Stop Renting Your Audience: Build an Email List That Converts | Kyle Stout

Your audience may be one of your business’s most valuable assets—but if it exists only on LinkedIn, Facebook or another social platform, you do not truly control it.

In this episode, Peter Boolkah speaks with Kyle Stout, founder of email and SMS marketing agency Elevate & Scale, about building an email list that creates measurable sales rather than becoming another neglected marketing database.

Kyle explains why email remains a powerful owned channel, how to attract the right subscribers and why purchasing email data can damage both trust and deliverability.

They explore how to nurture and sell at the same time, segment subscribers according to engagement, reactivate dormant contacts and build a straightforward automated funnel without creating an overwhelming marketing operation.

You’ll discover:

• Why social followers and connections are rented audiences
• How to create an effective lead magnet for your ideal customer
• Why purchasing email lists can damage your domain reputation
• How segmentation protects engagement and deliverability
• Why nurturing does not mean postponing every sales conversation
• How to decide the frequency of an automated email sequence
• A practical approach to re-engaging dormant subscribers
• Why click-throughs and sales matter more than vanity metrics
• How AI can support email research, testing and content creation
• Why every email needs a genuine reason to appear in the recipient’s inbox
• The three components of a complete email-marketing system

For founders, the wider lesson is important: a properly built email system is not merely a promotional tool. It is an owned business asset that reduces dependence on social algorithms, the founder’s personal reach and constant manual follow-up.

ARCHIVE NOTE

This conversation was recorded in 2023. Email-consent rules, privacy technology, artificial intelligence and sender requirements continue to change. Check the current legal and technical requirements relevant to your location and email provider before applying specific implementation advice.

CONNECT WITH KYLE STOUT

Website: https://www.elevateandscale.com/

LinkedIn: https://www.linkedin.com/in/kyle-stout-6804a117

Company LinkedIn: https://www.linkedin.com/company/elevate-scale

CONNECT WITH PETER BOOLKAH

Website: https://www.boolkah.com
LinkedIn: https://www.linkedin.com/in/boolkah
Instagram: https://www.instagram.com/pboolkah/
Facebook: https://www.facebook.com/Boolkah
X: https://twitter.com/boolkah

ABOUT PETER BOOLKAH

Peter Boolkah is a business coach, author and speaker who has spent more than 20 years helping business owners build stronger, more valuable businesses that do not depend on them for everything.

He is the creator of The Hamster Wheel Trap® and author of Your Business Sucks: Build a Business That Works Without Destroying Your Life.

Peter works with founders and leadership teams on the issues that ultimately determine whether a business creates freedom or becomes another job: leadership, founder dependency, people, profit, execution, scaling, exit readiness and enterprise value.

His approach is direct, practical and built around one simple question:

Do you own the business, or does the business own you?

Learn more at https://www.boolkah.com

Transcript

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[00:10] Peter Boolkah:

Hi, Peter Boolkah here, and welcome to today’s edition of The Transition Guy. Joining me today in the studio is Kyle Stout, who is founder and CEO of Elevate & Scale, a leading email-marketing agency. Welcome, Kyle.

[00:27] Kyle Stout:

Thank you for having me.

[00:29] Peter Boolkah:

Email marketing—what an interesting subject. Many people say that email marketing is dead because there have been so many spammy emails. People who try to do email marketing really don’t get anywhere fast.

Do you believe that’s the case—that email marketing is dead? You’re going to say no because you have an email-marketing agency, but why do you believe email marketing is still a valid strategy?

[01:01] Kyle Stout:

I would say the main thing it really comes down to is that email marketing allows you to have a direct line of communication with your leads and customers on a platform that you own and control.

While we’ve had all these other exciting marketing and sales channels emerge over the last ten years—and there are definitely things you should be doing—I’m not going to sit here and say email marketing is the only thing or the most important thing. I believe in having a cohesive strategy.

But there’s a certain strength that comes with email marketing because you’re able to own the data. You own the email list, so you can take it and move it to other platforms.

If you need to get a message out to people, you can always reach them directly in their inbox. If you’re on social media or running advertisements, you’re at the mercy of the algorithms. A lot of people who follow you might not always see the content you post.

[01:57] Peter Boolkah:

That’s an interesting point you raise, Kyle.

Is there a danger with all these exciting platforms—whether Facebook, LinkedIn or various others—that people have become lazy with their databases? Have they become accustomed to holding data on platforms they don’t own, where they can’t control its visibility?

