In last week’s post, one of my subscribers (and friend), the lovely Pamela Marshall, asked me a great question.
Despite having plenty of free subscribers on Substack, (15k+ at the time of writing) she’s struggling to convert them into paying subscribers and wants to know how she can improve her conversion rate without putting her writing behind a paywall.
A question I would love to know the answer to myself!
I currently have 102 paid subscribers, but 72 of those came through other offers I’ve run that included a Substack subscription. Only 30 have subscribed directly through Substack’s paid subscription system.
So while I’m delighted to have those subscribers, I’ve still got plenty to learn about convincing readers to upgrade to paid.
And Pamela’s question got me thinking.
Rather than pretend I have all the answers, I decided to do a little digging and look at five creators who’ve built successful paid Substack publications.
All five have earned their Substack bestseller badges, and one has even reached the orange 1,000-paid-subscriber milestone.
Here are the superstars in question!
Olivia Wickstrom — Petal + Hearth
Tracy Friedlander — The Second Act Strategist
Yana G.Y. — Unplugged (1000+ paid subs)
Lori Ballen — The Real Time Creator
Brent and Michael — Brent and Michael Are Going Places
Interestingly, every single one has taken a different approach.
Some switched on paid immediately, while others waited until they’d built an audience. Some offer resource libraries and workshops, while others focus on putting their writing behind a paywall.
It’s clear there isn’t one magic formula for building a successful paid Substack. The trick is finding an approach that suits you, your writing, your audience and the time you have available.
So let’s explore what we can learn from each of them, starting with…
1. What Kind of Substack Are You Building?
Before worrying about paid subscribers, think about what role you want Substack to play in your business or your life.
Yana G.Y., who writes Unplugged, talks about two different ways to use Substack:
Substack as the product. Your newsletter is the business, and people pay for your writing, expertise, resources, research or insights.
Substack as the audience builder. You publish predominantly free content to build relationships with readers who may eventually buy your books, courses, products or services.
Of course, you can combine the two, but having a rough idea of the direction you want to go in makes it easier to decide what to publish and what to charge for.
Where Are You in Your Journey?
Of course, your approach to paid subscriptions will also depend on where you are in your journey.
Are you:
sharing established expertise?
offering a unique perspective?
or inviting people to follow along as you learn something new?
Imagine two gardening newsletters.
The first is written by an experienced gardener who’s spent 20 years creating beautiful gardens, winning awards and teaching other people how to grow their own.
They could confidently launch with paid content from day one, using compelling headlines backed by years of experience and results. They might also offer detailed gardening guides, seasonal planting plans or workshops.
Lori Ballen is a great example of this approach.
She came to Substack with years of experience in online marketing, established audiences elsewhere and plenty of amazing results to share.
She writes about strategies she’s used to build successful businesses, shows readers what she’s achieved and confidently puts valuable content behind a paywall.
Now imagine a second gardening newsletter.
This one’s written by someone who’s just bought their first house with a garden and wants to document the experience of turning a patch of weeds into something beautiful.
The reason people might pay to follow this writer is completely different.
They’re enjoying the story, following the progress, cheering them on and perhaps even sharing advice about what to plant or how to tackle a particular problem.
It’s more of a shared journey.
Olivia Wickstrom’s Petal + Hearth is a good example of how this can evolve.
She started writing about her life in France, sharing personal stories and experiences while building an audience who enjoyed following her journey.
As her Substack grew, she began sharing more of what she was learning about writing, audience growth and building a creative business. With her background in freelance copywriting, that eventually developed into a more focused offering around helping other creators grow their publications.
She found an opportunity through doing, experimenting and paying attention to what readers responded to.
Then there’s a third kind of writer, whose essays, observations or storytelling are so enjoyable that people simply want more of them.
Brent and Michael Are Going Places is a fab example.
They write about their travels, experiences and useful travel tips, alternating between free and paid posts. Subscribers can also upgrade to hear the articles read by the authors themselves.
It’s a super simple model built around their writing and personalities.
Three very different approaches, all very successful at attracting paying subscribers.
2. What Are People Going to Pay For?
So let’s have a look at what people will actually pay for as I think this is where so many of us get stuck and overwhelmed.
We’d all love gazillions of paying subscribers, but worry that if we’re going to ask people for money, we need to offer an enormous amount of extra value.
(I always offer a bit too much which ironically has become my achilles heel).
So what should we offer?
Extra articles?
Private chats?
Exclusive videos?
Downloadable guides?
Workshops?
The possibilities are endless.
Let’s look at what some successful Substack creators are offering.
