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Our paid newsletter right with AI just crossed $350,000 in annual recurring revenue and we're on track to hit 400,000 in the next couple months. In this video, I'm going to show you the five growth strategies that we've been using in 2025 to become the number three most popular education newsletter on Substack. So you can build a multi six figure paid newsletter too. Now, real quick, I've already created a video on the fundamentals that you need to execute in order to build a low six figure paid newsletter on Substack. So if you're a be, I would watch that one first. In this video, I'm going to share some of the more advanced things we're doing in 2025 specifically to generate more revenue from our Write with AI list, attract more new subscribers from inside Substack's ecosystem, and then upsell customers on other relevant products and this really cool little flywheel that we came up with to squeeze even more juice out of our product launches. I think paid newsletters are one of the most powerful business models for digital writers. So if you want to learn what's working in 20 and growth strategies for building your paid newsletter to multiple six figures in revenue, here you go. So there are five things we started doing at the beginning of 2025 that really caused right with AI to start growing so fast. Quarterly digital product drops added a founding member offer, created a master prompt library so you can find what you're looking for really quickly, added a value welcome email sequence plus some sort of incentive, and then started ramping. Substack notes, before we started doing these things you can see here, growth had sort of plateaued. We spent Almost all of 2024 hovering around 300,000 in annual recurring revenue. But once we started doing these five new things, you can see revenue started climbing again and it hasn't slowed down since. So 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. The first is quarterly digital product drops. So this is a huge missed opportunity for paid newsletter writers on Substack. Yes, your paid newsletter is the core product. You know 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 all sorts of things. You could upsell people on low ticket digital products like template packs or worksheets or ultimate guides. You could upsell people on low ticket courses niching down On a specific skill or problem or platform. You could also upsell people on paid webinars like a live workshop or a Q and A session. We now aim to do some sort of digital product drop each quarter, so every three months. And we use a really simple process for coming up with ideas on which product to create next. Let me give you an example. In 2024, we created this prompt engineering playbook, basically a text and video course showing subscribers our process for creating AI prompts from scratch. Write high quality content. Now, 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 this product because after running write with AI for almost two years, 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? Okay, 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. And then we wrote up a launch offer email about the product and published it on substack and then sent it to both our free and paid list. Then we created a landing page for the product on SamCart. And quick side note, you can use whatever platform you want to create landing pages and sell digital products with. We like SamCart, but use whatever you're comfortable with. The important part is that you have a dedicated separate landing page for the product so the customer knows it's something separate and valuable. We charge 249 for the product, and this one digital product drop unlocked an additional $90,000 in revenue. That's almost a third of right with AI's yearly subscription revenue, it's extremely impactful. And if we assume we can do this one time per quarter, so that means four digital product drops per year, then we end up earning the same amount of money as all of our paid newsletter subscription revenue. Which means just by executing the strategy, we basically 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 big strategy is executing quarterly digital product drops to your list. You can do them quarterly, you could do them every six months, you could do one product a year. It doesn't matter. More products equals more revenue. Now the second growth strategy that we started executing is we added what's called a founding member tier, and this led to a $25,000 increase in subscription revenue in just the first two months. When you turn a newsletter paid on substack, you can set up monthly or yearly price points. But something else you can do is create a founding member tier, which is usually one and a half to two times 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 right with AI into a seven figure vertical by the end of 2025. The flywheel goes like this. First, create a more expensive founding member tier. We priced ours at 350. Second, make the core benefit of the founding member tier that you get free access to all future digital product drops. And then third is every time you drop a digital product and you 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 of our other digital products for free. This is how you start to double monetize. Because people are either buying the new product that you're dropping, or they're seeing it as an incentive to become a founding member. So let me walk you through how this works. First, you can create these 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 ghostwriters prompt pack, or an entire text and video course like our prompt engineering playbook. We tag the launch post so it gets organized in this 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 that can just 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 big and bigger archive of digital products. So that's the second strategy is 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 the library goes. So this is important for two reasons. First, the biggest reason why free subscribers don't upgrade and become paying subscribers is is they don't know if you've written about the thing that they're most interested in. So you need to quickly and easily show all new subscribers. Yes, we have the thing that 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, right? You just. You keep scrolling and scrolling and scrolling. 