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.
How to know when to double down
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Hey Reader, Last week I talked about my wastebasket for ideas. The idea bin helps you manage the constant flow of new ideas without letting them derail your focus. But eventually, an idea sticks around long enough that you decide it's worth exploring. So what do you do next? Here's the framework I like to use: test, bet, systematize. 1. TestWhen you pull an idea out of the bin, you're not committing to it long term. You're designing an experiment to see if it's worth pursuing. A good test has clear parameters. You decide upfront what you're going to do, for how long, and what you're measuring. Anne-Laure Le Cunff talks about the tiny experiment approach—running small, focused tests to learn by doing instead of planning. Maybe you commit to sending 20 cold outreach emails every day for 30 days. Maybe you run a single webinar to see if anyone shows up. The important thing is having a structure: this is what I'm testing, this is how long I'll test it, here's what I'm tracking. The most important part of testing is defining what success looks like upfront. You need to know how you'll evaluate whether the test worked. Otherwise, you'll just keep testing forever, or you'll abandon something that was actually working because you didn't know what you were looking for. It doesn't have to be complicated. One sentence works. "If I get 10 qualified leads from this webinar, it's worth running another one." "If 5 of the 20 people I email each day respond positively, I'll keep going." The criteria gives you permission to either double down or move on. 2. BetWhen a test works, you move it into the bet phase. This is where you put real resources behind it. We ran one webinar in the early days of Kit and got 100 new accounts from it. That was enough to say, okay, let's actually staff this. Let's run more webinars. Let's figure out how to make this repeatable. A bet is different from a test because you're not just trying it once to see what happens. You're saying, "This worked enough that I'm going to build a team around it, refine the process, and scale it." But bets are inherently unstable. They're not self-sustaining yet. You can't just set it and forget it. You're constantly tweaking, refining, figuring out what works and what doesn't. For webinars, that meant: can we train someone else to teach them? What happens when we run them weekly instead of monthly? How do we improve the conversion rate? 3. SystematizeEventually, a bet that keeps working becomes something you systematize. This is where you move from, "I can do this and get results" to, "Anyone on the team can follow this process and get similar results." You document it. You build the infrastructure around it. You make it repeatable without requiring you to be involved in every instance. This doesn't mean the work is done. Even systems need maintenance and iteration. But it does mean you've moved from something that requires constant attention to something that can run without you needing to manage every detail. From that point, you could look at turning this into a flywheel. Not every idea from the bin will make it through all three phases. Most won't even make it past the test. But that's the point. The test, bet, systematize framework helps you figure out which ideas are worth your time and which ones should stay in the wastebasket. PODCASTHow Creators Can Use AI Voice Agents To Grow Their Business In 2026Today, we’re doing something we’ve never done on the podcast before: a live, real-time build of a voice AI agent. Jay Singh, founder of Casper Studios, is back on the show to explore the practical side of AI implementation for creators. We break down the tools we use, how we craft prompts, and why voice is such a powerful lever for content creation. Then Jay walks through exactly how to build a voice agent from scratch. You'll see how you can use voice to speed up your workflows and collect better feedback using tools like Whisper Flow and ElevenLabs. KIT FEATUREEmbed Pinterest Pins in your emailsKit now has a Pinterest app that lets you embed Pins directly into your emails. You can add Pins as full content blocks or standalone images. If you're creating visual content on Pinterest—whether that's recipes, tutorials, design inspiration, or anything else—this makes it easy to repurpose that work in your newsletter. It's a simple way to connect two platforms you're already using and get more out of the content you've already created. Check out the Pinterest app on Kit » EVENT - NOVEMBER 13Austin Creator Event with Ryan HolidayI want to invite you to a very special event happening next week. My good friend Ryan Holiday is joining me for a live recording of The Nathan Barry Show on November 13 at The Sunset Room in Austin. Ryan and I have been building our creator businesses alongside each other for over a decade, and in this conversation, we're digging into the side of his work he doesn't usually talk about—how he actually built his business, the systems and flywheels behind his bestselling books, and the decisions that let him keep creating at this level year after year. Before the live show, we're bringing in Ultraspeaking for a three-hour workshop starting at 2pm. If you've never experienced Ultraspeaking, this is hands-on practice with live feedback from their team of coaches. You'll work in small groups, play speaking games, and walk out tangibly better at communicating. Here's the full schedule:
⭐ The first 100 people to arrive will get a free copy of Ryan's newest book, Right Thing, Right Now. After the show, stick around for the happy hour. Connect with other Austin creators, trade ideas, and build relationships with people doing similar work. If you're anywhere near Austin, you don't want to miss this. 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.
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