LET'S GET STRATEGIC
Monetizing Your Expertise on Substack
by Linda Pophal
Substack is a relatively new entrant to the social media mix, emerging on the scene in 2017. It’s a publishing platform that allows writers, journalists, podcasters, and creators of all kinds and levels of experience to share information with audiences of subscribers. There are free and paid options. Substack takes a 10% cut from paid subscribers; creators retain the rest, and some have been very successful at monetizing their content on this platform—very successful. For example, Lenny Rachitsky’s Lenny’s Newsletter (lennysnewsletter.com), focused on product management, generates more than $1 million annually.
Substack’s leaderboard offers a list of top creators across multiple categories (substack.com/leaderboard/bestseller/rising). Their success can be a big driver for other creators to dip their toes in the water of content monetization. But the ability to generate revenue by sharing content on Substack isn’t as straightforward as it may seem. Counterintuitively, Substack users and experts emphasize the value of free content in building a subscriber base. It’s also important to note that Substack has been seeing some deterioration as creators are leaving for new rival platforms (techbuzz.ai/articles/writers-are-fleeing-the-substack-tax). Best practices for monetizing content, though, are similar across these platforms. Topping the list, not surprisingly, is offering value that appeals to a specific target audience.
VALUE ATTRACTS SUBSCRIBERS
Carrie Loranger, a Substack strategist and former Fortune 500 marketing director, left her 18-year corporate career to build her own portfolio business, which, she says, “now runs seven income streams and counting.” Within a year, she built her 9-to-Thrive newsletter (thrivewithcarrie.substack.com) to almost 10,000 subscribers. As she gained expertise and experience on the platform, she reviewed more than 200 Substacks and now teaches other creators how to set up their own free and paid tiers.
“For my first 8 months, I assumed that locking more posts behind the paywall was how I’d get more paid subscribers,” Loranger says. But, she realized, “When I finally sat down with my own data, the opposite turned out to be true. The posts pulling in the most paid conversions were the free how-to guides I’d been considering as throwaway pieces.” Those insights prompted Loranger to add more free content, which increased her free-to-paid conversion rate tenfold. The most important takeaway for creators is this: Your free tier is not a loss leader. It’s your marketing engine.
FREE CONTENT BUILDS TRUST
“The shift from free to paid content is not really a content strategy question; it’s a trust question,” notes Jacquelyn LaMar Berney, president of the marketing and branding company VI (vimarketingandbranding.com). “Before someone pays for your expertise, they have to believe your perspective consistently helps them see something differently or make better decisions.” That belief forms when your content is able to solve a real problem for readers, for free, without a sales pitch attached. Free content, says Berney, needs to teach, educate, and establish credibility. It should make readers feel smart, offering insights that they can use immediately in their work or personal lives. Paid content, however, should solve execution problems, providing “deeper context, frameworks, access, analysis, or application,” Berney continues. “People are already overwhelmed with information. They’re looking for someone who can help them make sense of it.”
FROM FREE TIER TO PAYWALL
Oliver “Oli” Huggins, co-founder and CEO of ExpertEdge (expertedge.org) and VP of partnerships at Packt (packtpub.com), has found success through turning expertise into structured courses sold via platforms such as Coursera. His experiences have taught him an uncomfortable truth: “The lessons themselves have been commoditized, and anyone can get a competent version of the explanation in seconds.” Consequently, “charging for access to information alone disappoints.”
What does provide value, Huggins believes, isn’t just offering information—it’s offering proof. “Free tiers earn trust, and the paid tier sells the evidence,” he explains. In Huggins’ courses, that evidence is a graded assessment and a credential. On Substack, it might be deeper analysis, proprietary frameworks, or real-world implementation details from your own work. It’s the kind of specificity that can’t be found in a quick Google search.
Loranger also uses this principle to structure her newsletter. Free readers get her full how-to archive and a weekly creator economy briefing. Paid subscribers also get her Tuesday deep dive on a single monetization lever, the Creator Tool Vault (guides, master classes, and templates), and access to her private chat. The founding tier includes her Substack 360 course on building a portfolio business, as well as monthly coaching calls. The test Loranger uses is simple: “If a reader can finish your paid post and go do the thing that same afternoon, you’ve earned the money.”
THE PRICING QUESTION
Most creators pick a price and then try to figure out what content will justify that price. But this, Loranger says, is backward. “Before the number matters at all, you have to know what your ideal subscriber is willing to open their wallet for, and it’s hardly ever more posts,” she advises. “They’re buying a transformation.” The data backs this up. Elliot Sterling, a content strategist at Opus Virtual Offices (opusvirtualoffices.com), has tracked which monetization models work at scale. “The creators hitting $10,000 annually didn’t start with $50 per year of memberships,” he says. “They started at $8 and tested upward only after conversion rates stabilized.” That first cohort of paid subscribers, Sterling adds, “carries more weight than the price point itself because they become your marketing channel to the next cohort.”
Conversion rates typically hover between 2% and 5% of your free subscriber base, Sterling adds. So a 10,000-person free list might yield 200–500 paid members, depending on how well your content fits audience needs. Loranger’s own pricing came from trial and error. Early on, she says, “Churn was brutal. People signed up, grabbed whatever they came for, and left within a month.” So Loranger pushed her monthly rate to $97 and set the annual at $147, deliberately making the annual the obvious choice. “That cut the in-and-out traffic way down, and the people who committed for a year saw far better results simply because they stuck around long enough to do the work.” She advises building tiers to “attract the people who’ll stay with you long enough to get the outcome you promised.” Then let the numbers guide you: “Keep an eye on your churn, your free-to-paid conversion rate, and which posts are nudging people to upgrade. Just don’t lead with the price. Lead with the transformation your reader is after, then work back toward the number.”
THE POWER OF PATIENCE
Success doesn’t happen overnight, and that can be a tough lesson to learn. It’s also a lesson that, if left unlearned, can cause many content creators to give up too early, never reaching the success they might otherwise have achieved. “Expect 6 months before you can assess whether your model works,” Sterling states. “Patience with your data trumps impatience with your income during this window.” Meanwhile, resist the urge to lock more content away. Resist the urge to compromise on free-tier quality. Resist the temptation to turn your newsletter into a sales funnel. Instead, focus on what your free content does best: building an audience of people who trust your perspective. The paywall will follow, not because of the price, but because of the proof you’ve already provided for free. “The free tier is where you create belief. The paid tier is where you create transformation,” Berney says.
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LINDA POPHAL (