6 Step Checklist To Build A $100,000 Paid Newsletter On Substack

I have built two paid newsletters on substack to multiple six figures in annual recurring Revenue category Pirates to 200k per year and write with AI to 300K per year and after doing this not once but twice I finally feel like I have the framework for being able to launch new paid newsletters and scale them to six figures over and over again so if that's what you want to do here are the six steps to six figures on substack step one pick a topic attached to a traffic engine this is one of those ideas that is

so simple but people over complicate it you launch a paid newsletter how do you get people to find out about your paid newsletter well you have to write about the same topics for free somewhere else and if I could summarize a paid newsletter business that's pretty much it you write online for free about a topic you tell people I also write about this topic on my paid newsletter over here and then you do that every day multiple times per day for years so for example our paid newsletter write with AI how do we get people

to find out about write with AI well my co-founder Dicky and I write about writing with AI on x and then tell people oh and by the way we also write more about this over here and then we send people to our substack and we've been doing that once a day every day for almost 2 years and again it's so simple but people want to believe there's something more like Cole there's something you aren't telling me no the boring work is the moat the secret is consistency so if you want to build a paid newsletter

you need to attach it to a traffic engine AKA you need to write about those same topics for free somewhere else and then remind people over and over again by the way I also have this paid newsletter where I talk about the same topics just more in depth over here step number two make your newsletter tangible this is probably the hardest one for new writers to wrap their heads around so if this doesn't click right away that's fine I promise one day you're going to be walking through the grocery store looking for bananas and all

of a sudden it's going to hit you as a general rule readers value tangible ideas more than they value intangible ideas for example just notice how differently these two sentences feel in your brain sentence number one one I'll explain to you how to build your first paid newsletter or sentence two here's my six-step checklist to build $100,000 plus paid newsletter on substack it's the same idea it's the same topic but the first sentence is intangible I'll explain no you can't hold me explaining in your hands there's no weight to it it doesn't feel like an

object but the second sentence which is the title of this video for a reason is tangible I'm not explaining I'm giving you a six-step checklist which is the digital equivalent of me handing you a physical object it's a checklist you can hold it in your hands and so as a result you value it more which is probably why you clicked on this video too if you want to build a lucrative paid newsletter around a topic this is the secret you have to make it tangible so for example what was the original idea for write with

AI was it for us to explain how to write with AI no because that's intangible the idea and I remember where I was when it hit me because we were flying to Los Cabos for the 8 figure boardroom Mastermind like 2 years ago and the idea was to have a newsletter that gave writers chat GPT and Claude prompts okay what is a prompt a prompt is a tangible asset I'm not explaining things to you I'm giving you a digital physical object and that's all we do in every single issue of WR with AI we explain

how to do something and then we make it tangible by automating that idea in the form of a prompt and I promise that decision is probably 90% of the the reason why WR with AI has grown so quickly as a paid newsletter because it's extremely tangible when someone pays to subscribe they aren't just paying to read They're aware of the trade in their mind I give you $20 per month and you give me tangible chat gbt and Claud prompts which means if you want your paid newsletter to be successful you have to find a way

to make whatever thing you're writing about tangible now whenever I explain this people think about it for like 3 seconds and then their brain starts to hurt and they shout back I don't know how Cole it doesn't work for my Niche I don't want do it I can't do it I need my mom mom okay relax yes this means you have to use your brain for longer than 3 seconds I'm sorry but learning how to make your ideas tangible is one of the most powerful skills you can build as a writer because it means you

can monetize any idea at any time you can now sell digital air so just to show you how this works let's take some far out examples let's say you want to start a paid newsletter on and then we'll pick some really obscure ones let's say you want to start a paid newsletter on Kindle unlimited book Trends uh a paid newsletter on Russian literature and a paid newsletter on kitchen remodeling okay these are all great topics now how do we make them tangible well the question to ask is what object might each reader value so maybe

in our Kindle unlimited paid newsletter we can say in each paid newsletter I pick a different subcategory on Kindle and I give you a heat map of the most profitable keywords key phrases and content angles in that subcategory oh a heat map right that's tangible I can hold a heat map I can collect heat Maps I can touch and feel and hold the weight of a heat map okay boom our Kindle unlimited paid newsletter just 10x in perceived value all right how about Russian literature well instead of just saying I write about the art of

