204: The 15-Minute Newsletter Hack That Keeps You in the Primary Inbox Forever

Hey Jay, I am super excited to jump in and talk with you today about all things newsletters, but before we get into that, I want to just tell the audience a couple things. So you have this, do this, not, not that podcast. And I will say it's one of the few podcasts that I listen to every single week. But I think I mostly listen to it honestly for the recommendations on TV shows that you're watching and all that good stuff. But I want people to check that out and I'm going to put the L to that in the show notes, but thank you. Outside of that, I want to make sure that people know about these events that you have that are coming up now. I have attended Guru events for the past two years. Like I saw the whole Debbie Gibson thing this year, the whole 80s kind of get up. That was fantastic, very entertaining. But you also have one coming up that I. It's brand new, you mentioned. Fantastic. So I want to make sure that people are familiar with that. So tell us just a little bit about that before we jump into all the fun stuff here.

Well, first of all, I appreciate you because obviously you have horrible taste in TV just like I do, but I won't hold that against you. All things reality TV is my world. But in terms of our events, everything we do is free and virtual, so it's for everybody to go to. So we have an event in June called Eventastic, which will be the world's largest event about events. So if you put on webinars in person events, virtual events, you'll to become a better public speaker or get sponsorship sales. Eventastic is going to be wild. And then in November, we got our email conference called Guru Conference, which is about 25,000 marketers will be there. And it's fun, it's crazy, it's free, it's virtual. So thanks for calling that out because we're excited about it.

Yeah, I'm definitely. I'm going to be at both of them, just so you know. I'm definitely going to be there. But before we jump in and talk about newsletters, I have to ask you, what is your latest recommendation for a TV show?

Oh, my goodness. Well, I'm all involved with Love is Blind. I'm in the middle of it. You know, we're in season eight right now, so I'm very involved with Love is Blind. I'm also very involved with the Bachelor, which nobody else is watching, but I'm still watching the Bachelor, which is a disaster of a season. And then lastly, I got White Lotus going on as well. So I got a lot of TV that I'm trying to consume. It's very, very hard. And by the way, if anybody cares, Grey's Anatom of me, their 21st season premiere is. This is right now. I cannot believe they're still putting out new, new episodes of this ridiculous show.

So there's a lot out there that's crazy. 20 something.

Okay. Do you know when they started that show, the iPhone did not exist. Taylor Swift had not released an album yet. I mean, that is how long the show's been around. That is weird.

That is weird. So you do have. I have to say, you do have taste in tv.

I do. Horrible.

Oh, my gosh, The Bachelor. I. I love some of the Bravo TV shows. I love Southern charm. So I'm a big, huge, like, Charleston fan. It's one of the few that I'm still worth watching in terms of reality tv. The other one I just finished that I want to tell you about is Landman. And I was in Austin, Texas last week for the Newsletter Marketing summit, which we were talking about before we started recording. And the Uber driver, when it's taking me back to the airport, he told me, he says, because we're just. I just mentioned it. He says, it's exactly like that. So when you watch that TV show, if anybody's listening here, he said, what you see there is exactly how it is because there it is, one of those oil rigs.

So that's like quality tv. That's legit.

Yeah. Great. Yeah. Billy Boxer, I mean, he's. He's awesome.

He's out there. He's wild.

All right, I think we need to get a little bit serious here, maybe just a little bit and jump in. And I want to talk about newsletters because everybody who is listening here, they either have newsletter or they want to launch one. Or maybe they have one and haven't really been doing kind of, you know, or it's just not working for them. Right. So let's talk it. Talk about, first of all, growing our newsletter, because I know that's one of the things that a lot of us struggle with. So what would you say to people, you know, what are some of the best ways to grow a newsletter and what have you seen across the board?

Yeah, a few things. Number one, the easiest thing you should do is everybody should have a pop up on their website. And a lot of people avoid it for their site because, like, oh, I hate pop ups. They're annoying. I don't like when I go to a site and There's a pop up that asks me to sign up for something, but that's where you fail. Because if you have to separate your what you like or don't like or whatever because you're trying to grow your list. And if somebody goes to your website and you don't have a pop up that has one of those contact captures that says, hey, sign up for this newsletter and we'll give you a special piece of content or a special discount, you grab their email address. If you don't have that every time somebody goes to your site, then what happens is people go to your website, they check it out, they leave and you have nothing to show for it. And on average about 5% of people will fill out that pop up contact capture and you're going to be able to grow your database that way. And then the other thing is using social, the only thing about social, and I post on social all the time, the most important thing about social is getting your followers off of social media. That is the purpose of you being on social media, right? So what I mean by that is you want to post little tidbits that maybe are about your newsletter or a stat from your newsletter or a tip from your newsletter and say you want more of this stuff, sign up here or DM me and I'll drop you the link in DMS to get the registration for it. You need to be intentional on social about getting those registrations because that is the whole purpose of social media.

