John Bejakovic

My checklist for email copywriting

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In 1935, Boeing demonstrated its new plane, nicknamed the Flying Fortress, to military observers.

The demonstration was a mere formality, because the plane, a four-engine behemoth, exceeded the army’s requirements in every way.

Except for one problem. During the demonstration, the plane took off, climbed steeply, stalled, and crashed, killing the two pilots inside.

An examination determined that nothing mechanical had gone wrong. The crash was due to pilot error. It seemed that the Flying Fortress was simply too much plane for one man to fly. Nonetheless, the air corps purchased a few Flying Fortresses and tried to figure out what to do.

Their solution was very low-tech. Instead of changing anything about the plane, or insisting on more training for the pilots, they simply came up with checklists to handle the complex procedures for each operation: takeoff, landing, cruising, bombing…

Thanks in part to these checklists, the Flying Fortress eventually wound up playing a key role in World War II, and became the third most produced bomber of all time.

I thought of this story today, because I came up with my first checklist for email copywriting.

Even though I’ve written hundreds of sales emails by now, I haven’t systematized the process, and sometimes, I find myself crashing and burning for no good reason. Today, I became aware of how the process goes when it goes well, and I want to write it down to make sure I don’t ever forget it ever again.

So here it is, along with an example (one of the emails I was working on today, for a home fermenting kit):

STEP 1. Get an idea for an angle or topic

I normally do a lot of research for the emails I write. This includes going through the sales letter, testimonials, transcripts I did with people from the company, examining the product itself, digging around on forums online, etc. As I do this, I write down possible topics and angles for emails.

For this particular project, I also went through a few hundred customer surveys. A lot of customers mentioned that they were interested in fermenting because they wanted to lose weight.

My first idea was simply to try to connect fermented foods to weight loss. While I had a good testimonial on this topic, the science seemed fairly vague and tenuous (more on this in step 2 below). However, a related and relevant topic — antibiotics and weight gain — seemed very solid, so I decided to go with that.

STEP 2. Search around for more details

If I know a lot about a topic, or I have a personal story I can share, I can skip this step.

However, I can’t simply riff about antibiotics and weight gain. It’s not a topic I know enough about, so I needed to do more research. In particular, I wanted to find some kind of supporting scientific study that actually made the connection. And ideally, I also wanted to find a story to kick off the entire email.

I have a few go-to places for both kinds of resource. For scientific research, ScienceDaily seems to have reliable summaries of recent research. For stories, articles that appear in The Atlantic and The New Yorker tend to be good sources. Beyond this, a bit of googling will usually solve all research problems.

For this particular email, I found a study from Johns Hopkins University that effectively said, “the more antibiotics, the more weight gain.” The story I found was about a woman who went to the doctor to get rid of her hormonal acne, but wound up with an extra 14 pounds, thanks to the antibiotics he prescribed her.

STEP 3. Write up different subject lines

Keeping In mind the topic I want to cover, and the details of the research I want to include, I start to write a bunch of different subject lines.

At this point, I have a fairly large stack of index cards with good headlines that I can use as templates or inspiration. These aren’t “classic” direct response headlines (eg. “They laughed when I sat down at the piano”).

Instead, they are the titles of articles I’ve found myself clicking on over the past sevreal years (eg. “De Beers admits defeat over man-made diamonds”). Most of these are general-interest articles that originally appeared on the front page of Hacker News, so they are vetted for being curiosity-inducing.

I force myself to write down 10-15 of these subject lines, even if I think they sound stupid. Then I just pick the one that I think sounds the best, ties into the content I want to share, and ideally, gives me a bit of edge I can use in the email (I can’t describe this any better right now).

For this particular email, the subject line I ended up with was “Antibiotics are shockingly good at causing weight gain”.

STEP 4. Write the body of the email

At this point, all that’s left to do is to tie the pieces together. That means starting off with the story, developing this a bit (in the example I’ve been using, that means talking about the supporting science study), and then tying this in with the product I’m promoting.

