Welcome to “Creators, On Air!” which is Newsletter Circle Live Sessions with Substack Bestsellers!
Each week, I sit down with top Substack creators to uncover how they built successful paid newsletters.
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In this live session, we talked with , Director of Teaching and Learning at CUNY's Newmark Graduate School of Journalism.
He also runs the Substack newsletter , which has over 62,000 subscribers and more than 100 paid members.
Here’s a quick summary of what he shared about building his newsletter:
1. What it takes to grow a subscriber list to 60,000 people
Jeremy integrated sign-up forms directly into his content across multiple platforms, ensuring they were easy to access.
He focused on creating a strong first impression by offering a small gift or resource in his welcome email. This way, he strengthens subscriber onboarding and builds trust from day one—making it more likely that readers will stay engaged and eventually become paying members.
“Another way some smart creators are doing, in welcome emails, they are sharing some resources like an ebook or an article.
I share a list of tools like a one-pager as soon as people respond. As soon as people sign up, they get that.
Once they subscribe, they get this little thing in the welcome. And it just has a nice feeling to get something beyond just the generic content.”
Jeremy Caplan, Wonder Tools
He used lead magnets, such as exclusive reports and early access to certain content, to encourage sign-ups.
He mentioned the newsletter in every video and podcast appearance to increase visibility, reinforcing its value to his audience.
He tested different subject lines and sign-up page designs to optimize conversion rates. Engaged his existing audience by providing referral incentives, where subscribers could unlock bonuses by inviting friends.
2. Cross-promotions and partnerships
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