Our $400k/Year Newsletter Strategy In 2025

Plus: Your Custom Growth Prompt

Paid newsletters are one of the most powerful business models for digital writers.

And if you want to learn what’s working in 2025, and the growth strategies for building your paid newsletter to multiple 6 figures in revenue, there are 5 things we started doing at the beginning of this year that have caused Write With AI to blow past $400,000 in ARR.

And if you stick around to the end…

I’ll give you a ChatGPT prompt you can use to generate custom growth strategies for your newsletter—based on your audience, platform, and revenue goals.

But before I get into the details, I want to say THANK YOU.

Write With AI exists because of you.

If you’ve ever read an issue, replied to an email, shared something we made, or upgraded to a paid plan—you helped make this possible.

We’re grateful.

Now, let’s get into it.

5 Paid Newsletter Growth Strategies For 2025

We spent almost all of 2024 hovering around $300,000 in annual recurring revenue.

But once we started doing these 5 things, our revenue started climbing again—and it hasn’t slowed down since. In fact, I made a video a few weeks ago (when we were at $360k ARR) to show you these exact tactics.👇

Today?

We’re at $400K ARR and we just bumped up to the #2 most popular education newsletter on Substack.

Looks like these strategies are working!

Here they are:

1. Quarterly Digital Product Drops

2. Added a Founding Member Offer (+$25K in 2mo)

3. Created a Master Prompt Library (find what you need fast)

4. Added a “Value” Welcome Email Sequence + Incentives

5. Ramped Substack Notes (+1K new subs / wk)

Let’s walk through each one so you can understand how it works and how you can do something similar inside your own paid newsletter.

1. Quarterly Digital Product Drops

This is a huge missed opportunity for paid newsletter writers on Substack.

Yes, your paid newsletter is the core product—people are paying a subscription fee to read your content.

But it doesn’t have to be the only product.

You can unlock a lot of incremental revenue by also upselling subscribers on things like:

• Low-ticket digital products—like template packs, worksheets, and ultimate guides

• Low-ticket courses—niching down on a specific skill, problem, or platform

• Paid webinars—live workshops and Q&A sessions

We now aim to do some sort go digital product drop each quarter, so every 3 months, and we use a really simple process for coming up with ideas for which product to create next.

For example, the Prompt Engineering Playbook—a text & video course showing you our process for creating AI prompts from scratch to write high-quality content.

How did we come up with the idea for this digital product?

Well, as I like to say… it’s so simple, it’s complicated.

We created it because because we kept hearing the same question over and over again:

“Dickie… Cole… I love your prompts, but how can I learn to create my OWN?”

So, how do we answer this question at scale AND unlock more revenue?

By creating a digital product!

It’s so simple people make it complicated.

But I promise you, if you have a paid newsletter, right now you have an entire group of people who would love to give you more money… if you would just create a digital product that answers their biggest question.

So we created this product to answer that question.

• We gave it a name to make it tangible, and called it The Prompt Engineering Playbook

• We wrote up a launch / offer email about the product and published it on Substack—and sent it to both our free and paid list.

• We created a landing page for the product on SamCart

• We charged $249 for the product

And this 1 digital product drop unlocked an additional $90,000 in revenue.

That’s almost a third of Write With AI’s yearly revenue!

Extremely impactful.

And if we assume we can do this 1x per quarter, that means 4 digital product drops per year end up earning the SAME AMOUNT as all of our paid newsletter subscription revenue.

Which means just by executing this strategy, we double the business.

Now, you might be wondering, “Cole? Won’t you run out of digital product ideas?”

Yes, we will run out of ideas as soon as our readers run out of problems.

And after a decade of being an entrepreneur, let me tell you… people never run out of problems.

So that’s the first strategy, is executing quarterly digital product drops to your list.

• You can do them quarterly.

• You can do them every 6 months.

• You can do 1 product a year, doesn’t matter.

More products = more revenue.

Now the second growth strategy we started executing is we added what’s called a Founding Member Offer—and this led to a $25,000 increase in subscription revenue in the first 2 months.

