Ep 218: Why Email Marketing Is The Best ROI In Your Business with Kyle Stout

Email marketing may not be as flashy as social media or influencer marketing, but it still remains a highly effective marketing strategy for businesses.

Why is no one talking about the fact that email marketing provides a high return on investment (ROI)?

It’s a good thing Kyle Stout joined me today to explore the power of email marketing and how it can help scale your business. 

Kyle is the founder of Elevate & Scale, a leading email marketing agency that helps direct-to-consumer brands unlock hidden revenue and put their sales on autopilot while spending $0 in extra ad spend. Kyle is an expert on leveraging email marketing to maximize revenue by improving customer retention, increasing average order value, and driving repeat purchases.

We have talked about the best types of opt-ins you should be using. What do you email people as soon as they get on your list? How to sell early and add value? Why is it critical to understand your buyers’ journey and how to write the best copy that generates connection, trust, and sales?

Do we also go over how many emails you should send to your list? What types of campaigns should you run and why? And how to increase customer retention, CLTV, and make your customers’ lives better just through email marketing.

If you want to grow your business, catch this episode and discover Kyle’s winning email marketing strategies.

Smash the ‘Play’ button to tune in now!

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Episode Highlights

03:00 What types of lead magnets are effective?

13:52 Why focus on your customers!

22:37 How to nurture and sell to increase revenue

30:52 Driving curiosity with subject lines

34:44 How regularly should you email your audience?

42:40 How to use email for customer retention

Courses & Training

Courses & Training

Key Takeaways

Kyle recommended that for eCommerce businesses, the most effective lead magnets are coupons and quizzes that provide personalized recommendations based on the results. On the other hand, for content websites, it’s best to use on-demand video training and PDF documents.

➥ Understanding your customers allows you to create targeted, personalized, and effective email campaigns. By analyzing their demographics, interests, preferences, and behaviors, you can tailor your messaging to resonate with them and can increase your engagement and conversion. 

➥ Once you have established trust with your audience, the importance of subject lines in your email campaigns may diminish. However, if you want to boost click-through rates, you can use a short punch and curiosity-driven subject lines or incorporate recipients’ names or emojis. It’s important to avoid excessive use of exclamation points and capitalization, as it may come across as exaggerated to recipients.


About The Guest

Kyle Stout is the founder of Elevate & Scale, a leading email marketing agency that helps direct-to-consumer brands unlock hidden revenue and put their sales on autopilot while spending $0 in extra ad spend. Kyle is an expert on leveraging email marketing to maximize revenue by improving customer retention, increasing average order value, and driving repeat purchases.

Kyle has over a decade of experience in digital marketing starting as a freelance copywriter where he honed his skills in brand storytelling and email marketing. Once he had developed a set of frameworks that worked consistently across different niches, he started Elevate & Scale specializing in email marketing for ecommerce businesses.

Connect with Kyle Stout


Jaryd Krause:

Imagine if your customers and clients kept saying, "Shut up and take my money." That’s what you can achieve with great email marketing. Hi, I am Jaryd Krause, and I am the host of the Buying Online Businesses Podcast, and today I am speaking with Kyle Stout, who is the founder of Elevate and Scale, which is a leading marketing agency or email marketing agency that helps direct to consumer brands unlock hidden revenues and put their sales on autopilot while spending zero dollars in ad spin. Kyle is an expert on leveraging email marketing to maximize revenue by improving customer retention, increasing average order value, and driving repeat purchases. Kyle has over a decade of experience in digital marketing, starting as a freelancer in copywriting, then moving into brand and storytelling, and then email marketing.

He has developed a set of frameworks that work consistently across different niches, and he started Elevate and Scale to specialize in email marketing for ecommerce businesses. In this podcast episode, Kyle and I will talk about the best types of opt ins that you should be using for your business, whether you own a content site, a SAAS membership business, or an ecommerce business. We will also discuss the best types of opt ins that you should be using and what sort of value you should be creating for those people who are opting in for your free offer. We also talk about how to email people as soon as they get on your list. What should you email them? How do I sell to them early and add value at the same time?

We also talk about branding, storytelling, how critical it is for you to understand your buyers’ journey and the different phases they may have been in, how to segment them through different lists, and how to write the best copy in your emails that generates connections, trust, and sales. We also talk about how many emails you should be sending to your list. Why does Kyle believe that trying to optimize for your subject lines isn’t the best use of your time? In fact, he doesn’t believe that the subject line is as important as most people believe it is. Next, we talk about what sort of campaign you should be running and why you should be running that sort of campaign. And we also talk about how to increase your customer lifetime value, increase customer retention, and make your customers and clients lives better just by using email marketing. There’s so much value in this podcast episode, I am sure you are going to love it, and I absolutely did. Now go ahead and enjoy it.