Olivia Wickstrom – Petal + Hearth
Olivia has something she calls her Member Vault, a growing library of digital resources worth over $500, with a new download added every Monday.
Her paid subscription also includes:
Two exclusive posts a month following her personal development journey, with guidance from coaches and experts.
Monthly live coaching sessions covering Substack, creative entrepreneurship and living abroad.
Monthly networking calls.
A private subscriber chat with regular accountability check-ins.
Founding members also receive an annual Substack audit, group coaching calls and a member spotlight.
Olivia says her paid subscriptions now generate over $60,000 a year.
One thing she does really well is adding a new resource to her Vault every Monday. It gives her something fresh to promote every week and shows readers that the library is becoming more valuable all the time.
I’ve done something similar with The 50+ Nomad’s Backpack, which contains my courses, guides and other resources, all available to paid subscribers.
There’s a ton of value in there, but simply filling a digital library doesn’t automatically persuade people to subscribe. You need to keep showing readers what’s inside and, more importantly, how those resources can help them.
But releasing a new resource every week is quite the commitment!
Tracy Friedlander – The Second Act Strategist
Tracy offers a different combination of benefits:
Monthly mini-workshops about writing, Substack growth and building a business around your expertise.
Invitations to special events and subscriber challenges.
Access to her full archive of paid articles and workshops.
She also experiments with special upgrade offers, giving readers a reason to subscribe at a particular time rather than leaving the invitation permanently open and hoping people eventually join.
Yana G.Y. – Unplugged
Yana has built a much more extensive business-focused offering, including:
Practical Substack growth programmes and challenges.
AI tools, custom GPTs and Claude skills to help subscribers create content and grow their publications.
Automation tools and workshops.
Monthly live Q&A sessions and individual strategy support.
Subscriber chats, community support and discounts on additional products.
Her subscription is positioned around helping readers grow and monetise their own Substacks, with tools and systems they can use to achieve that.
She also offers heavily discounted annual subscriptions through promotions, encouraging readers to commit for a full year.
Lori Ballen – The Real Time Creator
Lori takes a much more direct approach.
She puts the bulk of her writing behind a paywall, using the opening of each article to introduce the idea, share her experience and explain what readers will learn.
The detailed strategies, processes and practical information sit behind the paywall.
Yana has also talked about seeing faster paid subscriber growth as she increased the amount of content she paywalled, and I’ve noticed that many successful Substack writers reserve a substantial amount of their writing for paying readers.
It’s worth experimenting with, particularly if you’re sharing expertise, detailed tutorials or information people are willing to pay to access.
Brent and Michael – Brent and Michael Are Going Places
I also wanted to include an example that isn’t focused on teaching people how to grow a business or make money online.
As I mentioned earlier, Brent and Michael write about their travels, experiences and useful travel tips.
Their paid offering is refreshingly straightforward:
Weekly subscriber-only articles and travel tips.
Audio versions of their articles, read by the authors themselves.
Personal answers to subscriber questions via email or direct message.
They also offer a founding membership that includes a one-hour video call.
It’s a great example of how you can build a paid publication around your writing, experiences and personality, without creating an enormous library of courses, resources or workshops.
Start With What You Can Manage
Looking at all these offers, it’s easy to think you need to create a huge membership programme to attract paying subscribers.
But you don’t.
My advice is to start with whatever you can comfortably manage in the time you have available.
You might decide to:
Publish three free articles and one paid article every month.
Record audio versions of your posts and make them exclusive to paid subscribers.
Add one new downloadable resource to a member library every month.
Publish one exclusive video or pre-recorded workshop.
Host a monthly live session if that’s something you enjoy.
You could start by publishing mostly free content, then gradually increase the amount you put behind a paywall as your audience grows and you become more confident about what readers value.
Perhaps you begin with three free posts and one paid, then eventually reverse that balance.
Or you might stick with one excellent paid article a month and keep everything else free.
There’s no requirement to offer everything, and no reason to promise more than you can deliver.
Choose something your readers will value, make it clear what they’re getting and build from there.
3. When Should You Switch On Paid Subscriptions?
This is a question I’ve seen come up a lot in Notes and posts on Substack, so here’s what the creators I’ve been following recommend.
Yana G.Y. recommends switching on paid immediately, provided you have a clear offer and know who you’re writing for. She did exactly that and attracted three annual subscribers straight away.
Tracy Friedlander switched on paid at around 350 free subscribers and says she wishes she’d done it sooner.
Olivia Wickstrom recommends waiting until you’ve built an audience of around 500 free subscribers.
Lori Ballen switched on paid from day one and took a much more aggressive approach to putting her writing behind a paywall.
