In this conversational interview, Matt Ragland and the host break down a simple framework for building successful newsletters, the "3 L's": Links, Letters, and Lessons. They explain each format: 1. Links – a curated link dump that adds value when the creator has authority or strong taste; relevance to the niche and contextual commentary are essential. 2. Letters – a personal, narrative‑style email that shares the writer’s observations, stories, and takeaways, anchored by a clear promise of what the reader will learn. 3. Lessons – how‑to, step‑by‑step guides or manifestos that solve a specific problem; these are evergreen, can be repurposed into courses or automated email series, and often drive offers. The discussion also covers practical considerations: the need for a clear promise, the importance of audience taste, how to combine formats (e.g., a personal letter followed by a few curated links), building a library of evergreen lesson content, and turning newsletters into revenue‑generating assets through automated series and offers. Real‑world examples (Tim Ferriss’s Five‑Bullet Friday, Ethan Strauss’s newsletter, Sean Puri, Todd Snyder) illustrate each L. The overall message is that by choosing one of the three formats—or mixing them—creators can consistently produce high‑value newsletters that grow an audience and support business goals.
Chapters
3 L's. 3 L's to make your newsletter a W.
Get that W. Yeah, eat a W.
What's the first one?
The first one is links. This is often the easiest place to start a newsletter is by having a link dump, a curated set of links, recommendations. Often should be related to your niche. Because this goes back to like, people aren't going to care random links that you find on the internet unless they already care about you. If you already have a platform, if you're already kind of famous, even internet famous, but like Sean Puri, My First Million, also like very famous on— famous in the Twitterverse and sold, sold a couple of companies. He has like his like 3, 4, or 5 links. 5 tweets that he likes, but people care about that because he's Sean. If I started sharing 5 links, people would be like, what? Why are you doing this? So like, that's— that is something that you can do, the link dump, but it has to be contextual. My friend, uh, Hans Loray does a really good job with this. He doesn't always send link emails, but when he does, they're related to design, to real estate. These are things that Hans talks about every single week in his newsletter. So when he has a link dump related to design, interiors, and real estate, people pay attention and they love them.
Yeah, you're playing curator, you're playing quarterback, you're playing point guard, you're organizing everything in a way that gets someone to an outcome without you necessarily creating the content that gets them to the outcome, right?
Right.
We can think of countless examples of these these types of newsletters that have gotten really big. But like you said, Matt, they're often by successful authors, successful creators, successful people in their niche, right? I'm just imagining, let's go back to the fashion example for a second. I'm imagining like the biggest well-dressed model on Instagram, right? Who has a newsletter and is like posting links to outfits of other famous people that she loved this week, you know? Yeah.
Or it's like a fashion designer like Todd Snyder. If Todd Snyder like had, had a link dump for like things that he thought were really interesting and compelling, whatever they were, people would find that interesting. But I guarantee you that people would actually find it more interesting. It's like, hey, here are other designers that I like. Here's something new that I didn't expect to see. It kind of surprised me. I think people would still like that more. But yeah, that's a specific design. That's a specific example from the fashion designer space.
Yep. You could, you can think about it with music. I'm thinking about it with business content. I'm thinking about it with sports. I'm, there's, there's examples of these newsletters that already exist everywhere. Right, right. And the common through line with all those, not only are these like already kind of successful creators, if you're not a big famous creator and you really wanna do like this curation style, you really gotta have like dialed in very great taste. Right. And taste is very hard to develop. In your taste is unique and it's, it's a lot of like, like extra exterior work to get people into this curated newsletter feed. So, so that's the first one.
Yeah. And this kind of goes into the second one also because each of these, you don't have to make your entire newsletter about like this particular type. These are types of emails that you can send. Now you can make the entire, like Five Bullet Friday from Tim Ferriss is a good example of like, It's literally Five Bullet Friday. Each of those bullets is a link. But again, Tim was already bestselling author Tim. Tim was already like host of the Tim Ferriss Show podcast, you know, number one on iTunes, uh, Tim Ferriss, when he started Five Bullet Friday. But what you can do is use a little bit of that strategy. And this is actually the— I have like a combination of these first two L's. Where I have the letter. The letter is the second one, and that's more personal. It can also be like related to your niche, to your topic, but it's like, here's what I'm seeing. You could also think of it as like very observational. Here's what I'm seeing. Here's what I'm learning. Here's what is interesting to me. But it is more in a letter format than saying like, hey, here are 5, 5 bullet points, 5 links. That I can share with you. So I'm putting my perspective into it. And the way that I combine those things in my like personal weekend wrap newsletter is that I have the letter aspect and then the last 2 or 3, the last little section of is like, hey, here are 2 or 3 things that I found compelling and wanted to link you to as well. So I'm building that tastemaker while like the majority of the email is focused on more like a personal letter, observation, learnings that I've had.
Yeah, I think the letter is the most common way to have like a strong newsletter. There's so many that I, that I subscribe to. I'm thinking of Ethan Strauss right now. His newsletter is just so good and so relevant to me. Like it's sports, business, media, things that I really care for outside of this whole creator world and even connected in a little bit. But it's to the point where like I not necessarily like align, but I just want to get Ethan's take. So badly. Like, I will drop everything to read it. And it's his perspective. It's what— here's what happened to Ethan. Here's stories he tells from writing about NBA players. Here's his thoughts on current events in the sports and media and business world. Like, he has a take, right? So a letter, the second L letter, can be like take, story, experience. And you always kind of want to wrap it up with like a takeaway. So take and takeaway. There's really no point in a letter at that point. You're just doing like, like pen mail. Here's what happened to me.