Russian literature which is what most people would do you can make this tangible by saying in each paid newsletter I pick a different Russian short story or novel I analyze it and then I give you an annotation guide of all the things you should highlight underline and circle as you read it so you can recognize all the different storytelling mechanisms being used oh an annotation guide that's tangible right and I bet even as I was saying it as soon as I said the word annotation guide you could feel it click in your brain right that's

the tangible thing you're listening for you see how this works okay let's do one more kitchen remodeling instead of saying I write about how to remodel your kitchen you make it tangible by saying in each paid newsletter I pick a different kitchen style explain why it works and which type of house this would work best in in and then give you an itemized purchase list so you can recreate the kitchen of your dreams in your own home oh an itemized purchase list right tangible so then once you figure out how you can make your paid

newsletter tangible that's what you lead with weekly Kindle unlimited heat Maps weekly Russian literature annotation guides weekly kitchen remodeling purchase lists and you can see this is how we execute our right with AI paid newsletter to a t weekly chat GPT prompts for writers step three the onefree one paid strategy so quick crash course on how substack works there's two things you need to understand the first is that substack is becoming a platform in and of itself so it's not just a publishing tool it's also an ecosystem of readers and writers so even though I

still think going back to step one that you need your own separate traffic engine like writing on X or writing on LinkedIn or Instagram or wherever you can tap into a lot of readers just by writing consistently on substack so for example for right with AI in our analytics we can see that almost 20% of our paid subscribers have come from inside substack Network again I still think it's worth having an outside traffic Source but I'm very bullish on this trend continuing to accelerate and I talk a lot about this phenomenon in my book The

Art and business of online writing but something that I look for whenever I'm writing online is who's backing the company and if you don't know substack is backed by some of the biggest Venture Capital firms in the world like Y combinator and Andre and Horowitz and substack has raised over $90 million so far quick crash course on Silicon Valley startup economics just follow the money if a platform raises $90 million they are going to spend a ton of those resources trying to get people onto the platform because they need their metrics to go up and

to the right to continue raising more and more money which is the attention Arbitrage opportunity substack is going to keep pouring millions and millions of dollars into getting more readers onto the platform because that's how they rationalize their valuation which is why I am going to keep building our presence here to ride that wave of increased detention so if you think of substack as a distribution platform in and of itself then the next question is well how do you get the readers on substack to find out about your paid newsletter you write one free newsletter

per week and you write one paid newsletter per week and you do that consistently forever for a couple reasons the one free one paid strategy works so well because every time you hit publish you're tapping into substacks explore algorithm increasing the chances of the next reader discovering who you are and discovering your paid newsletter but the one free one paid strategy also works well because your free content is what acts as the appetizer to your paid content which is like the main course so for example when you go to someone's substack the first thing a

new reader does because they can't read the paid content is to look for something free so you can get a sense of what that person writes about so you can get strategic here and make some of your best content free and then pin it to the top of your substack so new readers immediately understand the value of what you write about for example when I was building category Pirates this is what we did we wrote this massive in-depth newsletter covering all the highlevel principles of category design absolutely one of our most valuable newsletters ever and

then we made it free and pinned it to the top of our substack step number four you send paid Snippets to your entire free list all right so now we're starting to get into the weeds of execution here the one free one paid strategy is your Baseline if you can't consistently write one free and one paid newsletter on a specific topic attached to a traffic engine for months and ideally years on end nothing matters I can give you all the hacks and tips and strategies and techniques in the world it's not going to make a

difference you have to be consistent before you can be prolific but hey if you're still watching I'm just going to go ahead and assume that you're being consistent or you plan on being consistent right promise so the next thing you want to do to keep your paid newsletter base growing it's very simple on substack your free readers and paid readers are automatically segmented so if someone subscribes but doesn't buy they're on your free list and if someone subscribes and buys they're on your paid list and this is great because every time you hit publish you

