Tyler Webb is the co-founder of Uncle Charlie Marketing and a freelance content creator with a focus on sports business. Webb has over 153K followers on Tik Tok and 130K on YouTube. His breakdowns of sports business stories have led to brands such as Sports Business Journal, Tick Pick and Sleeper Fantasy Sports contracting him for projects.
Webb graduated from the University of Minnesota in 2020, and with a canceled internship due to COVID fell into the world of freelance social media management. Following graduation, he connected with his business partner Jake Kranz. Webb and Kranz launched Uncle Charlie Marketing in 2021, a sports marketing agency producing organic social content for clients.
By the summer of 2022 Webb got the itch to produce social content for himself, which his business partner graciously allowed. Through trial and error, he settled on a break-neck style of producing vertical videos that entertain and inform sports fans and sports business junkies.
In this conversation with BSM Digital Director Alex Reynolds, Webb discusses his process for producing videos and why he – and social media as a whole – may be shifting to a slower approach. Be advised this conversation has been edited for clarity and brevity. For the full conversation check out the BSM YouTube page. To catch up on prior conversations from our Social Studies series, click here.
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AR: I definitely want to dive into the sports business portion of the content creation that you’re doing now but let’s first go back to those early agency days: What did you learn about social media in that time?
TW: I learned a lot. I think the lens that I was able to learn through was how to communicate what you were doing on social media. I’m a bit more of a purist in the sense that I want to do the things that I think are going to work well. And early on, I didn’t take outside feedback very well. So it was nice to have Jake to sort of smooth out my rough edges.
At the same time, when I was interfacing with clients, I had to realize that there are considerations you have to make from a client perspective. They’re handing their brand over to you. In a way it’s an exercise that requires a lot of trust. To think that you know best for what their brand is a little foolish and naive. Maybe even a little overconfident. Being able to understand, what’s the lens that people are seeing this through? It’s not me doing everything for them. It’s me being a shepherd of their brand.
Secondly, there are just ways that you have to communicate better when doing it. It shouldn’t be ‘I’m doing this because I think it’ll do well.’ You can extrapolate many things from many strategies. There are ways to say better what you’re doing then ‘I’m just going to do it because I think it works.’
AR: Tell me about going off on your own, finding your voice on social media, and discovering your lane in sports business.
TW: So I mentioned the bad iterations of content that I did before. I’ve now realized, and this is only the benefit of hindsight, I wasn’t checking three boxes for me when I was doing stuff that wasn’t working.
I wasn’t doing stuff that felt like I could do it for a long time. I think there’s an element of consistency that you have to bake into, especially this kind of short form content. You can overextend yourself and make content for a week and be like, ‘Man, I’m tired, I can never do that again.’ For me, sitting down in front of a microphone is a much more sustainable format.
Two was just what I felt qualified to talk about. When I look back at those early videos, I’m not the best video editor. I’m probably not even the best agency owner. So to talk about those things from a position of, ‘I know what I’m doing better than you know what you’re doing’, felt really disingenuous. It came across that way too. Me talking about my general interest in stories in sports and business and marketing, based on my experience, was a much more natural fit.
Three was something that performed well. I think the niche, specifically of sports business, was underserved to an extent. Obviously, there’s plenty of people that are willing to give you their take on the top five quarterbacks and talk about sports at large. But the niche of the financial, economic, and human interest side of sports, I thought was relatively under tapped. And so I was able to succeed in some of these videos.
I like to equate it to a Venn diagram of, I’m sitting in the middle of stuff that performs well, stuff that feels natural to me that I feel qualified to talk about, and stuff that I can talk about for a very long time.
AR: What about your process and what it looks like in terms of research and production.
TW: The research for me goes back to topic selection, finding angles that I think I can take. Then, I just do a lot of reading. My favorite sources are the Front Office Sports and Sports Business Journal’s of the world. I try to get as many sources and cross check as many facts and figures.
Then I sit and try to work on the hook first. If I can’t find a compelling hook, no matter how interesting the entire story is, it’s not a video I’m going to make. You don’t want to be too sensationalizing and say something that’s completely false. But I think there are creative ways to say something that might seem hard to believe or maybe is hard to believe, to the extent that it’s not true if you take it at face value, but only in watching the entire video does that initial hook get explained.
The tricky part about short form social [content] is you can have something that’s super sensationalized or super click-baity. If somebody doesn’t understand the context of why it matters to them (people are very selfish when they’re watching) they’re not going to sit there and watch because they don’t think the information they’re about to receive is applicable to them.
So in that first couple of seconds, say something that’s going to shock them. Get them to stop scrolling. Then say something that puts it in context for why it matters to them. Then very quickly, you have to get into the information. Because if you don’t start backing up that information right away, people are gonna say, ‘Yeah, this is a total waste of my time,’ right?