LinkedIn is a great example. It’s fantastic having all these connections, but LinkedIn can cancel your account at any given time. You also don’t get much in the way of statistics showing how much of your network truly sees your content or who those people are.

[02:42] Kyle Stout:

Yes. This is something I see very often. It’s actually one of my favourite scenarios when a new client signs up.

Let’s say they’ve had great success with social media and are generating lots of sales from social media and other channels, but they haven’t done any email marketing. They’ve got this whole list of buyers. As long as the list is somewhat warm, I know we’re going to be able to do a lot with it in a short amount of time.

A lot of the time, it comes down to the founder or whoever is leading marketing. Everyone has natural skill sets. They might naturally have done really well on social media. Perhaps the business was initially built through their personal and professional network because they had the right combination of people and knew how to define their offer for them.

But that skill set didn’t translate into email marketing, so they haven’t had success with it. That’s pretty common.

As you mentioned, there are many advantages to adding email marketing into the mix—not only increasing sales but also the insights you gain.

When you put out emails and test different offers, different ways of positioning those offers or different groups within your customer base, you start learning much more about those people.

What are they actually engaging with? Which emails get them to click through, and what do they buy? You can see the specific products they purchase after clicking through an email.

Sometimes you’ll promote one product, get a large number of clicks and conversions and think you did brilliantly. Then you look at the insights and discover that, although you did well, people were actually buying a completely different product that you didn’t mention.

What you successfully did was get them onto the website. You can take that information and say, “We need to create more emails about this other product. There’s clearly demand here that we aren’t tapping into.”

If you have an “always be testing” attitude as a marketer and treat every email as a potential test, you don’t have to worry about every email being a home run. You can take what you learn, build on it and incorporate it into the strategy going forward.

[05:05] Peter Boolkah:

I think you’re absolutely right. This also assumes that the database you have is warm, clean and not trashy.

One of the conversations I’ve heard concerns the introduction of GDPR in the European Union. People are quite scared to harvest data from LinkedIn or Facebook because the way they obtain that data might not comply with GDPR or have the permission of the actual owner.

What strategies would you suggest people use in their businesses to start building a clean database that they can market to?

[06:11] Kyle Stout:

You need to be upfront and create some kind of offer or lead magnet—something that gets people onto your email list.

Simply having an email list and saying, “We’re going to give you exclusive content,” isn’t compelling enough. You want to have a free offer.

If you’re a product business, it could be as simple as creating a coupon code that people receive for signing up. It could be free shipping with a purchase or a free gift with purchase.

If you sell services, it could be some kind of free training or a PDF. If you’re selling services, I recommend making the lead magnet quick and actionable—something they can act upon immediately.

An important consideration when building a list of the right people is the ideal customer you’re targeting with the free offer.

Take a business such as mine, where I sell a service to people who need email marketing. If all my free offers are about learning how to do email marketing, those people often aren’t my ideal customers. My ideal customers don’t want to do it themselves; they want to hire somebody else.

They’re looking for insights and high-level strategies: what they need to know and why those things are important. I don’t go into too much detail about how to do everything, because that will attract other email marketers or people working in marketing departments who are simply trying to improve their email marketing and obtain free tools.

That’s something to consider.

The best way is to be upfront, create an offer and promote it often. If you’re on LinkedIn, Facebook or somewhere else, you want to move as many people as possible from those channels onto your email list by creating posts about your free offer.

[07:57] Peter Boolkah:

Okay, and that’s really stage one.

[08:00] Kyle Stout:

Exactly. You’ve got to start somewhere and build the list somehow, so you need something that gets people onto it.

As you said, when you pull people’s email addresses from different databases, it isn’t that the strategy can’t work. You just need to understand that most people don’t like it. You aren’t dealing with a particularly receptive audience.

It’s much better when you’re dealing with people who consciously chose to join your email list. They might become annoyed with the emails at some point, but at least they know they signed up. If they don’t want them any more, they can unsubscribe.

[08:38] Peter Boolkah:

Which is fair.

[08:40] Kyle Stout:

Exactly.

[08:42] Peter Boolkah:

So it’s about building the database first: obtain the right data, put forward a compelling offer and get people to subscribe.

How do you feel about buying data? There used to be a very large marketplace—perhaps five years ago—where people sold copious amounts of data and other people bought it.

