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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.

Balance being a CEO with being a good husband and father

Hi Reader, “Did you still make your 12 year old milk the goat at your farm before you go to the airport to fly on a private jet?” “Yes, actually,” I said. My friend was giving me a hard time, but his joke is somewhat relevant to what I want to talk about today. Someone asked how I balance being the face of a company, and being CEO, with still being a good husband and father. It’s a good question, but it begs another: what is a good husband and father? The answer will vary depending on who you...

How to parent entrepreneurial kids

Hi Reader, My first entrepreneurial pursuit was pet sitting. I thought getting paid $10/day to feed someone’s cat was fantastic. I couldn’t believe someone would go away for a week and I could bike to their house and make $70. It felt like magic. Not all of your kids will be entrepreneurial, and that’s okay. If they are, expect each of them to express their interests differently. Go with their energy Pay attention to the times your kid says they want to do something and you start to say, “Oh,...

Should you record in person or virtually?

Hey Reader, I wrote recently about how meeting people in person changes everything. You can accelerate relationships more in a few days than you would in six months to a year of talking online. But not only is meeting in person great for memorable connections, it’s also invaluable for podcast recordings. Podcasts recorded in person perform so much better than podcasts recorded virtually. Ryan Holiday was telling me clips that are recorded in person perform 40–50% better than virtual...

Behind the scenes of the busiest week of my career

Hey Reader, One of the things I love about working from home is I don’t have to worry about a long commute. My wife and kids are just a few steps away. While I love to travel, I don’t want to travel so much for work that I miss getting to see my kids grow up. This is what motivates me to maximize my time away from home. If I have to be away, I want to make the most of that time. That means meeting as many people, and creating the greatest number of opportunities, as I can. Last November, I...

Go on a public quest

Hi Reader, I’m a big fan of working in public. I don’t just mean taking your laptop to a coffee shop (although I love doing that too). I mean in a figurative sense: showing your work as you go, sharing the process, and letting other people in on your progress. But beyond just showing your work, share where you’re going. What are your ambitions? What’s your aim? What is it you want to achieve? Danny Miranda loved watching basketball as a kid. He idolized Kobe Bryant’s relentless pursuit for...

Write to one person

Hey Reader, Tom Brady focuses on football and nothing else. It’s his life. He dreams about football, studies it, obsesses over it, and dedicates himself to getting better at his craft. His manager, Ben Rawitz, was surprised to find that Tom really did not pay attention to anything else. “Did you see the news?” “What news?” Tom said. There was a big story that had broken, and Ben thought surely Tom knew about it. Nope. He was focused. That’s when Ben decided to start sending an email to Tom...

Stay flexible. Stay agile.

Hey Reader, When things are going well in your business, it makes sense to double down and invest in doing more of what’s working. You’ve seen this with creators running YouTube channels that are doing well. All of their peers have large teams of people supporting their content creation, so the natural thing to do when you come into some money is hire a large team. On the surface, it seems reasonable: if content is how you make your money then hiring more people would help you make more...

Spend time with customers

Hi Reader, If you want to have a great product, you need to do two things: Use your own product Spend time with customers When’s the last time you signed up for your own software? Or purchased your own product? What is the onboarding process like? What is the purchase experience like? What does it feel like to actually use the product? If you don’t ever use your own product, you will quickly become removed from the actual experience people have. Part of the reason I write a newsletter is...

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...
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