In this Article
Danny Gregory wants you to pick up a pen.
It doesn’t matter if the last time you made art was in grade school — what matters is that universal urge to create. As the founder of Sketchbook Skool and bestselling author of 12 books, Danny helps budding artists around the world rediscover their creativity.
That’s what drew him to Kit to power the emails he sends to more than 20,000 subscribers. Here’s how he built up his paid newsletter offering from scratch, making more than $45,000 in less than two years.

The challenge: Navigating the fickle nature of online marketing
He knew people were interested in what he had to say, but it never felt like he could connect with his audience properly. Even with thousands of followers (he currently has 15.1k on Instagram), all it takes is a slight tweak in the algorithm, and all that effort disappears.
“I wanted to be independent,” said Danny. “I didn’t want to join another platform that felt corporate. I wanted my essays to feel like I was sending an email just to that person.”
Danny didn’t need a large number of followers to make a living. But he wasn’t sure what it would look like. “Something that’s always intrigued me is the concept of a thousand true fans,” says Danny. “It’s the idea from Kevin Kelly that a true fan who supports anything you make is worth more than your average follower. You can find people who love what you do enough to support you in doing it.”
The solution: Paid newsletters with Kit
That’s when the idea came for a paid newsletter. “I have been blogging, writing, and creating content all these years for free. I never even thought about selling it,” says Danny. “I still offer a free newsletter, but I switched to Kit in October 2021 with the intention to start a paid newsletter. Since then, I’ve made $45,000.”
It’s a constant balance for artists and creators today to know what to monetize without turning off their audience. “I have 20,000 people I write for on my free list and 600 on my paid list,” he says. “And I always wonder, if I write something good, who should I send it to? But I realized the people paying for my list really want to hear from me, and they’re the ones I want to give the most to.”
Both newsletters talk about creativity, but Studio Notebook takes a deep dive into the creative process and offers more detailed advice. “I talk much more in-depth about the process of working and creating in my paid newsletter, which is called Studio Notebook, which I send every Tuesday,” he says.
The strategy: Building a paid newsletter funnel
It’s one thing to build a free subscriber list. But instead of thinking about the paid newsletter like a newsletter, Danny thinks of it like a product. His funnel starts typically with social media — his Sketchbook Skool channel pulls in 211,000 subscribers looking to learn more about drawing, painting, and the artist’s process.
Danny’s funnel starts with an inspiring YouTube video like this one.
“My YouTube videos get discovered first,” says Danny. “I often take past essays and turn them into videos and let viewers know that it’s based on an essay and where to subscribe in Kit. Sometimes I make polished video versions of a given essay, and other times I read the emails aloud via livestream and take questions.”

Kit’s easy-to-use landing page builder makes gathering new email addresses a snap.
Danny adds the link to subscribe in the video’s caption and mentions it live. That landing page, built with Kit, drops subscribers into his free list, Danny’s Essays.

Once readers sign up for Danny’s Essays, he adds small reminders about his paid option.
From there, most people stay on the free list. But for those interested in going deeper, Danny includes a call-to-action at the bottom of every free email as a postscript and in the footer. Says Danny, “I also occasionally give access to a paid newsletter to my free list, so they can see what they’re missing.”
Finally, when they’re ready to sign up for Studio Notebook, subscribers see this landing page, powered by Kit Commerce:

The final step in the paid newsletter funnel.
Kit makes setting up your own paid newsletter easy. The hard part is figuring out what to say. Says Danny, “Start today. But take time before you launch your paid product and make sure it is not just more of your free product. People get tired of too much of the same, even if it’s great.”
Check out Danny’s paid newsletter
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