Media in Minutes

The Long Game: Sustaining a Career in Sports Journalism with Ian Casselberry

• Angela Tuell • Season 5 • Episode 18

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Ever wondered what it takes to carve out a sustainable career in the ultra-competitive world of sports journalism? Yahoo Sports breaking news writer Ian Casselberry pulls back the curtain on his remarkable 15-year journey through some of sports media's biggest names.

Casselberry's path defies conventional wisdom. Starting with a personal blog while at the University of Iowa, he gradually gained recognition from established publications like the Detroit Free Press before landing roles at SB Nation, Bleacher Report, Sports Illustrated and now Yahoo Sports. His story offers a masterclass in persistence and adaptability in an industry where traditional career ladders have largely disappeared.

What truly sets Casselberry apart is his ability to maintain genuine passion for sports despite the daily grind. "I do still love sports," he shares. "That is the fuel, that is the juice... what gets me going on writing." This authentic enthusiasm shines through in his storytelling approach, where he weaves cultural references and personality into breaking news coverage. From the Dodgers' 2020 World Series run to the recent Paris Olympics, Casselberry has witnessed sports history while producing 20-25 stories weekly for Yahoo's massive audience.

The conversation delivers practical wisdom for media professionals at any stage: finding unique angles within crowded news cycles, blending personal voice with professional standards, handling editorial feedback constructively and balancing audience demands with creative instincts. Casselberry's journey proves that while the path may not be linear, those with determination and adaptability can build lasting careers telling the stories that connect us all.

Ready to dive deeper into the world of sports media? Follow Ian on social platforms @ian_cass. 


Please take a moment to rate, review and subscribe to the Media in Minutes podcast here or anywhere you get your podcasts: https://podcasts.apple.com/us/podcast/media-in-minutes/id1555710662 

Angela Tuell:

Welcome to Media in Minutes. This is your host, Angela Tuell. This podcast features in-depth interviews with those who report on the world around us. They share everything from their favorite stories to what happened behind the lens and give us a glimpse into their world From our studio here at Communications Redefined. This is Media in Minutes. In today's episode, we're talking with Ian Casselberry, a veteran sports writer and editor who currently is a breaking news writer for Yahoo Sports. With nearly 15 years in sports journalism, ian has written for some of the most recognizable names in sports media, including Sports Illustrated, bleacher Report, espncom, usa Today and many others. A Michigan native, now based in Tennessee, ian began his career writing about Detroit sports and has since covered everything from the Dodgers World Series run to NFL trade deadlines and the media narratives behind major sporting events. Ian calls his greatest achievement being able to make a sustainable living doing the work he loves. Today, we'll talk about his career evolution, lessons from life inside sports media and what's ahead in an ever-changing journalism landscape. Hello, ian, thanks for joining us today.

Ian Casselberry:

Angela, thanks so much for inviting me. That's really really flattering to be a part of your show.

Angela Tuell:

Oh, I am excited to talk with you. I must say, you know, you've spent nearly 15 years in sports media, which is impressive. How did your journey begin?

Ian Casselberry:

Oh gosh. I mean I didn't follow a conventional path, which is something that I always try to emphasize to any young writers who ask about my career and how I may have gotten to where I am. So I started out in the early 2000s writing a personal blog while I was at the University of Iowa, iowa. That's when blogging really started to become popular and actually became a realistic outlet for people, not just to get their writing out there, but some people were getting hired for jobs writing books etc. So I thought it would provide an outlet.

Ian Casselberry:

I mostly started writing and updating the blog as a way for my friends and family back in Michigan. Writing and updating the blog as a way for my friends and family back in Michigan to keep up with what I was doing. I couldn't talk to sports, about sports or movies or TV with them all the time, so then I'd write about it and they can see what I thought. But then I noticed, the more I wrote about sports, that was the stuff that was getting more notice, either by you know, people reading. And then even back home in Michigan the Detroit Free Press noticed me and included me in a piece on local bloggers, even though I was in Iowa. That sort of established a foothold and I kept at it when I finished school and moved back to Michigan and got more notice that way and it just started to build.

