The Evergreen Email System That Transformed My Business

Are you tired of the feast-famine cycle of traditional course launches? In 2020, I finally escaped this rollercoaster by developing what my good friend and mentor, Brennan Dunn calls the "Shadow Newsletter Strategy": a combination of evergreen content and dynamic personalization that has transformed my online course business.

This isn't just theory—it's a proven system I've used in my language learning business for over four years now. Since implementing this approach:

• My revenue became consistent month after month
• Customer satisfaction improved dramatically
• I eliminated the stress of launch deadlines
• My business runs smoothly whether I'm working or on vacation

In this article, I'll show you exactly how I built an email marketing system that generates sales consistently without the pressure of launches or aggressive marketing tactics.

What You'll Learn in This Guide:

• Why traditional course launches create feast-famine income cycles
• How the Shadow Newsletter Strategy creates consistent monthly sales
• The Dynamic PS technique for personalized email marketing at scale
• Step-by-step implementation of an evergreen sales system
• Results and lessons from four years of launch-free course sales

Why traditional course launches create feast-famine income cycles

I used to live in Australia. As a person from Europe what I missed the most was...

the seasons!

In theory, it sounds good to have a 9-month summer with a brief winter. But those winters in the uninsulated houses without proper heating sucked.

This is exactly what I don't miss in an online business. The summer-winter change. The feast-famine roller coaster. Yes, I'm looking at you launches.

I started doing online marketing in my Australian days back in 2009. Since then more than 15 years have passed and I have tried everything under the sun.

You know, the "best practices" that "gurus" preach.

You have to do payment plans.

Don't do discounts, because you will devalue your brand.

And mostly:

Launches work.

Scarcity works.

Yes, they do.

They also suck to manage, drain my life and come across very pushy.

What if my audience just doesn't like that?

What if I don't like that?

But I kept pushing along and implemented these "best practices" because "smarter people than me told me so".

These smarter people are also very different from me and my business.

For starters, 95% of them are in B2B.

My Business is in B2C (teaching people how to learn a language as opposed to teaching them the actual language). But I kept believing them. And their methods worked to some extent. This was bad because if they hadn't worked at all, it would have been easier to start doing something entirely different.

So I did launches.

Setting up the infrastructure, managing open carts, coupons, payments, support - just thinking about it makes me want to pop a Xanax.

"Yes, but then you can relax for 3-6 months." - they say.

Yes, which 6 months will be spent obsessively developing anxiety about the next bloody launch. Very relaxing. (It's not)

Why Course Launches Suck (And You Know It Too)

Hand to heart - you hate launches too.

Here are my top 4 reasons why I hate them:

Not predictable. A lot of businesses got caught with their pants around their ankles with Covid. If we base half our yearly revenue on a launch - and something happens, we are in the deep end of the water.

Stressful af. Setting up the infrastructure, managing emails, remarketing, payments, refunds, cart closes, deadlines, support tickets. No, thank you.

Pushy af. I like to think I'm a nice guy. But in order to sell, you "have to sell hard" (another guru gem). You know, like car salesmen from the 90s. Looking into the camera and screaming that "you won't find a better deal than this".

Complex. I want a simple system even at the expense of some revenue. It's fine to make less if I get to keep my (remaining) hair.

I always preferred evergreen sales, but the status quo said that I would get a bigger bang for the buck if I did launches.

That might be true - if the only variable in the equation is revenue.

As a business owner, I forgot something very important.

Myself.

I. Just. Hate. Launches.

So I'm ok with making less if my other criteria are fulfilled: business is predictable, not stressful, not pushy and not complex.

Great - it only took me a decade to realize that.

Problem was - I had no idea how to change that.

Funny enough that in the online marketing niche everyone and their mother in law tries to teach us how to make "six-figure businesses", yet, no one is talking about how to make 5 or even 4 figure businesses that are stress-free, hands-off and just a joy to manage.

If I had to choose between a 6-7 figure business with a cardiac arrest in the queue or a few thousand dollars a month on (almost) autopilot in a business that I actually enjoy managing - well, I'm gonna go for the second one.

The Email Dilemma

The best marketing channel is email - we all know that.

I love email. I treat my subscribers as friends. 99% of the time I reply to everyone on my list personally. So that is good. And I actually enjoy that.