Do you have a website that you might want to sell either now or in the future? We have a hungry list of cashed up and trained up buyers that want to buy your content website. If you have a website making up to $300 a month and you want to sell it, head to www.buyingonlinebusinesses.co/sellyourbusiness or email us at; [email protected] because we would likely have a buyer. Details are in the description.

Kyle, welcome to the podcast interview.

Kyle Stout:

Thanks for having me.

Jaryd Krause:

Looking forward to this. Everyone that listens to the podcast and my stuff knows that I love email marketing, and you are a gun at this, and you have gotten people such great results, hence why I wanted you to come on. We are going to be talking a lot in this episode about how to monetize and make more revenue through email marketing. But first, we need to get people on the email lists. Is there a certain type of resource or lead magnet that you have seen that has worked well for specific types of businesses?

Kyle Stout:

Yeah, so you can do pretty much any of them for any type of business, but for example, with ecommerce I find that the more traditional lead magnets that you might use on the content site, more with business to business service don’t really do as well unless you have a big social following for the business and people are really interested in learning more, with ecommerce I like to use either coupons, which is really common, or a quiz where now you are going to be delivering recommendations on which products to get based on those quiz results, or something like that.

And then for more content driven sites, lead magnets are still great, but I find that nowadays you have to be pretty specific, so you don’t need to create these really comprehensive, you know, long, detailed guides because a lot of time people are kind of intimidated by even going through them. Such a thing, and people don’t really read as much as they used to, so I actually like to, and I do see PDF still working well, but I like to do short video training, and you can do webinar style or, as I usually do it, I just call it on demand training, where it's prerecorded and they get free access to that, and maybe there is a PDF associated with that, or maybe it's vice versa, where they get the PDF and then they get a free bonus video training with the PDF because people are more likely to go through video than they are to really read a long, in depth document at this point.

Jaryd Krause:

I love it." In fact, I am going to plug my resource that just goes gangbusters because it’s exactly what you said; it’s a PDF tool; it’s a due diligence tool that helps people to take the guesswork out of buying an online business and ask certain questions that they need to ask about the business to get certain data sets to understand the business more and be empowered to be able to buy the business or walk away. So I give them that as a tool in a PDF version, and they go away and plug it into their own word document or whatever it is, and then I also record a training video on how to use it and people say that’s the most valuable. So I think people forget nowadays how important it is to add value through your resources. People have the goal that I want to get people on my email list, and they just think I just need something to get them on there; anything will do. In fact, I think the value that you create in that resource sets the tone of what they are going to get from you in the future, not only from all the content but also all of your emails. I think that’s so vital, like it sets a good first impression when you are meeting somebody. What do you have to say to that? Kyle Stout:

Yeah, I mean, I completely agree. The days of just having something and kind of checking off the box—okay, I have my lead magnet done, but it's just not enough anymore. I mean, ten years ago, when these things were more novel, yeah, you could get away with not putting in as much effort, but nowadays there is just so much information and there is also so much competing for attention when we are online in general anyway, so the standard of quality or the expectation for what is considered quality or “value” is higher now. And I love how you have a video component with the PDF because you understand that a lot better than someone who is totally new to buying a business does.

So even though you might have this really thoughtful, super user friendly PDF, having the video that walks them through it and kind of shows them the how along with the what just adds extra value, like you said, and differentiates you from other people who have some sort of similar free resource because it shows you are willing to take the extra step to, you know, I am not just giving this to you because I have something to offer you, I just want to make sure that you actually get the value out of it so you know you move forward, and ultimately that is going to make it more likely that they would work with you in the future. So it’s a win-win for everyone.

Jaryd Krause:

The crummy short form e-books that nobody reads that are full of fluff are no longer cutting it because people quickly found out that they are not that valuable.

Kyle Stout:

No, if it’s going to be short, it’s going to have to be very specific, and it has to be a quick win. So like a checklist but like an actual useful checklist, so you are, I am not sure what your lead magnet is, but I imagine it kind of becomes, I don’t know if you will call it a checklist, but it’s like a set of parameters that if they get used to it, they are just going to be repeating that formula over and over. I would imagine you would need—I don’t even know how long it is—but I wouldn’t imagine it needs to be this huge guide. It’s more about the fact that they are getting such a thing that they can immediately put into action. So if it’s a quick little fluff piece like you said and there is no action to take and nothing where they actually see any kind of noticeable result from having gone through it, it’s pretty much a waste of time.