I think people are willing to stick around if the information is good. You keep giving them that same feedback loop of saying something sensational and backing it up. Depending on how long your video is, you might have to repeat that cycle two or three or four times. But if you can keep repeating and then backing up, repeating and backing up, I think people are willing to sit around for a long time.
AR: Tell me about the audience that you’ve found on TikTok. They’re not only coming to you for entertaining content around sports, but actual sports business content.
TW: I heard something said recently, ‘not every piece of content is going to serve every segment of your audience in every single way.’ There are some pieces of content when I’m making it, I know it’s going to be widely appealing. Maybe it’s just a very visual concept, maybe it’s not a super dense concept. This is going to be a “viral” type video where you know it’ll have mass appeal.
Then there are other videos that are for my hardcore, sports marketing nerds. Those probably will never do as well as something that has a super high viral appeal. And that’s okay, because it’s meant to target a certain subset of people.
I think a differentiating factor is that I also have worked in the industry. That brings out a certain young college student professional that’s aspiring to work in sports media, or aspiring to work in sports business. The fact that I get to rely on that experience from time to time, or have it as a backdrop to my content, I think pulls out the young professionals.
I kind of find myself in that professional segment of people, whereas maybe people making content about sports at large, are just falling into the lap of the casual fan. Again, I’m sure a lot of my content does fall into the lap of the casual fan, but I’m finding that my most dedicated fan base and the people I interface with the most also work in the industry.
AR: Tell me a little bit about the strategies outside of Tik Tok and Instagram. You also use X, YouTube and LinkedIn so kind of dive into those.
TW: The short form stuff that you mentioned (Tik Tok/ Instagram Reels) that’s just going to be the machine that keeps running. I’ve got it systemized down to a process where I know I can get a video out per day. So now for me in 2024, it’s trying to drive subscribers to my newsletter, which is long form written content. Then it’s long form YouTube, which is a totally different type of beat than the kind of short form content that I make.
I’ve been really active on LinkedIn for a while, and I only just started repurposing my LinkedIn content to X. But the dirty secret is that my LinkedIn content is just a repurposing of the scripting that I’m doing for my Tik Tok.
Frank Michael Smith, a really talented creator that I aspire to be in a lot of ways, he continually reminds me, repurpose the stuff you do. I think it’s a really good reminder because I get caught up in my own BS where I’m like, ‘Everybody’s reading everything I’m putting out so they’re going to know that this post I had on LinkedIn is just a script for a Tik Tok that I posted last week.’ But you’re really hitting different segments.
Honestly, I think that’s probably been an unsung reason for some of my growth. I’m just perforating so many different areas of an organization that if the young social media intern brings my Tik Tok to an executive, that executive might have already seen my written stuff on a certain platform. There’s a coherence of what my brand is across all these different platforms and mediums.
AR: Wrapping up, is there anything you want to add about what you’ve observed about the current state of the social media landscape?
TW: I think we’re already in this shift. I’ve heard it being called FaceTime content, which I have really come to appreciate. It’s this idea that you don’t have to give your undivided attention to a piece of content to understand it and consume it. Podcasts are a great example of this, just having your ear.
I’m thinking about this in the context of YouTube, where there’s a YouTube video that I can have on, and I can walk away from it with my Bluetooth headphones and come back to it. And I’m still getting the gist of what’s happening without looking at it. Or I’ve set my phone down and I’m on the other side of the kitchen but a Tik Tok is playing and I’m listening to it.
My editing style in the past has been very in your face, very reliant on things happening on the screen. I think I’m looking now at a slower pace of editing something that is much more driven by storytelling and much less driven by editing style or sound effects and sensationalized visuals. I’m trying to get back to my roots as a really good storyteller. Because I want to make sure that people can walk away from whatever they’re doing, and still listen and understand what I’m talking about.
I think there’s another component to where people don’t feel like when they scroll on a video, maybe they’re a little tired, it’s late at night, early in the morning, they’re not in the best mood. Maybe they don’t have the energy to consume a three minute video by Tyler where I’m doing a deep dive on stadium urban planning. I want to make sure that I’m an easy watch or a low effort watch. That doesn’t mean the content gets stalled down or less involved. It’s kind of toning down this intensity in the content that it becomes a bit of an easier watch.
Alex Reynolds serves as Barrett Media’s Digital Director. In this role, he oversees all social media scheduling and content creation, monitoring of the brands analytics, and contributes to the brand’s newsletters, conferences, and websites. Originally from Rockville, Maryland, Alex is a passionate lacrosse fan, and graduate of Elon University. He can be found on Twitter @Reynolds14_.
