E-mail Marketing: How to Monetize Your E-mail List

Oahu Online Business delivered another great seminar, this time on e-mail marketing. Presenters Sid Savara and Andy Fossett shared terrific insights from the data they’ve discovered in their own businesses. I’ll recap some of the highlights, provide resources for further reading and other thoughts.

Why Do E-Mail Marketing?

It’s easy to dismiss e-mail as obsolete, with new hot social platforms coming out every year.  Everybody’s using Facebook, Twitter, Instagram, Snapchat, Vine, Periscope, etc.

However, e-mail is the workhorse, the reliable tool that consistently delivers profits.

This article makes the case for e-mail so I don’t have to:

5 Reasons Email Marketing Crushes Social Media Marketing for B2B

Here’s an excerpt. The statistics are a little old, but the concept still applies:

Did you know that email has nearly three times as many user accounts as Facebook and Twitter combined? That’s a whopping 2.9 billion.

In fact, if you imagine a full cup of rice is the number of emails sent every day, then by comparison, all the daily posts on Facebook would make a miserable 10 grains—barely enough to pick up with a chopstick. And all the tweets sent every day would be a measly 4 grains. In fact, Facebook and Twitter combined make up just 0.2% of the number of emails sent each day.

Not including spam.

Imagine social networks as the cool teenagers who aren’t very effective in the business world. While e-mail is the seemingly boring grown-up who actually gets the job done.

Not only is e-mail profitable, it’s also powerful. As in making a difference in who gets to run the country powerful:

The Science Behind Those Obama Campaign E-Mails

A large part of this Businessweek article focuses on e-mail marketing for the Obama election campaign.


Most of the $690 million Obama raised online came from fundraising e-mails.

Holy shit! I’d like to see an Internet marketing guru pull off a launch that rakes in more than half a billion dollars. That’s 690,000,000 reasons why it’s worth learning how to do e-mail marketing. If e-mail can do that for a presidential candidate, imagine what it can do for your business.

E-mail Deliverability: Getting Your E-mails into the Inbox

This is something we Internet users take for granted.  We send an e-mail, and it gets into the inbox of who we sent it too.  We just assume it will work.

Making sure e-mails get delivered is a full-time job.  E-mail services like Gmail are fighting 24 hours a day against spam.  All too often, even innocent opt-in e-mails that the users subscribed to can get swept into the “Spam” folder by accident.  E-mail delivery experts at e-mail service providers like Aweber have to work just as hard to keep their companies off the spam black lists, out of spam traps, etc.

Deliverability can be an incredibly boring and technical subject. For me, it’s second only to video compression for how fast it can put me to sleep.  But it’s absolutely essential to know the basics so your e-mail get through to your subscribers.


There are several forms of “authentication” that Internet Service Providers (ISPs) and e-mail services use to verify which e-mails are valid vs. spam.

Here they are:

SPF Record



Rather than go into the technical details (read those Wikipedia links if you want an instant headache), the easiest analogy is to think of them as different types of “stamps” you can put on your e-mails so you can prove to ISP’s they’re legit. The more stamps you have, the higher your deliverability will be.

To get these installed, here’s what you can do:

–Ask your e-mail service provider (like Aweber) to provide the SPF record and etc.  They will be lines of code.

–Go to your web hosting company, open a support ticket, copy and paste the codes your ESP gave you, and send that support ticket.  Either the web hosting company can do it for you or show you how to install the authentication on your domain.  You’ll have to add the codes to your DNS records.

You just have to do this once, and all your e-mails will have these “stamps” on them going forward.

Here’s a podcast episode that goes into more detail:

The McMethod E-mail Marketing Podcast #93: Matt Paulson – E-mail marketer John McIntyre interviews Matt Paulson, who runs an e-mail financial newsletter business and sends millions of e-mails per month. He’s also a technical guy, so he understands the nuts and bolts of deliverability.


All right, so you’ve got the tech covered. Now what about your content? How do you make sure you don’t write things that trigger the spam filters?

Here’s a good resource from HubSpot:

The Ultimate List of Email SPAM Trigger Words

Writing tip: I would just write naturally for the first draft of an e-mail, then check this list afterwards. Don’t try to remember what not to write when you’re trying to write. Makes it harder for yourself.