Jaryd Krause:

I have actually toyed with pulling down my free resource, it’s my due diligence framework that I use and all my clients use and it has helped people save millions of dollars and save millions of dollars, I have actually toyed with pulling it down because it’s so valuable that I am like maybe I should be charging for this and also people go away and use it and they get results without jumping in and joining my community and that’s cool, it’s great they can get results but a lot of people do get burned when they don’t get the support when buying a business but it’s one of those tools that you can go away and take and use it on your own and I say everybody should have somebody looking at a business before they buy, somebody experienced so that they don’t buy a lemon.

But you could go away and buy a business by yourself because that’s how good a piece of value it is in something that is just so simple and sure, and I think that’s why it goes gangbusters, and that’s why people stay on my email list, and people would talk about my email marketing, and people would love it and reply to my emails, and all that sort of stuff. It's why I got you on here because I want to improve my email marketing, learn from you, but I also want others to like listening to our conversation because it’s so valuable and so much is going to come from it.

So once we get people on our list and we know it’s like a piece of value that’s just going to knock their socks off, they are not expecting it to be that good because most of the time when you get some free resource, it’s like I will chuck it in my inbox and I will probably never use it. If it’s something so damn valuable and they are on it, what do they do next when somebody joins our email list? I know this myself, and I know there are very important steps, but I want to hear what you have to say about this, like what steps do we take once we get them on the email list to harness them and facilitate their enjoyment of being on that email list?

Kyle Stout:

Ok, so I would say there is a short term and a long term component to this, so let's just say that you are evaluating an online business to buy or that you have recently acquired one. One of the biggest low hanging fruit opportunities that’s oftentimes there is that they don’t really have much email automation set up, so I call this optimizing your sales process. It’s going to be different for whatever business type we are talking about here, but you can just think of that as a step process someone takes from being a stranger to being a customer.

So you know, for you, it might not be sure if they want to hop on a sales call at some point before they can download the resource, maybe they get some emails from you. I am not sure if you have a sales call or they can hop onto sales page where people can sign up directly but for example with an ecommerce business it’s super straight forward, they land on your site, they go to the product page, they add it to cart, they start the check out and they complete their check out and you can have automations in between every single one of those steps in your sale process and so for you know a SAAS business a lot of time they land on site, they sign up for a free trial and then there is a trail period and a lot of time there is step in between there you are really trying to get them to learn and how to effectively use the software they way that they actually like it and when the trial is up they don’t want to lose it. Then, of course, you have the sign up period. Whatever it is for your business, you want to create automated follow up in between those steps because now you're just building a machine that’s going to do marketing for you, and that’s just going to increase your sales at every step of the sales process.

Once you get that set up now that’s pretty much it, but not everybody is going to convert immediately in those initial emails and that’s where the ongoing email marketing comes and that’s where you want to do a combination of a time of nurturing and selling so in depending on what type of business it is there is going to be more education and more nurturing for some businesses than for others, you know in ecomm it does tend to be I would say there is almost always going to be a call to action to buy a product whereas if you are selling a service there is going to be a lot more continued nurturing and may be being less direct with sales and so it really just comes down to what I call a conversation starter, having some kind of angle for the email to show up, that way you are not just showing up being promotional without at least giving people a good experience when they get the email.

Jaryd Krause:

That’s awesome, so people are actually getting value from the emails, and there is a call to action, so there is nurturing and sales. I have a couple of questions around this nurturing and then also instilling our brand into our emails to make them feel unique, good, and different from everybody else’s boring emails. What are some of the things you share with people to make our emails as business owners valuable, nurturing, on brand, and also have that component of a call to action? There is a lot in that question, so I apologize.

Kyle Stout:

No, no, this is great. So there is this strategy that has existed for a long time, and I think this is the mindset that people have that when I get someone on my list, first I have to nurture them for a certain period of time, and during that period of time I am not allowed to sell. Once I have earned their trust, whenever and however we define that, all of a sudden I am allowed to sell, and that’s when people go very hard with sales. But what I try to tell people is that you can do both at the same time. So for one, don’t be afraid to sell early on, like if you have something that’s very valuable and this thing is actually solving a problem for them or providing some sort of value in their life, and even if that’s entertainment, entertainment is valuable.

You know, people think that you don’t have to cure someone of a disease to solve a problem or a pain point, but part of this is how you are communicating that to them. You first have to take a step back if you haven’t ever done this and do a little research on your ideal customers so you know them. You can call this your persona work or creating a work avatar; there are different terminologies. One resource that I highly recommend to people is a book called “Building a Story Brand." Have you ever read that before?

Jaryd Krause:

No, I haven’t. But I get the concept, and I know of some other books around this as well.

Kyle Stout:

Okay so what I like about this is that what they have done so well, Donald Miller created this, he has given this framework where if you just follow this framework you will be implementing a whole bunch of different psychological strategies that copywriters spend years you know practicing to get these techniques down and you will be doing without having to go through all the trial and error of learning to be a copywriter just because it’s very well thought out this framework which really just starts with telling a story that’s focused on your ideal customers instead of on you and your brand so you are always talking about them and what they care about and their worries, their fears and their pains and the current situation they are in and the situation they would like to be in, what before and after looks and feels like whenever they buy your products or work with your service.

