Jamie THE MARKETING NERD
Posted in   Business Strategies, Email Marketing   on   December 8, 2024 by  Jamie THE MARKETING NERD 0

What You Absolutely Need to Know About Email Marketing

Email advice from Ramit Sethi, Neville Medhora, Pat Flynn, and Me

Great email marketing will add top line revenue to your business. Full stop.

Everybody knows that email marketing is one of the highest ROI marketing channels you could possibly use. It is one of the best ways to grow your business.

Note: Check out Ramit’s amazing website for more no-nonsense marketing advice too!

Email marketing is a low cost, easy way to have a direct connection to your audience. Everyone’s focus is on getting more email subscribers, growing that list, but what happens to them after they’re there?

That’s what we’re going to talk about today, how to get value out of your list and build email systems that add revenue to your business.


How do I get email subscribers?

This is the question that’s probably at the top of your mind.

The easiest way to get subscribers on a low budget is by content marketing. I have talked about how to create content that is actually valuable before, so what I want to focus on today is a more advanced topic.

This technique is one that all of the big gurus use, most people with lists over 100,000 subscribers actually use it too. The easiest way to get new email subscribers through your content is by using something called a content upgrade (also sometimes called a lead magnet).

Think of a content upgrade as kind of a “bonus”. What you’re trying to do is create a PDF that compliments the content of your article, or otherwise adds more value to the article.

You’re going to dangle this goodie as the carrot to get your readers to join your list. So you’re going to want to make the content upgrade something they want.

How do you make content upgrades?

There are two main ways to do it:

First, you can create an extra resource or tool that truly “upgrades” the post. You can create checklists, infographics, or some type of easy to reference sheet based off of information in your article.

Here is an example of a content upgrade that I used in one of my client’s email autoresponders:

Do you see how I designed the checklist to be something the reader will want to print out and reference?

Content upgrades are usually PDFs, so that’s why I mention checklists and everything, but it doesn’t have to be. Your content upgrade could be videos or audio too — but you want to stick with something that can easily be delivered by an email marketing program.

The second thing you can try is a PDF download of the complete article.

This is a strategy that the awesome copywriter Neville Medhora uses on his own website. Of the people who initially click on the little book image at the bottom to download a PDF copy of the full article, 60–77% of them complete the form and join his list. Neville also says it is slightly under 10% opt-in rate across his website overall.

A “good” opt-in rate for a website is between 1–5%, although as you can see it’s possible to have even higher opt-in rates like 10% using targeted offers!


How does this content upgrade get to my readers?

Basically what you’re going to do is create a PDF, and set up an email opt-in. You can use really any email marketing tool like Mailchimp, or ConvertKit. In the earlier example, Neville Medhora uses Infusionsoft to deliver his PDFs.

You’ll want to Google “digital product deliver” + YOUR EMAIL MARKETING SERVICE. If you can attach a PDF to the email, you can set it up as an automated message that triggers “move to your main list” (where you send most of your announcements) when they click on the link (here’s what you’d do in Mailchimp for reference).

Now that you know how to get people on your email list, let’s talk about getting them to read your emails…


How do I get people to open my emails?

You’ve got them on your list! Great!

Say that the reader has opted in to your list. They’ve downloaded their content upgrade. Now your email marketing program will move them into your “main” automated email sequence. Or maybe onto your “announcements” list.

Now we need to talk about getting them to actually open your future emails.

The #1 most important thing in getting people to open or to read your emails is going to be understanding your market.

By getting clear on your audience’s wants, fears, pleasures, and needs you will be able to understand how to best present your information that it really resonates with them.

The best piece of advice I can give about writing subject lines is this:

State the benefit of the information you’re providing.

When you read articles about email subject line “best practices”, they’ll tell you to “Start your subject line with an action word!” and “State clearly what you want them to do!”

That’s all great advice, but that advice is not the whole picture because it sometimes leaves you with subject lines like this:

Click here to read my guide on watch care (let’s say the example is an ecommerce store who sells watches).

Yes it starts with an action word, and yes it’s relevant to a problem your target market has, but what do they get out of it?

What’s in it for them?

Like I said, that is a great start. What would make it even better is if the subject line framed the benefit the reader will get out of the email.

Instead of that, how about…

Click here to read my guide on watch care and make your expensive jewelry last a lifetime.

I hope you see the difference now.

Really detailed articles (or videos) about even general topics like “How to take care of your watch” can be very successful when you present it like this.

There are all kinds of tips, rules, “best practices”, or whatever that gurus will try to shove down your throat about subject lines.

The truth is that those are all lies.

At the end of the day, the only way that you’re going to figure out what actually works for your audience is by trying different things, keeping track of what works, and trying to learn from it.

It’s called A/B testing. I heavily recommend that you check out this guide on A/B testing by Kissmetrics — it’s a great introduction.

