sometimes be hard for St Louisans to accept someone that’s not from there, Kiley doesn’t act like he attended World Series games in 1982, listened to Jack Buck growing up or watched Kurt Warner at the Edward Jones Dome. He’s himself.

“That wasn’t my love and I can’t pretend that it was,” said Kiley. “Have there been times, especially early on where that was a potential issue for me? Yeah it was. There was a time where the audience probably said, this guy isn’t a St Louisan. But this is home for me now and I’ve adopted it. It does in a lot of ways remind me of Kansas City, where if you take the time to know what the soul of the city really is, in terms of sports, I think people can appreciate and respect it.”

Kiley doesn’t hold on to his Kansas City roots on the air, in terms of the topics he talks about. He’s a Chiefs fan and even writes for Arrowhead Pride, but he’s not going to talk a lot about the Chiefs in a city that doesn’t have an NFL team. He’s also a Mizzou grad and talks about the teams on Rock M Nation, but again, he’s rarely, if ever, going to do several segments a day on the Tigers. Instead, he knows the audience wants to hear about the Cardinals. Blues talk is clearly next in line. Everything else falls down the order if not off of it completely. 

Kiley grew up watching baseball, so he can easily break down what issues the Cards’ offense may be having in the middle of May, but hockey was different. He didn’t grow up around the game and the transition to having in-depth conversations on the Blues was a more difficult task. 

“When I came here the first time it was during the middle of a Blues’ playoff run. At that time I was just plopped into this thing, and I didn’t know shit about hockey. I had probably watched about 10 hockey games in my entire life. I’m looking at Kevin Wheeler like, I’ve got to be honest I don’t have a lot on hockey I’m going to be able to help you with. If you could help bring me along with it, that would be great. Over the years I’ve been able to take it in. I used to host a show with Jamie Rivers, who’s a former Blues player. If you told me five years ago I’d be able to do that, much less enjoy doing that, I would have said you’re out of your damn mind.”

Whereas most sports radio shows in football markets are searching for content to help fill segments, this is one of the sweetest times of the year for Kiley and everyone at 101 ESPN. The Blues are deep in the playoffs and the Major League Baseball season is underway. His show BK and Ferrario covers it all every weekday from 11 am – 2 pm. 

Kiley never thought this would be his life, but he loves what he’s built in St.Louis and doesn’t give off the vibe he’s looking to leave anytime soon. He’s a great example of someone who didn’t pigeonhole himself into just one market. He was willing to look outside of his hometown and has found true success. 

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Will Middlebrooks Has Been The Breakout Star Of The Red Sox Season

“If I was going to work for an organization or a regional sports network, why not the Red Sox, for someone that I’m actually a fan of?”

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The Boston Red Sox experience in 2022 is just different. In every way.

The team has struggled out of the gate. They certainly aren’t the team that was two wins away from the World Series last year.

Fenway Park doesn’t even accept cash anymore.

But it’s not just that the Red Sox are different on the field or at the ballpark – they are different on television too.

When loveable, longtime Sox broadcaster Jerry Remy died in October 2021 at the age of 68, we knew that consuming the Red Sox on TV would never be the same.

There is no replacing Jerry Remy. One person can’t do it. No way.

And the fans know it.

The bosses at the NESN know it too. They haven’t tried to replace Remy on the broadcasts with just one person. 

In fact, they’ve brought in several new people to the broadcast team. A group of people just rotating in, giving viewers a different experience and a different perspective every night. 

They’ve added former Red Sox players Kevin Youkilis and Kevin Millar to the broadcast booth roster. They’ve added Tony Massarotti of 98.5 The Sports Hub as well.

And in the pre- and post-game studio, they’ve taken a similar approach, which is an extension of previous years, mixing and matching host Tom Caron with a slew of former Red Sox players including Jim Rice, Tim Wakefield, Ellis Burks, Lenny DiNardo, and former Sox infielder Will Middlebrooks, who will be in the studio for about 40 games this season.

I think that NESN has found a formula that works. It’s been fun and informative – and different. In a year that serves as a constant reminder of what’s been lost as a viewer, it’s refreshing to realize that these broadcast teams are giving you something gained.

A star is born.

When I mentioned to Caron that I wanted to write a piece on Middlebrooks, he said: “He’s a rising star.”

And it’s easy to see why he feels that way.

Will Middlebrooks is young (33), accessible, opinionated, active on social media, and he has the playing resume to legitimize his point of view.

But it took some real coaxing to get into the business in the first place. After a devastating leg injury ended his playing career in 2019, Middlebrooks was unhappy.