So great tips there. Let me ask you this. Let's say that maybe we're not getting a lot of traffic to our website or social media. You know, with the algorithms, our posts aren't getting out there as much. What are some other ways that you would recommend or that you've seen working for other people?

You know, you have to get start to get aggressive and get a little bit comfortable being uncomfortable in terms of growing somewhere. The easiest place to grow is on social media because these audiences are there for you to grab, right? They exist there. Like you said, if they're not coming to your website, they're not just going to magically come to your website. And if you don't have big marketing budgets where you're going to spend all this money to get people to come to your website, then the place that you need to be is social media. And you want to pick a platform and you want to go deep on a platform. The mistake that a lot of people make is they go, okay, I'm going to post this on LinkedIn on, on X on Instagram, on TikTok, on YouTube. I'm going to be all over the place. And that's what's going to work. That's a recipe for failure. What you want to say to yourself is, okay, I can go deep on one platform. For me, I Happen to choose LinkedIn, right? If you're somebody, let's say, like Jenna Kutcher or Amy Porterfield, they go deep on Instagram. They're almost never, for example, on LinkedIn. You want to think about your audience. Where are they? Okay? And then you want to go deep there, and then you want to start sharing and growing, commenting on other people's posts, notable people's posts, ongoing, get them to follow you, and then you start to pull them off of social. And so that audience that's built in for you for free on these social networks is the best place to go to start to build up that. That core group that you need.

The other thing I would say to folks is maybe even try a little bit of paid advertising, right? If you haven't done in the past, I'm seeing some really, really good results even with some very small budgets where people can get, you know, a few hundred leads a week, you know, from the paid advertising on, like, Facebook and Instagram, especially if your audience is there 100%. Yeah. So I want to switch gears just a little bit with you. I'm doing a webinar next week on. On newsletters. And, you know, when I send out the email to folks to, you know, get them to add it to their calendar, I tell them to email me back and tell me what is, like, one of the pain points that you have with newsletters. Well, I got an email back this morning, and she said that her pain point was getting people to respond back to her in the kind of the engage engagement with her newsletter. Any tips that you would have for somebody like that?

Well, first off, we gotta get the email opened, right? We have to get the emails open, and so we can go deep on subject lines to get those emails open. There's no doubt about it. But if you want to get people to actually respond, right, the number one thing you could do is get people to give their input on something. I'll give you an example. With my newsletter, I do this about once a quarter. I'll send out an email and the subject line will literally just say the word question. That's it. All right? And they open it up and I say, listen, we're working on the content for next quarter's podcast, and we'd love to hear. What is it that you think we should cover? What's on your mind? What's your biggest pain point? And it doesn't have to be, let's say you don't have a podcast. Say, hey, we're working on our topics for our upcoming newsletters. What's on your mind? What's your biggest issue? What do you got going on? Just reply to this message and let us know what you think. Okay. And people love to share their opinions. They love to be able to give their two cents. And here's the secret sauce about doing that. Not only do you get back incredibly valuable content ideas, but the trick to email is when you get somebody to actually reply to a message that you've sent from a technical perspective, you will now stay in that person's inbox pretty much forever. Because what you are telling the receiving and sending email infrastructures is that, yes, I know this sender, yes, I like this sender because I'm replying to their messages. So doing these campaigns ongoing where you literally all your entire focuses is getting that reply will have long term benefits far beyond just the content information that they're sharing.

That's some really great tips. And you know, one of the things they mentioned in the newsletter marketing summit last week was like one of the big players. I think it was Morning Brew, but I may have mistaken that. They spend like, they get responses back every single day, like two to 300 responses and we reply back to all them. So it's giving them all that content of what they can put in future newsletters. But it also is kind of doing that signal that you mentioned there. Yeah. So I want to talk a little bit more about subject lines because you, you made a good point. Right. You got to get the good, good subject line in there. And I know that you have subjectline.com where people can go in and get feedback on their subject lines because it's so important. Walk us through that. I know in one of the recent podcast episodes that you did, you talked about don't put that personalization in the subject line. That was like from the 1990s. So tell us a little bit more about what you're seeing today in terms of good subject lines.