Angela Tuell:

Okay, so walk us through your career a little bit from that point to where you are today. I know, I know there's been lots, of, lots of steps, but how would you, how would? You talk about it.

Ian Casselberry:

Again I also. I got featured in a story in the Metro Times, the Detroit Alt Weekly newspaper, and again that just kind of created more notice and it was just plugging away trying to write as regularly as I could. And SB Nation recruited me to run their Detroit Tigers blog, their community Bless you Boys. And that's when I started to be noticed by and establish some relationships with local reporters and out of town reporters began to reach out, you know when their team would play the Tigers. So I always hoped kind of dream that that work could be used as a springboard. But that's when it really began to feel like an actual possibility.

Angela Tuell:

Yeah, and you know sports journalism and I know this because I had a lot of friends as I was in college a lot that were in sports journalism. That's even I'm trying to think of the right way to say it even tougher to work in than other areas of journalism.

Ian Casselberry:

There's just less jobs there are fewer jobs and I think the path to getting better jobs is pretty limited. Yeah, I mean, that's one thing that was great about blogging and I feel really fortunate that it came into popularity at that time, because you know it used to be. You had to try to get a job at a local newspaper, start out covering high school sports. But even moving up like that would depend on whether you know an established writer or somebody who was in there was moving on or giving up a job. And you know, in a lot of cases those jobs are good and people aren't going to give them up, so you would run into a ceiling. So I was fortunate that blogging allowed me an outlet and a chance to learn how to write.

Ian Casselberry:

Yeah, without necessarily following that path, and I certainly understand, at first there was some resentment. I would probably have felt the same way. You know you're at a newspaper and you paid your dues, and here comes somebody who's just you know writing their own stuff on their site. But you know, I think, as they not everybody, but as they discovered, you know, read your stuff realized you were working hard at it too. Maybe it wasn't the same path, but you, if you show you take it seriously and the work is good. Um those, um, that chill started to melt.

Angela Tuell:

Yes, good, good. So you've also so along the way you worked um outlets like sports illustrated bleacher report. You mentioned M live SB nation. It's like Sports Illustrated Bleacher Report. You mentioned MLive SB Nation.

Ian Casselberry:

What did you learn working with so many great sports outlets? I've learned something important, I think, from each of those stops, like with Bleacher Report. It was how to drill deeper to find different angles on a story. Like you know, yankees beat Red Sox is obviously one story, but you know, we would figure out ways to wring out three or four more stories maybe from that. And that's something I feel like I really learned at Bleacher Report.

Ian Casselberry:

Mlive was really my first introduction to a more professional environment and really helped me to learn how to mix my blogging voice with a more formal new style. Like at first, I think I felt like I needed to. I needed to write like they do in the newspaper. And then, you know, you come to realize, or an editor may have said say, you know, we didn't, we didn't hire you to write just like the guys covering the team. You know you. You know we didn't, we didn't hire you to write just like the guys covering the team.

Ian Casselberry:

You know you. You know if you were more irreverent or so forth, we want you to bring that um into that content as well. And then um sports illustrated just um really taught me how to write quickly and cleanly, which I thought I knew how to do before. Um, but again this was in more of a structured environment with stricter editing, and I think that just certainly helped me to where I am today in getting to my point quickly, getting the information that the reader needs quickly, just doing that as concisely as possible.

Angela Tuell:

So how would you describe your writing style and how is it different from others?

Ian Casselberry:

I mean, I try to write in more of less of a formal sports writing style, like if I can kind of weave a little bit more of a storytelling element into there maybe that's more common now and not as different as it once felt and then trying to work you know you can't push it too much, but trying to work maybe a cultural reference in there, you know, like occasionally a song lyric or a movie reference or just something that will appeal to the reader, like, hey, you know, oh, they're just like me, you know they watch Seinfeld or whatever. Right, oh, they're just like me, you know they, they watch Seinfeld or whatever. Um, so I've I've always tried to have some personality in there rather than, um, just be like a dry um. Such and such team beat such and such team, this person hit a home run, et cetera.

