Episode #

009

What you’re getting WRONG about email newsletters

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The HeyCreator Show is presented by Riverside — ⁠get 15% off a new subscription by using code HEYCREATOR at checkout.⁠

You know you need to be writing an email newsletter. It’s the hot thing to do.

But most creators still don’t understand WHY email newsletters are such an incredible channel for your business. There’s so many aspects of a newsletter that creators simply get wrong about their newsletter.

Today, we’re going full mythbuster — debunking common misconceptions creators have around sending a newsletter.

(0:00) — Presented by Riverside

(2:53) — The elevator pitch for newsletters

(8:42) — What creators underestimate about newsletter perspective

(13:28) — A misconception about newsletter replies

(17:02) — The math behind a $100k+ product launch using newsletter promotions only (absolute gold here)

(27:56) — What you’re getting wrong about launching a newsletter 

(31:55) — The biggest issue with newsletter writing “quality”

(40:47) — Ranking what’s actually important about newsletters

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Podcast Transcript

[00:00:00] Matt Ragland: It’s 2024 and most creators still don’t understand the power of an email newsletter. You don’t know how much money you could be making for it or how easy it is to set it up for success. I bet there’s a really good chance that you could be making a lot more money from a newsletter than you thought was possible.

[00:00:15] So let’s go ahead and talk about it. 

[00:00:17] Tim Forkin: Newsletters matter. We’ve, we’ve seen countless businesses of starting with a newsletter and what it does for their business, their creator business as it, as it goes forward. Right. So I’ll pass it to you to start. If you were to. Educate or give like a elevator pitch for why you should have a newsletter.

[00:00:34] What would you tell them?

[00:00:35] Matt Ragland: The number one reason to have a newsletter at the very least, just to collect email addresses for a potential newsletter is audience ownership. When you’re growing a podcast, when you have a YouTube channel, when you have social media, I love all of those things. I’m involved in all of those things, but at any time, That can go away.

[00:01:00] Now does it happen often? No. So I’m not trying to be all doom and gloom and scary stuff about like, your, your Twitter followers are gonna get taken away, or your YouTube channel’s gonna get killed. That’s probably not going to happen. But, if I want to connect to those readers, to those listeners, to those viewers, if I wanna reach out and say, Hey, here we are, Then a newsletter is still far and away the best way to do that.

[00:01:28] I can’t send a DM to all, you know, to all of my Twitter followers at once. I can’t like send a push notification that I like own and design through YouTube or like certainly not through a podcast. Podcasts are the hardest to grow. And the hardest to like, see who your listeners are. That’s why first and foremost, a newsletter, an email list is so valuable because you can reach out to your followers, to your subscribers directly whenever you want.

[00:01:58] Tim Forkin: Yeah. I love that point you made about basically what you said is it’s like the only real guaranteed way to show up in your audience is like. In their eyes that just for them to see your name, right? Like with the way the algorithms work, you’re not guaranteed to have your tweets or your LinkedIn posts or YouTube videos or your tech talks or your Instagram posts.

[00:02:16] You’re not guaranteed to have those be seen by the people who you want them to be seen by, right? Your fans, your followers, your audience, your customers. Maybe you don’t have an Instagram. Maybe you don’t have one of these social medias, but if you do, You probably have an email, right? You might not be on all the platforms, but you’re on email.

[00:02:33] Matt Ragland: Even if you’re like, oh, I don’t, you know, I don’t want to check my email all the time. That’s fine. Everyone has an email address.

[00:02:40] Tim Forkin: Yep. You need it. You need it for everything. And people give out their email address. Willy nilly tall. These are from corporations when they buy something. Right. So there’s, there’s a built in understanding of email, right?

[00:02:51] You get to college when you have kind of like a school email, you get to the, your first work email. You probably have a personal Gmail account you’ve used to sign up for every possible sale and coupon from, from companies that you buy stuff with anyway. Right. So. Everyone has an email and to get their email is to actually own your audience.

[00:03:11] And I agree. I think that’s the main thing. Um, the other part I would say with newsletters to tack on to what you said is it’s a relationship building tool, right? I’m big lately on this idea of the longer, the amount of time that your audience spends consuming your content, the more they feel strongly about you.

