How to Start and Sell a Paid Newsletter That Works

Summary

Coffee With Cole: The Digital Writing Podcast

Episode: How to Start and Sell a Paid Newsletter That Works
Host: Nicolas Cole
Release Date: March 18, 2025

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Introduction

In this enlightening episode of "Coffee With Cole," host Nicolas Cole delves into the intricacies of launching and monetizing a paid newsletter. With a focus on balancing free and premium content, Cole provides actionable strategies for aspiring digital writers and entrepreneurs looking to establish a sustainable paid newsletter model. Guest Sebastian joins the conversation to explore practical steps and real-world applications of these strategies.

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Understanding the Paid Newsletter Model

Timestamp [00:00 - 05:14]

Cole begins by addressing a fundamental question: "When starting a paid newsletter, what is the best strategy?" He suggests a dual-newsletter approach where creators send out one free newsletter alongside one paid newsletter each week. The free version serves as a teaser, encouraging readers to subscribe to the premium content.

• Key Point: The dual approach acts as a funnel, introducing the audience to the quality of content available in the paid version.

Notable Quote:
Cole states, "The free newsletter basically acts as a reminder that you should buy the paid newsletter." ([00:00])

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Managing Subscriber Churn

Timestamp [00:46 - 05:14]

Sebastian raises a concern about potential churn, questioning whether offering different content tiers might lead to losing free subscribers. Cole acknowledges that some churn is inevitable but reframes it as a natural part of monetization.

• Key Point: Monetization often involves "weeding out" those who are unwilling to pay, thereby refining the subscriber base to those genuinely interested.

Notable Quote:
Cole explains, "Whenever you start to monetize anything, it fundamentally means you're starting to weed people out. There's the people that were never going to buy, and then there's the people that always were going to buy." ([02:10])

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Differentiating Free and Paid Content

Timestamp [05:14 - 09:10]

The conversation shifts to the nature of content that retains free subscribers versus what compels readers to pay. Cole emphasizes that while free content often provides general value, paid content must offer deeper insights, personal experiences, or strong opinions to justify the cost.

• Key Point: Successful paid newsletters typically offer unique perspectives, in-depth analysis, or entertaining personalities that resonate on a personal level with subscribers.

Notable Quotes:
Cole remarks, "What people pay for is personal experience, very strong personal opinion, personal entertainment." ([06:30])
He further illustrates with Morning Brew's model: "Morning Brew was like, you want to know what's going on in the business world... and they monetize with ads." ([04:50])

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Building a Sustainable Paid Newsletter

Timestamp [09:32 - 11:16]

Cole advises starting with a low-commitment product, such as an ebook or webinar, to gauge interest before committing to a recurring paid newsletter. This approach allows creators to gather valuable data and understand their audience's preferences without the immediate pressure of sustaining a subscription model.

• Key Point: Testing the market with standalone products can provide insights and reduce the risk associated with recurring revenue models.

Notable Quote:
Cole suggests, "The fastest way to figure that out that I've learned is like, start with a standalone and then if something works, then you duplicate." ([07:45])

Sebastian reflects on this strategy, recognizing the value in "adding an extra step where rather than jumping straight from free to paid, you're selling a one-off thing first." ([05:37])

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Case Study: George Saunders’ Approach

Timestamp [07:30 - 08:05]

Cole cites George Saunders, an American author, as an exemplary model of transitioning from a bestselling book to a successful paid newsletter. Saunders turned his book into a weekly paid newsletter that continues to engage his audience by building upon the book’s foundation.

• Key Point: Replicating successful content formats in a recurring model can sustain and even amplify audience engagement over time.

Notable Quote:
Cole describes the paid newsletter as, "a book that's just to succinctly put it, a paid newsletter is a book that never ends." ([07:55])

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Tailoring Content for Specific Audiences

Timestamp [08:15 - 09:10]

Customization is crucial. Cole recommends tailoring paid newsletters to specific industries or reader demographics to enhance relevance and value. For instance, a newsletter could focus on new regulations impacting particular business sectors, providing detailed analyses and actionable insights.

