A scene from one of my first YouTube videos, published Jan 23, 2012
Happy Wednesday,
This week we’re doing something a little different: Jake takes over as host and interviews me about my journey as a creator—from filming skits on a family laptop as a kid, to running anonymous theme pages in high school, to the exact TikTok video that changed everything. It's the most personal episode we've done, with stories I haven't shared publicly before. Enjoy!
There was no dissonance between the thing I wanted to talk about and what did well. That was the first time I'd ever felt that way.
How I Got Here:
Age 9-10: Filmed skits with my brothers on the family laptop, edited in Windows Movie Maker, and uploaded to YouTube. The videos got fewer than 100 views, but I was obsessed with it anyway.
High school: Discovered a Wisconsin teenager running a 10,000-follower Twitter account called "I Live for Football," DM’d him, and talked my way into helping run it for free — the page grew to 150,000 followers by graduation
Freshman year of college (2017): Enrolled with the intention of becoming a doctor, got weeded out by one entry-level chemistry class, and switched to marketing — the "most analogous major" I could find to running a Twitter account
College years (2017-2020): Build a freelance social media management client base (eventually ~7 clients, a couple thousand dollars a month), including an early client, Nate Dorton, whose football brand relationship later mattered
2021: Graduate and go full-time freelance, making roughly $70,000 in my first year as a solo social media manager
2022: Partner with Jake, and the freelance work scales into what becomes Uncle Charlie, a marketing agency
Same year: Start posting on TikTok under my own name; my first videos are overstuffed with backstory about running an agency and inevitably flop
Two weeks in: Simplify to a single-topic format instead of cramming in context; my video on the Savannah Bananas leaving their league hits 200,000 views, becoming the first video where what I actually wanted to talk about was also what performed
Since then: Keep iterating on that same format, still using the same base-model Canon camera seven years later
The Big Idea: Chase the Thing With No Dissonance
The through-line of my whole story isn't really about platforms or algorithms; it's about the gap between what I was making and what I'd actually want to talk about anyway. Running theme pages, I had to write from the perspective of a high school football player I never was, or a realtor I was managing social for. Every account I ran was successful by the numbers, but there was always a translation layer between my real interests and the content itself.
@tyler.m.webb Are the @thesavbananas making a huge mistake? #sportsmarketing #sportsconent #sportsbiz #socialmediamarketing #baseballcontent
The Savannah Bananas video erased that gap for the first time. It wasn't a growth hack or a format I'd studied; it was me talking about something I'd already have brought up at dinner, and 200,000 people happened to be listening. My read on why that moment mattered more than any of my earlier successes: the work stopped feeling like a performance of someone else's voice and started feeling like an extension of a conversation I was already having.
5 Tactical Takeaways
Stack proof, don't leap blind. I've never made a big career move as a leap of faith; I built freelance income slowly and intentionally until choosing between a job and working for myself wasn't really a decision anymore, because the numbers had already made the case.
Talk about the thing, not about doing the thing. My early TikToks tried to cram in my whole backstory — my age, my business, my partner being gone — into 45 seconds. The moment I switched to explaining one topic directly, performance jumped by 3-4x overnight, and kept climbing from there.
Develop your style before you hire for it. I spent my first 30-60 days editing every video myself, which was slower and more painful, but it let me build an actual style guide — when to add music, when to zoom, when captions change color — before ever training an editor. My take: most creators struggle to find good editors because they don't actually know what they want yet.
Protect what got you there. Reading, researching, and writing still eat up my mornings most days of the week, even now. My reasoning: it's the skill that built everything else—the podcast, the newsletter, the meetings—so if that time slips, the rest eventually goes with it.
Decide in advance which experiences are "off limits" to content. I now intentionally pick certain games or events I won't make a video about, purely so I can experience them without narrating them for an audience. The split isn't accidental — treating everything as content eventually costs you the ability to enjoy anything as a person first.
Why It Matters
The most honest moment in this episode isn't the Savannah Bananas story — it's me admitting that even now, at what most people would call the "top" of short-form content, I'm chasing a new frontier: getting people to opt in and spend 20-30 minutes with me on YouTube, rather than just getting served a 60-second video they didn't ask for.
There's a version of this story where hitting 200,000 views on a TikTok was the finish line. Instead, it was the first data point in a much longer experiment about what it means to build something that's actually mine.
📩 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