I won’t include the entire completed email here. But it looks something like this:

Smooth sailing thanks to a checklist

The “Rule of One” applied to email copywriting

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In the 2006 version of Casino Royale, there’s a classic James Bond pickup scene.

Bond is talking to the beautiful wife of one of the bad guys. After a bit of flirty banter, Bond looks her straight in the eye and says, “What about a drink at my place?”

He stares at her. She stares at him. The tension builds.

“Your place,” she says breathlessly, “is it close?”

“Very,” says Bond.

Now imagine if Bond couldn’t play so cool. Instead of throwing out that one proposal, imagine if he threw out three:

“What about a drink at my place? Or maybe some nachos? How about breakfast tomorrow in case you’re busy now?”

Even with his ice-cold stare, odds are he wouldn’t get the same response.

“Bond. James Bond. You can call me Jim. Or James. Whichever is easier.”

A while ago, I was reading “Made to Stick” by Chip and Dan Heath. This is the best book I’ve come across  on how to present ideas clearly and in a way that people will remember. One of the things the Heaths say is, “Say one thing. If you say three things, you end up saying nothing at all.”

Michael Masterson and John Forde’s “Great Leads” emphasizes the same concept, which they call “The Rule of One – One Big Idea.”

In fact, the book opens up with the story of two speeches that were given by two Agora copywriters. One speech focused on one idea, the importance of clarity in writing. The other was something like “12 rules I follow when writing copy.”

The audience thought both speeches were terrific. But at the end of the night, people were only talking about the single idea in the first speech.

I’ve recently been working on some emails for a cool product. The product helps people make their own fermented food. And the emails I’m writing are specifically for people who’ve stated that they want to ferment for health reasons.

I’ve been going around in circles writing these emails. I need to get across a few ideas. One is that fermented foods are important for your health. The second is that fermenting can be a hassle. A third is that store-bought fermented foods aren’t a great choice compared to fermenting food yourself.

The problem is I’ve been trying to do this in the same email. This breaks the “Rule of One.” No wonder I’ve been re-reading the emails and thinking they are somehow weak and unconvincing.

The fix is simple. Pick one idea. Develop it in detail. Present it clearly. And then do the same for the other ideas, but in separate emails.

The parable of the marketing apprentice

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Do you know the parable of the sorceror’s apprentice?

The sorcerer leaves the tower for a bit, and his apprentice uses what magic he’s learned to get the broom to come alive and start fetching pails of water. Except the stupid broom, once it has gotten the command, won’t stop. The apprentice hasn’t learned this magic incantation yet.

So more and more water keeps being sloshed into the tower. The apprentice starts to panic and decides to chop the broom in half. Not smart. His problems are now doubled — two brooms are bringing twice the water.

This is akin to what happens when people start learning about marketing and copywriting. For example, the very first bit of marketing advice you’ll hear is to focus on how your offer benefits the prospect.

“Don’t make it about you, make it about them!”

It’s a solid piece of advice. And it should be used, when and where it’s needed. But is it the only incantation a marketer needs to know?

I thought of this a few months back when I got a promotional email from a health coach named Ari Whitten. Ari runs a very popular online course called the Energy Blueprint, and he was sending an email to his list to promote his new book. The subject line? “My New Book is HERE!”

Who cares, right? Where’s the benefit? What’s in it for me, Ari?

Well, apparently, much of Ari’s list cares. Through motivating his own loyal followers — and probably with a lot of affiliate help — Ari’s book shot up to the #2 spot in the health category on Amazon, and within the top 40 of all books on Amazon.

In a way, this is reminiscent of what Gene Schwartz calls the “most aware” state of customer awareness. From Gene’s Breakthrough Advertising:

The customer knows of your product — knows what it does — knows he wants it. At this point, he just hasn’t gotten around to buying it yet. Your headline — in fact, your entire ad — need state little more except the name of your product and a bargain price.

At the same time, this isn’t really about awareness of the product. Instead, the awareness is about Ari himself. People know him and want what he has to offer, without taking too much care of what his offer actually is.

