One of the reasons why I launched Emails that Sell was to challenge the conventional way of doing ecommerce email marketing.
But I also do it because it helps me become a better writer.
Turns out dissecting great copy sharpens your writing instincts more than most paid courses.
I highly recommend it.
So far, we’ve broken down welcome emails, post-purchase flows, winback sequences, and more.
Today is the first time we’re diving into an invaluable writing skill:
Storytelling.
If I could bless every marketer with one skill, it’d be the ability to tell a captivating story.
Today’s breakdown is a bit different because instead of looking at a brand selling physical products, we’re dissecting a creator’s welcome email.
When I signed up to Kieran Drew’s email list, I had no idea what to expect.
A few weeks in, and nearly every email from him is marked grey – because I open and read them.
Kieran has mastered the art of storytelling.
Before we get into it, here are the rules:
What is Emails That Sell?
Each week, I break down an email from a DTC e-commerce brand. Some of these brands are absolutely killing it when it comes to email marketing.
My goal with this series is to challenge conventional email marketing. Expect to learn different copywriting techniques, sales psychology, and consumer behavior — everything that moves you away from hard-selling discount campaigns and other mass-market tactics.
If you have an email you want me to break down, send it over to me on LinkedIn or at marketing@siimpettai.com.
Let’s get into it now:
A lowercase subject line that promises a story?
This is highly curiosity-driven, and I love it.
Let’s look at the body copy:
Uh-oh… we’ve got a lot to unpack here because this is some fine-ass storytelling.
“It’s March the 30th, 2022, and I’ve just sent my first-ever sales email.”
This sets the scene immediately.
Also, notice how Kieran is showing, not telling:
He doesn’t say: “I’m nervous.”
Instead, he says: “My heart is trying to smash its way through my ribcage as I stare at Gmail.”
As a reader, you’re not being told a message.
You’re shown a vivid scene.
That’s a sign of powerful writing.
The next few lines are key:
Now, I’ve only read one storytelling book in my life.
It’s called Storyworthy by Matthew Dicks.
According to Matthew, every story must have an elephant.
The Elephant is the thing that everyone in the room can see.
It’s the problem, the tension, or the mystery that hints where the story is going.
When you read Kieran’s email, it becomes clear pretty quickly that the Elephant here is his fear of being a failure.
Look at some of these sentences:
“People say making money online is easy.”
“I’d been writing for 18 months and still hadn’t monetized.”
“As I imagined the shame of crawling back to my boss…”
Here’s the thing with stories:
Yes, your audience wants you to succeed, but they don’t want it to happen immediately.
It’s the struggle, the pain, the uncertainty before the “peak moment” that makes the story great.
Kieran had been working 6 days a week for nearly two years, and hadn’t made a single buck.
He continues to put in the work, but his inner monologue still tells him “You look like a f*cking idiot.”
Matthew calls this the Backpack strategy.
It’s when the storyteller loads up all his fears and dreams before revealing the epiphany.
The bigger the dragon, the greater the hero.
Now, let’s look at the delivery:
Again, notice the showing vs telling.
“I sat for several seconds in stunned silence, then leapt out of my chair and ran up and down my flat, shouting at the top of my lungs in joy.”
He could’ve just said “I felt ecstatic.”
Or since Kieran is from Leeds, he could have said how “over the moon” he felt.
Jokes aside, great writers understand that the human brain thinks in images, not words.
You have to nail that in your head if you want to write great copy.
One last thing on storytelling:
Great stories are 5-second moments that change your life.
A great story requires transformation.
If the protagonist doesn’t go from point A to point B (not physically, but in their way of thinking), you don’t have a story; you have an anecdote.
So for Kieran, the story isn’t really about the sale he made.
It’s the realization that this online entrepreneurship thing is actually possible.
I remember experiencing something similar with my first freelancing paycheck.
It was $60 for writing two emails.
Sounds kinda silly, I know…
But for me (and in Kieran’s case), it’s THE moment you realize that everything you’ve dreamed of could actually become a reality.
And since that moment, you’ll do whatever it takes to make it possible.
Kieran puts it really well here:
Now, I’m not entirely sure if Kieran has ever been on a roller coaster, or what kind of roller coasters they have in the UK, but last time I checked, roller coasters are supposed to have peaks and valleys.
This thing is a rocketship. 😀
What happens next is really important:
Kieran removes himself from the expert status.
He isn’t saying he got it right the first time.
Far from it, he had to go through a series of failures to land one sale (remember the Backpack strategy).
This builds a lot of trust.
It also proves he isn’t a theorist; he’s a practitioner sharing his learnings.
That makes him relatable.
He then tackles some objections:
Many people never get started with online entrepreneurship because of their limiting beliefs.
We’ve all been there, but the truth is that you don’t need anyone’s permission to start sharing your thoughts online.
All you need is an idea, some device, and an internet connection.
Now, I think Kieran could have easily ended the email here.
But he also shares an educational tip:
Personally, I think this could’ve been a theme for a separate email.
But I’m just nitpicking here.
Anyway, I love the conclusion:
“The internet is your playground” perfectly captures the lesson of the story.
Also, notice how Kieran isn’t trying to hard-sell you anything.
Entertainment is the main value here.
And if you’re operating a daily newsletter, that’s the way it should be.
Only at the end does he introduce his offer:
Adding this in the PS section is smart.
A lot of people (up to 90%) read the PS section.
But it’s sort of like a subtle nudge. If you’re ready to buy today, go ahead. If not, all good.
The call to reply to the email is another slick move.
Getting people to respond is not only good for your email deliverability, it shows that you care about your audience.
Great email!
TL;DR
Key takeaway #1: Show, don’t tell.
Key takeaway #2: Every story needs an “Elephant” – tension, conflict, or mystery.
Key takeaway #3: Use the Backpack strategy to build emotional investment.
Key takeaway #4: A story without transformation is an anecdote.
Key takeaway #5: Build trust by sharing your failures.
Key takeaway #6: Serve your audience first.
What’s next
Go check out Kieran’s stuff if you want to become a better writer.
Also, read Matthew Dicks’ book on storytelling. You won’t regret it.
If you haven’t already, subscribe to my email list and get notified of every Emails That Sell analysis + my weekly newsletter.
