Transcript for:
Building a Multi-Six-Figure Paid Newsletter

how do you build a paid newsletter how do you build a six figure paid newsletter how do you build a multi6 figure paid newsletter well I can tell you because I've done it twice I've built two paid newsletters to multiple six figures in recurring Revenue the first one was category Pirates this became a top five business paid newsletter on substack in less than a year and the second is right with AI our current paid newsletter uh category Pirates was a business that I started and then exited a year ago um our current paid newsletter is right with AI and in its first 18 months or so uh hit six figures and multiple six figures and very recently hit about 200 Grand a year in recurring Revenue so in this coffee with Cole what we're going to do is talk about what goes into building a paid newsletter specifically what are the differences between free and paid newsletters um the only two types of newsletters that I've seen that have the ability to go paid and my personal checklist this is something I've been refining over the past couple years for determining whether a newsletter has that subscription potential because not all topics lend themselves well to that specific business model um and then finally we're going to talk about how long you should give your paid newsletter before you decide you know does this have future potential or is this a bet that didn't pan out should I just cut the cord on it so the first thing I want to jam on which is very high level is the difference between free and paid newsletters so broadly speaking a free newsletter if if that is the the model that you want to go with you go I want to run a free newsletter and then how do I monetize that well that means you're either monetizing via ads or you're monetizing via digital products so for example there's a big vertical there's a big part of our business where this is the model so we have free newsletters on the digital writing side we have free newsletters on the ghost writing side and both of those free newsletters funnel people into to ship 30 for 30 or our premium ghost tring Academy and so really you can summarize the the model very simply it's you earn a bunch of trust I I mean you have to get people onto that email list right so it's right online get people to your free newsletter keep giving them more keep uh proving that you can help them and then keep nudging them and reminding them that you have another way to help them you have some sort of product you have a course you have a program and that's sort of digital product 101 the other way that you can monetize free newsletters which I am not a fan of uh is with sponsorships and with ads I know plenty of people who do it I know people who make great money doing it my personal belief though is if you can acquire the skill of building digital products why would you plug an affiliate greens you know or an affiliate greens affiliate code why would you do that when you could plug your own products and I I often find that the reason people fall into the model of having a free newsletter with ads is because that's one of the most popular models out there it's also very easy to understand um truthfully I think the root of that though the root faulty belief that people have is they for some reason think that it's better or easier to plug someone else's product than it is to build a product of your own so the same person who goes uh I'm afraid to be salesy I don't want to pitch my list is also the person who goes and by the way check out affiliate greens oh not affiliate greens it's a it's athletic greens why was I thinking it was affiliate greens athletic greens right so for whatever reason they think you might as well call it affiliate greens uh they think that there's something better or less salesy about plugging other people's products uh when in reality it's really the same thing and you should feel even better about plugging your own products right so that's the first big model and if you have a free newsletter and you know you want to start free and then you upgrade to paid that's sort of digital products 101 the next level though and it's a very different business model is having a paid newsletter and it's worth putting into context paid newsletters are a newer category so I remember 2018 I tried starting my first paid newsletter this was actually right before sub substack came out substack was really the company that pioneered the paid newsletter category and I remember I was trying to start a paid newsletter and there really weren't tools for it I had to duct tape together three four five different SAS tools and it sounds so silly to look back on you would have thought that there was technology for this a lot earlier but even in 2018 paid newsletters were not very common and so it really wasn't until substack came along and said you know what we're going to specialize in this type of business model and then as soon as they came out and they were venture-backed um raised a ton of money then you saw other platforms like convert kit go oh we also provide the functionality for paid newsletters um and then that's just sort of the natural progression you know as as one new category gets explored then other people Pile in and that's just how it works but paid newsletters as a business model are still pretty new and whenever there's a new business model that allows for a lot of freedom you know that the there's price Discovery like how much should you charge for your paid newsletter well it's it's a new category so there aren't really any rules people are figuring it out right um but what I've learned now growing two paid newsletters to multiple six figures in annual recurring revenue is that it is a very different type of product it's very very different than having a free newsletter that nudges people to some sort of course or digital product or program think free to paid right versus the newsletter being the product in and of itself okay and so the the way that I like to think about paid newsletters is actually don't think of it like a newsletter when you think of it like a newsletter your