can decide do I want this to be read by everyone so both free and paid readers do I want this to only go to the free list so you can pitch free Subs without pitching people who are already subscribed on the paid list or do you want this to only go to your paid list so you can give your paying subscribers maybe more content or access to something that you don't want your free list to get to follow up on the one free one paid strategy when we do this what we do is we send

one free post to everyone so free list and paid list but we actually do the same thing with our paid posts using a cool feature inside substat called the paywall preview so what you can do is you can choose where you insert the pay wall in the post which means you can make maybe the first 20% 30% even 50% of the post free to read by anyone and so what you do is you send the paid post to both your free list and your paid list which means you're paying subscribers they get the whole thing

that's why they're paying but the people on your free list only get to read in that preview section and this is amazing it's a it's a great way to soft sell and remind everyone on your free list hey by the way if you want to keep reading you upgrade to paid but this is only the beginning here's how you can take this to level 10 step number five you put the pay wall preview at a cliffhanger so most writers don't do this and it is causing them to leave so much money on the table it's

one thing to give free readers a preview of each paid post but it is a 100 times more effective if you can strategically put the pay wall somewhere they feel fomo because that's the real intention of a pay wall right when it's starting to get good or right when you're about to give the reader the thing if they get hit with a pay wall the likelihood that they decide eh you know what screw it and they just upgrade it goes up so you don't want to throw the pay wall preview just anywhere in your paid

newsletter what you want to do is you want to put it right before you give the reader the tangible thing that you're promising them because again the true value of your paid newsletter isn't really the writing it's the tangible asset that you were promising it's the chbt prompt it's the Kindle unlimited heat map it's the Russian literature annotation guide right so you actually want to give the explanation the free education away for free in the preview and then right as you say all right so here's your Kindle un limited heat map for the week that's

where you drop the preview pay wall and now the free subscriber has to make a choice they either abandon the newsletter right there right as it was starting to get good or they upgrade to paid step number six Leverage substack notes so lastly substack recently added this feature called notes which is basically Twitter SLX but on substack it's short form posts that you can make that get distributed in their notes feed and again this is just another way to get your writing in front of more readers so in addition to the one free one paid

strategy I would also just republish all your short form content on substack it's a very easy double dip so for example once per day we just take one of my tweets from X and repost it on substack and we've been getting a lot of really great traction substack also has this cool feature where it will show you how much money you've made turning free readers into paying subscribers from your notes so don't over complicate this one substack has a growing ecosystem and now it has an algorithm so republish your short form content on substack and

introduce more people to your writing that's it now whenever I explain how to write and scale a sixf figureure paid newsletter I always get a barrage of questions so here are some of the most common questions people ask in case you're sitting there wanting clarification on something or you have a faulty belief about how this won't work for your Niche Alina asks a couple really good questions so one how long should a newsletter be considering the short attention span all around of readers number two would you start charging immediately or give it away for free

first and three my worst nightmare about newsletters millions of unopened emails around the world my inbox is terrifying I now open one out of every 10 emails you know basically should you be worried about newsletters in general so three really good questions here so first I wouldn't think in terms of word count I would think in terms of giving the reader a tangible asset that is going to help them in some way if you can accomplish that in 400 words that might be all the reader needs whereas maybe you need 2,000 words in order to

really dig into that particular topic my perspective is word count is a horrible measure of value just focus on giving the reader something that actually helps them second question I would start charging immediately yeah I would just start with the one free one paid strategy you're going to learn very quickly whether or not you're giving people things that they would be willing to pay for and everything that you're trying to learn from free content should be happening on the social side anyway so you should be learning what things people value by writing on X or

writing on LinkedIn your newsletter is really just the doubling down of all of the things that you see working in your traffic engine and then third just this question around the newsletter category as a whole this is everyone's fear and it's really just a faulty belief uh it's a faulty belief to think you know there's a gazillion emails no one's going to read my email emails the people who need your content will read your emails and read everything from you and the people who don't need your content won't and that's just how the game works

