The Biggest Mistake Creators Make as Entrepreneurs

In this video Matt Ragland explains that the single biggest mistake new creators make in their first year is hesitating to sell a product. He argues that fear and inflated expectations about product size and price cause creators to delay launching, which stalls growth. Ragland offers a concrete framework: develop a small, under‑$100 product that delivers a clear, specific outcome and can be built in 4‑6 weeks. He shares multiple real‑world examples—a Bullet Journal basics mini‑course, a resume‑writing course, a UX portfolio workshop, a file‑organization workshop, and others—to illustrate the approach. He emphasizes that early, low‑ticket sales teach creators how to sell, validate market demand, and build confidence, whereas aiming for high‑ticket, cohort‑based courses too early leads to disappointment. Ragland also outlines his own product‑launch experiment: a 3‑month Simple Path Productivity membership, and discusses how he set progressive revenue goals tied to personal expenses (e.g., covering side‑hustle costs, groceries, mortgage). Throughout, he encourages creators to start small, iterate, and align product ideas with both audience needs and personal profit goals. The video ends with calls to share product ideas in the comments and to join his email newsletter for further productivity and profitability guidance.
Chapters
There's one big mistake that I see most new creators making in the first year of building their business. When I started my digital creator journey as a blogger in 2011 and then became a podcaster in 2014 and then became a YouTuber in 2017, I still kept making this mistake year after year. There was one big shift that I made in my business, in my side hustle, in my life that allowed me to go faster in that year than I had in about 10 years before. It's the biggest mistake that I see new creators making and something that can hold you back from going full-time on your dream business for years. Hi, my name is Matt Ragland, and I create videos that help you be more productive and profitable using simple systems so you can focus on the people and projects that matter the most in your life. The biggest mistake that I see new content creators make in their first year of building a side hustle or building a business is the hesitancy to actually sell a product. I do think there are a lot of really good reasons that people wait to pitch and promote products like audience building, making sure you're dialed in on niche, making sure that you have product-market fit. Those are good reasons to wait, but usually people wait because they're scared. They have inflated ideas of what a product should be. Maybe they see what types of products they've purchased in the past and think, well, I have to have a cohort-based course or I have to have this $10,000 coaching program. None of those things are actually true when it comes to selling products. Between my work with creators at ConvertKit and Podia and now the clients that I work with through my agency, 1K Courses, one of the things that I'm always encouraging people to do, no matter how early you are in your audience building or your content creating, journey is to start to build and promote and publish and sell a product as soon as you have any kind of idea about something that you want to test a product idea on. The way that I help new creators develop products is by giving you a framework for creating a relatively small, under $100, very clear outcome of a product for your potential customers. This lets you test and experiment with a few different product ideas in a relatively short amount of time. The thing that helped me get over the hump financially with my side hustle in 2020 was by developing and shipping a new product every month for 6 months. At the end of that 6-month window, I had 6 different products that I could promote throughout my audience and my newsletter and here on YouTube. But it also gave me a good idea of what types of products were people buying and how could I do more of those in different ways in order to continue to build my business and eventually go full time as a creator. Because while the biggest mistake new creators make is not selling any products at all, the biggest mistake that people make while creating products is by trying to do too much with their first product. They think that it has to be this cohort-level course, or they think that it has to be this big coaching program. And neither of those things are true. What I have found, what has been most successful for me and most successful for the creators that I worked with at past startups and now with clients, a specific outcome of a product, something that you can put together within a month and is less than $100 for potential customers have a product they can commit to and something that you can learn from. Maybe it becomes a cohort-based product. Or maybe it just stays small that you can then sell, you know, over and over again through your email newsletter, on a YouTube channel, a podcast, through social media or anything. I just had a few minutes of really great content, but I hadn't hit record yet. So third time's a charm because I had already done it a second time. Third time's a charm. So you may be asking yourself, Matt, what do you mean by a small, specific outcome under $100 course? So glad you asked. I have a few examples for you. So because the bulk of this channel has been built on the Bullet Journal, I created a Bullet Journal Basics mini course. So it helps you set up your Bullet Journal, see some easy to use layouts, understand how to set things up, how to keep things minimal and consistent, how to build the habit. So it's a very small, specific course. It's actually under $50 that will help you have a specific outcome. You have set up a Bullet Journal and you have a habit of continuing to use it. Another one that I'm working with on a 1K Courses client is Michelle, who has created a resume writer course. It helps you write a better resume so that you can get the job of your dreams. Another one is with Jamar, who is doing two products at once, and the first one is to help brand new UX designers build their portfolio. And then once you've built your portfolio, kind of the next step is people who have that portfolio know how to work on the design challenge within the UX interview and basically how to ace the interview overall. Another one that hasn't been built yet, but I'm pushing on him. So Ed, I'm looking at you with this. Ed has a cool idea for a mini course, or it even could just be a workshop. He has an idea of helping people fix their file structures in their computer. If you're like me and you have like 1,000 files in your downloads folder, and another 1,000 files on your desktop and nothing is named properly and it's hard to find things. Ed has a really good file taxonomy system that he helps walk people through. And I'm talking to him like, Ed, this is a course. You could do a workshop on this. It'll help clean up people's computers and they'll be able to find things easier. That is a small, specific outcome of something you could do in a relatively short amount of time. That would help people with a specific outcome of having a better resume for your job interview, of building your UX portfolio, of cleaning up your computer files so they're