Angela Tuell:

Yeah, that's great. I'd love to know some of the highlights of your career so far. I could guess that one might have been the Dodgers 2020 World Series coverage for Sports Illustrated, but I could be wrong. So what are highlights so far?

Ian Casselberry:

That is definitely a highlight. That was an unusual situation because I'm not based in Los Angeles. I wasn't at the time. I couldn't go to games or interview players in the locker room, but it was during COVID, so none of the regular reporters on the beat could either. So we were all sort of in the in the same boat and I could do my job even from North Carolina, um, as strange as that might seem, not being in Los Angeles, but I could do my job in much the same way.

Ian Casselberry:

You know, we, we would talk to the, to the managers and the players via zoom, um, but I was, uh, a friend of mine was working, uh, at sports illustrated and needed some help doing secondary stories, and asked if I'd be interested in helping out. Um, so that, yeah, that was. That was a memorable experience. It was fun and informative, covering a team every single day, which was sort of a dream growing up. And I also remember the time difference being an obstacle, being in the Eastern time zone. I remember, you know, like I would have some regular radio appearances during that time, and there was a couple of them I missed because I fell asleep.

Ian Casselberry:

You know I was so worn out from the late nights, but another real quick, another memorable experience, maybe because it was just so recently, but covering the Paris Olympics with Yahoo, that was just really fun. I mean, covering different sports took me out of a comfort zone in the best way, and it was just really fun. I mean, covering different sports took me out of a comfort zone in the best way and it was just really fun seeing the entire machinery of Yahoo Sports at work and being part of that team, corresponding with editors and reporters in Paris, working at odd hours, and all of us were on the same beat, whereas usually we're kind of fragmented. You know, ok, he's the football editor, he's the MMA editor, etc. But we're all working together to cover the Olympics.

Angela Tuell:

Wow, that does sound fantastic, and you mentioned we said this in our intro but you are a breaking news writer and editor for Yahoo Sports, so where is your focus typically?

Ian Casselberry:

It's the news of the day. I mean, we have meetings beforehand, you know, looking at what might come up. You know, this time of year, you know, with football, college football in the NFL being so prominent, you know looking at who and what are the big stories coming up will be. That's usually how we set the day. Sometimes it just depends on what pops up on the news cycle, but usually we have a good idea of, you know, a certain player is unhappy with their contract, or you know anything the Dallas Cowboys or the Los Angeles Lakers do. You know that's usually something we can cover pretty easily.

Ian Casselberry:

But yeah, usually it depends on the news cycle. And, and I think also, I don't know if we all do this, I hope we do but you know, just kind of keeping a general eye on everything, like just knowing, like okay, if this team wins tonight, they'll make the playoffs, or this team has has won nine in a row and the record is 11. So let's, let's keep an eye on that. And then you know there are personalities that are just always worth covering these days, like Caitlin Clark. Anything she does, you know, she's back. I don't know if I mentioned Caitlin Clark. Anything she does, she's back in practice.

Angela Tuell:

so we'll cover that. I'm in Indianapolis, so oh, okay, all right. We actually saw her at dinner the other night. Really we were the only ones in the rooms together and we noticed that this table was being really loud her and her boyfriend and one other person she wasn't, but you know and when she stood up we're looking at her and we're like that's she saw us just staring and she smiled and waved at us.

Ian Casselberry:

It's really nice because she knew probably as we were looking at her Was that sort of the moment where, like, sometimes you'll see somebody famous in public but you can't quite place where you remember them from. Like I remember seeing a news reporter once at a restaurant I'm like I know her from somewhere and I kept looking at her and finally she looked over at me like what is your problem? Right and I thought oh all right, yes, she's a news reporter, I will stop looking over there.

