Marketing secrets behind our $300k/Year Paid Newsletter (Write With AI)

How do you market a six figure paid newsletter? What marketing strategies do you use to attract free subs and convert them to paid subs? Well, I can tell you because our paid newsletter write with AI just crossed $300,000 in annual recurring revenue. And in this video, I'm going to get super tactical and walk you through exactly how we market our paid newsletter, how we get customers, how we upsell them, how we convert, you know, free to paid, and all the different little copywriting things that we do to incentivize people, how you think about offer creation, what you should pay while behind your paid newsletter, things like that. So first, it's important to understand just the model and almost supply chain for a paid newsletter business. The first component is you have to be writing somewhere for free. Doesn't matter where it is. X, LinkedIn, Instagram, Facebook, could be Snapchat for all I care. All you're doing is generating traffic, then you're driving that traffic to some sort of free newsletter. And the purpose of that free newsletter is A, to take all of the people that enjoy reading the short form stuff on social and show I can give you more. Right? And B, is to get them on an email list. Because you sort of need them on an email list in order to do some of these things to incentivize them and educate them on why they should upgrade to paid. And usually there's two types of content that people are ultimately buying when it comes to a paid newsletter. You know, what makes them pull out their credit card and decide to become a customer. The first is some sort of exclusive content. So this could be data, research, trends, insider stories, behind the scenes content, things that you wouldn't normally share out in public, or maybe things that require a bit more context, a bit more explanation. They certainly don't lend themselves well to like Twitter short form for example, but usually it's something like that, something exclusive or the other type of content is expert content. So think of this as you're paying to have coffee at scale with someone who has decades of experience or has really unique information or knowledge or insight about a specific industry, a specific problem. You're like, I want to hear it from you, right? So it's almost always either exclusive content or expert content. And usually whenever I start getting into this, you know, the question people ask is, okay, well should my free newsletter be separate from my paid newsletter, you know, and can they be both? Which is better? What platform should I use? Should I use substack? Should I use ConvertKit? Should I use Beehive? So let's break this down real quick. So first of all, our paid newsletter write with AI is on Substack for two reasons. One is that Substack works sort of like a newsletter feed, if you think about it that way, where both of your free issues and your paid issues are organized into one feed. And the primary reason and why you would do this and why Substack does this is because they know, and we know as the creator or the writer, that the reason someone's going to upgrade to paid is they need to first read some of the free stuff. They need to know is this something that I'd be interested in so it makes sense to curate them into the same feed. And then second is Substack, you know, it's not just a tool. It has this growing community element. And so there is a lot of benefit for us in using Substack because we've found that we can then tap into some of that larger distribution. And I really like Substacks ecosystem. It's very clear that they are trying to not just be a tool, but a publishing platform. And so whenever I see stuff like that, I tend to like to deploy effort there and to double down on those types of platforms because I know, you know, for context, Substack raised a ton of money, venture capital, and they're pouring all that money into hoping to build this publishing platform. And so whenever I see a ton of venture money going into a platform, I know you're going to push this really hard. You're trying to incentivize people to use this. I'm probably going to get a nice little traffic arbitrage by tapping into this. And so that's why we chose to build right with AI on Substack. The reality is though, you can do this on ConvertKit, you can do this on Beehive. A lot of these platforms have similar features. But I think a cool data point is that almost 20% of our paid subs are coming from Substack's internal recommendation feature feature engine right now. So that means 20% of the people that are paying us, we didn't drive the traffic to from social. They are coming from Substack's ecosystem and exploring around. They discovered right with AI and then they chose to subscribe. That's pretty powerful. 