Do you think there is still a marketplace for buying data today?

[09:18] Kyle Stout:

There’s probably still a place for it in other sales and marketing channels, although I don’t know enough about those to speak to them.

I know some people still do it for online advertising—for example, obtaining targeted databases and using those to create lookalike audiences.

For email marketing, however, I really don’t recommend it because I haven’t seen it work particularly well most of the time.

The data often isn’t as good as it appears. There can be many invalid addresses or addresses that people no longer use. Even if they are valid, those people signed up for something else that might be related to what you sell, but they didn’t sign up for your company.

You start by rubbing people the wrong way. It isn’t impossible for it to work, but it will be a much bigger uphill battle. It also creates problems people don’t anticipate.

Everyone anticipates that sending unsolicited emails might annoy the recipients. But because there are invalid and unused addresses, it can also affect your domain’s reputation.

Your emails may start going to spam or failing to reach the inbox because you’re receiving negative engagement from unresponsive or invalid addresses. Gmail and the other inbox providers make note of that. It’s seen as untrustworthy behaviour, so they’re less likely to deliver your emails—even to people who genuinely signed up for your list.

One strategy people use if they go down that path is creating a separate domain that’s completely different from their main domain. They send from that domain so they don’t risk damaging the main one. Once people engage or opt in, they might move them across to the other domain.

That’s a more advanced strategy if you really want to pursue that path.

[11:34] Peter Boolkah:

But surely that is simply circumventing the real problem. Don’t engage in trashy behaviour and you’ve got nothing to worry about.

[11:43] Kyle Stout:

Exactly.

[11:44] Peter Boolkah:

It’s interesting that Google and the other providers are taking note.

I’ve noticed that many emails I receive go straight into my spam folder. I wondered whether that was caused by a setting I had created, but from what you’re saying, it probably isn’t.

[12:08] Kyle Stout:

There are many possible reasons. It could be the content, certain words, the words contained in links or having too many links. There are many different things that spammy email marketers do with which Gmail is very familiar.

Those are the more obvious factors. But, as you said, people have often been too aggressive with their email marketing and sent to too many unengaged recipients. Their deliverability has taken a major hit.

They could have genuinely good-quality content in their emails. I’m sure that when you look in your junk folder, you see emails from lists to which you’re subscribed and from which you haven’t unsubscribed.

[12:55] Peter Boolkah:

Absolutely.

[12:56] Kyle Stout:

When that happens, assuming there isn’t any questionable content in the emails, it’s usually because they have been receiving too little engagement from other emails they’ve sent. Their domain has developed a reputation problem with the inbox providers.

It isn’t always caused by deliberately spammy people. It can inadvertently happen to people who aren’t being thoughtful enough about how they run their campaigns.

[13:21] Peter Boolkah:

Kyle, is there a way to check your reputation score as a domain?

[13:30] Kyle Stout:

Yes. There are all kinds of tools.

Google has tools for checking the technical configuration of your domain. The first consideration is making sure the domain has been set up correctly. Those are easy things to fix.

There are other tools, which are usually paid. One is GlockApps and another is Email on Acid. There are now many tools like those.

They can give you a complete report showing whether your email landed in the inbox, promotions folder or junk folder, and how often. They can also show which inbox providers are affected. Is it only happening in Gmail and not Yahoo, for example?

They can tell you which elements of your email triggered a warning and whether you’re on any blacklists or your domain has been blocked.

If you’ve suddenly seen a major drop in engagement and suspect that you’re having deliverability problems, even though you haven’t changed your content very much, I would recommend signing up for one of those tools—even if only for a month.

Start testing by sending your emails through the tool first, then make a note of the changes you need to make.

People sometimes make this sound like a huge problem, but you can turn it around in a month or two. It isn’t necessarily a six-month process.

[14:58] Peter Boolkah:

Okay, so it isn’t as big a jail as people might think.

[15:02] Kyle Stout:

No. There are extreme cases, of course, but often it’s simply a matter of setting your domain up correctly. There might be errors in its configuration.

Once you’re on the naughty list with the inbox providers, they’ll be stricter about those other domain issues.

You fix those things, perhaps take a break from sending for a while and test to ensure that your emails are compliant. Then you start sending to smaller groups of people and gradually warm the domain back up.

You could do that over the course of one to three months, depending on how bad the situation is.

