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.
Don’t reject yourself
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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 email list to Kit. He's also an investor in another competing platform and runs his newsletter there. And I assumed the same thing about him—that it probably wasn't worth asking. Both of those assumptions were wrong. When I was in Dubai earlier this year (watch the vlog), I ended up in the same room as both of them. We had conversations that wouldn't have happened over email, and both relationships moved forward quickly. Emma's team is now using Kit to promote the launch of her new book, Start With Yourself, which just released today. And Samir's team has migrated their list. I nearly missed both of them by rejecting myself on their behalf. There's a version of rejection that comes from other people, and there's a version that comes from yourself before you give anyone else the chance. Watch out for the second one. It’s easy to think that they’re probably happy where they are or, because they invest in a competitor, it’s not worth reaching out. But you don't actually know any of that. And you shouldn't make that decision for them. A few things I'm carrying forward from this:
Another thing to keep in mind is, even if you’ve asked and gotten a no in the past, that's not a no forever. If someone said no two years ago, ask again. Things change and they might say yes now. The next time you talk yourself out of reaching out, ask whether you actually got a no or if you just assumed one. If you assumed, let them decide. That's their job. PODCASTThe Exact Systems Behind a $1m YouTube ChannelTintin Smith spent two years as Ali Abdaal's head of YouTube, helping grow the channel from 3 to 6 million subscribers and $5 million in annual revenue. Now he helps educational YouTubers turn their audiences into businesses. In this YouTube business masterclass, we break down exactly how to monetize a YouTube channel. We cover:
Watch or listen to episode » CONFERENCECraft + Commerce 2026 will sell out soonEvery June, several hundred creators come to Boise for Craft + Commerce, Kit's annual conference for creators. I started it because I wanted a place where serious creators could be around other people who are building the same kinds of things they are. Every meaningful connection I've made in this industry has come from showing up in person. That's why we host this conference. The people you meet here are the ones you'll still be talking to years from now. We've already sold most of our tickets and the conference is two months out. If you're thinking about coming, get your ticket today. This one will sell out. VIDEO45 Days with MrBeastJon Youshaei shared a fascinating documentary going behind the scenes of what it's like to hang out with Mr Beast. I haven't finished all of it, but it's really interesting to see how Jimmy spends his time. —Nathan P.S. If you're planning to come to Craft + Commerce, let me know! |
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, 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...
Hey Reader, If I say something dumb, I'm probably still replaying it in my head 11 years later. Just me? It’s an exhausting feeling. You're not really solving anything, you're just reliving the moment over and over. And when you're building a business, there's always something new to add to the pile. After a while, it gets hard to tell which things actually need your attention and which ones you've just been dragging around. Start by writing everything down. When a worry stays in your head,...