brain uh Associates it with all of the things that are part of a free newsletter and and actually that's not really true a paid newsletter is more like an evergreen book so what I mean by that is imagine you start reading a book on a topic and you love it so much it's so helpful it is exactly what you're looking for for this specific area of your life and then think about that feeling you feel when you finish the book and the book could could have been super comprehensive but you go oh I really wish they would have covered this a little bit more in depth or I wish they would have answered this question or you know what after reading it I have a followup like where do I go from here that is really the need that a p newsletter solves it's the ability to write a book quote unquote on a topic forever and when you can do that on a specific enough Topic in a helpful enough and tangible enough way what the person is really buying is they're buying for the book to never end I think that's the most helpful way of thinking about it and part of that and there there's a reason why platforms like subc have this sort of community element or or a comment section you know you can respond to the post and you can interact and you can get to know your readers right what is the ultimate purpose of that well the purpose is if you were going to write a book that never ended you would want to write with your readers right as they read a chapter quote unquote they would give you feedback they would give you ideas they would ask you questions and then in the next chapter you could answer them right and that's basically all a paid newsletter is and so understanding these two models right free to paid is the newsletter is really an attention asset a trust building asset that nudges people up to some sort of product right whereas a paid newsletter is the product the person is paying for the thing and so because there's those core differences the way that you go about these two things is very very different so for the sake of um what we're talking about today I'm not going to go down the free to paid rabbit hole we'll save that for another another cup of coffee um got my nice little ice coffee here today so today all we're going to talk about is the paid side what it means to have the newsletter be the product in and of itself okay so when you're thinking about a paid newsletter I think one of the biggest mistakes that people make is they think if I make my writing paid people will pay me for it and that couldn't be farther from the truth okay just because your newsletter is paid doesn't mean people will pay you for it all right and a stress test there's a reason why I evangelize all the things that I evangelize the stress test is if you can't get people to read your free stuff chances are they aren't going to pay for the paid stuff okay so you have to understand that as a business model the moment you say I'm starting a paid newsletter it is you you've moved beyond the the part of the relationship where you go you're going to read my writing like it's not it's beyond that now and now you are in a very clear value exchange and the problem gets compounded when the paid newsletter business model is is a subscription so what that means when someone is paying you per month or and usually with things like substack or other paid newsletter platforms you have a monthly option you have a yearly option well whether someone buys monthly or yearly what that really means is they are making the same purchase decision over and over and over again either every month or every year and when a customer has to make that purchase decision over and over again what that means for your writing is you go I BAS basically have to resell the value of my newsletter every time I write something so if you're sitting there and you go well that sounds really hard how do I do that okay from what I have learned and again i' I've written I mean not only have I grown two different newsletters to multiple six figures but I've just written so many pieces like this hundreds and hundreds and hundreds where I have gathered so much signal around what readers find valuable in the sense of not just did you enjoy this but you know open your wallet would you be willing to pay for this and would you be willing to pay for this over and over and over again and so there's two types of newsletters that I think have the the highest likelihood of being successful as paid newsletters and newsletters that don't fall into one or two of these categories as always there are always outliers uh there there will always be success stories that prove some of these Frameworks wrong but I would say broadly if you don't fall into one of these two categories you're going to struggle and and you could even say it differently and say the paid newsletter model probably isn't the best model to monetize what you're trying to write about okay so the first type of newsletter that has the potential to go paid is what I like to call researched curation so uh a good example of this would be uh like Trends the the the paid newsletter Trends um essentially what you're buying is you're buying someone else or a team of people to go research something about a specific topic they take the time to do that they develop expertise in doing that uh they develop pattern Rec recognition in doing that they uh you really like the conclusions they come to like it's one thing to research it but it's another like how do you interpret what you've researched right and so what you're really buying for 10 bucks a month 20 bucks a month 50 bucks a month whatever it is you're buying all of that effort so that's the value exchange the value exchange is hey you're going to go research this topic in depth you're going to come to these interesting conclusions and you're going to give it to me and you're going to do that every week or every other week or every month and I'm going to give you 20 bucks and that's the value exchange and so high level when you're thinking about paid newsletters it's actually important as a writer to remind yourself that think about it like am I a good writer yes or no that's