[15:42] Peter Boolkah:

You do raise the point that, if you want to be a successful, serious and professional email marketer, there’s an argument for obtaining these tools from the outset so that you never fall foul.

[15:58] Kyle Stout:

Exactly. To me, the best approach is prevention.

That means generating email addresses from people who actually want to opt in. You send them content that aligns with the things you know they care about, so you put thought and effort into the content from the beginning.

It’s then about protecting those engagement metrics as you go along. If you start sending more frequently and notice a significant drop in your opens and clicks, reduce the frequency.

It doesn’t have to be drastic. A few bad emails don’t necessarily cause permanent damage. It’s flexible, and you can experiment with it.

One thing I highly recommend as part of an ongoing campaign strategy is creating segments. Segmentation allows you to create different groups within the list and send to those segments instead of sending every email to every person.

That will help you maintain higher open and click rates. When you consistently have good engagement, the chances of suffering deliverability problems fall considerably.

[17:15] Peter Boolkah:

Now it’s starting to sound like a really sensible strategy.

[17:20] Kyle Stout:

If you have a very small list, you obviously won’t need to do much segmentation because there aren’t enough people to create those groups. It’s something you build into the strategy as you progress.

It always comes back to the quality of the content, but as you grow, you want to start doing this.

Some of the first segmentation groups I create are engagement-based segments. I might create 30-day, 60-day and 90-day engaged groups.

In the 30-day group, for example, people have opened or clicked an email during the previous 30 days. I also like to include people who have visited the website during that period.

When we plan campaigns for the most engaged people, that 30-day group receives most of the emails.

The people who don’t fall within the 30-, 60- or 90-day time frames haven’t opened or clicked an email in more than three months. We don’t send all the regular emails to them. We only email them when there’s a new product launch, a major promotion or something else that is new and exciting.

Think about the mindset of somebody who has stopped engaging but hasn’t unsubscribed. The fact that they haven’t opened the emails doesn’t necessarily mean they never want to hear from you again. They might no longer have been in the market or simply didn’t need anything from you for a while.

When you have something new and exciting, those people might still be interested, particularly if they’re past customers and you’ve already built trust with them.

You can create segments according to the products people have purchased, their interests and factors such as gender, age or location. Age can be difficult unless you have a way to collect it.

You then craft content for that particular segment. The content becomes much more personalised because you’ve gone beyond simply creating a good offer and good content. You’ve tailored the message to that group.

If they have previously shown interest in a product, you can mention the product they purchased or viewed and connect it to the product or service you’re currently offering.

[19:39] Peter Boolkah:

What types of content are most effective in a nurturing campaign? How do you balance informative content with promotional messages?

[19:54] Kyle Stout:

I want to discuss nurturing in two ways.

There’s a strategy that has existed for the last ten years in which you get people to join the list, nurture them for a long time and only then present an offer and start selling.

That worked for a long time. What I find works better is doing both at the same time.

People have so many things competing for their attention that they need to make decisions quickly. Some people are ready to buy immediately. That may be why they signed up.

Most people—particularly in the business-to-business space—understand what you’re doing when you put out a free offer. They want the free thing you’re promoting, but they know that, in exchange, this is your opportunity to market to them.

If someone signs up, they’re saying that they’re open to being marketed to.

I don’t think it’s better to provide value exclusively for a long period before you begin to sell. I prefer a combination.

Perhaps two-thirds of an email provides value, while the bottom third uses a natural transition from that value into an offer.

For nurturing content in general—whether it’s a welcome series for a new subscriber or a long-term sequence—I think about all their questions, concerns and objections. Those are important things to discuss and educate them about, particularly when they’re new.

For ongoing nurturing, think about the lifestyle they’re trying to live and how your product or service connects with it. What are their bigger goals? What’s the larger picture, and how does your product or service fit into it?

If you sell a fitness product or supplements, for example, you could give them fundamental information about diet, following an exercise programme or developing the right mindset, and then connect that information to the product.

The point is to make the content useful, insightful or entertaining enough that, even if they aren’t ready to buy today, they think it was worth opening the email and will continue opening future messages.

If you achieve that, they’ll be more likely to buy from you when they are back in the market because they’ve continued engaging with you.

[22:33] Peter Boolkah:

That leads me to another question. How long should a typical nurturing flow last? What is the optimal frequency for sending nurturing emails without overwhelming or pissing off a potential customer?

