How to Sell a Digital Product on Substack Without Coming Across as "Salesy"
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"5-Day Digital Product Sales Launch Training for Writers" — This method ensures your product sells by properly prepping your newsletter audience
"Six Figure Digital Product Brainstorming Template" — This template helps you mine your existing newsletter content for product ideas your audience will actually pay for
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I still remember the first time I tried to sell something to my subscribers.
My finger hovered over the "publish" button for what felt like hours. The email was written. The product was ready. But I couldn't shake this nagging voice in my head:
"They're going to think you've turned into one of those internet marketers."
"People subscribed for your content, not to be sold to."
"What if everyone unsubscribes?"
If you're like most writers I talk to, the idea of selling anything to your audience feels... uncomfortable. Maybe even a little dirty. You've built a relationship based on value and trust, and the thought of "monetizing" that relationship makes you cringe.
I get it. I really do.
But what if I told you that this fear—this resistance to selling—isn't just holding you back financially? It's actually preventing you from serving your audience at the highest level.
Over the past eight months, I've generated over $50,000 selling simple digital products to my audience. And the most surprising part? Not a single reader has ever complained about being "sold to." In fact, I regularly receive thank-you emails from subscribers grateful that I offered them a solution to their problems.
Today, I want to share how you can sell digital products on Substack without feeling salesy, without compromising your integrity, and without alienating your audience.
Most writers stay broke because they’ve never learned this one skill. The whole “starving artist” thing. If writers simply knew how to better serve their audience in the form of a digital product, we’d have to retire the “starving artist” phrase.
Because the truth is, learning to sell effectively might be the most valuable skill you can develop as a writer.
Selling Is Actually Serving
Here's the mental shift that changed everything for me: selling isn't taking from your audience—it's serving them at a deeper level.
Think about it. You started your newsletter because you have valuable insights, expertise, or perspectives to share. You spend hours crafting posts that help your readers in some way. Your free content solves problems, provides inspiration, or offers guidance.
Your digital products simply do this more comprehensively.
When someone reads your newsletter and thinks, "This is helpful, but I wish they would go deeper on X," or "I wonder how I could implement this more effectively"—that's a need you could be filling with a product.
By not creating and offering that solution, you're actually withholding value from the people who want it most.
I learned this lesson through a reply from a reader. After I finally gathered the courage to release my first paid product, he wrote:
"I've been waiting for something like this for months. I kept reading your newsletter hoping you'd offer a more structured way to implement your ideas. Thank you for finally creating this!"
That email was a wake-up call. This reader had been waiting for me to offer more help, and I had been too afraid of seeming "salesy" to provide it.
Here's the uncomfortable truth: if your audience wants more help than your free content provides (and trust me, some of them do), and you don't offer that help through a product or service—they'll go elsewhere to get it.
They'll buy someone else's course, book, or templates. They'll hire someone else as a coach or consultant. They'll find solutions from creators who aren't afraid to offer them.
It might as well be you providing that solution. After all, they're already learning from you. They already trust your approach and perspective. You're actually the ideal person to help them go deeper.
Selling isn't something you do to your audience. It's something you do for them.
But What About Unsubscribes?
Let's address the elephant in the room: the fear of people unsubscribing when you start selling.
I remember obsessively checking my subscriber count after sending my first product launch email. And yes, I lost a few subscribers that day—seven, to be exact. But here's what also happened: I made 21 sales at $47 each, generating $987 in revenue.
Those seven unsubscribes? They actually did me a favor.
Here's the reality: if someone unsubscribes because you mentioned a digital product that's designed to help them, they were likely never going to buy anything from you anyway—not your product, not a paid subscription, nothing.
They were looking for perpetually free content, and that's perfectly fine! But building a sustainable newsletter requires some portion of your audience to move beyond free consumption.
Think of unsubscribes as a natural filtering process. They're not rejections; they're clarifications. Your audience is self-selecting into those who just want free content (which you'll continue providing) and those who are open to deeper, paid solutions.
The subscribers who stay—even if they don't purchase immediately—are signaling something important: they're okay with you occasionally selling something. That's the audience you want to nurture.