not really the value exchange you could be a really terrible writer but if you uh if you deliver on that value exchange then the quality of the writing actually comes second or third or fourth or fifth or 10th it doesn't really matter the thing that matters is Are you delivering on it okay and one side of the extreme right one of these categories that tends to do very well for for paid newsletters is when the thing the reader is buying is basically uh leveraged labor or time and effort they're like I'm going to give you 20 bucks a month and you're going to go research this thing for me okay and then depending on the thing that you're researching right and how it's price anchored depends on what you can get away with charging right so it's one thing if you go I'm going to go research uh I don't know like a agriculture or industrial farming you know uh versus I'm GNA go research startup Trends and I'm going to help give you business ideas and business models right so depending on what you're researching sort of changes who your target reader is and maybe what their threshold is for what they'd be willing to pay so re researched curation is one type of paid newsletter on the other side of the spectrum the other type of paid newsletter and this is uh the two paid newsletters that I've built have both been in this bucket but I've seen a lot of people find success in the researched curation side but the other extreme is what I call original thinking so in this paid newsletter what the reader is really buying what the value exchange is is they are buying uh insights behind the scenes insights and Industry expertise at scale essentially so think about you get interested in a topic you want to accelerate your pattern recognition for that topic you want to accelerate your growth curve you want to pick the brain of some really smart person um that person probably isn't selling their time you probably can't get them to hop on a cup of you know a zoom and grab a digital cup of coffee with you right and if you could it might be really really expensive so a way that that type of Creator can get around that problem and a way that that type of consumer can get access to that person's brain is by having an original thinking paid newsletter which essentially means these are all the things that I would tell you if if we were in person I'm just going to give you access to all of the things I've learned behind a pay wall and again depending on what you price anchor to and depending on how you help that Target reader solve a problem unlock a specific outcome whatever it is then that is what affects how much you can charge and I have found that if you aren't in one of these two categories researched curation or original thinking it's very hard for a paid newsletter to work and what happens unfortunately is most people who start paid newsletters don't do either of these they do this weird Middle Ground where they go subscribe to my writing okay nobody cares about your writing nobody cares about my writing the only reason that people pay for my writing is because I make it very clear this is what you want this is what you value I will deliver on that value exchange and in return here's how much it costs okay but when you walk up to the market and you go I'm special I believe that I'm a talented writer I took all this time to write this thing and other people deserve to give me their time energy attention and money of course it's not going to work and yet that's where everyone starts because I think I blame everything on you know the traditional education system but you know we all sort of grow up in this world thinking that we are what's special that we are what's important you know and the whole idea of building a personal brand compounds this where people are like oh people want to follow me no nobody wants to follow you what they want to follow and what they what they want more of is content within a specific topic helping uh helping them solve a specific problem helping them unlock a specific outcome so it has very little to do with you and how much you love your own writing and it has everything to do with who you are helping and how you can help them in their life solve problems unlock outcomes whatever it is now of course whenever I explain this there are always outliers there's always the random person for whatever reason they have just this really unique writing voice and they defy all these rules and people find them super entertaining or thought-provoking or whatever and like they break the framework but that person is successful and I think it's really important whenever you're studying something and I don't I don't just say this for what we're talking about here I mean whatever you want to get interested in in life it's really important to Sure find motivation inspiration uh find what lessons you can extract from the outliers but remind yourself that it's not a great strategy to look at someone who won the lottery and asked for financial advice right so outliers are usually not great examples of well you know show me the pattern what's something that I can replicate and there's a reason why you know I take the time to share a lot of these learnings and a lot of these things that uh I've experienced because a I don't think I'm an outlier but B I've monetized my writing in so many different ways at this point that I know it wasn't a lottery outcome you know like I two different paid newsletters to six figures multiple online course programs to multiple millions of dollars in Revenue um I've done Services I monetized ghost writing with an agency I've done SAS we have type share um I've self-published 10 books I've done multiple six figures publishing books so I've monetized my writing in just about every way possible and so I know that it wasn't you know just I woke up one morning I closed my eyes I took a swing and I hit a home run and W bam like that that isn't what happened and so I can extract these Frameworks and and better understand like what were the patterns that led to these types of outcomes and that's my goal here is I want to I want to share with you so if you're thinking of