When to Quit to Become a Creator 👋🏻

Happy Wednesday,

Matt King is an NFL content creator who, last November, made the jump from a full-time job to doing content creation full-time.

Full disclosure: that full-time job was here at Uncle Charlie, working for Jake and me.

This week, Matt came on to walk us through exactly how he made that decision: the numbers he needed to hit, who he talked to, what surprised him most, and what he'd tell anyone thinking about making a similar leap.

🎧 [Listen to the full episode]

Consider this: most people treat their full-time job like a guarantee. The paycheck hits automatically, the benefits are there, and the whole thing feels stable. However, Jake's argument (and I think he's right) is that it's a false sense of security. Companies go out of business, revenue drops, and teams get cut. You stop performing, and you're out. The stability you feel is real until it isn't.

Meanwhile, the content creator economy is at a genuine inflection point. More money is flowing into the ecosystem than at any point in its history through:

And unlike a W-2, when Matt loses a sponsor, it stings, but it's not 100% of his income. However, when someone loses their job, it is.

Now, there are obviously several downsides to earning your money this way, the least of which is the fact that being a content creator actually means you have multiple bosses, not zero (like people might believe).

Every brand you work with has expectations, timelines, and the leverage of not paying you if you don't deliver. The boss-free lifestyle is real in the sense that nobody tells you what to work on. It's less real when you're answering to five sponsors at once, each of whom thinks they own a large portion of your time.

1. Set a number before you make the leap (and be specific).
Matt didn't quit when his content income matched his salary. He quit when it exceeded it by $10,000. His reasoning: if it's the same amount, you can always tell yourself you're making full-time job money on top of content money. The extra $10K made it unambiguous: he was leaving for more, not just matching what he had.

2. Recurring sponsorships are the floor, not the ceiling.
Platform payments fluctuate, and one-off deals come and go. What gave Matt the confidence to jump was locking in sponsorships that ran through the rest of the year and showed signs of continuing. The goal isn't to make a lot of money once, it's to build enough recurring income that a bad month doesn't feel like a crisis.

3. Keep your cabinet of advisors small and specific.
When Matt was deciding whether to make the leap, he consulted three people: Jake, me, and his wife. That's it. His parents didn't understand it. Most friends couldn't relate to it. The people worth consulting are the ones who actually understand your specific situation instead of the ones who will give you generic advice about job security and benefits.

4. Viral growth can be a trap.
Matt's "football over the house" series blew up his account, but then it created a problem. For months afterward, new followers showed up expecting challenge content. When he went back to NFL analysis, they left. He wishes he'd built his audience more slowly around the content he actually wanted to make. The short road gets you there faster; the long road gets you there with the right people.

5. The hardest part of the job isn't the content, it's the distraction.
Matt said this, and I felt it immediately. Once you go full-time, you see everything other creators are doing and immediately want to do it your own way: a newsletter, Instagram stories, a new format, a new series. The discipline isn't in making the content, it’s in telling yourself you don't need to do every shiny new thing you see working for someone else.

The part of this conversation I've been sitting with isn't really about Matt, it's about what his situation says about where the creator economy is right now.

Jake and I knew this was coming. We watched the writing on the wall for months. Matt was putting more and more time into his content, making more money from it, and at some point, the math just stopped working in the direction of staying. We weren't pushing him out. We were watching someone cross a threshold that, once crossed, is pretty hard to uncross.

And I think that's just the reality of running a creative business right now. If you hire talented, ambitious, creative people, some of them will eventually realize that they can do this on their own. The content creator economy has made that possible in a way it just wasn't five years ago. That's genuinely exciting and also genuinely something every creative business owner has to reckon with.

Matt's dad came up to Jake and me at the wedding a few months before any of this happened and said, "You're Matt's boss? Just keep paying the man." I remember feeling bad in the moment, because I could already see where this was heading.

Still, I’m glad he made the leap.

🎧 [Listen to the full episode]

📩 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