• Key Point: Specialized content addresses niche interests, making the newsletter more indispensable to its subscribers.

Notable Quote:
Cole advises, "An easy example would be, here are all of the new regulations that are happening and here's how they're specifically going to impact like these business sectors." ([08:15])

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Balancing B2C and B2B Approaches

Timestamp [09:10 - 10:26]

Sebastian questions whether targeting a broad consumer base (B2C), particularly those interested in politics, is a viable strategy compared to more specialized niches. Cole reiterates that both approaches have their own set of challenges and encourages creators to focus on the problems they are willing to solve.

• Key Point: Whether choosing B2C or B2B, understanding and addressing specific audience needs is paramount for the success of a paid newsletter.

Notable Quote:
Cole remarks, "Unless it's super, super in depth investigative journalism, that is not what people pay for." ([04:15])

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Final Recommendations and Insights

Timestamp [10:52 - 11:16]

In concluding the discussion, Cole emphasizes the importance of experimentation in monetization strategies. He encourages creators to actively try selling products to uncover what resonates with their audience, as this hands-on approach offers the most direct insights.

• Key Point: Practical experimentation and iterative learning are critical to discovering effective monetization methods for paid newsletters.

Notable Quote:
Cole states, "The only way to learn how to monetize in this way is you just have to try because it's like nothing will teach you more about how to monetize the specific person that you're talking to or who's reading your work than trying to sell them something." ([10:52])

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Conclusion

Nicolas Cole's episode on "How to Start and Sell a Paid Newsletter That Works" provides a comprehensive roadmap for aspiring digital writers. By balancing free and paid content, understanding audience dynamics, and employing strategic experimentation, creators can build sustainable and engaging paid newsletters. Cole’s insights, enriched by real-world examples and practical advice, make this episode a valuable resource for anyone looking to monetize their writing effectively.

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Key Takeaways

1. Dual-Newsletter Strategy: Combine free and paid newsletters to attract and convert subscribers.
2. Embrace Churn: Recognize that some subscriber loss is natural and focus on retaining those who see value in the paid content.
3. Differentiate Content: Offer unique, in-depth, or personality-driven content in paid newsletters to justify the cost.
4. Start with Standalone Products: Test the market with one-off products before committing to recurring subscriptions.
5. Customize for Niche Audiences: Tailor content to specific demographics or industries to enhance relevance and value.
6. Experiment and Iterate: Continuously test different monetization strategies to find what works best for your audience.

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By implementing these strategies, podcast listeners can embark on their journey to creating successful and profitable paid newsletters, fostering deeper connections with their audience while generating sustainable income.

Transcript

[Cole]

Going to recap the question first to make sure I understand and everyone here understands. So the question as I understand it is when starting a paid newsletter, the best strategy. This is what I recommend is each week you, you send one free newsletter and one paid newsletter. The free newsletter basically acts as a reminder that you should buy the paid newsletter. Okay. That, that is the, the overall strategy. The question is, can one newsletter, we'll say the free one, speak to a potentially quote, unquote different or broader audience than the specific paid newsletter? Does that work together? What are the impacts of that? Is that. Did I get the question right?

[Sebastian]

Yeah, that's pretty much it. Yeah.