starting a paid newsletter it needs to be in one of those two categories it needs to be researched curation or it needs to be original thinking if you are an expert in an industry and you have an extreme information Advantage I would encourage you to do original thinking if you aren't an expert in an industry or you don't feel like you have a ton of pattern recognition or Frameworks to share with people and that you can monetize I would encourage you to go the researched curation route and you can always go back and forth like the it's not one size fits all but that's generally how I would think about it okay which sort of takes us into what are the criteria that I look for uh when thinking about this type of business and business model um I'm sure I will start other paid newsletters in the future I think it's an amazing business when you can get it right um it's very high margin it's something that you it it is an infinite game you know like when you find a topic that you really really enjoy writing about and you understand the value exchange and you can deliver on that value exchange for readers very very well uh this is one of the best business models that you could have as a writer and it's very foundational I like thinking of a paid newsletter as this mini engine that gives you subscription Revenue um it allows you to write with readers and really get to know them that subscription Revenue can sort of fund the next thing that you want to build maybe on top of it it's an amazing nucleus to have in the middle of your ecosystem but it is a little bit harder and it's definitely harder for the brand new beginner I've never written anything before on the internet I would not encourage you to start with a PID newsletter I think it is a great business model that is better served a bit later much easier to just start for free and and evolve from there but let's say you're sitting there you've been writing online for six to 12 months uh you've clarified a niche or at least the direction of a niche you've started building an audience you've started building trust you've been writing with people you've gathered some feedback you understand what questions people are asking right you've done a lot of that upfront work and you go I'm thinking about starting a paid newsletter okay well these are the four criteria that I think about when I'm stress testing myself you know would this topic uh be be a good one for the paid newsletter model so the first one is your paid newsletter has to be infinitely repeatable so what I mean by this and this is where it helps to think categorically when a reader is subscribing to your paid newsletter again think of it like a book that never ends so you want to frame your paid newsletter and you want to pick a topic that is something that you could write about forever and so if you're doing a researched curation paid newsletter you want to think what is something that I could research and curate forever right I will never run out of things and I'm going to give you an example of of an idea I had for a paid newsletter that uh didn't meet this criteria and I it took me a while to realize why it wouldn't work and I I'll talk through that and then the other side is if you have an original thinking newsletter you want to frame it around a topic where it's an infinite game for yourself you're like I'm I'm passionate about this and I will never stop being passionate about it I want to write about it forever I want to think about it forever and even if it's not quote unquote forever right you can have a paid newsletter for five years and decide you're done with it but you want that framework you want to start from a place of what what is infinitely repeatable so I'll give you a a quick example couple years ago I came up with the idea of wanting to do a paid newsletter around uh like in the world of self publishing I thought it would be really interesting and this was sort of something that I was thinking I might want as a consumer as well it' be really interesting to have a paid newsletter where uh researched curation you're constantly sharing like what are the cuttingedge things that are happening in self-publishing and the model that I was using in my head is I was saying well this exists in the world of Finance right I mean Financial paid newsletters were the ones that originally pioneered this category you know you go look at a company like uh Agora Agora is the largest paid newsletter portfolio in the world essentially it's a billion dollar company that's a combination of paid newsletters and digital products and and online courses but its engine is really paid newsletters and financial paid newsletters have always been sort of the core of this category because if you're you know trying to make money and you want stock tips that is an infinite topic you're never going to wake up the next morning and go I don't want to know what the next hot stock is right and so I was thinking oh well that works in finance maybe that'll work in one of my subcategories you know maybe that'll work in self-publishing and it wasn't until I started getting into it and exploring the idea that I started to realize that self-publishing as a category and as an industry doesn't move that quickly you know it's not like Amazon's updating its ebook algorithms every 24 hours right A lot of the things that are changing in that industry happened over 6 months or 12 months or two years or 5 years and as I started to explore it I realized this actually isn't as quickly as I would need it to this isn't an infinitely repeatable topic I think it's something I could write about every 6 months right but it's not something like stocks that are changing minute to minute and so that's the sort of questioning you want to go through is is this an infinitely repeatable topic and if it's researched curation how quickly can I deliver on that value exchange for readers right how often can I present new information is it something where there's always something new happening right there's a reason like Finance there's always new stocks politics there's always some new law or drama or conflict or right those