Angela Tuell:

And you see someone like that who's so famous that it doesn't register that she looks like such a typical normal person, you know, and I just, I don't know, imagining she was much taller than she was or that sort of thing, so yeah, oh, that would have been great.

Ian Casselberry:

I thought you'd be taller.

Angela Tuell:

Right. So how many stories do you typically write a week, or is it a day?

Ian Casselberry:

Oh gosh, it depends on the day and the news cycle. Of course Some stories, you know, generate follow-ups very quickly, like I said before drilling down on a story. But for me, typically I feel like it's a good day if I get four stories in an eight-hour day. So it's typically 20 to 25 stories a week. Sometimes it's more if the stories are real short and to the point and occasionally it's less if you're able to write a little longer, like a reaction or analysis piece. But yeah, I'd say about 20 to 25 a week.

Angela Tuell:

Okay, so do you work with publicists? Often Are they typically pitching you or you know what's your interaction.

Ian Casselberry:

I don't work as much with them at Yahoo because really we're just we are answering or responding to the news cycle. I do get plenty of emails from publicists and media reps about that sort of thing. I I work with them much more when I worked when I covered sports media, because often you know what they were trying to pitch is something that I thought would make for a good story and it would serve our audience. Um, unfortunately and I often feel bad about this is that what I am being pitched just isn't something, um, that I would get to um in in the course of the day or that would serve our audience. And I try to respond and impress upon the person Because I know they have a job to do as well, of course. So, yeah, I don't get to work with public relations as much, but sometimes it works out really well. Like the Cleveland Cavaliers basketball team. But sometimes sometimes it works out really well Like um, the Cleveland Cavaliers basketball team, for instance.

Ian Casselberry:

You know they, they kind of took a step up and were really successful last season and I ended up writing more stories about them just as a consequence of that and their, their people reached out to me. So you know we enjoy the stuff you're writing. You're writing a lot about them, you know. Would you like some more information, or would you like to, you know, cover these sorts of stories? This is what we're doing. So I mean, I guess in my current situation that's, that's an ideal circumstance when it just kind of meshes like that.

Angela Tuell:

Yeah, how does Yahoo Sports work? I mean, there are other journalists that I'm assuming that are assigned to beats outside of breaking right that take on from the stories that you guys write like here's the breaking news, and then they elaborate further as stories are needed If they're covering that beat.

Ian Casselberry:

Yeah, yeah, we, we, yeah, we have our breaking news team and then, like each individual sport, hasists or people who might, they might write news stories as well, but concentrated more on that sport.

Ian Casselberry:

So I kind of think of it as like we take the immediate thing. You know, lebron James signs a new contract and then a columnist will come in and say, okay, this is what this means, this is how likely it is that you know lebron will play for the lakers for the next five years, or how does this affect their ability to put together a team? So, yeah, there are a lot of um, uh, columnists, uh, that work on individual sports. And then with yahoo, yahoo, yahoo Sports is making more of a push into original video and podcasting, which I'm not really a part of that, but it is a bigger thrust of the entire operation which you know. Now we'll have a daily sports program, a daily or, you know, a weekly basketball program, a weekly football program, just trying to reach audiences in podcasting or people who you know increasingly watch on YouTube and things like Roku. That's a bigger part of the operation recently.

Angela Tuell:

Yeah, I can imagine that that's definitely growing. When you started with Yahoo, what were you surprised to learn?

Ian Casselberry:

You know it was a struggle to write what. What does trending mean? I mean, breaking news is pretty self-explanatory, probably. But trending looking at Google Trends and resources like ChartBeat to see what people are clicking and searching for, I had to learn that maybe the more esoteric stories or things that I thought would be funny didn't necessarily have an audience at Yahoo. That's changed. I think we've all had to learn. Our team is relatively new in terms of new editors taking over and new writers coming on, so that was the hardest part. And then just knowing that Yahoo is such a big resource in terms of search engine and so forth, so things you write are going to be picked up by the Yahoo Sports front page or ideally they're picked up by the front page and just trying to write to that audience. That's I mean. You asked what I learned at different stops and I think that's, with each step, just learning that OK you are, you have to write to what the audience wants rather than what you think is interesting.

