Happy Wednesday,
There’s one question that Jake and I get asked more than any other: how do you work in sports? So this week, we took the time to answer it properly.
This isn't a comprehensive guide to landing your dream job as a sports creative, but hopefully, by dissecting our own journeys and sharing a few practical pointers, you can break into the industry too.
Saying you're passionate about sports is the equivalent of saying you're proficient in Excel. So is everybody. That's not a differentiating attribute.
How We Got Here
Jake's path:
Freshman year: Enrolled in business school at the University of Minnesota with vague plans to go pre-med, took one chemistry class, immediately abandoned the idea
Sophomore year: Opened an LLC and a business checking account; the business did nothing for six months, but it existed
The LinkedIn loophole: As a student, got free access to all of LinkedIn's premium features, DMed every single graduate of the Carlson School of Management just to do informational interviews — finance, accounting, marketing, anything
First paid work: $30 an episode to produce a podcast. Was "rolling in it"
The break: Cold DMed sports lawyer Josh Schaub on a Monday, met him Tuesday, got an Excel project Thursday, had his brother's computer science friend complete it in five minutes, presented it like he'd built it himself. That relationship led to working with the American Association of Professional Baseball, which we still work with today
Meeting Tyler: Reached out on LinkedIn after seeing social media content Tyler was posting, called him from a road trip in the Outer Banks and said: "we're not gonna make much money on this." They split everything 50/50 until they looked up one day and formalized it as Uncle Charlie
Tyler's path:
College: Wanted to be a doctor for the same reason Jake did (it sounded impressive). One chemistry class later, same result
The theme pages: Was running Instagram pages and Twitter accounts about sports in the margins of boring marketing internships; data entry jobs that took four hours but required 40. The creative work was fun because there was no financial pressure tied to it
The graphic: Early freelance client Nate Dorton asked Tyler to make a graphic celebrating a football record. Tyler had never made a graphic, so he Googled every step, charged $100 (it was awful), but got more work anyway.
The signal: Started getting pulled into rooms at internships because someone had noticed he was running a Twitter account with 100,000 followers. Talked out of his ass about marketing strategy but got more opportunities because of it.
The Big Idea:
I can’t take credit for this idea, but I genuinely believe that the best way to start working as a sports creative is to get a job waiting tables (or delivering pizzas, substitute teaching, or literally doing anything else).
A quick economics refresher for you: if the supply of something is very low but the demand for it is very high, the “cost” to acquire that thing will be very high. That’s the reality of getting a job in sports. A lot of people want one, but there aren’t many.
This leaves young, aspiring creatives (often with limited professional experience) with a few options:
Work for free
Work an unrelated job in sports (ex., selling tickets)
Work in an unrelated job outside of sports while developing your skills on the side
I’d argue that the best people I’ve ever worked with or hired did option #3. They made their money doing something else, but in their free time, they developed hard, tangible skills that made them attractive applicants even though they never technically worked for a brand, team, or league.
I love this option because it means that your creativity isn’t tied to any financial outcome (or lack thereof). This gives you the freedom and flexibility to try a bunch of things out, make a ton of mistakes, and really pursue the areas of the industry you’re passionate about.
Then, given enough time and a certain level of success/talent, I believe you’ll have a solid portfolio and practical skills to take to a real brand, team, league, etc., and get a job.
5 Tactical Takeaways
1. The informational interview is still the best tool nobody uses correctly.
Jake DMed every graduate of his business school on LinkedIn, not to ask for a job but to ask what they did and how they did it. The job offers came later, as a byproduct of those conversations. Most people make the mistake of skipping straight to the ask. The goal of a cold outreach early in your career is to learn, not to land. The landing happens naturally when you've built enough of those relationships.
Bonus tip: start a podcast instead, and people are much more likely to talk to you.
2. Say yes and figure it out later.
Jake got an Excel project he had no idea how to complete and said he'd figure it out. Tyler got asked to make a graphic he'd never made and charged $100 for it. Neither of them knew what they were doing, but both of them did the work. The pattern that gets you into rooms is not competence; it's willingness. Competence follows.
3. Don't mix financial pressure with the things you're trying to figure out.
The years Tyler spent running sports theme pages were productive specifically because he didn't need them to make money; he had boring internships for that. The minute you tie financial survival to something you're trying to discover whether you enjoy, the relationship with that thing changes completely. If you're in college or early in your career, people expect you to still be figuring your life out, so use that window to try a bunch of things that probably won’t work.
4. Be the person people want to work with before you're the person people need.
Maggie, who runs social for the Masters and the Kentucky Derby, says social media requires social people. The hours are too long, the pay is often too low, and the environments are too stressful for you to also be difficult to work with. Especially early on — when your skills are still developing — being genuinely easy and enjoyable to work with is the one thing you can fully control. Jake and Tyler have both overlooked skill gaps for people they loved working with. Neither of them has ever overlooked a bad attitude for someone technically impressive.
5. When you reach out, say less.
Jake gets cold outreach almost every day. Most of it is six paragraphs of backstory he doesn't have time to read. What he actually wants to know is three things: who are you, what can you do, and what proof do you have that you can do it well? That's it. Tyler adds one thing: be specific. A cold DM that references something real and specific that you saw and connected with signals that this isn't a mass blast, and it makes the person on the receiving end feel obligated to respond.
Why It Matters
The irony of this episode isn't lost on us. Jake and I get asked constantly how to work in sports, and although we often roll our eyes at the question, a meaningful part of how we got here was people like Josh Schaub taking the time to answer that exact question when we asked. We didn't always have anything impressive to show for ourselves. We just kept showing up, kept doing work, kept making stuff, and eventually something clicked.
The path into sports (especially the creative side) is less linear than people expect and more accessible than they think. You don't need an internship at ESPN. You need a phone, a social media account, and the willingness to make something for no reason other than to see if you can.
The rest tends to take care of itself, at least it did for us.
📩 And don’t forget: Bottom of the Ninth is back this Friday with the top three stories in sports and business from the week.
See you then,
Tyler & Jake