the reason that those Industries tend to work well for research curation is because there is always something new happening basically every minute and so that's one of the components that you're looking for on the original thinking side you also want to pick a topic that you would feel comfortable and you would be excited to write about infinitely because you don't want to say you know go I'm going to start writing about this thing and you go I have three things to say about that and then I'm done well that isn't infinitely repeatable you're you're going to run out of things to say right so that's criteria number one criteria number two is that again there are outliers that prove this wrong but I would say as a rule it's a very very helpful place to start your thinking is your paid newsletter has to provide readers with something tangible and not intangible so one of the mistakes that I see uh that holds a lot of paid newsletters back is people go you know you can read about X topic they're sort of just promising like the writing generally but if you look at the most successful paid newsletters almost all of them in some way promise some sort of tangible benefit or tangible asset so what I mean by that is in the world of financial newsletters for example you will see it's very common for people to go and in every newsletter we give you a new report well what is a report a report is a tangible asset it is it is essentially an object in the digital world right or something that we used when when this clicked for me this is why I was so excited to start our right with AIP paid newsletter is we say in every issue we explain a framework and then we give you an AI prompt what is a prompt a prompt is a tangible asset you can feel the prompt you can hold the prompt you can copy paste The Prompt into chbt or Claude right um we did this again with type share what's the value exchange of types share well when you subscribe type share is basically SAS is really just just an advanced version of a paid newsletter side note but what we did with type share the value exchange is we will give you templates what are templates templates are tangible objects in the digital world right or you see this with really uh well researched paid newsletters every issue we will give you an in-depth case study right what is a case study is a tangible asset so as often as possible I think one of the most important criteria is how do you make your newsletter tangible because as a general rule of thumb in the digital world and especially in the world of info and education uh we like to refer to it as digital air and so when someone is buying digital air the whole game is how do you make the air feel as tangible as possible how do you how do you make the air feel like an object or said most specifically how do you make digital air feel like an analog object and the way that you do that is you find a way where in each issue you are associating the writing with some sort of tangible object template case study prompt report what blueprint like something that feels tangible third criteria is as much as possible you want your paid newsletter to have an objective outcome versus a subjective outcome so this is a copyrighting technique that I've really been clarifying and letting crystalize over the past year which is most people speak in subjective outcomes so a subjective outcome is if you say something like like this paid newsletter will help you uh Master productivity well if you ask 10 different people hey what is your uh interpretation of the phrase Master productivity what would that mean to you you will get 10 different answers and the reason you get 10 different answers is because it is a subjective outcome there's nothing specific and objective about it and what happens is when you speak in subjective outcomes you are essentially killing word of mouth because you are adding subjectivity to the conversation you are leaving room for interpretation and when you leave room for interpretation each individual person has to come to their own conclusion of what that means and when each individual person has to come to their own conclusion of what that means each person will come to a different conclusion and when each person comes to a different conclusion guess what they are all going to talk about your paid newsletter in a different way and when everyone talks about it in a different way that is the opposite of Word of Mouth right so you have to really follow that logic line all the way down the key is when you can find a way to speak in objective outcomes so a very easy one using this example would be instead of saying I will help you master productivity it would say I give you the you know tools systems and automations to uh so that you can go from uh project manager to VP of operations okay that's a very objective outcome and it's objective because you either got promoted to VP of operations or you didn't and so when you speak in an objective out when you speak in objective outcomes you ask 10 different people hey what's your interpretation of that they will all mirror that back to you and when 10 people all mirror the same message back to you guess what now Word of Mouth can accelerate because now you have everyone saying the same thing and so I would say by far this sort of thinking is the hardest component for people and you have to sort of if you're sitting there and you go that sounds really hard well first of all I always like to preface um okay so did you expect that having a 99% margin business that allowed you to work from your sweatpants from anywhere in the world and have people see you as an authority would just be easy right like everyone wants these unbelievable outcomes and then the moment they're confronted with even a little bit of friction they're like I don't get it I thought this was I just smash my keyboard and money rains from this guy right so yes your brain should hurt a little and yes you should sit there and go I I don't know if I quite get it yet but let me let me keep pushing let me keep pushing because once you understand these skills like now that I understand how to do this I will