20% isn't nothing. And Convertkit and Beehive have sort of similar features. But I think truthfully that this recommendation engine substacks is the best and it also leads to the highest quality of subscribers. So that's why I Like it. Now, if you're trying to figure out which platform to use for you, here's a really easy framework to make the decision. So first, if all you want is just a paid newsletter, you're like, I just want to write, I want to paywall some of it. You should use Substack. It's the easiest to use. It has a very simple feature set. It's very easy to get up and running. It's nothing like super crazy advanced. And that's sort of the benefit of it. If you want to build a digital products business and you want your newsletter to essentially be the engine of that business, I would recommend using ConvertKit. This is what we use for all of our businesses. All of our primary email funnels are built on convertkit. We have funnels for ship 30, we have funnels for PGA. We have funnels for typeshare. We have separate funnels even for right with AI in some circumstances. But the majority of the business is really us just driving traffic to sneaky to substack. We have one funnel where we collect emails through a educational email course and then we tell people about right with AI. So ConvertKit is a really, really great engine for digital product businesses in the sense that you're collecting emails and then you're upselling people on products. You're putting them into FOMO sequences. You can have abandoned cart sequences. And these are more advanced things. So if you're starting in the beginning and you're like, I just want to be able to paywall some content. You don't need all of this. Just use substack. But if, and I wouldn't even make this decision day one, I would say as you get going, if you find that you need some of these more advanced features, I would use ConvertKit. Beehive is a little bit of the in between of these two. And in my opinion, Beehive is actually best not really for a quote unquote paid newsletter, but for a publication. If you notice, a lot of Beehive's features are really centered around building the landing page of your quote unquote paid newsletter. But really it is actually more like a publication. And a great case study here is Milk Road. Milk Road is a crypto paid newsletter, but really it's a crypto publication and it was built on Beehive. But that's a great thing to look at as the type of thing you can build on Beehive. And Beehive has a bunch of these advanced features. I think it's, I think it's really Good if you enjoy having all of those different levers to push and pull. But if all you want is just a simple paid newsletter, again, I would go with substack. So think of Substack as the really simple option, ConvertKit as the really advanced option, and then Beehive as sort of the in between. All right, next, how often should you be publishing newsletters? So very simple cadence that anyone can follow is if you want to build a paid newsletter business, you should aim to write one free newsletter a week and one paid newsletter a week for two specific reasons. So first is you want to consistently publish free content because that is your marketing engine. That's how you're going to get people introduced to the things that you write about. That's how you're going to get distribution onto your paid newsletter. Right. Or you're just quote, unquote, newsletter feed. You need to write things for free to bring people in. Then you want to have the second thing go out each week, which is the product itself. Right. It's the actual paid newsletter. So you go, all right, I'm getting you into the ecosystem. Now, here's the thing that I'm promising you, right here is the paid newsletter. And one of the benefits of and why I love the paid newsletter model is that the longer that you write both free issues and paid issues, both of these archives grow and grow and grow. It's a little harder to understand on the free side. But on the paid side, it's very easy. When you start a paid newsletter, say you have one issue or two issues behind the paywall, well, that's sort of valuable. But when someone pays, they are buying the next thing or the next things that you're writing, right? That's really the trade. But the more paid newsletters you write, the bigger your archive gets. That means that the immediate value of your paid newsletter goes up and up and up over time. So each new person who pays you isn't just getting access to the next paid thing that you write, but they're also getting access to all of the things that you've written in the past, which makes the purchasing decision easier and easier. That's why I love paid newsletters as a business model, because they really compound in value over time. Now, whenever I explain this cadence, of course, everyone asks, well, could I publish two free newsletters a week? Sure. Could you publish two paid newsletters a week? Sure. Could you publish five paid newsletters a week? Sure. Could you publish a paid newsletter once every other week? Sure. The reality is all of these cadences work. The question that you need to ask, and I like thinking of this in a very simple equation, the question you need to ask is what is the value that I'm promising? And value equals the quality of information that I am giving the reader divided by the time of consumption. So how long it takes them to get through it. Or said really simply, value equals information divided by time. Okay? And if you're paid newsletter, I'll walk you through two different examples. If your paid newsletter is a financial paid newsletter and you are sharing cutting edge stock tips, right? Well, in that scenario, those stock tips or those trades might only be able to get executed in a 24 hour window or a 48 hour window or maybe like a week long window, right? So it makes sense to share more information to the reader on a faster