In this personal monologue, Matt Ragland recounts his journey from quitting his corporate job at the end of 2020 to navigating early creator success, financial strain, and tax panic. He describes three years working with former coworker Darryl Vesterfelt at an agency, where he learned sales, marketing, operations, and finance, eventually raising his minimum project price from under $2,000 to $2,000‑$3,000. Over that period, family growth (four children) forced trade‑offs that led him to deprioritize his YouTube channel—a regret he now seeks to rectify. After a tax mishap that cost him $30,000 in estimated payments, he realized the value of professional tax help. Entering 2025, Matt aims to shift his business model away from client work toward creator‑driven revenue streams—Hey Creator community memberships, courses, sponsorships, and his own media properties—targeting a 50/50 or 60/40 split between client and creator income. He expresses ambitions to expand his personal brand, appear on high‑profile podcasts, and reach a larger audience, while committing to share his ongoing successes and failures transparently with viewers. The video ends with a call to subscribe and follow his journey.
Chapters
This is a video about making big changes, even when they're scary. And even when you're not sure what the outcome is going to be, even though it's a thing that you want really bad, and it's something you feel like you're meant to do, when it hasn't quite worked out the way that you wanted, but you're not ready to give up just yet. This video is for you, because this video is for me. Here we go. I quit my job at the end of 2020, which is a very interesting time to quit a job and go out on your own. And over that next year, I did okay as a content creator and a creator consultant. Really what happened at the end of that year was that the first 6 months of 2021 went really well, and then the last 6 months of 2021 didn't go as well. But I had basically already spent all the money that I made at the first 6 months. And so I was getting to the end of the year and I basically didn't have any money. And I had 2 kids and a third on the way. And I was like Will Arnett in Arrested Development. He's like, I've made a terrible mistake. So I started working with a friend and former coworker, Darryl Vesterfelt, and joined his agency. And that was really great for me because I learned a ton. I worked with Darryl for the next 3 years. And I learned a ton about sales and marketing and operations and finance and how to think bigger and how to make more money and how to book bigger and bigger clients than I ever thought was possible. When I first started working with Darrell, doing anything for a client for more than $2,000 felt extravagant and very difficult to do. And now a few years later, like, I basically won't do anything for less than like $2,000 or $3,000. And the amount of work that I was willing to do for $2,000 3 years ago at the end of 2021 versus the amount of work that I'm willing to do for $2,000 now is very, very different. And so I learned a lot and did a ton. But one of the things that I sacrificed over the last 3 years, and you know, when you're a part of a company, there's always going to, there's always going to be some type of sacrifice, you sacrifice yourself for something. For something bigger, to be a part of a business, an agency that you hope the sum of all the parts gets bigger and bigger. And one of the sacrifices that I made is that I just didn't put as much time into my YouTube channel specifically. And that is something that as I look back, it's really the only major regret that I have over the last few years. And it's not so much an either or of working on the agency or working on the YouTube channel. It was that not only did we have our third child, but then last year we had our fourth child as well. So for me, it's always been this like understanding of time commitment and what I'm willing to do. You could even say trade-offs in a sense of like, well, I could spend 8 to 10 hours a week also working on a YouTube video, or I could sleep 8 to 10 hours more in total. I could spend more time with my family. And that's pretty much what I always decided to do. But after our daughter was born and the last few months of 2024, I really started to feel a calling and a pull to get back to what I was doing as a creator. Like I said, I've learned so much more about how to make money and how to manage that money and cash flow as a business owner. Quick little, quick little aside, after that first year, the other thing that was horrible for me is that I didn't make any quarterly payments on my taxes. And so when I— and I was also doing the taxes on my own. And when I went to like calculate the payment for 2021, it said I owed $30,000 and I didn't have $3,000. And I was like in a complete and utter panic until I talked to my dad, who's a tax professional. And why I didn't use him at the beginning is another story for another day. It was all my fault because I just wanted to prove that I was like smart enough to do taxes, even though that's literally what my dad does. But we're not going to talk about that right now. That was all on me. So, you know, my dad did taxes like a professional, and it turns out I didn't owe that much money. Surprise, surprise, tax professionals are worth it. And so going into 2025, I feel much more prepared for more like solopreneur, small team type of work. But the thing that I also don't like, I don't have a consistent, you know, guaranteed partner payment anymore. What I make every single month is what I can generate either through products or sponsorships or clients or coaching, consulting. Those all kind of fall into the same bucket for me. The other thing that I wanted to put more and more time into that I was kind of putting less and less time into the latter half of the year is the community that I started, you know, with Derral and some other people called Hey Creator. And many of you watching probably know what Hey Creator is or are members in it. And yeah, I appreciate it and I appreciate all of you, but I was spending a little bit less time with Hey Creator and it became more and more apparent to me just as I thought about it and journaled about it and prayed about it and talked about it with my wife and other, other friends and mentors was that my desire going into 2025 