One of the most valuable things we do at Write • Build • Scale is coach creators through the exact decisions that feel overwhelming when you’re doing them for the first time. Launching a paid Substack tier is one of those moments.
In this session, we worked through the paid launch strategy of Alicia Teltz — a former LinkedIn employee turned entrepreneur who has built a loyal audience around LinkedIn growth strategy.
She came to us with the same questions we hear from creators constantly:
When should I launch?
What should I charge?
What do I actually put behind the paywall?
We walked through all of it live. Below is everything we covered and what you can take away whether you’re building toward your first paid subscriber or planning your next promotion.
Your Paid Tier Is Not a Newsletter
The single biggest reframe in this conversation — and one that comes up in our coaching programs over and over — is this: stop thinking of your paid Substack as a paid newsletter.
A paid newsletter implies more of the same content, just with a paywall on it. That is not a compelling reason for anyone to upgrade.
The subscription economy has trained people to be ruthless about what they pay for, and “more emails” doesn’t cut it.
What does work is treating your paid tier like a membership product. That means distinct member perks. Different content formats. Exclusive experiences. A sense that paid subscribers are in a different category, not just free subscribers who handed over a credit card.
In Alicia’s case, she was coming from a Circle community that had gotten too time-intensive: weekly calls, post reviews, constant availability. She wanted to keep serving her audience without burning out. The solution wasn’t to rebuild the same thing on Substack — it was to identify what her audience actually valued and design something more sustainable around that.
For her, that looked like: in-depth bi-monthly posts with templates, a monthly live group workshop, and a premium content library.
Simpler, more scalable, and still genuinely valuable. That’s the framework worth thinking about for your own tier.
When Is the Right Time to Launch?
This is the question we get asked most often, and the answer usually surprises people: the audience size matters far less than you think.
If you have a few hundred engaged subscribers who know you, trust you, and have seen you deliver value consistently — you are ready.
You don’t need thousands of followers before you can start earning from your Substack.
What you need is an audience that knows exactly what they’re getting, and a paid offer that reflects that clearly.
In Alicia’s case, she had 1,300 subscribers on Substack and an additional 6,000 email addresses from a previous list she’d never fully activated.
More importantly, she already had proof of demand: people had paid her for a community before. That changes the calculation significantly.
There’s also a timing element worth noting for anyone launching soon: summer tends to slow things down. If you have any flexibility in your timeline, launching before July gives you a better chance at a strong first campaign.
One practical way to warm things up before you go live is to leverage any existing audience you have outside Substack. An email to your list with a link to recent Substack posts — framed as a simple “here’s what I’ve been publishing” — can meaningfully grow your subscriber count before you flip the paid switch.
If you want a full toolkit for this pre-launch phase, our Free-to-Paid Playbook covers 100+ conversion strategies organized by subscriber stage — so you know exactly which moves to make depending on where you are right now.
Build a Premium Content Library Before You Launch
Before your paid tier goes live, you want something waiting for people on the other side of the paywall so it’s not just an empty archive with a big promise.
This taps into what behavioral economists call instant gratification bias — and it’s one of the most powerful conversion tools available to Substack creators.
Instead of “join now and get premium content in the future,” the message becomes “join now and unlock this library of workshops, templates, and guides immediately.”
4-5 high-quality resources is enough to start. In Alicia’s case, she already had templates and workshop recordings from her previous community. Those don’t need to be rebuilt, they just need to be organized and uploaded to Substack.
The premium content library itself should live as a pinned, publicly visible page on your publication.
Free subscribers can see everything listed there, but when they click on any resource, they hit a paywall. This means the library is simultaneously a thank-you for existing paid members (everything is easy to find in one place) and a powerful marketing asset for free subscribers sitting on the fence.
One tactic worth layering in: if you have upcoming workshops or resources in production, list them on this page as “coming soon.” You’re not manufacturing hype out of nothing — you’re being transparent about what’s in the pipeline, and it creates genuine anticipation.
The Free Preview Strategy That Sells Without Selling
For workshops in particular, there’s a feature inside Substack that most creators underuse: the free preview.
When you upload a workshop as a paid post, you can set the first 10 to 15 minutes to be freely accessible to every subscriber. The rest sits behind the paywall. What this does is let your work do the selling for you.
Free subscribers get to see the quality, the format, your personality, how you show up. They get enough to feel the value before they’re asked to pay for it. And for people who are hesitant about committing, that preview often tips the decision.
This is especially useful for creators who don’t love hard selling. You’re not writing a pitch — you’re just publishing content and letting it speak. The upgrade button is there. The people who want the rest will find it.
This same logic extends to the text that accompanies each workshop post. Letting free subscribers read the full written summary while the video remains locked is another version of the same principle: give them enough to want more, then make upgrading simple.
How to Think About Pricing
Let’s be honest about something that doesn’t get said enough: pricing low doesn’t make it easier to sell.
The belief that a cheap offer will convert more easily is one of the most persistent myths in the creator economy.
In reality, the psychological barrier of pulling out a credit card exists regardless of the price point.
The question people are really asking isn’t “is this affordable?” — it’s “is this worth it?”
Pricing too low creates a different problem: it signals low value, leaves you no margin for promotions, and means that even a healthy subscriber count doesn’t translate to meaningful revenue.