basis, right? Because in that scenario, value equals information divided by time, right? The information that you're giving them doesn't take very long to consume. You're like, this is the stock you should buy. Like, great, thanks. So you could send that every single morning and it wouldn't be overwhelming to the reader, right? On the other end of the spectrum, this is what we ended up doing. The first paid newsletter that I built a different business was Category Pirates. And with Category Pirates, we did the complete opposite. We were not writing short emails, we were writing essentially 10,000 word paid newsletters. We ended up calling them mini books just to set the expectation with readers. We were like, when this hits your inbox, this is not a newsletter, this is a mini book. Because these things are so long and so jam packed with thinking and value and frameworks. And in that scenario, value equals a ton of information, but also requires a lot of time to consume. And so if we were to go, you know what, let's, let's ramp up the volume, let's send one of these a day to readers. Well, they would find that really overwhelming because it's actually too much, right? Which is very different than sending someone one short stock tip every morning. And so what we ended up doing with category pirates, we started by doing it on a weekly basis. And we found that even on a weekly basis it was too much. So we ended up getting to a publishing cadence of publishing one of these mini books, AKA paid newsletters, and every other week. But that made sense because the value equals information divided by the time investment, right? So when you're trying to figure out, well, how much should I write? What should my cadence be? You need to start with that and figure out, well, what is the value that you're promising. What is the quality of information you're giving the reader, and what is the time investment for them? And so the higher quality the information, the lower time investment, the faster the cadence can be. Right? Whereas the higher the time investment, the lower the cadence should be. But either way, it doesn't really matter if it's weekly or biweekly or two times a week or five times a week or whatever it is. You still want to hit that barbell of some free and some paid, because the free is your marketing engine, and the paid is the actual product, which leads to how do you upsell free readers to paying subscribers? And I'm gonna get super tactical here, because if you just do these one or two things, this is what drives 90% of the outcomes. So the first is the most effective way to bump free subs to your paid list is to just send them snippets of the paid newsletter every time you write it. And Substack has this really cool feature where you can insert. You can choose where you insert the paywall. And so what we do is with write, with AI every single week, we have some sort of free content that goes out. And then when our paid newsletter goes out, we just intentionally put the paywall about 25, 30% of the way through and then send it to the whole list. So all the paying subs get the full paid newsletter. They're on the paid list. That's what they're paying for. But then the free subs are also receiving that. But there's a paywall after that 30% mark. And so they're getting the snippet of the paid thing. And if you just think about it, how do you get more people to buy? Well, you remind them that you have something for sale. And so that model, you know, it's such a simple thing, but I find not very many people choose to do it. But all you have to do is just keep reminding your free list, hey, by the way, yeah, you're getting the free thing every week, but we have the paid thing over here. And let. Let me just keep giving you the snippet. So in Substack, you just take that paywall, you put it about 30% of the way page of the. All the way down the page, and then you send the paid newsletter to your whole list. Paid people get it, free people get the snippet. Which leads to something even more tactical that you can do, though. And I think that this, like, the first thing is just make that the habit. Right? But this is the more advanced like in the weeds. This is how you start to optimize. What you want to do is you basically go back through the paid newsletter that you've written and very intentionally drop the paywall wherever there's a cliffhanger. So you're not just putting the paywall arbitrarily 30% of the way down the page. What you're doing, and I'll walk you through an example here, is you essentially begin the paid newsletter by walking the reader through whatever thing you're explaining. And then right as you're about to give them the thing, right as you're like, you go, oh, okay, and here's my framework for doing it, or here's the prompt that we use for doing it right? Or here's the checklist that. That we go through. Right as you're about to give them something really tangible, really specific, that's where you put the paywall. Because it's that moment that the reader sits there and goes, oh, I now feel the FOMO feeling, right? Like you explained a little bit of the idea. And then you're like, and this is how you would go about it. And then let's move into the next step stage. And this is the thing that I would use. And then, like right before it, that's where you put the paywall. And this is a very subtle little