[00:03:30] And a newsletter done, right. Takes three to five minutes to read. And. Maybe even longer if you go longer and the more often that your audience not only sees your name, but reads your stuff They’re guaranteed to read your stuff. The newsletter is a perfect place to build a long term relationship unlike short form written text like on Twitter and LinkedIn unlike short form video where you hardly even know who you’re watching Newsletters are the place to be to build a relationship.

[00:03:58] Matt Ragland: Yeah. It’s also a great way to like on, on the other end of the spectrum, I think about these like very successful, but very long podcasts. Like the HeyCreator show is 45 to 60 minutes, but yeah, like these really big shows that are two hours, three hours long. Sometimes I think the longest Tim Ferriss episode that I attempted to listen to was like six hours.

[00:04:24] It was like Like it’s an audio book. It’s a lecture series. Now that’s what, that is very, very, that was a very, like, that was an outlier even for Tim. But I think about, and I was actually talking to a really big, uh, the marketing manager to really, for a really big podcaster, like you would know who, who this person is.

[00:04:43] And they have like 200, 000 email subscribers and don’t email that often as like, look, you have really long shows, you And if you can just like hop into the inbox once a month, every other week, ideally weekly, and just share like, I think a lot of newsletters could benefit by feeling like personal letters.

[00:05:08] Our friend Greg Isenberg does this. He literally calls it Greg’s letter, but If you have a really long show, or maybe you have like really in it, like I think about we’ve mentioned Doddford and his like cinema quality YouTube videos, I even think about like Mr. Beast. What if Mr. Beast had a newsletter?

[00:05:25] Then I would like, I would just like to hear from Mr. Beast about like, hey, how, how am I putting these things together? Here’s like some stuff that’s going on with the company. Here’s a couple of new, like video concepts that we have. All right. That’s it. Like almost like a letter to shareholders sort of thing.

[00:05:40] Sort of like really, really relaxed, really like behind the scenes. And if any of them were like, Hey, here’s this, here’s this other thing that I like thought of since I did the last show, or here’s this thing that I found that didn’t really make sense to talk about on the podcast, but I wanted to share with you here, all of those are like.

[00:05:59] really great ways and reasons to engage with an email list without it being like this whole big thing that you like many people like overthink. That’s one of the big misconceptions, which I know we’re going to talk about next. But if you just treat it like, A personal letter. Like that’s often a really good place to start, especially if you’re a podcaster or a YouTuber, that’s already doing like your big picture content somewhere else.

[00:06:25] Tim Forkin: Yeah. Turn the tick tock camera on here. Cause I got something, people generally underestimate how nosy people are. Right. A newsletter is a perfect place to just like tell people things that they wouldn’t, couldn’t, or shouldn’t know from the way you make your content or the things you’re thinking about.

[00:06:42] The example with Greg is perfect. It’s like, here’s exactly how I’m thinking about startups or anything in his world. He just like, like breaks the fourth wall. This is exactly what I’m thinking about this. Right. And I think. People underestimate how valuable that is. Matt, you and I are both sports guys.

[00:06:58] Like we would kill to know what like our favorite teams decision makers are thinking.

[00:07:03] Matt Ragland: Uh, especially this week,

[00:07:04] Tim Forkin: the draft week

[00:07:05] Matt Ragland: that we were, I would love to know.

[00:07:08] Tim Forkin: So yeah, we would love to like peek behind the curtain, right? The idea of a newsletter that peeks behind the curtain. If you’re stuck on anything with newsletters, I would start there.

[00:07:16] People are just generally. Underestimate the nosiness of people and that is a perfect place to start. That’s a common misconception if you want to go into this right now is like, um, newsletters don’t have to be like super professional writing. They don’t have to be these like big convoluted, like ultimate guides to things, which I think those have a place.

[00:07:36] And I think there’s a strong pillar point of content, but your newsletter can honestly just be like. Here’s what I’m thinking about this as a fashion consultant or as a real estate agent, or as a scrapbook, or as someone who rides dirt bikes for a living, whatever your thing is, like what, what could people love that they don’t know, can’t know, or shouldn’t know, you know?

[00:08:00] Matt Ragland: Yeah. The way that I thought about this, when I started my newsletter, I was really big on YouTube at the time and my newsletter had started to grow now all these social media platforms and. Uh, YouTube podcast, they can be good ways to grow, they can be good top of funnel for the newsletter. But when I started writing my newsletter, it was a lot of like little anecdotal, uh, additions that didn’t necessarily make it into the video.