“I sat around and sulked and was angry about it for about three months,” he said. “And my wife, Jenny (Dell), finally said, ‘You need to get off your butt and do something, find not just, work, but find something you’re passionate about again.’”

He didn’t know at that time that he was passionate about media work, but Dell, who works for CBS Sports, volunteered him to do a show at CBS Sports HQ in Ft. Lauderdale, near where their family resides.

“She said, like it or not, you have a show in three days. You’re going to try it out, and if you’re good at it, they’re going to hire you,” he recounts of their conversation. “I was like, I don’t want to do it. I’m not ready to talk about baseball. I hate baseball right now. I just have such a bad taste in my mouth from everything that happened over the past year.”

But that didn’t deter Dell from pushing her husband to take the chance.

“She said, well, I don’t care. I already told them that said you would do it,” he says. “So she kind of threw me to the wolves, but for the best. And I went in and I gritted my teeth and just got it done and then talked baseball. I did it a couple of more times and they said, ‘Hey, you’re decent at this. We’re going to hire you on for a year!” “And here we are, I’m four years into it,” he joked.

And over those four years, Middlebrooks has ballooned into one of the most recognizable follows for baseball fans. In addition to working at NESN and CBS Sports, he’s also one-half of the Wake and Rake podcast, has appeared on ESPN Radio, has done color commentary for college baseball, and has more than 155,000 Twitter followers.

Resonating with Boston 

When I ask Middlebrooks about landing the NESN gig for 2022, he beams through the phone. He says he wanted the challenge of working in Boston and he welcomed the opportunity to expand his media footprint.

It’s evident that he loves the Red Sox – and the city of Boston. How couldn’t he? He made his Major League debut with the organization, played parts of three seasons with the team, won a World Series with the Sox, and met his wife in the city.

“If I was going to work for an organization or a regional sports network, why not the Red Sox, for someone that I’m actually a fan of?” he said. 

While it’s clear that Will loves Boston, and it’s clear why NESN loves him, what needs more unpacking is the attachment that the Red Sox fans have to him considering he spent just those three seasons there and doesn’t live in New England full-time. 

Middlebrooks can’t quite figure out why the people of the region hold him so close, but he does have a good hypothesis.

“I think that if I left anything, it was people saying, ‘well, he played hard. He gave everything he had,’ he said. “And I know that’s really important in Boston, just the blue-collar mentality of ‘keep your head down, work, play as hard as you can, even if things aren’t going well, just bust your butt and be a good teammate and all that.’”

But there just may be something else at play.

“I think a lot maybe had to do with when the marathon bombings (2013) happened…I’m pretty outspoken on social media about that stuff and with my teammates, we all rallied around each other,” he said. “I think I was just lucky enough to be a part of a team that was really special to everybody in Boston. So they embraced me after that.”

The Family Dynamic 

Dell has been in sports media for more than a decade as a host and sideline reporter for CBS and NESN before that. She knows the business and its nuances. She understands when and how to look at the camera and when and how to ask questions of athletes. She knows the expectations of her husband’s current employers. She’s undoubtedly a great resource to have.

But as Middlebrooks finds his own footing in the business, and as his star grows, what is that dynamic like? She has the answers to the tests already, but how does he balance using that resource versus figuring things out on his own?

“I’m very open to anything she has to say,” he said. “I’ll come out of my office, like, ‘Hey, that was pretty good!’ And she’s like, ‘Yeah, it was good…but…”

“She always has something, and at first it used to really annoy me, because I’m like, man, I thought I was doing really good,” he said. “And she’s like, ‘No, you are doing good. I’m just trying to help you get to that next level. There are just little things here and there that you don’t know.’ And as a competitor, it’s really frustrating. But you know, after a couple of minutes I walk away, I’m like, you know what? I’m really appreciative to have that access to someone that can help.”

What’s Next?

At such a young age with such already vast experiences, it seems plausible that even bigger media steps could be in play for the former infielder. I asked him if he has a goal he’s working towards. Sunday Night Baseball? The MLB Network? Something else?

“One thing I’ve really learned is to not look too far down the road and kind of just live in the moment and enjoy the moment,” he said. “I’m really happy with being with with CBS and with NESN, and within that umbrella, of course, I would like to grow. Does that mean in the booth? Does that mean more games pre and post? Sure I’m up for anything where they want me, because what I’m doing right now, I feel like is a dream job outside of playing and I’m so happy with it.”

Middlebrooks has been on the NESN broadcasts all week and will continue through this weekend as the Red Sox host the Mariners in a four-game series.

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