The pricing structure that has worked well for us — and that we recommend to creators who want to build a sustainable paid tier — is a higher monthly price paired with a deeply discounted annual plan.
In practice, that looks something like $20/month or $80/year, where the annual plan works out to less than four months of the monthly rate.
The strategic goal here is to make the annual plan the obvious choice.
When more than 90% of your paid subscribers are on annual plans, your revenue is more predictable, churn is dramatically lower, and the relationship you build with each subscriber over a full year means they’re far more likely to renew — or to explore other ways of working with you.
Discounts, when you run them, should almost always be on the annual plan only. You’re not trying to lower the price of access — you’re giving people a reason to commit for the long term.
Deciding exactly how to convert free subscribers into paid ones — based on how long they’ve been following you, how engaged they are, and where they are in the decision process — is where most creators get stuck.
Our Free-to-Paid Playbook was built specifically for this: 100+ strategies organized by difficulty and subscriber stage, so you can find what fits your situation and test it this week.
The Founding Member Tier
Substack’s founding member option often gets ignored or misunderstood. Think of it as a third tier, almost like a VIP tier that sits above your monthly and annual plans.
For creators who offer consulting, coaching, or done-with-you services, this is a natural home for a high-touch package. In our publication, the founding member tier includes private coaching calls and is priced accordingly.
But even if you don’t currently have something to put in it, it’s worth setting up simply for the anchoring effect. When someone is evaluating your subscription options and they see a higher-priced founding member tier alongside monthly and annual plans, the annual plan starts to look like a very reasonable middle ground. That perception shift can meaningfully improve your conversion on the annual plan without you changing anything else.
Skip the Pledge Feature
If you’ve been poking around in your Substack settings, you may have stumbled across the pledging option. Our recommendation is simple: don’t use it.
Pledging is designed to let subscribers pre-commit to paying before your paid tier is officially live. But it creates confusion for anyone who lands on your page — it can appear as though your publication already requires payment, which may stop potential free subscribers from signing up at all.
If you want to start collecting revenue before your full paid launch, just turn on the paid tier with an honest note on the perks page explaining that premium content is coming soon. Your early supporters will subscribe anyway. And you won’t accidentally create friction for the people you’re trying to grow your free list with.
Running Your Launch Promotion
When your paid tier goes live, treat it like a launch instead of just a soft announcement.
A 4-day promotional window works well for Substack. It’s long enough for your whole audience to see it, short enough that urgency stays real. Over those four days, you’d typically send four or five emails, structured roughly like this:
Day 1:
The announcement. This is a public post — pin it to your homepage. It introduces the paid tier, highlights the benefits, features some of what’s already in the library, and explains the launch offer. Lead with outcomes. What will paid subscribers learn, do, or become?
Here’s an example of a promotion we’ve run at Write • Build • Scale:
Days 2 and 3:
Dedicated emails sent to your list but not published publicly as posts. These can mix social proof, a closer look at specific resources behind the paywall, and reminders of the discount or bonus that’s expiring.
Day 4:
Urgency. This is where most of your conversions will happen. A deadline is a real service to people who’ve been thinking about it — it gives them a reason to decide. Send a final email (sometimes two) emphasizing that the discount closes today.
For the launch offer itself, a 30–50% discount on the annual plan works well. Alternatively, if you want to stay at full price, a high-value exclusive bonus available only during the launch window can accomplish the same thing.
After the launch, a promotional cadence of once every two to three months is sustainable and effective. You don’t need a different offer every time — but it helps to have a hook, whether that’s a platform milestone, a seasonal tie-in, or a new piece of content you’re releasing. The goal is to give people who weren’t ready the first time a genuine reason to reconsider.
The Biggest Mistake Creators Make
We asked each other this at the end of the session: what’s the #1 one thing that holds paid Substack tiers back?
The answer, in both cases, came back to visibility and confidence.
On the visibility side: if it’s not easy and obvious for someone to upgrade, they won’t. A buried subscribe button in a post from six months ago is not a paid tier strategy. You want a premium content library, a dedicated membership page, a clear upgrade prompt in your about page, and upgrade links woven naturally throughout your content.
On the confidence side: if you don’t believe your paid tier is genuinely worth paying for, you’ll price it too low, promote it too timidly, and apologize for asking. The reframe that matters here is this — if you’ve built something that delivers real value to your subscribers, asking them to pay for it is not a favor you’re asking of them. It’s the mechanism that lets you keep delivering that value. It’s a good deal for everyone involved.
This Is What Coaching With Us Looks Like
The session you just read through is a real example of what we do inside our private coaching programs at Write • Build • Scale.
We help creators, consultants, coaches, and experts cut through the confusion around Substack, and skip the trial and error that wastes months of momentum.
If you’re building a Substack publication and want to do it right from the start, or if you’ve already launched and you’re not seeing the growth you expected, this is exactly the kind of work we do together.
→ Find out more about working with us privately here.
Not ready for private coaching yet? Start with our Free-to-Paid Playbook — 100+ proven strategies for turning your free subscribers into paying members, organized so you can find the right approach for where you are right now.
Thank you Jeff Herring, Raquel Devillé, ✨️ Highly Sensitive Woman ✨️, Head Global Career Studio, Stéphane Dosdoghrouyan, and many others for tuning into my live video with Jari Roomer and Alicia Teltz!