[00:08:27] Or if I was like, Hey, one of the things that I would almost do, one of the other things Is like provide a commentary on the video itself. You can think of it like the director’s cut. Like I just watched Dune 2 and some of my favorite things to watch on some of my favorite movies is like, what’s the director talking about when that scene is going on or how did it set up or like, what was it like trying to, you know, for, you know, Paul to ride the sandworm machine or whatever, you know, whatever it was like, I love that stuff.

[00:08:56] And so like, when I’m doing a, one of the ways that I thought about this, the video didn’t do very well, but the email newsletter after it led to a lot of responses that I did a big video about how I stay productive with a bunch of kids running around the house or the way that I think about time management and productivity.

[00:09:16] And it was the most elaborate thumbnail that I had done. There were Legos everywhere. And I was like, had some spilled milk and it’s like this whole thing. And I was able to say like in the newsletter, Hey, I had, it took me like an hour to get this thumbnail done. And that was frustrating in a sense, because like, I didn’t protect an hour to do this, but actually like the reason the.

[00:09:38] Video came out a day later was because like that took me an hour to do instead of like 15 to 20 minutes and so I had to do it later and Then the way that I could tie this back into productivity is like hey Things aren’t always going to go exactly to plan. This is able to like get over my frustration.

[00:09:56] So I’m still like tying it in to the core topic of productivity and mindset and kind of mental health in a sense. But I wouldn’t like stop the YouTube video and be like, Hey everyone, this thumbnail took like an hour and a half to make. And I got really like, that’s not a thing that would have gone in the YouTube.

[00:10:16] But people were replying to that newsletter tidbit saying like, Oh man, this happens to me all the time. Not with a thumbnail, but like this thing that I thought was only going to take me 30 minutes, took me an hour. And then it took me another hour because my kids interrupted me or it’s time to like, Pick them up from school, all very normal things.

[00:10:35] And so this, like, I got a lot more email replies to the newsletter about like the commentary of that video. Then I had comments on the video itself. Like I said, the video did okay, but the newsletter just providing commentary was something that did really well, but it was, it wasn’t like. Doing like a whole different thing.

[00:10:55] It was just like commentary. And like, here’s what I learned.

[00:10:57] Tim Forkin: I’ll ask you this. Are you more likely to read your YouTube comments or reply to your newsletter? Reply to the newsletter for sure. A hundred percent there. They’re like

[00:11:06] Matt Ragland: real people. Like I know there are real people on YouTube comments. Don’t come at me, but there’s just something about like getting an actual name.

[00:11:14] In an email reply, you know how YouTube handles can be. And there’s so many Anons that it’s like, if I get an email reply, you’re, if I get an email reply, you’re getting a reply back from me in most cases.

[00:11:25] Tim Forkin: Yeah. That’s the other part I was going to say is like, you are having direct one on one conversations with your audience over email, even though like when you write out the big newsletter and send it, you’re not really thinking about that.

[00:11:35] In a sense, like you’re thinking of more of like, This is my big idea that I want to talk about or send, but you can, like, I’ve been on email threads with some of my favorite creators, just like back and forth over and over again for days, almost like over a week at a time where it’s like, I’m getting to know this person that I follow.

[00:11:51] And I have direct access to them now because I can reply to their newsletter. That’s another common misconception. I think is they’re treated as like broadcasts and they are, they’re, they’re big broadcasts out to people, but. You can’t like when you’re watching TV or YouTube, like you can’t start a conversation with the person who made it in the same way that you can.

[00:12:09] Yeah. You’re not going to have a whole like

[00:12:11] Matt Ragland: back and forth in the comments, like sometimes, and you might have a back and forth in DMs, but it’s like, it goes like comments replies on social YouTube and then it’s DM and then it’s email. Like those are the three levels. Phone number slash text message is probably like the ultimate, but I don’t have a whole lot of self, uh, I don’t have a whole lot of cell numbers.

[00:12:30] Uh, but. What like this isn’t just unique to us either. I remember one of the first times I was like, Oh, interesting. Was I was reading Seth Godin’s blog for years and he’s been writing daily for like 20 years. And he said something about summer camps and I was a big summer camp guy growing up. I worked at a summer camp.