We've used the phrase promise a couple of times already. First, when talking about like with your landing page, what's the promise that people are going to get in your newsletter? Another way to think about this is in the letter, the actual newsletter that you, that you write. What is the promise of what people are going to learn? And you could all say like there's the letter and then like, what's the lesson? What is that takeaway that you said? Making sure that that's really clear. So it's not just saying like you don't want it to be like personal journal kind of stuff.
That's what I meant.
Like, what are, what are you— and you've actually helped me with this. I've made a couple of YouTube videos recently that are like, hey, this feels more like a letter to yourself or like a personal journal more so than like a specific actionable takeaway. So still keep those things in mind. I wouldn't like allow that to let you get stuck. Like if you have to fire off a couple of these just to like keep the ball rolling and keep momentum going, then that's totally fine. But really be thinking about as I'm writing my letter, my newsletter letter, what is the lesson? What is the takeaway that people will have when they read it?
Yeah, you either want to start with that, like start with the end in mind, start with like I wanna write something that helps people with this, and here's a story I can tell or an experience I've had or, or my take on the current events surrounding this, right? So that's the letter part of it. And you, you mentioned the third L of type of newsletter and that's lesson, right? So we're talking how-tos, ultimate guides, manifestos. You come into this knowing this is like a step-by-step thing, almost like, like an, a traditional like blog post or. How we think about YouTube videos now where it's like either this showed up in my inbox or I clicked on this, and by the end of it, all of my energy will have been focused on solving this problem. Right? So the lesson is really just, I have a problem. I wanna solve it. And if you can create these lesson-oriented newsletters, like I just did one about getting more from your content. Here's how you write something once and be everywhere with it. Here's step by step exactly how to do it. That is a how-to guide manifesto to content repurposing.
Right?
So I can keep going on this, but tell me what you think about lessons.
Yeah, I agree. I mean, this is a lesson-oriented podcast, so like these principles apply to other types of content besides just newsletters, but we're focusing on newsletters today. Most of the newsletters that I wrote the first 3 years that I was growing my, my newsletter were all very lesson-oriented. So it's like how to make, make use of the time that you have, how to time block your calendar, How to organize and track your goals, how to like use a task manager, how to like, how to, how to, how to, how to. Like these are all like, let me show you the lessons that you can apply to your own life, to your own workflow, to your own creator business. So lessons are very, are very popular. Also, the other way that you can kind of think about this, and we do this with clients at Automatic Evergreen, which is our newsletter ghostwriting agency, we will talk to someone and like because I want to, like, be conscious of our clients' anonymity. Like, just using myself as an example, I'd be like, okay, Matt, well, the lessons that you teach people in your, in your past productivity content that is still very newsletter-worthy is like, on week 1, we're going to show lessons about how to plan. And on week 2 of each month, we're going to talk about time management. Week 3 is all about, like, note-taking and personal knowledge management. And week 4 is about like personal, personal habits, monthly review. There are a couple of things that we can rotate through there, but they're all very lesson-oriented. I'm not writing any letters in there. Like I'm actually like completely out of it. The team writes the newsletters based on content I have. It's lesson-oriented. And we'll talk about this next. Most, if not all, uh, lead to some kind of offer, which we'll talk about next, but That's where you start thinking about like, okay, am I basically doing how-to guides? Those are very effective and can also be very good revenue drivers as well.
Yeah. One more point on that.
Yeah.
These how-to lesson guide pillar pieces of content are evergreen. So if you make a YouTube video or newsletter about it, you can always, unless, unless the content goes out of date or goes out of style, if we're using that fashion example one more time, if it, if this isn't true anymore, then that's not evergreen. But these are often the most evergreen things you can do. So that's, that's the first point. And the second point is like, you wanna build a library of these things. It's by far the easiest content ideas you'll ever come up with. If I'm thinking about basketball right now, I, I'm gonna make this as broad as possible so everyone can understand it. I could do how to shoot a basketball, how to pass a basketball, where to stand on the floor, how to pick your favorite team, how to find the right shoes. Every, every small or big basketball thing I could possibly think of is a newsletter that we're talking about here. Like you can do a newsletter, how to do anything in your niche. They will always play, they will always hit, and they'll always be read by the people who are in that exact spot who need that exact thing at this exact moment. Honestly, this is why we are making this video right now is, is we know that people understand that newsletters are a thing. Here's exactly how to go do it.
Yeah, exactly. And the other thing is like, even if it goes out of style a little bit, you can always re-record, you can always rewrite. And especially in the context of a newsletter, this is something that you could turn into another automated series. Like, I wrote so many newsletters about productivity that were how-to guides that were newsletters at first, that then I like remix them and put them back together into like, I have 5 different 5-email courses on productivity, and they all drive to different offers that I have related to that topic. So I have a time management course, I have a goal-setting course, I have a note-taking course, and they're all pitched at the end of these how-to emails that I literally go in and look at them 2, maybe 3 times a year just to make sure that like something isn't different. And if it is different, especially in a newsletter, like if you were recording a podcast or YouTube video, you kind of have to redo the whole thing. But for a newsletter, it might just be like a couple of lines that you have to change or an image that you might need to update. That can be done in less than an hour, if not less than 30 minutes, and then it's good to go for months at a time.
Yep. To recap, the 3 types: links, letters, and lessons. We're trademarking that. The 3 L's to make your newsletter a W.