But let’s tie this back to the sorcerer’s apprentice.

Wouldn’t Ari have been more successful if he had pitched the benefits of his new book right in the subject line? Maybe, at least for selling this one book. That’s like telling your broom to go fetch the water.

However, for the long term, always shouting benefits might not be the best strategy. If you keep writing to the same people, and all you do is talk benefits, without doing other things to build a bond with your readers (like entertaining them, teasing them with curiosity, or relating to them on a personal level), then you eventually lose their attention and you make your job harder — or impossible — for the long term.

That’s when you try chopping the axe in two. In the marketing world, that usually means making more and more extreme promises and claims. When that doesn’t seem to work, you chop again and again, making still more extreme claims.

That is, until the sorcerer comes back from his afternoon walk. He surveys the mess, throws the sleeves of his robe back, and  finally casts the magic spell (called “relationship”) to drive all these marketing problems away.

“My new book is HERE!”

Bejakovic’s hierarchy of email marketing

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What’s the most important thing in email marketing? Ben Settle, in my opinion the top guy teaching this topic, has said that the number one thing he strives to do with email is to build a relationship.

It made sense to me when I first read it. But it seemed to click in my mind in a different way today, when I got an email from somebody in Ben’s sphere of influence.

The email had a Ben-style curiosity-drenched subject line. And yet, I purposefully chose not to open the email, because I know from previous experience that I don’t care too much for what that sender has to say.

That made me think a bit (specifically about the difference between levels 4 and 5 below). And the conclusion is the following hierarchy of email marketing.

The levels are ranked from least sophisticated to most sophisticated. For each level, I’m including a few examples of subject lines that represent that level, which I managed to dig up in my own inbox.

Level 1: Pointless

These tend to be emails from corporations and big organizations that have heard email marketing is important. However, since these organizations have no idea of what to put in their emails, they usually blast out pointless newsletters that are focused on random aspects of their own corporate existance (best case) or nothing at all (worst case). This is the lowest form of email marketing.

Example subject lines:

“New Bestcare website”
“#MakeBaobabFamous”
“What’s new in MailChimp?”

Level 2: Sale

The next level up is when the sender makes an offer. The offer can be a sale, a coupon, or a new product announcement. This works — if your readers are ready to buy and they just need to be nudged with the right kind of carrot. Unfortunately, many companies doing email marketing (especially in ecommerce) only ever send out these kinds of email.

Example subject lines:

“Your favorite mist, on us”
“Save 25% Now + Win a Trip to Maui”
“Get 33% OFF Absolutely EVERYTHING + FREE Shaker”

Level 3: Benefit

Now we’re getting into copywriting territory. “Sell the sizzle, not the steak!” This is where much of the Internet Marketing world lives. This category of emails is all about announcing (and frequently screaming) benefits — though I would also include transparent fear-mongering or urgency-based emails here.

Example subject lines:

“Higher T in 14 days”
“Boost your ranking with these SEO hacks”
“Closing: On-Demand Video Views = Sales”

Level 4: Curiosity

This is still a higher level of email copywriting, which is trying to persuade more skeptical, more sophisticated readers. At first blush, there can be overlap with emails in level 3, but these curiosity emails tend to be less direct and more broadly interesting than the benefit emails. Email courses (think Andre Chaperon) also go in this category.

Example subject lines:

“Do NOT do keto if…”
“The shocking truth about exercise”
“Why drug expiration dates don’t matter”

Level 5: Relationship

Finally, there is the highest level, relationship email marketing. That’s when readers open up your email and read it simply because they’ve grown to like and trust you over time.

This is the only kind of email marketing where you’re not living “email to email” — in other words, you can get away sending all sorts of random and personal stuff, even in the subject line, and people will still read on. In some way, this is coming full circle to the “Pointless” level — except that people actually want to hear what your opinions are and what’s new with you, because you’ve built that relationship.

Example subject lines:

“Bensplaining the importance of daily emails”
“BUSTED!”
“My new project”

“One weird trick for reaching the top of the ziggurat”

Now, there’s an important distinction between levels 1-4 and level 5.