With the boom of email marketing in the last few years, we have more tools and data we can handle. We can get really granular and we can personalize our emails to the last letter (and I'm not thinking of "Hey, %FIRSTNAME%" personalization).

Unfortunately, this brings unwanted complexity as well.

Just think about all the email sequences, link triggers, rules and automations and the unlimited permutations you can set up with your email software. My head is already spinning.

In theory, email is simple.

Sign up, I will send you useful stuff and hopefully one day, you'll opt for buying one of my products.

In practice, it's a shitshow of half-broken automations, temporary tags that were created years ago and you don't dare to delete them in fear of breaking something without you knowing it, rules but just as many exceptions and of course the total lack of documentation.

So Criteria no. 2 is not fulfilled.

Oh yeah, and let's not forget about breaking points where subscribers are just "pending" without us knowing it or overlapping emails where the subscriber gets carpet-bombed with our emails.

Criteria no. 3 is not fulfilled.

The Solution: An Evergreen System That Actually Works

The solution is simple:

Have an email sales system that:

Provides a ton of value upfront for the subscriber - also hands-off.

It pitches the subscriber only if and when they are ready to be pitched with the product that really serves them.

It is "set it and forget it" from the infrastructural point of view. I'm willing to frontload the work and spend 10x energy on it now if I don't have to think about faulty points, leaking buckets, angry subscribers, and mistimed product pitches.

The solution to the first part is called Shadow Newsletter. We will dive into this soon.

Note: Shadow Newsletter was first coined by my good friend and mentor,[](Brennan Dunn).

The solution to the second part is called an Offer Funnel and a Dynamic PS. We will also dive into these soon.

The solution to the third part is, well, barrels of coffee in the solitude of your office.

I can help you with the first two. Well, maybe with the third too.

How the Shadow Newsletter Strategy creates consistent monthly sales

This is a term my friend, Brennan Dunn coined, and I make no attempt to take credit for it.

I don't know about you, but I sure as hell hate the content treadmill. This is why I write maybe 2-4 new blog posts a year. I think I said what I knew about my topic in the first 10 years and I think it's ridiculous to see media companies regurgitating Top 5 Tips to Make Money Online posts just to "keep things fresh".

No, you don't need to keep it fresh.

You drown me in useless noise, dear content farms.

Today's content treadmill is no different from EZine Articles and article spinning back in 2011 (if you don't know what it is, I dare you to check it out on Youtube).

You woo me with quality and not freshness.

So a Shadow Newsletter is just your best writing that you don't have to optimize for SEO. It's for your valued subscribers.

It is for long term nurturing after you delivered your onboarding emails.

It is also something that is going out on a schedule - not just when you feel like it. Luckily, email software makes it easy to do this (an autoresponder). Why this is important is because a prospect might not be ready to engage with you at the given moment (for the sake of simplicity by engaging I mean buy your service/product) for various reasons. Their basement may have been flooded yesterday. They are interested in your product but their priorities are elsewhere. This is a prime example of why launches suck - if you miss that small window when life is just perfect for your subscriber to buy your product, well, they have to wait another 6 months.

And we all know that they won't.

The solution is simple: keep in touch with them. Period. Once a week is great. Our autoresponder will make sure that happens for a year (yep, you will need to write 52 value emails upfront. Yes, I know, you cringed. It's ok. I'll show you an easy way to do this later).

I'm sure you've heard the old adage - a prospect needs to see your product at least 7 times before they make a decision and purchase. You can't just spring a launch on a subscriber and expect good results. That is insulting to your audience. Criteria no. 3 wouldn't be fulfilled.

The Offer Funnel

An offer funnel is simply a path that you craft for each and every one of your subscribers based on their needs and what you know about them.

In other words: you show them what they should be doing next in order to move closer to their goals (which we happen to facilitate with our products and services).

What can these "next steps" be?

Reply to this email so we get to know each other a bit more

Go and read my free articles so you get the idea what my philosophy is about

Check out and maybe buy the introductory course that I think will help you reach your goal faster

Provide a testimonial

Just touch base

Help me spread the word of my business

Problem is - these are very different for every subscriber.

If your brother signed up to your email list, it may be fine to ask for a testimonial from him, but it would be awkward to ask him to reply to that email so you can get to know each other a bit more.

If a pregnant mom just found your site and signed up to your list to learn more about starting a business from home, it might be a stretch to pitch her a $9000 mastermind retreat right out of the gate.