[00:12:51] And so I just. You know, hit a reply, no expectations. Like, Hey Seth, love your work. Uh, summer camps have been really important in my life. And I worked there, I worked at one for a little while. Thanks for like giving them a shout out there, like life changing things. And like an hour or two later, like I think the same day Seth wrote back and said, Hey Matt, thanks for reading.

[00:13:11] Summer camps rule have a great day like very short very succinct But to get like well one Seth isn’t on social media So I would never like have DM Tim but like he replies and I’ve heard this from other people like he replies to Most of his like emails that you might you might send to him. So that was like That’s not, and I’ve had several interactions like that way more than if I’ve reached out over, over DM, especially like years ago when I maybe didn’t have quite the following or sway that I have now, not to, not to humble brag, but well, you know,

[00:13:48] Tim Forkin: No, I don’t, I don’t think it is.

[00:13:50] There’s another one that just popped into my head that we need to talk about. I think I told the story before, at least in my own content I have, but I didn’t understand. How much money newsletters could make. And I know there’s like some frameworks around this, but, uh, one of our first clients that, that we had, um, when you and I started working together, the first time I ever logged in their convert kit account, I saw like the dollar number of like, I think it’s like past six months.

[00:14:16] And that number was over 250, 000 in the past six months from their newsletter. And I’m not saying I’m not giving that number out, or I’m not going to tell who this person is for the sake of like, um, bragging at all. It’s more so just like, I had no freaking idea. That could happen, right? And the other story I use, Matt, is that you and I worked on a launch, you mostly worked on a launch for a big creator and it did 120, 000 in a weekend.

[00:14:47] And all of the, the sales mostly are coming from the email list, not social. The one

[00:14:53] Matt Ragland: I think that you’re thinking of, it was a hundred percent through email. And another, we had done a prior version of that launch for the same client where he did promote it on social also. And I think 95 percent of the sales came through, came through email.

[00:15:14] And there’s actually like, I’d have to find the tweet, but there’s a. public post about this from Ali Abdaal from a few years ago when he, or maybe just a couple of years ago when he was running the part time YouTuber Academy. And he showed like screenshots from Google Analytics and from, uh, ConvertKit.

[00:15:31] Ali had at the time like 2 million subscribers on YouTube. Over 100, 000 followers on socials, like probably close to 400, 000 across like all the socials and a mere like 120, 000 email subscribers. So the smallest audience, but I think he said it drove like 80 percent of sales.

[00:16:01] I think I’m just, I don’t have like the specific numbers in front of me, but I just remember that it was such a staggering difference. It was email and everything else. Like everything else could have doubled and email still would have been like, number one.

[00:16:17] Tim Forkin: Yeah. Walk, walk me through that because I think I have the, um, I don’t want to get this wrong for our audience.

[00:16:24] Like I want, I want you to explain it, but let’s say I had, um, let’s just say a 10, 000 subscribers. Like that’s, that’s an attainable goal for most everyone that’s listening. Right? Like you kind of need to be doing this for a very long time or have some external factors come in to bump over that 10, 000 subscriber mark, I’ll say.

[00:16:43] So let’s just say sent 10, 000 subscribers and say they. Someone wanted to launch a course or a t shirt or any sort of product in their newsletter, right? Like help me do some math on this of like how much money someone could make. Yeah. From their 10, 000 subscriber list. Um, once again, I want to reiterate 10, 000, not easy to get to, but also not impossible for most people listening.

[00:17:05] Matt Ragland: No, not at all. Cause I want to give you even some numbers on getting to 10, 000. If you averaged 555. Subscribers per month for 18 months, you would be a 10, 000 subscribers and you like, don’t get like, that’s an average. So like, if you, if it goes like most things do on the internet, the first six months you may average a hundred, but then the last six months you’ll average like 2000.

[00:17:36] Uh, Chanel growth in reverse, like saw this, like she’s been posting about this stuff for quite a while. I think she’s over like 30, 000 subscribers now, but I know 18 months ago she was at like a thousand. So it’s just, it starts compounding and starts building. So if you’re talking about 10, 000 subscribers, if we’re talking about a course, That as some of this is going to depend, I want to be clear, some of this is going to depend on, uh, what your offer is and also what type of topic or niche that you’re in.

