The $459 Post She Almost Paywalled
The Story
Olivia originally planned to put her full Pinterest strategy behind the paywall. She didn’t. Her own account of why and what happened:
“I almost put my top performing Substack post behind a paywall… I’m SO glad I didn’t. I originally mentioned my Pinterest strategy in a note about making my first $1K on the platform, and the comments blew up. Nearly 100 people wanted the full breakdown. So I wrote it. Typically, I’d make a post like this locked since in-depth tutorials are part of what my subscribers pay for. But the demand felt different this time, so I published it for everyone” (Source 1).
The numbers from the free version: “The result: 162 new subscribers and an estimated $459 in revenue from people who converted after reading it. That’s more than most of my paywalled tutorials bring in directly” (Source 1).
Her framing of what changed in her thinking: “I think there’s something to be said about giving away your best work strategically. Not all of it, not constantly, but occasionally putting your most useful stuff in front of the widest audience and trusting that the right people will want more” (Source 1).
She made the same call on the Notes strategy deep-dive: “Usually, posts like this are reserved for paid subscribers (shameless plug: if you want more tactical deep dives like this, [become a paid subscriber] 💕). But so many of you asked for this that I’m making it free. Consider it my gift” (Source 2).
She turned the discovery into an annual experiment: “I’m going to try this once a month in 2026. One post I’d normally paywall, made free. I want to see how it affects growth versus revenue over the year. If you’re running a paid Substack, it might be worth experimenting with the same thing” (Source 1).
The general version of the principle, written separately: “I’d understand that free content is what drives paid subscribers. Don’t put all your value behind the paywall. Your free posts need to be good enough that people want more. Give generously in public, and the right readers will upgrade when they’re ready” (Source 3).
Lesson for Creators
The instinct for paid-newsletter writers is to gate the best material because that’s what “paid is for.” Olivia’s $459/162-subscribers data point is one of the cleanest counterexamples in circulation: the post she almost gated outperformed the posts she actually gated. The mechanism is straightforward — paywalled tutorials only earn from people who are already paid subscribers; free tutorials earn from everyone the post can reach, with paid conversion as the upside layer. The deeper point is that “paid” isn’t a vault, it’s a relationship. Your best free work is the proof-of-craft that makes paid feel obvious. Hiding it inverts the funnel. Olivia’s once-a-month experiment is the right experimental design: not “give everything away,” but “test which specific posts perform better in front of the widest audience than behind a wall.”
Related
- Free Stuff Better Than Their Paid Stuff — Nathan May: same “give away the sauce” principle in B2B services
- Two Years of Free Before the Paid Switch — Tom Orbach: trust built free first, paid converted at scale later
- 100,000 Pinterest Visitors to a Substack — Olivia Wickstrom: this is the actual post she almost paywalled
- Patreon Quit, Substack Paid Won — Jesse J. Anderson: paid conversion working better when it’s casually positioned, not forced
- Why Paid Newsletters Are Really, Really Hard — Nathan May: the structural reasons most paid Substack experiments don’t work