continue building successful paid newsletters and I will continue building successful products because I know objective outcomes are more beneficial than subjective outcomes just like speaking in tangibles is more valuable than speaking in intangibles right so you have to look at this through a lens of skill building not as hey Cole can you just give me the answer and then I'm done right and then the fourth this is another one that takes some time to sit with the fourth criteria is that your paid newsletter has to be price anchored to some sort of upside it has to be price anchored to either you have an existing problem I will help you solve that problem when I help you solve that problem you will save x amount of money or stop losing x amount of money um or it could be something that's more tangental like it could be tied to happiness fulfillment things that are intangible but you have to find a way to make those intangibles feel tangible right so it's not just like I will help you not feel unfu or help you feel less unfulfilled it's like hey when you're unfulfilled that leads to XYZ which causes one two three and all of that we could napkin math into is probably costing you amount of money per year right so you have to find a way to price anchor to either the downside or ideally the upside when you acquire these skills that is what separates someone here from someone over there once you acquire these skills earning potential can go up people who have these skills tend to make 2x more than the person who doesn't have this type of skill right and so if you don't price anchor your paid newsletter what happens is you essentially fall into the the Trap of going hey read my writing for 20 bucks a month and that's not what the reader's interested in the reader is not interested in paying you $20 a month to read your writing the reader is selfish the reader cares about themselves the reader wants to know how you can help them and the reader wants to know what is the value of them being helped how much better would their life be and whenever I explain this the the objection that sort of pops up from people is they go well I don't know I don't know the exact answer I don't know exactly how much money they make I don't know how much more money they would make I'm afraid of making a promise that that maybe isn't real that's fine all of these are guesses anyway but you can napkin math it you know like I remember I we had a situation like this I was doing a live Workshop maybe a year ago and the example still sticks in my mind but was asking they said um I write about uh like doing at home yoga routines I don't really understand how to price anchor doing atome yoga routines and and they were so in the space of you know yoga is about being happier and being more flexible and enjoying your life and being more present like all of these things are so intangible I don't understand how to price anchor it and I go okay well let's let's go inside the mind of a potential customer I am a potential customer um I sit all day I have low back problems because I sit all day um I enjoy going to yoga all of these things are true this is actually me um I enjoy going to yoga the problem is I really struggle to get there and so what happens is you know I I can't tell you for how many months I've paid for a yoga membership uh 10 minutes away and I keep telling myself that I'm going to get there but I'm just so busy with work and I I really struggle uh to make it happen I'm lucky if I get there on a Saturday that's about it but I know that yoga would help me a lot um and it would probably help my lower back issues and it would probably make me happier how do you price anchor to someone like that well it's actually very easy napkin math if you were talking to me you would go hey Cole you're a busy entrepreneur you probably sit at your desk all day right you might even have some low back and hip problems as a result of it and you might have been paying for a yoga membership for the past year and you feel guilty because you're not using it and you really wish you could go but you just can't get there for maybe more than once or twice a month and so if you think about it the cost of your yoga membership you know say it's a 100 bucks a month and you barely get there one or two times a month that means each time you go to yoga cost you 50 bucks or if you want my paid newsletter is only $10 a month that's that's a tenth of the price of your uh yoga membership but I will give you routines that you can do at home and not only will I give you routines that you can do at home but I actually understand that you're a really bus busy entrepreneur and so the routines that I specialize in are really quick bite-size 15minute yoga routines and actually one of the things I recommend is using your desk chair to get some of to do some of these stabilization exercises so that way when you go back to sitting all day your low back won't hurt as much so you could either keep paying a 100 bucks a month for the yoga studio that you never go to or you could pay $10 a month and I'll give you everything you need and then you'll actually get the yoga routines done because like I said they're bite siiz you can get them done in 15 minutes that is the whole game and the only reason that I'm able to articulate that is because I have gone through that same script or that same exercise over and over and over again in a hundred different Industries and so anytime someone says I don't think that my topic can be price anchored just means they haven't built the skill yet it does not mean this doesn't work for your industry it does not mean oh people in your Niche don't want that or or uh they'll be turned off by that no they won't no they won't you might not even be interested in yoga and just listening to me articulate you're probably like oh that makes a lot of sense I probably need that too right so all of these are faulty beliefs and so when I'm thinking about what sort of paid newsletter to build these are the different criteria that I'm looking for let's just recap them one more time paid newsletter has to be infinitely repeatable paid