was to spend more time creating and more time helping creators directly through the Hey Creator community. And what I wanted to focus my time on was YouTube channel, newsletter, creating things and then sharing with the community. The types of ways that I was creating, like connecting with others that I've built a strong network with over the past several years and bringing them into the community. There were just more things that I wanted to do because I realized in the second half of 2024 that when I'm not making things, when I'm not creating myself, then I feel less inspired to like teach others and coach them in their own creative journey. And that's what I, that's what I really want to do. And so I took a big step back from client work. Daryl is doing, you know, Daryl and I amicably went in, in our separate, separate ways. We're still like doing, doing some projects and working on some things together, but he wanted to work with more companies and more like founders. And I really like working on my own creative projects. And again, like this, the, the beginner to intermediate type creator through, through the Hey Creator community. And this is very exciting for me, but it is still, like I said, like very unnerving because starting January 1st, I didn't have any guaranteed payments coming from anywhere. I either had to work with a few clients, which, you know, thankfully I am. And there is like, how is the Hey Creator community going to grow? What kind of sales can I make to courses and products through my own email list? What kind of sponsorships or brand deals can I get through my YouTube channel? How do I prioritize all of these things? Because what I thought about, which is kind of a surprising thought to me, is I'm not as concerned about making money this year. I believe that through client work and some product course sales and sponsorships, I feel good about making the same or like actually quite a bit more than what I made last year. The question is, and this is part of the commitment that I'm making to myself, and what I'm really striving for at the end of 2025 is I don't want— because right now the majority, I would say like 70% of my revenue comes through client work. By the end of 2025, I want that to be at least half and half, if not like 60 to 70% through the Hey Creator community memberships, through course sales, through sponsorships to my YouTube channel and other like media properties, if you want to call it that. So it's really focusing more on like my own creative output as the driver of revenue instead of operational consulting client work where I'm still like trade— trading time for money through clients. And it's a good, it's a good bit of money, which is, you know, why it's, why it's great to do. And I have incredible people that I get to work with as clients, and I have some flexibility around that, which is the kind, the kind of life and the kind of business that you want to build. But still, I, I want to focus my work and my creative output around things that I'm making not necessarily things that I'm making on the behalf of others. And that might sound, I don't know, it might sound a little delusional. It may sound a little bit like, well, you know, I, you know, I want to be like internet famous. And like I always say, I don't know what level of internet fame I want to be yet, but I want to be more well-known than I am right now. And I believe that I can do that. And that is like some of the first times that I'm admitting to myself, like I've I've been able to work with and consult with some, some really incredible, like, clients and people that you, you would recognize, uh, that I've worked with. Like, one that said, like, I've done some work with Ryan Holiday and his team, and I really enjoy working with them. They're great, and he's very inspirational, and I've learned a lot from, from them. But here's the thing that I thought about, was like, I I don't just want to like help Ryan with his emails and some of his launches. I want to like be on Ryan's podcast. I want to be like, hey, here's Matt who has done these things and this is awesome and I'm excited to talk to Matt. I want to be on the Tim Ferriss Show. I want to like be one of those people that other like other creators, other entrepreneurs on that level are excited to connect with. With is up to this point, and maybe this is a limiting belief on my end, and maybe it's something that like I like have like think, don't think enough of myself subconsciously, but like I don't want to just be like, oh yeah, we'll talk, talk to Matt, he will take care of your emails for you, which I can. And I've, I've done very well about that. But I also want to be like, hey, Matt has a top 10 podcast. Matt has 1 million subscribers to his YouTube channel. Matt's email list has 200,000 people on it. That's what I'm talking about. That's the direction that I'm going for all of this. And so the challenge is not about making enough money in 2025 and beyond. I feel confident about that. I don't think I've ever felt confident about my ability to make enough money. So thank you, Darryl, and everyone else to help instill that money confidence in me. What I want is to grow the brand, the mission, the things that I feel really excited about, and bring those to more people in the world and have that, have that platform to share with others. That's what I'm, that's what I'm moving towards. It's not just like, hey, can I hit a revenue number? Like, I have a revenue number, I feel good about hitting that, but it's like, what kind of reach can I have? How can I promote a mission that, that I, that I'm working in? How can I have the majority of my revenue come from things that light me up, that I'm excited to do every single day, that like help me scratch that creative itch. That was the reason that I got into all this work in the first place. So this channel for the rest of the year and for the foreseeable future will be my journey and my lessons and the things that I'm doing as a creator to grow the Hey Creator brand, to grow my YouTube channel, everything that I'm learning and experiencing. The struggles and the successes of that journey. You're going to learn just by seeing me fail and succeed. So subscribe, ring the bell in the YouTube sense. This is going to be a fun ride, and I hope that you join me for it. See you in the next video.