So by always focusing on them and infusing some of those messaging points into each of those emails, it’s valuable because you are talking about stuff they care about. So it’s like you are not going from this phase of just trying to give everything away, and all of a sudden you are just asking, asking, asking. It’s a give and take where every email you send is trying to provide at least some sort of insight or some sort of piece of entertainment that makes it worthwhile to open it, and it reminds them that you are available to take this thing to the next level. For example, you have given them this resource, and you probably tell them a lot of what to do, like steps on what actions to take, but in a lot of services, we give away the what but then sell the how.

So it’s like whenever it comes time to sit down and actually do this thing, crunch these numbers, get into the weeds, get into the back end of the business, really look into all the details and everything, and make the final decision on how you are going to onboard and take over from the other owner, that’s when it starts to get a little more difficult because it’s not going to be the same from business to business. So having a professional work with you to handle the how is a great way to frame how you deliver your content, when it makes sense to work with you, and why it makes sense for you to constantly talk about it with them.

Jaryd Krause:

Yeah, wow. There is so much in there that I want to pick apart; the first one is studying your avatar or your ideal client. What people can do I have noticed that people can go into forums, go into comments, go into different pieces of content, and see the language that is actually being used in that niche. For ourselves, what we do in our businesses is we actually collect that data from our customers and ask them what they actually want, what’s holding them back, what they actually want, and we go away and put that into a document, our ideal client document, and we actually have the words that they use, and we instill that through all of our copy, not just our emails but on our website and everywhere because we are speaking their language, you know.

I feel like when we are connecting with anybody in a certain space, like when I am obsessed with surfing and I know somebody who is interested in surfing and is in the business of surfing, I can just talk to them versus somebody who is faking it or not because I know the language. I have been doing it for my whole life, and that’s so important in terms of trust. Someone who is telling me or trying to sell me a surf board and they are using terminology, lingo, or language that is not common in the surf industry, the trust is not there, and I can see they are trying hard, they are on the outside, and they are caring about their pockets rather than communication and trust and actually adding value, so that’s a really big piece, and then when you say you have that nurturing piece, you can sell to them at the start as well.

I think it’s really cool to understand that people have joined your email list at different stages of their journey, sometimes they join and are like, I want to buy now," and sometimes they are like, I just want to dip my toe in the water. Have you noticed that some people get frustrated with emails that are just too nurturing at the start, and they are like, "Where is the product I want to buy?

Kyle Stout:

That is a big problem because, depending on what you are selling, the higher the ticket, there is going to be a longer decision process for most people. But yeah, if you don't, then what happens is that another company that is being more persuasive and providing more opportunity to buy upfront will end up winning them over; in fact, not only have I seen it happen, but I have been that person myself.

If I could tell you a story about how I was going to sign up for a high ticket business coaching program, I had talked to these guys in the past. I was already pretty much sold, and I was trying to tell the sales guy that he was messaging me on Facebook Messenger trying to set up a call, and they do this whole thing where at first they do a shorter call and then they do a longer call and they refuse to sell to you on the shorter call, and that’s kind of like they were the ones who kind of perfected that whole thing and put it out into the market. In that time frame where I am waiting for the longer call, another OG marketer in the space came out with this whole new program that completely caught me, and he had never pitched this before and hadn’t since either.

It was more expensive; it was almost twice as much money, so we are talking about $10,000-$20,000 investment, and less than 48 hours later I signed up for the other one, the more expensive one, and they lost me because they were so quick to get me into the sales call and be available to answer all my questions and give me the offer right away, and there was also the offer was just perfect. I would have said yes to the other had I not known about this. That’s the funny thing about it that this other one that I invested in ended up being the best thing for me, so it all worked out, but it just wouldn’t have even been on my radar if the first company had had me buy sooner.

Jaryd Krause:

This is such a valuable point that not many people talk about in the email marketing space, but it’s so important in all of our businesses to understand the customer journey, the buyer’s journey, and then the customer's journey. The buyer’s journey understanding that people might sit in different seats and are in different parts of the journey than somebody else that might join the email list and speak to them and nurture them the way that they need to be nurtured versus the people that have just started to dip their toes in and being able to encompass that throughout our emails and our copy at the same time and be able to give both of those people, or I shouldn’t say it's two, but it’s the multitude of different people in different seats and what they are after at the stage they are in at their buyer’s journey. I have some things that I use that I know work quite well in my emails that I will share soon, but how do you say that you can instill that in your emails? You said nurture, but then you also sell, are there other things as well that go into this?