Yeah. Your subject line is so important. And the thing that people don't realize is nobody actually reads the whole subject line. You could literally write Jay likes horrible TV at the end your subject line. Nobody would see it because what we do is we do our social scroll through our inbox and we're literally looking at the first few characters of the subject line. You may not even realize that's what you do, but that's what we all do. And that's how we're determining whether or not we're going to read a little further in the subject line, whether or not we're going to open up the email. So forget about what you write in the subject line. People are always like, well, how many characters should it be? Should be less than 50. Who cares? That's irrelevant. What you want to think about is the first few characters, so what should you be doing? So, for example, if you start your subject line with a number, an actual number, you know the seven things all small business owners need to know. Oh my God, what is it? The three pitfalls to avoid an actual number as the first character subject line will lift your email open rates. The percentage of people opening up your email by about 15%. If you capitalize the entire first word new, all letters are capital or just in all letters are capitalized, that also will lift your open rate significantly. Why? Because it stands out just a little bit and gets people to stop that social scroll and look at it. Or put something in brackets, right? Let's say you have some sort of new guide. You just write the word guide, you put it in brackets or you have a big discount, 20% off. You put that in brackets and that's a start of your subject line. It will crush it. And none of those things. Don't listen to anybody that tells you that special characters in your subject line like brackets or capitalization or emojis or putting the word free or an exclamation mark is going to cause you go to the junk folder or the spam folder or the promotions tab. None of that is true. That's not the reason that happens. And content filtering, the words and symbols that you use, it used to be the reason you got filtered. It is not the reason anymore. So I want to liberate everybody to just write what they want to write.

I love that. I love those tips there. Another question, Jay, that I get constantly is how long should my newsletter be? What are you seeing from your customer base and just being out in the industry there.

So one of the things that you should plant in your mind is visually boring. The concept of being visually boring. What do I mean by that? So let's say you get a text from a friend of yours, right? We're on this call right now. You get a text and it's a big block of text. You don't know what it says. You're like, whoa, I can't. That is, that's a problem. I don't know what it is. I'm going to look at that later. Now you're only willing to look at that later because it's a friend of yours, right? But what we do is when we send out our newsletters, if we have a big block of text, actually anything over four lines in any given block of text, we open it up, it feels like work. It feels visually boring. We don't. It doesn't matter if it said I won the lottery, I'm not reading it. So what? However long your newsletter is, okay, you want to make sure that you're breaking up the content blocks so it's not a turn off visually right out of the gate, okay? And then the other thing you want to do is have really good spacing in your newsletter. Big wonderful headlines that are kind of grabbing somebody and not boring headlines in each different, like, subject section of your newsletter. So a great headline would be just like a stat. 71% of people are doing this, oh, my goodness, whatever. And then you have that block of text. You want to be a little sensational with each part of your newsletter. And you also don't want to save your best stuff for the bottom. That's another mistake we all make. Like, oh, the best tip I got, or the best piece of content when I stick at the bottom to make sure everybody reads. That's not what happens. You got to get your absolute best content right up top. Because then people like, oh, this doesn't stink. I'm going to keep reading. And so that's what you really want to think about. So of course shorter is always better, but it's less about how many words or how long it's going to be. It's more about how you lay it out.

I love that. So really having that white space, having the good headlines there and putting your best stuff at the top, I love that. Now, the folks who are listening here today, they're going to be experts, consultants, kind of digital product creators. They might have courses, memberships, and they're looking to monetize, right. Their newsletter and their email marketing in general. So what would you say? What's working best for people like that? Are, you know, is it sponsorships, is it affiliate marketing, just selling their own products? What are you seeing? Or maybe it's just a mix of all the above.

I mean, it can be a mix. First of all, you need to have a, you know, decent sized audience in order to really monetize a Newsletter, what works and what doesn't work. If you're going to have ads or sponsorships in your newsletter, the number one thing you should be doing is endorsement style ads, for sure. And that's to be stuff that you believe in. So I have a newsletter, right? And I get hit up a bunch, hey, I want to sponsor your newsletter. And if it's not a product or service that I, I have to believe in it. I won't take the sponsorship because the ads that work are the ones where I can write. This is really awesome. This piece of content is amazing. You got to check it out. And I'm not full of it, right? Because then when I tell the people that are reading my newsletter, go and check this thing out and they do, the next time they read my newsletter, next time I say check this out, they're like, oh yeah, that thing Jay said was valuable. I'm going to do that. So you have to have kind of a long term thought process in your mind about the sponsorships you are willing to take. Right. And then the other thing is I'm not a big fan of selling on CPM. Okay. Cost per thousand meaning, okay, I have 10,000 people on my newsletter. I have 100,000 people, my newsletter. I'm going to charge, you know, $30 per thousand people that are a part of my newsletter. So it's $300, 3000. Whatever it is. I don't like doing that because it, it, the dollars are just too small. Right. It's just, it's impossible to really make any money if you're going to do that. So I believe firmly in a, in a flat rate that you're selling access to this curated audience, that it's not really about exactly how many people there are, but the fact it's really, really hard to reach these people. And I'm going to do an endorsement style ad for you. This is a big deal. So you want to sell it as a flat rate. So that way you're not kind of like leaving a lot of potential money on the table.