[22:49] Kyle Stout:

The answer to both questions is that it depends. I’ll go into more detail because I know that’s the worst answer ever!

There isn’t one golden rule for every business.

I like to email more frequently early on. If somebody has just signed up, I might email them every day for the first three or four days. I might then space the messages out so that they arrive every two, three, four or five days. After a while, it might move to once a week.

You’re initially making an educated guess. You decide what to do next by looking at the metrics.

Go through the emails in the series and identify where engagement falls away. It could be caused by the content of that email, in which case you need to test different content.

But suppose engagement falls off a cliff after email four. Perhaps you need more time between emails three and four, and between four and five.

You can review the metrics in these automated flows once a month. I like to track them in a spreadsheet.

If you make a change, note what you changed. Did you alter the email’s content or the time delay between messages?

The following month, examine the metrics again and see how the change affected opens and clicks. It’s a continual process of testing.

[24:20] Peter Boolkah:

Testing and measuring are clearly important.

Are there any good, intuitive AI tools into which you can feed that information—tools that analyse it and suggest where changes might be needed? Or are we not quite there yet, meaning it still needs to be a manual process using something such as Excel?

[24:44] Kyle Stout:

I haven’t used any tools that can do that automatically. You can, however, obtain insights by giving the information to a tool such as ChatGPT.

Don’t expect the answers to be groundbreaking. It’s about obtaining ideas you hadn’t previously considered.

You can tell it that you have an email sequence, explain what you’ve done and how many emails it contains, give it the metrics and identify where engagement dropped.

You could ask it to suggest new email topics to replace an underperforming message, or to recommend a different frequency.

It will give you ideas, but you still need to test them. I wouldn’t treat its answer as the final answer. I would use it as a way to generate more ideas for whatever I’m working on.

If you do this work frequently and continually work with the same emails, you become so close to them that you can run out of new ways to discuss the same subject.

That’s where AI can be helpful, providing ideas and angles you hadn’t considered.

[25:57] Peter Boolkah:

That’s a fair point.

I was thinking about time-challenged business owners. Not everybody has the funds to create a large marketing department, particularly an early-stage business in perhaps its first four years.

Email marketing is probably critical for those companies, especially once they’ve built a database, but they don’t necessarily have the time to analyse all these insights manually.

[26:35] Kyle Stout:

If you’re an early-stage start-up, keep it simple. You don’t need all these advanced automations.

Have one main funnel through which you push people. That doesn’t mean you can’t send other emails, but you should have one main funnel to which you pay close attention.

It doesn’t require constant dedication. If you can set aside one hour each month, you can do this process. It’s really about committing to it.

We’re all busy. This is one of those things that’s easy to postpone until the next day, then the next week and so on. You have to put it into your calendar and set aside the time.

One useful development is that many email tools can now automate A/B testing and automatically choose a winner after a certain point. Those tools have improved considerably.

But I still recommend going in at least once a month and checking everything.

If you have a simple funnel with fewer than ten emails, creating it will take some time, but managing it once a month isn’t as big a burden as it might initially sound.

[27:52] Peter Boolkah:

It can sound overwhelming during the initial stages when you’re setting it up and preparing everything.

You’ve spoken about email sequencing and testing to determine the appropriate frequency. You also mentioned people who have become disengaged.

They’re still on the email list and haven’t unsubscribed, but they no longer engage. What is your preferred strategy for getting them active again?

[28:26] Kyle Stout:

First, I like to give them a break.

Going back to the segmentation strategy, if they go beyond 60 or 90 days without engaging, I give them some time away.

We develop habits of automatically archiving or deleting emails from certain people or brands because we lost interest at some point. Once that habit develops, every time the email appears in the inbox, we automatically delete or archive it again.

You want your email appearing in their inbox to become a novel experience again. That means giving them a break.

If you can then create a special offer specifically for people who haven’t engaged recently, that’s often the best approach. Not everyone will want to offer a special discount or free gift, but you can still give them a break and then reappear later.

I might stop emailing somebody regularly once they pass the 60-day point and then create an automation that triggers at 90 or 120 days.

When you return, show up with something exciting. It might be an offer, a promotion or something related to a previous purchase.

The messaging can be fun: “We haven’t heard from you in a while,” or, “You haven’t heard from us in a while.”

Acknowledge the fact that you haven’t emailed them and explain that you’re returning because you have something exciting for them.

