7 Email Marketing Strategies That Should Not Work

7 Email Marketing Things That Shouldn’t Work (But Do)

Want to know how to make the most of your email marketing? Then we've got something pretty special for you here. It's the 7 best email marketing strategies that shouldn't work but absolutely do. They're undervalued and probably even sound a little bit ludicrous. But if you want better results with your email marketing, you might want to try them out. 

Ready to have your mind blown? 


(0:20) Our outrageous email marketing contest.
(5:53) Introducing our new sponsor - Selzy.
(8:36) Send more emails.
(9:54) Sell in every email.
(10:59) Talk about your life - not your products.
(13:21) Stop using benefit-led statements in your subject lines.
(14:34) Send emails that piss people off.
(17:43 ) You don't need ALL the people!
(19:15) Send ugly emails.
(21:58) Subject line of the week.

Our outrageous email marketing contest

We always say your marketing needs to stand out, and we often talk about having an obnoxious offer. So we’re doing a contest where we'll pay for a whole year of your email marketing platform, give you a full year of all our resources, campaigns, and coaching inside of our membership, The League, and we'll even post you the 10 books we recommend everyone reads to improve your email marketing.

It’s outrageous and totally free to enter. All you have to do is go to this link to check out the details and enter. So what are you waiting for? This contest closes soon – you don't want to miss out! 

Introducing our new sponsor – Selzy

For every dollar you spend on your email marketing, you’re supposed to make at least a $36 return. But that's hard to do if you're scratching your head wondering how to use all of these advanced email marketing features. This is why we're introducing Selzy – a tool where you don’t have to squint your eyes and give yourself a migraine to get started.

You’ll be able to launch your first campaign in just 15 minutes, create emails and automations super easily, and if you need to, you can call for backup 24/7 from Selzy’s amazing support team. Selzy is sponsoring this episode of The Email Marketing Show, so if you want to give it a shot, for just $49 you can have a lifetime account with unlimited emails, automation, segmentation, and some advanced analytics. And that’s all of that for the price of around 10 lattes! You can grab this bonkers deal here.

1. Send more emails

So let's get into the best email marketing strategies we recommend you try out. You see, there's this thing in marketing and entertainment that says you should leave people wanting more because “less is more”. But with email marketing “more is more”. We have never sent more emails and not made more money. In the history of time, that’s never happened. Generally speaking, when you send more emails, you make more money! It's as simple as that!

And this may sound loopy because people say that if you send too many emails, your subscribers are going to leave. And some might! But that's only if you send shit emails. If you send good emails, people are going to want more of them.

We also hear that sending too many emails means you’re being too salesy. But that’s not true because if you go quiet for months, then suddenly turn up and go on a big selling spree, and then go quiet until your next launch, that is the exact definition of being salesy! Whereas if you're sending emails all the time, and you're permanently in people's inboxes, you come across as less salesy.

2. Sell in every email

The second in the list of our 7 best email marketing strategies is to sell in every email. People think that you can’t possibly do that, but if you use our Bottomless Email Strategy, you’ll know exactly how to do this. Selling in every email means you don't turn into the person who only shows up when you’re ready to sell. If you sell in every email, the moment someone's ready and the time is right for them, they know exactly where to find the link to buy.

3. Talk about your life – not your products

A lot of people who send emails only talk about their products. But most of the time, the reason why we’re sending an email is to share something that’s going on in our lives. With your email marketing, look after the emotional needs of your audience. Give them connection, inspiration, and entertainment. Also, make them feel valued and like they’re a part of something.

In our course The Bottomless Email Strategy we talk about 9 different types of values you can give in your emails, and how you implement them is important. The reason we send emails is to tell our list about something we think they’ll find interesting, different, or unique. But we also give inspiration and ideas to help towards the thing we teach. And we’ll always mention a product, a piece of content, or resource that’s going to help.