One of the biggest ways e-mail services evaluate e-mail is interaction. The more interaction between senders and recipients, the more the e-mail service thinks there is a real relationship, and won’t put your e-mails into the spam folder.

Some ways you can do this:

–Get subscribers to “Whitelist” your e-mails. It’s basically the opposite of a subscriber labeling your e-mail as spam. Aweber has a great blog post on how to do this for various e-mail services: How to Whitelist Us. You can link to it in one of your first autoresponder messages to new subscribers.

–Replies.  I don’t know if it’s true, but one deliverabilty expert swears by the tactic that if you can get a subscriber to reply twice, Gmail will whitelist your e-mails.

A lot of bloggers recommend to ask your new subscribers what they need help with the most and get them to reply with their answers.  As well as improving deliverability, you’ll get ideas for more helpful content and products to create for your subscribers.

–Opens and Clicks. I go into more detail below.

–Attachments. This is a cool tactic Sid discovered by accident.  He had just switched over his website to having a “responsive design” (where the website layout adjusts to being on different-sized screens). He asked his subscribers to send him screenshots of what his website looked like on their smartphones, just to check his website looked right. He received thousands of e-mails in response.

Sid noticed that his deliverability went way up after doing that. He suspects Google treats sending attachments (like photos and images) as a signal of a relationship between sender and recipient. This already got me thinking of ways to take advantage. Like holding a photo contest and giving away a prize.

List Hygiene

Over time, as your list grows, you’ll also gain a lot of “dead weight,” i.e. subscribers who don’t respond to your e-mails. This can hurt your deliverability, if it seems like a large portion of your list is dormant and unresponsive.

There are several types of e-mail addresses you want to remove from your list:

  • Unsubscribes. This one is obvious. If they say they don’t want to receive your e-mails, you should remove them. What is not obvious is that Aweber and other ESPs often don’t remove unsubscribes automatically. That means you’re still paying for storing e-mail addresses of people who don’t want your e-mails!
  • Uncomfirmed subscribers. These are people who signed up for your e-mail list, but never confirmed their subscription by clicking the link.
  • Bounces. There are “hard” bounces and “soft” bounces. A hard bounce is where the e-mail address is fake or there was a typo, so e-mails don’t get delivered because the e-mail address doesn’t exist. A soft bounce is because the inbox is full or some other legitimate reason.
  • Un-opens. People who don’t open your e-mails.
  • Un-clicks. People who don’t click on the links in your e-mails.

You might want to periodically remove the non-openers from your list. You can try to “reactivate” them by segmenting out of your main list, sending them a last e-mail asking if they want to keep getting e-mails and to click on a link to indicate that. To spice it up, you could offer a valuable freebie like an e-book to entice people to click.

Some hard-core marketers also remove the non-clickers. This can drastically reduce your list size, which saves money on your e-mail service provider fees. They typically charge per person on your list (even the ones who unsubscribed! The ESP still stores their records).

Your click-through rates will skyrocket because your list will only have clickers, who are the hyper-responsive people.

Depending on how fast your list is growing, you could clean your list every 30, 60 or 90 days.

Increasing E-mail Opens

The tried-and-true tactic is using a catchy subject line to get people to open your e-mails.

Caveat: curiosity and mystery are fine, but always make sure you “pay off” in the actual message. Deliver on the promise. If you always bait-and-switch, people will stop opening your e-mails.

How to come up with catchy headlines:

“The Magazine Trick” – Go to Google Images and do a search for a magazine in your niche.  A bunch of magazine covers should come up. Click on each cover to enlarge it and read the headlines.  You’ll find things your target audience cares about, plus good headlines.

“Viral” websites – BuzzFeed, Cracked, Reddit. Use them for inspiration.

Reddit deserves a little more detail. Popular posts get “upvoted” by users, so you’re seeing what headlines are really effective. You can also go into “sub-reddits” targeted at different niches for more specific and effective headlines.

Cosmopolitan and Reader’s Digest websites also have catchy headlines. Reader’s Digest is especially good if you’re targeting Baby Boomers.

Increasing E-mail Clicks

Andy talked about using formatting to make your links stand out and get clicked more.

–Put more than one link in your e-mail.

–Add more space above and below your link.