[00:18:10] Okay. So there can be some variance here, but on average, let’s say that you’re offering some kind of like relatively short course, think like Justin Welsh’s content OS or LinkedIn OS. That’s something that like. A lot of listeners are probably familiar with. We actually, we have a lot of clients that come in and say like, can you help me build a Justin Welch style course?

[00:18:32] So shout out to Justin for changing the game. I would expect to have like an eight, eight ish percent conversion rate. So that means that Over the span of maybe two or three launches of this thing, let’s say in a year, you can convert 8 percent at 200. So that is 200 times 800. 800, uh, customers, that’s 160, 000 on a 10, 000 person email list.

[00:19:08] Now you might even say like, Hey, Hey, you know, 8 percent is too high. It’s probably more like 5%. Again, like you can play with all these numbers, but in really simple, really round numbers, 500 customers, 200 offer. That’s a hundred thousand dollars. And yeah, I’m not saying you should expect. 100, 000 launch every single time you throw this out.

[00:19:33] What I have found the way that I can, I got to my first hundred K in courses is that the first one was like 40, 000. And then the second one I like extend extended, expanded. I could do like some different things in terms of creating different tiers on the value ladder. And the second one. would probably be around 40, 000 again.

[00:19:53] It just might be like, it’s a 500 offer and with some like cohort element to it. And then like, it just kind of goes from, it just kind of goes from there might do a flash sale and make 20, 25, 000. That was kind of my progression to the first hundred K was to do like 3540, do 3540 again, and then run a couple of smaller sales that would get to the other, like 30 ish that I needed to hit that first hundred K, but it was within, it was in about a 12 to 18 month period that I was able to do that.

[00:20:24] I was also doing sponsorships. I had some brand deal opportunities. And the other little thing about this is that 10, 000, you can, you can get sponsors for a lower, like subscriber number than that, but 10, 000 kind of is a magical number for subscribers also for a sponsors, I should say also. And you could probably expect.

[00:20:47] that for a brand sponsoring your newsletter at 10, 000 subscribers, assuming an open rate of around 50 percent and a click rate of between three and 5%, you could probably do like four to 500 per email. So you’re talking about 1, 500 to 2, 000 per month for sponsors. Now, again, that’ll vary. I also recommend if you’re early on to, like, book your sponsors in, like, three month blocks.

[00:21:20] So try and get them, like, I would rather have someone come in and say, if I was going to do 500 per send, four sends a month. That’s 2, 000. I would rather book 5, 000 for three months up front than try and do 2, 200. So that’s, I mean, we’ll have to have Justin Moore on to talk more about sponsor stuff. We could probably like bring in some of his summit content.

[00:21:43] But yeah, I mean, the money, the money’s there. Uh, the money’s there in the list. The, the, the money’s in the list for sure.

[00:21:50] Tim Forkin: All of that to say, this is why you should get to 10, 000 email subscribers. This is the value of a newsletter. When I first understood like how that equation kind of works, where it’s like, you’re probably going to be between three and eight, if you’re lucky, 10 percent of your list buys at any given point or over the course of a products like life cycle.

[00:22:13] Um, And then the dollar amounts attached to that, right? So we talked about the different like ladder of products we haven’t done on the show yet. Like we’re going to where like there’s 50 products, there’s 100, 150 products, there’s 500 products, there’s 1, 000 products. Right. And obviously as that dollar number goes up, your percentage likely goes down, but it all kind of comes out to the same of how it was going to be.

[00:22:35] All of this, once again, to say like growing the email list and sending consistent, awesome newsletters that are directly to your audience, that point people to offers and point people to what you want them to go to. That is like the math behind it is, is the reason why you do this. Right. And I couldn’t see that as a junior employee working with you, Matt, and everything that we’ve been doing is like, we’re writing awesome newsletters, but I didn’t know the next part of it, which is like the actual money behind why, why we’re doing this.

[00:23:03] Matt Ragland: I want to. Talk a little bit about like what goes into a newsletter or an email marketing campaign, like how to get started with it, what you should focus on, what you, we’ve talked a little bit about what you should write, like the commentary style, the personal news, the personal letter I know that One of the challenges that people have is feeling like they’re making a big commitment to writing a weekly newsletter.

[00:23:31] And I do believe that weekly is best. I would, I wouldn’t do every other week personally, if I was not able to do weekly, I would rather write monthly and start to like build my queue of potential weekly emails, but if you’re not ready to commit to weekly or even monthly. Even knowing the things that we’ve said, and we’ll continue to say about like, Hey, you’re probably overthinking this.