2. Founding Member Offer

When you turn a newsletter paid on Substack, you can set monthly or yearly price points.

But something you can also do is create a Founding Member tier, which is usually 1.5-2x the annual price but comes with a bunch of additional benefits.

Now, here’s where things get really cool—and I think this flywheel is what’s going to turn Write with AI into a 7-figure vertical by the end of the year.

The flywheel goes like this:

• Create a more expensive Founding Member tier—we priced ours at $350.

• Make the core benefit you get free access to all future digital product drops.

• And then every time you drop a digital product and pitch your list, remind them: “You can either buy this product OR for essentially the same price you can become a Founding Member and get this PLUS all our digital products for free.”

This is how you start to double-monetize, because people are either buying the new product or they’re becoming a founding member.

So let me walk you through how this works:

First, you can create different sections at the top of your Substack, so we created one called Products.

Next, every time we create a product—doesn’t matter if it’s just a Notion hub like this LinkedIn Ghostwriter’s Prompt Pack, or an entire course like The Prompt Engineering Playbook—we tag the launch post so it gets organized in the Products section of our Substack.

Then at the bottom of each product launch post, we remind potential customers:

• “You can buy this product”

• “OR… you can upgrade your subscription, become a Founding Member, and get this product—along with all our other products—for free.”

And you can see how this is a flywheel you can keep spinning forever.

• The more products you launch, the more incremental revenue from product sales.

• But also, the more products you launch, the more incentive there is for people to upgrade to the Founding Member tier—because they instantly unlock a bigger and bigger archive of digital products.

So that’s the second strategy, adding this Founding Member tier and creating this flywheel of products inside our paid newsletter.

The third strategy—and this makes more sense once you’ve been running a paid newsletter for more than a year or two—is making it easy for new subscribers to see how deep our library goes.

3. Created a Master Prompt Library

We did this for two reasons:

• First, the biggest reason why free subscribers don’t upgrade and become paying subscribers is they don’t know if you’ve written about the thing they’re most interested in. So you need to quickly & easily show all new subscribers, “Yes… we have the thing you want.”

• But second, because the bigger your paid newsletter archive gets, the harder it is for subscribers to find what they’re looking for. So it’s really helpful, both for upgrading free subs into paid subs, but also retaining paid subs over the long term, to make it easy for them to navigate your library of content.

So what we did was take every single Write With AI issue & prompt and organized it by topic.

• If you want to grow your audience with AI, read these.

• If you want to monetize your content with AI, read these.

• If you want to build your digital library of content with AI, read these.

• If you want to improve your writing & publishing process with AI, read these.

Basically just a master repository of everything you should read, by content bucket, organized in one place.

It seems so simple, but we didn’t have this asset created for a long time, and people kept asking us for it over and over again.

As soon as we created it, boom—new paid subs started going up.

So that’s the third strategy, is just by creating this simple organized library of all our content, we saw more free subscribers convert to paid—because now they knew where they could find what they were looking for—AND paying subscribers stay longer.

Now the fourth strategy is where things start to get a little advanced.

4. Added a “Value” Welcome Email Sequence + Incentives

Substack doesn’t have great automation capabilities.

It’s simplicity is why it’s such a great platform for beginners, but when it comes to running email campaigns or doing any sort of list nurturing like you would in ConvertKit or Beehiiv, it’s very limited.

But, we found a workaround.

Inside Substack’s settings, they allow you to tweak 4 different types of Welcome emails:

• Welcome email to paid subscribers

• Welcome email to free subscribers

• Welcome email to imported subscribers

• Welcome email to founding members.

So the big change we made was to the welcome email to free subscribers.

Here’s how it works:

When someone new subscribers to Write with AI, they get sent this welcome email.

Inside the email, we give them a free gift—an AI prompt that creates 101 proven social content templates. And in order to unlock the gift, they have to fill out a short survey—which we host on Typeform.

Now, why do we do this?

Because we want to gather data! We want to know who is subscribing, and what they are looking for, so we can create content & prompts that helps them.

Then after they complete the survey, they unlock the gift—which we host on Notion.