–Center your links in the e-mail.

–Use characters to focus reader’s attention. Can feel cheesy, though.

Example: —>>> Click my affiliate link <<<—

How to Write E-mails that Sell (without feeling sales-y)

One of the attendees voiced a concern I’m sure a lot of entrepreneurs have had: how do you sell–without “selling out”? In her case, she was in the real estate niche, and talked about a guru who had really high-pressure sales e-mails with pitch after pitch.

You really have to strike a balance. Good copywriters have declared that if you really have a solution (your product) that can help people, you are doing them a disservice by not doing everything you can ethically to convince your prospects to buy it, so they can get it in their hands and solve their problems. There’s nothing wrong with promoting solutions.

Telling stories is a great way to build a bond with subscribers. But which stories? Tell the right stories, and your subscribers will feel like they know you and will want to buy from you. Tell the wrong stories, and you risk over-sharing, telling irrelevant details, appearing narcissistic and turning off subscribers.

There’s no magic bullet, but this episode of The McMethod E-mail Marketing podcast points to a solution:

Episode #101 – Megan Macedo on Smashing Goals and Kicking Ass In Business By Being Yourself (develop the ultimate USP and much more)

I must have listened to this 5 or 6 times, and I rarely listen to podcasts more than once. She really took the whole cliche of “Just be yourself” and explained how it could be a practical strategy, not just feel-good fluff.

Megan really nails it with her “Empathy Zone” concept. Think of where your experiences and your prospect’s emotions overlap, and tell stories from that. Use stories of your experiences to reflect their own feelings.  I’m not doing it justice with this description, best to listen to it explained from the source herself.

I remember an attendee in a past seminar who trained yoga teachers. For example, she could tell stories of how she discovered yoga, how it changed her life, the struggles with enrolling students in her new yoga school, finally achieving success when she got her 100th student, etc. And talk about related interests like tea, dieting, etc. Something out of left field like sports gambling might not fit and is best left out.

Ideally, stories like that should resonate with her audience. Her subscribers will “insert” themselves into those stories and remember when they’ve gone through the same things. Finding someone who “gets” you is powerful stuff.

Going on a slight tangent, here’s an article about how therapists market themselves:

What Brand is Your Therapist?

I want to highlight this passage, which shows that a prospect’s buying decision can be based on a random connection you might not have planned:

Many people admit that a sense of connection is more important in choosing a therapist than the clinician’s reputation or training.

One woman told me that she chose her therapist because “she looked relaxed” in the photos on her Web site, “and I didn’t want anybody too intense, because I’m really high-strung.”

A man explained that he found his therapist via referral, but “the Web site sealed the deal, because I discovered that her father was a Holocaust survivor, and I knew that was territory I needed to visit.”

Another woman chose her therapist because her blog revealed that she had successfully overcome “food issues” in college, something this client was struggling with.

By telling personal stories, you provide more potential touch points that prospects can bond with you over. Shared experiences can trump fancy credentials.

After telling stories, transition to your product. Getting back to the yoga example:

“I spent 10 long hard years figuring out how to build a profitable yoga school. If you want to avoid the pain and shortcut your success, check out my course “Yoga Studio Success Blueprint.” I didn’t have a course like this when I started out. I want you to have the advantage I never had.”

Then link to a sales page with more information. The e-mail’s job is build the relationship and send traffic to the sales page.

Tell stories in your marketing, save your teaching for your info products (and paying customers).

How Frequently to Send E-mails

I can’t remember which marketer made this joke:

“How often should you send e-mails? Only on days you want to make money.”

In other words, every day. The fitness guru and marketer Matt Furey was one of the first to really advocate sending daily e-mails to your list. Ben Settle has taken up that mantle and influenced many other entrepreneurs to also do daily e-mails.

You can get away with daily e-mails, as long as you’re transparent about it.  Say you’re going to send daily e-mails on your opt-in forms and landing pages. Ben Settle’s landing page even has a checkbox, asking you to check the box to acknowledge that you know you will be getting daily e-mails.

If you have an existing list and want to switch to daily, definitely let your subscribers know first. Possibly set up a weekly list and daily list so people can choose their preference.

Ready-to-Go E-mail Campaigns to Make Money Fast

Andy taught several ways to start making money with your e-mail list right away.