Kyle Stout:

Yeah, so let me share a few things because I also just want to make it clear to people that if you come out of the gate with a hard sell in an email, you are going to turn a lot of people off. It’s like, you know, that was a unique scenario, but it was just an example of how it can happen, right? In most cases, for example someone opts into email one I want them to get the brief introduction of the business, just because you know you just said that you don’t know where they are at, they might have just stumbled across your content on social media today and they just signed up for this free thing or they might have been watching your stuff for a while and you don’t know which one they are so I want them get at least a brief intro just so they know who we are, whether that’s you as a person or a business brand whatever, a quick little brief intro or some sort of segue about the thing that they just signed up to download and then a lot of time it’s a subtle thing like it could be a button down at the bottom or just a section down at the bottom that lets them know what products are available or what’s available there you are not even talking about it yet just you know you make it available so that if they are curious to look into it you have at least not prevented them from having that opportunity.

Then email 2. Now I want to go deeper into the brand story, and I want to give them the why behind the business because, for the person who needs it, if they are really vetting you and need more information, or if they are just more curious and they want to get to know your brand or your service, you want to make that information available to them. And then that one is where I am going to introduce like that’s when we get into the core offering or core collection or whatever kind of main thing is that people are interested in once they have an idea about who you are and what you are all about.

Sorry, I know I am going email by email, but I am getting into a whole other piece of how we break away because I think paving that framework will help people get started with an intro and welcome series. In the next two emails will be things like "it just depends on your business," but letting them know what kind of stuff you have as far as community building, so where your best social media is, so if you have a Facebook community, if you have a forum or an app, any of those kinds of things, let them figure out how to get more into your community where they can start meeting other people. If you have that element, that’s definitely a great element, and then in one of those emails 3 or 4, you are going to want to start sharing testimonials or reviews, things like that social proof, that kind of stuff.

So by the time they have gotten these first 4 emails, they have had the opportunity to buy, but now they have just learned a lot about who you are, what you are all about, why you are legit, and how they can dig in deeper if they want to, and then let’s just say they ended that series, and may be they are getting some campaigns or may be that moves them into another series. The way I start to differentiate people is by who I hard sell to versus who I kind of present the idea to. I call this the "offer series" or "click series," either way, and the other one is called the deadline series.

So the first one is let’s just say I have an offer I want to present to these people, I might have a sequence of 3-4 emails that I can use to present this to them and in those 3-4 emails I am going to present them this new offer whether it’s a new product service whatever it is and I am going to use more aspirational copy so I am going to be telling stories again about them, their current situation what they ae dealing with how things could be better I mean focusing on more of the positives of the benefits they will get if they sign up for this thing or buy this thing and by the way this thing could be a free thing, this could be a free offer into a free training then that free training ends up selling them to a paid thing.

So whatever it is, I am not trying to jump into future steps, I am selling into this next thing, so if it’s a webinar, I only focus on the webinar, not what comes at the end of the webinar, and if it’s a product, I am focused on the product because that’s the end; it's right there. Now the people who click on one of those emails leave that sequence and move over to what I call the deadline sequence. This is where I actually start to be more salesy, now instead of only focusing on the benefits or the aspirational positive stuff now we are starting to go a little bit more direct response, starting to remind them of what they can potentially miss out on and start may be taking things away or may be start presenting free bonuses they would get if they sign up now and if they don’t sign up they are going to miss out on those and that’s where you can do more of the salesy tactics and the reason I like to hold those back for those people is because if they have clicked through and checked this thing out I know they are interested, all the people who didn’t click at all I don’t want to hammer them with all this sales messaging because I am just going to annoy them because they are not interested.

I would rather just let them sit back and continue to stay on the list and maybe get other emails for a while until they show interest in something else, and then start to be more salesy with them. So that is my favorite thing for any type of business for how to present a new thing and then kind of decide who is going to get more salesy stuff and how to separate them out.

Jaryd Krause:

Guys, go and re-listen to that because there is so much in there. I can tell that you and I learned a lot of parallel strategies in email marketing because I have a lot of that instilled in my marketing too. In sequences and out of sequences, sequences are different email marketing campaigns based on people’s level of intent, like when somebody clicked on something, showing more intent to be closer in that journey towards purchasing ways. Coming back to being able to sell in your first email, I really love what you said about having some options down at the bottom, like, "Here is what we have got.

I have in fact just a bit of advice or something to share with people listening because I have just the email signature and it says if you are interested to hear some other ways I can help you, then I have a free thing, like a $30 product, then membership, and then like higher level things, and it’s just you can choose your own route and people can go into those different routes and be like, "Oh, this is where I am at and this is what I am supposed to do," which is so valuable, so you can call that welcome sequence, it can be like a branding sequence.