easier to find, to help you set up your bullet journal, to help you create and publish your first 10 videos on YouTube, to help you create a daily writing habit and publishing habit on Twitter with Ship 30. You can see how each of these examples are relatively small specific outcomes that you can give readers, viewers, listeners, subscribers in order to help them. This is the really big part. You can do this from the beginning as a new creator because not only does it give you the confidence of being able to sell, it will help you understand what types of products are most useful to your audience. It also creates an expectation. For the audience itself. Like Matt has a business here. You want to make the outcome something that is very beneficial for your subscriber, for your potential customer. I want to create things that give a specific outcome and something really helpful to you to help you solve a problem or achieve something in your life that feels just out of reach. The other reason this is so important for new creators is because you don't become better at sales by reading books about sales. You don't become better at sales by watching courses or taking classes or listening to podcasts about sales. You become better at sales by making sales and learning about what works and doesn't work about each sale. One of my favorite quotes is by a Franciscan priest named Richard Rohr. He says, we don't think ourselves into new ways of living, but we live ourselves into new ways of thinking. I don't know if you expected to hear a priest quoted in a video about developing, publishing, promoting, and selling digital products, but it's an important application. Like, I think it really carries into this mindset of how you're going to create things and sell them to people, and that it's okay to do that because I don't believe that you become better at sales and making money and developing products by just reading books and taking courses and listening to other people tell you about how to do those things. It helps, but what will help you the best is by actually doing the thing. The other reason that I encourage people to start relatively small with under $100 products that you can develop in 4 to 6 weeks is because I have experience and I've seen so many creators pour 6 months of their lives or more into a course and price it at $500 or $1,000 expecting that they're going to sell 100 of them and it's going to change their life and they're going to make $50 grand in a weekend. I know I have gone into launches thinking this is going to be it. This is going to set me up for the next 6 months to a year. This is going to change everything. I'm going to be able to quit my job and I make $10,000. $5,000, $3,000. And while you may be listening to that thinking, hey, $3,000 sounds great and it is, but if you go into a launch hoping for $50 and you get $5, I'm telling you, it feels pretty devastating even though the money is still nice. What I would rather see you do is become confident through selling 10 $50 products over the next year. And understanding these products sold really well. I did some as a membership, I did some as a workshop, I did some as a course, I did some as an ebook, I did some as a coaching program. There are all these different things that you can do and all these different ways of developing and positioning products. What do you enjoy doing? What does your audience enjoy learning from you? Where is that convergence between what you like doing what your audience likes learning from you about and where you can be the most profitable. Like, what's that kind of Venn diagram? I'll let you know that my next product experiment is a 3-month Simple Path Productivity membership that's going to go November, December, January, the 3 most productive months of the year. And you're going to have access to the core lessons of everything that I've developed about productivity over the last few years. There will be once or twice a month Q&A or expert workshops or things that I'll teach you about. So there are these 3 months that I'm going to create a membership around, and I've never done a membership before. And so I'm excited to see what that experiment is going to be like and how you engage with it, because everything is a test. And if it goes really well, maybe we'll have a full year membership going into 2022. If it goes okay, then that's, that's fine. I get to decide that, but I will have made that experiment. It'll be relatively low impact for me because it's only 3 months instead of a year, and it'll be relatively low cost for you, for you, because you get to be a part of the experiment with me. One last thing about building revenue and profit into your product experiments. Of course, the thing that is a little challenging about starting on relatively low-priced products under $100 is if you're looking at something that you need $10,000, $20,000, $50,000 to quit your job and go full-time. And if that's something that you want to do, then $100 products will take a little bit longer to get there. Again, it all depends on where you are in the journey and your timeline. All that kind of changes how you price things as well. And shoot, if we work together, I can help you get into that. What I did early on in terms of revenue goals that I had for my side hustle was matching it to expenses that I had just in normal everyday life. And so the first goal that I had when I was creating products was I have about $200 of side hustle expenses between different platforms, products, different things that I was buying. So I was trying to make $200 a month to match my side hustle expenses. If that, that was a good milestone for me. The next one was Okay, can I make, say, $800 to $1,000 a month and replace the groceries that we buy? We spend a lot of money on food. We got 2 boys. I don't know what to say. I can't get it any lower than we do. It's whatever. But it's, can I get to $1,000 a month to basically replace our food budget? And then it was, can I make enough money to replace our mortgage? And now it's, you know, it's all of those things, of course. But think about how you can tie your side hustle revenue or profit to a specific real-life thing that you're either replacing or getting to do on top of normal life that feels really fun and special to you, and it will make your product development a lot more fun and special as well. I want to make $5,000 this year so that I can take us on a really kick-ass vacation. If you have a product idea for your business or side hustle, drop it into the comments below. I'd love to give you a piece of advice that will hopefully help. And if you want to know more about the community that I'm putting together, the content that I'm creating in my weekend Connect the Dots email, everything that I'm doing and how I can help you be more productive and profitable using simple systems. Make sure you join my email newsletter. There's a link to it in the description below. And that's one of the best ways that we can stay in touch. Hope you have enjoyed the 2 videos a week cadence that the channel's been on. Thanks so much, everybody. Bye.
More from Matt

Journal reading 📖 Reflectjons on how I’m living & how it aligns with the vision I have for my life.

You don’t have to listen to me. But you do have to be intentional about the systems in your life.