Levels 1-4 are under your control. It’s simply a matter of what you put in the email.

However, you can’t force people to have a relationship with you. All you can really do is write good emails that will hopefully resonate with some of the people on your list.

Technical note: Being at the Relationship level doesn’t mean you only send out personal updates or rants. Quite the opposite. You can and should still frequently mix and match content from the different levels — even within one email. That’s how you get to — and stay at — the top.

The best kind of proof

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I want to give you a demonstration of spooky action at a distance
For this to work, all you have to do is read the instructions below, and then when you get to the part that says “GO” carry them out. Once you’re done, simply keep reading this article.

So here are the instructions of my spooky-action-at-a-distance:
(Read through them once before you try them out)

1. Clasp your hands together with your fingers interlocked, thumb over thumb, index finger over index finger, etc.
2. Now, stick your index fingers out straight, but keep them apart.
3. And then, simply look at the space between your index fingers until something spooky happens. It might take as long as 10-15 seconds, but it might happen sooner as well.

Ready?
GO
.
.
.
.
.
.
.

Are you done?
That means my spooky-action-at-a-distance must have come through across time and space and pushed your two index fingers together until they were touching.

At least, that’s the idea
Hopefully it worked. And in any case, the point is not really to convince you of action-at-a-distance, but simply to illustrate the most powerful kind of proof. And that’s demonstration.

Product demonstrations work very well
You can take a car for a test-drive. You can try a shirt on at the store. You can walk around a home before buying it.

Then there are performance demonstrations
In his farewell seminar, Gary Bencivenga told the story of Elisha Otis, who invented the first safe elevator. Otis got in an open elevator in front of a crowd, while his assistant first cut one and then the other cable holding the elevator in place. Otis’s safety mechanism kicked in, saving Otis and the elevator, and finally convincing people that elevators are safe to use (hello skyscrapers).

This still works today
A while back, a video for the Purple mattress company went viral. The core of the video was a clever demonstration — the raw egg test:

Sometimes though, the demonstration doesn’t even have to be of the product
Like in this post that you’re reading. Or in this Bill Jayme add for Smithsonian Magazine:

This clever demonstration seems to be about engagement

So what’s the conclusion?
Always try for a demonstration. There are many creative ways to do this, and it’s worth putting in some thought to come up with one that works for you.

How to get going when you don’t know what to write

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The first part of the Big Con happens on a train. I’m talking about the movie The Sting, where Paul Newman plays Henry Gondorff, an expert con man, who’s looking to fleece a mob boss named Lonnegan. (Lonnegan killed off one of Henry’s old pals.)

So Henry is now on a train, where Lonnegan regularly runs a poker game. Lonnegan cheats. But Henry cheats better.

Of course, there’s a lot of detailed info necessary to out-cheat a cheat. That’s ok. Henry has got a whole team of tricksters and confidence artists on his payroll. One of them, a guy named J.J. Singleton, comes to give Henry the lowdown right before he goes in to join the poker game:

SINGLETON: “He usually plays with a Royal or a Cadenza. [handing him two sealed decks] I got you one of each. He likes to cold deck low, 8’s or 9’s.”

“That’s nice work, J.J.”

Armed with this info, Henry goes into the poker game.  He slaps some gin on his face, acts the fool, and cleans up the table. Lonnegan is furious — and hooked for the rest of the Big Con.

Several times, I’ve written sales emails that started out just like this post. In other words, they referenced a movie, and then tied it into what I was promoting.

Once, this was the X-Men — I talked about Professor X’s ability to read minds, and said how this would help guys who want to please their women better (this was for a “rekindle your romance” course). Another time, I started off talking about the Shawshank Redemption, and then tied this into an ebook on treatments for chronic kidney disease.