I also recommend reading this article by Joanna Wiebe, so you can see some real world results of someone else’s split test.


How do I get people to read my emails and buy things?

Good copywriting.

Good copywriting is the way you talk about your product, the way you describe the benefits, and who your audience is — and getting that information into their brain as fast as possible.

Good copywriting is also knowing that people don’t like “to be sold”. It’s about finding ways to make the selling experience enjoyable and informative.

The easiest way to sell products through emails is by telling stories.

There are a few different types of stories you can experiment with telling about your product.

The first type of story that works really well, is stories about how your product helps the hero. “The hero” in this story is going to be your audience, or at least someone who your audience can “stand in for”. Sometimes it’s you, sometimes you can make up stories about “characters” who are based off of your customer avatars, or sometimes you can highlight a real story of how your product helped one of your customers.

You can find the whole letter here.

Neville says that when he’s writing sales emails like this, he tries to make the story the first 70–80% of the email. The call to action to buy is only the last 20–30%.

The second type of story that works really well are “behind the scenes” stories. Usually they offer the reader a sneak peek behind the curtain of your business.

You can experiment with explaining the thought behind the product, which could be your own story of your problem, the work you put into solving it, and how you ultimately wound up at your product.

The best way to learn more about telling these type of stories is to watch Kickstarter. Specifically, poke around the most funded Kickstarter projects of all time for example after example of how founders explain their stories, their struggles, and the thoughts behind their products.

Let’s pick Exploding Kittens as an example to talk about, I think their Kickstarter page does a great job of framing just how you could go about telling a “Behind the Scenes Story”:

Click on the link to their Kickstarter campaign above and read the whole “Origin Story”!

The founding story of Exploding Kittens actually started to raise awareness about a BIG problem: 7 million pets go missing in the US every year.

The Oatmeal creator Matt Inman had another extremely popular project before Exploding Kittens, called “The Kitty Convict Project”.

The Kitty Convict Project was a comic strip that aimed to raise awareness about the millions of pets that go missing in the US every year, and publicized a goofy little solution that animals should wear bright orange collars to be identified as house pets. You can find a cache of this comic here if you want to read the whole thing.

The Kitty Convict Project got wide publicity only a year or so before Exploding Kittens hit the scene, but that goes to show you just how powerfully your origin story can sell.

Although Exploding Kittens is just a silly board game, the message that resonated so strongly with people wasn’t the board game itself — it was the founder’s origin story that sold the product.

So back to selling. How you sell in email is by telling stories about your product where the customer is the hero. Stories that explain to them how the product helps them save the day. Stories about how you got to the solution that help customers connect with you.


The Nuts & Bolts

Okay, we just covered some high level concepts about getting people to open and read your emails.

I wanted to dive down into some tactics. In a moment I will let you in on 2 automated email sequences that anyone in any industry can set up to drive top line revenue.

First, let’s talk about segmentation and automation.

The main tactic that is going to drive revenue is automation.

Segmentation is also a big revenue driver, because the more laser targeted the offer is to one specific person the more likely they are to buy the product — but so many people try to get way too fancy with segmentation at first. Even sometimes paralyzing them, causing them to not build any email sequences at all.

A tip from popular online blogger Pat Flynn: For segmentation, all you need to do it keep it at customers and not customers for now. Don’t psyche yourself out.

Even this simple level of segmentation will allow you to effectively target your email campaigns.

To find out all of the segmentation tool information you’ll need, you’re going to have to use Google to find the directions for your particular mix of services. Are you on Shopify or WordPress? Or something else? Do you use Mailchimp, ConvertKit, Infusionsoft, or some other email service?

First what you need to Google is YOUR MAIL SERVICE + “segmentation” (this is what the Mailchimp directions look like). If your service’s directions list the website platform you use, great! You’re in business, and should be able to set everything up from inside of your email provider.

If you can’t quite figure it out, I would look at a tool called Zapier to help your website communicate with your email service which of your subscribers have made purchases.

Onto automation.

I’m going to share 2 easy sequences you can set up to support top line growth.

Every single business has two main levers that drive revenue:

  • Turning not customers into customers
  • Turning 1st time customers into 2nd time customers

First, let’s talk about turning not customers into customers.

My go to is to set up an “introduction series” sequence of emails. It’s a 5–10 step autoresponder that educates the consumer about your company. You can introduce them to the topics you will help them with, and generally the sequence is building to a final “ask” for a sale.

We’ll get to what you should write in these emails in a second. How should you set up the triggers?

I like the trigger factor to be “Did they open the email, or not?”.

When you’re setting up the sequence, I would make the trigger on all of the emails for “One day after opening (the previous email)”.

If somebody is engaged and reads your email, the best time to email them next is immediately afterwards.