[Cole]

Okay, so I'm going to start with some of these last things that you said and then I'm going to kind of talk bigger picture because this is actually a really important point and I don't want to, I don't want to spend too much time on this topic, but it's worth digging into. So first of all, will this lead to potentially increased churn of free subscribers? Yes, but that is not necessarily a bad thing. Okay, so whenever you're trying to monetize anything, paid newsletter is just a different type of vehicle. We could be talking about an ebook with. Could be talk. We could talk about. Insert whatever business model you want. Whenever you start to monetize anything, it fundamentally means you're starting to weed people out. There's the people that were never going to buy, and then there's the people that always were going to buy. And now you're monetizing. Right. So just because you experience some churn doesn't mean that that's a bad thing. The second is often times, there is oftentimes the thing that makes something compelling when it's free is not necessarily the same thing that makes it compelling when it's paid. So let me, let me explain what that means. The things that we look for as readers out of free content tend to be different. News is a really good example of this. We all sort of just expect the news to be free at this point because the news is free everywhere. Right. So in many ways making your free email the. Here are the things that are happening very bipartisan. Let me just explain like factually, like what this means from a, from a literal perspective. That's valuable. But it, I think that it would be hard to monetize that because you're basically taking free knowledge and just simplifying it. A different version of that is this is what Morning Brew did. Morning Brew was like, you want to know what's going on in the business world. But reading the finance section of the newspaper is a little confusing. Why don't we just explain it in millennial speak? And this is what they did in the 2010s. So that concept. And it's a free newsletter, they monetize with ads. So that's not necessarily like a novel thing. And that's fine. What people pay for is not news. This, this is what's really, really important. Unless it's super, super in depth investigative journalism, that is not what people pay for. What people pay for is personal experience, very strong personal opinion, personal entertainment. There has to be some sort of personal or personality that you want to buy into. That could be. That could show up in a lot of different ways. That could show up in very extreme opinions. That could show up in. I love the way that you talk about these topics. It's hilarious. That's really what someone's buying. And if you want a great example of this, the New York Times is a paid newsletter like that. If you go to the New York Times, the New York Times is one giant paid newsletter. Some content is free and some content is paid. The New York Times has trouble getting people to subscribe for more than a dollar a month. And that's because it's like they're trying to monetize this thing that has become so commoditized and free. So I just want to explain that so you understand sort of like what is the game that you're playing, in my opinion. And this is for you, and this is for everyone here. Paid newsletters are amazing vehicles, but they are one of the hardest. They, they are one of the hardest because you have to recognize that you are reselling the customer every single month like it is. It's a very different thing. So if you haven't started a paid newsletter yet, Sebastian, or even if this is early, what I would consider, this would be my recommendation for everyone. If you want to explore something like this, I think it is much easier to start with a free list and then try selling them one thing. Can you sell them an ebook? Can you sell them a paid webinar? Can you sell them a small group coaching roundtable? Can you. Can you sell them something so that you can get some sort of data around what they want? The paid newsletter should be then sort of the amplification of what you learn that they want. Does that make sense?

[Sebastian]

Yeah. So at the moment, my thinking is I'm posting on Twitter every day. I'm getting signals on what I think people want. I Should build a paid product around it. But what you're saying is add in an extra step where rather than jumping straight from free to paid, you're saying, would you pay for this one off thing? And then you get even more signal from that. And then you build a. If it works, you build something else around that, and you've let it around that.

[Cole]

Yes. Yeah. It's kind of no different than if someone was like, hey, Cole, I want to start a SaaS platform. I would be like, don't go build a SaaS platform. Go build a tool. Like, a single tool. And can you get people to buy it for 29 bucks? Can you get people to buy it for 100 bucks? Anything? Anytime you add in something that is recurring, SaaS is recurring. Paid newsletter is recurring. The recurring element makes it significantly harder than people realize. And so in my mind, like, it seems like the longer road, but it actually is the shortcut. You shortcut so much of your learning. If you can go, how do I. How do I get people to buy one single thing? And then, in an ideal world, a paid newsletter is the one single thing over and over and over and over and over again. One of my. One of my favorite examples, this was my favorite book that I read in 2022 or 23, I can't remember, is George Saunders. He's an American author. He teaches a Russian literature class at Syracuse, and he wrote a book called A Swim in a Pond in the Rain. And the book is him taking some of the most iconic Russian short stories and breaking them down. So you read the short story in the book, and then he explains what's going on in the short story. Amazing book. I loved it. When it ended, I was like, I want more of this. Then I find out that his paid newsletter is the exact same thing as that book every single week. So he writes this book. It becomes a bestseller. Writing community goes crazy over it. Everyone goes, that was amazing. I would love for you to do that more. What does he do? He starts a paid newsletter where he goes, every week I pick a different short story. And then I break it down. So, like, that's one of my favorite examples of you get someone to buy one thing. I bought the book. Then he goes, oh, a lot of people liked the book. Why don't I do the micro version of that book every single week? That is fundamentally what a paid newsletter is. It's a book that's. Just to succinctly put it, a paid newsletter is a book that never ends. So it's like, you have to figure out what is the book that never ends. And the fastest way to figure that out that I've learned is like, start with a standalone and then if something works, then you duplicate.