This, in itself, was a huge upgrade—adding a free welcome gift & a short survey, allowing us to gather some data about our readers. But the thing that really moved the needle, and unlocked another tranche of incremental revenue, was adding an upsell at the bottom of the free welcome gift.

So we give them this giant prompt, and accelerate their AI writing journey.

And then at the very end, we speak to the problem we have seen people struggle with over and over again, which is, “OK great… but how do I get AI to write in my voice?”

So, we ran the playbook back:

• We created a digital product that solved that problem

• We named it something tangible: The Digital Writer’s Voice Lab

• And we added it as an upsell at the end of their free gift—the exact moment when they are probably most likely to want to take the next step or solve that next problem

We priced it at $49, and instantly that added another $3-$6K in incremental revenue.

Which might not seem like a lot, but let’s do some napkin math.

• Let’s take the low-average and call it an extra $4 grand per month.

• Right now, Write with AI is doing approximately $30 grand a month.

• Which means an extra 4 grand a month is a 7.5% increase in revenue.

On autopilot and pure margin.

Build once, runs forever.

So that’s the fourth strategy we executed:

• Add a welcome email

• Which sends people to a short survey

• To unlock a free gift

• That then upsells them on a low-ticket digital product

Now, if this is too advanced for you, don’t worry about having a product for sale. But I would strongly recommend writing up a really great welcome email and at least sending people to a short survey in exchange for a free gift.

It’s a great way to reward new subs, but also gather data about who is reading your newsletter so you can continue to write content that gives them what they’re looking for.

Which leads to the fifth strategy, and this is really a traffic and net-new subscriber acquisition strategy.

5. Ramped Substack Notes

At the beginning of 2025, we started really ramping up Substack Notes.

Here’s why Notes are such a great acquisition strategy:

When you are scrolling Substack’s newsfeed, and you see a post from someone and hover over their name, there’s only 2 obvious options:

• Message them

• Or subscribe to them

Technically, there is a “Follow” button, but it’s barely noticeable.

What stands out more is the “Subscribe” button, which means a lot more people end up joining your email list instead of just following you silently. This is a really unique feature. Imagine if every person who followed you on X or LinkedIn automatically got added to your email list, and you could contact them directly via email.

That’s essentially what’s happening on Substack.

As soon as we noticed this, we started cross-posting content 2-4x on Substack.

And it’s had a huge impact on net-new subscriber growth.

Over 35% of all Write With AI subscribers have come from inside Substack’s platform and through some sort of feature, Notes being the biggest one.

So we’re allocating a lot more resources to ramping up our social content on Substack moving forward, and I recommend you do the same.

That’s it.

Those are the 5 big growth strategies we’re using in 2025 to grow Write With AI to $400,000+ in annual recurring revenue, but also build out our AI writing vertical and do over a million dollars in revenue by upselling other digital products & resources.

1. Execute quarterly Digital Product Drops

2. Keep nudging subscribers to upgrade to our Founding Member tier

3. Drive new subscribers to our Master Prompt Library, so they can find what they’re looking for fast

4. Probably continue to optimize our Welcome Email Sequence + upgrade that low-ticket funnel over time

5. And then keep ramping Substack Notes

I love paid newsletters, I think they’re such a cool business model—and I also feel like not very many writers fully understand these different nuances on the business side.

They think the key to having a successful paid newsletters is to just “write really great content.”

And yea, that’s a given. The goal obviously isn’t to write bad content.

But the writing is only a small part of the equation.

If you want to make hundreds of thousands, even millions of dollars from your paid newsletter, you have to understand all the different business models you can use to monetize your content & extend customer lifetime value.

So I hope this helps give you some new strategies you can use, and get started building right away.

Want Help Brainstorming Growth Strategies For Your Paid Newsletter?

The 5 strategies I shared above are what helped us blow past $400K ARR this year.

But depending on your niche, your audience, and your goals, the right growth playbook might look a little different.

So here’s a ChatGPT prompt you can use to generate tailored growth strategies for your newsletter—whether you're just getting started or already making thousands per month.