If they don’t open the email at all though, sending an email the next day could be detrimental.

So plan for people to “fall out” of your sequence. Meaning that they don’t open one email, and then will fail to receive the following emails in your sequence. What should you do then?

Set up trip wires.

Let’s say that a person read email #1, but then didn’t open email #2. Now they won’t get emails #3–5.

Set a trigger for if the user did not open the last email, and 4 days later send the same email with a different subject line. That then has the same triggers as the “regular” introduction sequence following.

So here’s what it looks like:

The reader opened email #1, but not #2.

4 days later they get email #2 sent to them again, but with a different subject line. You’ll then have a trigger that if the reader does open email #2.2, the next day they’ll get email #3.2.

You set this up, at least in Mailchimp, all under one “workflow”. What I do is have emails 1–5 in Mailchimp with the regular “Send one day after opening previous email” trigger.

Then I put #2.2-#5.2 underneath. You can select individual emails in the automation workflow in Mailchimp, so I would have the trigger for email #2.2 to be “Send 4 days after NOT opening previous email (email #2)”. Emails #3.2, #4.2, and #5.2 all have the trigger “Send one day after opening previous email (which in this case is email #2.2).

Rinse and repeat for emails 3, 4, and 5.

So what if the reader opens emails #1, #2, but not #3?

Well, same thing.

Send email #3.3, the same body text as email #3 with a different subject line with the trigger “Send 4 days after NOT opening previous email (email #3)”. Emails #4.3 and #5.3 should have the trigger “Send one day after opening previous email (which here is email #3.3)”.

What types of emails should you have in your Introduction sequence? Here are some types I use…

You’re in the Right Place

I set it up that there is a welcome email that triggers immediately after sign up. The email is basically to get the reader to self identify as the audience that your product serves.

The first sentence of a welcome email I did for a professional services client (they sell corporate training packages):

“If you’re a leader in your organization, this is for you.”

Some of the copy of a welcome email I did for a consumer product (a subscription box in the cooking niche):

“Welcome to FoodCrate. Just by signing up you’ve taken the first step to a life full of great company, amazing memories, and delicious food. Our mission is to teach foodies, and all home cooks, how to use the power of flavor to vanquish weeknight dinner blues forever.

You want to identify who your content is for in this email, and let the reader know that you understand the types of problems they’re trying to overcome.

You can also let them know what to expect from your email list going forward:

“Over the next few days we’re going to be sending you more emails stuffed with helpful cooking tips and other great stories — so keep your eyes out for emails from K from FoodCrate.

WOW Them

This one is pretty simple. You’ll want to send them a thoughtful email that is valuable, usually that helps them solve a problem. The problem you should solve should be related to the pain that your product (which at the end of the sequence you’re going to ask for a sale) solves.

Some people wonder “Won’t the reader not want to buy my product, if I help them solve their pain?” Don’t worry if it overlaps with your solution, people who opt not to buy your product because a free solution solved their problems frankly weren’t going to buy your product at all anyway. They were never in the market for a paid solution in the first place.

Again, you’re trying to communicate that you understand their problems and train your audience to think of you as an authority for that topic.

I‘m going to show you real copy I wrote to help you see how you can pick “lessons” for your own product, and how I tie stories into teaching in the emails.

Here is some copy from a WOW Them email that I’ve written:

“When you’re first learning how to cook, or trying to elevate your technique and get to “the next level”, making all those mistakes can be really frustrating!

But you’re not alone (even though it can feel like that sometimes). Even professionals make mistakes!

I remember one time I was at my mom’s house. I think it was when I was out with that first back surgery where my insurance didn’t kick in. I was cooking dinner and normally it’s a great experience.

But this was my first time cooking salmon FOR them specifically, so I wanted to do a nut crust. It was pistachio crust. So I salted and peppered the fish just a little bit, but I guess I got a little crazy seasoning the nuts because I wasn’t thinking that they were already roasted and salted.

So I start seasoning them, adding even more spices on top of this… It looked BEAUTIFUL, okay?

And we all sat down, and as I took the first bite my lips puckered like I tasted a big old lemon. My mind was like “SHIT”.

And both of my parents took a bite at the same time, and both of their faces scrunched up and my mom said “Umm… Well this COULD have been pretty good…”

That is definitely NOT the face you want to see with fish!

Perfect segue into what I wanted to talk to you about today:

I’ve worked in my family’s spicery for over 12 years, so I’ve had the opportunity to talk to THOUSANDS of home cooks over the years and help them tweak their meals. I’ve noticed most of the time I’m correcting the same few mistakes that come up over, and over again!

I’ve done some research, and there definitely is not good information like this out there — otherwise everyone would be a perfectly trained chef, right? 😉 Luckily you don’t need to fly all the way to Florida to learn this secret sauce, I’m going to share the 2 most common mistakes home cooks make AND how to fix them with you right now.”