copywriting thing where we've seen the data internally on. On this, with Write, with AI, where when we do this intentionally, the conversion rate of those newsletters is always so much higher than when we just arbitrarily throw the paywall somewhere. And so there's sort of an art to writing your paid newsletters, and you'll get better and better at this over time, but there's an art to, you know, entering the paid newsletter. Here's the idea we're going to talk about today. I'm going to give you a little bit in that first 30% so that this feels substantial. There's value here. But then right as I'm about to give you the answer, right as I'm about to give you the tangible thing, I put the paywall. And if you do that every single week and you send that snippet with that cliffhanger paywall to your free list, you're going to see, like, the better that you get at that, the higher and higher the conversion rate's going to be. So that's. It's a. It's a small thing, but that's one of those easy levers that you can push and pull another really tactical thing that you can do. And this is just sort of like baseline. Best practice is you want to have a couple CTAs that you just copy paste as a template at the end of every one of your newsletters and every one of your paid newsletters. So for example, Our Write with AI newsletter ends with P.S. can you refer this issue to a friend? P.S. can you gift this paid newsletter to a friend? And then one more PS Please comment with ideas you'd like covered in future issues. Biggest takeaway from this newsletter, et cetera. And these are really simple things. It's not like any one of these is going to make your paid newsletter, but it's just a great best practice. It's like, why would you not do that every single week? So you just want to bake in little referral, slash engagement tactics into your workflow. Um, and also it's just helpful to remember whenever you're creating content, no matter how good the content is, people aren't going to remember to send it to their friends or remember to comment unless you prompt them. So it's such a simple thing, but you have to be the one to remind them over and over and over again. Otherwise they're not gonna, they're not gonna do it. And then the very last thing you know, this is one of those. It's so simple, it's complicated is on the front end, marketing side, how we drive traffic to write with AI is all we do is once a day I write something short form on x, sometimes on LinkedIn, but really we use X to drive a lot of our traffic. I know I'm going to get this question. It's not because like, oh, LinkedIn sucks for driving traffic and is X better? No. Like any platform you can make work, we just tend to prioritize X for this because we prioritize LinkedIn for PGA. I write some sort of short form post about writing with AI and then I link to our paid newsletter or I link to our educational email course where I give away some of my favorite prompts. And then once people are on our list, we tell them, hey, by the way, we have a paid newsletter called Write with AI and that's it. Like that is the whole traffic engine. We don't run ads. We don't have some big fancy affiliate marketing army. We don't have influencer partnerships. All we do is, is just write on social about the same topic in short form and then remind people to hop over to our paid newsletter. And obviously the paid newsletter needs to be high quality Enough. It needs to be good enough to warrant someone wanting to pay. But a lot of times, and I talked about this in a, in a previous video that I'll link here, is when you're thinking about what makes your paid newsletter, it all comes down to what you're promising the reader. It needs to be tangible, it needs to be objective, it needs to help them solve a problem. And so when you do that, right, that's 90% of the game. The rest of it is really easy. It's like, write on social platforms about the same topic, drive the traffic, send snippets of the paid thing to your free list, and remember to paywall right at the cliffhanger so that people feel that little bit of FOMO in every single issue and go, oh, I actually want this. Let me upgrade to paid. And if you do that, that's how you grow a really great, successful paid newsletter. That is everything we've done to build right with AI to 300k a year. So I'm not withholding anything. There's no part of our funnel that I'm not telling you about. There's no secret sauce or this magical button that I'm pressing that you don't know about. Okay? It's literally just that flow and we just repeat that flow over and over and over again. And right with AI just crossed 300k annual recurring revenue. We've been at it for probably a year and a half. So that's everything. I just wanted to share our entire marketing system for right with AI I hope this helps you with your own paid newsletter. And, and the biggest thing that I can emphasize is don't get caught up with all this shiny object, like all the different things you can do with marketing and some big fancy funnel. It's really not about that. It's just write about the topic that you know a lot about for free on social. Drive that to a newsletter, remind your free subscribers that you have this paid thing for sale and make the paid thing really tangible and really objective and help them solve problems and you'll have a successful paid newsletter.