You might be surprised how many people re-engage. They might make a purchase or, because they engaged with that message, start receiving the other emails again. They return to the regular rotation and begin opening and clicking.

[30:30] Peter Boolkah:

It’s important to include a planned break rather than continually emailing people and risking being blacklisted.

How negatively affected are campaigns during holiday periods when people have automatic replies saying that they’re on holiday? Is that something marketers need to consider?

[30:58] Kyle Stout:

No. In fact, Black Friday and Cyber Monday are the one period of the year when we take our normal rules and throw them out of the window. We say, “Send this to everybody on the list.”

Sometimes a company wants to create a particular offer for a group such as its VIP customers, in which case we create exclusions and manage that separately.

But for the large offers during those holiday periods, we go after everybody and become more aggressive. Because we have been so careful throughout the rest of the year, we haven’t seen any negative impact from doing that.

[31:40] Peter Boolkah:

Automatic responders don’t damage your trust score with email providers?

[31:46] Kyle Stout:

Not that I’ve seen. I’ve never seen an impact significant enough to be a concern.

[31:48] Peter Boolkah:

That’s something I had always considered. If I receive 30 or 40 out-of-office responses, does the provider think the email isn’t getting through and put the domain onto a blacklist?

[32:07] Kyle Stout:

No, because the person does receive the email.

What’s interesting—and I would need to investigate this because I don’t want to give you the wrong answer—is that they haven’t opened or clicked the email, but their account has replied to it.

In general, a reply to an email is considered a much higher-value engagement signal by the inbox providers.

If somebody opens your email, that’s good. If they click or buy, that’s great. If they reply, that’s like somebody on social media liking, commenting on and sharing a post.

But I can’t say for certain whether the inbox provider treats an automatic reply in the same way as a manual reply.

[33:05] Peter Boolkah:

That could be interesting. If it counts as a positive response, you would want to double down during the holidays.

[33:12] Kyle Stout:

I’ve never investigated that specific question, but I’ll have to look into it.

[33:17] Peter Boolkah:

What do you think are the key elements of an effective marketing email in terms of its content, design and call to action?

[33:26] Kyle Stout:

For me, the most important thing is understanding your ideal client or customer—their wants and needs—and speaking specifically to them.

We’re often too general with our messaging because we’re trying to please everybody.

If you’re using segmentation or know that you’re targeting a particular part of the market, make a point of speaking specifically to that group.

As far as length is concerned, it depends on what works for your business. Both short and long emails can work.

In general, however, use shorter paragraphs and sentences. Make it easy for people to skim the email.

Regardless of how much work you put into writing an amazing email, most people won’t read the entire thing. They’ll read the headline, the call-to-action button or link and, if you have one at the bottom, the postscript.

People tend to read those elements first. If they like what they see, they’ll go back and read the email.

You don’t want to write lengthy essays. Think about making the copy short, punchy and effective.

[34:44] Peter Boolkah:

That makes complete sense. Which metrics do you think are most important for measuring the success of an email-marketing campaign?

[34:53] Kyle Stout:

For business owners, it ultimately comes down to sales.

Open rates are the easiest thing to inflate. It’s easy to trick people into opening an email, but if you do that, nothing much happens. You have to deliver on the subject line. You can’t simply use clickbait to get people to open.

People are very concerned with open rate, but I would consider that more of a vanity metric in email marketing.

Sales remain the priority, but the metric that’s consistently most useful is probably the click rate.

It’s much harder to achieve a good click rate than a good open rate. When your list stops engaging with your emails, you’ll see click rates fall before open rates.

Click rate matters because we’re trying to generate sales. If people don’t click through, they aren’t going to buy.

It isn’t always about selling. You might be trying to get people to consume content by sending them to a podcast, blog, video or something else. If they don’t click the link, they don’t see the thing you put all that work into creating.

Click rate can tell you what’s likely to happen next. When click rates start falling, revenue often follows, although it might not happen immediately.

Having said that, some businesses don’t have particularly high click rates but still generate considerable revenue from email because they have very large lists.

Ultimately, the reason people use email marketing is that they want a consistent, reliable sales channel for the business.

[36:48] Peter Boolkah:

You don’t want to fall into the trap of patting yourself on the back because you have amazing opens and clicks if you aren’t achieving the main goal you set out to accomplish.