I also like to set the expectation of what people are going to get by being on my email list, so that sort of first couple of emails, like you said, and it's beautiful the way you laid it out in terms of sharing some value, sharing what you have to offer down the bottom, but it's not really that like a hard sell, and then also sharing some stories, sharing some social proof, but what I really think is cool is if you set the expectation of, like, now you are on the email list, and it has a little gif of me doing a dance in my emails.

I used to use all of these things to keep engagement and fun, and I treat my email list like Instagram or social media because I don’t like Instagram, but I use that as though I put out stories and images throughout my email list, which we can get to. But I set the expectation that here are my socials, and I will be posting x amount of videos on YouTube and x amount of podcasts, and if you want to check out these, then there they are. So you are just pounding them with expectations, welcoming them in, showing them where they can get value, and then showing them where they can buy products, and you have got just the perfect storm for them without making them feel like, "Oh, you want me to buy a $20,000 product just as soon as I get on your email list. I want to touch on subject lines. I have so much that I want to touch on, but I want to touch on subject lines. What are some ways that you have tested and found to work well with having great subject lines that create more clicks and opens?

Kyle Stout:

Okay, I am going to say something that a lot of people won’t like, in my opinion, subject lines don’t matter as much as people make them out to. What I find to matter way more is the reputation of the person sending the email, and once you have earned their trust and have got them engaged, you can get away with saying anything; it doesn’t matter as much what you say in the subject line because they are going to open it because it’s from you. Now with that said, there are a lot of ways to get more clicks, to get more opens and clicks, so short, punchy, curiosity subject lines, using their name, using emojis—these things work, but you don’t want to overuse them, like lots of exclamation points and all caps, because if you go all extreme in all your subject lines, it loses its potency, and people are like, "Oh, they just know you are exaggerating.

So you can do that stuff, but you really want to save that for when it has to be truly urgent, like the final deadline. But yea some of the easiest tricks are using their name and I just like to really drive curiosity about or may be take like something thats kind of the end of the email like say if you are doing a lot of direct response style copywriting and your emails are a little bit longer they are not the typical ecommerce thing where it’s a photo and paragraph and might be only two sentences you know a CTA button or something, then tying in something where they have to get to the end of the email to understand what that subject line is about so if you are doing daily emails like you say that’s a challenge from the person who is actually writing the emails to come up with good content and so I find it the relationship between the sender and the recipient is a lot different, like they know you personally at that point like you talk to them every single day so you can say funny stuff in your subject line or you can kind of hint to the end of that email and they are going to figure out that’s your style to do things and that makes it fun for them. It’s kind of like a puzzle, and they are like, "What do they mean by that?" and then they have to read the email to see the end of the story that you told or something like that. Jaryd Krause:

I like that you said it’s like a puzzle because it’s exactly the way I set them up, I didn’t realize that I set them up until I studied some more, like the hero’s journey sort of things and stories and films and stuff like that. For example, I would have a quirky subject line; I don’t overuse names, emojis, or usual stuff like that, I reserve that stuff for obviously sales campaigns because, hey guys, don’t be fucking around, and if you want this deal, you have got to get in on it now. But I start an email, and just like a James Bond movie, it started out just in the thick of it, somebody just got shot in the face, and the truth fell out, like that’s how I start my email, like a shark attack email, it’s like straight to the start, like my heart dropped when I saw that thing, and that’s how I start my emails, and then people have to go through the story, and in the story is the value, and at the end of the email is the how, like if you want to learn how to do this in your business or buy a business, this is the how.

So it’s cool to hear you talk about it because I do that without understanding; I understand a fair bit of it, but your saying it like a puzzle really, really resonates. now that I don’t do daily emails anymore. We send a fair few emails, and I have slowed it down, but what’s your take on how often people should be emailing? Because I have heard so many different strategies and opinions, and there is no right or wrong, of course, and I guess it’s going to be dependent on the business, what do you think is the best way for people to find the sweet spot in the business in how many emails they send?

Kyle Stout:

There are a couple of ways you can kind of measure this sweet spot, and really, these are the two most simple ways; just send as often as you can until your engagement matrix falls below your desired opening click rates, and all that. What I find is that a lot of smaller businesses or businesses that have smaller lists, this is I guess kind of a common problem, they tend to email too much, they are just getting tiny bit ahead of themselves they need to focus more on growing their lists and they are trying to do too much and I get it because a lot of times you are trying to get as much RoIs as possible and emails are an amazing sales channel and may be you are not having traction with your ads or your contents and you are trying to get everything you can out of it and on the other end of spectrum a lot of bigger brands and businesses with big lists that don’t email their lists at all or near enough, it’s either they are not emailing them regularly or it’s not even once a week and it’s like you could be emailing daily and you wouldn’t have to send to everyone on your list every time, you could be using segmentation.