So the offer funnel helps us determine on an individual level what is best for our subscribers. So criteria no. 3 is fulfilled. Not pushy. Great.

The Dynamic PS technique for personalized email marketing at scale

We will dig deep down. We want a personalized email that delivers value first but also helps our business too. And we want a template for this email so we can repeat it 52 times. We want simple, repeatable emails that deliver a ton of value and then softly ask for something in return at the end (by which time we already delivered that value and are in the position to do so).

This is why we break up the email into 2 living parts.

1. Value (the content of your email)
2. PS.

And here is the tricky part: we want them to live a separate life.

What is really important to understand: the Dynamic PS will vary not only on the email level, but on the subscriber level as well!

So my autoresponder sends out Email 1 on Tuesday and the content is about motivation. This is the same for everyone. But the PS is different for everyone based on our offer funnel logic (more on this later) - so they only see relevant things to them.

Say what?

How?

If your email provider uses a templating language (like Liquid in my provider, Kit's case) so that you can interact with their stack and connect that to the front end, you can change the email content on the user level.

This was a mouthful, so let's look at an analogy.

You have an opt-in box at the bottom of all your posts on your site. The call to action here is for the user to sign up to your email list.

Once they signed up, it's unnecessary to invite them to sign up (again), so the opt-in box can be turned into another call to action - for example, to check out your product's sales page. They get continuous exposure to your product every time they read a post of yours.

Let's go back to our Dynamic PS example.

Once a user has bought your Product A, then they won't see a PS that pitches that product - because that would be a waste of real estate, attention and their time. So we are considerate in our marketing. Instead, we can show them something different (maybe inviting them to give us a testimonial, or just have them engage with you, etc). All this is based on how you set up your offer funnel.

The good thing about a Dynamic PS is that it is REALLY dynamic. You can make it as pitchy as you want or as humble as you want. You can set up the offer funnel in a way that after they bought your Product A, they won't see a product pitch for months in the PS.

Also, we want to avoid fatigue - if we used the same copy to pitch the same thing, subscribers would develop "ad blindness" to them and just ignore them after they see them a few times.

Luckily our trusty Dynamic PS can handle as many products and as many different copy variations as we want (5 different copy for a given product or service is enough, 10 is plenty).

Real-World Examples of Dynamic PS

So let's get concrete after all these abstractions.

Examples of Dynamic PS (Not a copy to copy, ha!):

PRODUCT A, PITCH 1: Do you have a problem with PROBLEM A? Then you might be interested in my PRODUCT A. (And just link to the sales page)

PRODUCT A, PITCH 2: 5 years ago I had PROBLEM A, now I don't. I summed up my experiences and how I solved them in COURSE A.

PRODUCT B, PITCH 1: Ready to learn more about Problem B? My PRODUCT B helps you with exactly that.

PRODUCT B, PITCH 2: PROBLEM B is frustrating. This is exactly why I spent 2 years solving that - here are the cliff notes (link to PRODUCT B).

ASKING FOR TESTIMONIAL, PITCH 1: Has my content helped you in any way lately? If so, I'd love to hear about it!

ASKING FOR TESTIMONIAL, PITCH 2: I hope my content helped you in the past weeks to reach your goal. If so, care to share it with me?

ASKING FOR SHARE, PITCH 1: If my content helped you, would you mind sharing it on social media so that my message can reach more people?

ASKING FOR SHARE, PITCH 2: Wonder how you can help me? Just share my stuff with your friends, it might help them too!

Now, the exact copy is of course up to you (and your brand).

So if a subscriber has bought Product A, they will NEVER ever see the first two items in the PS, because our business logic (offer funnel) will take care of that.

Every email that goes out to them (say, every Tuesday), will have in the PS either:

PRODUCT B - PITCH 1

PRODUCT B - PITCH 2

ASKING FOR TESTIMONIAL - PITCH 1

ASKING FOR TESTIMONIAL - PITCH 2

ASKING FOR SHARE - PITCH 1

ASKING FOR SHARE - PITCH 2

What happens if, say, after 3 months, the subscriber decides that they want your PRODUCT B?

Guess, what!

The next Tuesday, when your next Shadow Newsletter goes out, the system will randomly pick from these:

ASKING FOR TESTIMONIAL - PITCH 1

ASKING FOR TESTIMONIAL - PITCH 2

ASKING FOR SHARE - PITCH 1

ASKING FOR SHARE - PITCH 2

And insert them after your email content.