I love that, love that. So let's just say they were, you know, selling like something they were endorsing. Maybe, you know, I know you do Marigold in yours. Maybe it's something similar for their particular niche. Saying maybe they do that endorsement for like $300 or $400 or $500, depending on how big big their email list is.

I also don't like taking one one off deals, quite frankly, because, you know, you sound, you don't sound like you're being real, right. I like to be able to say, listen, this is going to take a story, I'm going to take me a little time and look, I appreciate the fact you even said that like Marigold for example, that's stuck in your brain because they've been a sponsor of mine for a long time. Right. And that's how it works and that's when the sponsor gets value and you're able to build that connection with whoever you're marketing to. So it's another thing to think about that you want at least a multi insertion buy.

I think that's a really good tip because I, you know, I probably have made that mistake in the past myself, right. Just doing the one offs but I feel like I could get a lot better results for them had I been promoting that particular vendor or you know, affiliate partner over a period of time. So along that lines, let's talk about selling in emails. What mistakes are you seeing people make.

There and using emails to, to just.

Like, yeah, to sell. Like a lot of times I get questions from folks, they're like, I'm promoting my offers in my emails but I'm not getting any sales. What am I doing wrong? And I know that's kind of a loaded question, but are you seeing like any mistakes people are making there?

Yeah. Well, first off, cold email, which is fine if cold email is your strategy. You will fail if all it is is cold email. What I mean by that is let's say all you're doing is sending to your database, I got this product, I got this thing, buy it by, by it, download it, it's free, try it, whatever. And you're just doing cold outreach. You will fail because the way that email works is this idea and Gary Vee talks about all the time for social media, but it works in email. It's this idea of give, give, give and then ask. And you have to think about it that way with like, with thought leadership information. Meaning you want to send stuff to your database that is really valuable to them without you asking for anything. Okay, this is a new piece of content I found. It's ungated, it's really cool. I just saw this article, you got to check this out, whatever. And when you're doing these emails, okay, you're not saying, and by the way, buy this for me. By the way, subscribe, by the way down. No, you're like, I just want to get this in your hands. I think this is really valuable, whatever. And then you do that a few times in a row like three times in a row. And then that fourth email, you go, listen, I love the stuff I've been sending you. I wanted you to check this out because I'm actually doing this really cool thing. And I think it also lines up with what I've been sending you because then the recipient is more like, wait a minute, I'm getting a lot of value from this sender, right? From this company, from this individual. Let me check out what it is they actually do for a living, right? Because it might be a value to me. It's kind of like with my event, in my podcast, I put out all this stuff and then once in a blue moon, like, hey, by the way, I would love to work with you. And the people are very open to it because, oh, great, I get all this value out of this guy. Maybe I should talk to him about what he does for a living. So it's this idea of giving value and then doing the sell as opposed to just pounding away for that sale, that is a recipe for total failure.

I love that. So making sure that we're constantly giving value in our emails, in our content, what we're doing there before we wrap it up here. Jay, any last minute tips for the audience that related to email marketing that might surprise them a little bit?

Yeah, I'll give you a couple more that I think people don't do enough. Number one, your call to action buttons. You put buttons in your emails, right? You have those rectangular buttons in your emails. The words on the buttons can be a game changer in terms of your response rate. So, for example, let's say you're trying to get somebody to register for a webinar, an event or something like that. When you send out your promo, is the word on that rectangular button, does it say the word register? Because if it does, that's a fail, right? That's what you want them to do. You always want to frame in your mind what's in it for the recipient. And when you write your call to action buttons, whether it's for a webinar, a sale, a piece of content, doesn't matter. When you write your call to action buttons in first person click through, rates rise by about 25%. What that means is instead of the word register, it would say save my spot. Instead of register, it might say, I want in. And it gets that person just a little bit excited when it's written in that. In that first person. So messing around with the words on your call to action buttons are really valuable. And then the other one, I think that people forget about is using a PS in your emails. You especially any letter format emails or especially in newsletter emails, you want to add a PS in your emails and then you want to have a link to whatever your offer is that you are pushing or whatever's going on. Because the way that we zoom email is we read the subject line, we read the headline, we skim the body copy and then we look at the ps. And just by having that PS which costs you no money, you will see your click through rates overall rise pretty significantly.

So Jay, thank you for being here with us today and all the great tips that you gave us related to email marketing and newsletters. Can you let people know where they can find you? And I will make sure that all the links are also in the show notes.

I appreciate that. Yeah, I'm always on LinkedIn sharing horrible memes and stuff like that. So Find me on LinkedIn. My podcast is do this, not that for marketer. For marketers. You should check that out. I appreciate that. And if you really just want to hang out with me@Jay Schwedelson.com you'll find out all my nonsense there. So this has been super fun. Thanks for including me.

Yeah, thank you, Jay.