That’s actually what I recommend; it’s easier to do at scale with ecommerce because it depends on how many different offers you have and how many different things you have to talk about but if you have different offers and especially if you have different price points and if you have a lot of different people in your lists that are at different stages of the journey than you can do segmentation to increase your amount of email sends and you are not sending to everyone on your email list so that’s the big problem that people get to and that’s actually the challenging thing sending emails to everyone on your list too often that’s really how people burn their list out and I say that but some people can pull off daily emails, it’s just very difficult I am sure you saw whenever you were doing it that the challenge of continuing to come up with interesting compelling content every single day is kind of a grind unless you just really love it or unless you are selling something you know if you are selling digital marketing type of offers those audiences are most receptive especially if you tell a lot of personal stories and are able to tie them into the thing that you are selling and can make it interesting or you can use the things happening in the news, if you sell anything related to finance every single day there are new finance headlines people cannot get enough so if you are selling crypto or investing or tax services there are unlimited amount of financial news coming out and now you have got something to talk about every day. But not every business has that, so that’s where it gets very challenging, and I would say if you can't keep it interesting and you notice your engagement matrix is falling, you should probably back off the frequency.

Jaryd Krause:

I like that. I like that testing the matrix and looking at the matrix and seeing what’s working and what’s not working is better than just trying to do it based on whether I think this might work. The cool thing that I have heard about emailing every single day and why I was sending a lot of emails is that if people get frustrated and don’t want to be on your list because you are sending too many emails, it’s not necessarily an argument on both sides; they are not necessarily ready to buy or really care about your emails or your product that much, so they will get off your list, and I am all about not having a big email list. I think a big email list is so damn stupid because you are paying to host people on it who don’t care about what you have.

It’s a waste of money and a waste of time, and it's really bad for your open rates and click through rates, and people will pull up, "Oh, I have got 100,000 people on my email list, great, cool, but how many do you make from your email list?" It’s an eager metric, but also on the other side, I am all about trying to get people off my email list that don’t want to be on there, which is why regular emails are good, but also I understand people are like, "Hey Jaryd, can you stop sending so many emails?

And I have because I like what you do, but I am not yet ready to buy, so I am just having them stay on my list anyway, and eventually the more emails that you don’t open, they are just going to slowly work their way off the list anyway and may go somewhere else, and if I have competitors, they might go to the competitors, which is fine; I just didn’t resonate with them, and that’s okay; they probably shouldn’t have been on the list in the first place. What are your thoughts on having a big list, a condensed quality list, and the regularity of the emails being sent?

Kyle Stout:

So there are a couple of things over there; definitely quality over quantity, for sure. High quality list—I mean, a small list of warm, engaged, interested, capable of buying people—is going to make so much more money than a huge list of people that aren’t that interested and aren’t really in the market anymore, but they just happen to be on your list still for whatever reason. So a lot of these older businesses that have been around for a while have been collecting lists for a long time, and they haven’t emailed very often, so they haven’t given people the full opportunity to unsubscribe, and they just forget they are on their lists. Yeah, it’s like there is not much value iin,like you said, paying to have all these people, and it does add up, and if you are using really good email software than adds up.

But to the other point itpoint,ally interesting to me that when I meet people in real life and they ask what dowhat Io and I say that I have an email marketing agency and explain to them what we do and the first thing they are like they tell me how much they hate getting emails from companies and everyone says that and the next thing they say and this happens 99.9% of the time is time, they say but I always buy so much stuff from those emails and that’s the funny thing about it that people complain to you about you emailing too much and they keep buying from emails so the business owners and businesses are of course going to keep emailing.

One thing that I do for people who reach out and complain I just move them to a segment where I don’t include them in the regular campaigns that go out so they are only being included in like the big holidays sales, the big product launch like you know the new and exciting stuff but they are not going to get the ongoing stuff so that’s a tactical thing anyone who is listening can do if they are getting those complaints where sometimes a lot of those people will, you get a range of everyone on your list, you have got people who are going to keep buying from you and they don’t like to get your emails, you have people who like to get your emails, you have people who love to get your emails and they never buy and you have people who do a little bit of both so its like you know if they manually reach out it’s not difficult to take care of them especially if they are an actual customer and put them into one of those segments but otherwise if you make it very easy for people to unsubscribe it’s like you said it’s kind of good for you and them, if they are tired of getting your emails they can kind of see themselves out. People who do like getting your frequent emails can keep getting them, and you are not holding back just for the sake of the vocal minority.

Jaryd Krause:

Customer retention, so you have mentioned somewhere in your copy that you help people increase customer retention with email marketing, so that’s people who are already customers. So tell me more about this because it’s very, very interesting to me. I want to know how is that done?