That’s the key differentiation here – we're sending an email because we have something interesting, scary, sad, or happy to share. And as a by-product of that, we’re also going to help people and give them a chance to buy something.

So email people about things that cause a response or a reaction – things we can all relate to. For example, as small business owners, we all have different but similar challenges, hopes, dreams, aspirations, goals, or pain points. We struggle with the same things and thrive on the same things.

Focus on sending emails about those things and then as a by-product mention what you sell and give people inspiration. Don’t just email to tell people to buy your thing! Instead, give people reasons to connect with you as humans because the sales will come as a by-product of that.

4. Stop using benefit-led statements in your subject lines

A lot of people advise talking about writing headlines and subject lines that include the benefits of your product or service to your readers. But we find that removing the benefits from the subject line makes your email sound less like a marketing email that’s trying to sell something. And that means people are more likely to take a look at that email.

So instead of benefit-led headlines and subject lines, use compound curiosity. But we'll talk more about that on another day, so stay tuned!

The Top 10 Books To 'Power Up' Your Email Marketing

10 book recommendations that will improve all areas of your email marketing (including some underground treasures that we stumbled upon which have been game-changing for us).

5. Send emails that piss people off

This may sound crazy, but you want to create enough noise that some people in your industry won’t like you and won’t want to learn from you. Is this really one of the best email marketing strategies out there? Yes! Because there are so many people who are interested in the thing you do, teach, serve or sell that you don’t need everyone. In fact, you only need a tiny percentage of them to love and rave about you and for you to be the only person they want to buy from. So what you actually want to do is to intentionally get rid of everyone else! All you want are the hard-core believers who love everything you do, say and stand for.

For example, we swear in our emails. We are very opinionated and sometimes we send emails that we don't think are offensive, but some people get offended anyway! Saying stuff that some people are going to get pissed off by is something we intentionally try and do. Because we want to surround ourselves with a handful of people who love everything we say. And when those are the only people around you, you don’t have to watch your back and think about what you’re going to say next. You never have to worry about it – you can just say whatever you want. If it pisses people off, that's okay because it’s going to draw other people closer.

And remember that it’s almost impossible to piss everybody off! Being opinionated means that some people will always leave – but not everyone will!

6. You don’t need ALL the people!

This means that it’s perfectly acceptable to delete huge chunks of your email list, and we do this a lot. What we mean by deleting is that we stop emailing them – you don’t have to remove people from your email marketing platform if you don’t want to. In fact, we tend to keep most of our subscribers even once they've unsubscribed because it's useful to have the data of who they are and what they did. It certainly comes in handy if they want to re-join our list later – that way, we still have all that history. But that’s our choice. We continue to pay for people on our platform who have unsubscribed (and some platforms don't charge you for that).

So stop emailing huge chunks of your email list when they unsubscribe, and, of course, make it easy for them to unsubscribe. In fact, encourage them to leave if they’re not interested. Always push for maximum engagement – even from a smaller list of subscribers.

In fact, one of the things we do very early in our email engine is to encourage people to unsubscribe if they're not interested. And that's probably one of the best email marketing strategies you'll ever come across! We do this in several places:

  • In our welcome sequence (which we call the Getting to Know You sequence).
  • If you're the one who stopped emailing, then we have a campaign for that too – it's the Terrible Friend campaign, which basically says that you’re back in the game (it’s a re-engaging type of campaign). And in that sequence, we also invite people to unsubscribe if they’re not interested.
  • Or if people disengage, we give them a chance to re-engage through the LOL Revival campaign. And if they don’t, we stop emailing them altogether.

So don’t feel bad about the fact you might have a big churn in your email list.

7. Send ugly emails

By this, we mean removing images and any of those fancy templates that your email systems want you to choose. This is included in one of the 7 best email marketing strategies we want to share because what we call ugly emails work so much better! They look more like the email you'd receive from a friend and less like a piece of marketing. And that means people's barriers don't go up.

