Jason A. Churchill is a podcaster, writer, and editor. A native of the Seattle area, he spent time covering local prep and college sports before making the jump to ESPN. From there he joined CBS Radio where he co-hosted a show with Steve Sandmeyer. He currently works at Data Skrive, while also hosting his podcast Baseball Things and running his website Prospect Insider. Jason’s journey was anything but easy and he was kind enough to share some of the lessons he learned along the way. Here’s his story!
Who are you and what are you currently working on?
I’m Jason A. Churchill. I’m a native of the Seattle area and a big sports fan. Growing up, there’s a moment when you first realize that hitting an 87 mph slider and a 95 mph fastball is really not in the cards, so you try to figure out another way to stay in sports. Or, if you’re a music person and you figure out you can’t sing, you try and find a different way to stay in music. Baseball is kind of my thing, so I tried to figure out a way that I could stay in baseball, and it’s led me to a really interesting point. My day job really has nothing to do with baseball or even sports in general; I’m currently working for a company that automates content, and I write a lot of the templates for it. That company started out as a sports publishing company and that’s how I got started there.
Most of the sports stuff that I do—which is how the seven people that know me know me—is side work now. My website at ProspectInsider.com and my podcast, Baseball Things, are side projects that I do just because I enjoy them. These days, I spend just as much time on my side gigs as I do my day job—don’t tell the boss!
How did you come to be where you are now?
Coming out of high school, I was as unprepared for life as anybody on planet Earth, and that’s not a stretch. It was nobody’s fault but my own. I was kind of aloof about graduation and just didn’t prepare myself for life after high school. Because of that, I spent a lot of time after graduation just bouncing between random jobs, not really knowing where I was going to get my next paycheck, let alone where I was going to be in a year or more. Things got really tough for me. My relationships with my family became strained because I was that guy bouncing around from job to job, and when you’re 22 years old, borrowing money from your parents, that’s a real wake up call. I was in trouble. I was one of those guys.
In about 2001, the internet was exploding and I was using it to follow and read about sports. Then I discovered places where I could converse with folks about baseball. It was on BaseballBoards.com that I started to meet people and see how interested other people were in the same things that I was.
About a year after I started posting on that site, I got a call from a friend of mine, Joe Kaiser. Joe was writing for DawgMan.com (Washington Huskies fans from the Seattle area, probably remember DawgMan.com. They’re over on the 247Sports network now). He was starting a baseball version of DawgMan.com and wanted me to contribute. InsideThePark.com on the Scout.com network was the first place that I ever had anything I’d written about baseball published. While I didn’t really see it at the time, it ended up being an opportunity for me to have some fun, learn a lot, and eventually, it became a stepping stone to the next thing in my life, which ended up being my website.
Joe asked me if I was interested in covering some prep and college sports for some of the local newspapers, and I started freelancing, doing high school sports for the Tacoma News Tribune. At this point, I was living in Tacoma, so the location was perfect. I was running around on Friday nights, trying to meet a deadline at 10:00 pm. It’s important to remember that this is back in the early 2000s when it wasn’t that easy to find Wi-Fi. It was an adventure, to say the least. I have countless stories about things like having to stop at an AMPM in Federal Way to plug into their dial-up and file a story because there was no way I was going to get home in time to meet the deadline.
It was that work which helped me gain the opportunity to write a weekly column for the Seattle PI, and that got me noticed a little bit. By that time I had also started covering the Mariners’ minor league farm system on my own website: ProspectInsider.com. And even though the team was terrible, there was interest in that, because that was the future. I poured my heart and soul into it, and for almost three years, the website was my living. I learned a lot while doing that.
Thanks to all the work that I put in on my website—covering the draft and prospects, and learning about scouting and player development—I got a call from Keith Law at ESPN in the winter of 2008. He asked, “Hey, do you want to cover the MLB draft with me at ESPN?” which was easiest question of all time. I did that for four and a half years, while also doing some other stuff for ESPN. Working at ESPN opened a lot of doors for me. It’s a really cool thing to be able to put those four letters, E-S-P-N, on your resume.
I was probably 30 years old before I realized that I could do something with this baseball thing and that it was worth pursuing. I was about 30 seconds from giving up entirely in 2008, and the only thing that stopped me was some words of encouragement from some folks that were close to me. It was a long battle for me even after I’d gotten ESPN opportunity.
After ESPN I went to CBS Radio, here in the Seattle market and did a radio show with Steve Sandmeyer. That show was by far the greatest job of all time. Every single day I woke up excited for work. It was literally my job to talk about sports every single day. It was amazing.
After the CBS Radio gig, CBS ended up firing everybody and selling off all their radio properties. That’s when I landed my current job at a company called Data Skrive. When I was hired, it was a website covering college sports and all the non-revenue sports at the college and prep levels. It was my first full-time editing gig, which was a lot of fun. The company eventually pivoted from publishing to technology and now my role is in data configuration and sales engineering. It’s funny because a lot of the things that I’ve learned in my new role make me want to go back to the early 2000s when I was starting Prospect Insider and implement all of the things that I know now. I think things would have turned out a lot differently if I knew then what I know now.
It’s been a long journey. I’m in my mid-40s, and if you’d asked me 10 years ago how I felt about things, I would have been nervous and stressed out. Now I don’t even know what tomorrow is going to look like, but I’m not nervous or stressed about it. I’ve learned a lot of things along the way, and I’ve had help from folks that I never really knew had insight on things. One of the coolest things I’ve learned is that when you fail—because you will and I did fail miserably every step of the way—people will point it out. But there are also folks that are close to you that will point it out in a manner that you may never think of. I had people say, “Okay, you lost your radio show, but think about why that actually happened. Did that have anything to do with your performance or the show’s performance?” No, so I started looking at things in a more positive way. I started seeing the things I did well and the opportunities to improve instead of just focusing on the points where I may have fallen short. Fortunately, I’ve been able to implement that mentality as I’ve moved forward.