And remember: for every person who unsubscribes, new subscribers are joining who will only know you as someone who provides both free and paid value. They'll have no expectation of an exclusively free relationship.
After eight months of selling products through my newsletter, I've learned that the unsubscribe anxiety dramatically overestimates the actual impact. It's a fear that keeps too many talented writers from building sustainable businesses around their work.
Don't let that be you.
Nobody Is Paying as Much Attention as You Think
Here's a liberating truth that took me way too long to discover: people are thinking about you and your "salesiness" far less than you imagine.
Psychologists call this the "spotlight effect"—the tendency to dramatically overestimate how much attention others are paying to our actions and appearance. This effect goes into overdrive when we're selling.
We agonize over how our audience will perceive us:
"Will they think I've sold out?"
"Are they judging me for monetizing my knowledge?"
"Do they feel like I'm becoming too commercial?"
Meanwhile, your average reader spends about 30-90 seconds scanning your email before moving on with their day. They're dealing with work stress, family obligations, and the other 37 unread emails in their inbox.
Most readers barely notice when you're selling, let alone develop elaborate judgments about your character based on it.
I once accidentally sent the same promotional email twice in one week (scheduling error—oops). Know how many people called me out for the duplicate sales pitch? Zero. Not a single person mentioned it.
That was a wake-up call about how much attention people were actually paying.
When I analyzed my open and click rates, I discovered something else surprising: my sales emails often had HIGHER engagement than my regular content. People were curious about what I was offering. Some even looked forward to my launches because they specifically wanted more comprehensive solutions.
The reality is, most of your audience is totally comfortable with the occasional sales message. They understand that creating valuable content requires financial sustainability. Many are genuinely happy to see you offering ways to work with you more deeply.
Once you internalize this, selling becomes so much easier. You can stop overthinking every word, stop apologizing for offering value, and start focusing on actually helping those who want more from you.
Stop "Selling," Start Extending
One of the most powerful mindset shifts I've made is to stop thinking about "selling" entirely. Instead, I view my digital products as natural extensions of my free content.
Your newsletter already helps people think differently, solve problems, or improve some aspect of their lives. Your digital product simply takes that help one step further—it's more comprehensive, more actionable, or more personalized than what you can provide for free.
This small reframing makes promotion feel entirely different. You're not interrupting your valuable content with sales pitches; you're creating a coherent ecosystem of value at different levels.
Here's what this looks like in practice:
When I write about a topic in my newsletter, I'll naturally mention my related product as an extension: "I cover the step-by-step process for this in my Substack Growth Guide, but here are three quick tips you can implement today..."
Notice the pattern—I'm still giving value in the free content, while casually mentioning the paid option for those who want to go deeper.
This approach works because it's genuine. Your digital product truly IS a natural extension of your content. It's not some random offer disconnected from what your readers already know you for.
The language you use matters too. Rather than "selling" or "promoting," I think about:
Offering additional help
Providing a more structured approach
Sharing a comprehensive resource
Creating a shortcut to implementation
When you view your product this way, you can present it with authentic enthusiasm rather than apologetic hesitation. You're genuinely excited to provide this deeper level of help to those who want it.
Remember: your free content and paid products aren't separate entities with different purposes. They're points on a continuum of how you help your audience—from casual readers to dedicated implementers who want more guidance.
“But Help! Nobody Is Buying My Product”"
"I tried selling a digital product and hardly anyone bought it. What am I doing wrong?"
I hear this question constantly, and it usually comes down to three common issues:
1. Your product isn't aligned with what your audience actually needs
The most beautiful, comprehensive digital product in the world won't sell if it doesn't solve a problem your audience is actively trying to solve right now.
I learned this lesson the hard way. My first attempt at a product was a comprehensive guide to newsletter monetization strategies. It flopped spectacularly. When I actually talked to my audience, I discovered they weren't looking for monetization strategies yet—they were struggling just to get their first 100 subscribers.
The solution? Step back and have real conversations with your audience. Send a simple email asking about their biggest challenges. Look at which newsletter topics generate the most engagement. Create your product to address the problems they're already telling you they have—not what you think they should care about.