Pedro asks you have 2,000 subscribers a 40% open rate and a 5% click-through rate but you want to improve the latter two metrics so what are the two things you would do this is a fun question so just to level set 40% open rate is pretty good the vast majority of newsletters fall in the 30% to 50% open rate range if you have below 30% you have a problem something's going on maybe you have deliverability issues or you just have a really cold list you're you're not keeping up with them frequently enough like you have

some sort of other issue if it's below 30% if you have an open rate above 50% you're crushing it so I don't think there's very much to worry about here with a 40ish per open rate and the lever for increasing the open rate is almost always just improving the subject lines and how you do that is make them more tangible right here's the asset you're going to get inside of this email for click-through rate that's not actually all that important of a metric what matters is the action the person is taking on the back end

of that click-through rate so are they buying a product are they filling out an application what what are they doing on the back of that click-through rate because it doesn't really matter how many people click what matters is if they click and then take the action that you want them to take but again if you want to improve the click-through rate same thing you just make it more tangible so don't just say click here to find out how to XYZ you know you make it tangible by promising something like click here to get your paid

newsletter checklist the more tangible it is the more the person is going to Value it the more they're going to click the more they're going to take an action Alexander asks how do you combat the diminishing returns experienced by long-term subscribers of a paid newsletter in other words what strategies do you use to continuously provide fresh high value content and keep your long-term audience engaged this is a good question but before I answer it I just want to point out most people who ask this question or ask a version of this question don't even have

a paid newsletter to begin with so they're trying to solve a problem they don't have yet right one free and one paid newsletter every week for 18 months and then worry about this but let's pretend you've already done that okay so if you've nailed the tangible promise of your paid newsletter you shouldn't have this problem when you subscribe to write with AI for example you don't just want one chat GPT prompt you don't want five you don't want 10 you want new chat GPT prompts as a writer forever and you're probably never going to stop

wanting chbt prompts or if you want to start self-publishing books on Amazon and playing the kind unlimited game you don't want one subcategory heat map you don't want five you don't want 10 you want a thousand of them and you want to keep getting them for years into the future so that you can keep your finger on the pulse that's why nailing the tangibility of your paid newsletter is so important because it's the asset it's the infinite collectibility of the asset that people want not just them reading your writing all of the newsletters that struggle

with churn problems take this approach of come read my writing and it takes so long to untrain that in your brain like people are not subscribing just to read your writing they want something in exchange and they want something tangible in exchange and ideally they want something tangible that they can keep getting new versions of over and over and over and over and over again into the future and two questions to wrap things up Mia asks can a woman in her 40s with no prior experience still thrive in this field and Arnav asks what topics

could a 16-year-old write about in his newsletter do I need prior experience in a particular field in order to write about it so this is a good question to end on and it's actually the same question just asked from two completely different Vantage points so just to level set here in these questions this is what every single beginner says at every age in every industry everyone in the beginning takes their experiences for granted even some of the most accomplished people in the world do this so quick story for you years ago when I first moved

to Los Angeles I met this really successful Tech entrepreneur an angel investor he had this massive like Iron Man style house up in the Hollywood Hills and he just sold his company for a gazillion dollars and anyway long story short I went to his house one day and we were just talking and he was telling me all these Frameworks he had for building Tech startups and I was just sitting there like mind blown because I'd never heard anyone articulate these kinds of ideas before and so I told him you know this is really incredible stuff

I think this would help a lot of other aspiring entrepreneurs have you considered writing about these things online and he looked at me just genuinely confused in his $6 million house overlooking the entire city of La and he goes why do you think this is valuable and I realized in that moment even the most successful people in the world take their knowledge for granted we all do because we're so familiar with what we know that we can't actually understand how or why that information would be valuable to someone else so to answer both of these

questions can you write as a woman in your 40s yes the mere fact that you're a woman in your 40s means you've had a ton of experiences that a lot of the world hasn't had and can you write as a 16-year-old of course you can you know more than all the 15-year-olds and the 14-year-olds depending on the subject matter you might even know more than the 19-year-olds or the 20-year olds the point is we all take the information we have for granted it's just the writers who make the most money have recognized that and take

it upon themselves to bundle it up organize it make it tangible and monetize it