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 here's what we did. We wrote a post welcoming new subscribers to write with AI, and we pinned it to the top of our substack. It's really important to optimize for people who have no idea who you are or what your newsletter is about, or how you can help them. Inside that post, we reward new subscribers with three resources to get started writing with AI. We give them a welcome gift, which is a huge social content prompt template, essentially a link to join our free educational email course where we share some of our favorite ChatGPT prompts for writing. And then third, we share a link to our beginner Start Writing with ChatGPT mini course, and we remind them that they get this free if they become a paying subscriber. You can make these resources anything you want, but I would definitely recommend adding in some sort of. Here's a really cool free thing to help you get started right there in your welcome post. Below that we then link to our complete Write with AI prompt library. So what we did was take every single Write with AI issue and prompt that we had created and we organized it by topic. If you want to grow your audience with AI, read these. But if you want to monetize your content with AI, read these. Or if you want to build your digital library of content with AI, read these. Or if you want to improve your writing and publishing process with AI, read these. Basically, it's just a master repository of everything that you should read organized by content bucket in one place. It seems so simple, but we didn't have this asset created for a long time and people just kept asking for it over and over and over again. And then as soon as we created it, 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 the thing they were looking for. Now the fourth strategy is where things start to get a little advanced. Substack doesn't have great automation capabilities. Its 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 Beehive, it's very limited. But we found a workaround inside substack settings. They allow you to tweak four different types of welcome emails. The welcome email to paid subscribers. The welcome email to free subscribers. The welcome email to imported subscribers. So for example, when someone joins our Write with AI educational email course which is hosted on ConvertKit, we can't connect that list to substack. So every week we have a VA take those subs and import them into substack manually, which triggers this welcome email. And then fourth is you have a welcome email for founding members. The big change that we made was to the welcome email to free subscribers. So here's how it works. When someone new subscribes to write with AI, they get sent this welcome email. Inside the email, we remind them of that free gift, the AI prompt that creates 101 proven social content templates. We give it away for free. But 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 are they looking for. We want to know that so that we can create content and prompts that help them. Right? Then after they complete the survey, they unlock the free gift, which we host here on Notion. This in itself was a huge upgrade. Adding a free welcome gift and a short survey. It's what allowed us to start gathering data. We better understood our readers. We created content that resonated more and more with the people that were subscribing. Right, that was a huge upgrade. But the thing that really moved the needle and unlocked another tranche of incremental revenue was we added an upsell at the bottom of the free welcome gift. So we give them this giant prompt and accelerate their AI writing journey. We give it to them for free. And then at the very end, we speak to the problem. We have seen so many people struggle with over and over and over again, which is, okay, 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. We called it the Digital Writers Voice Lab. And we added it as an upsell at the end of their free gift, the exact moment when they are most likely to want to take the next step to solve that next problem, right. They have this huge prompt and now they're aware, oh, I love this, but how do I get it to write in my voice? Well, here's a product that helps you solve that problem. We priced it at $49 and instantly we added another three to six grand in incremental revenue per month. Which might not seem like a lot of money, but let's do some napkin math. Let's take the low average and call it an extra four grand a month. Well, right now, right, with AI is doing approximately 30 grand a month, which means an extra four grand a month is a seven and a half percent increase in revenue on autopilot and pure margin. You build it once and it runs forever. So that's the fourth strategy we executed. We added 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, 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 subscribers, but it's also a great way to gather data about who's reading your newsletter so you can continue to write content that gives them what they're looking for over and over and over again. Which leads to the fifth strategy. And this is really a traffic and net new subscriber acquisition strategy. At the beginning of 2025, we started really ramping up Substack Notes. Now, what are notes? Basically, it's Substack's version of X. It's short form content posted from your account and it appears in a newsfeed on the homepage of Substack. But here's why notes are such a great acquisition strategy. When you're scrolling Substack's newsfeed and you see a post from someone and you hover over their name, it presents you with two options. You can message them or you can subscribe to them. There's no apparent follow button. And this is a really unique feature. Imagine if every person who followed you ON X or LinkedIn or any social platform 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 way more on Substack. Like we ramped up to two, three, four times a day 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. Quick Context I've been following Substack since the very beginning, way back in 2019 when they first raised $15 million for their series A from Andreessen Horowitz. I reached out to the founder, we bounced emails on the future of paid newsletters. I was an early user of the platform. I built two of the most successful paid newsletters on Substack, Category Pirates and now Write with AI. And at this point the platform has been around long enough, they've raised enough money, they've attracted enough writers where I know just having watched these cycles over and over again over the past decade, Substack's not going anywhere. And now that you can post and create short form content on Substack, it's essentially a social content platform in and of itself. So we're allocating a lot more resources to ramping up our social content on Substack moving forward. And I really strongly recommend that you do the same. 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 newsletter is to just write really great content. And I mean, yeah, 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 that you can use to monetize your content and extend customer lifetime value. So I hope this helps give you some new strategies that you can use and apply them and get building right away.