So who’s right?
Well, they all are. There’s no right or wrong here, and a lot depends on you and your confidence levels.
Whether you’ve got years of experience, a clear audience and know exactly what you want to write about, or you’re starting from scratch and finding your feet as you go, there’s no reason you can’t switch on paid subscriptions from day one.
You don’t have to create an enormous membership offering or start hiding your articles behind a paywall. You can simply invite readers to support your writing as you grow.
And if your goal is to turn Substack into a side hustle, an income stream or a business, then you need to turn the income lever on asap.
It takes away the whole question of when to start charging, gives your writing a potential income stream from the beginning and gives you something to work towards.
Remember, there’s a difference between enabling paid subscriptions and putting your writing behind a paywall.
Keep it simple and start with Substacks minimum subscription price, at $5 a month, and add a message to the bottom of your articles, something like:
Thanks so much for reading! If you enjoy my articles and would like to support my writing, I’d love you to become a paid subscriber.
And that’s it. Keep writing, experimenting and building your audience, knowing that anyone who enjoys your work has the option to support you along the way.
4. How To Convert Readers From Free to Paid?
There are 2 main routes.
Become so ridiculously successful and build such a massive audience that paid subs grow purely as a game of numbers. This accounts for the huge accounts you see who have no promotions and don’t seem to paywall anything.
Become very deliberate about promoting your paid offerings.
The creators I’m highlighting here are all in camp no 2.
They don’t simply switch on paid subscriptions and hope people notice.
They invite readers to upgrade, explain the benefits and create opportunities for people to say yes.
Yana: Make the Most of the First 30 Days
Yana is particularly focused on the first few weeks after someone subscribes.
She reports that 71% of her paying subscribers upgraded within 30 days of joining her free list, and more than 20% upgraded on their first day.
She’s put a lot of effort into making that happen.
Her welcome email introduces the publication, explains what paying members receive and encourages readers to upgrade straight away.
She also has an automated onboarding sequence set up through Kit, along with an About page and pinned post that direct readers towards her paid offering.
Rather than leaving the decision entirely to chance, she’s built a system that consistently introduces new readers to the benefits of becoming paying subscribers.
Olivia: Show People What They’re Missing
Olivia takes a slightly softer approach and includes upgrade invitations in free articles, uses email headers to remind readers about paid benefits and occasionally publishes material for free that would normally sit behind her paywall.
One of her most successful free posts attracted more than a thousand new subscribers, who could then discover her paid offering over time.
And that’s something to bear in mind and test.
Sometimes giving away your best work is the smartest way to attract paying readers.
It demonstrates the quality of what you create and gives people confidence about what they might receive if they upgrade.
Tracy: Give People a Reason to Subscribe Now
Tracy creates specific reasons to subscribe.
When she was working towards her first 100 paying subscribers, she offered opportunities such as a Notes-writing course for founding members.
Rather than relying entirely on an ongoing subscription offer, she gave people a particular experience they could join.
She says it took seven months after switching on paid to reach 100 paying subscribers.
Lori: Let Readers Try Before They Buy
Lori puts most of her articles behind a paywall but offers readers a seven-day free trial.
That means someone can sign up and spend a week exploring her back catalogue of articles, seeing exactly what they’re getting before deciding whether to continue with a paid subscription.
It’s a great approach if you’ve already built up a substantial library of valuable content, as readers can experience the benefits of subscribing without having to commit immediately.
Brent and Michael: A Softer Approach to Paid Content
Brent and Michael take a much softer approach.
As I mentioned earlier, they alternate between free and paid articles, so readers get a regular taste of their writing while paying subscribers receive the additional content.
They also offer a discount for subscribing annually, and readers who want to listen to the articles read by the authors themselves need to upgrade.
I really like this approach because there’s no hard sell. Readers can continue enjoying the free articles, but there are plenty of opportunities to upgrade if they want more.
What Can We Do?
There’s no guarantee that any of these approaches will work for every publication, but there are some simple things we can all do.
Make the paid offering clear on your about page. Explain it in your welcome email. Mention it naturally in relevant articles. Show readers what’s available, and periodically give them a specific reason to upgrade.
And perhaps most importantly, don’t assume people already know what your paid subscription includes.
They probably don’t.
5. From Your First 10 Paid Subscribers to 100
So we’ve looked at what kind of Substack you’re building, what you could offer paying subscribers, when to switch on paid and how to encourage readers to upgrade.
Now let’s put it all together and look at some practical strategies for getting from zero to 100 paying subscribers.