Incorporate Your Story

The biggest part of doing this successfully is telling your story, in a way that it’s about the reader.

Don’t talk about yourself just to talk. Information that you’re sharing with the reader should directly relate to explaining how you can benefit them.

Particularly, try to relate it to what problems you’ve personally struggled with, how you found out that other people struggle with your problem, what about your past gives you the expertise to help your audience?

Here are some examples from real copy:

“You don’t grow up in a Spanish-Italian family, like I did, without coming to love cooking. How can you not when huge festive meals together are at the center of every family get together?

My mission is help every home cook fall in love with cooking by teaching them how to make mouthwatering meals.

Everyone in my family, from my grandma to my dad, has their own cooking specialty. For example, my dad is a grill master and my grandma was a traditional Spanish cook. I grew up learning how to cook from all of them.

When I was maybe 5 or 6, my step-mom showed me baking essentials…”

The Ask

Finally, after relating the values that are important to your audience to your own business through stories, and after you’ve given them some value before asking — it’s time to ask for the sale.

You’re going to want to make sure the top 70–80% of your email helps the reader understand how your product helps them. Instead of just telling you “avoid just listening features, be sure to talk about benefits” I’m going to pull some examples from copy for you to look at.

Read these to see how I turn “Our box has 3 ounces of spices” into “Here is what 3 ounces of spices does for you”:

“Look [name], we all know cooking is a valuable skill.

Knowing how to cook well can help you stay healthy, make great memories, and even simply add a smile to your face every day.

How can you make mouthwatering meals with FoodCrate?”

“I scour the earth for the best tasting spices, I know just what combinations will make the tastiest mouthfuls for you to snack on. I’ll send you 3 ounces of the most delicious natural seasonings you’ve ever had.”

“You absolutely won’t find better spices, for a better price near you. I know this because I was a food industry professional for more than 15 years, and I could never find these high quality spices myself!”

Do You Hate Me?

This is my secret weapon. I learned it from The Ask Method by Ryan Levesque (and the Ask Method Masterclass).

What you’re going to do is send a email with a bit of a silly title that says “Do you hate me?” where essentially you’re asking readers to reply to you why they decided not to try your product.

The goal is to use the survey results to adapt your autoresponder to best suit your audience. You can create FAQ’s, or add new emails to your sequence that address people’s objections.

Here’s the text of a Do You Hate Me email that I wrote based off of what Ryan teaches:

Did we not do a good job of explaining something? Did we not cover a specific topic that you’re really dying to know about? What’s the single biggest reason you decided not to try FoodCrate?

Was it something I said, something I didn’t say, OR do you just hate me? 🙂

Please click here and tell me what was the #1 reason you decided not to try FoodCrate?” (The “click here” links out to a Google Form survey).

Next, let’s talk about turning 1st time customers into 2nd time customers.

The simplest way to do this is to thank them for their first purchase! My favorite way to do this is using something called a discount ladder.

Normally people use the discount ladder to turn not customers into customers, but I find it’s even more effective when implemented against people who have already bought from you.

Basically, what you’re going to do is create emails that give the reader a bigger and bigger discount the longer they go without purchasing something from you.

So the first email you may give them a 10% discount. The second you may give them 15%. The third, maybe you give 20% and free shipping.

It helps you save your promotional dollars while maximizing revenue, because people just have different needs. One customer might not be ready to buy right away and take all the way until the 20% discount to have a strong enough reason to convert.

But if all another customer needs to prompt a purchase is a 10% discount, you can save the extra money and offer them that instead of 20%.

How you’ll do this is by setting up an automation workflow that is triggered by a purchase.

You’ll create your 3 emails and their copy. Again, thank your customer for their purchase. Let them know you appreciate it. Tell them you wanted to thank them for being so amazing with a little gift.

The first email, send it 30 days after the purchase.

For the second email, send it 20 days after the first email. You’ll want to look for a trigger that says something about activating if the user did not open the previous email.

In this one, you can be even more empathetic about how much you appreciate them! Tell them you hope they’re enjoying their purchase, or ask them if they are.

For the third email, repeat step 2. 20 days after the second email. Again using a trigger about activating if the user did not open the previous email.


You want to avoid sending out one size fits all blasts as much as possible.

Instead, reward customers for coming back to you with custom automated emails from the CEO thanking them. Remind customers who have abandoned their cart to check back. Let customers who haven’t visited you in a long time know that you’re still thinking about them.

Your relationship with your customers should grow and change over their lifecycle as your customers.

Email marketing isn’t about shooting one email off to somebody. It’s about developing systems that support your audience, educate your audience, and drive revenue to your business.


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Business, Email Marketing, Entrepreneurship, Marketing, Startups


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