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Tyler Webb is the co-founder of Uncle Charlie Marketing and a freelance content creator focused on sports business. Webb has over 153,000 followers on Tik Tok and 130,000 followers on YouTube. The breakdown of his sports and his business stories led to project deals with brands such as Sports Business Journal, Tick Pick, and Sleeper Fantasy Sports.
Webb graduated from the University of Minnesota in 2020 and threw himself into the world of freelance social media management after his internship was canceled due to the coronavirus. After his graduation, he connected with business partner Jake Krantz. Webb and Kranz founded Uncle Charlie His Marketing in 2021, a sports marketing agency that produces organic social content for his clients.
By the summer of 2022, Webb wanted to create social content himself, and his business partner was happy to let him. Through trial and error, he settled on a revolutionary style of creating vertical videos that entertain and inform sports fans and sports business enthusiasts.
In this conversation with BSM Digital Director Alex Reynolds, Webb talks about his video production process and why he, and social media as a whole, may be moving towards a slower approach. Please note that this conversation has been edited for clarity and brevity. For the full conversation, visit the BSM YouTube page. Click here to see previous conversations in our social studies series.
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AR: I’d love to learn more about the sports business side of content creation that you’re currently working on, but first let’s go back to the early days of the agency. What did you learn about social media back then?
TW: I learned a lot. I think the lens I was able to learn from was how to communicate what I do on social media. I’m a bit more of a purist in the sense that I like to do what I think will work. And in the early days, I wasn’t very receptive to external feedback. So it was nice to have Jake smooth out my rough spots.
At the same time, we had to recognize that when dealing with clients, there are things we need to consider from their perspective. They hand over their brand to you. In a way, this is an exercise that requires a great deal of trust. It’s a bit stupid and naive to think you know best about their brand. Maybe I’m a little overconfident. I mean, I understand, but what kind of lens are people looking at this through? I’m not doing everything for them. I am the shepherd of their brand.
Second, there are ways to improve your communication. It shouldn’t be “I’m doing it because I think it will work.” Much can be inferred from many strategies. There are better ways to communicate what you’re doing than “I’m just doing it because I think it will work.”
AR: Tell us about being independent, finding your voice on social media, and finding your way in the sports business.
TW: So I mentioned some bad iterations of content I’ve done before. I realize now that this was an afterthought and he didn’t check three boxes when he was doing something that didn’t work.
For a long time, I didn’t do anything I thought I could do. I think there’s an element of consistency that needs to be really ingrained, especially with this kind of short-form content. He might force himself to create content for a week and think, “I’m tired, I can’t do it again.” For me, sitting in front of a microphone is a much more sustainable format.
Two are things I feel qualified to talk about. Looking back at those early videos, I wasn’t the best video editor. I’m probably not even the best agency owner. So talking about these things from a position of “I know what I’m doing better than you know what I’m doing” is really It felt dishonest. That too has come through. Based on my experience, it was much more natural to talk about my general interest in sports, business, and marketing stories.
3 was a good performance. I think niche areas, especially the sports business, have been underserved to some degree. Obviously, there are a lot of people who are happy to give their opinions on the top five quarterbacks and talk about sports in general. However, I thought that the economic, financial and human benefit niche of sport was relatively underutilized. So I was able to have success with some of these videos.
I like to compare it to a Venn diagram. I sit in the middle of things that perform well, things that feel natural and entitled to me to talk about, and things that I can keep talking about for a very long time. .
AR: What about your process and what it looks like from a research and production standpoint?
TW: Research for me goes back to choosing a topic and finding an angle that I think I can work with. All that’s left to do is read. My favorite sources are Front Office Sports of the World and Sports Business Journal. I try to get as many sources as possible and collate as many facts and figures as possible.
Then I sit down and try working on the hook first. If I can’t find a compelling hook, no matter how interesting the whole story is, it’s not the video I want to make. You don’t want to be too sensational or say something completely wrong. But I think there are creative ways to convey things that are hard to believe or that aren’t true if you take them at face value, but it’s only when you watch the whole video that you understand the initial hook, he explained.
Difficulties with short-form social [content] It means you can have something super sensational or something super clickbait. People who don’t understand the context of why it’s important to them (people are very selfish when they watch) aren’t going to sit there and watch. Because they don’t believe that the information they are about to receive is correct. That applies to them.