newsletter has to be tangible versus intangible you want to find ways to promise tangible Assets in the digital world your paid newsletter has to be objective in terms of the outcomes that it helps people unlock the more subjective the outcomes the worse it's going to perform I'm telling you right now and then number four your paid newsletter has to be price anchored to some sort of upside or helping the person mitigate some sort of downside if your paid newsletter can't check all four of those boxes there's a very high likelihood that you are falling into the Trap of I just want people to read my writing and pay me for it and I think this is one of the hardest things for newer writers to really wrap their heads around is it's almost like you have to go through this whole unlearning process and then sort of retrain your brain to not start from a place of I wrote it other people should care about it you have to do the inverse you should go what do people care about I'm going to go write that and that I mean if I look back on my own writing career I think that was the thing that took me the longest to learn okay last quick thing how long should you give your newsletter general rule of thumb I would give it about 6 months I think in 6 months you will get a good signal as to whether or not there's real potential here um category Pirates was trending toward six figures in the first six months it wasn't quite there yet but it you could see oh we give this a little more time and it's going to get there right with AI was the exact same thing within 6 months we hadn't hit six figures yet but the the trend line was yep if we just keep going it's it's going to get there um inversely if you spend 6 months and your paid newsletters only doing like a couple hundred bucks a month it's one of two problems either you don't have a traffic engine so you've started a paid newsletter prematurely you're not writing on social platforms you don't have a way of bringing people from free to paid or you haven't checked off the criteria that we talked about here so and and I see it all the time I see people who have amazing traffic engines and then they start a paid newsletter and it just doesn't take and it is almost always because some part of those four criteria isn't happening so I would really really encourage you you know make sure that you're going through and stress testing these different things uh don't give it two weeks and then call it don't give it a month and then call it don't even give it three months and then call it I would give it a full six months be very consistent treat it like a true business and then come to your conclusion and by the way I've done this I've launched other paid newsletters gave it six months and went e you know this really isn't trending the way I thought it was let's kill it that that bet isn't panning out and that's just part of the game some sometimes they take off sometimes they don't but you want to make sure that you're giving it a real shot um otherwise it's it's it's not a great science experiment right if you want to run a clean science experiment you want to have as many healthy variables as possible the last thing I want to cover and this is way more advanced but this I I want to plant the seed and then you know maybe it'll bloom for for you in a couple years when I was building category Pirates um we developed a really interesting publishing model and I am now doing it again I'm going to replicate it for myself but I want to share it because I've never seen anyone do it and I I think that more people with paid newsletters would make a lot more money if they did this so the model that we really pioneered with category Pirates was category started as a paid newsletter that paid newsletter was 20 bucks a month 200 bucks for the year and we aimed to do one very very long form piece it was five to 8,000 words very long form original thinking uh every week for a while that that got to be a lot so then we moved to an every other week Cadence and we realized that because the pieces were so long and so in-depth like most people couldn't read it in a week anyway so we we could bring down the volume a little bit and after about 6 to 8 months of doing that I started to realized that there was so much value in these long form paid newsletters that it was almost like people were missing it because there was so much packed in there and we we would have people read and send us positive comments and obviously people were getting a lot out of it but it sort of started to occur to me our archive was getting bigger and bigger and all of these valuable pieces were like buried in the the archive and a lot of times you don't always go back through the archive and decide to read everything especially if you're a new customer and so I realized that there was this opportunity where you know we we would write about these similar topics you would see these like a through line like different paid newsletters would fall into different buckets and after about 6 to 12 months if you strung a lot of those newsletters together you essentially had a book and so what we did is we basically had the paid newsletter fund our self-publishing Empire and so what that looked like is we would pick over time this became more conscious in the beginning we did it accidentally and then we sort of dialed this in over time but as we got going what this looked like is we would pick an overarching topic we would go we're going to write about this topic for the next six months 8 months 12 months and then at the end we're going to take all the pieces on that topic we're going to do a little light editing and we're going to smash it together into a book and so if you look up category Pirates books the first one we did was the category design toolkit second one we did was a beginner's guide uh to marketing or to category design um and then the third book was Snow Leopard and all three of those books are essentially a bunch of paid newsletters smashed together with a little bit of editing cuz there were some things that like didn't make sense uh out of the context of the paid newsletter so I had to go back and