You never have to think about what and how to pitch.

Oh, yes. I almost forgot:

Be prepared for "thank you" emails - besides the nice, smooth revenue.

Here is my product sales breakdown before and after implementing the Shadow Newsletter with Dynamic PS:

Now this is what I call evergreen.

Am I going to buy a yacht to complement my (non-existent) beachside villa from these? Not likely.

Can it actually sustain me and my family's lifestyle while I enjoy managing the business and I get to focus on other pursuits as well?

Hell, yeah!

Step-by-step implementation of an evergreen sales system

What do we need to set up this system?

Interesting ideas and stories as a vehicle for the value email content -> 52 emails (a year of content for a subscriber)

Your products/services

5-10 different pitches for them (in a PS format)

An offer funnel design

An email provider that uses a templating language (like Liquid). Kit (formerly ConvertKit) and Drip are two of them.

An ass to sit on to write and implement all these (or some help)

Let's take them one by one:

Interesting ideas and stories for your value emails

Now, this is very much up to you and your business. You know best what works in your industry. The good news is that you don't have to think about how this will tie into the product pitch - as that is handled separately by the Dynamic PS and our offer funnel, remember?

One very important lesson I learned in my 15+ years of email marketing:

People don't need 24/7 hardcore tutorials delivered to them.

Isn't this a relief?

And you know why?

Because every great tutorial creates a bloody todo item on their list.

And they get frustrated by not having enough time to implement them. This turns into resentment and over weeks and months, they will just grow apart.

Solution?

Keep 'em light!

It's not an accident that we live in an edutainment era. Yes, people want to learn - but they also want to be entertained.

Guess what.

This is good for us too!

No need to spend 10+ hours on a tutorial for an email (remember the content treadmill?). You just need to make them change their mindset about a minor thing.

And those things will add up.

Hopefully, you already demonstrated your authority (and provided a boatload of value) by your onboarding emails.

My friend, Olly Richards does this brilliantly. Check him out here.

The tutorial content should be reserved for your course/product/service anyway.

Your emails should just spark interest in them and let people come to YOU when THEY want (this is why we are emailing them weekly, to keep us in their mind. And when the time is right, they will reach out to you and buy your service/product. Or not. But the odds are MUCH better). This is considerate marketing.

Here is a snippet from my Shadow Newsletter. I think the open rates and click rates are quite OK.

(As you can see, email 2's numbers are a lot lower than the others. I pasted an image straight from clipboard (as opposed to using the editor's uploader), that botched something in Kit's stack and inserted a link that was about 2 gazillion chars long. Long story short: the tracking pixel was not properly inserted into these emails, so those numbers are not real. Also, it provided a very bad user experience. Lesson? TEST EVERYTHING 20 times!)

Your products/services and their relation

It totally depends on your business and what you sell. If you have just one product, it's significantly easier. You write a few different PS that pitches it (so they see various pitches and don't get ad blindness) and you call it a day.

If you have multiple products then you have a bit more thinking to do.

Are your products horizontal or vertical?

The answer will determine how you design your offer funnel.

Vertical: You have an introductory (likely cheaper) product. Some call it a tripwire, some an intro product, it doesn't matter. Then the next product builds upon that (so ideally, your customer will buy your tripwire first, and then your more expensive offer, and then an even more expensive offer).

Horizontal: Your business is based around pain points that are not necessarily related and therefore can't really be stacked (like the vertical model).

My business is the latter. I teach other people how to learn a foreign language. My audience has various pain points that have nothing to do with each other. One person might be shy to speak, the other person is having problems with memorizing vocabulary, the third doesn't know how to start, etc.

5-10 different pitches for them (in a PS format)

This is self-explanatory. You just need to write the copy once, you'll set them and forget them. The more variation you use for a given product the less likely they will see the same one multiple times (aka. less chance to get bored of your pitches and more chance to hook them with a new angle).

It's worth having at least 2 copies for a product so you can rotate them, but the effort to write 5-10 is not that much more than the results they can yield. It's up to you.

An offer funnel design

Every subscriber has a custom field called "offered_products". If the subscriber buys any of my products this automation runs, and checks which product was bought and excludes that product from the offered product array (these are shorthands for my product names):

My business is horizontal, so I designed my offer funnel in a way that I pitch users all the products that they haven't bought from me randomly (and when the time is right and THEY want to, they will buy it).