It’s one of the challenges around social media, where people focus heavily on vanity metrics. To your point, the ultimate return on investment is sales.

[37:11] Kyle Stout:

Exactly.

[37:14] Peter Boolkah:

You’ve been in this industry for a long time. How do you see the future of email marketing evolving, particularly with emerging technologies such as artificial intelligence and machine learning?

[37:28] Kyle Stout:

I don’t think we’re close to this yet, and I haven’t seen any tools promising to do it, but I believe we’ll eventually have fully automated email marketing produced by AI.

Suppose you decide to make an announcement, launch a product or offer a promotion. You might still choose the email’s subject—or at least have the ability to do so—but your email service provider’s AI would write the copy and create the design.

It could also take the data it knows about each contact and personalise the email for the individual recipient.

At the moment, we use segmentation. We research target customers and use that segmentation to personalise the content further. But we’re still dealing with thousands of people within each group and don’t know each person individually.

Online tools know the websites we visit and the things we purchase. I think we’ll reach a point where people receive individually personalised emails that show them the exact content they want and present the product in the way most persuasive to them personally.

[38:54] Peter Boolkah:

Do you honestly believe AI will evolve to that point? As you said, it doesn’t do that at the moment. Will it be able to provide context and not merely content?

[39:05] Kyle Stout:

I do.

For example, if I want AI to produce some email copy, I currently do much of the preparation manually.

Because I put a great deal of work into defining the messaging strategy for every business I work with, I don’t simply prompt it to write an email about a particular topic.

I tell it to write an email from this company. I give it the subject, the type of email—whether it’s promotional, value-driven or something else—and background information about the company.

I provide psychographic information about the target customers and potential angles it could take, including the things it should emphasise. I put all that information into the prompt.

[39:48] Peter Boolkah:

So you’re loading all the context upfront.

[39:51] Kyle Stout:

Exactly.

The AI is relying on me to obtain all that information—some manually and some from data—and give it to the tool.

But what happens when the AI tool is built directly into Klaviyo, the email service provider we use frequently, and already has all the previous customer information?

Klaviyo is a major email service provider and probably the leading tool for ecommerce companies.

On the back end, these same people could be on hundreds of different email lists. Klaviyo could know that individual’s purchase history across hundreds of businesses, as well as the products and content they have viewed from hundreds of different companies.

It could take all that information and use it to determine the email’s messaging strategy.

With what we currently have, I can see how it could be done. I just don’t know of anybody working on it, whether a tool like that exists or how long it would take to get there. But that’s where I believe we’ll eventually arrive.

[41:05] Peter Boolkah:

That’s interesting.

[41:08] Kyle Stout:

It’s interesting—and it would put me out of a job!

[41:11] Peter Boolkah:

That’s the thing. We’re beginning to understand where it might be heading.

Some of it will be exciting for people, but it might become less exciting when it begins affecting their livelihood.

[41:25] Kyle Stout:

It’s definitely a strange time. There’s a great deal happening.

When people previously discussed AI and robots replacing jobs, everybody said they would first replace blue-collar workers and people doing manual labour. They thought creative professionals would never be replaced.

What we’ve seen is that AI moved into the creative space more quickly during the last year than it moved into the other spaces.

Think about all the AI tools connected with copywriting, design, music and video.

I don’t think the creativity of AI is anywhere close to human creativity. I also think there will always be a premium attached to human-created art because we’re human and connect with other humans.

I think we’ll always place a premium on knowing that creativity is difficult and that creating something original is hard. We’ll appreciate that.

But it’s very interesting, and I wonder how it will play out for everybody.

[42:32] Peter Boolkah:

I wonder whether it will replace humans or enable greater productivity, allowing humans to accomplish much more in the same amount of time by using the tools.

When the washing machine, microwave and dishwasher first appeared, I’m sure people had similar concerns. Those inventions changed the dynamics of many households.

Even today, washing doesn’t do itself, despite having many automated steps. Those appliances enabled people to free up time.

I wonder whether we’ll find a similar balance with AI—where it becomes an enabler but still requires human input.

[43:22] Kyle Stout:

That’s what I wonder as well, because I currently see it as a productivity enabler.

Although I have concerns about the bigger picture and AI’s effect upon life generally, I wouldn’t say that I’m afraid of it.

I see something that adds value and improves our productivity rather than something I currently feel threatened by. That doesn’t mean it won’t eventually replace us, but right now I see it helping productivity.