[Sebastian]

Got it. And what might that standalone look like? Is it going to be kind of a few of what the newsletters would be, but put together as some kind of a tangible asset or something completely different?

[Cole]

Yeah, no, I would start with there. Yeah, don't overcomplicate it. It would probably be something like that combined with, I don't know, research reports, combined with some commentary, you know, like some. And, and I would try and tailor it to a specific. I would try and find a way to make it specific to some sort of industry or some sort of specific reader. So, like, an easy example would be, here are all of the new regulations that are happening and here's how they're specifically going to impact like these business sectors. In this, in this report, I'm going to explain what the regulations are, what, when they take effect, who's going to get affected by them most, how much it's going to cost you, how to best navigate those regulations. Like, that would be an amazing paid product. If that works, then you go, okay, how can I do that on a micro level more often?

[Sebastian]

And would you ward against going B2C? Because the audience I see for this and the audience that I think I have on socials on the newsletter are broadly people for whom politics is their hobby and they like to go to dinner parties and have arguments and they want data and arguments to back up their views. Is that going to be a much harder route to go down?

[Cole]

Not necessarily. I don't, as a mentor once said to me, you're going to have a bag of problems either way. It just depends on which bag of problems you want. So for that, if that's the data that you have, maybe you go more of the line of like, it reminds me of. You ever read the book Freakonomics?

[Sebastian]

Yeah.

[Cole]

Like, it's, it's like they took really weird things and they would tell you like these weird statistics about society. Like, could you do a Freakonomics of politics? Like, what are, what are like 50 things that are happening right now that are super weird, but if you know about their great dinner party conversation like you, you can always find a way to make it work. It's just, that's the learning process that you have to go down. And it's easier to do that with a standalone than to go, I'm starting this big paid newsletter.

[Sebastian]

Got it. Thank You. Yeah, just using the final question. I mean, my. One of my thinkings was create an EEC along these lines and use that as the, as a jumping off point or from social. Would that make a nice paid product, a low ticket paid product? If you, if you kind of put five of these together and package them, is. Is that the kind of thing that, that might fit the, the criteria you've been talking about?

[Cole]

Yeah, it. It can. This is, this is why, though, like, the only way to learn how to monetize in this way is you just have to try because it's, it's like nothing will teach you more about how to monetize the specific person that you're talking to or who's reading your work than trying to sell them something. And the moment you try and do that, the answer reveals itself.

[Sebastian]

Brilliant. Thank you so much. I'm gonna go and have a think about this. That's a helpful curveball to Fame my way.

[Cole]

Appreciate it. Awesome. Great. Thanks for asking, Sebastian. And yeah, for everyone else here, part of why I don't mind jamming on some of these other things is because these are all things that you can help clients think through. Like, especially if you start ghostwriting emails for clients, at some point, they're probably going to be like, hey, I heard about Substack. Should I launch a paid newsletter? If you can, if you can speak intelligently about how to do that, how to do that. Well, pros and cons, when they should do that, when they shouldn't do that, different offers that work inside of that, that makes you extremely valuable.