Years ago (can’t remember when), I wrote my first client email.
It felt like a shot in the dark.
I was applying theory from a course or two + direct response principles, but this time, for real, paid work.
Sending that “Here’s the email” message to them, with Google Doc attached, took me an hour of pacing back and forth, sweating bullets.
When I finally sent it…
The client was fine with it.
We sent it, and it made some sales.
I can’t remember exactly how many, but it did.
Things got better as I dug deeper into the industry.
I worked my way into higher-volume roles with agencies (often owned by friends of mine) where I was responsible for near-daily emails and monthly flow build-outs across up to 5 clients.
Not to mention my private clients with whom I collaborated on email marketing and strategy directly.
Years later, and I’m well over 1,000 emails.
Reps. Reps. Reps. With the occasional “copy teardown” from a copy coach in between.
It’s been a FAR better learning experience than burying my head in theory.
A few patterns have emerged. Things I’ve seen play out repeatedly among dozens of brands, niches, and business models — from supplements to leather goods to golf to pet health.
Some of what I’ve learned is counterintuitive, while some of it confirms what experienced marketers already suspect but rarely say out loud.
All of it has changed how I approach email in some way.
Here are 8 of those lessons…
1. Strategy > Copywriting Skill
If your offer sucks, it’s hard for me to write good copy for it.
I can’t highlight the benefits or differentiate from other options.
And I feel slimy (which, besides the ethics of shilling a bad product, makes it harder to ideate and write).
On the other hand…
The best product in the world won’t sell well if you’re not selling to the right people.
I can’t sell the world’s tastiest hamburger to a room full of vegans.
How about a real-world example:
A meal kit brand I worked with wanted to try and win back canceled customers.
No matter how creative we got, how direct we got, how insane an offer we offered…
We didn’t get many bites.
That wasn’t the right audience. They had a past bad experience or were averse to monthly meal subscriptions.
Much easier to go after new leads or retain/upsell/cross-sell existing subscription customers.
When your offer’s great and you have the right audience, copy works best. It’s a multiplier.
And copy flows out of your fingers far more easily.
I think of the time I sold my buddy (who is also into health, wellness, and grass-fed meat) on Good Ranchers.
Great product. Person interested in that kind of stuff. Hardly felt like I was “selling” him… more like being excited to show him this cool thing I bought.
Think of it like this:
A bridge doesn’t work if you don’t have two pieces of solid ground to connect.
Copy is the bridge, while offer and audience are the two sides.
Lastly…
Writing “direct response copy” style won’t work for everyone’s audience.
As my friend Siim says in his version of this article, “I highly doubt a mom selling yoga mats online uses Bencivenga bullets, problem-agitation-solution frameworks, and a PS section with fake urgency.”
Comes right back to knowing your audience and writing for them.
2. Plain Text > Design (But There’s Nuance)
Heavily designed emails look like ads.
Plain text emails look less “marketing-y” and feel more like a real message from a real person — even if the reader knows it’s from a brand.
More reads, which means more clicks and sales.
Plain text also loads faster, renders better on mobile, and lands in the primary inbox more often than HTML-heavy stuff.
All that said…
SOME niches lend themselves better to design, and the degree varies.
Apparel and jewelry work well with heavier design, for example.
In some cases, you might open or close promotions/launches with design emails.
Head here if you want the full, correct, nuanced take on plain text vs. design in email marketing (and when/where to use design elements).
3. Some Emails Will Flop (And That’s Ok)
When you write thousands of emails like I have, some will bomb.
It’s statistically impossible to write a banger that sells your product like hotcakes every single time.
And sometimes, it’s independent of effort.
For my own list…
I’ve spent 2+ hours on emails I was proud of that got low opens and little to no clicks.
I’ve also spent 15 minutes dashing off a thought or silly story that got tons of engagement.
Similarly, for clients:
I’ve written longer, educational pieces I thought were fascinating that didn’t sell well…
And then crank out something I thought was “meh” in the middle of a busy day, just for that email to set a record.
What matters is consistency and volume. Showing up daily (or whatever your cadence is) will build familiarity with your list and translate to a stream of consistent sales.
A flop or two won’t kill your business, but going silent on your list will.
Flops are data. It tells you what your list (or that segment) doesn’t resonate with, or perhaps something about your send time.
Pay attention to flops and they’ll help you improve.
Similarly…
4. Subject Lines Matter Less Later On
Subject lines matter more early on because you’re still building sender reputation. Subscribers don’t know you yet, either.
So the subject line carries the open if it happens.
But as you mail over time, that burden shifts to your sender name itself.
Subscribers get used to the helpful and/or entertaining content that each email contains. They learn to expect that when they see your name, there’s something good to read.
