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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.

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Featured Post

How my passion project became a time drain

Hey Reader, Remember when you first started your business and it felt like a game? You couldn't wait to wake up and work on it. Now it's just constant stress and putting out fires. I felt this way about my podcast. I love having deep conversations with creators I admire, but the weekly production was taking over my life. As the CEO of Kit, I spend most of my time building and growing the company—I couldn't dedicate entire days every week to podcast recording. Something had to change. I needed...

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Hey Reader, If you're reading this, you probably have years of expertise in your field. You see inefficiencies everywhere that you could fix. Creating a course or consulting service to share what you know feels like the logical next step. But here's what happens when you start building: You spend months crafting your course or service, polishing every detail. Then you try to find people who want to buy it. This approach puts you in the position of convincing people they have a problem rather...

Farmer to horse: “You won’t lose your job to a tractor, but to a horse who learns how to drive a tractor.”

Hey Reader, What happens when AI gets better at what you do? You've probably heard people say, "AI won’t take your job, but someone who knows how to use AI will." I actually think AI will take your job. And mine too. But more on that in a minute. I mentioned a couple weeks ago that there are no more long careers. Careers used to last a lifetime. Now they might be more like 10 months. So how do you make yourself valuable at work? More essential? No matter what role you're in, you need to think...

Hey Reader, I used to be very consensus driven. Every decision at Kit required input from everyone. I'd collect opinions in endless meetings, because I care about harmony and making sure every voice was heard. The problem was nothing was getting done. My coach asked me one question that changed everything: "If you were CEO, what would you do?" It sounds simple, but it hit me like a truck. I am the CEO, yet I was acting like I needed permission to lead my own company. I realized I'd been...

Hey Reader, Careers used to last a lifetime. Then they dwindled to 10 years. Now it might be more like 10 months. If you're young and starting out, this reality can feel overwhelming. What advice can possibly make sense in a world that's changing this fast? This is something I think about a lot with my oldest turning 14 in a few weeks. What career advice should I give him? Focus on what doesn't change Jeff Bezos built Amazon on this principle. He knew that no matter what technology emerged,...

Bookshelves are overflowing with colorful books.

Hey Reader, You ever wonder how some people just seem to speak in perfect soundbites? They always have the right thing to say, delivered in exactly the right way. At our Craft + Commerce conference this summer, Tristan de Montebello from Ultraspeaking taught something called "The Accordion Method"—a technique for learning to speak this way by compressing your thoughts down to 30 seconds, then expanding them back up to 2 minutes. Watching creators practice this made me think: Most of us are...

Close-up of an old typewriter's keyboard keys.

Hey Reader, In last week's issue on how AI fixes what I won't, I touched on how AI transcription is getting so good that I talk more than I type these days. Today I want to go deeper on my actual writing process with AI. My three-tool setup When I'm writing anything substantial, I open the same three tools every time: Google Docs Claude NotebookLM Then I start talking instead of typing. I use speech-to-text software—I share the exact tools I use below. The back-and-forth process Once I have a...

A white keyboard sits on a wooden table.

Hey Reader, For someone who considers himself a writer, I'm embarrassingly slow at typing. I can type, but I'm not fast. I still look down at the keyboard more than I should, and I've never developed the muscle memory that proper touch typists have. It's been this way for years, and I've always told myself I should learn to type properly. But now I don't have to. I use an app that lets me hold down a function key and speak my thoughts. What comes out is perfectly punctuated text—complete...

Hey Reader, Most people consume content their entire lives but never create any. There's an unwritten rule that explains why some people build influence while others stay invisible. I call it the 1% Rule of content creation. 90% of people just consume 9% actually do something Only 1% document the journey and share what they've learned That final step—documenting your journey—is what separates those who get things done from those who build leverage through an audience. My friend Delphine Le...

Craft + Commerce: 7 years to overnight success

Hey Reader, In February 2017, Barrett Brooks and I had a crazy idea: We should start the best business conference for creators. Each of us had our own careers transformed by who we met at conferences. The right event led to the right connections, which would accelerate your creator career by years. I wanted to create that opportunity for every creator in our community and there wasn’t an event that blended business strategy, connection, and inspiration. At the time, we were a software company...