just refine a couple things um edited for a book and then put up for sale on Amazon and what that allowed us to do was monetize the content a second time so not only did category Pirates become a multi- six figure paid newsletter in and of itself but then we also double monetized it with print books with ebooks and eventually later with audio books and then the self-publishing side of the business also grew to multiple six figures and I see so many writers that have this opportunity right under their nose and they just don't do it and they don't do it either because of some faulty belief they think the reader not going to want it twice which we found was the complete opposite people who loved our paid newsletter wanted a print copy on their desk right so okay that belief doesn't exist um or they just didn't want to go through the work or they or they misunderstand how easy self-publishing is and just to give you a quick little crash course on that all you have to do is create a KDP account with your Amazon account and you format there's a great tool for formatting the ebook um called Rey re DS y.com you can load all the text into it it'll export it as a file that you can upload uh to Kindle and then you get a cover designed and then if you want to do print you know I would go find someone who wants to format it for print um you're looking at upfront cost of maybe a thousand bucks I mean if you have a successful paid newsletter that's no problem right that's what I meant at the beginning where your paid newsletter can fund some of these other problem or some of these other projects maybe if you want to make it look super great like snow leopard as a project looks so great that probably cost us all in four or five grand okay so you spend four or five grand you double monetize your work and you know snow leopard went on to make tens of thousands of dollars as a self-published book probably more at this point it's probably across 100K at this point so I share that as whether you go the paid newsletter route whether you go the free newsletter route whether you're just writing a ton of content online this is probably a topic for another coffee with Cole but uh I would really really encourage you to explore the self-publishing side of things because the the self-publishing aspect is so much easier than people realize it costs you you don't have to buy any inventory up front it's all print on demand when you put something up for am on sale for Amazon when someone buys the art and business of online writing for example doesn't cost me anything Amazon prints it on demand for you extracts the printing cost and then gives me the royalty and that's how easy it is and a lot of people don't realize that you can do that with all of the content you're creating in your newsletter and a especially if you have a paid newsletter and even more especially if you have an original thinking paid newsletter because you're already taking the time to essentially write a never-ending book so if you're taking the time to write a never-ending book why wouldn't you just do the incremental effort smash it together into a book and double monetize it so I hope you enjoyed this episode of coffee with Cole um I am a a big big believer in paid News letters I think they're a super cool business model I also think that they are one of the hardest so whenever I see a beginner say I'm going to jump right in and start a PID newsletter I discourage them from doing that I don't think that it's the business model to start with I think you are way way better off uh starting with a free newsletter and then upsell nudging people to like a tier one online course or a cohort-based course or even something even simpler like one-on-one coaching like just dip your foot in the in the water of monetizing uh but then as time goes on as you refine Frameworks as you clarify your niche as you understand your information Advantage there is a place where in your portfolio that's the way I I think eventually that's where you want to get to in your portfolio as a digital writer having some sort of paid newsletter um having that forcing function to basically write a book in public write multiple books in public um having that benefit of subscription Revenue that can fund you know oh now I can put a book out that looks like a traditional self or a traditionally published book but I can do it self-published I can own all of it right having the paid newsletter as the nucleus of your portfolio is very very powerful and so there's a reason why um we've done it we've done it with right with AI I plan on doing it more I have a personal paid newsletter now called the art and business of writing um and I'm going to do the same you're going to watch me do the exact same thing like six to 12 months from now you're going to see me publish a book that book is going to be the culmination of a bunch of things that I wrote as paid newsletters under the art and business of writing I'm I'm going I'm doing it so if you want to see how this works feel free to just follow along and you know you will you will watch me practice in in public but um I just wanted to share that as a model because I think it's super interesting so um let me know I the response from the first one on this was really really great I appreciated all the comments thank you everyone uh thanks for those who said the studio didn't sound too bad um I'm getting it all soundproofed next week which will be very very exciting I'm excited to get some panels and stuff in here um and also I am I'm serious if you have any specific questions or specific things that you want me to dig into please let me know um when I sit down to record these the first thing that I do is I pull up the comment section of the most recent one and go what questions did people ask so um if you have any ideas or anything that I could be helpful on like I said this is my way of getting coffee at scale so the same way if we were going to sit down for coffee and you were going to pick my brain um I really want you to get that benefit here so leave comments ask me questions uh happy to share and I'll see you in the next episode