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Nathan Barry

I'm a designer who turned into a writer who turned into a startup CEO. My mission is to help creators earn a living. Subscribe for essays on building an audience and earning a living as a creator.

Creating is lonely sometimes…

Hey Reader, One of the best things about being a creator is the flexibility and freedom you get to make your own schedule and work from wherever you want. You can wake up and write your next newsletter or video script on your laptop in your pajamas. But working from home can be isolating. Even if you’re an introvert, it gets lonely at times. You go to a coffee shop to mix things up, but even when you’re around people, you’re rarely around your people. The people who get it. The people doing...

7 flywheel mistakes creators make

Hi Reader, Most of us start a business to free ourselves from the restrictions of a day job. We love the idea of working when we want, where we want, and with complete autonomy. The good news with running your own business is you own all of the upside. The bad news is, you often end up creating another job for yourself. You’re stuck on a hamster wheel of requirements. You can’t actually work when and where you want because there are certain demands on you that only you can do. In an attempt...

The problem with multiple priorities

Hi Reader, How many times have you felt overwhelmed because you were juggling multiple priorities? Sometimes, we feel like multiple priorities are imposed on us—either by a boss, a manager, or just life in general. Everything seems to be vying for that number one spot at the same time. Other times, these priorities are things we impose on ourselves. We feel there are numerous things we must do and do as soon as possible. To borrow language from the Eisenhower Matrix: what do you do when...

When to write vs speak

Hey Reader, Earlier this month, I mentioned I set a goal to write every day in January. You might be thinking, “Nathan, you’re a busy CEO. Why do you need to write? Can’t you just delegate to a member of your team?” It’s a fair point. As a leader, one of the most important things I need to do is make sure I’m spending my time on things that only I can do. Then, I delegate the rest. Even if I’m good at something or I enjoy it, if there’s someone else who can do it (and do it better), I should...

3 problems creators face when scaling up a team

Hey Reader, At some point in the growth of your creator business, you come up against the upper limits of what you’re able to accomplish on your own. This is when many people hire a team. While the first few employees free you up, as the team grows, so does the demand on your time. What a lot of creators find is things start to quickly spiral out of control. Matt D’Avella shared his experience with this in a recent video: What started as a love for his craft turned into managing people,...

2023 Review: The year I learned to fly

Hey Reader, I’m excited to share my 2023 annual review with you. In 2023, I fulfilled a long-term dream of learning to fly, bought my own airplane, started a new company, bought another company, captained a 50 foot sailboat in the Caribbean, took a sabbatical, added more $7.5 million in annual revenue to ConvertKit, and had a whole ton of fun. Let’s dive in. Click below to read my annual review: Read my 2023 annual review here »​ SPONSORED BY THRIVECART​ Building high-converting pages, good...

On setting attainable 2024 goals

Hey Reader, I’m tired of telling people I’m going to write these books…” That's what I keep thinking to myself. There are five books I’ve wanted to write for a long time. I even submitted the proposal for one back in 2018. It hurts to say out loud, because 2018 was over half a decade ago. Surprisingly, no one has written any of the books yet. I figured someone would have written a book on at least one of the topics by now. But since they haven’t, that means I still need to write them. I have...

Do the verb to be the noun

This is the first week I'm sending my newsletter from a new email! If for some reason it got caught in a filter, you may need to move it to your Inbox or mark it as "Not Spam". Add this email to your contacts to make sure you don't miss future issues: [email protected] Hey Reader, A lot of people want to be an athlete without going to the gym. Or they want to be a comedian without bombing at standup. Or they want to be an author without writing every day. But you have to do the verb to be the...
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Prioritize money or audience growth?

Important: Starting next week, all future newsletter issues will come from a new email address. Please add this email to your contacts to make sure you don't miss future issues: [email protected] Hi Reader, How do you determine when to focus on growing your audience and when to prioritize making money? This isn’t to say there aren't activities that can result in both, but you usually have to choose between the two. Activities that work to effectively grow your audience typically look...
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Build skills to build an audience

Heads up: I will soon start sending my newsletter from a different email. Add this email to your contacts to make sure you don't miss future issues: [email protected] Hey Reader, The number of times I see people start a business without any hard skills is alarming. Especially the wannabe gurus teaching marketing and growth before having done it themselves. I get wanting to dive in head first and learn as you go (we all do that to an extent), but you'll have so much easier of a time—and...
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