[00:23:58] You’re probably making it a bigger deal that it has to be. You’re probably comparing your own writing to some of the biggest newsletter writers and creators in the world. We can discuss all of those things, but very first thing, this is, I think, a common misconception and a way that people get stuck not having a newsletter or any kind of email marketing.

[00:24:19] What I would do first is have a landing page that I can point to on all of my socials, on my podcast, on my YouTube channel, all the things that shows them what my newsletter offers. Like, what’s the outcome for them? Don’t just throw something up that says like, I send, I send an occasional newsletter with updates.

[00:24:41] Like, there are so many. I did a, I did a newsletter breakdown for a nonprofit here in Nashville. I said, subscribe for updates. I was like. Look, nobody’s subscribing for updates. They don’t know what that is. Tell stories, all that. Yep. So on, but so have a lead magnet, which is just like a reason and incentive for them to sign up.

[00:25:04] But then what I would do is have a combination that’s like a welcome slash teaching series. So like when I was doing productivity, I would basically have like, I had this whole like, The productivity flywheel, the like three keys to better productivity. I had these like pillar pieces, these pillar topics.

[00:25:24] And after writing the welcome email, I just spent like one, maybe two emails talking about like each key topic of productivity. So I had an email talking about like goal setting, weekly planning, daily time management. like personal knowledge management. So that’s five emails right there, you know, welcome.

[00:25:44] And then those four key topics talk about like the productivity mindset, what to do with kids. And so there are like five emails right there. And even if I wasn’t writing a weekly newsletter yet. I could still have something that people are going to sign up, they’re going to get free value in right away.

[00:26:05] And then when I do start to send something, they already know like, hey, I’ve gotten something valuable, important, and helpful from Matt already. So, I do 100 percent recommend That you have some type of landing page and then automated followup sequence. You can do this in ConvertKit. That’s what we do with all of our, all of our clients.

[00:26:27] And we recommend for everyone in the HeyCreator community, we love and use ConvertKit, you know, caveat. I w I worked there for a number of years, but that way people can like come in and get something from you. Without you having like the big existential crisis of, can I write it? Can I write a newsletter for the rest of my life is basically what people like convince themselves of.

[00:26:49] Tim Forkin: Yeah. I am a big, big fan of having the welcome sequence, the queued’ up emails, like writing takes time. Whether you will admit it or not. Like I tend to think I’m a fast writer who doesn’t really edit themselves very much. Like I’d rather just go, go, go post, post, post, but the value of like being ahead on it and then like also guaranteeing that your audience, there’s never a point in which someone signs up to your list and doesn’t.

[00:27:12] Hear from you receive from you again, like that, that first window of like, I’m interested in this person. Let me sign up to the list through like, um, like they’re fully ingrained into my mind. Like, you need to be talking to them a considerable amount, uh, in that, in that timeframe. Right? Pre like already done welcome sequence and then having like different kind of guides and lists and sequences they can go through to like consistently learn from you in that beginning stage so that when you are able to send a weekly newsletter, when you’re able to, like, I think right now, my personal newsletter, I’m queued up like for the next three weeks.

[00:27:49] I have, I have This Friday, next Friday, the Friday after that. And I think maybe even one more Friday newsletter sent for myself done. Right. And that feels great. It does feel great. I have, I have free time. I have free time to make videos out of them or do anything I want, um, from, from the newsletters being done.

[00:28:06] Right. So that’s another misconception. And one thing I kind of want to add to this, like I alluded to a little bit. I consider myself a writer, Matt, you consider yourself a writer, but you don’t necessarily have to be like a capital W like writer. Yeah. You don’t have to be a journalist or, or someone who like knows AP style or has any, like any of this formal writing training to write a newsletter.

[00:28:32] I think that’s a common misconception is like, Oh, I’m not a writer. I don’t really love writing. Like, yeah, but I bet you love talking. I bet you love sharing your ideas. I bet you love. I bet you love helping people. So if writing is the way you have to do that, it doesn’t have to be the most cleaned up newsletter.

[00:28:48] I actually just responded to somebody, uh, a newsletter that I subscribe to. It’s someone I really love their content. It’s just, it’s the best. But their formatting and everything is like, To the point where I actually offered some free help where it’s like, this is, this is considerably hard to read. And like that person might need some help.