Your First 10: Prove People Will Pay
At this stage, I’d keep things simple.
Make sure your paid offer is clear, publish something worthwhile and invite people to support your work.
You could even start with one exclusive paid article a month.
Your first few paying subscribers provide useful evidence that someone values what you’re creating enough to pay for it.
And don’t underestimate the people who subscribe simply because they want to support you.
Not every paid subscriber is looking for an enormous library of exclusive content. Some people enjoy your writing, believe in what you’re doing and want to help you continue.
From 10 to 50: Experiment With Conversion
Once people have started paying, you can begin learning which parts of your offering attract them.
Are they upgrading after reading a particular article?
Does a practical resource encourage more subscriptions than a personal essay?
Are people responding to an invitation in your welcome email, or upgrading after following you for several months?
This is where I’d start testing different approaches, one at a time.
You might experiment with offering a particularly valuable resource, publishing a free preview of a paid article or introducing a limited-time invitation around a new series.
The aim is to understand what readers respond to, rather than continually adding more benefits in the hope that something eventually works.
From 50 to 100: Repeat What Works and Keep the Subscribers You Have
As your paid audience grows, you can begin developing a more consistent system.
Yana credits an automated welcome sequence that she delivers with Kit with attracting a substantial number of her paying subscribers. She also places considerable emphasis on retaining existing members.
And that makes sense.
If you’re gaining ten paying subscribers a month but losing eight, you’re going to have a long journey to 100.
Olivia’s growing resource library is one way of providing continuing value. Tracy’s regular workshops are another. A writer who publishes an excellent exclusive essay every fortnight might achieve the same goal with considerably less complexity.
The important thing is to keep the promise you made when people subscribed.
I also think it’s worth remembering that growth rarely happens in a perfectly straight line.
Yana started with no external audience and says it took her 23 months to reach 1,000 paying subscribers. Olivia says she didn’t experience what she considered significant results until around month nine, after publishing more than 200 long-form posts.
Those are useful reminders when we’re tempted to compare our early progress with someone else’s latest screenshot.
How to Convert Free Subscribers Without a Paywall
So let’s come back to Pamela’s question, which inspired this article in the first place.
How do you convince free subscribers to upgrade to paid if you don’t want to put any of your writing behind a paywall?
I think the answer is to give people a reason to support you, even when they can continue reading everything for free.
And there are a few ways to approach this.
Make it personal. Tell readers why you’re writing your publication, what you hope to achieve and how their support helps you continue.
Ask regularly. Include a simple invitation to upgrade at the bottom of your articles, in your welcome email and on your about page. Don’t assume people will find the paid option themselves.
Offer a little something extra. Perhaps a downloadable guide, a collection of your best articles in PDF format, an audio version of your writing or early access to something you’re creating. It doesn’t have to be an enormous membership offering.
Give people a reason to upgrade now. Experiment with a special annual subscription offer, a bonus download or a limited-time promotion.
Remind people what they’re supporting. If your writing helps, entertains or inspires people, don’t be afraid to explain that paid subscriptions help you keep producing it.
And remember, some people will happily pay simply because they enjoy your work and want to support you. They don’t necessarily need more content.
So if you don’t want to use a paywall, don’t. Keep publishing your best work for free, make your paid invitation clear and experiment with different ways of encouraging readers to support you.
You might be surprised how many people are willing to pay for something they could read for free, simply because they value it.
Your First 100 Paid Subscribers
After reading all these creators’ experiences, it’s clear that there isn’t one perfect route to building a successful paid Substack.
And that’s the good news!
You don’t need to copy somebody else’s entire business model to learn from their success.
You can borrow Olivia’s approach to demonstrating the value of a resource library, Tracy’s idea of giving people a timely reason to upgrade, Yana’s attention to welcome emails, Lori’s use of free trials, or Brent and Michael’s softer approach of alternating free and paid content.
Then experiment with what works for your own audience.
For me, that means continuing to develop my writing, getting clearer about the value of The Backpack and making it easier for readers to understand what they’re supporting when they become paid members.
I’m still on my way to that first 100.
And when I get there, I’ll have a much better understanding of which strategies made the difference.
In the meantime, if you’re building your own paid Substack, I’d love to know what you’re trying, what’s working and what you’re finding difficult.
I suspect there’s plenty we can learn from the people who are still figuring it out, as well as the ones who’ve already collected their bestseller badges. 😎
This was really interesting Jo. Thanks for all your research and time putting this together. And perfect timing for me. I have recently turned on "paid" and am still figuring out what it looks like. So I pleased by your conclusion that there is not one path to success. Best wishes in yours! Susan