2. Your audience doesn't trust you enough yet
Trust isn't binary—it exists on a spectrum. Your audience might trust you enough to read your free content but not yet enough to pull out their credit card.
This is completely normal and fixable. Keep showing up consistently. Keep delivering value. Keep demonstrating your expertise through your free content. Trust compounds over time.
Some of my most enthusiastic customers were subscribers who followed me for months before making their first purchase. They needed to see consistent value before they were ready to buy.
3. You didn't warm your audience up to the product
This is the single biggest mistake I see newsletter writers make: they create a product, mention it once in a newsletter, then wonder why sales are disappointing.
Here's the reality: you can't just drop a product announcement on an unprepared audience and expect sales to flow. People need context. They need to understand the problem deeply before they're ready for a solution.
I use a 7 to 10-day "warm-up" period before any product launch. During this time, I focus on highlighting the problem my product solves, sharing stories related to it, and getting my audience to recognize their need for a solution.
By the time I actually offer the product, my audience isn't surprised—they're primed and often eager to purchase because I've spent days helping them understand the importance of solving this particular problem.
This warm-up process is exactly what I teach in the "5-Day Digital Product Sales Launch Training" bonus included in my Digital Product Masterclass. It's the difference between launches that fizzle and launches that generate thousands in revenue.
When your audience is properly prepared, selling your product doesn't feel pushy—it feels like the natural next step in a conversation you've been having all along.
It’s Time to Break the “Starving Writer” Mentality
Selling digital products through your newsletter doesn't require you to become someone you're not or adopt aggressive marketing tactics that make you cringe.
It simply requires you to:
Recognize that selling is serving when you've created something genuinely helpful
Let go of the fear of unsubscribes – they're a natural part of building a focused audience of people who value what you offer
Remember that nobody is scrutinizing your "salesiness" nearly as much as you think they are
Position your products as natural extensions of the help you already provide for free
Prepare your audience properly before offering your solution
The biggest shift isn't tactical—it's mental. When you truly believe in the value of what you're offering, selling feels less like an uncomfortable obligation and more like an enthusiastic recommendation.
Think about the last time you told a friend about a great restaurant or a life-changing book. You weren't "selling" those things—you were sharing something valuable because you genuinely believed it would help them.
That's exactly how selling your digital products should feel.
I was terrified of selling to my audience eight months ago. Now it's one of my favorite parts of running my newsletter. Not because I enjoy "marketing," but because I love seeing the transformations that happen when readers become customers and implement my deeper solutions.
There's something incredibly rewarding about getting emails from people who've used your product to achieve real results—far more rewarding than just collecting subscriber numbers.
📌 Ready to Sell Your First Digital Product?
If you've been hesitating to create and sell products to your newsletter audience, I want to help you break through that barrier.
I've taken everything I've learned from generating over $50,000 in digital product sales (starting from zero subscribers) and distilled it into a comprehensive, step-by-step system specifically designed for newsletter writers.
The Six-Figure Digital Product Masterclass isn't about complicated marketing tactics or pushy sales techniques. It's about creating genuinely valuable products and presenting them in a way that feels natural and aligned with the relationship you've built with your audience.
Inside, you'll discover:
The exact validation process I use to ensure products sell before I create them
My weekend product creation framework that helps you build high-quality products in days, not months
The 5-day warm-up sequence that primes your audience to buy (without feeling "sold to")
Simple templates for everything from product outlines to sales emails
This is the same system I've used to create multiple successful products, and that dozens of other newsletter writers have implemented to transform their Substacks from passion projects into profitable businesses.
Plus, these special bonuses disappear tonight (May 15th) at midnight:
"5-Day Digital Product Sales Launch Training for Writers" — This method ensures your product sells by properly prepping your newsletter audience
"Six Figure Digital Product Brainstorming Template" — This template helps you mine your existing newsletter content for product ideas your audience will actually pay for
You can join below and grab the class + bonuses:
But regardless of whether you join us inside, I hope this post helps you move past the fear of selling. Your knowledge is valuable. Your solutions matter. And your audience deserves the chance to work with you more deeply if they choose to.
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