The thing is, in both those emails, I was stuck at first. I knew the movie tied into what I wanted to say, but I didn’t know how to make the link. I made several false starts that were weak or rambled on for too long. The answer in both cases was to pick a specific scene, and lead off with that. And that’s the marketing lesson I want to crystalize in this post:

When it’s hard to figure out what to write, the answer is almost always to look for more info. Sometimes, that means going out and doing more research. Other times, it simply means focusing more on the details that are already at my disposal — like picking a specific scene from a movie.

The case against steak upsells

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“Hell yeah we’ll take five more steaks if you cut the price”

Imagine going into a restaurant. You’re hungry and you’re raring for a steak. So you look over the menu, find your steak, wince a bit at the price, but decide to get it.

“I’ll have the 12-ounce steak,” you say to the waiter. He writes this down patiently in his notebook and then says,

“Would you like 18 more ounces of our fine steak at 50% off? You can always take it home with you if you don’t finish.”

Because you’re hungry and it’s a tempting deal, you order the extra slab of meat at a discount. But of course, when it arrives, you can’t finish it. You take it home, where it becomes more of a responsibility than a joy, sitting there cold and hard in your fridge. A few days later you toss it out.

Next time, you stay away from that restaurant. Somehow, you have a bad feeling. You spent too much money. You were emasculated by not finishing the steak. And you don’t need the temptation a second time.

I’ve recently heard a couple of contrasting positions on upsells. Just yesterday, I listened to an interview with successful copywriter and marketer Justin Goff. He talked about how the best upsells are often more of the same.

“Buying one bottle of supplements? How about 3 more at a discount?”

At the same time, Justin talked about the incessant need most direct response businesses have for new customers. According to Justin, new customers are the ones who buy the product, and even the ones who take up affiliate offers. That’s position one.

Then there’s Sean D’Souza. Along with a copy of his Dartboard Pricing book, I got a copy of a talk Sean did for the Ken McCarthy’s System Club. This talk is on the topic of consumption. And one of the things Sean says explicitly is that you don’t want to overwhelm your customers with product, even if they are willing to buy it.

Sean also talks about treating customers the way you would treat your kids — that is, looking out for them and charting a path for them down the line.

Perhaps not surprisingly, Sean’s business seems to rely on a much smaller number of customers, who happily keep coming back year after year and forking over thousands of dollars for Sean’s courses and trainings. It’s what Sean calls a focus on consumption over conversion. That’s position two.

So what’s the conclusion? I guess it depends on what kind of business you’re looking to run. If you want to scale quickly and max out revenue, then aggressive “steak” upsells make sense. If you want to have a long-term business, another strategy might be better.

For example, even in Sean’s way of running a business, the right kinds of upsells can have a place.

Imagine if in that restaurant, the waiter did something different. Imagine if instead of upselling you on more steak, he recommended a special beer on tap, and his favorite salad off the menu. This would still be an upsell, though it wouldn’t make as much money as selling more steak.

Your consumption experience would be much better. You’d be more likely to return. And the restaurant wouldn’t have to constantly worry about digging up new customers.

Shooting off a couple of impossible bullets

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An impossible bet

There’s a video of Ricky Jay at the end of a poker night, doing one last trick for his friends.

He fills a glass with water, puts a playing card on top of it. He then rolls up a second playing card into a little tube and puts this on top of the first playing card, and then puts an egg on top of the tube. “Here’s the bet,” he tells the rest of the guys. “I bet you that by throwing a card I can make the egg land inside the glass. Do I have any takers?”

It’s an impossible bet. The glass is covered by a card so there’s no way for the egg to get through. And all he’s got is some playing cards to throw. Of course, somebody takes him up on the bet. And yet, he throws the card, and gets the egg in the glass.