Angela Tuell:

Yes, absolutely. That's the challenging part of a journalist's job sometimes.

Ian Casselberry:

Yeah.

Angela Tuell:

Does AI play a role in your work?

Ian Casselberry:

It doesn't. There is some, I believe. Yahoo uses AI to transcribe podcasts for people who can't listen or watch. You know that they can read the transcript, but in terms of our writing and editing process, AI has no role.

Angela Tuell:

Yeah, that's a very interesting area With many. We see some outlets using it for, like you said, you know, transcribing or even just intros to articles or planning purposes. So we'll see where it all goes.

Ian Casselberry:

Absolutely, and you know people are ready to pounce on it too if they find out. You know like, oh, we heard that Yahoo or Sports Illustrated is using AI. You know that's crazy. And then you know, a lot of times I mean it's not my job necessarily, but if someone asks I'll answer, but you know that's something that we have to respond to, and then you know what people's idea of what AI would be also is that it doesn't mean AI is writing the story, but maybe they help us do research or something like that. That's a tool, not the main driver of stories.

Angela Tuell:

Right, absolutely. I must ask do you still love sports? I know many times when something you know is our job. It's not as much of a hobby anymore as it was.

Ian Casselberry:

I do love sports and that is something I mean. You're so right. I mean, when it becomes work, it's something that is just your job and maybe you feel the need to get away from and I'm sure this applies in plenty of other beats and areas in journalism as well see some sports writers who don't seem to love sports or don't seem to watch sports, and I think it affects their coverage especially, maybe, as they get older. I do still love sports. I mean, to me that is the fuel, that is the juice, as they said in Heat of what gets, uh, what gets me going on writing is that I still love.

Ian Casselberry:

I still love writing about the sports. I still love conveying, just like you know, do you realize how amazing what that person did is? You know, like you can't do that in your driveway. So, uh, yeah, I still love sports. Maybe I don't watch as much when I'm not working, just to get a little bit of a break from it, but I mean I'm still. I'm watching Michigan football and the Detroit Lions when I'm not working. I still love.

Angela Tuell:

I still love my teams, yeah yeah, football is probably the favorite now Most of my writing has been baseball.

Ian Casselberry:

Baseball is a favorite, yeah, I enjoy all of them. I enjoy, yeah, my local sports teams especially.

Angela Tuell:

That's awesome. Yeah, we talked a little bit in the beginning about having such a sustainable, long career in journalism so far, and it has to be one of your proudest achievements. It's very something that we don't see a lot. You know, there really are a lot of journalists that love to leave the field. How do you think you've managed to stay in journalism and be so successful?

Ian Casselberry:

Some of it is just stubbornness, I suppose, like I don't know what else I'm going to do or could do. I have thought. You know it has been a struggle at times to think okay how can these skills be applied in a different area?

Ian Casselberry:

And, honestly, if we'd been having this conversation two, maybe three years ago, I mean I wasn't sure if I was going to stay in journalism. Um, so I, I was very luckily lucky to catch on with sports illustrated and then, uh, yahoo, I've been fortunate enough, um, you know, to have a really um, supportive family, um, circumstances have worked out where maybe I was able to a chance where others might not. But I think also, you know, struggling and making very little money or working day jobs around journalism also sort of instilled a little bit of a work ethic that somebody who just goes straight, you know, who goes straight out of college and never really had to worry about working a retail job or something like that, a perspective that people like that might not have.

Angela Tuell:

Yes.