On the implementation level it looks like this in Kit (formerly ConvertKit):

So if the user bought the product called SZMOK, their offered_product array will look like this:

I use these in the Dynamic PS to refer to their respective pitches.

An email provider that uses a templating language (like Liquid)

Kit (formerly ConvertKit) and Drip are two of them. I personally use Kit and have been using them since 2016. Kit is not cheap, but it's bootstrapped (which I extremely value). It's not perfect, but it's good enough.

An email template designed for Shadow Newsletters

This is the apex of this whole thing.

Your email provider probably allows you to design email templates - you know, you can have various headers, banners, and whatnot. But we are using a specific template just for our Shadow Newsletter and will inject all our code to dynamically generate the PS for every email and every user on the fly at render time (this is key to understand: personalization happens not only on email but on the user level).

Ultimately what we want is this to change:

The email template contains all the logic to:

You need to capture all the product pitch copies you want to use in the template. Here are two examples:

{% capture szmokl 40<strong>Ps:</strong> Pitch copy no. 1 goes here (obviously with a link)</a>{% endcapture %} 
{% capture szmok2 40<strong>ui:</strong> Pitch copy no. 2 goes here (obviously with a link)</a>{% endcapture %} 

Then:

Have a look at the subscriber's "offered_products" field and check what products are in there

Randomly picking one from the products they haven't purchased

Then check the corresponding pitches and randomly picking from them

(Note: I did not include my own PS copy, but they go before the code.)

Injecting that copy after our name:

Now obviously this might be different for your business, but you get the idea. The horizontal model in my opinion is a bit easier to implement, but I prefer mine (because it gives the subscriber the chance to see ALL my available products and pick the one that resonates with them at that given moment).

This is as close as we can get to being a great salesperson (only that this is all automated). This system is not perfect and could be better, but satisfies all my criteria above.

Nothing is stopping you from using this AND launches too - far from it! This system is very versatile.

(Note: I've already developed and tested fully personalized, evergreen launches that change every time the user sees them, keeping it fresh. Deadlines are authentic. More on this in an upcoming article).

And my readers are actually thanking me. It's bloody awesome.

In fact, my latest data from 2023-2024 shows even better results than when I first implemented this in 2020. My conversion rates have increased by [X]%, and the average revenue per subscriber has grown by [Y]%.

A bonus tip

It's childish, but I love it.

I hooked up my sales CRM (WooCommerce) with Push Bullet - so every time a sale happens, my phone gives out this ka-ching sound. This is the ultimate habit hack - I get motivated every time I hear this.

The Reality of Implementation

I'll be honest. It took me 3 weeks and dozens of hours to design the system, write all the copy, implement the business logic, code the liquid templates - and most of all: testing the whole shebang.

Email providers are not designed for this kind of "overclocking" and therefore not equipped with the right tools (a debugging system for starters) which is somewhat understandable. This is not their job. However, Brennan Dunn's testmyliquid.com was a HUGE help in this.

But for us, smart marketers, it's worth investing blood, sweat and tears into an evergreen system like this. Because we only have to do it once.

Yes, it hurts, but then it's awesome.

I can't stress how important testing is - as you could see from my own example, a lousy bug and an image turns into an endless link which results in very bad user experience.

But you know what?

The worst email response I got was "Do you know that your email looks weird?" - and I attribute this to the fact that this system helps to maintain a close relationship with my readers and they will just glance over a mistake like this once in a while.

Apart from the dozens of hours I sunk into implementing this system, I had to actually learn about these things - I went through Brennan's Mastering ConvertKit course 4 times at least, taking rigorous notes.

Want This System Without the Headache?

If you've read this far, you probably fall into one of two camps:

You're excited to implement this yourself (awesome!)

You love the concept but dread the technical implementation (I get it)

If you're in the second camp, I can help. Since 2020, I've refined this system and implemented it for multiple online course creators, helping them escape the launch cycle while maintaining steady revenue.

I'd love to hear your ideas on how you'd implement an evergreen soft pitching system like this - I hope this article gave you a solid idea. And if you ever need help, or you like my system but don't feel like setting it up yourself, or you are not a person who is comfortable with writing copy AND code - just send me an email here, I'd love to help you.