Why marketers who call this “annoying” are getting it all wrong

Chief Creative Officer

It’s never my intention to startle anyone with the advice I share in this newsletter.

That’s why I was blindsided by the small but savage outcry I got after Nugget 51 where I mentioned a service for people who email their list … every day.

These readers felt emailing that often was suffocating. That it choked the life out of any possible chance of long-term loyalty. 

Around five years ago, I would have contributed my own verse to this feisty chorus.

Then, I started following a copywriter called Daniel Throssell. I didn’t know Daniel was a daily emailer at the time. But I’d heard about his legendary “Parallel Welcome Sequence” and, like so many others, I got sucked in.

Almost two thousand emails later, and I’ve never been tempted to jump ship.

Before I go any further, I’m not suggesting you start emailing your prospects and customers every day. But if you stick with me, I’ll prove that … 

Sending frequent emails will not be seen as “annoying.” 

I put that last bit in quotes because that’s the objection I hear most when I talk about sending emails at a decent clip.

And sure, if your emails are boring, self-serving, or don’t give your readers any value, your unsubscribe link becomes increasingly seductive.

But—as with any of your marketing—if you write emails focused on your audience, sending them at a regular cadence will help you:

1. Build your authority so people see you as an expert

2. Forge deeper relationships because you’re genuinely there to help

3. Sell more stuff

If you bristled at #3, you’re not alone. The selling part makes a lot of people nervous.

They think sending too many emails will hurt sales due to an army of viable prospects charging toward the exit. Here’s my two-part response to that:

First, if you’re sharing information that benefits your readers, you shouldn’t get a flood of unsubscribes. And the few people who do leave were never your customers anyway. 

This is simply your list going into “self-cleansing” mode, which ensures you’re always talking to people who want to hear from you.

Second, and this is important enough to tattoo on your forehead …

Every email is a selling opportunity. 
But not every email should be a closer. 

If you look back at those three bullets, I put them in sequential order. 

Because pounding someone with nothing but promotional messages can feel as pushy as a waiter asking for your order before you’ve looked at the menu. 

But if you use your emails to show your expertise, build relationships, and wait … did I hear you say you make your own tater tots?! … then your readers are far more likely to give you their money when you offer them something that solves their problem. 

Once someone becomes a customer, continuous follow-ups keep you in front of them and increase the chance they’ll purchase from you again.

Alright, before my advice starts sounding too woolly and impractical, let’s you and I brainstorm a handful of reasons to email your contacts more often.

I’ll go first …

Seasonal changes – If your business fluctuates throughout the year, you could send a series of emails helping your customers prepare for any anticipated shifts or downturns. 

Beyond offering friendly advice, you’re using empathy and understanding to make your customer feel seen. And when your audience knows you get it, they’re more likely to see you as someone who can help them. 

Product pre-sells – Before your product launch sequence, you can pre-sell your product using emails, too. This stage is often more educational than promotional. 

Develop a series where you talk about an unsolved problem and the steps your readers should take to overcome it. Then, reveal your new offer (which conveniently solves the problem) in the final email.

Free trials – If you offer a free trial, a daily email sequence during that period is a proven way to convert more users when time expires. This is where you can highlight key features, share customer success stories, and answer commonly asked questions. 

You can also use the “5 inches, 5 miles” technique where you show your prospect the immediate benefits they’ll gain, along with how much more they’ll achieve in the long term.

Cross-selling – In the grand old days of mail-order sales, a company’s most valuable prospects were their current customers. Of those people, the ones who bought more recently were most likely to buy again. That’s no different today. 

So, if you have other offers that help your customers solve additional problems, don’t wait. Promotional emails from a trusted sender (that’s you) have a high chance of generating repeat business and building loyalty.

“Dealer’s choice” – This is where I throw it back to you. 

Take a look at the brands that email you often. How do they keep their messages fresh? What are they talking about when they’re not selling? Even if you don’t open every email, why do you continue to welcome them into your inbox? 

Email marketing or otherwise, repurposing winning approaches from other brands is a simple shortcut to sharpening your own communications.

And don’t worry if you do something wildly different than someone else. Their great idea may be even more powerful in your hands. Or as Jedi Marketing Master Jay Abraham once said … 

“A business strategy that may be as common as dirt in one industry can have the effect of an atomic bomb in an industry in which it has never been used before.” 

And just in case you were wondering … 

There’s no magic number of emails you should be sending in any given situation. Just make sure you limit every email to only one topic to keep it simple, memorable, and actionable.

If you’re using a sequence to tell a longer story, end each email by teasing your next topic to build curiosity and boost engagement. 

Or just use cheap tricks like sending people to a music video until the next idea comes.

Here’s a song to play you out >>> 

See you next time. — Matt


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Matt Cascarino

Chief Creative Officer
Matt is a professional storyteller. That used to be a thinly veiled way to say you still lived with your parents. But the truth is stories have existed since the dawn of humanity and they still have the power to move people, even if it’s no longer from the path of a charging mammoth. Throughout his career on both the agency and client sides, Matt’s work has been known to compel audiences to indulge in higher thread counts, abandon Lenten sacrifice, or move to the suburbs. He’ll even conjugate a noun if he has to. The bottom line: Matt is our agency twofer. Strategy and Creative. The Big Idea and Stealth Deployment. He’s a single expense yielding a dual return. And who doesn’t love a bargain?
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