Today, I worked on a sales page for a video course on cryptocurrency investing. 80% of the sales page was bullets. Warning and danger bullets. Straight up benefit bullets. Curiosity bullets. And peppered in among these, a special breed, which I call impossibility bullets:

  • How to get an extra 10% return on your Bitcoin investment — even if the price doesn’t move one bit
  • How to take advantage of a crypto bull run — even while you sleep
  • How to safely use your cryptocurrencies — even on a computer infected with malware

Now that I’ve pulled them out, I realized they all had the same format:

HOW TO [GENERIC BENEFIT] — EVEN IF [SEEMINGLY INSURMOUNTABLE OBSTACLE]

In all 3 cases, the bullets wrote themselves, because there was an underlying mechanism which offered a surprising benefit. At the same time, I don’t think I could get away with these kinds of bullets too often — people would get skeptical instead of curious. (Unfortunately, copywriting isn’t a magic show — and people don’t like to be fooled by a sales page.) In this case, I think it will work, because the remaining 90% of the bullets are more moderate, and because there is other proof throughout the rest of the copy.

The only way to evaluate copy

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Three wise men doing a copy critique

Professor Skridlov: Father Giovanni, how can you stay here instead of returning to Italy and giving the people there something of the faith which you are now inspiring in me?

Father Giovanni: Ah Professor. You do not understand man’s psyche as well as you know archeology. Faith cannot be given to men. Faith is not the result of thinking. It comes from direct knowledge.

I started re-reading Gene Schwartz’s Breakthrough Advertising. And right on the first page, he offers this warning:

“Copy cannot create desire for a product. It can only take the hopes, dreams, fears and desires in the hearts of millions of people, and focus those already-existing desires on a particular product.”

And here’s another related quote, this from Gary Halbert:

“You know, I’m sick to death of people who can’t be bothered with the little nitty-gritty details of “hands on” experience. Of people who believe that somehow they can know a thing without experiencing it. Listen: It is possible to be “conversant” with something and really not have any kind of “gut understanding” of it at all. I’m sorry, but no matter what your Mommy and Daddy told you, men can never really understand the pain of childbirth, priests cannot comprehend the joys of sex, “normies” can never understand alcoholics, and not one speck of true advertising wisdom has ever been written by a PhD.”

And finally, a bit from a recent Ben Settle email:

“This is, btw, why I don’t do critiques anymore. (Besides the fact I hate doing copywriting critiques) As Doug D’Anna put it in the same interview: ‘How can I offer somebody a copywriting critique on a piece of sales copy for a product or a prospect that I am 100 percent unfamiliar with?'”

Here’s how this ties together in my head.

Nobody can really judge good copy unless they are a prospect and ready to buy. Nice-sounding copy can bomb. Awful copy can sell.

So how do you write good copy? Research is important. So is experience. So is intuition. Then there’s feedback from other experts.

All that stuff is great, but ultimately, none of it is conclusive.

Fortunately, direct response copywriting is one area where we don’t have to agree to disagree. We can know which appeal is best. Even if we cannot see inside people’s hearts, and even though we cannot have their problems (or faith). And that’s simply through sales.

A bizarre example of disconnected infotainment

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Photographer Leopold Kanzler worked with this beaver for two weeks hiding apple slices in his camera to get this shot. “I’m not sure who had more fun, me or the beaver, but it seemed more than happy with receiving so many tasty treats.”

I just finished reading the Dartboard Pricing book from Sean D’Souza. It’s the first of his paid products that I’ve read. And there were many things from this book, besides the content, that I thought were worth adopting.

Once upon a time I read an article of Sean’s on the topic of infotainment. He had various bits of advice, and one of them was something like:  “You can connect or disconnect the entertaining part to the information part at will.”

In other words, if you are writing an email or a blog post or a book, it’s important that the email or blog post or book is fun to read. It’s also important that it has valuable content. The entertainment and the content can be connected, but they don’t always have to be.

In Sean’s Pricing book, he has lots of what you could call infotainment. Cartoons. Stories. And then, there’s a recipe for chicken biryani, spread over 3 pages.

The cartoons and stories tie into the content of the book. The chicken biryani does not, at least as far as I can see.

To sum up, connect or disconnect the infotainment at will. But my gut feeling is — there’s value in occasionally disconnected infotainment — it keeps people surprised and gives a sense of wonder.

I don’t think it’s something to do all the time. But once in a while, it’s better to throw in something fun and bizarre, rather than fun but reasonable.