[00:29:05] But like, if you can write a simple story system study, which I know it’s a framework we love, um, to your audience, just in your own voice, how you’d write it. I mean, probably not in like the same way you’d write a text, but just sharing your stuff. In the, and think about it as like sharing your ideas as opposed to like writing, writing a book or writing an article like you are, you are speaking, you’re speaking your truth in the newsletter, however you want to do it.

[00:29:32] Matt Ragland: Yeah, it goes back to that conversational like aspect of it. And I do think a couple of things that people get a little stuck on. In addition to those things are the distinction between having a like conversational timely newsletter, which is what I’ve been writing lately for probably the past year, I couldn’t, I could get a little further ahead.

[00:29:57] on it than I am, but so much of what I’m do what I’m writing in a newsletter is based on what I’ve experienced in the past week or two. And so that can feel intimidating to a lot of people be like, well, what if I don’t have any ideas or what if I haven’t had anything like good or interesting happening to me?

[00:30:20] And that I get where you’re coming from with that. If you’re, if you’re listening and you’re kind of like mentally or like physically raising your hand and being like, yeah, that’s like, what, what’s going on, I would say that. Part of that is like internal for you, like have the willingness to like, see things as interesting.

[00:30:40] I guarantee you, like I talked about Seth Godin writing daily for 20 years. I guarantee you that that is a learned skill for him and something you can learn as well as like, just looking for what could be interesting about what’s going on. In your life, in your work, the other way to do this, and it’s probably an easier way to start.

[00:31:01] It’s how we work with a lot of our newsletter clients at Automatic Evergreen is taking a more topical approach to the newsletter. And that is something you can create Evergreen content out of. That is something you can get far ahead on. Going back to the productivity examples, we could even talk about this from a creator perspective.

[00:31:24] Like, If I wanted to like look at the month and say the first week of the month, I’m talking about goal setting. Second week, I’m talking about habits. Third week, I’m talking about time management. And fourth week, I’m talking about personal knowledge management. I have lots of content that’s already been created or lots of existing ideas.

[00:31:47] It’d be like, okay, well, I’m just going to like, I could probably, if I had like the dedicated time or I hired Automatic Evergreen myself, I could have a year of content done and scheduled ready to go. So that’s like another part of this. If you have more topical or even like you have longer form podcast material, then just take that.

[00:32:10] And turn it into a year of newsletters. I get that, especially from a podcaster perspective, like, well, it may not sound exactly like me or like the way that I write is a little bit different than how I talk or interview. Yeah, I get all that. But this is like, this is one of my pet peeves, especially about people who are not creating newsletters that are like, well, it doesn’t match my voice.

[00:32:34] Dude, you have not been writing anything. People do not know what your voice is. And I understand, I would agree, that the writing voice is a little different than the talking voice. But you wouldn’t, that’s kind of, goes more to the point though, you wouldn’t write exactly the way that you talk and vice versa, it would sound too robotic or too free flowing on either end of the spectrum.

[00:32:58] But like, the writer, the writer voice is what you make it and what you define it. So if it’s easier to just like hand it off and work with somebody that you trust, you have a good rant on this also from one of your friends about like handing off work, especially in a writing perspective. But that just, what I hear is like, well, I’ve never sent a newsletter.

[00:33:19] I send like three per year. But it definitely has to match my voice. I was like, what voice are we talking about here? There is none. You don’t write.

[00:33:28] Tim Forkin: Yeah. If we’ve just spent all this time talking about the value of getting to 10, 000 subscribers and the value of growing the list, and then like you. You understand at this point that a newsletter is valuable, but you’re, you’re so worried about like, what’s actually inside of it, the voice, the tone, the style, like to the point where you’re not sending to, to grow the list or to, to build a newsletter product that is like shareable and valuable.

[00:33:53] And like people want to sign up to like, you’re missing the forest for the trees, right? You’re so worried about how the words sound. Sound inside of it that you’re not actually getting to a number or getting to a reputation for your newsletter that can get you these financial goals that you actually want right now, if you are, if you’re treating newsletters like an art, which Matt, you and I don’t really anymore,

[00:34:13] Matt Ragland: this is another thing that people get stuck on is like writing, being like a full time, like big W writer, newsletter writer, especially like, because being a newsletter writer and being a writer are two different things.