Ian Casselberry:

And I think I mean I'm not in the position of hiring anybody, but, like when I look at somebody's resume on LinkedIn, for instance, I mean I some people might say like, oh, you know, they've been working at a coffee shop all throughout college. What do they know about journalism? I said, well, you know, that person knows about working with a team, they know about working with managers, they know about working with customers, and those skills can be applied to journalism. And I think that very often needs to be taken into consideration, more than how many Twitter followers they have, for instance.

Angela Tuell:

Yes, you have to be able to talk to people, yes, and talk not just over, not digitally always, but you have to be able to have those conversations. That's a main skill of journalism.

Ian Casselberry:

Absolutely and yeah, I think that's a skill not enough. Young writers learn not just talking to subjects, but working with editors and taking constructive feedback. Hopefully the feedback is constructive, right and just learning how to you know that it's not a slight against you. Necessarily. They're trying to help you get better or pointing out where you need to improve.

Angela Tuell:

Yeah, so what do you hope the future holds for you professionally?

Ian Casselberry:

Oh gosh. I mean we talked about the different jobs at Yahoo. Being a columnist on a particular sport or beat would be fantastic. I don't know if that's in the cards or not. Like many of your guests, I would certainly love to write a book, bouncing around plenty of ideas. I would love to write a memoir about my mother, for instance. She grew up in Malaysia. She wanted to originally become a nun and then she she left Malaysia to come to America when she met my father in the Peace Corps and I just.

Ian Casselberry:

there's so many stories there not just that I want to tell people, but I want to learn myself in having those conversations with my mother, and this is something, unfortunately, I've talked about for like 10 years and haven't I've only really dipped my toe in and I really hope to have an opportunity to work on something like that in the future.

Angela Tuell:

That's something you just have to start doing so it doesn't get too late, right.

Ian Casselberry:

Yes, that is exactly before it gets too late. Yes, yes, use a recorder. You don, that is exactly before it gets too late.

Angela Tuell:

Yes, yes, use a recorder. You don't even have to start writing yet, right, you could just record it all in.

Ian Casselberry:

Right, I just you know, just get used to me having my phone in your face.

Angela Tuell:

Right, exactly, it's so natural. So how can our listeners connect with you online?

Ian Casselberry:

I am on all of the uh popular social media platforms um. Blue sky and instagram and facebook are probably um my preferred or or uh most fun outlets um I'm ian cass on all of those outlets. I-a-n-c-a-s-s um I am on twitter and threads, but I don't use those outlets as much. I mean, I will respond if anyone were to reach out, but I just don't update those those platforms very much. I am on TikTok, but I am not. I am not active on TikTok. I don't feel my dance skills are strong enough yet, much to the disappointment of my nieces.

Angela Tuell:

Right, I'm sure.

Ian Casselberry:

But yeah, that's how I can connect with people.

Angela Tuell:

Wonderful and your blog is still active.

Ian Casselberry:

Not as active as I'd like it to be. The blogging for Yahoo takes up so much time and then I have time off. I just don't have the energy or the interest. I'm trying to keep it up. It is important to me to write about different things and, as I said earlier, my personal writing has always been a way of keeping up with my friends. Really, I feel like I write for my friends more than anybody else. Friends, really, I feel like I write for my friends more than anybody else, and I think it's important to use writing muscles that I don't always get to use when covering sports or even just to see how you know how I approach sports could be applied to something else, like writing about arts and culture.

Angela Tuell:

Right.

Ian Casselberry:

Yeah.

Angela Tuell:

Yeah, your skills are not only in sports, even though it may feel like it sometimes, right?

Ian Casselberry:

Right, I have multitudes.

Angela Tuell:

Well, thank you so much, Ian.

Ian Casselberry:

Thank you so much for having me on your podcast, Angela. This has been great.

Angela Tuell:

That's all for this episode of Media in Minutes, a podcast by Communications Redefined. Take a moment to rate, review and subscribe to our show. We'd love to hear what you think you can find more at communicationsredefinedcom slash podcast. I'm your host, Angela Tuell. Talk to you next time.