The uglier the email, the better. Even if you sell a visual product, such as artwork, jewellery, or handmade goods, for example, take the images out of the email. You want people to have to click somewhere to go and see the pictures. Because if they get everything they need in the email, they have no reason to click. And that click is going to improve your sender's reputation with the email platforms and allow people to use their imaginations and engage with your words emotionally. If you’re using good stories, you don’t need pictures!

Enter our outrageous email marketing contest

So that's it when it comes to the 7 best email marketing strategies that shouldn't really work but do. If you want to get down to business with your email marketing, we have something pretty special for you. It’s a contest, and if you're reading this at the time it's being published (14th September 2022), it's closing this weekend, so hurry!


  • We'll pay for 12 months of your email marketing platform (and if you don’t have one yet, we’ll make our recommendations and help you pick one).
  • We’re going to give you a 12-month membership of The League, which means you get access to our tools, campaigns, and resources, and you’ll know what to do in your email marketing platform.
  • But we'll also ship you a copy of our 10 highly recommended books to help you with your email marketing. They're not email marketing books for the most part, but they will help you level up your skills.

We’ve never done anything this crazy before, and we’re super excited to help you have amazing success with your email marketing! So check out all the terms and conditions and enter the contest for FREE here.


Make More Sales with our cutting-edge Psychology-Based Email Marketing Programme

  • Psychology-based email marketing.
  • 45+ Email Campaigns.
  • Video Campaign Workshops.
  • Growing Library of Video Trainings.

Subject line of the week

This week’s subject line is “You coming? [First name]’s ticket.” We use this when we're running an event of some description, like a webinar or a five-day challenge. And we tend to use it in one of two places:

  • When someone hasn’t registered. This is the email that goes out shortly before the event starts.
  • And when someone’s registered and you want to send them a reminder.

The idea of adding “[First name]'s ticket” gives physicality to a digital registration, and that works really well. Try it out! 

Useful Episode Resources

Related episodes

7 Essential Email Campaigns Examples For Your Business.

9 Psychological Things That We Use In All Of Our Campaigns.

Why You Shouldn’t Worry About Your Unsubscribe Rate.


FREE list of the top 10 books to improve your email marketing

If you want to write better emails, come up with better content, and move your readers to click and buy, here's how. We put together this list of our Top 10 most highly recommended books that will improve all areas of your email marketing (including some underground treasures that we happened upon, which have been game-changing for us). Grab your FREE list here

Join our FREE Facebook group

If you want to chat about how you can maximise the value of your email list and make more money from every subscriber, we can help! We know your business is different, so come and hang out in our FREE Facebook group, the Email Marketing Show Community for Course Creators and Coaches. We share a lot of training and resources, and you can talk about what you're up to.

Try ResponseSuite for $1

This week's episode is sponsored by ResponseSuite.com, the survey quiz and application form tool that we created specifically for small businesses like you to integrate with your marketing systems to segment your subscribers and make more sales. Try it out for 14 days for just $1.

Join The League Membership

Not sick of us yet? Every day we hang out in our amazing community of Email Marketing Heroes. We share all of our training and campaigns and a whole bunch of other stuff. If you're looking to learn how to use psychology-driven marketing to level up your email campaigns, come and check out The League Membership. It's the number one place to hang out and grow your email marketing. Best news yet? You can apply everything we talk about in this show.

Subscribe and review The Email Marketing Show podcast

Thanks so much for tuning into the podcast! If you enjoyed this episode (all about the 7 best email marketing strategies that shouldn't work but do) and love the show, we'd really appreciate you subscribing and leaving us a review of the show on your favourite podcast player.

Not only does it let us know you're out there listening, but your feedback helps us to keep creating the most useful episodes so more awesome people like you can discover the podcast. 

And please do tell us! If you don't spend time on email marketing, what do you really fill your working days with? We'd love to know! 

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