Working in Sports: a Non-Linear Path

Working in sports is a dream for many, but a reality for few. It's not for lack of passion, work ethic, or competence. It boils down to one trait: persistence. As fans of sports ourselves, we laud and gush over professional athletes who work their way back from a devastating injury, who get cut from a team and find success elsewhere, or overcome impossible odds to find success at the highest level. In many ways, we project ourselves, or who we want to be, within these athletes. We glorify the act of persistence itself.

So, how do you get a job in sports? I don't have all the answers. I think if anyone tells you there's a definitive pathway or journey that's a guaranteed end road to a job in sports, then they're not painting an accurate picture.

All I know is how I got there, and it's a jagged line, not a straight one.

From Passion To Production

I, like tens of millions of others, grew up loving football. I played football, but wasn't very good at it. But, that didn't stop me from consuming every shard of content and knowledge I could get my hands on. I devoured NFL Films after school, wrote my own plays in a notebook that no one would ever read, and hoped that one day, I could even just be adjacent to the game and that was good enough for me.

Fast forward to my Senior year of college. Honestly, the only thing keeping me connected to football at this point was fantasy football. Not only did it keep me connected to the sport, but it kept me talking to my high school friends. If it weren't for my fantasy league, there's a very high chance we never would've spoken again after graduation. The league is going 10 years strong to the day. I was 2 months away from graduation when COVID hit the world. My school shut down, life slowed down, and everything flipped upside down. It was at that point myself and a close friend joined "Fantasy Twitter" (X). Simply put, we were bored, and were researching cool ideas for our fantasy league next year.

That was when I discovered Sleeper and Dynasty leagues. Over the next 2 months, I spent my days after getting homework done, and coming home from work at the nursing home, consuming fantasy content on this site, listening to podcasts, and joining what felt like hundreds of Dynasty startups. I was fully hooked. Somewhere along the way, I decided to just start posting my research and thoughts on fantasy players. I mostly did it for myself as a way to remember important information, and never expected it to go anywhere.

Fast forward a little while longer, and my account had accumulated a small following, and people started asking if I'd help give advice on their fantasy team, or if I had articles to read. It was at that point I went from content consumer to content creator. There's a key distinction there.

Building Skills

I and my friend launched a website, The Fantasy Football Clinic, and people in the space were gracious enough to write for that site even though there was no money behind it. Everyone was just looking for a way to gain experience and put their name on an article. I quickly found myself going from a scroller on Twitter (X) to editing other's articles, building Discord communities, writing my own articles, and advising others on what to do on a Sunday morning with their fantasy lineup.

It was through starting a fantasy football website that I learned:

- How to Edit

- What the heck SEO even means

- How to then use SEO to get content discovered

- How to market content organically on social media

- How to manage a team of writers

- How to pay the bills on a domain (I was a broke college kid after all)

The website quickly turned into a portfolio of work that I was able to use to apply to freelance writing positions at 4for4 Fantasy Football and DFSKarma.com . When I got my first paid written article from another fantasy football company(s), I thought I had "made it." My goal was never to make money doing this, but being directly paid by others for my work brought a sense of validation that I didn't know existed. I also got to learn how content companies, the planning that goes into a content calendar, and the critical importance of meeting your deadlines. (You don't want your editors angry at you, trust me). I also took up podcast and video editing with these companies, because why not? I didn't know much, but I worked tirelessly to learn as much as I could to be useful. Oh, and I ended up starting a podcast, because why not? It gave me confidence speaking, and taught me how to concisely organize my thoughts when speaking (something I still am working at).

Note: Say yes a LOT. It'll pay off.

In the background of all of this, I started a career in non-profit fundraising for my Alma Mater, then later made the leap to a BIG10 school.

At one point in my life, this was my daily schedule:

- 5:00am - Record Podcast: I had my first child around this time, so it was the only time I could record where it was quiet. I would then edit my podcast immediately after.

- 6:00am - Write Articles: Most days I had 1-2 to write, so I had roughly a half hour for each to submit before I went to my full-time job.

- 7:00am - Family Time: Would hang out with wife and kid before I had to go to work.

- 8:00am - Commute: It was an hour commute each way, so I spent the following hour on the road usually listening to fantasy podcasts. I was constantly listening to others to try and learn how to make my own content better.