A clever hook or benefit + curiosity subject line doesn’t matter as much.
Instead, subject lines become “context.”
They tell the reader what to expect that day, such as a product launch, promo announcement, or even what product you’re pitching at the end.
Some readers may not open NOT because they don’t like your content, but because that particular offer or content is not relevant to them…
But they’ll still open future emails based on them coming from you. Important distinction.
This is why obsessing over which arrangement of words is best in your subject line loses relevance as you go.
Deliverability, list health, and consistency of value have far more impact on open rates over time than any subject line formula.
Continue writing good subject lines, but “go with the flow” more and focus on delivering excellent email content.
5. “Good” Emails Follow a Handful of Frameworks
Writers across formats (books, movies, sales pages, case studies, name it) will tell you that proven pieces of writing tend to follow a handful of recognizable structures.
Same goes for email.
The same frameworks come up time and again:
- Problem/solution
- Belief-shift
- Stories
- Listicles
And several more.
It’s like the “skeleton.” An animal can’t exist without a skeleton. All the important stuff sits on that skeleton.
Same with frameworks. The copy is the material that sits ON the framework, creating a cohesive piece of writing.
No need to reinvent the wheel every time.
In fact, creativity only works best within constraints.
Absolute freedom leads to analysis paralysis. Constraints force you to prioritize, focus, and innovate.
Having the proven frameworks on hand saves you even more time, though.
It’s why I assembled a nifty reference vault of my top frameworks. I refer to this document often when trying to keep my emails fresh.
6. The Fortune Is In The Flows
The majority of brands I audited — even those that put a lot of effort into campaigns — were leaving a LOT of money on the table through a lack of email sequences.
Automated sequences work around the clock to make you sales. That’s why I attack these first when working with new clients.
The sooner they’re in place, the longer my clients can make money in perpetuity.
My clients get the best ROI from their investment in hiring me.
Not to mention they gain extra capital to reinvest in other operations.
A few examples:
- A Welcome Sequence to welcome new subs and make the first sale
- An Abandoned Cart Flow to recover lost carts and maximize ROAS
- A Post-Purchase Flow to beat buyer’s remorse, get the customer a win, and make the next sale
- A Push to Continuity Flow to get repeat buyers on recurring delivery
Set up your flows once, and they run forever, with only minimal maintenance and perhaps some A/B testing.
Oh, and broadcasts feed flows.
For example, you send an email to a product page. 5 of your clickers reach checkout, then leave. Without an Abandoned Checkout Flow, you lose those sales.
Build those flows ASAP. Check this out if you’re not sure how to build the most important and want a complete walkthrough.
7. Segmentation Should Be Simple
Some email marketing gurus like to complicate segmentation to make things seem harder, justifying their existence.
But you don’t have to build out dozens of microsegments and send 100 emails daily to cover each one.
In practice, a handful of key segments do the bulk of the work.
Your X-Day Engaged (such as 120-day engaged) segment, for example, will be your main mailing segment. D
Expand that engagement window when opens climb high enough. Shrink it if they fall.
Doing so maximizes sales while guarding deliverability.
Beyond that, tracking your VIPs and your “never bought” people is the furthest you really need to stretch segmentation.
Automated flows are where things get more granular, but, as discussed, these are “set up once and let run” instead of “constantly manage.”
8. List Health Matters More Than Size
Let’s return to my meal kit brand example.
Their canceled customers list exceeded 100,000 people. Every send had terrible opens, clicks, and almost no sales.
NO SALES TO OVER 100,000 PEOPLE.
Even their “never bought” customers segment did not engage a TON, despite being more engaged than the canceled customers.
On the other hand, a pet health brand I worked with had under 10,000 people on its list… yet we had over 50% opens and made several sales per email.
In fact, I ran a 4-email price hike campaign to just 5,600 people on this brand’s list and generated $23,690.41.
~$6,000/email ain’t bad to a list that small.
Goes to show you that list health and engagement matter more than size.
Two things I’ve learned to use for maintaining list health:
- Regular cleaning to remove non-openers (after checking that they truly ARE non-openers, rather than it being us suffering some deliverability issue)
- Sunset Sequence to auto-clean off unengaged subscribers
List size is a vanity metric if you don’t ensure the subscribers are high-quality. Revenue per subscriber is more useful.
1,000+ Emails Later…
Doing teaches you more than reading.
Writing all those emails has taught me lessons everyone talks about, as well as some people don’t talk about.
But I found an overall theme:
Simplicity + consistency beats cleverness.
A healthy list, solid offer, and clear but compelling copy put through reliable frameworks outperform fancy strategies and complexity almost every time.
I did the learning for you. Hit like and subscribe, leave a comment…
Then go write some emails with these rules in mind and watch your email marketing revenue climb.
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