Kyle Stout:

So we primarily work with e-commerce businesses these day., It’s going to be different for differentindustries,s but therare are couplethingshigs that are uul so for a lot of businesses for every business, but you've got to find the number that how many purchases does that customer needs to make before they become a loyal lifetime customer so for a lot of ecomm businesses the magic number is 3, so when they get to that third purchase you are in especially if you have a consumable product you are now part of their monthly grocery bill. So part of setting up those email automations is having incentives set up to get them to make their first purchase, their second purchase and the third purchase.

They don’t always have to be coupons, they don’t always have to be discounts they could be things like offering free shipping, may be free upgrades to your order, maybe giving them early access to things or just kind of making the experience feel a little better and also just being thoughtful in looking at their past purchases to read and having an automation set ups that would recommend them to things people who buy that like this other product. So that’s one side, it’s just already having automations in place that you can continue to check in on those analytics and continue to update and to do AP testing to update those to keep that machine running and improving and getting people into whatever you define as we like get people into a VIP segment basically we are trying to work them up into that.

Another part of this is a rewards program. A lot of companies kind of neglect this, and it’s very popular withe-commerce buyer these days, there is a lot of research that shows that there are a certain portion of buyers these happen to be buyers that spend a lot, that’s one of their criteria for choosing to business with a brand is their rewards program. They would actually if two brands are selling similar products they will go with the brand that has better rewards program. Some of these people that’s what’s good for the business owner as an ecomm business owner is a lot of these consumers and they just love getting amazon packages coming to their house every day or getting shopify or whatever business on shopify, so rewards programs combined with those flows has what we seen to have worked really, really well.

And having fun incentives in your rewards program where they are getting rewards for their purchases , getting rewards for liking your pages on social media, I like to really give good rewards incentives for them leaving reviews and especially if they leave photos with their reviews because then you can use those reviews and UGC that they upload in your email campaigns that helps to get more sales and also it just helps create community because people are seeing other people, they start to go like oh that person looks like me or it’s a photo inside their house and their kitchen kind of looks like my kitchen that resonates with people.

So doing those two things and also having tiers to those rewards program as that way people who are becoming better customers are always being shown extra love so for example in post purchase flows when someone makes the first purchase they get one version of that email, when they make the second purchase we are showing them more love and when they get to that third purchase now we are of course celebrating them. That’s just another part of it, we are making sure as they become a better customer they actually feel like they are a better customer and they feel like they are getting better treatment because they are getting better treatment and so doing all those things in combination that’s what gets people on you an what’s cool is that sometimes when I am on the Facebook groups of businesses that we work with and seeing people talk about the emails and seeing people like basically like doing the thing that where they complain but they are having fun with how much money they spend with the brand and say like “shut up and take my money” or I had to justify buying another bla, bla whatever. But seeing that people are having fun and actually like they are having fun together continuing to buy more and more products, it’s kind of a circle thing of a making it fun to stick around and be a long term customer.

Jaryd Krause:

So cool. I like the idea of when we do a lot is focusing on the people that are already interested, focusing on the people that are already bought and are just over delivering and it increases the customer life time value and customer retention and that’s where the real, people would think I might be leaving money on the table if I am not doing that but that’s cool.

Money is cool there and you can make more money by focusing on that but what you are really doing is helping people have a better life with your products and your services and that’s where real value for them comes in when they become hooked as in whatever you guys do it’s going to make my life better, whatever product you bring in is going to make my life better and that’s where the real value in business where is see it. SO yea Kyle thanks for coming on and dropping some bombs, it’s been real fun to chat. Where can we send people to check more about what you are doing?

Kyle Stout:

Yes you can find me anywhere on Elevate and Scale and my YouTube channel is where I am putting my most content right now.

Jaryd Krause:

Bring it on. Check out his YouTube channel guys, we will put links to all that in the show notes. Everybody thanks for listening and if you know somebody who has an online business, do share this podcast with them. Selfishly it helps Kyle and me get in front of more people and help more people but you are going to be helping that person that has a business understand more about email marketing which is going to help them help more people. So thanks for listening guys and see you soon.

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We help people buy established profit generating online businesses so the can replace their income and spend more time doing what they love with the people they love.


Jaryd Krause is a serial entrepreneur who helps people buy online businesses so they can spend more time doing what they love with who they love. He’s helped people buy and scale sites all the way up to 8 figures – from eCommerce to content websites. He spends his time surfing and traveling, and his biggest goals are around making a real tangible impact on people’s lives. 

Resource Links:

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Sell your business to us herehttps://www.buyingonlinebusinesses.co/sellyourbusiness

Active Campaign (Email Software Provider) –  https://bit.ly/3DCwYQH


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