There’s a part of my journey that I left out that I probably shouldn’t have. I don’t want to glorify it, but it’s an important part of the story. There was a time right around 2004 where a relationship ended and instead of going to folks close to me for help, I was literally homeless for about five and a half months. Every once in a while I’d crash at my parents’ house, my sister’s house, or a friend’s house, but probably five days a week for about five and a half months I slept in my car. I was 29 or 30 years old at that point. I had work and I had some money coming in, but I just didn’t have my “s-h-i-t” together, so to speak.
I was stressed 24 hours a day at that point; you can’t sit in a parking lot at 2 am in any town and not have the police knock on your window and wonder why you’re there. You don’t sleep that well or that long when you’re sleeping in your car. You don’t know where you’re going to shower. Simple things were very difficult for me to figure out. That was about right when I started to get some of the freelance gigs at the News Tribune, and about right as I took the weekly gig at the PI, doing the prospects column there.
Pretty much every day during that time I just lied to myself and told myself that I was close to figuring it out even though I wasn’t really doing things that would help to get me out of it. I needed to actually just ask somebody for help that could literally hand over the help in an instant. For so long I just didn’t do it, and as soon as I finally went to a family member and said “I need a place to crash for a while” I started to see light at the end of the tunnel. It was still stressful and difficult, but there was light at the end of the tunnel. I never told anybody for years about that situation that I was in, and I’m not exactly sure why.
If you could go back in time, would you tell yourself to ask for help at the beginning of that five and a half months?
I would tell myself to ask for help sooner, but maybe not right away. I really do value the thoughts that I was having while going through that and how I see those situations now. We all pass the folks on the side of the road holding signs. Well, I never held a sign. I wasn’t brave enough to ask for help, and those folks are asking for help. Yes, there’s a large portion of them buying cigarettes and alcohol with it, but I’m willing to take that chance because there’s a chance that person is just hungry and cold. While I think that I would still have the same feelings about those situations if I hadn’t gone through it, I think I’m a lot more aggressive about it because of my experience. That was the low point for me, and I think, to some level, I need that. I need to know that it was there.
Maybe I should have asked for help halfway through, or a month or two in. But I think going through that does give me an extra level of insight on what it feels like when your life just seems to be spiraling out of control, or it’s hit rock bottom, or at least feels like it’s hit rock bottom and you don’t know how to climb out of it. Maybe I can help.
What does growth mean to you?
When I hear personal growth, I think about understanding the difficult situations of others. I don’t have any kids of my own, and when I met my wife, her son was six. I don’t think I understood how difficult things were for single parents, even though I grew up in a single-parent household. After having that personal experience with my wife, Shannon, and her son, Ashton, I started asking myself questions like: Did my mom go through this too? I was eight years old when my parents divorced and I have two younger sisters. Did they go through similar stuff? Do my friends? Do the people that I work with? Are they in similar situations?
So when I think about what personal growth means to me, a large part of it is realizing that you don’t know what other people are going through. And being able to learn about it or at least move along on a daily basis without assuming things about others. I’m reminded of the golden rule: “do unto others as you would have them do unto you” I think not assuming anything about folks’ situation is really important.
There’s a lot of room for improvement in the way we treat people these days, and I think it starts from within. I think you kind of have to knock yourself on the side of the head and go, “Wow, I never realized that!” That’s a mistake that I probably still make every single day, but I think I’ve been significantly more mindful of it the last 15 years, because of my personal experiences.
What piece of advice or request do you have for our readers?
Ask for help. If you want to do something, there’s a path to get there, and it really doesn’t matter what it is. If somebody said, “Hey, I’m 40 years old, and I want to be a Hollywood movie star. You’re telling me there’s a path to that?” Absolutely. If you want to put in the time and the work, and move to Hollywood, then there absolutely is a path. It doesn’t matter what it is you want to do, there is a path from where you are to everything and anything out there. Ask for help and never stop asking for help until you figure it out. You may change your mind along the way and say “You know what? I did really want to do this, but now I kind of want to do this other thing more.” But you got to that point because of the questions you were asking and the journey you were taking to get to the original point B.
You need to ask for help. It’s kind of the theme of this entire conversation. It doesn’t always have to be a person that you ask. The internet is a great source of information these days, and often a good place to start. If you ask for or look for help, and start talking to folks about your question, they might have some insight, or they might know somebody that can help. There are probably 10 people in my life, that if any one of them weren’t there to help me, to offer advice, or to point me in the right direction, then I wouldn’t be where I am today. I’d be fine, because I have the other nine people, but I certainly wouldn’t be where I am today.
In the end, you do have to chase down answers. And sometimes that involves conversations with people you don’t actually know. I’ve asked writers that I don’t even know questions. Back in about 1997, I was beginning to think that sports radio seemed like something that I wanted to get into someday. There was a radio host in the Seattle area named Dave “Groz” Grosby. He would always say “Hey, if you have questions, email me.” While he meant questions about sports, I emailed him and said, “Hey, I love this sports radio thing. I think I’d have a passion for it. What’s the best place for me to go to school?” He responded with “Don’t waste your time doing things that aren’t necessary.” If I wouldn’t have asked Groz for that help, I wouldn’t be here today. This interview wouldn’t be happening; something along the way wouldn’t have happened that did happen because I reached out and asked a total stranger for assistance. Never stop trying to find the answer to a question that you feel you need an answer to. And, you know, there really are no stupid questions.