“New Member” Promotion – Look at your analytics and figure out the average number of days between when a subscriber opts in to your list and when they make their first purchase.  For example, let’s say it’s 7 days. Use your e-mail software to automatically send out a “New Member Discount” after that day, like Day 9.

“Off the Wagon” Promotion – Find the average number of days people stop opening/clicking e-mails or between the first and second purchase. You’re trying to identify when subscribers “fall off the wagon” and unsubscribe, or just stop reading your e-mails. Use your e-mail software to send a last-ditch, Hail Mary effort to get one more sale before they leave entirely. Send a “Customer Appreciation Discount.”

Run one of these campaigns every month. Alternate between the two.

E-mail Marketing for Affiliate Marketing

My favorite takeaway from Andy’s teaching in this section was simply to add value. If you want to get more commissions, really earn them by helping your subscribers. That beats any super-ninja tactic.

Ways to Add Value

Reviews – Help people make an informed buying decision. Andy named The Wirecutter as a great example of a site built on reviews. In that case, with electronics products. The New York Times did a profile of founder Brian Lam here:

Buffeted by the Web, but Now Riding It

Coupons and Sales – Depending on the niche, the vendors will periodically send out info on sales and discount promos. Then you can turn around and e-mail them to subscribers. You can also negotiate directly with vendors for discounts.

Assistance – Coaching sessions, done-for-you services, how-to videos, etc. If you can help customers use the product or get set up properly, that’s super helpful for them.

Complementary Bonuses – This can be the easiest and most effective if you already have your own products. Pick one that would be a good match for the affiliate offer, or even offer a bundle of your products. Or create one from scratch.

You would tell your subscribers about the bonus(es) they’ll get if they buy through your affiliate link. Then think up some way to verify. One popular way is to have buyers e-mail you their receipts, and you would manually either send them the product or give them access to a private website.

I’m not sure about Clickbank, but I know marketers promoting JVZoo offers can upload their bonuses to JVZoo. So buyers using their affiliate link automatically get access to the bonuses after purchasing.

Marketing Automation: The Next Level

Good to become aware of marketing automation for future reference. But Sid and Andy stressed that you should not feel overwhelmed and think you have to set up all this complicated stuff to get started.

Get your first opt-in form up on your website and just add people to one e-mail list. You can worry about tagging, segmenting and having multiple autoresponder sequences later.

The Definitive Guide to Marketing Automation – To avoid making this blog post 100,000 words long, I’ll refer you to entrepreneur Neil Patel’s guide.

The Essential and Complete Guide to Drip Marketing – This post is so extensive it could be an e-book sold at a premium price. It even has its own clickable table-of-contents. While the post is aimed at software companies, all businesses can benefit from better segmenting and more relevant follow-up.

How Companies Learn Your Secrets – A New York Times article about how companies use data mining and behavioral tracking to laser-target their sales promotions. Contains the infamous story of how the retail chain Target figured out a teen girl was pregnant before her father did.

E-mail Marketing Automation Tools

These tools can feel heavy-duty. So if you’re starting out it’s better to go with a service like Aweber or GetResponse, which are also plenty powerful.

ActiveCampaign – This one seems to be more widely adopted compared to the others on the list. Nowadays, when I’m looking at tools, one of the top considerations for me is whether this new tool integrates with other tools I’m using.

ConvertKit – Aimed at bloggers.  The screenshots of their automation rules dashboard looks very simple and intuitive compared to clunkier control panels on other platforms.

Drip – Seems to be aimed more at SaaS software businesses, although info marketers can certainly use it too.

More Resources

The McMethod E-mail Marketing Podcast – I’ve linked to several episodes in this post already.  The host John McIntyre is a practitioner himself, and interviews other e-mail marketers, copywriters and entrepreneurs. He’s freely admitted that he uses his podcast as a pretext for getting free consulting from top industry pros.

photo credit: 5 Simple Hacks That Will Double Your Email Open Rates via photopin (license)

One thought on “E-mail Marketing: How to Monetize Your E-mail List

  1. Rupali Embry

    Hey Marcus, this is an awesome write-up! I’m going to check out your cited resources which sound excellent. I appreciate the references to the yoga site. Very helpful! Thanks so much.

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