[00:34:27] I could. I can count on one hand the number of good Like, book writers who are also good newsletter writers. Like, Michael Easter is one, Luke Burgess is one, Nat Eliasson is one. Uh, those are the ones, like, um, Susan Cain is one. Those are all people who do an amazing job with their newsletter, and also do an amazing job writing books.

[00:34:51] But, a lot of authors that I’ve talked to, have trouble writing newsletters because they think that it has to be like book level quality writing arrangement. And that’s, that’s not, that’s not necessarily the case, but people like, like Sawhill Bloom always comes to mind for me. And Sahil is a hundred percent invested in his newsletter.

[00:35:17] Like he, yes, he does some things like with YouTube now and like he, he tweets a lot, but with Sahil, he spends the vast majority of his like deep focused work each week on the newsletter. Like he probably spends, I would guess, 15 to 20 hours each week, at least, on the two newsletters that he writes. I’ve heard Paki McCormick, uh, who, uh, has a really great, like, tech and product, uh, substack.

[00:35:46] He spends 10, 15, 20 hours. Um, that is a lot of time. That’s way more time than I’m ever going to spend on a newsletter. But that is like, they’re doing like the mega deep dive, very deeply researched, and they’re not also doing like more YouTube channel. They don’t have a community going on. They’re not like trying to do client work.

[00:36:12] They’re not like building courses. All they’re doing is invested in the newsletter, and that’s what you want to do if you want to go all in on a newsletter. Then, by all means, go for it. But just so you know, like, there, it’s, that’s not a, um, what’s the word? Mutually exclusive? Is that the right thing? But that’s not a mutually exclusive decision of like, I either have to be like, Sawhill level committed or not do anything.

[00:36:40] Like, Everything I hope that we’ve been talking about this week gives you the encouragement guys are like, Hey, there’s a lot of different ways to do a newsletter. What’s important is that you’re building this asset. It’s because it can become the biggest revenue driver you have for your business.

[00:36:54] Tim Forkin: Let me ask you this.

[00:36:55] We’ll close out with this power rank, these three things. Okay.

[00:36:59] Matt Ragland: I like this. Love a good power ranking

[00:37:01] Tim Forkin: for the average creator business. I want you to power rank these three things. All right, growing the list, selling to your current list or writing like incredible newsletters. How do you rank those three things?

[00:37:13] Matt Ragland: Gosh, that’s really good. So I would say number one. Is growing the list. Number one is growing the list because if you can grow a big list, then everything else is easier. Everything else is easier. If you have more subscribers now that they have, you need to communicate with them regularly. They need to be, you know, quality subscribers, but there’s so much that you can do with A big email list.

[00:37:42] I would then say the second most important, this is tough. Like number one was super easy to think about. That is, that is the Caleb Williams level, uh, number one pick to me. Uh, the other one, it really is kind of a Drake Maye-Jayden Daniels, uh, decision. And for those of you listening, uh, sorry if that was a little over your head, but like, it’s tough.

[00:38:05] Basically, for me, deciding between two and three, I’m going to give a slight edge to writing incredible newsletters, slight edge, because I do think the content has to be good. However, when you hear this, don’t think that I’m saying it has to be like, Masterclass level, Sahil, Packy, Susan Cain, New York Times bestseller level writing.

[00:38:32] It has to be consistent and interesting. And then number three is selling. And the reason that I say number three is selling, not because it’s the least important, but I think it’s probably the last thing that you need to worry about. Because if you have a big email list, and you’re writing good content consistently, You probably only need to do like two or three big sales a year.

[00:38:59] And all of that, all of that work pays off that you’ve done for number one and number two. So that’s how I would rank them. Growth, quality sales. The other little caveat for sales is that once your newsletter gets large enough, you can bring in sponsors. If you want, you can do like a paid newsletter where we talked about this with Ryan Holiday.

[00:39:21] Now he does sponsors and a membership. But he basically has an ad free tier of his newsletter. So he’s monetizing that at 200 a year per person. While he’s also getting, now this is a daily newsletter, but he’s getting sponsors two to three days a week. So like you can do both, but yeah, growth, quality. And monetization, but only because monetization is probably the last thing to worry about.

[00:39:50] And it kind of goes more, a little bit more in waves.

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