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.
3 questions that changed how I think about money
|
Hey Reader, If you want to understand how someone thinks about money, ask them these three questions. I've used these in presentations, in one-on-one conversations, and on myself. The questions are simple but the answers usually aren’t. Here they are: Question 1: What's your earliest memory related to money?A while back I asked this of my in-laws. We were all hanging out, and my mother-in-law and her older brother started sharing memories from childhood of selling produce door to door. It sparked a really fun conversation and reminded me why I love asking it. You can often find the money stories people tell themselves in those early memories. Many times these are beliefs they never examined that now inform the attitudes they have about money. Question 2: What situation made you say "that will never be me?"For me, the earliest memory and this question have the same answer. Growing up, I watched what financial stress does to a family. I wrote about that specific memory last week, so I won't retell it here. But it stayed with me for a long time. There's a saying that goes, "Chips on shoulders put chips in pockets." Having a chip on your shoulder means carrying a wound that drives you. For years, that's exactly what I did. This question is usually the easier one to answer. People can usually point to a situation without much hesitation. Question 3: When did you see something and think: that could be me?My answer is watching two designers, Sacha Grief and Jared Drysdale, launch design eBooks on the same day to small audiences and make tens of thousands of dollars. I'd seen people like the Basecamp guys make good money because they were operating at a big scale. I thought of course they could make a quarter of a million dollars. But Sacha and Jared weren't operating at a huge scale. They were people I could relate to personally. Watching someone make good money with a small audience changed something for me. It made things feel possible in a way that watching big operators never did. That's what took it from an interesting anecdote to thinking maybe I could do something like that myself. It's also one of the reasons I wrote my book, The Ladders of Wealth, which is coming out later this year. — I was talking through this with Mike Brown, who was a guest on the podcast in the episode that's publishing next week. We got into the idea of clean fuel vs dirty fuel. Clean fuel is motivation rooted in purpose or something you're running toward. Dirty fuel is motivation rooted in fear or pain or something you're running away from. Both can produce results, but they come from very different places. The second question points to your dirty fuel. The third points to your clean fuel. Do you know which one you're running on right now? PODCASTAI Expert: How Your Business Can Survive AI in 2026Dan Cumberland helps creators and entrepreneurs set up AI systems that remove friction and free up time for the work they actually care about. In this episode, we get into what it actually takes to keep your business competitive as AI changes things. Dan covers the mistakes that leave creators vulnerable and how to build portable context that works across every tool you use. The people who get this right now will have a big head start on everyone still duct-taping AI onto their existing workflow. Watch or listen to episode » VIDEOHow to Introduce Yourself So People Actually Remember YouIntroducing yourself well is one of the highest-leverage skills you can build as a creator, and most of us were never taught how to do it. Clay Hebert gave this talk at Craft + Commerce 2025, and people loved it. After an embarrassing introduction to WordPress founder Matt Mullenweg, he spent years researching what actually makes introductions work and built a simple framework that makes people curious and opens doors. You'll learn:
Watch the full talk below. And once you've got your intro down, come use it at Craft + Commerce this June in Boise. We sold out last year, and this year about to sell out again soon. Get your tickets to Craft + Commerce » X POSTHonest take from DHH on working with AI agentsDavid Heinemeier Hansson, creator of Ruby on Rails and co-founder of Basecamp, has been working through what AI agents actually look like in practice and shared some good notes from the process. The big thing he talks about is moving from task-based instructions to outcome-based ones. And he makes a case for giving agents more trust and less babysitting—as long as your machine is easy to restore if something goes wrong. Worth reading if you're thinking through how to work agents into your workflow. Have a great week! —Nathan |
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.
Hey Reader, Two of my best sales conversations this year almost didn't happen because I talked myself out of starting them. Emma Grede, who cofounded Skims with the Kardashians and built Good American, has a podcast that's exploding. But her husband is also an investor in one of our biggest competitors. So I wrote her off. I assumed the investment meant she'd never move to Kit, so I never reached out. Then Samir, from Colin and Samir, texted me out of the blue. His team wanted to move their...
Hey Reader, One winter morning when I was twelve, I sat at the kitchen table eating cereal, staring out the window at the largest snowflakes I'd ever seen. Every other kid in Boise was sledding. I was homeschooled, which meant no snow days. My mom spoke up: "You know, Nathan, school doesn't have to take a set amount of time. The sooner you complete your work, the sooner you can go sledding." Two hours later I was on the hill. That morning I understood something I carried with me for years. I...
Hey Reader, A lot of the rules we built our work habits around made sense before AI. Some of them held up for decades. Right now, in early 2026, I think it's worth asking which ones still do. Here are five things I think are worth throwing out: 1. Detailed mid-level planning Knowing where you're going is still important. But the master plan that used to live between the destination and the work itself is mostly just a way to delay starting. Before, mapping out how all the systems connect just...