Therefore, say something that will shock them in the first few seconds. Ask them to stop scrolling. Then say something that explains in context why it’s important to them. Next, you will need to enter your information immediately. Because if you don’t start backing up that information right away, people are going to say, “Oh, this is a complete waste of time.”
I think if the information is good, people will be happy to stay there. You keep giving them the same feedback loop of saying something sensational and backing it up. Depending on the length of your video, you may need to repeat that cycle 2, 3, or 4 times. But I think people are willing to sit for long periods of time if they can repeat and undo and repeat and undo.
AR: Tell us about the audience you found on TikTok. They come for not only fun sports-related content, but also real sports business content.
TW: I heard a quote recently: “Not all content can serve all demographics of your audience in all ways.” I have some content that I’m creating that I know will have wide appeal. Perhaps it’s just a very visual concept, and probably not a very elaborate concept. This will be a “viral” type of video that you know will appeal to the masses.
And then there are videos for my hardcore sports marketing geeks. It will probably never do as well as something with very high viral appeal. It’s not a problem. Because it is aimed at targeting a specific group of people.
I think the differentiating factor is that I have also worked in this industry. That’s where young college professionals who want to work in sports media or sports business emerge. I think the fact that I sometimes lean on that experience or use it as a backdrop for my content brings out young professionals.
People who create content about sports in general may be falling into the general fan base. Again, I’m sure a lot of my content is in the hands of casual fans, but my most loyal fanbase and the people I interact with the most also work in the industry. I realized that.
AR: Please tell us a little about your strategy outside of Tik Tok and Instagram. I also use X, YouTube, and LinkedIn, so let’s take a closer look at those.
TW: The short format stuff you mentioned (Tik Tok/Instagram Reels) just becomes a running machine. We’ve even systematized a process where we know we can publish one video a day. So for me in 2024, I’m trying to get more subscribers to my long-form content newsletter. Then there’s long-form YouTube, which is a completely different type of beat than the short-form content I create.
I’ve been active on LinkedIn for a while now and just started repurposing LinkedIn content into X. But the dirty secret is that my boyfriend’s LinkedIn content is just a reuse of the script I do for Tik Tok.
Frank Michael Smith is a truly talented creator, and in many ways I wish he were, but he always reminds me to reuse my work. . I think this will be a really good memory. Because I get caught up in my own thoughts and think, “Everyone is reading everything I put out, so this post I posted on LinkedIn is the Tik Tok I posted last week.” But in reality. It is reaching different segments.
To be honest, I think that was probably the hidden reason for my growth. I’m just poking holes in different areas of the organization, so if a young social media intern brings my Tik Tok to an executive, that executive might already be seeing what I’ve written on that particular platform. not. Across all these different platforms and mediums, I’m consistent about what my brand is.
AR: Lastly, is there anything you would like to add about your observations about the state of social media?
TW: I think we are already in this transition. I’ve heard it called FaceTime content and I’ve come to really appreciate it. The idea is that you don’t have to give your full attention to the content to understand and consume it. Podcasts are a great example; all you have to do is listen.
I’m thinking of this in the context of YouTube. YouTube has YouTube videos that you can walk away from and come back to using Bluetooth headphones. And I still get the gist of what’s going on without seeing it. Or maybe you put your phone down and you’re on the other side of the kitchen, but Tik Tok is playing and you’re listening to it.
My editing style up until now has been very unpleasant and very dependent on what’s happening on screen. I think I’m now editing at a slower pace, focusing more on storytelling and less on editing style, sound effects, and sensational visuals. I’m really trying to get back to my roots as a great storyteller. Because I want people to be able to hear and understand what I’m saying even if they’re taken away from what I’m doing.
I think there’s another element to why people feel sick when scrolling through videos. Maybe you’re a little tired, it’s late at night or early in the morning, you’re not feeling well. Maybe they don’t have the energy to watch Tyler’s three-minute video where I break down stadium urban planning. I want to make sure I have an easy watch or a watch that takes no effort. But that doesn’t mean your content is stagnant or diluted. This intensity of the content has been toned down a bit, making it a bit easier to watch.
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