- 9:00am - 5:00pm Work: At my non-profit jobs, I learned a lot of the core skills of digital marketing. I learned how to do paid acquisition via Meta, Google, and Twitter (X) Ads. I also learned the ins-and-outs of CRM Marketing, Email Marketing, Crowdfunding, Organic Social Media Marketing, and I'm sure a few other things I'm missing.

- 5:00pm - 6:00pm - Commute - 6:30pm - 7:00pm - Email Newsletter: One of the companies I used to run emails for, this is when I'd put that together and send it out. Or prep the next day's newsletter.

- 7:00pm - 10:00pm - Family - 10:00pm - 11:00pm

- Reply to People on Twitter (X)

Sleep

I had that same exact schedule for half a year. It may not sound like a long time, but with a schedule being that tight, and a young kid, it can wear on you. I was applying to roles as they came up, each time met with the same answer: no. But, for every no I got, I asked why. I asked the companies why I wasn't considered a fit and what I could do better so that I could land a role in the industry. I picked up invaluable feedback on the way. Truth be told, for the roles I was told no for, I wasn't ready looking back in hindsight. I needed those no's to finally figure out how to get a yes.

I'll never forget connecting with people in the space like Kyle Borgognoni , who to this day wrote me the kindest, most helpful rejection letter I've ever received. Or JJ Zachariason , who would always take the time to tell me what I could be doing better in my content when I'd send it to him. Heck, I should have thanked him more for even listening/reading it. People often look at others in the fantasy space and are scared to approach. DM people. Ask for help and advice. You never know who will respond.

"Making It"

It's a term tossed around a LOT in sports media. I don't take issue with it, but it needs definition. It means something different for everyone. To me, for the longest time, it had meant writing about fantasy football full-time. However, my first full-time job didn't come through fantasy football. I actually applied for a fantasy writer job at Pro Football Network , but was offered a Growth Marketing role. I didn't realize it right away, but it was what I was meant to do (Growth Marketing). It was the perfect hybrid of the skills I honed in content creation, and the marketing skills I had learned in my full-time role in the non-profit sector. I'm forever grateful for that job, because I didn't realize what I really needed until I had it right in front of me.

The role at PFN was like breathing air for the first time. Going from an hour commute and multiple side jobs to one job where I was fully remote and only focused on football was like something out of a dream. I ate up every single day and loved it, and learned a lot about how a football company works, how coveted these jobs in the industry are, and how hard people who work full-time in this space really work.

Remember, when people are sitting on the couch enjoying a football game, there are teams of people behind that game working to make it happen. People don't often think about how your working hours will change once you full-time work in the space. It's something I've seen folks struggle with, and it's likely not for everyone.

Fast forward another year, I landed the job I have now at Sleeper, which still feels surreal. I mentioned Sleeper earlier in this, but I had actually been using Sleeper as my news and alerts platform since 2016 (when I was a Senior in high school). Sleeper had always been there for me in the background with alerts that I could use to get an edge on my fantasy league, and then later with fantasy leagues of their own, to where I connected with countless friends that I remain connected with to this day. Sports is the great connector, and there is no better place to connect with other sports fans than Sleeper. I've believed that from day 1 before I worked there, and continue to strive to bring the platform to more people so they can see how special it really is.

There is a real difference in doing work you are passionate about. Work does not feel like work for me compared to my past jobs not in sports, which gives me the ability to attack every day with urgency and enthusiasm. That's not something you can fake or buy, it must come genuinely. However, I still haven't "made it." I'm grateful and don't take for granted the blessing working in sports is, because I know so many people want it. It's for that reason that you have to stay hungry and motivated.

So, What is "Making It"?

The answer: it depends.

It depends on you. It depends on your goals, personally and professionally. To me, making it is a moving goal post.

I thought I made it when I got paid to write an article. Then I thought I made it when I connected with industry leaders. Then I thought I made it when I got a full-time job in the space. To me, the chase and pursuit is sweeter than the end destination itself. It's what keeps me striving to constantly push higher. I persisted to meet my first definition, and I'll continue persisting to chase to new heights and move my own goal posts of that definition. I look at everything with a Growth Mindset. As long as I can get incrementally better at something every single day, that to me is making it. No matter how small that improvement is, it accumulates over time.

So, whatever your version of making it is, persist in chasing it. Then, when you reach it, change your definition to something higher, and chase it down. Like a great comeback story, we persist.

Also, if you ever want to reach out to talk about how to get into sports, I'm just a DM away. I may take a bit to respond, but I will respond. I believe in paying back what others did for me.