I also have a gut feeling that humans have always resisted change and innovation. Eventually, the innovation becomes integrated into our lives and we reach the point where we wonder why we would ever want to live without it.

[44:17] Peter Boolkah:

Which is where I see us heading.

[44:22] Peter Boolkah:

One final question. What do you think are some of the biggest email-marketing challenges facing businesses today, and what can they do to overcome them?

[44:32] Kyle Stout:

The most common thing people say to me—and the thing that stops them from doing email marketing or doing it frequently—is that they don’t know what to say.

When they sit down to create an email, they don’t know what to write.

Part of that is an underlying mindset. We all receive emails we don’t like. Emails can be annoying. We’re busy and don’t like receiving emails that aren’t useful or relevant to us.

When somebody sits down with that happening in the back of their mind, they’re already thinking, “I’m going to annoy people if I create this email.”

That blocks the creativity needed to produce something genuinely interesting.

I know I’ve said this repeatedly, but everything begins with researching your ideal customers and understanding their pain points, dreams and aspirations.

You need to identify subjects that will interest them. Focus more upon who you’re selling to than what you’re selling.

When you adopt that mindset, it will be reflected in the copy and design because you’re thinking about the recipient. You aren’t merely thinking, “What’s in this for me?” You’re considering what’s in it for them.

Create a natural transition from that valuable content into what you’re selling. It doesn’t always have to be educational value. It could be entertaining or funny.

The thing I always come back to is that you need a reason to appear in their inbox.

Before creating an email, ask yourself whether it deserves to be sent. Will it be sufficiently interesting that the recipient opens it and doesn’t regret doing so?

[46:27] Peter Boolkah:

You make it sound simple, but I know you have a background in copywriting.

Most business owners haven’t started their businesses with that kind of background. They’ll be thinking, “That’s easier said than done.”

You’ve mentioned clients who work with you. What does working with you look like?

[46:47] Kyle Stout:

Do you mean what’s involved from their side compared with ours?

[46:52] Peter Boolkah:

Yes. What do you offer, and how does it work for your clients?

[46:56] Kyle Stout:

It can be as hands-off as they want it to be.

Most of the time, we provide complete management. We create the strategy, write the copy, produce the design, implement everything and undertake all the analysis.

Some people have ideas and input they want to provide. They might have a vision for their email marketing but don’t know how to execute it. We’re happy to work with them in those cases.

But many people say, “This isn’t my world. I don’t know anything about it and don’t want to deal with it.”

Particularly early in the relationship, I want to obtain insights from them.

What feedback do they receive? What do their customers really care about? If the product has ten benefits, which two or three benefits are mentioned repeatedly?

We then build topics around those things.

Returning to research and topic generation, I can also give somebody a process that uses AI to generate all these potential topics. That saves time on that part, although somebody still needs to create the actual email.

[48:05] Peter Boolkah:

So you have a comprehensive process, ranging from fully done-for-you to semi-done-for-you.

[48:14] Kyle Stout:

Exactly. We offer both.

We manage the opt-in forms that bring leads onto the list. We then manage all the automated emails, making sure that automated follow-up exists throughout the sales process.

The third part is the ongoing campaign activity.

Whether you do it yourself or hire somebody else, those are the three big components of email marketing that need to be managed:

The opt-in forms and list growth, the automated follow-up throughout the sales process and the ongoing campaigns.

[48:43] Peter Boolkah:

I’m sure plenty of people listening will be asking how they can contact you.

[48:50] Kyle Stout:

The best place is elevateandscale.com.

If you want to learn more about email marketing and access more content, YouTube is where I publish most frequently. The handle is also Elevate and Scale.

[49:07] Peter Boolkah:

Perfect. Thank you so much, Kyle. It’s been really interesting.

If you’ve enjoyed today’s episode and received great value from it, please make sure you like it because that helps us on YouTube. Subscribe so that you don’t miss future episodes, and share it with other people who could benefit because we want to get the word out.

If anything we discussed today resonated with you and you would like to talk about it in more detail, head over to boolkah.com and get in touch.

Kyle, you’ve been an amazing guest. Thank you so much for appearing on today’s episode.

[49:40] Kyle Stout:

Thank you so much for having me.

[49:42] Peter Boolkah:

It’s been a pleasure.

And remember: failing to learn is learning to fail.